Organic light emitting device

Abstract

The present specification provides an organic light-emitting device comprising a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0144670 filed in the Korean Intellectual Property Office on November 2, 2022, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to organic light emitting devices. Background Art

[0003] The organic light-emitting phenomenon generally refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in many cases, the organic material layer has a multilayer structure composed of different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0004] There is a continuing need to develop new materials for use in the above-mentioned organic light-emitting devices. Summary of the invention

[0005] Technical issues

[0006] The present specification is directed to providing an organic light emitting device.

[0007] Technical Solution

[0008] An exemplary embodiment of the present specification provides an organic light emitting device including: an anode; a cathode; and a first organic material layer disposed between the anode and the cathode, wherein the first organic material layer includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2.

[0009] [Chemical formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] X1 is O or S,

[0013] Cy1 is a substituted or unsubstituted dibenzofuran; or a substituted or unsubstituted dibenzothiophene,

[0014] L1 is a direct bond; or a substituted or unsubstituted arylene group,

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

[0016] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0017] n1 is an integer of 0 to 8, and when n1 is 2 or more, two or more R1s are the same as or different from each other, and

[0018] n2 is an integer of 0 to 4, and when n2 is 2 or more, two or more R2s are the same as or different from each other.

[0019] [Chemical formula 2]

[0020]

[0021] In chemical formula 2,

[0022] L2 is a direct bond; or a substituted or unsubstituted arylene group,

[0023] Ar2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0024] Z1 is hydrogen; deuterium; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0025] m1 is an integer of 0 to 8, and when m1 is 2 or more, two or more Z1 are the same as or different from each other, and

[0026] Ar3 is the following chemical formula A, and Z10 or Z11 of the following chemical formula A is connected to L2 of chemical formula 2,

[0027] [Chemical formula A]

[0028]

[0029] In chemical formula A,

[0030] X2 is O or S,

[0031] Cy2 is substituted or unsubstituted benzene; or substituted or unsubstituted naphthalene, and

[0032] The group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0033] Beneficial Effects

[0034] The organic light emitting device described in the present specification has the effects of low driving voltage, high efficiency and / or long lifetime by including both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 in the first organic material layer. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 An example of an organic light-emitting device is shown in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially stacked.

[0036] [Description of Reference Numerals and Symbols]

[0037] 1: Base

[0038] 2: Anode

[0039] 3: Hole injection layer

[0040] 4: Hole transport layer

[0041] 5: Electron blocking layer

[0042] 6: Luminous layer

[0043] 7: Hole blocking layer

[0044] 8: Electron transport layer

[0045] 9: Electron injection layer

[0046] 10: Cathode DETAILED DESCRIPTION

[0047] Hereinafter, the present specification will be described in more detail.

[0048] In the present specification, when a part “includes” a constituent element, unless specifically described otherwise, this does not mean excluding the other constituent elements but means that the other constituent elements may further be included.

[0049] In this specification, when one member is disposed “on” another member, this includes not only a case where one member is in contact with the other member but also a case where another member is present between the two members.

[0050] In the present specification, the deuterium substitution rate of a compound can be understood by the following methods: a method of calculating the substitution rate based on the maximum value of the distribution formed by the molecular weight at the end point of the reaction using thin layer chromatography / mass spectrometry (TLC-MS) or a quantitative analysis method using NMR; and a method of adding DMF as an internal standard and calculating the D-substitution rate based on the integrated amount of the total peak using the integral rate on 1H NMR.

[0051] In this specification, "energy level" means the magnitude of energy. Therefore, the energy level is interpreted as meaning the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in the negative direction from the vacuum energy level.

[0052] In this specification, the highest occupied molecular orbital (HOMO) means a molecular orbital in the highest energy region in which electrons can participate in bonding (highest occupied molecular orbital), the lowest unoccupied molecular orbital (LUMO) means a molecular orbital in the lowest energy region in which electrons exist in the antibonding region (lowest unoccupied molecular orbital), and the HOMO energy level means the distance from the vacuum energy level to the HOMO. In addition, the LUMO energy level means the distance from the vacuum energy level to the LUMO.

[0053] In this specification, the band gap means the energy level difference between HOMO and LUMO, that is, the HOMO-LUMO gap (gap).

[0054] In this specification, the HOMO level can be measured using a photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3) under the atmosphere, and the LUMO level can be calculated from a wavelength value measured by photoluminescence (PL).

[0055] Examples of the substituent in the present specification will be described below, but are not limited thereto.

[0056] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substitutions are made, the two or more substituents may be the same or different from each other.

[0057] In the present invention, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the following: deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; alkenyl group; silyl group; boron group; amine group; aryl group; or heterocyclic group, substituted with a substituent in which two or more substituents are connected among the exemplified substituents, or having no substituent. For example, "a substituent in which two or more substituents are connected" can be a biphenyl group. That is, the biphenyl group can also be an aryl group, and can be interpreted as a substituent in which two phenyl groups are connected.

[0058] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the following: deuterium; a halogen group; a cyano group; a silyl group; an alkoxy group; an aryloxy group; an alkyl group; an aryl group; and a heterocyclic group, substituted with a substituent in which two or more substituents among the exemplified substituents are linked, or having no substituent.

[0059] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium; an alkyl group; an aryl group; and a heterocyclic group, substituted with a substituent in which two or more substituents among the exemplified substituents are linked, or having no substituent.

[0060] Examples of the substituent will be described below, but are not limited thereto.

[0061] In the present specification, examples of the halogen group include fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0062] In the present specification, the silyl group may be represented by the formula -SiYaYbYc, and Ya, Yb, and Yc may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0063] In the present specification, the boron group can be represented by the formula -BYdYe, and Yd and Ye can each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the boron group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited thereto.

[0064] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0065] In the present specification, the above description of the alkyl group may be applied to the arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

[0066] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0067] Alkyl, alkoxy and other alkyl moiety-containing substituents described in this specification include both straight-chain and branched forms.

[0068] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, phenyl group, styryl group, etc., but are not limited thereto.

[0069] In the present specification, the alkynyl group as a substituent including a triple bond between carbon atoms may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 10.

[0070] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0071] In the present specification, the amine group is -NH2, and the amine group may be substituted by the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, combination thereof, etc. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the number of carbon atoms of the amine group is 1 to 20. According to an exemplary embodiment, the number of carbon atoms of the amine group is 1 to 10. Specific examples of the substituted amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, 9,9-dimethylfluorenylphenylamine, pyridylphenylamine, diphenylamine, phenylpyridylamine, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamine, 9-methylanthrylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, diphenylamine, etc., but are not limited thereto.

[0072] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, quaterphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, phenylene, fluorenyl, triphenylene, etc., but not limited thereto.

[0073] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure.

[0074] When the fluorenyl group is substituted, the substituent may be a spirofluorenyl group such as and substituted fluorenyl groups such as (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) However, the fluorenyl group is not limited thereto.

[0075] In the present specification, the above description of the aryl group can be applied to the aryl group in the aryloxy group.

[0076] In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.

[0077] In the present specification, the above description of the heterocyclic group can be applied to the heteroaryl group, except that the heteroaryl group is aromatic.

[0078] In this specification, the description of the aryl group can be applied to the arylene group, except that the arylene group is divalent.

[0079] In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from examples of a cycloalkyl group or an aryl group.

[0080] In the present specification, an aliphatic hydrocarbon ring means a ring consisting of only carbon atoms and hydrogen atoms as a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc., but are not limited thereto.

[0081] In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon atoms and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, Pentacene, fluorene, indene, acenaphthene, benzofluorene, spirofluorene, etc., but not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

[0082] In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include ethylene oxide, tetrahydrofuran, 1,4-dihydrofuran, The present invention also includes, but is not limited to, oxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, thiocane, and the like.

[0083] In the present specification, an aromatic heterocycle means an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazines, Azine, thiazine, di Indole, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but not limited thereto.

[0084] Hereinafter, a preferred exemplary embodiment of the present invention will be described in detail. However, the exemplary embodiment of the present invention may be modified into various other forms, and the scope of the present invention is not limited to the exemplary embodiment to be described below.

[0085] The organic light emitting device of the present invention is characterized by comprising a first organic material layer containing both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2. Since the compound represented by Chemical Formula 1 has an effect of improving the injection of electrons, the compound exhibits an effect of improving the driving voltage when applied to the device, and since the compound represented by Chemical Formula 2 has high efficiency characteristics when applied to the device, when both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are used, the effects of improving both the driving voltage and the efficiency can be obtained.

[0086] Hereinafter, Chemical Formula 1 will be described in detail.

[0087] [Chemical formula 1]

[0088]

[0089] In Chemical Formula 1,

[0090] X1 is O or S,

[0091] Cy1 is a substituted or unsubstituted dibenzofuran; or a substituted or unsubstituted dibenzothiophene,

[0092] L1 is a direct bond; or a substituted or unsubstituted arylene group,

[0093] Ar1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0094] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0095] n1 is an integer of 0 to 8, and when n1 is 2 or more, two or more R1s are the same as or different from each other, and

[0096] n2 is an integer of 0 to 4, and when n2 is 2 or more, two or more R2s are the same as or different from each other.

[0097] According to an exemplary embodiment of the present specification, X1 is O or S.

[0098] According to an exemplary embodiment of the present specification, Cy1 is a substituted or unsubstituted dibenzofuran.

[0099] In another exemplary embodiment, Cy1 is unsubstituted or deuterium-substituted dibenzofuran.

[0100] According to an exemplary embodiment of the present specification, Cy1 is substituted or unsubstituted dibenzothiophene.

[0101] In an exemplary embodiment of the present specification, Cy1 is unsubstituted or deuterium-substituted dibenzothiophene.

[0102] In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6.

[0103] [Chemical formula 1-1]

[0104]

[0105] [Chemical formula 1-2]

[0106]

[0107] [Chemical formula 1-3]

[0108]

[0109] [Chemical formula 1-4]

[0110]

[0111] [Chemical formula 1-5]

[0112]

[0113] [Chemical formula 1-6]

[0114]

[0115] In Chemical Formulas 1-1 to 1-6,

[0116] The definitions of X1, R1, R2, n1, n2, L1 and Ar1 are the same as those in Chemical Formula 1, X1' is O or S,

[0117] R3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and

[0118] n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other.

[0119] According to an exemplary embodiment of the present specification, X1' is O or S.

[0120] According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0121] According to another exemplary embodiment, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0122] According to yet another exemplary embodiment, L1 is a direct bond.

[0123] In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0124] According to another exemplary embodiment, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0125] According to yet another exemplary embodiment, Ar1 is an unsubstituted or deuterium-substituted aryl group having 6 to 30 carbon atoms; or an unsubstituted or deuterium-substituted heteroaryl group having 2 to 30 carbon atoms.

[0126] According to still another exemplary embodiment, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0127] In another exemplary embodiment, Ar1 is substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted fluorenyl; substituted or unsubstituted fluoranyl; substituted or unsubstituted triphenylene; substituted or unsubstituted benzofuranyl; substituted or unsubstituted benzothiophenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted naphthobenzofuranyl; substituted or unsubstituted carbazolyl; or a combination thereof.

[0128] In another exemplary embodiment, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted fluoranyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted benzothienyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted naphthobenzofuranyl group; a substituted or unsubstituted carbazolyl group; or a combination thereof. In this case, the substituent may be unsubstituted or deuterium substituted.

[0129] According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0130] According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0131] According to yet another exemplary embodiment, R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0132] According to an exemplary embodiment of the present specification, R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0133] According to another exemplary embodiment, R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0134] According to yet another exemplary embodiment, R3 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0135] According to an exemplary embodiment of the present specification, n1 is an integer of 0 to 8, and when n1 is 2 or more, two or more R1s are the same as or different from each other.

[0136] According to an exemplary embodiment of the present specification, n2 is an integer of 0 to 4, and when n2 is 2 or more, two or more R2 are the same as or different from each other.

[0137] According to an exemplary embodiment of the present specification, n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other.

[0138] In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following compounds:

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Hereinafter, Chemical Formula 2 will be described in detail.

[0170] [Chemical formula 2]

[0171]

[0172] In chemical formula 2,

[0173] L2 is a direct bond; or a substituted or unsubstituted arylene group,

[0174] Ar2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0175] Z1 is hydrogen; deuterium; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0176] m1 is an integer of 0 to 8, and when m1 is 2 or more, two or more Z1 are the same as or different from each other, and

[0177] Ar3 is the following chemical formula A, and Z10 or Z11 of the following chemical formula A is connected to L2 of chemical formula 2,

[0178] [Chemical formula A]

[0179]

[0180] In chemical formula A,

[0181] X2 is O or S,

[0182] Cy2 is substituted or unsubstituted benzene; or substituted or unsubstituted naphthalene, and

[0183] The group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0184] According to an exemplary embodiment of the present specification, Ar3 is Chemical Formula A, and Z10 or Z11 of Chemical Formula A is connected to L2 of Chemical Formula 2.

[0185] According to an exemplary embodiment of the present specification, X2 is O or S.

[0186] According to an exemplary embodiment of the present specification, Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2.

[0187] [Chemical formula 2-1]

[0188]

[0189] [Chemical formula 2-2]

[0190]

[0191] In chemical formulas 2-1 and 2-2,

[0192] Definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and definitions of X2, Z10 to Z13 and Cy2 are the same as those in Chemical Formula A.

[0193] In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1-1 to 2-1-4.

[0194] [Chemical formula 2-1-1]

[0195]

[0196] [Chemical formula 2-1-2]

[0197]

[0198] [Chemical formula 2-1-3]

[0199]

[0200] [Chemical formula 2-1-4]

[0201]

[0202] In chemical formulas 2-1-1 to 2-1-4,

[0203] The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2 and Z10 to Z13 are the same as those in Chemical Formula A,

[0204] Z2 and Z3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0205] m2 is an integer from 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other, and

[0206] m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other.

[0207] In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-2-1 to 2-2-4.

[0208] [Chemical formula 2-2-1]

[0209]

[0210] [Chemical formula 2-2-2]

[0211]

[0212] [Chemical formula 2-2-3]

[0213]

[0214] [Chemical formula 2-2-4]

[0215]

[0216] In chemical formulas 2-2-1 to 2-2-4,

[0217] The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2, Z10, Z12 and Z13 are the same as those in Chemical Formula A,

[0218] Z2 and Z3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0219] m2 is an integer from 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other, and

[0220] m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other.

[0221] According to an exemplary embodiment of the present specification, L2 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0222] According to another exemplary embodiment, L2 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0223] According to yet another exemplary embodiment, L2 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0224] According to yet another embodiment, L2 is a direct bond; unsubstituted or deuterium-substituted phenylene; unsubstituted or deuterium-substituted biphenylene; or unsubstituted or deuterium-substituted naphthylene.

[0225] In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0226] According to yet another exemplary embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0227] According to a further exemplary embodiment, Ar2 is an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with one or more selected from deuterium and an aryl group; or a heteroaryl group having 2 to 30 carbon atoms which is unsubstituted or substituted with one or more selected from deuterium and an aryl group.

[0228] According to another further exemplary embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0229] According to yet another further exemplary embodiment, Ar2 is an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with one or more selected from deuterium and an aryl group.

[0230] According to still another exemplary embodiment, Ar2 is an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with one or more selected from deuterium and an aryl group having 6 to 30 carbon atoms.

[0231] In another exemplary embodiment, Ar2 is substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted triphenylene; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted pyrenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted benzofuranyl; substituted or unsubstituted benzothienyl; substituted or unsubstituted dibenzothienyl; substituted or unsubstituted fluoranthenyl; substituted or unsubstituted triphenylenyl; substituted or unsubstituted tetralin; substituted or unsubstituted carbazolyl; or a combination thereof. In this case, the substituent may be unsubstituted or deuterium substituted.

[0232] According to an exemplary embodiment of the present specification, Z1 is hydrogen; deuterium; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0233] According to another exemplary embodiment, Z1 is hydrogen; deuterium; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0234] According to yet another exemplary embodiment, Z1 is hydrogen; deuterium; or substituted or unsubstituted pentyl.

[0235] In an exemplary embodiment of the present specification, m1 is an integer of 0 to 8, and when m1 is 2 or more, two or more Z1 are the same as or different from each other.

[0236] In an exemplary embodiment of the present specification, the group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0237] According to an exemplary embodiment of the present specification, the group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0238] According to an exemplary embodiment of the present specification, the group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0239] According to an exemplary embodiment of the present specification, the group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0240] In an exemplary embodiment of the present specification, Z2 and Z3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0241] According to an exemplary embodiment of the present specification, Z2 and Z3 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0242] According to an exemplary embodiment of the present specification, Z2 and Z3 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0243] According to an exemplary embodiment of the present specification, Z2 and Z3 are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; or a combination thereof.

[0244] According to an exemplary embodiment of the present specification, m2 is an integer of 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other.

[0245] According to an exemplary embodiment of the present specification, m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other.

[0246] In an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of the following compounds.

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-1, and Chemical Formula 2 is represented by Chemical Formula 2-1-2.

[0300] According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-1, and Chemical Formula 2 is represented by Chemical Formula 2-1-3.

[0301] According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-1, and Chemical Formula 2 is represented by Chemical Formula 2-1-4.

[0302] According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-1, and Chemical Formula 2 is represented by Chemical Formula 2-2-4.

[0303] The core structure of the compound represented by Chemical Formula 1 and Chemical Formula 2 according to an exemplary embodiment of the present specification can be prepared as in the method of the preparation example to be described below. The substituent can be bonded by a method known in the art, and the type and position of the substituent or the number of the substituent can be changed according to a technique known in the art.

[0304] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compounds represented by Chemical Formula 1 and Chemical Formula 2. In addition, in the present specification, various substituents can be introduced into the core structure having the above structure to adjust the HOMO energy level and LUMO energy level of the compound.

[0305] Hereinafter, an organic light emitting device will be described.

[0306] In this specification, when one member is disposed “on” another member, this includes not only a case where one member is in contact with the other member but also a case where another member is present between the two members.

[0307] In the present specification, when a part “includes” a constituent element, unless specifically described otherwise, this does not mean excluding the other constituent elements but means that the other constituent elements may further be included.

[0308] The organic light emitting device is characterized by including: an anode; a cathode; and a first organic material layer disposed between the anode and the cathode, wherein the first organic material layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2.

[0309] The organic material layer of the organic light-emitting device of the present specification may be composed of a single-layer structure, but may also be composed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present specification may have a structure including one or more of the following layers as an organic material layer: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto, and may include fewer or more organic material layers.

[0310] In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer may be a hole transport layer, a hole injection layer, a hole transport and injection layer, or an electron blocking layer.

[0311] In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer may be a light emitting layer and may further include a dopant material. In this case, the compound of the above Chemical Formula 1 and the compound of Chemical Formula 2 are the host of the light emitting layer.

[0312] As an example of a dopant material, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, and a boron-based compound can be used, but the dopant material is not limited thereto. In this case, the dopant in the light-emitting layer is contained in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host.

[0313] In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer may be an electron transport layer, an electron injection layer, an electron transport and injection layer, or a hole blocking layer.

[0314] In the organic light-emitting device of the present specification, an organic material layer having one or more layers is also arranged between the anode and the cathode, and the organic material layer may further include one or more of the following layers: a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

[0315] In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer includes both the compound of Chemical Formula 1 and the compound of Chemical Formula 2, and the mass ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula 2 may be 90:10 to 10:90.

[0316] The structure of the organic light-emitting device of the present specification may have Figure 1 The structure is the same as the structure shown in, but is not limited to this.

[0317] Figure 1 The structure of an organic light-emitting device is illustrated in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially stacked. In the structure as described above, the first organic material layer of the present specification may be the light-emitting layer 6.

[0318] According to an exemplary embodiment of the present specification, an organic light emitting device may have a series structure in which two or more independent devices are connected in series. In an exemplary embodiment, the series structure may be in the form of each organic light emitting device being joined through a charge generation layer. Since a device having a series structure can be driven with a lower current than a current of a unit device based on the same brightness, there is an advantage of significantly improving the service life characteristics of the device.

[0319] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0320] The organic light emitting device of the present invention may be manufactured by a typical method and material for manufacturing an organic light emitting device, except that the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are used to form the first organic material layer.

[0321] According to an exemplary embodiment of the present specification, the first organic material layer including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be formed by a vacuum deposition method or a solution application method.

[0322] According to an exemplary embodiment of the present specification, the first organic material layer may be formed by co-deposition using each deposition source or by pre-mixed deposition using one deposition source. Co-deposition is to form the first organic material layer using a vapor deposition source containing a compound of Chemical Formula 1 and a vapor deposition source containing a compound of Chemical Formula 2, and pre-mixed deposition is to form the first organic material layer by mixing the compound of Chemical Formula 1 and the compound of Chemical Formula 2, placing the resulting mixture into one deposition source, and using the mixed deposition source. When an organic material layer containing the same compound is formed, pre-mixed deposition promotes interaction between the compounds compared to co-deposition, so that the effect of improving processability and improving the characteristics of the manufactured device can be obtained.

[0323] When manufacturing the organic light-emitting device of the present specification, the compound can be formed into an organic material layer not only by vacuum deposition but also by solution application method. Here, solution application method means spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0324] For example, the organic light-emitting device according to the present specification can be manufactured by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form an anode, forming an organic material layer including 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. on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0325] The organic material layer may further include one or more of the following layers: a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

[0326] The anode is an electrode for injecting holes, and as an anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of anode materials that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; 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.

[0327] The cathode is an electrode for injecting electrons, and as a cathode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material 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 alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0328] The hole injection layer is a layer that promotes the injection of holes from the anode to the light-emitting layer, and the hole injection material is preferably a material that can well receive holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include the above-mentioned compounds or metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, but are not limited thereto. The thickness of the hole injection layer can be 1nm to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the hole injection characteristic can be prevented from deteriorating, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the driving voltage can be increased to improve the movement of holes due to the hole injection layer being too thick.

[0329] The hole transport layer can play a role in promoting the transport of holes. The hole transport material is suitably a material with high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include the above-mentioned compounds or organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0330] A hole buffer layer may be additionally disposed between the hole injection layer and the hole transport layer, and the hole buffer layer may include the above-mentioned compound or a hole injection or transport material known in the art.

[0331] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer is a layer that can improve the service life and efficiency of the device by adjusting the holes transmitted from the hole transport layer so that the holes are smoothly injected into the light emitting layer, and preventing the electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. The above-mentioned compounds or materials known in the art may be used for the electron blocking layer. In particular, the electron blocking layer may include a compound in which a carbazolyl group and an arylamine group are connected to each other via an intermediate connecting group such as an arylene group or a heteroarylene group, and for example, it is more preferred that the electron blocking layer includes a compound represented by the following chemical formula 3, but the electron blocking layer is not limited thereto.

[0332] [Chemical formula 3]

[0333]

[0334] In chemical formula 3,

[0335] Ra and Rb are the same as or different from each other and are each independently hydrogen; deuterium; an alkyl group; an alkenyl group; an alkynyl group; a cycloalkyl group; an alkoxy group; an alkylthio group; an aryloxy group; an arylthio group; an aralkyl group; Si(R101)(R102)(R103); -C(=O)R104; -COOR105; a halogen atom; a cyano group; a nitro group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and Ra and Rb may each independently bond to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or heterocyclic ring,

[0336] R101 to R105 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0337] L3 to L6 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0338] Ar4 and Ar5 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,

[0339] p1 is an integer from 0 to 8, and when p1 is 2 or more, two or more Ra are the same as or different from each other, and

[0340] q1 is an integer of 0 to 4, and when q1 is 2 or more, two or more Rb are the same as or different from each other.

[0341] The light-emitting layer can emit red, green or blue light, and can be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0342] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0343] When the light-emitting layer emits red light, a phosphorescent material such as bis(1-phenylisoquinoline)iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline)iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr) or platinum octaethylporphyrin (PtOEP), or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as planar tris(2-phenylpyridine)iridium (Ir(ppy)3) or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3), anthracene-based compounds, pyrene-based compounds and boron-based compounds can be used as light-emitting dopants, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds and boron-based compounds can be used as light-emitting dopants, but the light-emitting dopants are not limited thereto.

[0344] A hole blocking layer may be provided between the electron transport layer and the light emitting layer. The hole blocking layer is a layer that can improve the service life and efficiency of the device by adjusting the electrons transmitted from the electron transport layer so that the electrons are smoothly injected into the light emitting layer, and preventing the holes injected from the hole injection layer from passing through the light emitting layer and entering the electron injection layer. The above-mentioned compounds or materials known in the art may be used for the hole blocking layer. In particular, it is more preferred that the hole blocking layer comprises a compound represented by the following chemical formula 4, but the hole blocking layer is not limited thereto.

[0345] [Chemical formula 4]

[0346]

[0347] In chemical formula 4,

[0348] Q is represented by the following chemical formula B or chemical formula C,

[0349] L7 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0350] Ar6 is represented by the following chemical formula D or chemical formula E,

[0351] r1 is an integer from 1 to 4,

[0352] [Chemical formula B]

[0353]

[0354] In chemical formula B,

[0355] Rc and Rd are the same as or different from each other and are each independently hydrogen; deuterium; nitrile; nitro; hydroxyl; carbonyl; ester; imide; amide; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkylsulfonyl; substituted or unsubstituted arylsulfonyl; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted boronyl; substituted or unsubstituted amine; substituted or unsubstituted arylphosphino; substituted or unsubstituted phosphine oxide; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0356] p2 is an integer from 0 to 7, and when p2 is 2 or more, two or more Rc are the same as or different from each other,

[0357] q2 is an integer from 0 to 8, and when q2 is 2 or more, two or more Rd are the same as or different from each other,

[0358] It means the position of bonding with chemical formula 4,

[0359] [Chemical formula C]

[0360]

[0361] In chemical formula C,

[0362] Re and Rf are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl, or are bonded to each other to form a substituted or unsubstituted ring,

[0363] Rg is hydrogen, deuterium, nitrile, nitro, hydroxyl, carbonyl, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0364] r2 is an integer from 0 to 7, and when r2 is 2 or more, two or more Rg are the same as or different from each other,

[0365] It means the position of bonding with chemical formula 4,

[0366] [Chemical formula D]

[0367]

[0368] In chemical formula D,

[0369] X3 is N or CR201, X4 is N or CR202, X5 is N or CR203, and at least two of X3 to X5 are N,

[0370] Any one of G1 to G3 and R201 to R203 is a moiety bonded to L7 of Chemical Formula 4, and the rest are the same as or different from each other and are each independently hydrogen; an aryl group which is unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; or a heteroaryl group,

[0371] [Chemical formula E]

[0372]

[0373] In chemical formula E,

[0374] Any one of G4 to G7 is a moiety bonded to L7 of Chemical Formula 4, and the rest are the same as or different from each other and are each independently hydrogen; an aryl group which is unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group; or a heteroaryl group.

[0375] The electron transport layer can play a role in promoting the transport of electrons. The electron transport material is suitably a material with high electron mobility that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto. The thickness of the electron transport layer may be from 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or greater, it has the advantage of preventing the electron transport characteristics from deteriorating, and when the thickness of the electron transport layer is 50 nm or less, it has the advantage of preventing the increase in driving voltage due to the electron transport layer being too thick in order to improve the movement of electrons. In particular, it is more preferred that the electron transport layer contains a compound represented by the following chemical formula 5, but the electron transport layer is not limited thereto.

[0376] [Chemical formula 5]

[0377] Ar8-(L8) p -Ar7-(L9) q -Ar9

[0378] In Chemical Formula 5,

[0379] L8 and L9 are the same as or different from each other and are each independently an unsubstituted or aryl-substituted arylene group,

[0380] Ar7 is a substituted or unsubstituted arylene group,

[0381] Ar8 and Ar9 are the same as or different from each other, and are each independently represented by the following chemical formula F,

[0382] p and q are each an integer of 1 to 3, and when p is 2 or more, L8 are the same as or different from each other, and when q is 2 or more, L9 are the same as or different from each other,

[0383] [Chemical formula F]

[0384]

[0385] In chemical formula F,

[0386] X6 is N or CR301, X7 is N or CR302, X8 is N or CR303, X9 is N or CR304, X10 is N or CR305, and at least two of X6 to X10 are N,

[0387] R301 to R305 are the same as or different from each other and are each independently hydrogen; deuterium; alkyl which is unsubstituted or substituted with deuterium; cycloalkyl which is unsubstituted or substituted with deuterium, cyano, alkyl, aryl or cycloalkyl; aryl which is unsubstituted or substituted with deuterium, cyano, alkyl, aryl or cycloalkyl; or heterocyclic group which is unsubstituted or substituted with deuterium, cyano, alkyl, aryl or cycloalkyl, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring which is unsubstituted or substituted with deuterium, cyano, alkyl, aryl or cycloalkyl, and

[0388] It means the position of bonding with Chemical Formula 4.

[0389] The electron injection layer can play a role in promoting the injection of electrons. The electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the cathode, and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0390] Examples of metal complex compounds include 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, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0391] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto.

[0392] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a dual emission type according to the materials used. DETAILED DESCRIPTION

[0394] Hereinafter, the present specification will be described in detail with reference to the embodiments for specifically describing the present specification. However, the embodiments according to the present specification can be modified in various forms and are not to be construed as limiting the scope of the present application to the embodiments described in detail below. The embodiments of the present application are provided to more completely illustrate the present specification to those of ordinary skill in the art.

[0395] <Synthesis example>

[0396] Synthesis Example 1-1. Synthesis of BH1-1

[0397]

[0398] <1-1-a> Synthesis of Compound BH 1-1-a

[0399] 9-Bromoanthracene-1,2,3,4,5,6,7,8,10-d9 (50 g, 188 mmol) and phenylboronic acid (25.2 g, 20.6 mmol) were dissolved in 1,4-dibromoanthracene. After being added to 150 ml of distilled water, Pd(PPh3)4 (10.9 g, 9.4 mmol) and K2CO3 (52.2 g, 376 mmol) were dissolved in 150 ml of distilled water and added thereto, and the resulting mixture was stirred under reflux for 24 hours. The reaction solution was cooled, the water layer was removed, and then 1,4-dihydropyridine was removed by distillation under reduced pressure. After the residue was dissolved in chloroform, the resulting solution was placed in a separatory funnel and washed three times with distilled water, and then the organic layer was dried over anhydrous magnesium sulfate. Thereafter, chloroform was removed under reduced pressure, and the residue was recrystallized with ethyl acetate (EA) to obtain compound BH1-1-a (45 g, yield 91%).

[0400] <1-1-b> Synthesis of Compound BH 1-1-b

[0401] After dispersing compound BH 1-1-a (45 g, 171 mmol) in 450 ml of chloroform, a solution of n-bromosuccinimide (30.4 g, 171 mmol) dissolved in 50 ml of dimethylformamide was slowly added dropwise thereto. Thereafter, after reacting at room temperature for 2 hours, 100 ml of a 20% Na2S2O3 aqueous solution was added dropwise thereto, and the organic layer was separated using a separatory funnel, and then the organic layer was washed three times with distilled water. Thereafter, residual moisture was removed over anhydrous magnesium sulfate, chloroform was removed by distillation under reduced pressure, and the residue was recrystallized in ethyl acetate (EA) to obtain compound BH 1-1-b (50 g, yield 86%).

[0402] <1-1-c> Synthesis of Compound BH 1-1

[0403] Compound BH1-1-b (50 g, 147 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran (62 g, 161 mmol) were dissolved in 1,4-dioxaborolan-2-yl. Pd(PPh3)4 (8.46 g, 7.3 mmol) and K2CO3 (40.5 g, 293 mmol) were dissolved in 150 ml of distilled water and added to 150 ml of alkane (500 ml), and the resulting mixture was refluxed for 24 hours. The reaction solution was cooled, and the resulting solid was filtered and then dissolved in chloroform, and then the resulting solution was placed in a separatory funnel and washed three times with distilled water. Thereafter, the organic layer was dried over anhydrous magnesium sulfate, chloroform was removed under reduced pressure, and the residue was recrystallized with ethyl acetate (EA) to obtain compound BH 1-1 (52 g, yield 68%). [M+H] = 519.2

[0404] Synthesis Example 1-2. Synthesis of BH 1-2

[0405]

[0406] <1-2-a> Synthesis of Compound BH 1-2-a

[0407] Compound BH1-2-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that naphthylboronic acid was used instead of phenylboronic acid.

[0408] <1-2-b> Synthesis of Compound BH 1-2-b

[0409] BH1-2-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-2-a was used instead of Compound BH1-1-a.

[0410] <1-2-c> Synthesis of Compound BH 1-2

[0411] BH1-2 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-2-b was used instead of compound BH1-1-b. [M+H]=569.2

[0412] Synthesis Example 1-3. Synthesis of Compound BH 1-3

[0413]

[0414] <1-3-a> Synthesis of Compound BH 1-3-a

[0415] Compound BH1-3-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and [1,1′-biphenyl]-4-ylboronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0416] <1-3-b> Synthesis of Compound BH 1-3-b

[0417] BH1-3-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-3-a was used instead of Compound BH1-1-a.

[0418] <1-3-c> Synthesis of Compound BH 1-3

[0419] BH1-3 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-3-b was used instead of compound BH1-1-b. [M+H]=587.2

[0420] Synthesis Example 1-4. Synthesis of Compound BH 1-4

[0421]

[0422] <1-4-a> Synthesis of Compound BH 1-4-a

[0423] Compound BH1-4-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene was used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9.

[0424] <1-4-b> Synthesis of Compound BH 1-4-b

[0425] BH1-4-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-4-a was used instead of Compound BH1-1-a.

[0426] <1-4-c> Synthesis of Compound BH 1-4

[0427] BH1-4 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-4-b and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran were used instead of compound BH1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0428] [M+H]=511.2

[0429] Synthesis Example 1-5. Synthesis of Compound BH 1-5

[0430]

[0431] BH1-5 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-2-b and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran were used instead of compound BH1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0432] [M+H]=569.2

[0433] Synthesis Example 1-6. Synthesis of Compound BH 1-6

[0434]

[0435] <1-6-a> Synthesis of Compound BH 1-6-a

[0436] Compound BH1-6-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and [1,1′-biphenyl]-2-ylboronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0437] <1-6-b> Synthesis of Compound BH 1-6-b

[0438] BH1-6-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-6-a was used instead of Compound BH1-1-a.

[0439] <1-6-c> Synthesis of Compound BH 1-6

[0440] BH1-6 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-6-b was used instead of compound BH1-1-b. [M+H]=587.2

[0441] Synthesis Example 1-7. Synthesis of Compound BH 1-7

[0442]

[0443] <1-7-a> Synthesis of Compound BH 1-7-a

[0444] Compound BH1-7-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and naphthalene-2-ylboronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0445] <1-7-b> Synthesis of Compound BH 1-7-b

[0446] BH1-7-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-7-a was used instead of Compound BH1-1-a.

[0447] <1-7-c> Synthesis of Compound BH 1-7-c

[0448] BH1-7-c was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that Compound BH1-7-b was used instead of Compound BH1-1-b.

[0449] <1-7-d> Synthesis of Compound BH 1-7

[0450] After 50 g of compound BH 1-7-c, 10 g of 5 wt% Pt / C, 300 ml of toluene and 700 ml of D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the temperature was raised to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a diatomaceous earth pad and then extracted. 38 g of BH 1-7 (yield 73%) was obtained by recrystallization with tetrahydrofuran / ethyl acetate (THF / EA). [M+H]=585.3

[0451] Synthesis Example 1-8. Synthesis of Compound BH 1-8

[0452]

[0453] <1-8-a> Synthesis of Compound BH 1-8-a

[0454] Compound BH1-8-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that naphthalene-2-ylboronic acid was used instead of phenylboronic acid.

[0455] <1-8-b> Synthesis of Compound BH 1-8-b

[0456] BH1-8-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-8-a was used instead of Compound BH1-1-a.

[0457] <1-8-c> Synthesis of Compound BH 1-8

[0458] BH1-8 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-8-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,5-b′]bisbenzofuran were used instead of compound BH1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0459] [M+H]=567.2

[0460] Synthesis Example 1-9. Synthesis of Compound BH 1-9

[0461]

[0462] <1-9-a> Synthesis of Compound BH 1-9-a

[0463] Compound BH1-9-a was obtained by synthesizing in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and dibenzo[b,c]furan-2-ylboronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0464] <1-9-b> Synthesis of Compound BH 1-9-b

[0465] BH1-9-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-9-a was used instead of Compound BH1-1-a.

[0466] <1-9-c> Synthesis of Compound BH 1-9

[0467] BH1-9 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-9-b and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[2,1-b:3,4-b′]bisbenzofuran were used instead of compound BH1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0468] [M+H]=601.2

[0469] Synthesis Example 1-10. Synthesis of Compound BH 1-10

[0470]

[0471] BH1-10 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-7-b and 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[2,1-b:3,4-b′]bisbenzofuran were used instead of compound BH1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0472] [M+H]=561.2

[0473] Synthesis Example 1-11. Synthesis of Compound BH 1-11

[0474]

[0475] <1-11-a> Synthesis of Compound BH 1-11-a

[0476] Compound BH1-11-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that [1,1′-biphenyl]-2-ylboronic acid was used instead of phenylboronic acid.

[0477] <1-11-b> Synthesis of Compound BH 1-11-b

[0478] BH1-11-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH1-11-a was used instead of Compound BH1-1-a.

[0479] <1-11-c> Synthesis of Compound BH 1-11

[0480] BH1-11 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-11-b was used instead of compound BH1-1-b. [M+H]=595.2

[0481] Synthesis Example 1-12. Synthesis of Compound BH 1-12

[0482]

[0483] BH1-12 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH1-2-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:3,4-b′]bisbenzofuran were used instead of compound BH1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0484] [M+H]=569.2

[0485] Synthesis Example 1-13. Synthesis of Compound BH 1-13

[0486]

[0487] BH1-13 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that compound BH1-1 was used instead of compound BH1-7-c. [M+H]=533.3

[0488] Synthesis Example 1-14. Synthesis of Compound BH 1-14

[0489]

[0490] Compound BH1-14 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH1-2 was used instead of Compound BH1-7-c. [M+H]=585.3

[0491] Synthesis Example 1-15. Synthesis of Compound BH 1-15

[0492]

[0493] Compound BH1-15 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH1-3 was used instead of Compound BH1-7-c. [M+H]=613.4

[0494] Synthesis Example 1-16. Synthesis of Compound BH 1-16

[0495]

[0496] Compound BH1-16 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH1-4 was used instead of Compound BH1-7-c. [M+H]=533.3

[0497] Synthesis Example 2-1. Synthesis of Compound BH 2-1

[0498]

[0499] <2-1-a> Synthesis of Compound BH 2-1-a

[0500] Compound BH1-1-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and (3-(naphthalen-1-yl)phenyl)boronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0501] <2-1-b> Synthesis of Compound BH 2-1-b

[0502] BH2-1-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH2-1-a was used instead of Compound BH1-1-a.

[0503] <2-1-c> Synthesis of Compound BH 2-1

[0504] BH 2-1 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 2-1-b and dibenzo[b,d]furan-1-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively. [M+H]=547.2

[0505] Synthesis Example 2-2. Synthesis of Compound BH 2-2

[0506]

[0507] BH 2-2 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-7-b and dibenzo[b,d]furan-2-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=471.2

[0508] Synthesis Example 2-3. Synthesis of Compound BH 2-3

[0509]

[0510] <2-3-a> Synthesis of Compound BH 2-3-a

[0511] Compound BH2-3-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and (4-(naphthalen-2-yl)phenyl)boronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0512] <2-3-b> Synthesis of Compound BH 2-3-b

[0513] BH2-3-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH2-3-a was used instead of Compound BH1-1-a.

[0514] <2-3-c> Synthesis of Compound BH 2-3

[0515] BH 2-3 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 2-3-b and dibenzo[b,d]furan-2-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively. [M+H]=547.2

[0516] Synthesis Example 2-4. Synthesis of Compound BH 2-4

[0517]

[0518] BH 2-4 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that dibenzo[b,d]furan-2-ylboronic acid was used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran. [M+H]=429.2

[0519] Synthesis Example 2-5. Synthesis of Compound BH 2-5

[0520]

[0521] BH 2-5 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-2-b and dibenzo[b,d]furan-2-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=479.2

[0522] Synthesis Example 2-6. Synthesis of Compound BH 2-6

[0523]

[0524] BH 2-6 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-4-b and (7-phenyldibenzo[b,d]furan-1-yl)boronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=497.2

[0525] Synthesis Example 2-7. Synthesis of Compound BH 2-7

[0526]

[0527] BH 2-7 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-4-b and 4,4,5,5-tetramethyl-2-(3-(naphthalen-1-yl)dibenzo[b,d]furan-1-yl-1,3,2-borolane were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=547.2

[0528] Synthesis Example 2-8. Synthesis of Compound BH 2-8

[0529]

[0530] <2-8-a> Synthesis of Compound BH 2-8-a

[0531] Compound BH2-8-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that (phenyl-d5)boronic acid was used instead of phenylboronic acid.

[0532] <2-8-b> Synthesis of Compound BH 2-8-b

[0533] BH2-8-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH2-8-a was used instead of Compound BH1-1-a.

[0534] <2-8-c> Synthesis of Compound BH 2-8

[0535] BH 2-8 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 2-8-b and (6-phenyldibenzo[b,d]furan-1-yl)boronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=510.3

[0536] Synthesis Example 2-9. Synthesis of Compound BH 2-9

[0537]

[0538] <2-9-a> Synthesis of Compound BH 2-3-a

[0539] Compound BH2-9-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-a, except that 9-bromoanthracene and naphthalene-1-ylboronic acid were used instead of 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 and phenylboronic acid, respectively.

[0540] <2-9-b> Synthesis of Compound BH 2-9-b

[0541] BH2-9-b was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-b, except that Compound BH2-9-a was used instead of Compound BH1-1-a.

[0542] <2-9-c> Synthesis of Compound BH 2-9

[0543] BH 2-9 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 2-9-b and (9-phenyldibenzo[b,d]furan-2-yl)boronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=547.2

[0544] Synthesis Example 2-10. Synthesis of Compound BH 2-10

[0545]

[0546] BH 2-10 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 2-9-b and naphtho[2,3-b]benzofuran-1-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=521.2

[0547] Synthesis Example 2-11. Synthesis of Compound BH 2-11

[0548]

[0549] BH 2-11 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-7-b and naphtho[1,2-b]benzofuran-7-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=521.2

[0550] Synthesis Example 2-12. Synthesis of Compound BH 2-12

[0551]

[0552] BH 2-12 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-6-b and naphtho[2,3-b]benzofuran-2-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran, respectively. [M+H]=547.2

[0553] Synthesis Example 2-13. Synthesis of Compound BH 2-13

[0554]

[0555] BH 2-13 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 2-3-b and naphtho[2,3-b]benzofuran-1-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively. [M+H]=597.2

[0556] Synthesis Example 2-14. Synthesis of Compound BH 2-14

[0557]

[0558] <2-14-a> Synthesis of Compound BH 2-14-a

[0559] BH 2-14-a was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that compound BH 1-6-b and naphtho[2,1-b]benzofuran-10-ylboronic acid were used instead of compound BH 1-1-b and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b′]bisbenzofuran, respectively.

[0560] <2-14-b> Synthesis of Compound BH 2-14

[0561] BH 2-14 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that compound BH 2-14-a was used instead of compound BH 1-7-c. [M+H]=572.4

[0562] Synthesis Example 2-15. Synthesis of Compound BH 2-15

[0563]

[0564] BH 2-15 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that naphtho[2,3-b]benzofuran-1-ylboronic acid was used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran. [M+H]=479.2

[0565] Synthesis Example 2-16. Synthesis of Compound BH 2-16

[0566]

[0567] BH 2-16 was obtained by performing synthesis in the same manner as in Synthesis Example 1-1-c, except that 4,4,5,5-tetramethyl-2-(3-phenyl-d5)naphtho[2,3,-b]benzofuran-1-yl)-1,3,2-dioxaborolane was used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzo[1,2-b:4,3-b']bisbenzofuran. [M+H]=560.3

[0568] Synthesis Example 2-17. Synthesis of Compound BH 2-17

[0569]

[0570] Compound BH2-17 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH2-1 was used instead of Compound BH1-7-c. [M+H]=573.4

[0571] Synthesis Example 2-18. Synthesis of Compound BH 2-18

[0572]

[0573] Compound BH2-18 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH2-2 was used instead of Compound BH1-7-c. [M+H]=493.3

[0574] Synthesis Example 2-19. Synthesis of Compound BH 2-19

[0575]

[0576] Compound BH2-19 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH2-3 was used instead of Compound BH1-7-c. [M+H]=573.4

[0577] Synthesis Example 2-20. Synthesis of Compound BH 2-20

[0578]

[0579] Compound BH2-20 was obtained by performing synthesis in the same manner as in Synthesis Example 1-7-d, except that Compound BH2-5 was used instead of Compound BH1-7-c. [M+H]=493.3

[0580] <Experimental example>

[0581]

[0582]

[0583]

[0584]

[0585] <Experimental Example 1>

[0586] The evaporation temperatures of BH 1-1 to BH 1-16 and BH 2-1 to BH 2-20 prepared in the preparation examples were measured and are shown in Table 1 below. The evaporation temperature was measured by thermogravimetric analysis (TGA). The temperature at which 1% weight loss of the sample occurred was referred to as Td-1%, and deposition was performed at a temperature of 60°C to 80°C below this temperature. The pressure at this time was 10 -4 Support up to 10 -6 The evaporation temperature may have mobility within a range that can be understood by those skilled in the art, and may include a variation range of ±10°C.

[0587] [Table 1]

[0588]

[0589]

[0590] <Experimental Example 2>

[0591] Example 1

[0592] A layer having a thickness of 1000 nm is deposited thereon as an anode. The substrate of indium tin oxide (ITO) / Ag / ITO was cut into a size of 50mm×50mm×0.5mm, placed in distilled water dissolved with a dispersant and ultrasonically cleaned. A product manufactured by Fischer Co., was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co., was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone and methanol in this order, and then dried.

[0593] HAT-CN was thermally vacuum deposited on the anode to a thickness of Thus, a hole injection layer is formed, and HTL1 as a hole transporting material is vacuum deposited on the hole injection layer to a thickness of Then, HTL2 is used to form an electron blocking layer. Subsequently, BD-1 as a dopant (2 mass % of the total weight of the light-emitting layer) and compounds BH1-1 and BH2-1 as hosts (weight ratio 50:50) were deposited by co-deposition to form a light-emitting layer with a thickness of 20 nm. Then, ETL2 was deposited to a thickness of Thus, a hole blocking layer is formed, and the compound ETL1 and lithium quinoline (Liq) are mixed at a ratio of 7:3 to form a layer having a thickness of Subsequently, magnesium and lithium fluoride (LiF) were used to A film with a thickness of 1000 Å is formed as an electron injection layer.

[0594] A cathode was formed using magnesium and silver (1:4) to a thickness of Afterwards, CP1 is deposited to a thickness of In the above steps, the deposition rate of the organic material is maintained at

[0595]

[0596] Examples 2 to 64

[0597] The device was manufactured in the same manner as in Example 1, except that in Example 1, the compounds specified in Table 2 below were used as materials for the light-emitting layer, and the method for forming the light-emitting layer (co-deposition or pre-mixing), the mixing ratio, the light-emitting dopant, and the hole blocking layer were changed. In Example 1, the light-emitting layer was formed (co-deposited) using the compound of Chemical Formula 1 and the compound of Chemical Formula 2 by different deposition sources, and in the Examples and Comparative Examples in Table 1 below in which the pre-mixed deposition method was used, the materials (hosts) were pre-mixed before forming the light-emitting layer, and the light-emitting layer was formed by one deposition source.

[0598] Comparative Examples 1 to 13

[0599] A device was manufactured in the same manner as in Example 1, except that in Example 1, the compounds specified in Table 2 below were used as materials for the light-emitting layer, and the method of forming the light-emitting layer (co-deposition or premixing) was changed.

[0600]

[0601] In the devices fabricated in Examples 1 to 64 and Comparative Examples 1 to 13, at 20 mA / cm 2 The driving voltage, efficiency and time to reach a value of 97% compared to the initial luminance (T97) were measured at a current density of 1.3 Å and the results are shown in Table 1 below.

[0602] [Table 2]

[0603]

[0604]

[0605]

[0606]

[0607]

[0608]

[0609]

[0610] Embodiments 1 to 64 of the present application include both the compound of Chemical Formula 1 and the compound of Chemical Formula 2 as the host of the light-emitting layer. In Comparative Examples 1 and 2, the compound of Chemical Formula 1 and the host in which anthracene is bonded to the 3rd or 4th position of dibenzofuran are used as the light-emitting host, and it can be determined that the driving voltage, efficiency and service life of the device are lower than those in the embodiment of the present application. In Comparative Examples 3 and 4, the compound of Chemical Formula 1 and the host in which anthracene is bonded to the 3rd or 4th position of naphthobenzofuran are used as the light-emitting host, and it can be determined that the driving voltage, efficiency and service life of the device are lower than those in the embodiment of the present application. In Comparative Examples 5 and 6, two compounds of Chemical Formula 2 are used as the light-emitting host, and it can be determined that the driving voltage, efficiency and service life of the device are lower than those in the embodiment of the present application. In Comparative Examples 7 and 8, one of the compound of Chemical Formula 1 or the compound of Chemical Formula 2 and an aryl-based host are used as the light-emitting host, and it can be determined that the driving voltage, efficiency and service life of the device are lower than those in the embodiment of the present application. In Comparative Examples 7 and 8, two aromatic-based hosts are used as light-emitting hosts, and it can be determined that the driving voltage, efficiency, and service life of the device are lower than those in the embodiment of the present application. In Comparative Examples 10 to 13, the compound of Chemical Formula 1 or 2 is used alone, and it can be determined that the driving voltage, efficiency, and service life of the device are lower than those in the embodiment of the present application.

[0611] In addition, it can be determined that when the same compound is premixed and then deposited (one deposition source) as in Examples 7 and 8, 12 and 13, 23 and 24, 28 and 29, 34 and 35, 48 and 50, 53 and 58, 61 and 62, the driving voltage, efficiency and service life of the device are also slightly increased compared to the case of using co-deposition (separate deposition source). This is because the interaction between the two compounds occurs smoothly, thereby improving processability.

Claims

1. An organic light-emitting device, comprising: anode; cathode; and A first organic material layer disposed between the anode and the cathode, The first organic material layer includes a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2: [Chemical formula 1] In Chemical Formula 1, X1 is O or S, Cy1 is a substituted or unsubstituted dibenzofuran; or a substituted or unsubstituted dibenzothiophene, L1 is a direct bond; or a substituted or unsubstituted arylene group, Ar1 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, n1 is an integer of 0 to 8, and when n1 is 2 or more, two or more R1 are the same as or different from each other, n2 is an integer from 0 to 4, and when n2 is 2 or more, two or more R2 are the same as or different from each other, [Chemical formula 2] In chemical formula 2, L2 is a direct bond; or a substituted or unsubstituted arylene group, Ar2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, Z1 is hydrogen; deuterium; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, m1 is an integer of 0 to 8, and when m1 is 2 or more, two or more Z1 are the same as or different from each other, and Ar3 is the following chemical formula A, and Z10 or Z11 of the following chemical formula A is connected to L2 of chemical formula 2, [Chemical formula A] In chemical formula A, X2 is O or S, Cy2 is substituted or unsubstituted benzene; or substituted or unsubstituted naphthalene, and The group not connected to L2 in Chemical Formula 2 among Z10 and Z11, Z12 and Z13 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

2. The organic light-emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] In Chemical Formulas 1-1 to 1-6, The definitions of X1, R1, R2, n1, n2, L1 and Ar1 are the same as those in Chemical Formula 1, X1' is O or S, R3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other.

3. The organic light-emitting device according to claim 1, wherein Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2: [Chemical formula 2-1] [Chemical formula 2-2] In chemical formulas 2-1 and 2-2, Definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and definitions of X2, Z10 to Z13 and Cy2 are the same as those in Chemical Formula A.

4. The organic light-emitting device according to claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1-1 to 2-1-4: [Chemical formula 2-1-1] [Chemical formula 2-1-2] [Chemical formula 2-1-3] [Chemical formula 2-1-4] In chemical formulas 2-1-1 to 2-1-4, The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2 and Z11 to Z13 are the same as those in Chemical Formula A, Z2 and Z3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, m2 is an integer from 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other, and m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other.

5. The organic light-emitting device according to claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-2-1 to 2-2-4: [Chemical formula 2-2-1] [Chemical formula 2-2-2] [Chemical formula 2-2-3] [Chemical formula 2-2-4] In chemical formulas 2-2-1 to 2-2-4, The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2, Z10, Z12 and Z13 are the same as those in Chemical Formula A, Z2 and Z3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, m2 is an integer from 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other, and m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other. 6 . The organic light emitting device according to claim 1 , wherein the chemical formula Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. 7 . The organic light emitting device according to claim 1 , wherein the chemical formula Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

8. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1, and Chemical Formula 2 is represented by the following Chemical Formula 2-1-2: [Chemical formula 1-1] [Chemical formula 2-1-2] In Chemical Formula 1-1 and Chemical Formula 2-1-2, The definitions of X1, R1, R2, n1, n2, L1 and Ar1 are the same as those in Chemical Formula 1, X1' is O or S, R3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other, The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2 and Z11 to Z13 are the same as those in Chemical Formula A, Z2 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and m2 is an integer of 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other.

9. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1, and Chemical Formula 2 is represented by the following Chemical Formula 2-1-3: [Chemical formula 1-1] [Chemical formula 2-1-3] In Chemical Formula 1-1 and Chemical Formula 2-1-3, The definitions of X1, R1, R2, n1, n2, L1 and Ar1 are the same as those in Chemical Formula 1, X1' is O or S, R3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other, The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2 and Z11 to Z13 are the same as those in Chemical Formula A, Z2 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and m2 is an integer of 0 to 6, and when m2 is 2 or more, two or more Z2 are the same as or different from each other.

10. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1, and Chemical Formula 2 is represented by the following Chemical Formula 2-1-4: [Chemical formula 1-1] [Chemical formula 2-1-4] In Chemical Formula 1-1 and Chemical Formula 2-1-4, The definitions of X1, R1, R2, n1, n2, L1 and Ar1 are the same as those in Chemical Formula 1, X1' is O or S, R3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other, The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2 and Z11 to Z13 are the same as those in Chemical Formula A, Z3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other.

11. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1, and Chemical Formula 2 is represented by the following Chemical Formula 2-2-4: [Chemical formula 1-1] [Chemical formula 2-2-4] In Chemical Formula 1-1 and Chemical Formula 2-2-4, The definitions of X1, R1, R2, n1, n2, L1 and Ar1 are the same as those in Chemical Formula 1, X1' is O or S, R3 is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, n3 is an integer of 0 to 6, and when n3 is 2 or more, two or more R3 are the same as or different from each other, The definitions of Z1, m1, L2 and Ar2 are the same as those in Chemical Formula 2, and the definitions of X2, Z10, Z12 and Z13 are the same as those in Chemical Formula A, Z3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and m3 is an integer of 0 to 4, and when m3 is 2 or more, two or more Z3 are the same as or different from each other.

12. The organic light emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

13. The organic light emitting device according to claim 1, wherein Chemical Formula 2 is represented by any one of the following compounds: 14 . The organic light emitting device according to claim 1 , wherein the first organic material layer is a hole transport layer, a hole injection layer, a hole transport and injection layer, or an electron blocking layer. The organic light-emitting device according to claim 1 , wherein the first organic material layer is a light-emitting layer. The organic light emitting device according to claim 15 , wherein the light emitting layer further comprises a dopant. 17 . The organic light emitting device according to claim 1 , wherein the first organic material layer is an electron transport layer, an electron injection layer, an electron transport and injection layer, or a hole blocking layer.

18. An organic light-emitting device according to claim 1, wherein an organic material layer having one or more layers is also arranged between the anode and the cathode, and the organic material layer further includes one or more layers of the following: a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

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