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.

Description

Technical Field

[0001] This specification relates to compounds and organic light-emitting devices containing them.

[0002] This application claims priority based on Korean Patent Application No. 10-2024-0003408 filed with the Korean Patent Office on January 9, 2024 and Korean Patent Application No. 10-2024-0173023 filed with the Korean Patent Office on November 28, 2024, the entire contents of which are incorporated herein by reference. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multi-layered structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above.

[0005] Existing technical documents

[0006] (Patent Document 1) U.S. Patent Application Publication No. 2004-0251816 Summary of the Invention

[0007] Technical issues

[0008] This specification provides compounds and organic light-emitting devices containing them.

[0009] Solution to the problem

[0010] One embodiment of this specification provides a compound of the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] Any one or two of Y1 to Y8 are N, any one of the remaining ones is C combined with chemical formula 1, and the rest are CR3 independently.

[0015] X1 is either N or CR'1.

[0016] X2 is either N or CR'2.

[0017] R'1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a moiety combined with L1, or a substituted or unsubstituted aromatic hydrocarbon ring formed by combining with R1.

[0018] R'2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a moiety combined with L2, or combined with R2 to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0019] R1 and R2 may be the same as or different from each other, and each may independently be a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may combine with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0020] R3 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0021] L1 and L2 may be the same or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0022] n1 and n2 are each integers from 1 to 5.

[0023] r1 and r2 are each integers from 1 to 3.

[0024] When n1 is 2 or more, the two or more L1 values ​​are either the same or different from each other.

[0025] When n² is 2 or more, the two or more L² values ​​are either the same or different from each other.

[0026] When r1 is 2 or more, the two or more R1 values ​​are either the same or different from each other.

[0027] When r2 is 2 or more, the two or more R2 values ​​are either the same or different from each other.

[0028] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the aforementioned compound.

[0029] Invention Effects

[0030] The compound according to one embodiment of this specification can be used as a material for the organic layer of an organic light-emitting device. By using the compound, improved efficiency, lower driving voltage, and / or improved lifetime characteristics can be achieved in the organic light-emitting device. Attached Figure Description

[0031] Figure 1 and 2 An example of an organic light-emitting device according to one embodiment of this specification is illustrated.

[0032] [Symbol Explanation]

[0033] 101: Substrate

[0034] 102: First electrode

[0035] 111: Organic layer

[0036] 110: Second electrode

[0037] 103: Hole Injection Layer

[0038] 104: First Hole Transport Layer

[0039] 105: Second Hole Transport Layer

[0040] 106: Emissive layer

[0041] 107: Electron Injection and Transport Layer Detailed Implementation

[0042] The following is a more detailed description of this instruction manual.

[0043] One embodiment of this specification provides a compound of the above-described chemical formula 1.

[0044] According to one embodiment of this specification, chemical formula 1 is a compound having a benzene core with a heterocyclic bicyclic ring containing one or two N atoms, wherein the benzene core must contain arylene groups as linking groups and heteroarylene groups containing two or three N atoms as substituents. Since this compound has an electron-depleted structure, the polarity (dipole moment) of the molecule can be increased. Therefore, when fabricating an organic light-emitting device containing the compound represented by the above chemical formula 1, the electron mobility can be smoothly adjusted, and the organic light-emitting device containing it has the effects of low voltage, high efficiency and long lifetime.

[0045] Throughout this application, the term "combination of them" in the Markush form of the description refers to a mixture or combination of one or more of the constituent elements described in the Markush form of the description, and means including one or more of the constituent elements mentioned above.

[0046] Examples of substituents in this specification are described below, but are not limited thereto.

[0047] In this instruction manual, Indicates the part that is connected.

[0048] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0049] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen group, cyano, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, boron, amino, aryl, and heteroaryl, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0050] In this specification, the connection of two or more substituents refers to the connection of the hydrogen of any one substituent with other substituents. For example, the connection of two substituents can be achieved by connecting a phenyl group and a naphthyl group to form... or Such substituents. Furthermore, the connection of three substituents not only includes a sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also includes (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... , or Such substituents. The above definition also applies to connections of four or more substituents.

[0051] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine groups.

[0052] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0053] In this specification, cycloalkyl groups are not particularly limited, but preferably cycloalkyl groups with 3 to 30 carbon atoms. Specifically, they include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited to these.

[0054] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 30. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0055] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0056] In this specification, the above-mentioned haloalkyl means that the hydrogen of the alkyl group is replaced by at least one halogen group in place of the alkyl group defined above.

[0057] In this specification, aryl is not particularly limited, but is preferably an aryl with 6 to 30 carbon atoms, and the aryl can be monocyclic or polycyclic.

[0058] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 6 to 30 carbon atoms. Specifically, the monocyclic aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited to these.

[0059] When the aryl group mentioned above is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group can be naphthyl, anthraceneyl, phenanthrene, phenylene, pyrene, beryl, peryl, alkyl, fluorene, etc., but is not limited to these.

[0060] In this specification, the fluorene group can be substituted, and adjacent groups can combine with each other to form a ring.

[0061] When the aforementioned fluorene group is replaced, there is etc., but not limited to this.

[0062] In this specification, "adjacent" groups can refer to substituents that are substituted on an atom directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0063] In this specification, a heteroaryl group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, P, Si, and S. The number of carbon atoms in the heteroaryl group is not particularly limited, but preferably 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furanyl, pyrroleyl, imidazolyl, and thiazolyl. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthroline, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol (phenoxathiine), phen Phenoxazine, phenothiazine, dihydroindocarbazolyl, spirofluorenylxanthinyl, and spirofluorenylthioxanthinyl are examples, but not limited to these.

[0064] In this specification, the aforementioned silane group can be alkylsilane, arylsilane, heteroarylsilane, etc. The alkyl group in the aforementioned alkylsilane can be an example of the aforementioned alkyl group, the aryl group in the aforementioned arylsilane can be an example of the aforementioned aryl group, and the heteroaryl group in the aforementioned heteroarylsilane can be an example of the aforementioned heterocyclic group.

[0065] In this specification, the boron group can be -BG. 100 G 101 The above G 100 and G 101 These groups may be identical or different from each other, and each can be independently selected from hydrogen, deuterium, halogen, nitrile, cyclic alkyl groups with 3 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic), straight-chain or branched alkyl groups with 1 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic), aryl groups with 6 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic), and heteroaryl groups with 2 to 30 substituted or unsubstituted carbon atoms (monocyclic or polycyclic). Specific examples of the aforementioned boryl groups include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but are not limited to these.

[0066] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino, and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited to these.

[0067] In this specification, N-alkylarylamine refers to an amino group in which an alkyl or aryl group is substituted for the N group. The alkyl and aryl groups in the above-described N-alkylarylamine are the same as those exemplified above.

[0068] In this specification, N-arylheteroarylamine refers to an amino group in which an aryl or heteroaryl group is substituted at the N atom of the amino group. The aryl and heteroaryl groups in the above-described N-arylheteroarylamine are the same as those exemplified above.

[0069] In this specification, N-alkylheteroarylamine refers to an amino group in which the N group is substituted with an alkyl or heteroaryl group. The alkyl and heteroaryl groups in the above-described N-alkylheteroarylamine are the same as those exemplified above.

[0070] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups and substituted or unsubstituted diarylamine groups. Arylamine groups containing two or more of the above-described aryl groups may include monocyclic aryl, polycyclic aryl, or both monocyclic and polycyclic aryl groups. For example, the aryl groups in the above-described arylamine groups may be selected from the examples of the aryl groups described above.

[0071] In this specification, examples of heteroarylamines include substituted or unsubstituted mono-heteroarylamines and substituted or unsubstituted di-heteroarylamines. Heteroarylamines containing two or more of the above-described heteroaryl groups may include monocyclic heteroaryl, polycyclic heteroaryl, or may simultaneously contain both monocyclic and polycyclic heteroaryl groups. For example, the heteroaryl groups in the above-described heteroarylamines may be selected from the examples of heteroaryl groups described above.

[0072] In this specification, alkyl thio ( ) and alkylsulfonyl ( The alkyl group in ) is the same as the alkyl group mentioned above. Specifically, as alkyl thio groups, there are methyl thio, ethyl thio, tert-butyl thio, hexyl thio, octyl thio, etc., and as alkyl sulfonyl groups, there are methyl sulfonyl, ethyl sulfonyl, propyl sulfonyl, butyl sulfonyl, etc., but it is not limited to these.

[0073] In this specification, the phosphorus oxide group specifically includes alkyl phosphorus oxide group, aryl phosphorus oxide group, etc., and more specifically, diphenyl phosphorus oxide group, dinaphthyl phosphorus oxide group, etc., but is not limited to these.

[0074] In this specification, aryloxy and arylthio groups ( ), arylsulfonyl ( The aryl groups in arylphosphine and arylphosphine are the same as those exemplified above. Specifically, as aryloxy groups, there are phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, 9-phenanthoxy, etc.; as arylthio groups, there are phenylthio, 2-tolylthio, 4-tert-butylphenylthio, etc.; and as arylsulfonyl groups, there are phenylsulfonyl, p-tolylsulfonyl, etc., but they are not limited to these.

[0075] In this specification, "adjacent groups combine with each other to form a ring" in the context of substituents means that they combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0076] In this specification, in the context of substituted or unsubstituted rings formed by their combination, "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0077] In this 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 examples of the above-mentioned cycloalkyl or aryl groups, except that it is not monovalent as described above.

[0078] In this specification, a heterocycle comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds. The aromatic heterocycles may be selected from the examples of the heteroaryl groups mentioned above, except that they are not monovalent.

[0079] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepane ( ), aziridine ( ), Thioctane ( (etc.), but not limited to this.

[0080] In this specification, arylene refers to a group with two bonding sites on an aryl group, i.e., a divalent group. Apart from being divalent groups themselves, they are subject to the above description of aryl groups.

[0081] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar to or equivalent to those described herein may be used for implementation or testing of embodiments of the invention, but suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification, including definitions, takes precedence unless otherwise specified. Furthermore, materials, methods, and embodiments are illustrative and not intended to be limiting.

[0082] The compounds represented by the above chemical formula 1 will now be described in detail.

[0083] According to one embodiment of this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6.

[0084] [Chemical Formula 1-1]

[0085]

[0086] [Chemical Formula 1-2]

[0087]

[0088] [Chemical Formulas 1-3]

[0089]

[0090] [Chemical Formulas 1-4]

[0091]

[0092] [Chemical Formulas 1-5]

[0093]

[0094] [Chemical Formulas 1-6]

[0095]

[0096] In the above chemical formulas 1-1 to 1-6,

[0097] The definitions of Y1 to Y8, X1, X2, R1, R2, r1, r2, L1, L2, n1, and n2 are the same as those in Chemical Formula 1 above.

[0098] According to one embodiment of this specification, the above-mentioned chemical formula 1 is chemical formula 1-7 or 1-8.

[0099] [Chemical Formulas 1-7]

[0100]

[0101] [Chemical Formulas 1-8]

[0102]

[0103] In the above chemical formulas 1-7 and 1-8,

[0104] The definitions of Y1 to Y8, X1, X2, R1, R2, r1, r2, L1, L2, n1, and n2 are the same as those in Chemical Formula 1 above.

[0105] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 is N, and Y2 to Y7 are each independently CR3.

[0106] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y2 is N, and Y1 and Y3 to Y7 are each independently CR3.

[0107] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y3 is N, and Y1, Y2, and Y4 to Y7 are each independently CR3.

[0108] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y4 is N, and Y1 to Y3 and Y5 to Y7 are each independently CR3.

[0109] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y5 is N, and Y1 to Y4, Y6 and Y7 are each independently CR3.

[0110] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y6 is N, and Y1 to Y5 and Y7 are each independently CR3.

[0111] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y7 is N, and Y1 to Y6 are each independently CR3.

[0112] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 and Y2 are N, and Y3 to Y7 are each independently CR3.

[0113] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 and Y3 are N, and Y2 and Y4 to Y7 are each independently CR3.

[0114] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 and Y4 are N, and Y2, Y3 and Y5 to Y7 are each independently CR3.

[0115] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 and Y5 are N, and Y2 to Y4, Y6 and Y7 are each independently CR3.

[0116] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 and Y6 are N, and Y2 to Y5 and Y7 are each independently CR3.

[0117] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y1 and Y7 are N, and Y2 to Y6 are each independently CR3.

[0118] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y2 and Y3 are N, and Y1 and Y4 to Y7 are each independently CR3.

[0119] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y2 and Y4 are N, and Y1, Y3 and Y5 to Y7 are each independently CR3.

[0120] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y2 and Y5 are N, and Y1, Y3, Y4, Y6 and Y7 are each independently CR3.

[0121] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y2 and Y6 are N, and Y1, Y3 to Y5 and Y7 are each independently CR3.

[0122] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y2 and Y7 are N, and Y1 and Y3 to Y6 are each independently CR3.

[0123] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y3 and Y4 are N, and Y1, Y2 and Y5 to Y7 are each independently CR3.

[0124] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y3 and Y5 are N, and Y1, Y2, Y4, Y6 and Y7 are each independently CR3.

[0125] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y3 and Y6 are N, and Y1, Y2, Y4, Y5 and Y7 are each independently CR3.

[0126] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y3 and Y7 are N, and Y1, Y2 and Y4 to Y6 are each independently CR3.

[0127] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y4 and Y5 are N, and Y1 to Y3, Y6 and Y7 are each independently CR3.

[0128] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y4 and Y6 are N, and Y1 to Y3, Y5 and Y7 are each independently CR3.

[0129] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y4 and Y7 are N, and Y1 to Y3, Y5 and Y6 are each independently CR3.

[0130] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y5 and Y6 are N, and Y1 to Y4, Y6 and Y7 are each independently CR3.

[0131] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y5 and Y6 are N, and Y1 to Y4 and Y6 are each independently CR3.

[0132] According to one embodiment of this specification, Y8 is C combined with chemical formula 1, Y6 and Y7 are N, and Y1 to Y5 are each independently CR3.

[0133] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 is N, and Y3 to Y8 are each independently CR3.

[0134] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y3 is N, and Y2 and Y4 to Y8 are each independently CR3.

[0135] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y4 is N, and Y2, Y3, and Y5 to Y8 are each independently CR3.

[0136] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y5 is N, and Y2 to Y4 and Y6 to Y8 are each independently CR3.

[0137] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y6 is N, and Y2 to Y5, Y7 and Y8 are each independently CR3.

[0138] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y7 is N, and Y2 to Y6 and Y8 are each independently CR3.

[0139] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y8 is N, and Y2 to Y7 are each independently CR3.

[0140] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 and Y3 are N, and Y4 to Y8 are each independently CR3.

[0141] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 and Y4 are N, and Y3 and Y5 to Y8 are each independently CR3.

[0142] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 and Y5 are N, and Y4 and Y6 to Y8 are each independently CR3.

[0143] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 and Y6 are N, and Y3 to Y5, Y7 and Y8 are each independently CR3.

[0144] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 and Y7 are N, and Y3 to Y6 and Y8 are each independently CR3.

[0145] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y2 and Y8 are N, and Y3 to Y7 are each independently CR3.

[0146] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y3 and Y4 are N, and Y2 and Y5 to Y8 are each independently CR3.

[0147] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y3 and Y5 are N, and Y2, Y4 and Y6 to Y8 are each independently CR3.

[0148] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y3 and Y6 are N, and Y2, Y4, Y5, Y7 and Y8 are each independently CR3.

[0149] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y3 and Y7 are N, and Y2, Y4 to Y6 and Y8 are each independently CR3.

[0150] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y3 and Y8 are N, and Y2 and Y4 to Y7 are each independently CR3.

[0151] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y4 and Y5 are N, and Y2, Y3 and Y6 to Y8 are each independently CR3.

[0152] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y6 and Y7 are N, and Y1, Y2, Y3, Y5 and Y7 are each independently CR3.

[0153] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y4 and Y7 are N, and Y2, Y3, Y5, Y6 and Y8 are each independently CR3.

[0154] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y4 and Y8 are N, and Y2, Y3 and Y5 to Y7 are each independently CR3.

[0155] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y5 and Y6 are N, and Y2 to Y4, Y7 and Y8 are each independently CR3.

[0156] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y5 and Y7 are N, and Y2 to Y5, Y6 and Y8 are each independently CR3.

[0157] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y5 and Y8 are N, and Y2 to Y4, Y6 and Y7 are each independently CR3.

[0158] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y6 and Y7 are N, and Y2 to Y5, Y7 and Y8 are each independently CR3.

[0159] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y6 and Y8 are N, and Y2 to Y5 and Y7 are each independently CR3.

[0160] According to one embodiment of this specification, Y1 is C combined with chemical formula 1, Y7 and Y8 are N, and Y2 to Y6 are each independently CR3.

[0161] According to one embodiment of this specification, the above-described chemical formula 1... It can be any of the following structural formulas.

[0162]

[0163]

[0164] In the above structure,

[0165] This indicates the site where it combines with chemical formula 1 above.

[0166] R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or substituted or unsubstituted alkyl.

[0167] According to one embodiment of this specification, X1 is N or CR'1.

[0168] According to another embodiment of this specification, R'1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0169] According to another embodiment of this specification, R'1 is hydrogen.

[0170] According to another embodiment of this specification, R'1 is the portion that is combined with L1.

[0171] According to another embodiment of this specification, R'1 and R1 combine to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0172] According to another embodiment of this specification, the above-mentioned R'1 and R1 combine to form a monocyclic or polycyclic aromatic hydrocarbon ring with 2 to 30 substituted or unsubstituted carbon atoms.

[0173] According to another embodiment of this specification, R'1 is combined with R1 to form substituted or unsubstituted benzene.

[0174] According to one embodiment of this specification, X2 is N or CR'1.

[0175] According to another embodiment of this specification, R'2 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0176] According to another embodiment of this specification, R'2 is hydrogen.

[0177] According to another embodiment of this specification, R'2 is the portion that is combined with L2.

[0178] According to another embodiment of this specification, the above-mentioned R'2 combines with R2 to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0179] According to another embodiment of this specification, the above-mentioned R'2 combines with R2 to form a monocyclic or polycyclic aromatic hydrocarbon ring with 2 to 30 substituted or unsubstituted carbon atoms.

[0180] According to another embodiment of this specification, the above-mentioned R'2 combines with R2 to form substituted or unsubstituted benzene.

[0181] According to one embodiment of this specification, n1 is 1.

[0182] According to one embodiment of this specification, n1 is 2.

[0183] According to one embodiment of this specification, n1 is 3.

[0184] In this specification, when n1 is 2 or more in the above chemical formula 1, it means that two or more L1s are the same or different from each other, and that each L1 is connected in series. For example, when n1 is 3, and each L1 is phenylene, naphthylene, and phenylene, they can be connected as shown below, but are not limited thereto, and the order or connection position of each L1 can be different.

[0185]

[0186] In addition, for example, the above This indicates that when n1 is 3, it combines with the terminal substituent, i.e., the phenylene group, located at the third position in the structure illustrated above. This indicates the site where it combines with chemical formula 1 above. This indicates the location where the L1 ends.

[0187] The same applies to the explanation of n2 as to n1.

[0188] According to one embodiment of this specification, n2 is 1.

[0189] According to one embodiment of this specification, n2 is 2.

[0190] According to one embodiment of this specification, n2 is 3.

[0191] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0192] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 substituted or unsubstituted carbon atoms.

[0193] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 20 substituted or unsubstituted carbon atoms.

[0194] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 10 substituted or unsubstituted carbon atoms.

[0195] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently an aryl group.

[0196] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0197] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0198] According to one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

[0199] According to one embodiment of this specification, L1 and L2 are phenylene oxides.

[0200] According to one embodiment of this specification, L1, L2, and L3 are connected to the central phenyl (benzene ring) of the above-described chemical formula 1. Two of them are located in the ortho orientation.

[0201] According to one embodiment of this specification, the above-mentioned chemical formula 1 is the following chemical formula 2.

[0202] [Chemical Formula 2]

[0203]

[0204] In the above chemical formula 2,

[0205] The definitions of Y1 to Y8, X1, X2, R1, R2, r1, and r2 are the same as those in Chemical Formula 1 above.

[0206] In one embodiment of this specification, in the above chemical formula 2, the phenylene (rings 2 and 3) connected to the central phenyl group (ring 1 below) and The two phenyl groups in the center (ring 1 below) are ortho-oriented.

[0207]

[0208] According to one embodiment of this specification, the above-described chemical formula 1... It is selected from any of the following structures.

[0209]

[0210] In the above structure,

[0211] For the site where it combines with chemical formula 1,

[0212] The definitions of L1, n1, R1, r1, and R'1 are the same as those in Chemical Formula 1 above.

[0213] R101 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0214] r101 is an integer from 1 to 4.

[0215] When r101 is 2 or more, the two or more R101 are the same or different from each other.

[0216] According to one embodiment of this specification, the above-described chemical formula 1... It is selected from any of the following structures.

[0217]

[0218] In the above structure,

[0219] For the site where it combines with chemical formula 1,

[0220] The definitions of L2, n2, R2, r2, and R'2 are the same as those in Chemical Formula 1 above.

[0221] R201 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0222] R201 is an integer from 1 to 4.

[0223] When there are 2 or more r201, the two or more R201 are the same or different from each other.

[0224] According to one embodiment of this specification, the above-described chemical formula 1... and They are the same.

[0225] According to one embodiment of this specification, the above-described chemical formula 1... and They are different from each other.

[0226] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently represents a monocyclic or polycyclic alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0227] R'1 is hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a moiety combined with L1.

[0228] The aforementioned R'2 is hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a moiety combined with L2.

[0229] The L1 and L2 mentioned above may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 carbon atoms.

[0230] R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0231] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0232] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0233] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group with 2 to 20 substituted or unsubstituted carbon atoms.

[0234] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is a monocyclic or polycyclic alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 1 to 30 carbon atoms, a monocyclic or polycyclic alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 2 to 30 carbon atoms.

[0235] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0236] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; biphenyl; naphthyl; or a pyridyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0237] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms; biphenyl; naphthyl; or a pyridyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0238] According to one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with methyl, tert-butyl, cyclohexyl, or pyridyl group substituted or unsubstituted with methyl; biphenyl; naphthyl; or pyridyl group substituted or unsubstituted with methyl or phenyl.

[0239] According to one embodiment of this specification, one of the R1s is a portion that is bonded to L1, and the remaining R1s are the substituents described above.

[0240] According to one embodiment of this specification, one of the R2 is a portion that is bonded to L2, and the remaining R2 are the substituents described above.

[0241] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0242] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0243] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, whether substituted or unsubstituted.

[0244] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 10 carbon atoms, whether substituted or unsubstituted.

[0245] According to one embodiment of this specification, R3 is hydrogen, deuterium, or alkyl.

[0246] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0247] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms.

[0248] According to one embodiment of this specification, R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 10 carbon atoms.

[0249] According to one embodiment of this specification, R3 is hydrogen, deuterium, or methyl.

[0250] According to one embodiment of this specification, one of the R3 is a portion that is bonded to the phenyl (benzene ring) of Formula 1, and the remaining R3 are the substituents described above.

[0251] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0252] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0253] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, whether substituted or unsubstituted.

[0254] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 10 carbon atoms, whether substituted or unsubstituted.

[0255] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium or alkyl.

[0256] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0257] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms.

[0258] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 10 carbon atoms.

[0259] According to one embodiment of this specification, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium or methyl.

[0260] According to one embodiment of this specification, the above-mentioned chemical formula 1 is any one of the following compounds.

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286] One embodiment of this specification provides an organic light-emitting device comprising a compound represented by the above chemical formula 1.

[0287] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0288] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0289] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. According to one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0290] In this specification, the meaning of a specific substance A being contained in layer B includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are contained in one or more layers of multiple layers of layer B.

[0291] In this specification, the meaning of a specific substance A being contained in layer C or layer D is all of the following: i) contained in one or more layers of layer C, or ii) contained in one or more layers of layer D, or iii) contained in one or more layers of layer C and one or more layers of layer D respectively.

[0292] This specification provides an organic light-emitting device, comprising: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound represented by the above chemical formula 1.

[0293] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. 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 blocking layer, and a hole blocking layer. However, the structure of the organic light-emitting device is not limited to this and can include fewer organic layers.

[0294] According to one embodiment of this specification, the organic layer includes an electron transport region between the light-emitting layer and the second electrode, and the electron transport region contains the aforementioned compound. The electron transport region may include one or more of the following: an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer.

[0295] According to one embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, electron transport layer, or electron injection and transport layer contains the aforementioned compound.

[0296] According to one embodiment of this specification, the organic layer includes a hole-blocking layer, and the hole-blocking layer contains the aforementioned compound.

[0297] According to one embodiment of this specification, in addition to the compound of chemical formula 1, the electron transport region also contains one or more n-type dopants selected from alkali metals and alkaline earth metals.

[0298] When organoalkali metal compounds or organoalkaline earth metal compounds are used as n-type dopants, they can ensure the stability of holes from the emissive layer, thereby improving the lifetime of organic light-emitting devices. Furthermore, the electron mobility of the electron transport layer and the ratio of organoalkali metal compounds or organoalkaline earth metal compounds can be adjusted to maximize the balance of holes and electrons in the emissive layer, thereby increasing luminous efficiency.

[0299] According to one embodiment of this specification, n-type dopants include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these. According to one embodiment, LiQ is more preferably used as an n-type dopant.

[0300] According to one embodiment of this specification, in the electron transport region, the compound of Formula 1 and the n-type dopant are contained in the same organic layer. Alternatively, the electron transport region may comprise two or more adjacent organic layers, each of which may be formed solely of the compound of Formula 1 or the n-type dopant.

[0301] According to one embodiment of this specification, in the above-mentioned electron transport region, the compound of chemical formula 1 and the n-type dopant may be contained in a weight ratio of 2:8 to 8:2, preferably 3:7 to 7:3, and more preferably 4:6 to 6:4.

[0302] According to one embodiment of this specification, the organic layer includes a light-emitting layer.

[0303] According to one embodiment of this specification, the aforementioned organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0304] According to one embodiment of this specification, the organic layer includes an electron blocking layer.

[0305] According to one embodiment of this specification, the organic layer includes a hole-blocking layer.

[0306] According to one embodiment of this specification, the above-mentioned organic light-emitting device further includes one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, light-emitting layer, electron transport layer, electron injection layer, electron injection and transport layer, hole blocking layer, and electron blocking layer.

[0307] According to one embodiment of this specification, the organic light-emitting device 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 two or more organic layers disposed between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0308] According to one embodiment of this specification, the two or more organic layers mentioned above may be selected from two or more of the following: hole injection layer, hole transport layer, hole injection and transport layer, light emission layer, electron transport layer, electron injection layer, electron injection and transport layer, hole blocking layer, and electron blocking layer.

[0309] According to one embodiment of this specification, the light-emitting layer and the first electrode include two or more hole transport layers. These two or more hole transport layers may contain the same or different materials.

[0310] According to one embodiment of this specification, the first electrode is an anode or a cathode.

[0311] According to one embodiment of this specification, the second electrode is a cathode or an anode.

[0312] According to one embodiment of this specification, the above-mentioned organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0313] According to one embodiment of this specification, the organic light-emitting device can be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0314] For example, the structure of an organic light-emitting device according to one embodiment of this specification is illustrated in... Figure 1 and Figure 2 The above. Figure 1 and Figure 2 Organic light-emitting devices are illustrated, but are not limited to them.

[0315] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 102, an organic layer 111, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above-described chemical formula 1 is contained within the organic layer.

[0316] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 102, a hole injection layer 103, a first hole transport layer 104, a second hole transport layer 105, a light-emitting layer 106, an electron injection and transport layer 107, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above-described chemical formula 1 is contained in the electron injection and transport layer.

[0317] In the organic light-emitting devices described in this specification, the electron injection layer, electron transport layer, electron injection and transport layer, or hole blocking layer comprises the aforementioned compound, i.e., the compound represented by the aforementioned chemical formula 1, or otherwise, can be manufactured using materials and methods known in the art.

[0318] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0319] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0320] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0321] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to these methods.

[0322] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited to these.

[0323] As the cathode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0324] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include dibenzofuran derivatives and ladder-type furan compounds. ), pyrimidine derivatives, etc., but not limited to these.

[0325] According to one embodiment of this specification, the above-mentioned body comprises, but is not limited to, a compound represented by the following chemical formula H-1.

[0326] [Chemical formula H-1]

[0327]

[0328] In the above chemical formula H-1,

[0329] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0330] Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0331] R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0332] r201 is an integer from 1 to 8. When r201 is 2 or more, two or more r201s are the same or different from each other.

[0333] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, or a divalent heterocyclic group with 2 to 30 carbon atoms.

[0334] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or substituted naphthylene, divalent dibenzofuranyl, or divalent dibenzothiopheneyl.

[0335] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that has been substituted or unsubstituted, or a monocyclic or polycyclic heterocyclic group with 2 to 30 carbon atoms that has been substituted or unsubstituted.

[0336] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic to tetracyclic aryl group with 6 to 20 carbon atoms, substituted or unsubstituted, or a monocyclic to tetracyclic heterocyclic group with 6 to 20 carbon atoms.

[0337] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. The aryl-substituted or unsubstituted thiophene group; the dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; the naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; the dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or the naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0338] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each independently represents a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a terphenyl, a deuterated or unsubstituted naphthyl, a phenyl-substituted or unsubstituted thiophene, a dibenzofuranyl, a naphthobenzofuranyl, a dibenzothiophene, or a naphthobenzothiophene.

[0339] In one embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0340] According to one embodiment of this specification, R201 is hydrogen or phenyl.

[0341] According to one embodiment of this specification, the above chemical formula H-1 is represented by the following compound.

[0342]

[0343] As dopant materials, there are aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives having substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, benzo[a]pyrene, and diind[b]pyrene. Furthermore, styrene amine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted aryl amine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrene amines, styrene diamines, styrene triamines, and styrene tetraamines, but these are not limited to these. Furthermore, as metal complexes, there are iridium complexes, platinum complexes, etc., but these are not limited to these.

[0344] According to one embodiment of this specification, the dopant comprises, but is not limited to, a compound represented by the following chemical formula D-1.

[0345] [Chemical Formula D-1]

[0346]

[0347] In the above chemical formula D-1,

[0348] T1 to T6 may be the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkylsilyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0349] t5 and t6 are each integers from 1 to 4.

[0350] When t5 is 2 or more, the two or more T5 values ​​are either the same or different from each other.

[0351] When t6 is 2 or more, the two or more T6 are the same or different from each other.

[0352] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each independently comprises hydrogen, a straight-chain or branched alkyl group having 1 to 30 substituted or unsubstituted carbon atoms, a straight-chain or branched alkylsilyl group having 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 substituted or unsubstituted carbon atoms.

[0353] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen; a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, cyano, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0354] According to one embodiment of this specification, T1 to T6 may be the same as or different from each other, and each is independently hydrogen, isopropyl, trimethylsilyl, deuterium-substituted phenyl, cyano-substituted phenyl, or methyl-substituted phenyl.

[0355] According to one embodiment of this specification, the above chemical formula D-1 is represented by the following compound.

[0356]

[0357] The aforementioned hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, the effect of receiving holes from the anode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material is preferred. Moreover, a material with excellent thin film forming ability is preferred. Furthermore, the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between that of the work function of the anode material and that of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds; hexanitrile hexaazabenzophenanthrene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; anthraquinones, polyaniline, and polythiophene-based conductive polymers.

[0358] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HI-1.

[0359] [Chemical formula HI-1]

[0360]

[0361] In the above chemical formula HI-1,

[0362] R301 to R306 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0363] L301 and L302 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0364] According to one embodiment of this specification, R301 and R302 may be the same as or different from each other, and each is independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0365] According to one embodiment of this specification, R301 and R302 are methyl groups.

[0366] According to one embodiment of this specification, L301 and L302 are directly bonded.

[0367] According to one embodiment of this specification, R303 to R306 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0368] According to one embodiment of this specification, R303 to R306 may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 30 carbon atoms substituted or unsubstituted by a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms.

[0369] According to one embodiment of this specification, R303 to R306 may be the same as or different from each other, and each is independently a phenyl group, or a carbazolyl group substituted with or unsubstituted with a phenyl group.

[0370] According to one embodiment of this specification, the above chemical formula HI-1 is represented by the following compound.

[0371]

[0372] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; preferably, it is a substance with a high hole mobility. Specific examples include arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0373] According to one embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound represented by the chemical formula HT-1.

[0374] [Chemical formula HT-1]

[0375]

[0376] In the above chemical formula HT-1,

[0377] At least one of X'1 to X'6 is N, and the rest are CH.

[0378] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0379] According to one embodiment of this specification, X'1 to X'6 are N.

[0380] According to one embodiment of this specification, R309 to R314 are cyano groups.

[0381] According to one embodiment of this specification, the above-mentioned chemical formula HT-1 is represented by the following compound.

[0382]

[0383] According to one embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound represented by the chemical formula HT-2.

[0384] [Chemical formula HT-2]

[0385]

[0386] In the above chemical formula HT-2,

[0387] R315 to R317 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0388] r315 is an integer from 1 to 5. When r315 is 2 or more, two or more of the above R315 are either the same or different from each other.

[0389] r316 is an integer from 1 to 5. When r316 is 2 or more, two or more of the above R316 are the same or different from each other.

[0390] According to one embodiment of this specification, R317 is selected from any one of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, and combinations thereof.

[0391] According to one embodiment of this specification, R317 is selected from carbazolyl, phenyl, biphenyl, and combinations thereof.

[0392] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently a substituted or unsubstituted aryl group, or combined with adjacent groups to form an alkyl-substituted aromatic hydrocarbon ring.

[0393] According to one embodiment of this specification, R315 and R316 may be the same as or different from each other, each being independently phenyl, or combined with adjacent groups to form an indenyl group substituted with methyl.

[0394] According to one embodiment of this specification, the above-mentioned chemical formula HT-2 is represented by the following compound.

[0395]

[0396] The aforementioned electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. When an organic light-emitting device according to one embodiment of this specification includes an additional electron transport layer besides the electron transport layer comprising the aforementioned chemical formula 1, the electron transport material is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, preferably a material with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are generally materials with low work functions and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, etc., are all accompanied by an aluminum or silver layer in each case.

[0397] The aforementioned electron injection layer is a layer that receives electrons from the electrode. When an organic light-emitting device according to one embodiment of this specification includes an additional electron injection layer besides the electron injection layer comprising the aforementioned chemical formula 1, the preferred electron injection material is one that has excellent electron transport capabilities, effectively receives electrons from the second electrode, and has excellent electron injection effects on the light-emitting layer or light-emitting material. Furthermore, it is preferable to use a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin-film formation capabilities. Specifically, this includes fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0398] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0399] According to one embodiment of this specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer material may be a compound represented by the above-described chemical formula 1. When additional electron injection and transport layers besides the electron injection and electron transport layer containing the above-described chemical formula 1 are used, the materials exemplified in the electron transport layer and electron injection layer may be used, but this is not a limitation.

[0400] According to one embodiment of this specification, the aforementioned organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, electron transport layer, or electron injection and transport layer contains the aforementioned compound. The electron injection layer, electron transport layer, or electron injection and transport layer containing the aforementioned compound further contains a metal, or a metal coordination compound.

[0401] According to one embodiment of this specification, the organic layer includes an electron injection and transport layer, which contains the aforementioned compound. The electron injection and transport layer containing the aforementioned compound further contains a metal or a metal coordination compound.

[0402] According to one embodiment of this specification, the organic layer includes an electron injection and transport layer, which contains the aforementioned compound. The electron injection and transport layer containing the aforementioned compound further contains a metal coordination compound.

[0403] The aforementioned metals or metal coordination compounds can be made from materials as described above.

[0404] According to one embodiment of this specification, the above-mentioned compound: metal or metal complex is contained in a weight ratio of 1:99 to 99:1, specifically, in a weight ratio of 10:90 to 90 to 10, and more specifically, in a weight ratio of 50:50.

[0405] The aforementioned electron blocking layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the device's lifetime and efficiency. It can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport, without limitation using known materials.

[0406] The hole blocking layer described above is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the electron injection layer. In an organic light-emitting device according to one embodiment of this specification, when it includes an additional hole blocking layer besides the hole blocking layer comprising the aforementioned chemical formula 1, specifically, there is... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0407] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0408] The organic light-emitting device according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0409] Methods of implementing the invention

[0410] Hereinafter, in order to provide a detailed description of this specification, embodiments and comparative examples will be given. However, various modifications can be made based on the embodiments and comparative examples described herein, and this should not be construed as limiting the scope of this specification to the embodiments and comparative examples detailed below. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0411] Manufacturing Example 1.

[0412]

[0413] 2-Bromo-1-chloro-3-iodobenzene (9.52 g, 30 mmol) and isoquinolin-1-ylboronic acid (5.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K₂CO₃ (200 mL) and tetrakis(triphenylphosphine)palladium(O) (0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 1-1.

[0414] Compounds 1-1 (9.6 g, 30 mmol) and 1-2 (11.66 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compounds 1-3.

[0415] Compounds 1-3 (16.41 g, 30 mmol) and 1-4 (11.66 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL), palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 1.

[0416] (19.68g, yield 80%, MS: [M+H]) + =820).

[0417] Manufacturing Example 2.

[0418]

[0419] The starting materials were used as described in the above reaction formula, except that the above compound 2 was manufactured by the same method as that used in manufacturing example 1.

[0420] MS:[M+H] + =897

[0421] Manufacturing Example 3.

[0422]

[0423] The starting materials were used as described in the above reaction formula, except that the above compound 3 was manufactured by the same method as that used in manufacturing example 1.

[0424] MS:[M+H] + =897

[0425] Manufacturing Example 4.

[0426]

[0427] The starting materials were used as described in the above reaction formula, except that the above compound 4 was manufactured by the same method as that used in manufacturing example 1.

[0428] MS:[M+H] + =834

[0429] Manufacturing Example 5.

[0430]

[0431] The starting materials were used as described in the above reaction formula, except that the above compound 5 was manufactured by the same method as that used in manufacturing example 1.

[0432] MS:[M+H] + =910

[0433] Manufacturing Example 6.

[0434]

[0435] The starting materials were used as described in the above reaction formula, except that the above compound 6 was manufactured by the same method as that used in manufacturing example 1.

[0436] MS:[M+H] + =810

[0437] Manufacturing Example 7.

[0438]

[0439] The starting materials were used as described in the above reaction formula, except that the above compound 7 was manufactured by the same method as that used in manufacturing example 1.

[0440] MS:[M+H] + =876

[0441] Manufacturing Example 8.

[0442]

[0443] The starting materials were used as described in the above reaction formula, except that the above compound 8 was manufactured by the same method as that used in manufacturing example 1.

[0444] MS:[M+H] + =868

[0445] Manufacturing Example 9.

[0446]

[0447] The starting materials were used as described in the above reaction formula, except that the above compound 9 was manufactured by the same method as that used in manufacturing example 1.

[0448] MS:[M+H] + =870

[0449] Manufacturing Example 10.

[0450]

[0451] The starting materials were used as described in the above reaction formula, except that the above compound 10 was manufactured by the same method as that used in manufacturing example 1.

[0452] MS:[M+H] + =870

[0453] Manufacturing Example 11.

[0454]

[0455] The starting materials were used as described in the above reaction formula, except that the above compound 11 was manufactured by the same method as that used in manufacturing example 1.

[0456] MS:[M+H] + =910

[0457] Manufacturing Example 12.

[0458]

[0459] The starting materials were used as described in the above reaction formula, except that the above compound 12 was manufactured by the same method as that used in manufacturing example 1.

[0460] MS:[M+H] + =895

[0461] Manufacturing Example 13.

[0462]

[0463] The starting materials were used as described in the above reaction formula, except that the above compound 13 was manufactured by the same method as that used in manufacturing example 1.

[0464] MS:[M+H] + =894

[0465] Manufacturing Example 14.

[0466]

[0467] The starting materials were used as described in the above reaction formula, except that the above compound 14 was manufactured by the same method as that used in manufacturing example 1.

[0468] MS:[M+H] + =819

[0469] Manufacturing Example 15.

[0470]

[0471] The starting materials were used as described in the above reaction formula, except that the above compound 15 was manufactured by the same method as that used in manufacturing example 1.

[0472] MS:[M+H] + =834

[0473] Manufacturing Example 16.

[0474]

[0475] The starting materials were used as described in the above reaction formula, except that the above compound 16 was manufactured by the same method as that used in manufacturing example 1.

[0476] MS:[M+H] + =793

[0477] Manufacturing Example 17.

[0478]

[0479] The starting materials were used as described in the above reaction formula, except that the above compound 17 was manufactured by the same method as that used in manufacturing example 1.

[0480] MS:[M+H] + =821

[0481] Manufacturing Example 18.

[0482]

[0483] The starting materials were used as described in the above reaction formula, except that the above compound 18 was manufactured by the same method as that used in manufacturing example 1.

[0484] MS:[M+H] + =910

[0485] Manufacturing Example 19.

[0486]

[0487] The starting materials were used as described in the above reaction formula, except that the above compound 19 was manufactured by the same method as that used in manufacturing example 1.

[0488] MS:[M+H] + =819

[0489] Example 1-1

[0490] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing a detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0491] On the prepared ITO transparent electrode, a hole injection layer is formed by thermal vacuum evaporation of the following compound HI-A to a thickness of 600 Å. On the hole injection layer, 50 Å of the following compound HAT and 60 Å of the following compound HT-A are sequentially vacuum-deposited to form a first hole transport layer and a second hole transport layer.

[0492] Next, on the second hole transport layer, compounds BH and BD are vacuum-deposited at a weight ratio of 25:1 with a film thickness of 200 Å to form a light-emitting layer.

[0493] On the aforementioned light-emitting layer, compound 1 and compound LiQ, manufactured above, are vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 350 Å. On the aforementioned electron injection and transport layer, lithium fluoride (LiF) is sequentially deposited with a thickness of 10 Å and aluminum with a thickness of 1000 Å to form a cathode.

[0494]

[0495] In the above process, the evaporation rate of organic materials was maintained at 0.4 Å / s to 0.9 Å / s, the evaporation rate of lithium fluoride at the cathode was maintained at 0.3 Å / s, and the evaporation rate of aluminum was maintained at 2 Å / s. During evaporation, the vacuum level was maintained at 1 x 0. -7 Up to 5x10 -5 This led to the creation of organic light-emitting devices.

[0496] Examples 1-2 to Examples 1-19

[0497] Organic light-emitting devices were manufactured by replacing compound 1 in Examples 1-1 with compounds 2 to 19 listed in Table 1 below, except that the method was the same as that used in Examples 1-1.

[0498]

[0499] Comparative Examples 1-1 to 1-4

[0500] Organic light-emitting devices were manufactured using the same method as in Example 1-1, except that compounds ET-1 to ET-4 from Table 1 below were used instead of compound 1 from Example 1-1. The structures of compounds ET-1 to ET-4 from Table 1 below are shown below.

[0501]

[0502] Device Evaluation

[0503] For the organic light-emitting devices manufactured in Examples 1-1 to 1-19 and Comparative Examples 1-1 to 1-4 above, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T90) at the given current density was measured relative to the initial brightness reaching 90%. The results are shown in Table 1 below.

[0504]

[0505] As described in Table 1 above, the compounds represented by Formula 1 according to this specification can be used as electron injection and transport layers in organic light-emitting devices. According to one embodiment of this specification, Formula 1 is a compound having a benzene core with a heterocyclic bicyclic ring containing one or two N atoms, wherein the benzene must contain arylene groups on both sides as linking groups, and heteroarylene groups containing two or three N atoms as substituents. Because this compound has an electron-depleted structure, the polarity (dipole moment) of the molecule can be increased. Therefore, when fabricating an organic light-emitting device containing the compound represented by Formula 1, the electron mobility can be smoothly adjusted. Examples 1-1 to 1-19, which contain the compound, exhibit low voltage, high efficiency, and long lifetime.

[0506] Specifically, it can be seen that the above-described Examples 1-1 to 1-19 are superior in terms of driving voltage, efficiency and lifetime compared to Comparative Examples 1-1 and 1-2, which contain at least one of the connecting groups L1 and L2, which are directly bonded to benzene of Formula 1 of this specification.

[0507] It can be seen that Examples 1-1 to 1-19 above are superior in terms of driving voltage, efficiency and lifetime compared to Comparative Examples 1-3, which contain compounds with N-containing heterocyclic groups containing monocyclic groups instead of bicyclic N-containing heterocyclic groups as described in this specification.

[0508] Furthermore, it is evident that Examples 1-1 to 1-19 described above are superior in terms of efficiency and lifetime compared to Comparative Examples 1-4, which contain N-containing heterocyclic groups that replace the bicyclic groups in this specification with naphthyl groups.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, Any one or two of Y1 to Y8 are N, any one of the remaining ones is C combined with chemical formula 1, and the rest are CR3 independently. X1 is either N or CR'1. X2 is either N or CR'2. R'1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a moiety combined with L1, or a substituted or unsubstituted aromatic hydrocarbon ring formed by combining with R1. R'2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a moiety combined with L2, or combined with R2 to form a substituted or unsubstituted aromatic hydrocarbon ring. R1 and R2 may be the same as or different from each other, and each may independently be a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may combine with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring. R3 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group. L1 and L2 may be the same or different from each other, and each may be a substituted or unsubstituted aryl group independently. n1 and n2 are each integers from 1 to 5. r1 and r2 are each integers from 1 to 3. When n1 is 2 or more, the two or more L1s are either the same or different from each other. When n2 is 2 or more, the two or more L2s are either the same or different from each other. When r1 is 2 or more, the two or more R1 values ​​are either the same or different from each other. When r2 is 2 or more, the two or more R2s are the same or different from each other.

2. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] In the chemical formulas 1-1 to 1-6, The definitions of Y1 to Y8, X1, X2, R1, R2, r1, r2, L1, L2, n1, and n2 are the same as those in Chemical Formula 1.

3. The compound according to claim 1, wherein, The chemical formula 1 is the following chemical formula 2: [Chemical Formula 2] In the chemical formula 2, The definitions of Y1 to Y8, X1, X2, R1, R2, r1, and r2 are the same as those in Chemical Formula 1.

4. The compound according to claim 1, wherein, Chemical Formula 1 It is any of the following structures: In the structure, For the site where it binds to chemical formula 1, R31 to R38 may be the same as or different from each other, and each is independently hydrogen, deuterium, or substituted or unsubstituted alkyl.

5. The compound according to claim 1, wherein, The chemical formula 1 It is any of the following structures: In the structure, For the site where it combines with chemical formula 1, The definitions of L1, n1, R1, r1, and R'1 are the same as those in Chemical Formula 1. R101 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. r101 is an integer from 1 to 4. When r101 is 2 or more, the two or more R101 are the same or different from each other.

6. The compound according to claim 1, wherein, The chemical formula 1 It is selected from any of the following structures: In the structure, For the site where it combines with chemical formula 1, The definitions of L2, n2, R2, r2, and R'2 are the same as those in Chemical Formula 1. R201 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. R201 is an integer from 1 to 4. When there are 2 or more r201, the two or more R201 are the same or different from each other.

7. The compound according to claim 1, wherein, The chemical formula 1 and They are the same. For the site where it combines with chemical formula 1, The definitions of L2, n2, R2, r2, and R'2 are the same as those in Chemical Formula 1.

8. The compound according to claim 1, wherein, R1 and R2 may be the same as or different from each other, and each independently is a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 carbon atoms, or an aryl group with 2 to 30 carbon atoms substituted or unsubstituted with a heteroaryl group with 2 to 30 carbon atoms substituted or unsubstituted with a heteroaryl group with 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group with 1 to 30 carbon atoms; or a heteroaryl group with 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group with 2 to 30 carbon atoms. R'1 is hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a moiety combined with L1. The R'2 is hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a moiety combined with L2. The L1 and L2 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 carbon atoms. R3 is hydrogen, deuterium, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

9. The compound according to claim 1, wherein, Chemical Formula 1 is any one of the following compounds: 。 10. An organic light-emitting device, wherein, include: A first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound according to any one of claims 1 to 9.

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

12. The organic light-emitting device according to claim 10, wherein, The organic layer includes a hole-blocking layer, which contains the compound.

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