Organic compound and organic light-emitting device including same

Abstract

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

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0136829 filed with the Korean Patent Office on October 13, 2023, the entire contents of which are incorporated herein by reference.

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

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

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

[0005] Prior art literature

[0006] Patent Literature

[0007] (Patent Document 1) Korean Patent Publication No. 10-2023-025537 Summary of the invention

[0008] Technical issues

[0009] The present specification provides an organic compound and an organic light-emitting device including the same.

[0010] Solution to the problem

[0011] One embodiment of the present specification provides an organic compound represented by the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R1 to R8 are the same or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group,

[0016] R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,

[0017] Ar1 is any one of the following heterocyclic groups: i) a substituted or unsubstituted five-membered or six-membered monocyclic heterocyclic group containing at least one of N, O and S as a heteroelement; ii) a heterocyclic group formed by condensing two substituted or unsubstituted five-membered or six-membered rings containing at least one of N and S as a heteroelement; iii) a heterocyclic group formed by condensing three or more substituted or unsubstituted rings containing at least one of O and S as a heteroelement; and iv) a heterocyclic group formed by condensing three or more substituted or unsubstituted six-membered rings containing N as a heteroelement,

[0018] Ar2 is a substituted or unsubstituted aryl group,

[0019] m is an integer from 1 to 3,

[0020] n is an integer from 1 to 3,

[0021] When m and n are 2 or more, two or more R9 and R10 are the same as or different from each other.

[0022] In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers contains the organic compound.

[0023] Effects of the Invention

[0024] The organic compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The organic compound according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 An example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10 are stacked in this order is shown.

[0026] Figure 2 The diagram shows an example of an organic light-emitting device having a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a hole regulation layer 5, a light-emitting layer 6, an electron regulation layer 7, an electron transport layer 8, an electron injection layer 9, a cathode 10 and a covering layer 11 stacked in sequence.

[0027] Explanation of symbols

[0028] 1: Substrate

[0029] 2: Anode

[0030] 3: Hole injection layer

[0031] 4: Hole transport layer

[0032] 5: Hole regulation layer

[0033] 6: Luminous layer

[0034] 7: Electronic adjustment layer

[0035] 8: Electron transport layer

[0036] 9: Electron injection layer

[0037] 10: Cathode

[0038] 11: Overlay DETAILED DESCRIPTION

[0039] Next, this specification is described in more detail.

[0040] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0041] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0042] In the present specification, "*" indicates a position bonded to a chemical formula or a compound.

[0043] In the present specification, examples of substituents are described below, but are not limited thereto.

[0044] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0045] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group (-CN), an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0046] Examples of the above substituents are described below, but are not limited thereto.

[0047] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0048] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another 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.

[0049] The substituents containing an alkyl moiety described in the present specification include all of linear and branched forms.

[0050] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0051] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0052] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in 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.

[0053] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0054] In the present specification, the description of the above-mentioned aryl group is applicable to the above-mentioned arylene group except that the above-mentioned arylene group is divalent.

[0055] In the present specification, the above-mentioned heteroarylene group is applicable to the above-mentioned description of the heteroaryl group except that the above-mentioned heteroarylene group is divalent.

[0056] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0057] For example, when the adjacent groups are combined to form a ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof may be formed. The above hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The above heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si and Se. In this specification, the above aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.

[0058] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0059] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.

[0060] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctane etc., but not limited thereto.

[0061] In the present specification, an aromatic heterocycle refers to 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, pyridazine, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but are not limited to these.

[0062] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0063] Next, the organic compound of the above Chemical Formula 1 will be described in detail.

[0064] [Chemical formula 1]

[0065]

[0066] In the above chemical formula 1,

[0067] R1 to R8 are the same or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group,

[0068] R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,

[0069] Ar1 is any one of the following heterocyclic groups: i) a substituted or unsubstituted five-membered or six-membered monocyclic heterocyclic group containing at least one of N, O and S as a heteroelement; ii) a heterocyclic group formed by condensing two substituted or unsubstituted five-membered or six-membered rings containing at least one of N and S as a heteroelement; iii) a heterocyclic group formed by condensing three or more substituted or unsubstituted rings containing at least one of O and S as a heteroelement; and iv) a heterocyclic group formed by condensing three or more substituted or unsubstituted six-membered rings containing N as a heteroelement,

[0070] Ar2 is a substituted or unsubstituted aryl group,

[0071] m is an integer from 1 to 3,

[0072] n is an integer from 1 to 3,

[0073] When m and n are 2 or more, two or more R9 and R10 are the same as or different from each other.

[0074] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0075] In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0076] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0077] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0078] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted fluorenyl.

[0079] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0080] In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted or unsubstituted with deuterium.

[0081] In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted or unsubstituted with deuterium.

[0082] In one embodiment of the present specification, the above-mentioned R1 to R8 are the same as or different from each other, and are each independently deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthrenyl substituted or unsubstituted by deuterium, or fluorenyl substituted or unsubstituted by deuterium.

[0083] In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently deuterium, a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, or a naphthyl group substituted or unsubstituted by deuterium.

[0084] In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently deuterium or an aryl group having 6 to 20 carbon atoms.

[0085] In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently deuterium or an aryl group having 6 to 12 carbon atoms.

[0086] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl or fluorenyl.

[0087] In one embodiment of the present specification, the above R1 to R8 are the same as or different from each other, and are each independently deuterium, phenyl, biphenyl or naphthyl.

[0088] In one embodiment of the present specification, all of R1 to R8 are deuterium.

[0089] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0090] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0091] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0092] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0093] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 20 carbon atoms which may be substituted or unsubstituted by deuterium.

[0094] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which may be substituted or unsubstituted by deuterium, or an aryl group having 6 to 12 carbon atoms which may be substituted or unsubstituted by deuterium.

[0095] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are independently hydrogen, deuterium, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, or naphthyl substituted or unsubstituted by deuterium.

[0096] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0097] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0098] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl or naphthyl.

[0099] In one embodiment of the present specification, R9 and R10 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0100] In one embodiment of the present specification, the above R9 are all hydrogen.

[0101] In one embodiment of the present specification, the above R9 are all deuterium.

[0102] In one embodiment of the present specification, all of the above R10 are hydrogen.

[0103] In one embodiment of the present specification, the above R10 are all deuterium.

[0104] In one embodiment of the present specification, Ar1 is any one of the following heterocyclic groups: i) a substituted or unsubstituted five-membered or six-membered monocyclic heterocyclic group containing at least one of N, O and S as a heteroelement; ii) a heterocyclic group formed by condensing two substituted or unsubstituted five-membered or six-membered rings containing at least one of N and S as a heteroelement; and iii) a heterocyclic group formed by condensing three or more substituted or unsubstituted rings containing at least one of O and S as a heteroelement.

[0105] In one embodiment of the present specification, Ar1 is any one of the following heterocyclic groups: i) a five-membered or six-membered monocyclic heterocyclic group containing at least one of N, O and S as a heteroelement and being substituted or unsubstituted with deuterium; ii) a heterocyclic group formed by condensing two five-membered or six-membered rings containing at least one of N and S as a heteroelement and being substituted or unsubstituted with deuterium; and iii) a heterocyclic group formed by condensing three or more rings containing at least one of O and S as a heteroelement and being substituted or unsubstituted with deuterium.

[0106] In one embodiment of the present specification, the Ar1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0107] [Chemical formula 1-1]

[0108]

[0109] [Chemical formula 1-2]

[0110]

[0111] [Chemical formula 1-3]

[0112]

[0113] [Chemical formula 1-4]

[0114]

[0115] In the above chemical formulas 1-1 to 1-4,

[0116] X1, X3 and X4 are O or S,

[0117] X2 is N or CR,

[0118] p and q are each an integer from 0 to 2,

[0119] When p is 0, X2 is N,

[0120] R, G1 to G4 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 heterocyclic group,

[0121] g1 is 1 to 3,

[0122] g2 is 1 to 8,

[0123] g3 is 1 to 11,

[0124] g4 is 1 to 9,

[0125] When g1 to g4 are 2 or more, the two or more G1 to G4 are the same as or different from each other.

[0126] * is a site connected to dibenzofuran of the above Chemical Formula 1.

[0127] In one embodiment of the present specification, the above X1 is O or S

[0128] In one embodiment of the present specification, the above-mentioned X1 is O.

[0129] In one embodiment of the present specification, the above-mentioned X1 is S.

[0130] In one embodiment of the present specification, the above-mentioned X2 is N or CR.

[0131] In one embodiment of the present specification, the above-mentioned X2 is N.

[0132] In one embodiment of the present specification, the above-mentioned X2 is CR.

[0133] In one embodiment of the present specification, the above p is an integer of 0 or 1.

[0134] In one embodiment of the present specification, the above-mentioned p is 2.

[0135] In one embodiment of the present specification, the above-mentioned p is 1.

[0136] In one embodiment of the present specification, the above-mentioned p is 0.

[0137] In one embodiment of the present specification, when the above p is 0, X2 is N. In one embodiment of the present specification, the above X3 is O or S.

[0138] In one embodiment of the present specification, the above-mentioned X3 is O.

[0139] In one embodiment of the present specification, the above-mentioned X3 is S.

[0140] In one embodiment of the present specification, the above-mentioned X4 is O or S.

[0141] In one embodiment of the present specification, the above-mentioned X4 is O.

[0142] In one embodiment of the present specification, the above-mentioned X4 is S.

[0143] In one embodiment of the present specification, the above q is an integer of 0 or 1.

[0144] In one embodiment of the present specification, the above q is 2.

[0145] In one embodiment of the present specification, the above q is 1.

[0146] In one embodiment of the present specification, the above q is 0.

[0147] In one embodiment of the present specification, R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a portion connected to dibenzofuran of Chemical Formula 1.

[0148] In one embodiment of the present specification, R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a portion connected to dibenzofuran of Chemical Formula 1.

[0149] In one embodiment of the present specification, the R is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a portion connected to the dibenzofuran of the above Chemical Formula 1.

[0150] In one embodiment of the present specification, R is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or a portion connected to dibenzofuran of Chemical Formula 1.

[0151] In one embodiment of the present specification, the R is hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a portion connected to the dibenzofuran of the above Chemical Formula 1.

[0152] In one embodiment of the present specification, R is hydrogen, deuterium, an aryl group having 6 to 12 carbon atoms which is substituted or unsubstituted with deuterium, or a portion connected to dibenzofuran of the above Chemical Formula 1.

[0153] In one embodiment of the present specification, R is hydrogen, deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, or a portion connected to dibenzofuran of Chemical Formula 1.

[0154] In one embodiment of the present specification, the R is hydrogen, deuterium, a phenyl group which may be substituted with deuterium, or a portion connected to the dibenzofuran of the above Chemical Formula 1.

[0155] In one embodiment of the present specification, the R is hydrogen, deuterium, phenyl, biphenyl, naphthyl, or a portion connected to dibenzofuran of the above Chemical Formula 1.

[0156] In one embodiment of the present specification, the R is hydrogen, deuterium, phenyl, or a portion connected to dibenzofuran of the chemical formula 1.

[0157] In one embodiment of the present specification, the above-mentioned G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0158] In one embodiment of the present specification, the above-mentioned G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0159] In one embodiment of the present specification, the above-mentioned G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0160] In one embodiment of the present specification, the above-mentioned G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0161] In one embodiment of the present specification, the above G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted butyl, substituted or unsubstituted cyclopentyl, or substituted or unsubstituted phenyl.

[0162] In one embodiment of the present specification, the above-mentioned G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms which is substituted or not substituted by deuterium, a cycloalkyl group having 3 to 10 carbon atoms which is substituted or not substituted by deuterium, an aryl group having 6 to 12 carbon atoms which is substituted or not substituted by deuterium, or a heteroaryl group having 2 to 20 carbon atoms which is substituted or not substituted by deuterium.

[0163] In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, cyclopropyl substituted or unsubstituted by deuterium, cyclobutyl substituted or unsubstituted by deuterium, cyclopentyl substituted or unsubstituted by deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, or naphthyl substituted or unsubstituted by deuterium.

[0164] In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, butyl group substituted or unsubstituted by deuterium, cyclopentyl group substituted or unsubstituted by deuterium, or phenyl group substituted or unsubstituted by deuterium.

[0165] In one embodiment of the present specification, the above G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

[0166] In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, phenyl, biphenyl or naphthyl.

[0167] In one embodiment of the present specification, the above G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, butyl, cyclopentyl or phenyl.

[0168] In one embodiment of the present specification, the above G1 to G4 are the same as or different from each other, and are each independently hydrogen, deuterium, tert-butyl, cyclopentyl or phenyl.

[0169] In one embodiment of the present specification, the above-mentioned G1 is hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0170] In one embodiment of the present specification, the above-mentioned G1 is hydrogen, deuterium, or a phenyl group which may be substituted with deuterium.

[0171] In one embodiment of the present specification, the above-mentioned G1 is hydrogen, deuterium or phenyl.

[0172] In one embodiment of the present specification, G2 is hydrogen, deuterium, substituted or unsubstituted butyl, substituted or unsubstituted cyclopentyl, or substituted or unsubstituted phenyl.

[0173] In one embodiment of the present specification, G2 is hydrogen, deuterium, butyl group which may be substituted by deuterium, cyclopentyl group which may be substituted by deuterium, or phenyl group which may be substituted by deuterium.

[0174] In one embodiment of the present specification, G2 is hydrogen, deuterium, tert-butyl group which may be substituted by deuterium, cyclopentyl group which may be substituted by deuterium, or phenyl group which may be substituted by deuterium.

[0175] In one embodiment of the present specification, the above-mentioned G2 is hydrogen, deuterium, butyl, cyclopentyl or phenyl.

[0176] In one embodiment of the present specification, the above-mentioned G2 is hydrogen, deuterium, tert-butyl, cyclopentyl or phenyl.

[0177] In one embodiment of the present specification, the above-mentioned G2 is hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0178] In one embodiment of the present specification, the above-mentioned G2 is hydrogen, deuterium, or a phenyl group which may be substituted with deuterium.

[0179] In one embodiment of the present specification, the above-mentioned G2 is hydrogen, deuterium or phenyl.

[0180] In one embodiment of the present specification, the above-mentioned G3 is hydrogen or deuterium.

[0181] In one embodiment of the present specification, the above-mentioned G4 is hydrogen or deuterium.

[0182] In one embodiment of the present specification, the g1 is 1 to 2.

[0183] In one embodiment of the present specification, the above g1 is 3.

[0184] In one embodiment of the present specification, the above g1 is 2.

[0185] In one embodiment of the present specification, the above g1 is 1.

[0186] In one embodiment of the present specification, the above g2 is 1 to 7.

[0187] In one embodiment of the present specification, the above g2 is 8.

[0188] In one embodiment of the present specification, the above g2 is 7.

[0189] In one embodiment of the present specification, the above g2 is 6.

[0190] In one embodiment of the present specification, the above g2 is 5.

[0191] In one embodiment of the present specification, the above g2 is 4.

[0192] In one embodiment of the present specification, the above g2 is 3.

[0193] In one embodiment of the present specification, the above g2 is 2.

[0194] In one embodiment of the present specification, the above g2 is 1.

[0195] In one embodiment of the present specification, the g3 is 1 to 10.

[0196] In one embodiment of the present specification, the above g3 is 11.

[0197] In one embodiment of the present specification, the above g3 is 10.

[0198] In one embodiment of the present specification, the above g3 is 9.

[0199] In one embodiment of the present specification, the above g3 is 8.

[0200] In one embodiment of the present specification, the above g3 is 7.

[0201] In one embodiment of the present specification, the above g3 is 6.

[0202] In one embodiment of the present specification, the above g3 is 5.

[0203] In one embodiment of the present specification, the above g3 is 4.

[0204] In one embodiment of the present specification, the above g3 is 3.

[0205] In one embodiment of the present specification, the above g3 is 2.

[0206] In one embodiment of the present specification, the above g3 is 1.

[0207] In one embodiment of the present specification, the above g4 is 1 to 8.

[0208] In one embodiment of the present specification, the above g4 is 9.

[0209] In one embodiment of the present specification, the above g4 is 8.

[0210] In one embodiment of the present specification, the above g4 is 7.

[0211] In one embodiment of the present specification, the above g4 is 6.

[0212] In one embodiment of the present specification, the above g4 is 5.

[0213] In one embodiment of the present specification, the above g4 is 4.

[0214] In one embodiment of the present specification, the above g4 is 3.

[0215] In one embodiment of the present specification, the above g4 is 2.

[0216] In one embodiment of the present specification, the above g4 is 1.

[0217] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0218] In one embodiment of the present specification, the Ar2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0219] In one embodiment of the present specification, the Ar2 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0220] In one embodiment of the present specification, the above-mentioned Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, or a substituted or unsubstituted triphenylene group.

[0221] In one embodiment of the present specification, Ar2 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 phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

[0222] In one embodiment of the present specification, Ar2 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, or a substituted or unsubstituted phenanthryl group.

[0223] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0224] In one embodiment of the present specification, the above-mentioned Ar2 is phenyl substituted or unsubstituted by hydrogen, deuterium, phenyl or naphthyl; biphenyl substituted or unsubstituted by hydrogen, deuterium, phenyl or naphthyl; terphenyl substituted or unsubstituted by hydrogen, deuterium, phenyl or naphthyl; naphthyl substituted or unsubstituted by hydrogen, deuterium, phenyl or naphthyl; or phenanthrenyl substituted or unsubstituted by hydrogen, deuterium, phenyl or naphthyl.

[0225] In one embodiment of the present specification, Ar2 is a phenyl group which may be substituted by hydrogen, deuterium, phenyl or naphthyl; a biphenyl group which may be substituted by hydrogen, deuterium or phenyl; or a naphthyl group which may be substituted by hydrogen, deuterium or phenyl.

[0226] In one embodiment of the present specification, Ar2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group or a phenanthryl group.

[0227] In one embodiment of the present specification, the Ar2 is a phenyl group, a biphenyl group or a naphthyl group.

[0228] In one embodiment of the present specification, the above m is an integer of 1 or 2.

[0229] In one embodiment of the present specification, the above m is 3.

[0230] In one embodiment of the present specification, the above m is 2.

[0231] In one embodiment of the present specification, the above m is 1.

[0232] In one embodiment of the present specification, the above n is an integer of 1 or 2.

[0233] In one embodiment of the present specification, the above n is 3.

[0234] In one embodiment of the present specification, the above n is 2.

[0235] In one embodiment of the present specification, the above n is 1.

[0236] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-4.

[0237] [Chemical formula 2-1]

[0238]

[0239] [Chemical formula 2-2]

[0240]

[0241] [Chemical formula 2-3]

[0242]

[0243] [Chemical formula 2-4]

[0244]

[0245] In the above Chemical Formula 2-1 to Chemical Formula 2-4,

[0246] The definitions of the above R1 to R10, Ar1, Ar2, m and n are the same as those in the above Chemical Formula 1.

[0247] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-9.

[0248]

[0249]

[0250] In the above chemical formulas 3-1 to 3-9,

[0251] R', R", and R'" are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

[0252] x, y and z are integers from 1 to 5,

[0253] R1 to R10, Ar1, m and n are the same as defined in the above Chemical Formula 1.

[0254] In one embodiment of the present specification, R', R", and R'" are the same as or different from each other, and are independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0255] In one embodiment of the present specification, R', R", and R'" are the same as or different from each other, and are independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0256] In one embodiment of the present specification, R', R", and R'" are the same as or different from each other, and are independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms which may be substituted with deuterium or not.

[0257] In one embodiment of the present specification, the above R', R", and R'" are the same as or different from each other, and are each independently hydrogen or deuterium.

[0258] In one embodiment of the present specification, the above R's are all hydrogen.

[0259] In one embodiment of the present specification, the above R's are all deuterium.

[0260] In one embodiment of the present specification, the above R" are all hydrogen.

[0261] In one embodiment of the present specification, the above R" is deuterium.

[0262] In one embodiment of the present specification, the above R''' are all hydrogen.

[0263] In one embodiment of the present specification, the above R'' is deuterium.

[0264] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following compounds.

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273] The compound represented by Chemical Formula 1 according to one embodiment of the present specification can manufacture a core structure as described in the manufacturing example below. The substituents can be combined by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art. Specifically, using starting materials, intermediate materials, etc. known in the art, a compound corresponding to the scope of the above Chemical Formula 1 can be synthesized by a synthesis method known in the art.

[0274] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above Chemical Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be adjusted by introducing various substituents into the core structure of the structure as described above.

[0275] In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.

[0276] The organic light-emitting device according to the present specification is characterized by comprising: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the organic compound represented by the above Chemical Formula 1.

[0277] The organic light-emitting device of the present specification uses the organic compound of the above Chemical Formula 1 to form an organic layer, and can be manufactured using a common manufacturing method and materials for an organic light-emitting device.

[0278] The organic compound can be formed into an organic layer by not only vacuum evaporation but also solution coating when manufacturing an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited to these.

[0279] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and one or more of the electron transport and injection layers as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic layers.

[0280] In one embodiment of the present specification, the thickness of the organic layer including the organic compound of the above Chemical Formula 1 may be to to Preferably to

[0281] In another embodiment, the organic layer may include other organic compounds, metals or metal compounds in addition to the organic compound represented by the above Chemical Formula 1.

[0282] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the organic compound represented by the above Chemical Formula 1.

[0283] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer, a red light-emitting layer or a green light-emitting layer.

[0284] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer.

[0285] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the organic compound represented by the above Chemical Formula 1 as a main component.

[0286] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the organic compound represented by the above Chemical Formula 1 as a main body, and may further include a dopant. Specifically, the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0287] In one embodiment of the present specification, the light-emitting layer may include a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the light-emitting layer may include a weight ratio of 99:1 to 50:50, a weight ratio of 99:1 to 70:30, a weight ratio of 99:1 to 80:20, a weight ratio of 99:1 to 90:10, or a weight ratio of 99:1 to 95:5.

[0288] In one embodiment of the present specification, the dopant may include an arylamine compound, a heterocyclic compound including boron and nitrogen, a metal coordination compound, a platinum coordination compound, an iridium coordination compound, or the like.

[0289] For example, when the light-emitting layer emits red light, as the light-emitting dopant, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or Alq 3 (tris(8-hydroxyquinolino)aluminum, tris(8-hydroxyquinolino)aluminum) and other fluorescent substances, but not limited to these. When the light-emitting layer emits green light, Ir(ppy) can be used as a light-emitting dopant. 3 Phosphorescent materials such as (fac tris(2-phenylpyridine)iridium, face tris(2-phenylpyridine)iridium) or Alq 3 (tris(8-hydroxyquinoline)aluminum) and other fluorescent substances, but not limited to these. When the light-emitting layer emits blue light, platinum coordination compounds, (4,6-F 2 ppy) 2 Phosphorescent materials such as Irpic; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO series polymers, PPV series polymers, but are not limited to these.

[0290] In one embodiment of the present specification, the dopant is a metal complex.

[0291] In one embodiment of the present specification, the dopant is a platinum coordination compound.

[0292] In one embodiment of the present specification, the dopant is an iridium complex.

[0293] In one embodiment of the present specification, the dopant may include a compound represented by the following chemical formula D-1 or D-2, but is not limited thereto.

[0294] [Chemical formula D-1]

[0295]

[0296] [Chemical formula D-2]

[0297]

[0298] In the above chemical formula D-1,

[0299] Y1 and Y2 are the same as or different from each other, and are each independently CR111 or NR112, at least one of Y1 and Y2 is NR112,

[0300] Z1 and Z2 are the same as or different from each other, and are each independently a substituted or unsubstituted five-membered ring, a substituted or unsubstituted six-membered ring, or a substituted or unsubstituted five-membered and six-membered fused ring,

[0301] R401, R111 and R112 are the same as or different from each other, and are independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or they are combined with adjacent groups to form a substituted or unsubstituted ring,

[0302] r401 is an integer from 0 to 3. When r401 is 2 or more, the substituents in the brackets are the same or different from each other.

[0303] In the above chemical formula D-2,

[0304] X11 and X12 are N,

[0305] R501 to R504 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted aryl group,

[0306] r501 and R502 are each an integer from 0 to 4,

[0307] r503 and r504 are each an integer from 0 to 3,

[0308] When the number of each of r501 to r504 is 2 or more, the two or more R501 to R504 are the same as or different from each other.

[0309] In one embodiment of the present specification, both Y1 and Y2 are NR112, and R112 is a substituted or unsubstituted aryl group.

[0310] In one embodiment of the present specification, both Y1 and Y2 are NR112, and R112 is an aryl group which may be substituted by an alkyl group.

[0311] In one embodiment of the present specification, both Y1 and Y2 are NR112, and R112 is an aryl group which may be substituted by a tert-butyl group.

[0312] In one embodiment of the present specification, the above-mentioned Z1 is a substituted or unsubstituted phenyl group.

[0313] In one embodiment of the present specification, the above-mentioned Z1 is a phenyl group which may be substituted by an alkyl group.

[0314] In one embodiment of the present specification, the above-mentioned Z1 is a phenyl group which may be substituted by a tert-butyl group.

[0315] In one embodiment of the present specification, the above-mentioned Z2 is a substituted or unsubstituted benzothienyl group.

[0316] In one embodiment of the present specification, the above-mentioned Z2 is a benzothienyl group which may be substituted by an alkyl group.

[0317] In one embodiment of the present specification, the above Z2 is a benzothienyl group which may be substituted by a tert-butyl group.

[0318] In one embodiment of the present specification, the above-mentioned R401 is a substituted or unsubstituted alkyl group.

[0319] In one embodiment of the present specification, the above-mentioned R401 is a methyl group.

[0320] In one embodiment of the present specification, R501 and R502 are substituted or unsubstituted alkyl groups.

[0321] In one embodiment of the present specification, R501 and R502 are substituted or unsubstituted tert-butyl groups.

[0322] In one embodiment of the present specification, R503 and R504 are substituted or unsubstituted amino groups.

[0323] As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1 as a host, and may further include another host.

[0324] The organic light-emitting device of the present specification may further include 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 one or more organic layers among the hole injection and transport layer.

[0325] In one embodiment of the present specification, the organic light-emitting device includes an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, and at least one of the two or more organic layers contains the organic compound represented by the above Chemical Formula 1.

[0326] In one embodiment of the present specification, the two or more organic layers may be selected from two or more selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

[0327] In one embodiment of the present specification, the two or more organic layers may be selected from two or more of the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron regulating layer, and a hole blocking layer.

[0328] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0329] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0330] For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.

[0331] (1) Anode / hole transport layer / light-emitting layer / cathode

[0332] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0333] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0334] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0335] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0336] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0337] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0338] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0339] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0340] (10) Anode / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0341] (11) Anode / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0342] (12) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / cathode

[0343] (13) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0344] (14) Anode / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / cathode

[0345] (15) Anode / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0346] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / cathode

[0347] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / electron regulation layer / electron transport layer / electron injection layer / cathode

[0348] (18) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron regulation layer / electron transport and injection layer / cathode

[0349] (19) Anode / hole injection layer / hole transport layer / hole regulation layer / light-emitting layer / electron regulation layer / electron transport and injection layer / cathode / covering layer

[0350] The structure of the organic light-emitting device of the present specification may have the following Figure 1 and Figure 2 The structure shown is not limited thereto.

[0351] Figure 1 The structure of the organic light emitting device is exemplified in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked. In the above structure, the organic compound may be contained in the light emitting layer 6.

[0352] Figure 2The structure of an organic light-emitting device is illustrated, which is sequentially stacked with a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a hole adjustment layer 5, a light-emitting layer 6, an electron adjustment layer 7, an electron transport layer 8, an electron injection layer 9, a cathode 10, and a capping layer 11. In the structure described above, the organic compound may be contained in any one of the hole injection layer 3, the hole transport layer 4, the hole adjustment layer 5, the light-emitting layer 6, the electron adjustment layer 7, the electron transport layer 8, and the electron injection layer 9, for example, the light-emitting layer 6.

[0353] In one embodiment of the present specification, the hole transport layer and the light emitting layer may be disposed adjacent to each other. For example, the hole transport layer and the light emitting layer may be disposed in physical contact with each other.

[0354] In one embodiment of the present specification, the hole regulating layer and the light emitting layer may be disposed adjacent to each other. For example, the hole regulating layer and the light emitting layer may be disposed in physical contact with each other.

[0355] In one embodiment of the present specification, the hole transport layer and the hole regulation layer may be disposed adjacent to each other. For example, the hole transport layer and the hole regulation layer may be disposed in physical contact with each other.

[0356] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that at least one of the organic layers contains the organic compound, ie, the organic compound represented by the above Chemical Formula 1.

[0357] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0358] For example, the organic light-emitting device according to the present specification can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0359] The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole adjustment layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto and may also be a single layer structure. In addition, the organic layer may be made of various polymer materials and by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer to form a smaller number of layers.

[0360] The anode is an electrode for injecting holes. As the anode material, in order to smoothly inject holes into the organic layer, a material with a large work function is preferably used. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO:Al or SnO 2 : Combinations of metals such as Sb and oxides; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, etc., but are not limited to these.

[0361] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. 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; LiF / Al or LiO 2 / Al and other multi-layer structure materials, but not limited to these.

[0362] The hole injection layer is a layer that plays a role in facilitating the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can well receive holes from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, aromatic amine organic matter, hexanitrile hexaazatriphenylene organic matter, tetrafluorobenzonitrile organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited to these. The thickness of the hole injection layer can be 2000 Å. to When the thickness of the hole injection layer is When the hole injection characteristic is reduced, When the thickness of the hole injection layer is too thick, there is an advantage that an increase in driving voltage due to increased hole migration can be prevented.

[0363] In one embodiment of the present specification, the hole injection material may include a hexanitrile hexaazatriphenylene organic substance, and specifically, may include a hexanitrile hexaazatriphenylene substituted with a nitrile group.

[0364] The hole transport layer can play a role in smoothing the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.

[0365] In one embodiment of the present specification, the hole transport material may include a carbazole group-containing arylamine compound.

[0366] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0367] [Chemical formula HT-1]

[0368]

[0369] In the above chemical formula HT-1,

[0370] R315 to R317 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0371] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0372] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.

[0373] According to one embodiment of the present specification, the above R317 may be any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0374] According to one embodiment of the present specification, the R317 may be any one selected from the group consisting of a carbazolyl group, a phenyl group, a biphenyl group, a triphenylene group, and a combination thereof.

[0375] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently may be a substituted or unsubstituted aryl group.

[0376] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently may be a phenyl group or a biphenyl group.

[0377] The hole regulating layer is a layer that regulates the holes transmitted from the hole transport layer to be smoothly injected into the light-emitting layer, and prevents the electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the life and efficiency of the device. It can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport, and known materials can be used without restriction, but specifically, in one embodiment of the present specification, as the hole regulating substance, a compound represented by the chemical formula HT-1 can be included, and more specifically, an arylamine compound containing a carbazole group can be included.

[0378] A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the technical field.

[0379] The electron adjustment layer is a layer for adjusting the smooth injection of electrons transferred from the electron transport layer into the light-emitting layer. It can be formed between the light-emitting layer and the electron injection layer, between the light-emitting layer and the electron transport layer, or between the light-emitting layer and a layer that simultaneously performs electron injection and electron transport. Known materials can be used without restriction.

[0380] Specifically, in one embodiment of the present specification, the electron regulating substance may include a triazine derivative compound.

[0381] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a material with high electron mobility. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, Alq 3 The thickness of the electron transport layer can be 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50 nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0382] In one embodiment of the present specification, the electron transport material may include at least one of lithium quinolate (Liq) and a compound of the following chemical formula ET-1.

[0383] [Chemical formula ET-1]

[0384]

[0385] In the above chemical formula ET-1,

[0386] At least one of Z11 to Z13 is N, and the rest are CH,

[0387] At least one of Z14 to Z16 is N, and the rest are CH,

[0388] L701 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0389] Ar701 to Ar704 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,

[0390] l701 is an integer from 1 to 4. When l701 is a plural number, L701 are the same as or different from each other.

[0391] According to one embodiment of the present specification, the above L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0392] According to one embodiment of the present specification, the above-mentioned L701 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0393] According to one embodiment of the present specification, the above-mentioned L701 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0394] According to one embodiment of the present specification, Ar701 to Ar704 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0395] According to one embodiment of the present specification, Ar701 to Ar704 are substituted or unsubstituted phenyl groups.

[0396] In one embodiment of the present specification, as the above-mentioned electron transport material, lithium quinoline (Liq) and a compound of the following chemical formula ET-1 can be mixed in a weight ratio of 1:9 to 9:1, specifically, can be included in a weight ratio of 2:8 to 8:2, and more specifically, can be included in a weight ratio of 3:7 to 7:3.

[0397] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

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

[0399] In one embodiment of the present specification, the electron injection material may include at least one of magnesium and lithium fluoride (LiF), and specifically, may include both magnesium and lithium fluoride (LiF).

[0400] In one embodiment of the present specification, a capping layer (CPL) may be deposited on the periphery of the cathode, and the capping layer serves to maximize the light extraction effect or prevent degradation of the organic light-emitting device, and may include a capping layer material known in the art. Specifically, the capping layer material may include a carbazole compound.

[0401] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0402] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0403] Below, in order to specifically describe this specification, an embodiment will be cited to describe in detail. However, the embodiments according to this specification can be deformed into various different forms, and it is not interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely describe this specification to those skilled in the art.

[0404] Preparation Example 1. Synthesis of Intermediates B1 to B12

[0405]

[0406] Ar2 has the same meaning as in the above Chemical Formula 1.

[0407] After adding 9-bromoanthracene-1,2,3,4,5,6,7,10-d9 (1 equivalent) and SM1 (1.1 equivalent) to tetrahydrofuran (THF, 10 times of 9-bromoanthracene-1,2,3,4,5,6,7,10-d9), add 2M potassium carbonate aqueous solution (30% volume ratio relative to THF), add tetrakis(triphenylphosphine)palladium (2 mol%), and heat and stir for 10 hours. After the temperature is lowered to room temperature and the reaction is terminated, the potassium carbonate aqueous solution is separated and removed, and the tetrahydrofuran is removed by vacuum distillation. After being dissolved in chloroform, it is added to a separatory funnel, washed with distilled water 3 times, and the organic layer is dried over anhydrous magnesium sulfate. Then, the chloroform is removed under reduced pressure, and recrystallized with ethyl acetate (EA) to obtain compound A in a solid state.

[0408] After the above compound A (1 equivalent) was dissolved in chloroform (10 times the amount of compound A), a solution of n-bromosuccinimide (1 equivalent, dissolved at a concentration of 3.5 M) dissolved in dimethylformamide was slowly added dropwise. After reacting at room temperature for 2 hours, 20% Na 2 S 2 O 3 The aqueous solution was added dropwise in an amount of 1 / 4 of the volume of chloroform used for the first time, and the organic layer was separated using a separatory funnel and washed three times with distilled water. Anhydrous magnesium sulfate was added to the chloroform solution to remove residual water, and the chloroform was removed by vacuum distillation, and recrystallized in ethyl acetate (EA) to obtain compound B in a solid state.

[0409] In the synthesis method of the above-mentioned compounds A and B, intermediates B1 to B12 were synthesized by the same method except that SM1 and compound A were changed as shown in the following Tables 1 and 2.

[0410]

Table 1

[0411]

[0412]

[0413]

[0414]

Table 2

[0415]

[0416]

[0417]

[0418] Preparation Example 2. Synthesis of Intermediates D1 to D17

[0419]

[0420] Ar1 is the same as defined in the above Chemical Formula 1, and Nf is a perfluorobutane-1-sulfonyl group.

[0421] SM3 (1 eq.) and SM4 (1.1 eq.) were added to 1,4-dihydro- After adding 2M potassium phosphate aqueous solution (1,4-dioxane, 10 times relative to SM3), After adding bis(tri-tert-butylphosphine)palladium(0) (2 mol%), the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the potassium phosphate aqueous solution was separated and removed, and 1,4-dihydro-1,4-dihydro-1,4-diol was added. After being dissolved in chloroform, the mixture was added to a separatory funnel, washed three times with distilled water, and the organic layer was dried over anhydrous magnesium sulfate. Then, the chloroform was removed by decompression, and the mixture was recrystallized from ethyl acetate (EA) / hexane (Hexane) to obtain compound C in a solid state.

[0422] After dissolving compound C (1 equivalent) in acetonitrile (AN, 20 times relative to compound C), potassium carbonate (2.5 equivalent) aqueous solution (30% wt) was added, and 1.5 equivalents of perfluorobutane-1-sulfonyl fluoride (Nonafluorobutan-1-sulfonic fluoride) (normal temperature) was slowly added dropwise while stirring. After 5 hours, after confirming that the reaction was completed, acetonitrile was removed by vacuum distillation, dissolved in chloroform, and extracted with water several times. After drying the organic layer with anhydrous magnesium sulfate, the organic solvent was removed by vacuum distillation, and purified by recrystallization using ethanol to produce compound D.

[0423] Intermediates D1 to D17 were synthesized by the same method as that of the above-mentioned synthesis of compounds C and D, except that SM3, SM4 and compound C were changed as shown in the following Tables 3 and 4.

[0424]

Table 3

[0425]

[0426]

[0427]

[0428]

Table 4

[0429]

[0430]

[0431]

[0432]

[0433] Preparation Example 3. Synthesis of Intermediates E1 to E9

[0434]

[0435] Ar1 is the same as defined in the above Chemical Formula 1.

[0436] After adding SM5 (1 equivalent) and SM6 (1.05 equivalents) to tetrahydrofuran (THF, 10 times relative to SM5), add 2M potassium carbonate aqueous solution (30% volume ratio relative to THF), add tetrakis(triphenylphosphine)palladium (2 mol%), and heat and stir for 10 hours. After the temperature is lowered to room temperature and the reaction is terminated, the potassium carbonate aqueous solution is separated and removed by layer separation, and the tetrahydrofuran is removed by reduced pressure distillation. After being dissolved in chloroform, it is added to a separatory funnel, washed with distilled water 3 times, and the organic layer is dried over anhydrous magnesium sulfate. Then, the chloroform is removed by reducing pressure, and recrystallization is performed with ethyl acetate (EA) and hexane (Hex) to obtain compound E in a solid state.

[0437] Intermediates E1 to E9 were synthesized by the same method as that of the above-mentioned synthesis of compound E, except that SM6 was changed as shown in Table 5 below.

[0438]

Table 5

[0439]

[0440]

[0441] Preparation Example 4. Synthesis of Intermediates F1 to F26

[0442]

[0443] Ar1 is the same as defined in the above Chemical Formula 1.

[0444] The intermediate D or E (1 equivalent) synthesized in the above-mentioned Preparation Example 2 or 3 and bis(pinacolato)diboron (1.5 equivalent) were added to 1,4-diborane. Potassium acetate (3.0 equivalents) was added to 12 times the amount of intermediate D or E in 1,4-dioxane, followed by stirring and refluxing. Palladium acetate (0.02 equivalents) and tricyclohexylphosphine (0.04 equivalents) were added to 1,4-dioxane. After stirring in oxane for 5 minutes, the mixture was added. After 2 hours, completion of the reaction was confirmed, and the mixture was cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol, thereby producing the above-mentioned compound F.

[0445] In the synthesis method of the above-mentioned compound F, except that "compound D or E" was changed as shown in the following Table 6, the intermediates F1 to F26 were synthesized by the same method.

[0446]

Table 6

[0447]

[0448]

[0449]

[0450]

[0451] Preparation Example 5. Synthesis of Compounds 1 to 25

[0452]

[0453] R1 to R8, Ar1 and Ar2 are the same as defined in Chemical Formula 1.

[0454] The intermediate B (1 equivalent) synthesized in the above-mentioned preparation example 1 and the intermediate F (1.1 equivalent) synthesized in the above-mentioned preparation example 4 were added to tetrahydrofuran (10 times relative to the intermediate A), and then a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, and tetrakis (triphenylphosphine) palladium (0.02 equivalent) was added, and then stirred and refluxed for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed and the layers were separated. Then, the solvent was removed and purified by recrystallization using toluene, thereby producing the final product.

[0455] In the synthesis method of the above-mentioned products, compounds 1 to 25 were synthesized by the same method except that compound B and compound F were changed as shown in the following Table 7.

[0456]

Table 7

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463] Preparation Example 6. Synthesis of Compounds 26 to 28

[0464]

[0465] R1 to R8, Ar1 and Ar2 are the same as defined in the above Chemical Formula 1.

[0466] In the synthesis method of the above-mentioned Production Example 5, Compound G (Intermediates G1 to G3) was synthesized by the same method except that Compound B and Compound F were changed as shown in the following Table 8.

[0467] Compound G and AlCl 3 (20%wt) added to C 6 D 6 (20 times of compound G) and stirred for 2 hours. After the reaction was completed, D 2 O (1.5 times of compound G), stirred for 30 minutes, and then trimethylamine (D 2 O). The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was washed with MgSO 4 After drying, the product was recrystallized from ethyl acetate to obtain a final product.

[0468] In the synthesis method of the above products, compounds 26 to 28 were synthesized by the same method except that compound G was changed as shown in the following Table 9.

[0469]

Table 8

[0470]

[0471]

Table 9

[0472]

[0473] Experimental Example 1

[0474] ITO (indium tin oxide) / Ag / ITO as the anode The substrate to be deposited was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water in which a dispersant was dissolved, and washed using ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in sequence with solvents of isopropanol, acetone, and methanol, and then dried.

[0475] On the above anode, HAT-CN was A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HTL1, a substance that transports holes, is deposited with a thickness of 1000 mm / s. Vacuum evaporation is performed to form a hole transport layer. Then, HTL2 Next, the above-mentioned compound 1 as the main body and BD-1 as the dopant (weight ratio 97:3) were simultaneously vacuum-deposited to form a 20nm thick light-emitting layer. The electron regulating layer was formed by evaporation, and the compound ETL1 and lithium quinolate (Liq) were mixed in a ratio of 7:3 to form a layer having a thickness of The electron transport layer of A film of magnesium and lithium fluoride (LiF) with a thickness of 100 Å is formed as an electron injection layer.

[0476] As the cathode, magnesium and silver (1:4) were used to form Then, CP1 was evaporated as a cover layer. Thus, the device is completed. In the above process, the evaporation rate of the organic matter is maintained at

[0477] Examples 1 to 28

[0478] An organic light-emitting device was prepared by the same method as in Example 1, except that the compounds listed in Table 10 below were used instead of Compound 1 of Example 1 as the host of the light-emitting layer and BD-1 as the dopant. At this time, Compounds 1 to 28 represented by Chemical Formula 1 of the present invention in the following structures were prepared by the same processes as in Preparation Examples 1 to 6.

[0479] In the organic light-emitting devices manufactured in the above Examples 1 to 28 and Comparative Examples 1 to 9, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2The time (LT) to reach 95% of the initial brightness was measured at a current density of 1.38 W / m. The results are shown below.

[0480] Table 10.

[0481]

[0482]

Table 10

[0483]

[0484] According to the above Table 1, it can be confirmed that compared with the organic light-emitting devices of Comparative Examples 1 and 2 using compounds a and b in which dibenzofuran bound to an anthracene nucleus substituted with deuterium is substituted with a carbazole group or a benzofuran group, Examples 1 to 28 using compounds 1 to 28 according to Chemical Formula 1 of the present application have low driving voltage, high luminous efficiency, and excellent life.

[0485] In addition, it can be confirmed that the driving voltage, luminous efficiency and life of the organic light-emitting devices of Examples 1 to 28 of the present application are significantly superior to those of the organic light-emitting devices of Comparative Examples 3 to 6 using compounds c to f in which the anthracene nucleus is not substituted with deuterium or aromatic groups, and the organic light-emitting devices of Comparative Examples 7 and 8 using compounds g and h in which dibenzofuran bound to the anthracene nucleus substituted with deuterium is substituted only with phenyl groups, and the organic light-emitting device of Comparative Example 9 using compound i in which the binding position of dibenzofuran bound to the anthracene nucleus is different from the binding position of dibenzofuran in Chemical Formula 1 of the present application have low driving voltage, high luminous efficiency and excellent life compared with Examples 1 to 28 of the present application.

[0486] In summary, it can be confirmed that by using the organic compound according to the present invention, excellent characteristics are exhibited in terms of driving voltage, luminous efficiency, and life span of the organic light-emitting device.

Claims

1. An organic compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R1 to R8 are the same or different from each other, and are each independently deuterium, or a substituted or unsubstituted aryl group, R9 and R10 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, Ar1 is any one of the following heterocyclic groups: i) a substituted or unsubstituted five-membered or six-membered monocyclic heterocyclic group containing at least one of N, O and S as a heteroelement; ii) a heterocyclic group formed by condensing two substituted or unsubstituted five-membered or six-membered rings containing at least one of N and S as a heteroelement; iii) a heterocyclic group formed by condensing three or more substituted or unsubstituted rings containing at least one of O and S as a heteroelement; and iv) a heterocyclic group formed by condensing three or more substituted or unsubstituted six-membered rings containing N as a heteroelement, Ar2 is a substituted or unsubstituted aryl group, m is an integer from 1 to 3, n is an integer from 1 to 3, When m and n are 2 or more, two or more R9 and R10 are the same as or different from each other.

2. The organic compound according to claim 1, wherein The Ar1 is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] X1, X3 and X4 are O or S, X2 is N or CR, p and q are each an integer from 0 to 2, When p is 0, X2 is N, R is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a part connected to the dibenzofuran of the chemical formula 1, G1 to G4 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 heterocyclic group, g1 is 1 to 3, g2 is 1 to 8, g3 is 1 to 11, g4 is 1 to 9, When g1 to g4 are 2 or more, the two or more G1 to G4 are the same as or different from each other. * is a site connected to dibenzofuran of Chemical Formula 1.

3. The organic compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-4: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] In the chemical formula 2-1 to the chemical formula 2-4, The definitions of R1 to R10, Ar1, Ar2, m and n are the same as those in Chemical Formula 1.

4. The organic compound according to claim 1, wherein The R1 to R8 are all deuterium.

5. The organic compound according to claim 1, wherein The R9 and R10 are the same as or different from each other, and are independently hydrogen or deuterium.

6. The organic compound according to claim 1, wherein The Ar2 is a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms.

7. The organic compound according to claim 1, wherein Ar2 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted fluorenyl.

8. The organic compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following compounds:

9. An organic light-emitting device, wherein: include: An anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 8.

10. The organic light emitting device according to claim 9, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound.

11. The organic light emitting device according to claim 9, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as a host.

12. The organic light emitting device according to claim 11, wherein: The light-emitting layer further includes a dopant.

13. The organic light emitting device according to claim 9, wherein: The organic layer further includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.

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