Compound and organic light-emitting device comprising same

Abstract

The present specification relates to Chemical Formula 1 and an organic light emitting device comprising the same. The organic light-emitting device includes a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, and one or more of the organic material layers may contain a compound of chemical formula 1. Specifically, the organic layer includes at least one of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and at least one of the layers may include a compound of chemical formula 1.

Description

TECHNICAL FIELD

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

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

[0003] In the present specification, an organic light emitting device is a light emitting device using an organic semiconductor material, and requires the exchange of holes and / or electrons between electrodes and the organic semiconductor material. The organic light emitting device can be roughly classified into two types according to the working principle. The first type is a light emitting device in which a photon flowing into the device from an external light source forms an exiton in an organic layer, the exiton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light emitting device in which a voltage or a current is applied to two or more electrodes, and holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes, and the device operates by the injected electrons and holes.

[0004] Generally, an organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic substance. An organic light emitting device using the organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different substances, respectively, for example, can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, an exiton is formed, and when the exiton re-travels to a ground state, light is emitted. Such an organic light emitting device is known to have characteristics of self-light emission, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, etc.

[0005] Materials used in the organic light emitting device as the organic layer can be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron blocking material, an electron transport material, an electron injection material, etc., according to the function. According to the light emitting color, the light emitting material has blue, green, red light emitting materials, and yellow and orange light emitting materials required for realizing better natural colors.

[0006] In addition, in order to increase color purity and increase the light emission efficiency based on energy transfer, as a light emitting material, a host / dopant system can be used. The principle is that when a dopant having a small energy band gap and excellent light emission efficiency compared to a host that mainly constitutes a light emitting layer is mixed in a small amount in the light emitting layer, the excitons generated in the host are transferred to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range of the dopant, the light of the desired wavelength can be obtained depending on the kind of the dopant used.

[0007] In order to sufficiently exhibit the excellent characteristics of the above-described organic light emitting device, the substances constituting the organic layer in the device, such as a hole injection substance, a hole transport substance, a light emitting substance, an electron blocking substance, an electron transport substance, an electron injection substance, etc. are backed by stable and effective materials, and thus the development of new materials is continuously required. SUMMARY

[0008] TECHNICAL PROBLEM

[0009] A compound and an organic light emitting device including the same are described in the specification.

[0010] SOLUTION TO PROBLEM

[0011] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above Chemical Formula 1,

[0015] R1 to R5 are the same as or different from each other, and each is independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0016] Ar1 is a substituted or unsubstituted heteroarylene group having 6 to 20 carbon atoms, containing 2 or more N,

[0017] Ar2 is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0018] A is the following Chemical Formula 2-1 or Chemical Formula 2-2,

[0019] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0020]

[0021] In the above Chemical Formula 2-1 or Chemical Formula 2-2,

[0022] a site to be combined with the above Chemical Formula 1,

[0023] any one or two of X1to X7is N, and the rest is CR',

[0024] R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

[0025] a and c are each an integer of 1 to 4,

[0026] b is an integer of 1 to 3,

[0027] d and e are each an integer of 1 to 5,

[0028] when a is 2 or more, R1are the same as or different from each other,

[0029] when b is 2 or more, R2are the same as or different from each other,

[0030] when c is 2 or more, R3are the same as or different from each other,

[0031] when d is 2 or more, R4are the same as or different from each other,

[0032] when e is 2 or more, R5are the same as or different from each other.

[0033] In addition, according to an embodiment of the present application, there is provided an organic light emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound described above.

[0034] Effects of the Invention

[0035] The compound of the present application can be used as a material for an organic layer of an organic light emitting device. When an organic light emitting device is manufactured to include the compound of the present application, an organic light emitting device having high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present application is included in an electron injection and transport layer of an organic light emitting device, the intramolecular polarizability is high, and the electron transfer effect is good, so that an organic light emitting device having long lifespan characteristics can be manufactured.

[0036] The compound of the present application limits the substitution position of the linking group to the ortho direction instead of reducing the distance between the electron transport groups, maximizes the electron mobility by appropriately cutting the conjugation within the molecule, and thus shows high efficiency characteristics.

[0037] By introducing quinoline or quinazoline as a highly electronegative substituent, the long lifespan characteristics are also maintained. BRIEF DESCRIPTION OF DRAWINGS

[0038] Figure 1 and 2 An example of an organic light emitting device according to the present application is illustrated.

[0039] <Explanation of Symbols>

[0040] 1: Substrate

[0041] 2: Anode

[0042] 3: Organic layer

[0043] 4: Cathode

[0044] 5: Hole injection layer

[0045] 6: Hole transport layer

[0046] 7: Electron blocking layer

[0047] 8: Light emitting layer

[0048] 9: Hole blocking layer

[0049] 10: Electron injection and transport layer DETAILED DESCRIPTION

[0050] Hereinafter, the present specification will be described in more detail.

[0051] In the present specification, when a certain part is referred to as "including / including" a certain component, unless otherwise specifically noted, it means that another component can be further included, rather than excluding another component.

[0052] In the present specification, when a certain member is referred to as being "on" another member, it not only includes the case where the certain member is directly on the other member, but also includes the case where another member is interposed therebetween.

[0053] In the present specification, examples of substituents are described below, but are not limited thereto.

[0054] The term "substituted" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom can be substituted, i.e., the position where a substituent can be substituted, and when two or more are substituted, the two or more substituents can be the same or different.

[0055] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano (-CN), silyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic groups, or substituted by two or more substituents linked together as exemplified above, or without any substituents. For example, "a substituent linked together as two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent linked together as two phenyl groups.

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

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

[0058] In this specification, silyl groups may be substituted or unsubstituted with deuterium, substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups. Specific examples of the aforementioned silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited to these.

[0059] In this specification, the boron group may be substituted with or unsubstituted with deuterium, substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups. Specific examples of the aforementioned boron groups include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited to these.

[0060] 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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited to these.

[0061] 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-methylanthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, 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.

[0062] In this specification, N-alkylarylamine refers to an amine group in which an alkyl or aryl group is substituted for the N group.

[0063] In this specification, N-arylheteroarylamine refers to an amine group in which an aryl or heteroaryl group is substituted at the N-position of the amine group.

[0064] In this specification, N-alkylheteroarylamine refers to an amine group in which an alkyl or heteroaryl group is substituted at the N-position of the amine group.

[0065] In this specification, alkylamine, N-arylalkylamine, and alkylthio ( ), alkylsulfonyl ( The alkyl group in the N-alkylheteroarylamine group 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.

[0066] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0067] In this specification, the aryl group is not particularly limited, but it is preferably an aryl group with 6 to 60 carbon atoms, which can be a monocyclic aryl, a bicyclic aryl, or a tricyclic or more aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. The bicyclic aryl group can be naphthyl, pentenyl, indene, azulel, hepta-enyl, etc., but is not limited thereto. The tricyclic or more aryl group can be anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, phenylene, fluorene, etc., but is not limited thereto.

[0068] In this specification, a heteroaryl group is a cyclic group containing one or more heteroatoms selected from N, O, P, S, Si, and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms.

[0069] In this specification, heteroaryl groups can be monocyclic, bicyclic, or tricyclic or more. Examples of monocyclic heteroaryl groups include pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, and pyrazolyl, but are not limited to these. Examples of bicyclic heteroaryl groups include quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, indolyl, benzothiopheneyl, and benzofuranyl, but are not limited to these. Examples of tricyclic or more heteroaryl groups include dibenzofuranyl, dibenzothiopheneyl, and carbazoleyl, but are not limited to these.

[0070] In this specification, arylene is a divalent group, otherwise it is the same as the definition of aryl above.

[0071] In this specification, the heteroaryl group is a divalent group, otherwise it is the same as the definition of heteroaryl groups above.

[0072] In this specification, a fused ring refers to a ring formed by the fusion of two or more aliphatic hydrocarbon rings, aromatic hydrocarbon rings, and heterocycles. The aliphatic hydrocarbon rings are subject to the definition of cycloalkyl groups as described above, except that they are not monovalent. The aromatic hydrocarbon rings are subject to the definition of aryl groups as described above, except that they are not monovalent. The heterocycles are subject to the definition of heteroaryl groups as described above, except that they are not monovalent.

[0073] In this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-10.

[0074] [Chemical Formula 1-1]

[0075]

[0076] [Chemical Formula 1-2]

[0077]

[0078] [Chemical Formulas 1-3]

[0079]

[0080] [Chemical Formulas 1-4]

[0081]

[0082] [Chemical Formulas 1-5]

[0083]

[0084] [Chemical Formulas 1-6]

[0085]

[0086] [Chemical Formulas 1-7]

[0087]

[0088] [Chemical Formulas 1-8]

[0089]

[0090] [Chemical Formulas 1-9]

[0091]

[0092] [Chemical Formulas 1-10]

[0093]

[0094] In the above chemical formulas 1-1 to 1-10, R1 to R5, Ar1, Ar2, A and a to e are defined in the same way as in chemical formula 1.

[0095] In one embodiment of the present invention, the above-mentioned chemical formula 1 is any one of the following chemical formulas 1-1-1 to 1-1-10.

[0096] [Chemical Formula 1-1-1]

[0097]

[0098] [Chemical Formula 1-1-2]

[0099]

[0100] [Chemical Formula 1-1-3]

[0101]

[0102] [Chemical Formula 1-1-4]

[0103]

[0104] [Chemical Formula 1-1-5]

[0105]

[0106] [Chemical Formula 1-1-6]

[0107]

[0108] [Chemical Formula 1-1-7]

[0109]

[0110] [Chemical Formula 1-1-8]

[0111]

[0112] [Chemical Formula 1-1-9]

[0113]

[0114] [Chemical Formula 1-1-10]

[0115]

[0116] In the above chemical formulas 1-1-1 to 1-1-10, R4, R5, Ar1, Ar2, A, d, and e are defined in the same way as in chemical formula 1.

[0117] According to one embodiment of this specification, R1 to R3 in the above chemical formulas 1-1 to 1-10 are hydrogen or deuterium.

[0118] According to one embodiment of this specification, Ar1 is a heteroaryl group containing 3 to 30 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0119] According to one embodiment of this specification, Ar1 is a heteroaryl group containing 3 to 20 substituted or unsubstituted carbon atoms, comprising 2 or more N atoms.

[0120] According to one embodiment of this specification, Ar1 is a heteroaryl group comprising 3 to 15 substituted or unsubstituted carbon atoms containing 2 or more N atoms.

[0121] According to one embodiment of this specification, Ar1 is a monocyclic or polycyclic heteroaryl group containing 3 to 30 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0122] According to one embodiment of this specification, the Ar1 mentioned above is a monocyclic or polycyclic heteroaryl group containing 3 to 20 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0123] According to one embodiment of this specification, Ar1 is a monocyclic or polycyclic heteroaryl group containing 3 to 15 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0124] According to one embodiment of this specification, Ar1 is a monocyclic heteroaryl group containing 3 to 30 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0125] According to one embodiment of this specification, Ar1 is a monocyclic heteroaryl group containing 3 to 20 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0126] According to one embodiment of this specification, Ar1 is a monocyclic heteroaryl group containing 3 to 15 substituted or unsubstituted carbon atoms with 2 or more N atoms.

[0127] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted divalent triazine group or a substituted or unsubstituted divalent pyrimidin group.

[0128] According to one embodiment of this specification, Ar1 is a divalent triazine group substituted or unsubstituted with hydrogen or aryl groups, or a divalent pyrimidinyl group substituted or unsubstituted with hydrogen or aryl groups.

[0129] According to one embodiment of this specification, Ar1 is a divalent triazine group substituted or unsubstituted with hydrogen, phenyl, biphenyl or naphthyl; or a divalent pyrimidinyl group substituted or unsubstituted with hydrogen, phenyl, biphenyl or naphthyl.

[0130] According to one embodiment of this specification, Ar1 is a divalent triazine group substituted or unsubstituted with hydrogen, phenyl, biphenyl or naphthyl.

[0131] According to one embodiment of this specification, Ar1 is a divalent pyrimidinyl group substituted or unsubstituted with hydrogen, phenyl, biphenyl or naphthyl.

[0132] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted divalent quinazolinyl group.

[0133] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted divalent quinoxalinyl group.

[0134] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted divalent imidazole group.

[0135] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted divalent benzimidazole group.

[0136] According to one embodiment of this specification, Ar1 is a divalent quinazolinyl group that is substituted with or unsubstituted with deuterium or aryl.

[0137] According to one embodiment of this specification, Ar1 is a divalent quinoxalinyl group that is substituted with or unsubstituted with deuterium or aryl.

[0138] According to one embodiment of this specification, Ar1 is a divalent imidazolyl group that is substituted with or unsubstituted with deuterium, alkyl or aryl groups.

[0139] According to one embodiment of this specification, Ar1 is a divalent benzimidazolyl group that is substituted with or unsubstituted with deuterium, alkyl or aryl groups.

[0140] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, nitrile group, halogen group, alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, aryl group with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl group with 3 to 30 substituted or unsubstituted carbon atoms, or fused ring group with 3 to 30 substituted or unsubstituted carbon atoms.

[0141] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0142] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0143] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0144] According to one embodiment of this specification, Ar2 is hydrogen; deuterium; nitrile group; halogen group; alkyl group having 1 to 10 carbon atoms substituted or unsubstituted by one or more groups selected from deuterium, halogen group, alkyl, aryl and heterocyclic group or groups formed by two or more linked groups; or aryl group having 6 to 30 carbon atoms substituted or unsubstituted by one or more groups selected from deuterium, halogen group, alkyl, aryl and heterocyclic group or groups formed by two or more linked groups.

[0145] According to one embodiment of this specification, Ar2 is hydrogen; deuterium; nitrile group; halogen group; alkyl group having 1 to 6 carbon atoms substituted or unsubstituted by one or more groups selected from deuterium, halogen group, alkyl, aryl and heterocyclic group; or aryl group having 6 to 20 carbon atoms substituted or unsubstituted by one or more groups selected from deuterium, halogen group, alkyl, aryl and heterocyclic group.

[0146] According to one embodiment of this specification, Ar2 is hydrogen; deuterium; nitrile group; halogen group; alkyl group having 1 to 6 carbon atoms substituted or unsubstituted by one or more groups selected from deuterium, halogen group, alkyl, aryl and heterocyclic group; or aryl group having 6 to 15 carbon atoms substituted or unsubstituted by one or more groups selected from deuterium, halogen group, alkyl, aryl and heterocyclic group.

[0147] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, nitrile, halogen group, methyl, ethyl, tert-butyl, isopropyl, phenyl, biphenyl, naphthyl, anthracene, or phenanthryl.

[0148] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, nitrile, halogen group, methyl, ethyl, phenyl, biphenyl or naphthyl.

[0149] According to one embodiment of this specification, the Ar2 mentioned above is hydrogen, deuterium, phenyl, biphenyl, or naphthyl.

[0150] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0151] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, halogen group, substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms.

[0152] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, halogen group, or alkyl group with 1 to 10 carbon atoms, whether substituted or unsubstituted.

[0153] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, halogen group, alkyl with 1 to 10 carbon atoms, aryl with 6 to 30 carbon atoms, or heteroaryl with 3 to 30 carbon atoms.

[0154] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile group, halogen group, or alkyl group with 1 to 10 carbon atoms.

[0155] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each independently represents hydrogen, deuterium, nitrile, F, Cl, Br, I, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, pyrrole, furanyl, thiophene, triazine, pyrimidinyl, pyridinyl, carbazole, dibenzofuranyl, or dibenzothiophene.

[0156] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each independently represents hydrogen, deuterium, nitrile, F, Cl, Br, I, methyl, ethyl, propyl, isopropyl, butyl, phenyl, naphthyl or tert-butyl.

[0157] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, halogen, phenyl or naphthyl.

[0158] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, phenyl or naphthyl.

[0159] According to one embodiment of this specification, R1 to R5 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0160] According to one embodiment of this specification, R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0161] According to one embodiment of this specification, R' is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted.

[0162] According to one embodiment of this specification, R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, whether substituted or unsubstituted.

[0163] According to one embodiment of this specification, R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, whether substituted or unsubstituted.

[0164] According to one embodiment of this specification, R' is hydrogen, deuterium, or a substituted or unsubstituted ethyl or a substituted or unsubstituted methyl.

[0165] According to one embodiment of this specification, any one or two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0166] According to one embodiment of this specification, any one of X1 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0167] According to one embodiment of this specification, any two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0168] According to one embodiment of this specification, any one of X1 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted.

[0169] According to one embodiment of this specification, any one of X1 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.

[0170] According to one embodiment of this specification, any one of X1 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted.

[0171] According to one embodiment of this specification, any one of X1 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms, substituted or unsubstituted.

[0172] According to one embodiment of this specification, any one of X1 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or methyl.

[0173] According to one embodiment of this specification, any two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted.

[0174] According to one embodiment of this specification, any two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted.

[0175] According to one embodiment of this specification, any two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group with 1 to 10 carbon atoms, substituted or unsubstituted.

[0176] According to one embodiment of this specification, any two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms, substituted or unsubstituted.

[0177] According to one embodiment of this specification, any two of X1 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or methyl.

[0178] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0179] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0180] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted.

[0181] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.

[0182] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted.

[0183] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms, whether substituted or unsubstituted.

[0184] According to one embodiment of this specification, any one of X1 to X3 is N, and the rest are CR', where R' is hydrogen, deuterium, or methyl.

[0185] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted.

[0186] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.

[0187] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted.

[0188] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms, substituted or unsubstituted.

[0189] According to one embodiment of this specification, any two of X1 to X3 are N, and the rest are CR', where R' is hydrogen, deuterium, or methyl.

[0190] According to one embodiment of this specification, any one of X4 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0191] According to one embodiment of this specification, any two of X4 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0192] According to one embodiment of this specification, any one of X4 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted.

[0193] According to one embodiment of this specification, any one of X4 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.

[0194] According to one embodiment of this specification, any one of X4 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted.

[0195] According to one embodiment of this specification, any one of X4 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms, substituted or unsubstituted.

[0196] According to one embodiment of this specification, any one of X4 to X7 is N, and the rest are CR', where R' is hydrogen, deuterium, or methyl.

[0197] According to one embodiment of this specification, any two of X4 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted.

[0198] According to one embodiment of this specification, any two of X4 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted.

[0199] According to one embodiment of this specification, any two of X4 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted.

[0200] According to one embodiment of this specification, any two of X4 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or an alkyl group having 1 to 3 carbon atoms, substituted or unsubstituted.

[0201] According to one embodiment of this specification, any two of X4 to X7 are N, and the rest are CR', where R' is hydrogen, deuterium, or methyl.

[0202] According to one embodiment of this specification, the above chemical formula 1 is any one of the following structural formulas.

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] According to one embodiment of this specification, R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0240] According to one embodiment of this specification, R' is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted.

[0241] According to one embodiment of this specification, R' is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms, whether substituted or unsubstituted.

[0242] According to one embodiment of this specification, R' is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, whether substituted or unsubstituted.

[0243] According to one embodiment of this specification, R' is hydrogen, deuterium, or substituted or unsubstituted ethyl or methyl.

[0244] The substituents of the compound of the above chemical formula 1 can be combined by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.

[0245] Furthermore, by introducing various substituents into the core structure described above, compounds possessing the inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the aforementioned core structure, substances satisfying the requirements of each organic layer can be synthesized.

[0246] Furthermore, the organic light-emitting device according to the present invention is characterized in that it includes a first electrode, a second electrode disposed opposite to the first 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.

[0247] The organic light-emitting device of the present invention utilizes the above-mentioned compound to form one or more organic layers. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0248] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0249] The organic layer of the organic light-emitting device of the present invention 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, the organic light-emitting device of the present invention can have a structure comprising an organic layer including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, and an electron injection layer. However, the structure of the organic light-emitting device is not limited to this, and may include fewer or more organic layers.

[0250] In the organic light-emitting device of the present invention, the organic layer may include an electron transport layer, an electron injection layer, and one or more electron injection and transport layers, wherein one or more of the above layers may contain a compound represented by the above chemical formula 1.

[0251] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, which may contain a compound represented by the above chemical formula 1.

[0252] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises the compound of chemical formula 1 and a metal complex.

[0253] In the organic light-emitting device of the present invention, the organic layer may include one or more of a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport simultaneously, wherein one or more of the aforementioned layers may contain a compound represented by the aforementioned chemical formula 1.

[0254] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, which may contain a compound represented by the above chemical formula 1.

[0255] In one embodiment of this specification, the first electrode is the anode and the second electrode is the cathode.

[0256] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0257] (1) Anode / hole transport layer / light-emitting layer / cathode

[0258] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0259] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0260] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0261] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0262] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0263] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0264] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0265] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0266] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0267] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0268] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0269] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0270] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0271] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0272] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0273] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0274] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron injection and transport layer / Cathode

[0275] The organic light-emitting device of the present invention can have the following structure: Figure 1 and 2 The structure shown is not limited to this.

[0276] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which an anode 2, an organic layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the compound represented by the above-described chemical formula 1 may be included in the organic layer 3.

[0277] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a cathode 4 are sequentially stacked on a substrate 1. The compound represented by the above-described chemical formula 1 may be included in the hole blocking layer 9 or the electron injection and transport layer 10.

[0278] For example, the organic light-emitting device according to the present invention can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, one or more organic layers are formed on the anode, including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0279] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0280] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include 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; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0281] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0282] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltages. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of 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, and conductive polymers based on polyaniline and polythiophene. The thickness of the hole injection layer can range from 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics; when it is less than 150 nm, it has the advantage of preventing an increase in driving voltage to improve hole migration when the hole injection layer is too thick.

[0283] 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.

[0284] According to one embodiment of this specification, the hole injection layer may contain a compound represented by the following chemical formula HI-1.

[0285] [Chemical formula HI-1]

[0286]

[0287] In the above chemical formula HI-1,

[0288] R201 to R204 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may be combined with adjacent groups to form substituted or unsubstituted rings.

[0289] In one embodiment of this specification, R201 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0290] In one embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0291] In one embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.

[0292] In one embodiment of this specification, R201 to R204 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.

[0293] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0294] In one embodiment of this specification, R201 and R203 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0295] In one embodiment of this specification, R201 and R203 may be the same as or different from each other, and each is independently an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0296] In one embodiment of this specification, R201 and R203 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl group.

[0297] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each may be a substituted or unsubstituted heteroaryl group.

[0298] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a heteroaryl group with 2 to 20 carbon atoms, either substituted or unsubstituted.

[0299] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a heteroaryl group with 2 to 10 substituted or unsubstituted carbon atoms.

[0300] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each may independently be a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazoleyl.

[0301] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a carbazole group that is substituted with or unsubstituted with an aryl group.

[0302] In one embodiment of this specification, R202 and R204 may be the same as or different from each other, and each is independently a carbazole group substituted with or unsubstituted with phenyl.

[0303] In one embodiment of this specification, the above chemical formula HI-1 is represented by the following compound.

[0304]

[0305] The aforementioned hole transport layer facilitates hole transport. The hole transport material is capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0306] 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.

[0307] [Chemical formula HT-1]

[0308]

[0309] In the above chemical formula HT-1,

[0310] At least one of X'1 to X'6 is N, and the rest are CH.

[0311] R309 to R314 may be the same as or different from each other, and each is independently hydrogen, deuterium, nitrile, 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.

[0312] According to one embodiment of this specification, X'1 to X'6 are N.

[0313] According to one embodiment of this specification, R309 to R314 are nitrile groups.

[0314] According to one embodiment of this specification, the above-mentioned chemical formula HT-1 is represented by the following compound.

[0315]

[0316] According to one embodiment of this specification, the hole transport layer may further comprise a compound with the chemical formula HT-2.

[0317] [Chemical formula HT-2]

[0318]

[0319] In the above chemical formula HT-2,

[0320] L101 is a directly bonded, substituted, or unsubstituted aryl group.

[0321] R101 to R103 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0322] According to one embodiment of this specification, L101 is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.

[0323] According to one embodiment of this specification, L101 is a directly bonded, substituted, or unsubstituted phenylene oxide.

[0324] According to one embodiment of this specification, L101 is directly bonded or phenylene.

[0325] According to one embodiment of this specification, R101 to R103 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl or a substituted or unsubstituted polycyclic aryl.

[0326] According to one embodiment of this specification, R101 to R103 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrene, or a substituted or unsubstituted fluorene.

[0327] According to one embodiment of this specification, R101 to R103 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted fluorenyl.

[0328] According to one embodiment of this specification, R101 to R103 may be the same as or different from each other, and each is independently a phenyl, biphenyl, or fluorene group substituted with an alkyl group.

[0329] According to one embodiment of this specification, the above-mentioned chemical formula HT-2 is represented by the following compound.

[0330]

[0331] An electron blocking layer can be disposed between the hole transport layer and the light-emitting layer. This electron blocking layer can be a spirocyclic compound or a material known in the art.

[0332] The aforementioned luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent substances. The luminescent substance is capable of receiving holes and electrons from the hole transport layer and electron transport layer respectively, and combining them to emit light in the visible light region; preferably, it is a substance with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds of the azole, benzothiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0333] As the main material for the luminescent layer, there are aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. ), pyrimidine derivatives, etc., but not limited to these.

[0334] 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.

[0335] [Chemical formula H-1]

[0336]

[0337] In the above chemical formula H-1,

[0338] 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 heteroaryl group.

[0339] 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.

[0340] 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.

[0341] 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.

[0342] 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.

[0343] 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 unsubstituted naphthylene, divalent dibenzofuranyl, or divalent dibenzothiopheneyl.

[0344] In one embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0345] 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.

[0346] 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.

[0347] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently a phenyl substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl 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. Aryl-substituted or unsubstituted thiophene group; dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0348] 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.

[0349] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently 1-naphthyl or 2-naphthyl.

[0350] According to one embodiment of this specification, R201 is hydrogen.

[0351] According to one embodiment of this specification, the above chemical formula H-1 is represented by the following compound.

[0352]

[0353] When the luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonateiridium), PQIr (tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum) can be used; or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the emissive layer emits green light, phosphorescent materials such as Ir(ppy)3 (planar tris(2-phenylpyridine)iridium) and fac tris(2-phenylpyridine)iridium, or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum), can be used as luminescent dopants, but these are not limited to these. When the emissive layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used as luminescent dopants; or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbeneylarylene (DSA), PFO-based polymers, PPV-based polymers, etc., can be used, but these are not limited to these.

[0354] In one embodiment of this specification, the light-emitting dopant comprises a compound with the following chemical formula D-1.

[0355] [Chemical Formula D-1]

[0356]

[0357] In the above chemical formula D-1,

[0358] L401 and L402 may be the same as or different from each other, and each may be a directly bonded, substituted or unsubstituted aryl group.

[0359] R401 to R404 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0360] R405 and R406 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0361] In one embodiment of this specification, L401 and L402 are each directly bonded.

[0362] In one embodiment of this specification, R401 to R404 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.

[0363] In one embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl, a substituted or unsubstituted polycyclic aryl, or a substituted or unsubstituted heterocyclic group.

[0364] In one embodiment of this specification, R401 to R404 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0365] In one embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl or a substituted or unsubstituted dibenzofuranyl.

[0366] In one embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a phenyl group that is substituted with or unsubstituted with an alkyl group, or a dibenzofuran group that is substituted with or unsubstituted with an alkyl group.

[0367] In one embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a phenyl substituted with cyano or hydrogen, or a phenyl substituted with deuterium.

[0368] In one embodiment of this specification, R405 and R406 are tert-butyl.

[0369] In one embodiment of this specification, the above chemical formula D-1 is represented by the following compound.

[0370]

[0371] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing an increase in driving voltage to improve electron migration when the electron transport layer is too thick.

[0372] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0373] The aforementioned electron injection and transport layers can be manufactured using materials appropriately selected for the electron injection and electron transport layers.

[0374] The aforementioned electron injection and transport layers can be manufactured together using the compound of chemical formula 1 and the metal complex.

[0375] The aforementioned electron injection and transport layer contains the compound of chemical formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.

[0376] The aforementioned electron injection and transport layer contains the compound of chemical formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.

[0377] 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.

[0378] In one embodiment of this specification, the metal coordination compound is represented by the following compound.

[0379]

[0380] A hole blocking layer can be provided between the electron transport layer and the light-emitting layer, and materials known in this art can be used.

[0381] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the hole injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0382] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0383] The organic light-emitting device of the present invention utilizes the above-mentioned compound to form one or more organic layers. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0384] Methods of implementing the invention

[0385] The method for manufacturing the compound of chemical formula 1 and the method for manufacturing organic light-emitting devices using the compound are specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0386] In the following reaction formulas, the types and numbers of substituents can be appropriately selected from known starting materials by those skilled in the art to synthesize various types of intermediates. The types and conditions of the reactions can utilize techniques known in this art.

[0387] The method for manufacturing the compound of chemical formula 1 and the method for manufacturing organic light-emitting devices using the compound are specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0388] In the following reaction formulas, the types and numbers of substituents can be appropriately selected from known starting materials by those skilled in the art to synthesize various types of intermediates. The types and conditions of the reactions can utilize techniques known in this art.

[0389] Manufacturing Example 1.

[0390]

[0391] 12.7 g (30 mmol) of 2-(2-bromo-6-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and compound 1-1 (8.2 g (33 mmol) were added to tetrahydrofuran (300 mL). 2 M K₂CO₃ (200 mL) and tetra(triphenylphosphine)palladium(0) (0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice from toluene to produce compound 1-2.

[0392] Compounds 1-2 (16.41 g, 30 mmol) and 1-3 (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 compound 1.

[0393] (18.45g, yield 75%, MS: [M+H]) + =820).

[0394] Manufacturing Example 2.

[0395]

[0396] 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.

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

[0398] Manufacturing Example 3.

[0399]

[0400] 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.

[0401] MS:[M+H] + =820

[0402] Manufacturing Example 4.

[0403]

[0404] 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.

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

[0406] Manufacturing Example 5.

[0407]

[0408] 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.

[0409] MS:[M+H] + =834

[0410] Manufacturing Example 6.

[0411]

[0412] 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.

[0413] MS:[M+H] + =897

[0414] Manufacturing Example 7.

[0415]

[0416] 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.

[0417] MS:[M+H] + =830

[0418] Manufacturing Example 8.

[0419]

[0420] 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.

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

[0422] Manufacturing Example 9.

[0423]

[0424] 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.

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

[0426] Manufacturing Example 10.

[0427]

[0428] 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.

[0429] MS:[M+H] + =820

[0430] Manufacturing Example 11.

[0431]

[0432] 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.

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

[0434] Manufacturing Example 12.

[0435]

[0436] 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.

[0437] MS:[M+H] + =834

[0438] Manufacturing Example 13.

[0439]

[0440] 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.

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

[0442] Manufacturing Example 14.

[0443]

[0444] 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.

[0445] MS:[M+H] + =896

[0446] Manufacturing Example 15.

[0447]

[0448] 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.

[0449] MS:[M+H] + =769

[0450] Manufacturing Example 16.

[0451]

[0452] 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.

[0453] MS:[M+H] + =857

[0454] Manufacturing Example 17.

[0455]

[0456] 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.

[0457] MS:[M+H] + =829

[0458] [Example]

[0459] Example 1-1

[0460] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing 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.

[0461] 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.

[0462] Next, on the second hole transport layer, the following compounds BH and BD are vacuum-deposited at a weight ratio of 25:1 to form a light-emitting layer with a film thickness of 200 Å.

[0463] On the aforementioned light-emitting layer, the previously manufactured compound 1 and the following compound LiQ 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.

[0464]

[0465] During 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 10⁻⁶. -7 Up to 5x10 -5 This led to the creation of organic light-emitting devices.

[0466] Examples 1-2 to Examples 1-17

[0467] Organic light-emitting devices were manufactured by replacing compound 1 in Examples 1-1 with compounds 2 to 14 listed in Table 1 below, except that the method was the same as that used in Examples 1-1.

[0468] Comparative Examples 1-1 to 1-4

[0469] Organic light-emitting devices were manufactured by replacing compound 1 in Examples 1-1 with compounds ET-1 to ET-4 listed in Table 1 below, except that the method was the same as that used in Examples 1-1. The structures of compounds ET-1 to ET-4 in Table 1 below are shown below.

[0470]

[0471] [Experimental Example]

[0472] The organic light-emitting devices manufactured in Examples 1-1 to 1-17 and Comparative Examples 1-1 to 1-4 above were tested at 10 mA / cm². 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.

[0473]

[0474] As described in Table 1 above, the compounds represented by Formula 1 according to this specification can be used in the organic layer responsible for electron injection and transport in organic light-emitting devices. As shown in Table 1 above, the compounds represented by Formula 1 limit the substitution positions of the linking groups to the ortho-ortho orientation instead of reducing the distance between electron transport groups, thereby maximizing electron mobility by appropriately severing intramolecular conjugation. Therefore, using the compounds of Formula 1 according to one embodiment of this specification in an organic light-emitting device with an electron injection and transport layer exhibits excellent characteristics in terms of efficiency, driving voltage, and stability. Furthermore, long lifetime characteristics are maintained by introducing quinoline or quinazoline as highly electronegative substituents.

[0475] Specifically, Examples 1-1 to 1-17 of organic light-emitting devices comprising compounds represented by Formula 1 according to an embodiment of this specification exhibit superior characteristics in terms of efficiency, driving voltage, and stability compared to Comparative Examples 1-1 to 1-4 of organic light-emitting devices comprising compounds in which the substitution position of the linking group is not in the ortho orientation or which do not contain quinoline or quinazoline.

[0476] The preferred embodiments of the present invention (electron injection and electron transport layer) have been described above, but the present invention is not limited thereto. Various modifications can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] ， In the chemical formula 1, R1 to R5 may be the same as or different from each other, and each is independently a hydrogen, deuterium, nitrile, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Ar1 is a heteroaryl group consisting of 6 to 20 substituted or unsubstituted carbon atoms containing two or more N atoms. Ar2 can be hydrogen, deuterium, nitrile, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. A is either chemical formula 2-1 or chemical formula 2-2. [Chemical Formula 2-1] [Chemical Formula 2-2] ， In the aforementioned chemical formula 2-1 or chemical formula 2-2, For the site where it binds to chemical formula 1, Any one or two of X1 to X7 are N, and the rest are CR'. R' is hydrogen, deuterium, or a substituted or unsubstituted alkyl group. a and c are integers from 1 to 4. b is an integer from 1 to 3. d and e are each integers from 1 to 5. When a is 2 or more, R1 is either the same or different from each other. When b is 2 or more, R² values ​​are either the same or different. When c is 2 or higher, R3 values ​​are either the same or different. When d is 2 or higher, R4 values ​​are either the same or different. When e is 2 or higher, R5 can be 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 1-10: [Chemical Formula 1-1] ， [Chemical Formula 1-2] ， [Chemical Formulas 1-3] ， [Chemical Formulas 1-4] ， [Chemical Formulas 1-5] ， [Chemical Formulas 1-6] ， [Chemical Formulas 1-7] ， [Chemical Formulas 1-8] ， [Chemical Formulas 1-9] ， [Chemical Formulas 1-10] ， In the chemical formulas 1-1 to 1-10, R1 to R5, Ar1, Ar2, A, and a to e are the same as those defined in chemical formula 1.

3. The compound according to claim 2, wherein, R1 to R3 in the chemical formulas 1-1 to 1-10 are hydrogen or deuterium.

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

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

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

7. The compound according to claim 1, wherein, Ar1 is a substituted or unsubstituted divalent imidazolyl group, or a substituted or unsubstituted divalent benzimidazolyl group.

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

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

10. The compound according to claim 1, wherein, Chemical formula 1 is any of the following structural formulas: 。 11. An organic light-emitting device, wherein, include: The first electrode, the 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 10.

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

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