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 application claims the priority of Korean Patent Application No. 10-2022-0171095 filed with the Korean Patent Office on December 9, 2022, the entire contents of which are incorporated into this specification.

[0002] The present invention relates to a compound and an organic light-emitting device including the same. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

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

[0005] Technical issues

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

[0007] Solution to the problem

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

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] At least one of X1 to X3 is N, and the others are CH,

[0013] L1 to L3 are the same or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group,

[0014] R1 to R3 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0015] Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0016] G1 to G4 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group,

[0017] g1 is an integer from 1 to 3. When the above g1 is 2 or more, the above two or more G1 are the same or different from each other.

[0018] g2 to g4 are each an integer from 1 to 4,

[0019] When the g2 is 2 or more, the two or more G2 are the same or different from each other.

[0020] When the g3 is 2 or more, the two or more G3 are the same or different from each other.

[0021] When the number of g4 is 2 or more, the two or more G4's may be the same as or different from each other.

[0022] In addition, one embodiment of the present specification provides an organic light-emitting device including: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contains the above-mentioned compound.

[0023] Effects of the Invention

[0024] The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device. The compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage and / or improved life characteristics in an organic light-emitting device. In particular, the compounds described in this specification can be used as materials for electron injection, electron transport, electron injection and electron transport, or hole blocking. In addition, compared with existing organic light-emitting devices, it has the effects of low driving voltage, high efficiency and / or long life. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 and 2 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0026] [Explanation of symbols]

[0027] 1: Substrate

[0028] 2: First electrode

[0029] 3: Second electrode

[0030] 4: Organic layer

[0031] 5: Hole injection layer

[0032] 6: Hole transport layer

[0033] 7: Electron blocking layer

[0034] 8: Luminous layer

[0035] 9: Hole blocking layer

[0036] 10: Electron injection and transport layer DETAILED DESCRIPTION

[0037] Next, this specification is described in more detail.

[0038] This specification provides the compound of the above Chemical Formula 1.

[0039] According to one embodiment of the present specification, the chemical formula 1 is a compound containing a monocyclic N-containing six-membered heterocyclic ring in which any one of the 1' to 4' positions of the spirofluorene-9,9'-xanthene nucleus is substituted by -L3-SiR1R2R3, and its structural feature is that the bulky silyl group (-SiR1R2R3) participates in the conjugation system through the hyperconjugation effect, so that the excited and polaronic states of the chemical formula 1 are stabilized. Therefore, the chemical formula 1 is included in the organic layer of the organic light-emitting device to achieve improved efficiency, lower driving voltage and improved life characteristics.

[0040] In the present specification, examples of substituents are described below, but are not limited thereto.

[0041] In this manual, Indicates the connected part.

[0042] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0043] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a haloalkyl group, a silyl group, a boron group, an amine group, an aryl group, a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a heteroaryl group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0044] In this specification, two or more substituents are linked to each other, which means that the hydrogen of any substituent is linked to another substituent. For example, two substituents can be linked to each other to form a phenyl group and a naphthyl group. In addition, the three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form The above definition also applies to 4 or more substituents connected together.

[0045] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0046] In the present specification, the alkyl group may be linear 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, and 5-methylhexyl.

[0047] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically includes 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 and the like, but is not limited thereto.

[0048] In this specification, the alkoxy group can be straight chain, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, it can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentoxy group, a n-hexoxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octoxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but it is not limited thereto.

[0049] In the present specification, the alkenyl group may 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, and the like, but are not limited thereto.

[0050] In the present specification, a haloalkyl group refers to an alkyl group in the above definition of an alkyl group substituted with at least one halogen group.

[0051] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0052] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0053] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, yl, fluorenyl, etc., but are not limited to these.

[0054] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0055] Examples of the fluorenyl group include

[0056]

[0057] etc., but not limited thereto.

[0058] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0059] In the present specification, the heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridine, phenanthroline, isothiophene Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothioyl, phenanthroline Thiazole (phenoxathiine), phen Examples of the present invention include, but are not limited to, phenoxazine, phenothiazine, indenocarbazolyl, spirofluorenylxanthenyl and spirofluorenylthioxanthenyl.

[0060] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the examples of the alkyl group described above, the aryl group in the arylsilyl group may be the same as the examples of the aryl group described above, and the heteroaryl group in the heteroarylsilyl group may be the same as the examples of the heteroaryl group described above.

[0061] In this specification, the boron group can be -BR 100 R 101 , the above R 100 and R 101 The same or different, each independently can be selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted linear or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms. The above-mentioned boryl group specifically includes dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but is not limited thereto.

[0062] In the present specification, the amino group can 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 the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methyl-anthrylamino, diphenylamino, ditolylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0063] In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group. The alkyl group and the aryl group in the above-mentioned N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

[0064] In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.

[0065] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the heteroaryl group described above.

[0066] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups or substituted or unsubstituted diarylamine groups. The arylamine groups containing two or more of the above aryl groups may contain monocyclic aryl groups, polycyclic aryl groups, or may contain both monocyclic aryl groups and polycyclic aryl groups. For example, the aryl groups in the above arylamine groups may be selected from the examples of the above aryl groups.

[0067] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups. The heteroarylamine groups containing two or more of the above heteroaryl groups may contain monocyclic heteroaryl groups, polycyclic heteroaryl groups, or may contain both monocyclic heteroaryl groups and polycyclic heteroaryl groups. For example, the heteroaryl groups in the above heteroarylamine groups may be selected from the examples of the above heteroaryl groups.

[0068] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, the aromatic hydrocarbon ring group is applicable to the description of the above-mentioned aryl group, and the aliphatic hydrocarbon ring group is applicable to the description of the above-mentioned cycloalkyl group. In addition, the condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring may be applicable to a structure in which the above-mentioned aryl group and cycloalkyl group are condensed with each other.

[0069] In the present specification, an arylene group refers to a group having two bonding positions on an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

[0070] Unless otherwise defined in this specification, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Methods and materials similar to or equivalent to the description in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference, and in the case of conflict, if no specific passage is mentioned, the present specification including the definition takes precedence. In addition, materials, methods and embodiments are only illustrative and not intended to be limited.

[0071] Next, the compound of the above Chemical Formula 1 will be described in detail.

[0072] According to one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.

[0073] [Chemical formula 1-1]

[0074]

[0075] [Chemical formula 1-2]

[0076]

[0077] [Chemical formula 1-3]

[0078]

[0079] [Chemical formula 1-4]

[0080]

[0081] In the above chemical formulas 1-1 to 1-4,

[0082] Definitions of X1 to X3, L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in the above Chemical Formula 1.

[0083] According to one embodiment of the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 2-1 to 2-5.

[0084] [Chemical formula 2-1]

[0085]

[0086] [Chemical formula 2-2]

[0087]

[0088] [Chemical formula 2-3]

[0089]

[0090] [Chemical formula 2-4]

[0091]

[0092] [Chemical formula 2-5]

[0093]

[0094] In the above chemical formulas 2-1 to 2-5,

[0095] Definitions of L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in the above Chemical Formula 1.

[0096] According to one embodiment of the present specification, G1 to G4 are hydrogen.

[0097] According to one embodiment of the present specification, G1 to G4 are deuterium.

[0098] According to one embodiment of the present specification, the above G1 to G4 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0099] According to one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 3.

[0100] [Chemical formula 3]

[0101]

[0102] In the above chemical formula 3,

[0103] Definitions of X1 to X3, L1 to L3, Ar1 and R1 to R3 are the same as those in the above Chemical Formula 1.

[0104] According to one embodiment of the present specification, the above Chemical Formula 1-1 is any one of the following Chemical Formulas 1-1-1 to 1-1-5.

[0105] [Chemical formula 1-1-1]

[0106]

[0107] [Chemical formula 1-1-2]

[0108]

[0109] [Chemical formula 1-1-3]

[0110]

[0111] [Chemical formula 1-1-4]

[0112]

[0113] [Chemical formula 1-1-5]

[0114]

[0115] In the above chemical formulas 1-1-1 to 1-1-5,

[0116] Definitions of L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in the above Chemical Formula 1.

[0117] According to one embodiment of the present specification, the above Chemical Formula 1-2 is any one of the following Chemical Formulas 1-2-1 to 1-2-5.

[0118] [Chemical formula 1-2-1]

[0119]

[0120] [Chemical formula 1-2-2]

[0121]

[0122] [Chemical formula 1-2-3]

[0123]

[0124] [Chemical formula 1-2-4]

[0125]

[0126] [Chemical formula 1-2-5]

[0127]

[0128] In the above chemical formulas 1-2-1 to 1-2-5,

[0129] Definitions of L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in the above Chemical Formula 1.

[0130] According to one embodiment of the present specification, the above Chemical Formula 1-3 is any one of the following Chemical Formulas 1-3-1 to 1-3-5.

[0131] [Chemical formula 1-3-1]

[0132]

[0133] [Chemical formula 1-3-2]

[0134]

[0135] [Chemical formula 1-3-3]

[0136]

[0137] [Chemical formula 1-3-4]

[0138]

[0139] [Chemical formula 1-3-5]

[0140]

[0141] In the above chemical formulas 1-3-1 to 1-3-5,

[0142] Definitions of L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in the above Chemical Formula 1.

[0143] According to one embodiment of the present specification, the above Chemical Formula 1-4 is any one of the following Chemical Formulas 1-4-1 to 1-4-5.

[0144] [Chemical formula 1-4-1]

[0145]

[0146] [Chemical formula 1-4-2]

[0147]

[0148] [Chemical formula 1-4-3]

[0149]

[0150] [Chemical formula 1-4-4]

[0151]

[0152] [Chemical formula 1-4-5]

[0153]

[0154] In the above chemical formulas 1-4-1 to 1-4-5,

[0155] Definitions of L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in the above Chemical Formula 1.

[0156] According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a directly bonded, or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0157] According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a directly bonded, or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0158] According to one embodiment of the present specification, the above-mentioned L1 to L3 are the same as or different from each other, and are independently directly bonded; or are substituted or unsubstituted with deuterium, a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0159] According to one embodiment of the present specification, the above-mentioned L1 to L3 are the same as or different from each other, and are independently directly bonded; or are substituted or unsubstituted by deuterium, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0160] According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0161] According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0162] According to one embodiment of the present specification, the above L1 to L3 are the same as or different from each other, and are each independently any one of the following structures.

[0163]

[0164]

[0165] In the above structure,

[0166] Q1 and Q2 are the same as or different from each other and are each independently deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms. The dotted line indicates a connecting site.

[0167] According to one embodiment of the present specification, Q1 and Q2 are the same or different and are each independently deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms.

[0168] According to one embodiment of the present specification, Q1 and Q2 are the same as or different from each other, and are each independently deuterium, phenyl or methyl.

[0169] According to one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, or a naphthylene group.

[0170] According to one embodiment of the present specification, the above-mentioned L1 is a direct bond.

[0171] According to one embodiment of the present specification, the above-mentioned L2 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0172] According to one embodiment of the present specification, the above-mentioned L2 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0173] According to one embodiment of the present specification, the above-mentioned L2 is a direct bond, a phenylene group, or a naphthylene group.

[0174] According to one embodiment of the present specification, L3 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0175] According to one embodiment of the present specification, L3 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0176] According to one embodiment of the present specification, the above-mentioned L3 is a phenylene group.

[0177] According to one embodiment of the present specification, the above R1 to R3 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0178] According to one embodiment of the present specification, the above R1 to R3 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0179] According to one embodiment of the present specification, the above R1 to R3 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms.

[0180] According to one embodiment of the present specification, the above-mentioned R1 to R3 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms.

[0181] According to one embodiment of the present specification, the above R1 to R3 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0182] According to one embodiment of the present specification, the above R1 to R3 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0183] According to one embodiment of the present specification, R1 to R3 are phenyl groups.

[0184] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0185] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0186] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, which is substituted or unsubstituted with deuterium, a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, a monocyclic or polycyclic heteroaromatic group having 2 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms.

[0187] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, which is substituted or unsubstituted with deuterium, a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, a monocyclic or polycyclic heteroaromatic group having 2 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms.

[0188] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0189] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0190] According to one embodiment of the present specification, Ar1 is any one of the following structures.

[0191]

[0192]

[0193] In the above structure,

[0194] Q3 and Q4 are the same as or different from each other and are each independently deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms. The dotted line indicates the connection site.

[0195] According to one embodiment of the present specification, Q3 and Q4 are the same or different and are each independently deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms.

[0196] According to one embodiment of the present specification, Q3 and Q4 are the same as or different from each other, and are each independently deuterium, phenyl or methyl.

[0197] According to one embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a triphenylene group, a substituted or unsubstituted fluorenyl group, and a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0198] According to one embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a triphenylene group, a substituted or unsubstituted fluorenyl group, and a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0199] According to one embodiment of the present specification, Ar1 is a phenyl group which may be substituted with a dibenzofuranyl group or a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group which may be substituted with a methyl group, or a triphenylene group.

[0200] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.

[0211] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0212] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0213] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. According to one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0214] In this specification, the meaning of specific substance A contained in layer B includes i) the case where one or more substances A are contained in one layer B, and ii) the case where layer B is composed of one or more layers and substance A is contained in one or more layers of the multiple layers B.

[0215] In this specification, the meaning of a specific substance A being contained in layer C or layer D refers to all of the following situations: i) being contained in one or more layers among one or more layers C, or ii) being contained in one or more layers among one or more layers D, or iii) being contained in one or more layers C and one or more layers D, respectively.

[0216] The present specification provides an organic light-emitting device, comprising: a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers contains the compound of Chemical Formula 1.

[0217] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure, but may also be formed by a multi-layer structure in which two or more organic layers are stacked. For example, it may 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, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0218] According to one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

[0219] According to one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

[0220] According to one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0221] According to one embodiment of the present specification, the organic layer includes a light-emitting layer.

[0222] According to one embodiment of the present specification, the organic layer includes an electron blocking layer.

[0223] According to one embodiment of the present specification, the above-mentioned organic layer also includes one or more layers of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0224] According to one embodiment of the present specification, the above-mentioned organic light-emitting device also includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0225] According to one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode arranged opposite to the first electrode; a light-emitting layer arranged between the first electrode and the second electrode; and two or more organic layers arranged between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0226] According to one embodiment of the present specification, the above-mentioned two or more organic layers can be selected from two or more of the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0227] According to one embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different substances.

[0228] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0229] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0230] According to one embodiment of the present specification, the organic light emitting device may be a (normal type) organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0231] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0232] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is shown in Figure 1 and 2 . The above Figure 1 and 2 An organic light emitting device is exemplified, and is not limited thereto.

[0233] exist Figure 1 exemplifies the structure of an organic light-emitting device in which a first electrode 2, an organic layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The above-mentioned compound is contained in the organic layer.

[0234] exist Figure 2 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 3 are sequentially stacked on a substrate 1. The above compound is contained in the hole blocking layer 9 or the electron injection and transport layer 10.

[0235] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer includes the above compound, ie, the compound of the above Chemical Formula 1.

[0236] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0237] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0238] In addition, the compound of the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited thereto.

[0239] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to this.

[0240] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0241] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function, such as metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0242] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0243] According to one embodiment of the present specification, the host includes a compound represented by the following chemical formula H-1, but is not limited thereto.

[0244] [Chemical formula H-1]

[0245]

[0246] In the above chemical formula H-1,

[0247] L20 and L21 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0248] Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0249] 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,

[0250] r201 is an integer of 1 to 8. When r201 is 2 or more, two or more R201s are the same as or different from each other.

[0251] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0252] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0253] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0254] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0255] In one embodiment of the present specification, the above-mentioned Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted by deuterium, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted by deuterium, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted by a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms; a dibenzofuranyl group substituted or unsubstituted by a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted by a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms; a dibenzothienyl group substituted or unsubstituted by a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms; or a naphthobenzothienyl group substituted or unsubstituted by a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0256] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a phenanthryl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group, or a naphthiobenzothiophenyl group.

[0257] In one embodiment of the present specification, the Ar20 is a substituted or unsubstituted heterocyclic group, and the Ar21 is a substituted or unsubstituted aryl group.

[0258] According to one embodiment of the present specification, the above R201 is hydrogen or phenyl.

[0259] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0260]

[0261] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0262] According to one embodiment of the present specification, the dopant is represented by the following chemical formula D-1, but is not limited thereto.

[0263] [Chemical formula D-1]

[0264]

[0265] In the above chemical formula D-1,

[0266] T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted aryl group,

[0267] t3 and t4 are each an integer from 1 to 4,

[0268] t5 is an integer from 1 to 3,

[0269] When the above t3 is 2 or more, the above two or more T3 are the same or different from each other.

[0270] When the above t4 is 2 or more, the above two or more T4 are the same or different from each other.

[0271] When the above t5 is 2 or more, the above two or more T5s may be the same as or different from each other.

[0272] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0273] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other and are 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 arylamine group having 6 to 30 carbon atoms which is unsubstituted or substituted by 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 which is unsubstituted or substituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms or a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms.

[0274] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen; methyl; tert-butyl; diphenylamino substituted or unsubstituted by methyl or tert-butyl; trimethylsilyl; phenyl substituted or unsubstituted by methyl, tert-butyl or trimethylsilyl; or biphenyl.

[0275] According to one embodiment of the present specification, the chemical formula D-1 is selected from any one of the following compounds.

[0276]

[0277] According to one embodiment of the present specification, the chemical formula D-1 can be produced as shown in the following reaction formula 1, but is not limited thereto.

[0278] [Reaction 1]

[0279]

[0280] In the above reaction formula 1,

[0281] The definitions of T1 to T5 and t3 to t5 are the same as those in the above Chemical Formula D-1.

[0282] The 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, has the effect of receiving holes from the anode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; anthraquinone, polyaniline, and polythiophene conductive polymers, etc., but are not limited to these.

[0283] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0284] [Chemical formula HI-1]

[0285]

[0286] In the above chemical formula HI-1,

[0287] R315 to R317 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0288] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0289] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.

[0290] According to one embodiment of the present specification, the above R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0291] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazolyl group, a phenyl group, a biphenyl group, a triphenylene group, and a combination thereof.

[0292] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0293] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently phenyl or biphenyl, or are combined with adjacent groups to form an indene substituted with a methyl group.

[0294] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0295]

[0296] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2, but the present invention is not limited thereto.

[0297] [Chemical formula HI-2]

[0298]

[0299] In the above chemical formula HI-2,

[0300] R401 to R403 are the same as or different from each other and are each independently a halogen group,

[0301] R401 to R403 are 4.

[0302] According to one embodiment of the present specification, R401 to R403 are F.

[0303] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0304]

[0305] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.

[0306] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2 at a weight ratio of 1:99 to 99:1.

[0307] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, preferably a material with a large mobility for holes. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0308] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0309] [Chemical formula HT-1]

[0310]

[0311] In the above chemical formula HT-1,

[0312] L501 and L502 are the same as or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0313] R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0314] According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0315] According to one embodiment of the present specification, L501 and L502 are phenylene groups.

[0316] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0317] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a phenyl group or a naphthyl group.

[0318] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0319]

[0320] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. When the organic light-emitting device according to one embodiment of the present specification includes another electron transport layer in addition to the electron transport layer comprising the above chemical formula 1, the electron transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a substance with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes comprising Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common substance having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0321] The electron injection layer is a layer that receives electrons from an electrode. When the organic light-emitting device according to one embodiment of the present specification includes another electron injection layer in addition to the electron injection layer comprising the above chemical formula 1, the electron injection material is preferably a material that has excellent ability to transport electrons, has the effect of receiving electrons from the second electrode, and has an excellent electron injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferably a material that prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0322] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, 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.

[0323] According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the electron injection and transport layer includes another electron injection and transport layer other than the electron injection and transport layer including the above-mentioned chemical formula 1, the substances exemplified in the above-mentioned electron transport layer and electron injection layer can be used, but are not limited thereto.

[0324] According to one embodiment of the present specification, the electron injection and transport layer includes a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0325] [Chemical formula ET-1]

[0326]

[0327] In the above chemical formula ET-1,

[0328] At least one of Z11 to Z13 is N, and the rest are CH,

[0329] At least one of Z21 to Z23 is N, and the others are CH,

[0330] L601 and L602 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0331] Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0332] According to one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0333] According to one embodiment of the present specification, L601 and L602 are phenylene groups.

[0334] According to one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0335] According to one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0336] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0337]

[0338] According to one embodiment of the present specification, the electron injection and transport layer may further include a metal coordination compound. The metal coordination compound is as described above.

[0339] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and the substances exemplified in the description of the hole injection layer can be used, but are not limited thereto. The electron blocking layer can be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0340] As a material for the electron blocking layer, the example of the chemical formula HI-I can be used, but it is not limited thereto.

[0341] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed using the same conditions as the electron injection layer. When the organic light-emitting device according to one embodiment of the present specification includes another hole blocking layer in addition to the hole blocking layer comprising the above chemical formula 1, specifically, Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0342] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0343] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0344] Modes for Carrying Out the Invention

[0345] Below, in order to specifically describe this specification, examples and comparative examples will be cited for detailed description. However, the examples and comparative examples of this specification can be deformed into various forms, and it is not interpreted that the scope of this specification is limited to the examples and comparative examples described in detail below. The examples and comparative examples of this specification are provided to more completely describe this specification to those skilled in the art.

[0346] <Production Example 1> Synthesis of Compound 1

[0347]

[0348] In a 500 ml round-bottom flask under a nitrogen atmosphere, the compounds 2-chloro-4-phenyl-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine (2-chloro-4-phenyl-6-(4-(triphenylsilyl)phen yl)-1,3,5-triazine) (6.50 g, 16.50 mmol) and a-1 (7.24, 15.28 mmol) were completely dissolved in 240 ml of tetrahydrofuran, and then a 2M potassium carbonate aqueous solution (120 ml) was added. After adding tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 330 ml of ethyl acetate to produce compound 1 (6.66 g, 59%).

[0349] MS[M+H] + =823

[0350] <Production Example 2> Synthesis of Compound 2

[0351]

[0352] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-phenyl-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine (6.50 g, 16.50 mmol) and compound a-2 (8.03 g, 18.15 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of ethyl acetate to produce compound 2 (7.11 g, 62%).

[0353] MS[M+H] + =823

[0354] <Production Example 3> Synthesis of Compound 3

[0355]

[0356] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-phenyl-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine (6.50 g, 13.83 mmol) and compound a-3 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 320 mL of tetrahydrofuran to produce compound 3 (7.25 g, 68%).

[0357] MS[M+H] + =823

[0358] <Production Example 4> Synthesis of Compound 4

[0359]

[0360] Under nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and compound a-1 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then a 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol), the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to produce compound 4 (6.99 g, 66%).

[0361] MS[M+H] + =766

[0362] <Production Example 5> Synthesis of Compound 5

[0363]

[0364] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (6.50 g, 13.83 mmol) and compound a-2 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to produce compound 5 (7.27 g, 69%).

[0365] MS[M+H] + =766

[0366] <Production Example 6> Synthesis of Compound 6

[0367]

[0368] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (6.50 g, 13.83 mmol) and compound a-3 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 mL of ethyl acetate to produce compound 6 (6.24 g, 59%).

[0369] MS[M+H] + =766

[0370] <Production Example 7> Synthesis of Compound 7

[0371]

[0372] Under nitrogen atmosphere, in a 500 ml round-bottom flask, the compounds 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and a-1 (7.24 g, 15.24 mmol) were completely dissolved in 240 ml of tetrahydrofuran, and then a 2M aqueous potassium carbonate solution (120 ml) was added. After adding tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 240 mL of ethyl acetate to produce Compound 7 (6.68 g, 63%).

[0373] MS[M+H] + =899

[0374] <Production Example 8> Synthesis of Compound 8

[0375]

[0376] Under nitrogen atmosphere, in a 500 ml round-bottom flask, the compounds 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and a-2 (7.24 g, 15.28 mmol) were completely dissolved in 240 ml of tetrahydrofuran, and then a 2M aqueous potassium carbonate solution (120 ml) was added. After adding tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310 ml of ethyl acetate to produce Compound 8 (7.05 g, 67%).

[0377] MS[M+H] + =899

[0378] <Production Example 9> Synthesis of Compound 9

[0379]

[0380] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and compound a-3 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 290 mL of ethyl acetate to produce Compound 9 (6.33 g, 60%).

[0381] MS[M+H] + =899

[0382] <Production Example 10> Synthesis of Compound 10

[0383]

[0384] Under nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 2-chloro-4-(2-(dibenzo[b,d]furan-2-yl)phenyl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (6.50 g, 13.43 mmol) and compound a-1 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 320 mL of ethyl acetate to produce Compound 10 (6.81 g, 65%).

[0385] MS[M+H] + =989

[0386] <Production Example 11> Synthesis of Compound 11

[0387]

[0388] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-(2-(dibenzo[b,d]thiophen-2-yl)phenyl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (6.50 g, 13.01 mmol) and compound a-1 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 270 mL of ethyl acetate to produce Compound 11 (6.22 g, 60%).

[0389] MS[M+H] + =1005

[0390] <Production Example 12> Synthesis of Compound 12

[0391]

[0392] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-(naphthalen-1-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-chloro-4-(naphthalen-1-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and compound a-1 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to produce compound 12 (6.99 g, 66%).

[0393] MS[M+H] + =873

[0394] <Production Example 13> Synthesis of Compound 13

[0395]

[0396] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-(naphthalen-2-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-chloro-4-(naphthalen-2-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and compound a-2 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to produce compound 13 (7.27 g, 69%).

[0397] MS[M+H] + =873

[0398] <Production Example 14> Synthesis of Compound 14

[0399]

[0400] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 2-chloro-4-(phenanthren-9-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2-chloro-4-(phenanthren-9-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine) (6.50 g, 13.83 mmol) and compound a-3 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and then heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310 mL of ethyl acetate to produce compound 14 (6.24 g, 59%).

[0401] MS[M+H] + =923

[0402] Example 1-1

[0403] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0404] On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio) and A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The EB1 compound is vacuum-deposited to form an electron blocking layer. Next, a film having a thickness of The compound represented by the following chemical formula BH and the compound represented by the following chemical formula BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer. The compound represented by compound 1 synthesized in the above-mentioned manufacturing example 1 was vacuum-deposited to form a hole blocking layer. Next, on the above-mentioned hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1, thereby On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by vapor deposition of a thickness of .

[0405]

[0406] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 Holder~5×10 -6 A support is provided to produce an organic light-emitting device.

[0407] Example 1-2 to Example 1-14

[0408] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of the compounds in Manufacturing Example 1.

[0409] Comparative Examples 1-1 to 1-9

[0410] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of the compounds in Preparation Example 1. The compounds HB1 to HB9 used in Table 1 below are as follows.

[0411]

[0412] Experimental Example 1

[0413] When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0414] [Table 1]

[0415]

[0416] As shown in Table 1 above, an organic light-emitting device using the compound of the present invention having a triazine substituent attached to a spiro[fluorene-9,9'-xanthene] Core as a hole blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and stability of the organic light-emitting device. Specifically, it can be seen that in the compounds of Examples 1-1 to 1-14 according to one embodiment of the present specification, any one of the 1' to 4' positions of the spirofluorene-9,9'-xanthene nucleus is a monocyclic N-containing six-membered heterocyclic ring substituted by -L3-SiR1R2R3 (silyl group), and the organic light-emitting devices of the above Examples 1-1 to 1-14 are compared with the organic light-emitting devices of Comparative Examples 1-1 to 1-6 using compounds not bonded with silyl groups and the organic light-emitting devices of Comparative Examples 1-7 to 1-9 containing compounds containing any one of the 1' to 4 positions of the spirofluorene-9,9'-xanthene nucleus containing a monocyclic N-containing six-membered heterocyclic ring substituted by -L3-SiR1R2R3 (silyl group), and have low driving voltage and significantly excellent efficiency and life.

[0417] The preferred embodiment (hole blocking layer) of the present invention is described above, but the present invention is not limited thereto and can be implemented in various forms within the scope of the claimed protection and the detailed description of the invention, which also belongs to the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, At least one of X1 to X3 is N, and the others are CH, L1 to L3 are the same or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group, R1 to R3 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, G1 to G4 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group, g1 is an integer from 1 to 3. When g1 is 2 or more, two or more G1 are the same or different from each other. g2 to g4 are each an integer from 1 to 4, When the g2 is 2 or more, the two or more G2 are the same or different from each other. When the g3 is 2 or more, the two or more G3 are the same or different from each other. When the number of g4 is 2 or more, the two or more G4's are the same as 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 1-4: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In the chemical formulas 1-1 to 1-4, Definitions of X1 to X3, L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in Chemical Formula 1.

3. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 2-1 to 2-5: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] In the chemical formulas 2-1 to 2-5, Definitions of L1 to L3, Ar1, R1 to R3, G1 to G4, and g1 to g4 are the same as those in Chemical Formula 1.

4. The compound according to claim 1, wherein The L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

5. The compound according to claim 1, wherein The R1 to R3 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

6. The compound according to claim 1, wherein Ar1 is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

7. The compound according to claim 1, wherein The chemical formula 1 is any one of the following compounds:

8. An organic light-emitting device, wherein: include: A first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 7.

9. The organic light emitting device according to claim 8, wherein: The organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

10. The organic light emitting device according to claim 8, wherein: The organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

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