Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising the same, which can achieve an improvement in efficiency, a lower driving voltage and / or an improvement in lifespan characteristics by a hole and electron balance of an organic light-emitting device according to a chemical structure of the chemical formula 1 above, and an organic light-emitting device comprising the same.

Description

TECHNICAL FIELD

[0001] This application claims priority to Korean Patent Application No. 10-2024-0027048, filed on February 26, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein.

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

[0003] Generally, an organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using an organic substance. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different substances, respectively, for example, can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when the excitons re-trip to a ground state, light is emitted.

[0004] There is a continuous demand for development of new materials for an organic light emitting device as described above. SUMMARY

[0005] TECHNICAL PROBLEM

[0006] The present specification provides a compound and an organic light emitting device including the same.

[0007] SOLUTION TO PROBLEM

[0008] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above Chemical Formula 1,

[0012] at least two of X1 to X3 are N, and the rest are CH,

[0013] at least two of X4 to X6 are N, and the rest are CH,

[0014] R1 to R11 are the same as or different from each other, and each is independently hydrogen, deuterium, or a cyano group,

[0015] r10 is 1 or 2, and when the above r10 is 2, the above two R10 are the same as or different from each other,

[0016] r11 is an integer of 1 to 4, and when r11 is 2 or more, the two or more R11s are the same or different,

[0017] Ar1to Ar4are the same as or different from each other, and each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0018] ar1 is an integer of 1 to 5, and when ar1 is 2 or more, the two or more Ar1s are the same or different from each other,

[0019] ar2 is an integer of 1 to 5, and when ar2 is 2 or more, the two or more Ar2s are the same or different from each other,

[0020] ar3 is an integer of 1 to 5, and when ar3 is 2 or more, the two or more Ar3s are the same or different from each other,

[0021] ar4 is an integer of 1 to 5, and when ar4 is 2 or more, the two or more Ar4s are the same or different from each other,

[0022] any one or two of Y1to Y5is N, and the rest are each independently CR'1,

[0023] R'1is hydrogen, deuterium, a cyano group, or a substituted or unsubstituted alkyl group, or combines with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0024] In addition, one embodiment of the present specification provides an organic light-emitting device including: a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound.

[0025] Effects of the Invention

[0026] The compound according to one embodiment of the present specification can be used as a material for an organic layer of an organic light-emitting device, and preferably, can be used in an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0027] By using the compound, improvement in efficiency, a lower driving voltage, and / or improvement in lifespan characteristics can be achieved in an organic light-emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figure 1 and 2 FIG. 1 illustrates an example of an organic light-emitting device according to one embodiment of the present specification.

[0029] [Explanation of Symbols]

[0030] 1: substrate

[0031] 2: first electrode

[0032] 3: organic layer

[0033] 4: second electrode

[0034] 5: hole injection layer

[0035] 6: hole transport layer

[0036] 7: electron blocking layer

[0037] 8: light emitting layer

[0038] 9: hole blocking layer

[0039] 10: electron injection and transport layer DETAILED DESCRIPTION

[0040] Hereinafter, the present specification will be described in more detail.

[0041] One embodiment of the present specification provides the above compound of Chemical Formula 1.

[0042] The compound of Chemical Formula 1 according to one embodiment of the present specification has a low voltage, high efficiency characteristic by adjusting the electron mobility of an organic light emitting device including the same through substitution of an N-containing heterocycle between a diphenyltriazine or a diphenylpyrimidine which plays a role of an electron donor and an acceptor. In addition, the N-containing monocyclic heterocycle of the present application of Chemical Formula 1 plays a role of an electron-attracting heterocycle, and has a long lifespan characteristic by lowering the LUMO value, and thus an organic light emitting device including the same has a long lifespan characteristic.

[0043] In the specification of the present application throughout, the term of "their combinations" contained in the expression of Markush form means a mixture or combination of one or more selected from the constituent elements described in the expression of Markush form, and means to include one or more selected from the above constituent elements.

[0044] In the present specification, examples of substituents are described below, but are not limited thereto.

[0045] In the present specification, represents a site of connection.

[0046] The above term of "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents can be the same as or different from each other.

[0047] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a halogenated alkyl group, a silyl group, a boron group, an amine group, an aryl group, and a heteroaryl group, or connected with two or more of the above-mentioned substituents, or not having any substituent.

[0048] In the present specification, connection of two or more substituents means that a hydrogen of any one of the substituents is connected with the other substituent. For example, connection of two substituents can be connection of a phenyl group and a naphthyl group to become or such a substituent. Furthermore, connection of three substituents includes not only (substituent 1) - (substituent 2) - (substituent 3) connected in series, but also (substituent 1) connected with (substituent 2) and (substituent 3). For example, a phenyl group, a naphthyl group, and an isopropyl group can be connected to become , or such a substituent. The same applies to connection of four or more substituents.

[0049] In the present specification, examples of the halogen group include a fluorine group, a chlorine group, a bromine group, or an iodine group.

[0050] In the present specification, the above-mentioned alkyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. As specific examples, there are a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a t-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, an n-octyl group, a t-octyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an iso-hexyl group, a 2-methylpentyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but is not limited thereto.

[0051] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-t-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

[0052] In the present specification, the above-mentioned alkoxy group can be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably from 1 to 30. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like, but is not limited thereto.

[0053] In the present specification, the above-mentioned alkenyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 30. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-buten- dienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- (naphth-1-yl)vinyl-1-yl, 2,2-bis(diphen-1-yl)vinyl-1-yl, stilbenyl, styryl, and the like, but is not limited thereto.

[0054] In the present specification, the above-mentioned haloalkyl group refers to a group in which at least one halogen group is substituted for the hydrogen of the alkyl group in the definition of the above-mentioned alkyl group.

[0055] In the present specification, the above-mentioned aryl group is not particularly limited, and is preferably an aryl group having from 6 to 30 carbon atoms. The above-mentioned aryl group can be monocyclic or polycyclic.

[0056] When the above-mentioned aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably from 6 to 30. Specifically, as a monocyclic aryl group, there can be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

[0057] When the above-mentioned aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably from 10 to 30. Specifically, as a polycyclic aryl group, there can be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

[0058] In the present specification, the above-mentioned fluorenyl group can be substituted, and adjacent groups can be bonded to each other to form a ring.

[0059] In the case where the above-mentioned fluorenyl group is substituted, it can be and the like, but is not limited thereto.

[0060] In the present specification, "adjacent" groups can mean a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest in the steric structure to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, 2 substituents substituted at the ortho position in a benzene ring and 2 substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0061] In the present specification, a heteroaryl group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the above heteroatoms can contain 1 or more atoms selected from O, N, Se, P, Si, and S, etc. The number of carbon atoms in the above heteroaryl group is not particularly limited, but is preferably 2 to 30, and the above heteroaryl group can be monocyclic or polycyclic. As examples of the heteroaryl group, there are thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phtalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benz oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridine, phenanthroline, iso oxazolyl, thiazolyl, dibenzofuranyl, dibenzothiopholyl, phen oxazolyl, thiazolyl, dibenzofuranyl, dibenzothiopholyl, phen oxazolyl, thiazolyl, dibenzofuranyl, dibenzothiopholyl, phen

[0062] In the present specification, a silyl group can be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the above alkylsilyl group can apply the above examples of the alkyl group, the aryl group in the above arylsilyl group can apply the above examples of the aryl group, and the heteroaryl group in the above heteroarylsilyl group can apply the above examples of the heterocyclic group.

[0063] In the present specification, a boron group can be -BG 100 G 101 , the above G 100 and G 101The same or different, each independently can be selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted straight chain or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The above boron group is specifically dimethylboron group, diethylboron group, t-butylmethylboron group, diphenylboron group, etc., but is not limited thereto.

[0064] In the present specification, the amine group can be selected from -NH2, alkylamine group, N-alkyl arylamine group, arylamine group, N-aryl heteroarylamine group, N-alkyl heteroarylamine group, and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. As specific examples of the amine group, there are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthrylamine group, 9-methyl-anthrylamine group, diphenylamine group, ditolylamine group, N-phenyl tolylamine group, N-phenyl biphenylamine group, N-phenyl naphthylamine group, N-biphenyl naphthylamine group, N-naphthyl fluoreneamine group, N-phenyl phenanthrylamine group, N-biphenyl phenanthrylamine group, N-phenyl fluoreneamine group, N-phenyl terphenylamine group, N-phenanthryl fluoreneamine group, N-biphenyl fluoreneamine group, etc., but is not limited thereto.

[0065] In the present specification, the N-alkyl arylamine group means an amine group having an alkyl group and an aryl group substituted on the N of the amine group. The alkyl group and the aryl group in the above N-alkyl arylamine group are the same as the examples of the above alkyl group and the aryl group.

[0066] In the present specification, the N-aryl heteroarylamine group means an amine group having an aryl group and a heteroaryl group substituted on the N of the amine group. The aryl group and the heteroaryl group in the above N-aryl heteroarylamine group are the same as the examples of the above aryl group and the heteroaryl group.

[0067] In the present specification, the N-alkyl heteroarylamine group means an amine group having an alkyl group and a heteroaryl group substituted on the N of the amine group. The alkyl group and the heteroaryl group in the above N-alkyl heteroarylamine group are the same as the examples of the above alkyl group and the heteroaryl group.

[0068] In the present specification, as examples of the arylamine group, there are substituted or unsubstituted monoarylamine group, or substituted or unsubstituted diarylamine group. The arylamine group containing 2 or more of the above aryl groups can contain a monocyclic aryl group, a polycyclic aryl group, or can contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the above arylamine group can be selected from the examples of the above aryl group.

[0069] In the present specification, as examples of the heteroaryl group, there are substituted or unsubstituted mono-heteroaryl group, or substituted or unsubstituted di-heteroaryl group. The heteroaryl group containing two or more of the above heteroaryl groups can contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or can contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the above heteroaryl group can be selected from the above examples of the heteroaryl group.

[0070] In the present specification, the alkyl group in the alkylthio group ) and the alkylsulfonyl group ) is the same as the above examples of the alkyl group. Specifically, as the alkylthio group, there are methylthio group, ethylthio group, tert-butylthio group, hexylthio group, octylthio group, and the like, and as the alkylsulfonyl group, there are methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, and the like, but not limited thereto.

[0071] In the present specification, the phosphine oxide group specifically has an alkylphosphine oxide group, an arylphosphine oxide group, and the like, and more specifically, there are a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but not limited thereto.

[0072] In the present specification, the aryl group in the aryloxy group, the arylthio group ), the arylsulfonyl group ), and the arylphosphine group is the same as the above examples of the aryl group. Specifically, as the aryloxy group, there are phenoxy group, p-methylphenoxy group, m-methylphenoxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthyloxy group, 2-anthyloxy group, 9-anthyloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like, as the arylthio group, there are phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group, and the like, and as the arylsulfonyl group, there are phenylsulfonyl group, p-tolylsulfonyl group, and the like, but not limited thereto.

[0073] In the present specification, "adjacent groups are combined with each other to form a ring" in the substituent means that a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle is formed by combining adjacent groups with each other.

[0074] In the present specification, in the substituted or unsubstituted ring formed by combining with each other, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0075] In the present specification, the hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and can be selected from the above examples of the cycloalkyl group or the aryl group, except that it is not monovalent.

[0076] In the present specification, a heterocycle contains one or more non-carbon atoms, i.e., heteroatoms, and specifically, the above heteroatoms can contain one or more atoms selected from O, N, Se, and S, etc. The above heterocycle can be a monocyclic or polycyclic ring, and can be an aromatic, aliphatic, or fused ring of an aromatic and aliphatic. The above aromatic heterocycle, except for being monovalent, can be selected from the above examples of the heteroaryl group.

[0077] In the present specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. As examples of the aliphatic heterocycle, there are oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepin, ), azocane ), thioxane

[0078] In the present specification, an arylene group refers to a group having two bonding sites on an aryl group, i.e., a divalent group. They can be applicable to the above description of the aryl group, except for each being a divalent group.

[0079] Unless defined otherwise in the present specification, all technical and scientific terms used in the present specification have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present application, but the following procedures and materials are described in order to provide illustrative embodiments. All publications, patent applications, patents, and other references mentioned in the present specification are incorporated by reference in their entirety into the present specification, but in the case of conflict, the present specification, including the definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0080] Hereinafter, the compound represented by the above Chemical Formula 1 will be described in detail.

[0081] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-5.

[0082] [Chemical Formula 1-1]

[0083]

[0084] [Chemical Formula 1-2]

[0085]

[0086] [Chemical Formula 1-3]

[0087] ​​

[0088] [Chemical Formula 1-4]

[0089]

[0090] [Chemical Formula 1-5]

[0091]

[0092] In the above Chemical Formulas 1-1 to 1-5,

[0093] X1to X6, Y1to Y5, R1to R9, R11, r11, Ar1to Ar4, and ar1to ar4are the same as the definitions in Chemical Formula 1.

[0094] R101to R104, which are the same as or different from each other, are each independently hydrogen, deuterium, or a cyano group.

[0095] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-6 to 1-9.

[0096] [Chemical Formula 1-6]

[0097]

[0098] [Chemical Formula 1-7]

[0099]

[0100] [Chemical Formula 1-8]

[0101]

[0102] [Chemical Formula 1-9]

[0103]

[0104] In the above Chemical Formulas 1-6 to 1-9,

[0105] X1to X6, Y1to Y5, R1to R11, r10, r11, Ar1to Ar4, and ar1to ar4are the same as the definitions in Chemical Formula 1.

[0106] According to an embodiment of the present specification, the above Y1is N, and Y2to Y5are each independently CR'1.

[0107] According to an embodiment of the present specification, the above Y2is N, and Y1and Y3to Y5are each independently CR'1.

[0108] According to an embodiment of the present specification, the above Y3 is N, and Y1, Y2, Y4, and Y5 are each independently CR'1.

[0109] According to an embodiment of the present specification, the above Y1 and Y2 are N, and Y3 to Y5 are each independently CR'1.

[0110] According to an embodiment of the present specification, the above Y1 and Y3 are N, and Y2, Y4, and Y5 are each independently CR'1.

[0111] According to an embodiment of the present specification, the above Y1 and Y4 are N, and Y2, Y3, and Y5 are each independently CR'1.

[0112] According to an embodiment of the present specification, the above Y1 and Y5 are N, and Y2 to Y4 are each independently CR'1.

[0113] According to an embodiment of the present specification, the above Y2 and Y3 are N, and Y1, Y4, and Y5 are each independently CR'1.

[0114] According to an embodiment of the present specification, the above Y2 and Y4 are N, and Y1, Y3, and Y5 are each independently CR'1.

[0115] According to an embodiment of the present specification, the above Y2 and Y5 are N, and Y1, Y3, and Y4 are each independently CR'1.

[0116] According to an embodiment of the present specification, the above Y3 and Y4 are N, and Y1, Y2, and Y5 are each independently CR'1.

[0117] According to an embodiment of the present specification, the above Y3 and Y5 are N, and Y1, Y2, and Y4 are each independently CR'1.

[0118] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following structural formulas.

[0119]

[0120] In the above structural formula,

[0121] is a site combined with the above Chemical Formula 1,

[0122] R'11 to R'15 are the same as or different from each other, and are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted alkyl group, or are each independently combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0123] According to an embodiment of the present specification, the above X1 to X3 are N.

[0124] According to an embodiment of the present specification, X1and X2are N, and X3is CH.

[0125] According to an embodiment of the present specification, X1and X3are N, and X2is CH.

[0126] According to an embodiment of the present specification, X2and X3are N, and X1is CH.

[0127] According to an embodiment of the present specification, X4to X6are N.

[0128] According to an embodiment of the present specification, X4and X5are N, and X6is CH.

[0129] According to an embodiment of the present specification, X4and X6are N, and X5is CH.

[0130] According to an embodiment of the present specification, X5and X6are N, and X4is CH.

[0131] According to an embodiment of the present specification, the above Chemical Formula 1 is is any one of the following structures.

[0132]

[0133] In the above structural formula,

[0134] is a site combined with Chemical Formula 1,

[0135] Ar1, Ar2, ar1, and ar2 are the same as defined in the above Chemical Formula 1.

[0136] According to an embodiment of the present specification, the above Chemical Formula 1 is is any one of the following structures.

[0137]

[0138] In the above structural formula,

[0139] is a site combined with Chemical Formula 1,

[0140] Ar3, Ar4, ar3, and ar4 are the same as defined in the above Chemical Formula 1.

[0141] According to an embodiment of the present specification, the above Chemical Formula 1 is and are different from each other.

[0142] According to an embodiment of the present specification, the above Chemical Formula 1 is and are the same as each other.

[0143] According to one embodiment of the present specification, the above R1 to R11 are the same as or different from each other, and each is independently hydrogen, deuterium, or a cyano group.

[0144] According to one embodiment of the present specification, the above R1 to R11 are hydrogen.

[0145] According to one embodiment of the present specification, the above R1 to R11 are deuterium.

[0146] According to one embodiment of the present specification, one or more of the above R1 to R11 are deuterium.

[0147] According to one embodiment of the present specification, the above R1 to R11 are a cyano group.

[0148] According to one embodiment of the present specification, one or more of the above R1 to R11 are a cyano group.

[0149] According to one embodiment of the present specification, the above Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

[0150] The above R'1 is hydrogen, deuterium, a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0151] According to one embodiment of the present specification, the above Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, a cyano group, a methyl group, or a pyridyl group.

[0152] According to one embodiment of the present specification, the above Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0153] According to one embodiment of the present specification, the above Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted cyano group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0154] According to an embodiment of the present specification, the above Ar1to Ar4are the same as or different from each other, and each is independently hydrogen, deuterium, a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

[0155] According to an embodiment of the present specification, the above Ar1to Ar4are the same as or different from each other, and each is independently hydrogen, deuterium, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0156] According to an embodiment of the present specification, the above Ar1to Ar4are the same as or different from each other, and each is independently hydrogen, deuterium, a cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0157] According to an embodiment of the present specification, the above Ar1to Ar4are the same as or different from each other, and each is independently hydrogen, deuterium, or a cyano group.

[0158] According to an embodiment of the present specification, the above Ar1to Ar4are hydrogen.

[0159] According to an embodiment of the present specification, the above Ar1to Ar4are deuterium.

[0160] According to an embodiment of the present specification, the above Ar1to Ar4are a cyano group.

[0161] According to an embodiment of the present specification, one or more of the above Ar1to Ar4is deuterium.

[0162] According to an embodiment of the present specification, one of the above Ar1to Ar4is deuterium.

[0163] According to an embodiment of the present specification, two of the above Ar1to Ar4are deuterium.

[0164] According to an embodiment of the present specification, three of the above Ar1to Ar4are deuterium.

[0165] According to an embodiment of the present specification, one or more of the above Ar1to Ar4is a cyano group.

[0166] According to an embodiment of the present specification, two of the above Ar1to Ar4are a cyano group.

[0167] According to an embodiment of the present specification, three of the above Ar1to Ar4are a cyano group.

[0168] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a substituted or unsubstituted linear or branched alkyl group having a carbon atom number of 1 to 30, or is linked to an adjacent group to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having a carbon atom number of 6 to 30.

[0169] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a substituted or unsubstituted linear or branched alkyl group having a carbon atom number of 1 to 20, or is linked to an adjacent group to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having a carbon atom number of 6 to 20.

[0170] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or an alkyl group, or is linked to an adjacent group to each other to form an aromatic hydrocarbon ring.

[0171] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a linear or branched alkyl group having a carbon atom number of 1 to 30, or is linked to an adjacent group to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having a carbon atom number of 6 to 30.

[0172] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a linear or branched alkyl group having a carbon atom number of 1 to 20, or is linked to an adjacent group to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having a carbon atom number of 6 to 20.

[0173] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a methyl group, or is linked to an adjacent group to each other to form a benzene ring.

[0174] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a substituted or unsubstituted linear or branched alkyl group having a carbon atom number of 1 to 30.

[0175] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a substituted or unsubstituted linear or branched alkyl group having a carbon atom number of 1 to 20.

[0176] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or an alkyl group.

[0177] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a linear or branched alkyl group having a carbon atom number of 1 to 30.

[0178] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a linear or branched alkyl group having a carbon atom number of 1 to 20.

[0179] According to an embodiment of the present specification, the above R'1is hydrogen, deuterium, a cyano group, or a methyl group.

[0180] According to an embodiment of the present specification, the above R'1 and the adjacent groups combine with each other to form a substituted or unsubstituted, monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0181] According to an embodiment of the present specification, the above R'1 and the adjacent groups combine with each other to form a substituted or unsubstituted, monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0182] According to an embodiment of the present specification, the above R'1 and the adjacent groups combine with each other to form an aromatic hydrocarbon ring.

[0183] According to an embodiment of the present specification, the above R'1 and the adjacent groups combine with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0184] According to an embodiment of the present specification, the above R'1 and the adjacent groups combine with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0185] According to an embodiment of the present specification, the above R'1 and the adjacent groups combine with each other to form a benzene ring.

[0186] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following compounds.

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] One embodiment of the present specification provides an organic light emitting device including a compound represented by Chemical Formula 1.

[0215] In the present specification, when a certain part is referred to as being "on" another part, it can be directly on the other part or an intervening part can also be present.

[0216] In the present specification, when a certain part "comprises" or "includes" a certain component, unless it is specifically stated otherwise, it means that it can further include another component, rather than excluding another component.

[0217] In the present specification, the above "layer" is interchangeably used with "film" which is mainly used in the technical field, and means a coating layer covering a target area. The size of the above "layer" is not limited, and the size of each "layer" can be the same or different. According to one embodiment, the size of the "layer" can be equal to the entire device, can correspond to the size of a specific functional area, or can be as small as a single sub-pixel.

[0218] In the present specification, the meaning that a specific A substance is contained in a B layer includes both i) a case where one or more A substances are contained in a B layer of one layer, and ii) a case where a B layer is composed of one or more layers and one or more A substances are contained in one or more of the B layers.

[0219] In the present specification, the meaning that a specific A substance is contained in a C layer or a D layer includes all of i) one or more of a C layer, ii) one or more of a D layer, or iii) one or more of a C layer and one or more of a D layer, respectively.

[0220] The present specification provides an organic light emitting device including: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, one or more of the organic layers containing a compound represented by Chemical Formula 1.

[0221] The organic layer of the organic light emitting device of the present specification can be formed of a single layer structure, or can be formed of a multilayer structure in which two or more organic layers are stacked. For example, it can have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron suppression layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller number of organic layers.

[0222] According to an embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

[0223] According to an embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer contains the compound.

[0224] According to an embodiment of the present specification, the organic layer includes a light emitting layer.

[0225] According to an embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0226] According to an embodiment of the present specification, the organic layer includes an electron suppression layer.

[0227] According to an embodiment of the present specification, the organic layer includes a hole blocking layer.

[0228] According to an embodiment of the present specification, the organic light emitting device described above further includes 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron inhibiting layer.

[0229] According to an embodiment of the present specification, the organic light emitting device described above includes: a first electrode; a second electrode disposed opposite to the first electrode; a light emitting layer disposed between the first electrode and the second electrode; and 2 layers or more of organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

[0230] According to an embodiment of the present specification, the 2 layers or more of organic layers described above can be selected from 2 layers or more of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron inhibiting layer.

[0231] According to an embodiment of the present specification, 2 layers or more of a hole transport layer are included between the light emitting layer and the first electrode. The 2 layers or more of a hole transport layer can include the same or different substances from each other.

[0232] According to an embodiment of the present specification, the first electrode is an anode or a cathode.

[0233] According to an embodiment of the present specification, the second electrode is a cathode or an anode.

[0234] According to an embodiment of the present specification, the organic light emitting device described above can be an organic light emitting device of a structure (normal type) in which an anode, 1 layer or more of an organic layer, and a cathode are sequentially stacked on a substrate.

[0235] According to an embodiment of the present specification, the organic light emitting device described above can be an organic light emitting device of a structure (inverted type) in which a cathode, 1 layer or more of an organic layer, and an anode are sequentially stacked on a substrate.

[0236] For example, the structure of the organic light emitting device according to an embodiment of the present specification is illustrated in Figure 1 and Figure 2 . The structures of the organic light emitting device described above Figure 1 and Figure 2 are not limited thereto.

[0237] Figure 1 The structure of the organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1 is illustrated in the above chemical formula 1. The compound represented by the above chemical formula 1 is included in the organic layer.

[0238] Figure 2 A structure of an organic light emitting device in which a first electrode 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 second electrode 4 are sequentially stacked on a substrate 1 is exemplified. The compound represented by the above formula 1 is contained in the electron injection and transport layer 10.

[0239] The organic light emitting device of the present specification can be manufactured by known materials and methods in the technical field, except that the above compound, i.e., the compound represented by the above formula 1, is contained in the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer.

[0240] When the above organic light emitting device includes a plurality of organic layers, the above organic layers can be formed of the same substance or different substances.

[0241] For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: an anode is formed by evaporating a metal or a metal oxide having conductivity or an alloy thereof on a substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation, and then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and after that, a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0242] In addition, the compound represented by the above formula 1 can be used to form an organic layer not only by a vacuum evaporation method but also by a solution coating method when manufacturing an organic light emitting device. Here, the solution coating method refers to a spin coating method, a dip coating method, a blade coating method, an inkjet printing method, a screen printing method, a spray method, a roll coating method, etc., but is not limited thereto.

[0243] In addition to these methods, an organic light emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate. However, the manufacturing method is not limited thereto.

[0244] As the anode material described above, a material having a large work function is generally preferred in order to easily inject holes into the organic layer. Examples of such a material include metals such as vanadium, chromium, copper, zinc, gold, and the like, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; conductive high molecular weight compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.

[0245] As the cathode material described above, a material having a small work function is generally preferred in order to easily inject electrons into the organic layer. Examples of such a material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0246] The hole injection layer described above is a layer that receives holes from the electrode. The hole injection material is preferably a material that has a capability of transporting holes, has an effect of receiving holes from the anode, and has an excellent hole injection effect to the light emitting layer or the light emitting material. Further, it is preferable that the material have an excellent capability of preventing excitons generated in the light emitting layer from migrating to the electron injection layer or the electron injection material. Furthermore, it is preferable that the material have an excellent film formation capability. Further, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic material; quinacridone-based organic material; perylene-based organic material; anthraquinone, polyaniline, and polythiophene-based conductive high molecular weight compound, but are not limited thereto.

[0247] According to an embodiment of the present specification, the hole injection layer described above contains a compound represented by the following Chemical Formula HI-1, but is not limited thereto.

[0248] [Chemical Formula HI-1]

[0249]

[0250] In the Chemical Formula HI-1 described above,

[0251] R400 to R402 are the same as or different from each other, and each is independently any one selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted heteroaryl group, and a combination thereof, or combine with an adjacent group to each other to form a substituted or unsubstituted ring,

[0252] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0253] According to an embodiment of the present specification, the above-described R400 to R402 are the same as or different from each other, and each is independently 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 a combination thereof.

[0254] According to an embodiment of the present specification, the above-described R402 is any one selected from the group consisting of a phenyl group substituted with a carbazolyl group or an arylamine group, a biphenyl group substituted with a carbazolyl group or an arylamine group, and a combination thereof.

[0255] According to an embodiment of the present specification, the above-described R400 and R401 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or combine with an adjacent group to each other to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0256] According to an embodiment of the present specification, the above-described R400 and R401 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0257] According to an embodiment of the present specification, the above-described R400 and R401 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, or a dimethylfluorene group.

[0258] According to an embodiment of the present specification, the above-described Chemical Formula HI-1 is selected from the following compounds.

[0259]

[0260] According to an embodiment of the present specification, the above-described hole injection layer includes a compound represented by the following Chemical Formula HI-2, but is not limited thereto.

[0261] [Chemical Formula HI-2]

[0262]

[0263] In the above-described Chemical Formula HI-2,

[0264] X'1 to X'3 are the same as or different from each other, and each is independently hydrogen, deuterium, or a halogen group,

[0265] R309 to R314 are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0266] x1' to x3' are each an integer of 1 to 4, and when they are 2 or more, the substituents within the parentheses are the same as or different from each other.

[0267] According to an embodiment of the present specification, X'1 to X'3 are halogen groups.

[0268] According to an embodiment of the present specification, X'1 to X'3 are F or Cl.

[0269] According to an embodiment of the present specification, X'1 to X'3 are F.

[0270] According to an embodiment of the present specification, R309 to R314 are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted amine group.

[0271] According to an embodiment of the present specification, R309 to R314 are the same as or different from each other, and each independently hydrogen, deuterium, or a nitrile group.

[0272] According to an embodiment of the present specification, R309 to R314 are a nitrile group.

[0273] According to an embodiment of the present specification, the above-described Chemical Formula HI-2 is represented by the following compound.

[0274]

[0275] The hole transport layer receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport substance is a substance capable of receiving holes from the anode or the hole injection layer and transferring them to the light-emitting layer, and is preferably a substance having a large mobility for holes. As specific examples, there are arylamine-based organic substances, electrically conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but are not limited thereto.

[0276] According to an embodiment of the present specification, the hole transport layer contains a compound represented by the following Chemical Formula HT-2, but is not limited thereto.

[0277] [Chemical Formula HT-2]

[0278]

[0279] In the above-described Chemical Formula HT-2,

[0280] R403 to R406 are the same as or different from each other, and each independently is any one selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted heteroaryl group, and a combination thereof, or combine with an adjacent group to form a substituted or unsubstituted ring,

[0281] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0282] l403 is an integer of 1 to 3, and L403 are the same as or different from each other when l403 is 2 or more.

[0283] According to one embodiment of the present specification, the above 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 a combination thereof.

[0284] According to one embodiment of the present specification, the above R403 to R406 are the same as or different from each other, and each independently is an aryl group having 6 to 30 carbon atoms.

[0285] According to one embodiment of the present specification, the above R403 to R406 are the same as or different from each other, and each independently is a phenyl group, a biphenyl group, or a naphthyl group.

[0286] According to one embodiment of the present specification, the above R403 to R406 are the same as or different from each other, and each independently is a phenyl group.

[0287] According to one embodiment of the present specification, the above 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.

[0288] According to one embodiment of the present specification, the above L403 is a phenylene group, a bivalent biphenyl group, or a bivalent carbazolyl group substituted or unsubstituted with an aryl group.

[0289] According to one embodiment of the present specification, the above L403 is a bivalent carbazolyl group substituted with a naphthyl group.

[0290] According to one embodiment of the present specification, the above Chemical Formula HT-2 is selected from the following compounds.

[0291]

[0292] The above electron-suppressing layer is a layer that prevents electrons injected from the electron-injecting layer from passing through the light-emitting layer to enter the hole-injecting layer, thereby improving the lifespan and efficiency of the device. A well-known material can be used without limitation, and can be formed between the light-emitting layer and the hole-injecting layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0293] According to an embodiment of the present specification, the above-mentioned electron-inhibiting layer contains a compound represented by the following Chemical Formula EB-1, but is not limited thereto.

[0294] [Chemical Formula EB-1]

[0295]

[0296] In the above-mentioned Chemical Formula EB-1,

[0297] R318 to R320 are the same as or different from each other, and each is independently any one selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof, or combine with an adjacent group to each other to form a substituted or unsubstituted ring,

[0298] r318 is an integer of 1 to 5, and when the above-mentioned r318 is 2 or more, 2 or more of the above-mentioned R318 are the same as or different from each other,

[0299] r319 is an integer of 1 to 5, and when the above-mentioned r319 is 2 or more, 2 or more of the above-mentioned R319 are the same as or different from each other.

[0300] According to an embodiment of the present specification, the above-mentioned R320 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.

[0301] According to an embodiment of the present specification, the above-mentioned R320 is any one selected from the group consisting of a phenyl group, a biphenyl group, a carbazolyl group, and a combination thereof.

[0302] According to an embodiment of the present specification, the above-mentioned R318 and R319 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or combine with an adjacent group to each other to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0303] According to an embodiment of the present specification, the above-mentioned R318 and R319 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, or a phenanthryl group.

[0304] According to an embodiment of the present specification, the above-mentioned Chemical Formula EB-1 is represented by the following compound.

[0305]

[0306] The light-emitting layer described above can contain a host material and a dopant material. The host material is an aromatic condensed ring derivative or a heterocyclic compound, or the like. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and as the heterocyclic compound, there are dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the present application is not limited thereto.

[0307] According to an embodiment of the present specification, the above host contains a compound represented by the following Chemical Formula H-1, but is not limited thereto.

[0308] [Chemical Formula H-1]

[0309]

[0310] In the above Chemical Formula H-1,

[0311] L20and L21are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0312] Ar20and Ar21are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0313] R201is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0314] r201is an integer of 1 to 8, and when the above r201is 2 or more, 2 or more R201are the same as or different from each other.

[0315] In an embodiment of the present specification, the above L20and L21are the same as or different from each other, and each independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0316] In an embodiment of the present specification, the above L20and L21are the same as or different from each other, and each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, a naphthalene group substituted or unsubstituted with deuterium, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0317] In an embodiment of the present specification, the above Ar20and Ar21are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. ​

[0318] In one embodiment of the present specification, the aforementioned Ar20and Ar21are the same as or different from each other, and each independently a substituted or unsubstituted, monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted, monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0319] In one embodiment of the present specification, the aforementioned Ar20and Ar21are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted biphenyl group with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted naphthyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted thienyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted dibenzofuranyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted naphthobenzofuranyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted dibenzothiophenyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted naphthobenzothiophenyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0320] In one embodiment of the present specification, the aforementioned Ar20and Ar21are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted biphenyl group with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted naphthyl group with deuterium, a phenyl group substituted or unsubstituted thienyl group with a phenyl group, a phenanthryl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, or a naphthobenzothiophenyl group.

[0321] In one embodiment of the present specification, the aforementioned Ar20and Ar21are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

[0322] In one embodiment of the present specification, the aforementioned Ar20and Ar21are the same as or different from each other, and each independently a 1-naphthyl group or a 2-naphthyl group.

[0323] According to one embodiment of the present specification, the aforementioned R201is hydrogen or a phenyl group.

[0324] According to one embodiment of the present specification, the aforementioned Chemical Formula H-1 is represented by the following compound.

[0325]

[0326] As the above-mentioned dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives are aromatic condensed ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, chrysene, diindenoperylene, and the like having arylamino groups. Further, the styryl amine compounds are compounds having at least one arylvinyl group substituted on a substituted or unsubstituted arylamine, and are substituted with one or two or more substituents selected from aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups, or are unsubstituted. Specifically, there are styryl amines, styryl diamines, styryl triamines, styryl tetraamines, and the like, but are not limited thereto. Further, as the metal complexes, there are iridium complexes, platinum complexes, and the like, but are not limited thereto.

[0327] According to an embodiment of the present specification, the above-mentioned dopant material includes a compound represented by the following Chemical Formula D-2, but is not limited thereto.

[0328] According to an embodiment of the present specification, the above-mentioned dopant is represented by a compound of the following Chemical Formula D-2.

[0329] [Chemical Formula D-2]

[0330]

[0331] In the above-mentioned Chemical Formula D-2,

[0332] T1 to T5 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted aryl group,

[0333] t3 and t4 are each an integer of 1 to 4,

[0334] t5 is an integer of 1 to 3,

[0335] when the above-mentioned t3 is 2 or more, the above-mentioned two or more T3s are the same as or different from each other,

[0336] when the above-mentioned t4 is 2 or more, the above-mentioned two or more T4s are the same as or different from each other,

[0337] when the above-mentioned t5 is 2 or more, the above-mentioned two or more T5s are the same as or different from each other.

[0338] According to an embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group having a straight chain or a branched chain of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms.

[0339] According to an embodiment of the present specification, the above T1 to T5 are the same as or different from each other, and each is independently hydrogen, a linear 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 substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0340] According to an embodiment of the present specification, the above T1 to T5 are the same as or different from each other, and each is independently hydrogen, a linear 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 substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0341] According to an embodiment of the present specification, the above chemical formula D-2 is represented by the following compound.

[0342]

[0343] The above electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. When the organic light-emitting device according to an embodiment of the present specification includes an additional electron transport layer in addition to the electron transport layer including the above chemical formula 1, the electron transport substance is a substance that can receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a substance having a large mobility for electrons. As specific examples, there are an Al complex of 8-hydroxyquinoline, a complex including Alq3, an organic radical compound, a hydroxyflavone-metal complex, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode substance as used in the related art. In particular, a suitable cathode substance is a general substance having a low work function with an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like, each with an aluminum layer or a silver layer.

[0344] The above electron injection layer is a layer that receives electrons from the electrode. When the organic light-emitting device according to an embodiment of the present specification includes an additional electron injection layer in addition to the electron injection layer including the above chemical formula 1, as an electron injection substance, a substance having an excellent ability to transport electrons, having an effect of receiving electrons from the second electrode, and having an excellent electron injection effect on the light-emitting layer or the light-emitting material is preferred. In addition, a substance that prevents the migration of excitons generated in the light-emitting layer to the hole injection layer, and has an excellent film formation ability is preferred. Specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

[0345] As the above metal complex compound, there are lithium 8-hydroxyquinoline, zinc bis(8-hydroxyquinoline), copper bis(8-hydroxyquinoline), manganese bis(8-hydroxyquinoline), aluminum tris(8-hydroxyquinoline), aluminum tris(2-methyl-8-hydroxyquinoline), gallium tris(8-hydroxyquinoline), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinoline) chloride, gallium bis(2-methyl-8-quinoline) (o-cresol), aluminum bis(2-methyl-8-quinoline) (1-naphthol), gallium bis(2-methyl-8-quinoline) (2-naphthol), and the like, but are not limited thereto.

[0346] According to an embodiment of the present specification, the above-mentioned electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The above-mentioned electron injection and transport layer material can use a compound represented by the above-mentioned Chemical Formula 1, and when an additional electron injection and transport layer is included in addition to the electron injection and electron transport layer including the above-mentioned Chemical Formula 1, the materials exemplified in the above-mentioned electron transport layer and electron injection layer can be used, but are not limited thereto.

[0347] According to an embodiment of the present specification, the above-mentioned organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the above-mentioned electron injection layer, electron transport layer, or electron injection and transport layer includes the above-mentioned compound. The electron injection layer, electron transport layer, or electron injection and transport layer including the above-mentioned compound further includes a metal or a metal complex compound.

[0348] According to an embodiment of the present specification, the above-mentioned organic layer includes an electron injection and transport layer, and the above-mentioned electron injection and transport layer includes the above-mentioned compound. The electron injection and transport layer including the above-mentioned compound further includes a metal or a metal complex compound.

[0349] According to an embodiment of the present specification, the above-mentioned organic layer includes an electron injection and transport layer, and the above-mentioned electron injection and transport layer includes the above-mentioned compound. The electron injection and transport layer including the above-mentioned compound further includes a metal or a metal complex compound.

[0350] According to an embodiment of the present specification, the above-mentioned compound: metal or metal complex is included in a weight ratio of 1:99 to 99:1, specifically, the above-mentioned compound: metal or metal complex is included in a weight ratio of 10:90 to 90 to 10, more specifically, the above-mentioned compound: metal or metal complex is included in a weight ratio of 50:50.

[0351] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can be formed using the same conditions as the electron injection layer. According to an embodiment of the present specification, an organic light emitting device includes an additional hole blocking layer in addition to the hole blocking layer including the above-described chemical formula 1, specifically, A triazole derivative, a phenanthroline derivative, an aluminum complex, and the like, but is not limited thereto.

[0352] According to an embodiment of the present specification, the hole blocking layer includes a compound of the following chemical formula HB-1.

[0353] [Chemical Formula HB-1]

[0354]

[0355] In the above chemical formula HB-1,

[0356] At least one of Z1 to Z3 is N, and the rest are CH,

[0357] L601 and L602 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

[0358] Ar601 to Ar603 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.

[0359] According to an embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene having 6 to 30 carbon atoms.

[0360] According to an embodiment of the present specification, L601 and L602 are the same as or different from each other, and each is independently a phenylene, a biphenylene, or a naphthylene.

[0361] According to an embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms, or a heteroaryl having 3 to 30 carbon atoms.

[0362] According to an embodiment of the present specification, Ar601 to Ar603 are a phenyl, or a spiro[cyclohexene-1,9'-fluorenyl].

[0363] According to an embodiment of the present specification, the above chemical formula HB-1 is represented by the following compound.

[0364]

[0365] The organic light emitting device according to the present specification can be a top emission type, a bottom emission type, or a bidirectional emission type, depending on the materials used.

[0366] The organic light emitting device according to the present specification can be used in various electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0367] Mode for carrying out the invention

[0368] The organic light emitting device of the present application is formed using the above-mentioned compound in one or more organic layers, and can be manufactured by a general manufacturing method and materials for an organic light emitting device.

[0369] The method for manufacturing the compound of Chemical Formula 1 above and the method for manufacturing the organic light emitting device using the same are specifically described in the following Examples. However, the following Examples are used to illustrate the present application, and the scope of the present application is not limited thereto.

[0370] In the following reaction formula, the type and number of substituents can be synthesized by synthesizing various types of intermediates by appropriately selecting known starting materials by those skilled in the art. The reaction type and reaction conditions can be known in the art.

[0371] Preparation Example 1. Synthesis of Chemical Formula E1

[0372] [Chemical Formula E1]

[0373]

[0374] After completely dissolving the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (10.0 g, 13.8 mmol) and (3-(pyridin-3-yl)phenyl)boronic acid (2.74 g, 13.8 mmol) in tetrahydrofuran (100 ml), potassium carbonate (5.70, 41.3 mmol) was dissolved in 17 ml of water and added, and tetrakis(triphenylphosphine)palladium(0) (477 mg, 0.4 mmol) was dissolved in tetrahydrofuran and slowly introduced. After the temperature was lowered to room temperature, the reaction was completed, the potassium carbonate solution was removed, and the white solid was filtered. The filtered white solid was washed with water and ethyl acetate twice, respectively, thereby manufacturing the compound of Chemical Formula E1 (9.9 g, yield 85%).

[0375] MS [M+H] + = 847

[0376] Preparation Example 2. Chemical Formula E2

[0377] [Chemical Formula E2]

[0378]

[0379] In Production Example 1, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the above compound of Chemical Formula E2 was produced by the same method as the above Production Example 1.

[0380] MS [M+H] + = 847

[0381] Production Example 3. Synthesis of Chemical Formula E3

[0382] [Chemical Formula E3]

[0383]

[0384] In Production Example 1, (4-(pyridin-3-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the above compound of Chemical Formula E3 was produced by the same method as the above Production Example 1.

[0385] MS [M+H] + = 847

[0386] Production Example 4. Synthesis of Chemical Formula E4

[0387] [Chemical Formula E4]

[0388]

[0389] In Production Example 1, (2-(pyridin-3-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the above compound of Chemical Formula E4 was produced by the same method as the above Production Example 1.

[0390] MS [M+H] + = 847

[0391] Production Example 5. Synthesis of Chemical Formula E5

[0392] [Chemical Formula E5]

[0393]

[0394] In Production Example 1, 6,6'-(5'-chloro-[l,l':2',l"-terphenyl]-2,3"- diyl)bis(2,4-diphenyl-l,3,5-triazine) was used instead of the compound 6,6'-(5'- chloro-[l,l':3',l"-terphenyl]-2,2"-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the compound of the above Formula E5 was produced by the same method as Production Example 1 described above, except for this.

[0395] MS [M+H] + = 847

[0396] Production Example 6. Synthesis of Formula E6

[0397] [Formula E6]

[0398]

[0399] In Production Example 5, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and the compound of the above Formula E6 was produced by the same method as Production Example 5 described above, except for this.

[0400] MS [M+H] + = 847

[0401] Production Example 7. Synthesis of Formula E7

[0402] [Formula E7]

[0403]

[0404] In Production Example 1, 6,6'-(4'-chloro-[l,l':2',l"-terphenyl]-2,3"- diyl)bis(2,4-diphenyl-l,3,5-triazine) was used instead of the compound 6,6'-(5'- chloro-[l,l':3',l"-terphenyl]-2,2"-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the compound of the above Formula E7 was produced by the same method as Production Example 1 described above, except for this.

[0405] MS [M+H] + = 847

[0406] Production Example 8. Synthesis of Formula E8

[0407] [Formula E8]

[0408]

[0409] In Production Example 7, (2-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the above compound of Chemical Formula E9 was produced by the same method as the above Production Example 7.

[0410] MS [M+H] + = 847

[0411] Production Example 9. Synthesis of Chemical Formula E9

[0412] [Chemical Formula E9]

[0413]

[0414] In Production Example 7, (2-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the above compound of Chemical Formula E9 was produced by the same method as the above Production Example 7.

[0415] MS [M+H] + = 847

[0416] Production Example 10. Synthesis of Chemical Formula E10

[0417] [Chemical Formula E10]

[0418]

[0419] In Production Example 1, 6,6'-(4'-chloro-[1,1':2',1''-terphenyl]-2,4''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine), and otherwise, the above compound of Chemical Formula E10 was produced by the same method as the above Production Example 1.

[0420] MS [M+H] + = 847

[0421] Production Example 11. Synthesis of Chemical Formula E11

[0422] [Chemical Formula E11]

[0423]

[0424] In Production Example 10, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the above compound of Chemical Formula E11 was produced by the same method as the above Production Example 10.

[0425] MS [M+H] + = 847

[0426] Preparation Example 12. Synthesis of Chemical Formula E12

[0427] [Chemical Formula E12]

[0428]

[0429] In the preparation example 10, (2-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the compound of the above Chemical Formula E12 was manufactured by the same method as the above preparation example 11.

[0430] MS [M+H] + = 847

[0431] Preparation Example 13. Synthesis of Chemical Formula E13

[0432] [Chemical Formula E13]

[0433]

[0434] In the preparation example 1, 6,6'-(3'-chloro-[1,1':4',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine), and otherwise, the compound of the above Chemical Formula E13 was manufactured by the same method as the above preparation example 1.

[0435] MS [M+H] + = 847

[0436] Preparation Example 14. Synthesis of Chemical Formula E14

[0437] [Chemical Formula E14]

[0438]

[0439] In the preparation example 13, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and otherwise, the compound of the above Chemical Formula E14 was manufactured by the same method as the above preparation example 13.

[0440] MS [M+H] + = 847

[0441] Preparation Example 15. Synthesis of Chemical Formula E15

[0442] [Chemical Formula E15]

[0443]

[0444] In Production Example 1, 6,6'-(3'-chloro-[l,l':2',l"-terphenyl]-3,3"- diyl)bis(2,4-diphenyl-l,3,5-triazine) was used instead of compound 6,6'-(5'- chloro-[l,l':3',l"-terphenyl]-2,2"-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the compound of the above Formula E15 was produced by the same method as Production Example 1 described above, except for this.

[0445] MS [M+H] + = 847

[0446] Production Example 16. Synthesis of Formula E16

[0447] [Formula E16]

[0448]

[0449] In Production Example 15, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid, and the compound of the above Formula E16 was produced by the same method as Production Example 15 described above, except for this.

[0450] MS [M+H] + = 847

[0451] Production Example 17. Synthesis of Formula E17

[0452] [Formula E17]

[0453]

[0454] In Production Example 1, 6,6'-(4'-chloro-[l,l':3',l"-terphenyl]-2,3"- diyl)bis(2,4-diphenyl-l,3,5-triazine) was used instead of compound 6,6'-(5'- chloro-[l,l':3',l"-terphenyl]-2,2"-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the compound of the above Formula E17 was produced by the same method as Production Example 1 described above, except for this.

[0455] MS [M+H] + = 847

[0456] Production Example 18. Synthesis of Formula E18

[0457] [Formula E18]

[0458]

[0459] In Production Example 17, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above-mentioned compound (3-(pyridin-3-yl)phenyl)boronic acid, and the above-mentioned compound of Chemical Formula E18 was produced by the same method as in the above-mentioned Production Example 17, except for this.

[0460] MS [M+H] + = 847

[0461] Production Example 19. Synthesis of Chemical Formula E19

[0462] [Chemical Formula E19]

[0463]

[0464] In Production Example 17, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above-mentioned compound (3-(pyridin-3-yl)phenyl)boronic acid, and the above-mentioned compound of Chemical Formula E18 was produced by the same method as in the above-mentioned Production Example 17, except for this.

[0465] MS [M+H] + = 847

[0466] Production Example 20. Synthesis of Chemical Formula E20

[0467] [Chemical Formula E20]

[0468]

[0469] In Production Example 1, 6,6'-(2'-chloro-[l,l':3',l''-terphenyl]-3,3''-diyl)bis(2,4-diphenyl- 1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[l,l':3',l''-terphenyl]-2,2''- diyl)bis(2,4-diphenyl- 1,3,5-triazine), and the above-mentioned compound of Chemical Formula E20 was produced by the same method as in the above-mentioned Production Example 1, except for this.

[0470] MS [M+H] + = 847

[0471] Production Example 21. Synthesis of Chemical Formula E21

[0472] [Chemical Formula E21]

[0473]

[0474] In Production Example 20, (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above-mentioned compound (3-(pyridin-3-yl)phenyl)boronic acid, and the above-mentioned compound of Chemical Formula E21 was produced by the same method as that of the above-mentioned Production Example 20, except for this.

[0475] MS [M+H] + = 847

[0476] Production Example 22. Synthesis of Chemical Formula E22

[0477] [Chemical Formula E22]

[0478]

[0479] In Production Example 1, 6,6'-(5'-chloro-[l,r:3',r'-terphenyl]-2,2"-diyl)bis(2,4- diphenylpyrimidine) was used instead of the compound 6,6'-(5'-chloro-[l,r:3',r'-terphenyl]- 2,2"-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the above-mentioned compound of Chemical Formula E22 was produced by the same method as that of the above-mentioned Production Example 1, except for this.

[0480] MS [M+H] + = 845

[0481] Production Example 23. Synthesis of Chemical Formula E23

[0482] [Chemical Formula E23]

[0483]

[0484] In Production Example 1, 6,6'-(5'-chloro-[l,r:2',r'-terphenyl]-2,3"-diyl)bis(2,4- diphenylpyrimidine) was used instead of the compound 6,6'-(5'-chloro-[l,r:3',r'-terphenyl]- 2,2"-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the above-mentioned compound of Chemical Formula E23 was produced by the same method as that of the above-mentioned Production Example 1, except for this.

[0485] MS [M+H] + = 845

[0486] Production Example 24. Synthesis of Chemical Formula E24

[0487] [Chemical Formula E24]

[0488]

[0489] In Production Example 1, 6,6'-(4'-chloro-[l,l':2',l''-terphenyl]-2,3''-diyl)bis(2,4- diphenylpyrimidine) was used instead of compound 6,6'-(5'-chloro-[l,l':3',l''-terphenyl]- 2,2''-diyl)bis(2,4-diphenyl-l,3,5-triazine), and the compound of the above formula E24 was produced by the same method as Production Example 1 described above, except for this.

[0490] MS [M+H] + =845

[0491] Production Example 25. Synthesis of Formula E25

[0492] [Formula E25]

[0493]

[0494] In Production Example 1, 2-(6'-chloro-3''-(2,6-diphenylpyrimidin-4-yl)- [l,l':2',l''-terphenyl]-3-yl)-4,6-diphenyl-l,3,5-triazine was used instead of compound 6,6'-(5'-chloro-[l,l':3',l''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-l,3,5-triazine), (2- (pyridin-2-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and the compound of the above formula E25 was produced by the same method as Production Example 1 described above, except for this.

[0495] MS [M+H] + =845

[0496] Example 1-1

[0497] A glass substrate on which ITO (indium tin oxide) was coated as a thin film with a thickness of 1000 A was put in distilled water in which a detergent was dissolved, and washed with ultrasonic waves. At this time, the detergent was a product of Fischer Co., and the distilled water was distilled water filtered twice using a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed for 10 minutes using distilled water twice. After the distilled water washing was completed, the substrate was dried after being washed with solvents of isopropyl alcohol, acetone, and methanol using ultrasonic waves. Then, the substrate was put into a plasma cleaning machine. Further, the substrate was cleaned with oxygen plasma for 5 minutes, and then put into a vacuum vapor deposition machine.

[0498] On the ITO transparent electrode prepared as above as an anode, a compound of the following compound HI1 and the following compound HI2 was vacuum-deposited at a thickness of 100 A in a ratio of 98:2 (mole ratio) to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 (1150 A) was vacuum-deposited to form a hole transport layer. Subsequently, on the hole transport layer, a compound of EB1 was vacuum-deposited at a film thickness of 50 A to form an electron suppression layer. Subsequently, on the electron suppression layer, a compound represented by the following formula BH and a compound represented by the following formula BD were vacuum-deposited at a weight ratio of 50:1 at a film thickness of 200 A to form a light-emitting layer. On the light-emitting layer, a compound represented by the following formula HB1 was vacuum-deposited at a film thickness of 50 A to form a hole blocking layer. Subsequently, on the hole blocking layer, a compound of the following formula E1 and a compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer at a thickness of 30 A. On the electron injection and transport layer, lithium fluoride (LiF) was vacuum-deposited at a thickness of 12 A, and aluminum was vacuum-deposited at a thickness of 1000 A to form a cathode.

[0499]

[0500] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 A / sec, and the deposition rate of aluminum was maintained at 2 A / sec. During deposition, the degree of vacuum was maintained at 2 x 10 -7 ~5x10 -6 A to thereby produce an organic light-emitting device.

[0501] Examples 1-2 to 1-24

[0502] An organic light-emitting device was produced in the same manner as in Example 1-1, except that the compound E1 of Example 1 was replaced with the compounds described in Table 1 below.

[0503] Comparative Examples 1-1 to 1-5

[0504] An organic light-emitting device was produced in the same manner as in Example 1-1, except that the compound E1 was replaced with the compounds described in Table 1 below. The compounds ET-1 to ET-5 used in Table 1 below are described below.

[0505]

[0506] When a current was applied to the organic light emitting devices produced according to Examples 1-1 to 1-24 and Comparative Examples 1-1 to 1-5, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 indicates the time required for the luminance to decrease to 95% from the initial luminance (1600 nit).

[0507] [Table 1]

[0508]

[0509] As shown in Table 1 above, when the organic light emitting device was produced using the compound of the present application as the electron transport layer, excellent characteristics were exhibited in the efficiency, driving voltage, and / or stability of the organic light emitting device.

[0510] Compared to the commonly used electron transport layer, by appropriately breaking the conjugation through the appropriate distance between the N-containing ring groups and the linking group connected in the ortho position, the electron injection and mobility were improved, the electron mobility was controlled by increasing the substituent having a heteroaryl group such as pyridine, and thus the lifetime was ensured, and thus low voltage, high efficiency characteristics were exhibited.

[0511] Comparative Example 1-1 used a compound ET-1 in which 3 aryl heteroaryl substituents substituted on the central benzene nucleus were in the same form. Comparative Examples 1-2 and 1-3 used compounds ET-2 and ET-3 in which the N-containing heterocycle was a polycyclic ring.

[0512] Comparative Example 1-4 used a compound ET-4 which did not include a phenylene group substituted with R11, nor a phenyl group substituted with Ar3 and Ar4.

[0513] Comparative Example 1-5 used a compound ET-5 which included only 2 N-containing heterocycles.

[0514] The compounds E1 to E25 of the present application differ in one of the 3 substituents on the benzene nucleus, and the 3 N-containing heterocyclic groups substituted on the nucleus are monocyclic.

[0515] As can be seen in Table 1 above, Examples 1-1 to 1-25 using the compounds E1 to E25 had low voltage, high efficiency, and long lifetime characteristics compared to Comparative Examples 1-1 to 1-5.

[0516] The preferred embodiments (electron transport layer) of the present application were described above, but the present application is not limited thereto, and can be modified in various ways 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 formula 1: [Formula 1] In the formula 1, at least two of X1 to X3 are N, and the rest are CH, at least two of X4 to X6 are N, and the rest are CH, R1 to R11 are the same as or different from each other, and each is independently hydrogen, deuterium, or cyano, r10 is 1 or 2, and when r10 is 2, the two R10s are the same as or different from each other, r11 is an integer of 1 to 4, and when r11 is 2 or more, the two or more R11s are the same as or different from each other, Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, cyano, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, ar1 is an integer of 1 to 5, and when ar1 is 2 or more, the two or more Ar1s are the same as or different from each other, ar2 is an integer of 1 to 5, and when ar2 is 2 or more, the two or more Ar2s are the same as or different from each other, ar3 is an integer of 1 to 5, and when ar3 is 2 or more, the two or more Ar3s are the same as or different from each other, ar4 is an integer of 1 to 5, and when ar4 is 2 or more, the two or more Ar4s are the same as or different from each other, any one or two of Y1 to Y5 is N, and the rest are each independently CR'1, R'1 is hydrogen, deuterium, cyano, or a substituted or unsubstituted alkyl group, or combines with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring. The formula 1 is any one of the following formulas 1-1 to 1-5: [Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4] [Formula 1-5] In the formulas 1-1 to 1-5, the definitions of X1 to X6, Y1 to Y5, R1 to R9, R11, r11, Ar1 to Ar4, and ar1 to ar4 are the same as those in the formula 1, and R101 to R104 are the same as or different from each other, and each is independently hydrogen, deuterium, or cyano. The formula 1 is any one of the following formulas 1-6 to 1-9: [Formula 1-6] [Formula 1-7] [Formula 1-8] [Formula 1-9] In the formulas 1-6 to 1-9, the definitions of X1 to X6, Y1 to Y5, R1 to R11, r10, r11, Ar1 to Ar4, and ar1 to ar4 are the same as those in the formula 1. In the structure, R'11 to R'15 are the same as or different from each other, and each is independently hydrogen, deuterium, cyano, or a substituted or unsubstituted alkyl group, or combines with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring. The definitions of X1 to X6, Ar1 to Ar4, and ar1 to ar4 are the same as those in the formula 1. The definitions of X1 to X6, Ar1 to Ar4, and ar1 to ar4 are the same as those in the formula 1. ​ ​ ​ ​ ​ ​ ​ 2. The compound of claim 1, wherein, ​ ​ ​ ​ ​ ​ ​ ​ ​ 3. The compound of claim 1, wherein, ​ ​ ​ ​ ​ ​ ​ 4. The compound of claim 1, wherein, in Chemical Formula 1 is any one of the following structures: ​ is a site that binds to the chemical formula 1, ​ 5. The compound of claim 1, wherein, The chemical formula 1 in the present application is and different from each other, is a moiety in conjunction with chemical formula 1, ​ 6. The compound of claim 1, wherein, The chemical formula 1 in the present application is and identical to each other, is a site that binds to Chemical Formula 1, ​ 7. The compound of claim 1, wherein, the Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen, deuterium, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, the R'1 is hydrogen, deuterium, a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or combines with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

8. The compound of claim 1, wherein, the Chemical Formula 1 is any one of the following compounds: 。 9. An organic light emitting device, wherein, including: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers comprising the compound according to any one of claims 1 to 8.

10. The organic light emitting device according to claim 9, wherein, the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, the electron injection layer, the electron transport layer, or the electron injection and transport layer comprising the compound.

11. The organic light emitting device of claim 9, wherein, the organic layer comprises a hole blocking layer, the hole blocking layer comprising the compound.

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