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. 10-2023-0117446 filed with the Korean Patent Office on September 5, 2023 and Korean Patent Application No. 10-2024-0081851 filed with the Korean Patent Office on June 24, 2024, the entire contents of which are incorporated into this specification.

[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) U.S. Patent Publication No. 2022-0153759 Summary of the invention

[0008] Technical issues

[0009] Provided in the present specification are organic compounds and organic light-emitting devices including the same.

[0010] Solution to the problem

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

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R 1 To R16 At least one of the following chemical formula 2-1 or chemical formula 2-2,

[0016] The above R 1 To R 16 The groups that are not the following chemical formula 2-1 or chemical formula 2-2 are the same or different, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or selectively combine with adjacent groups to form a substituted or unsubstituted ring,

[0017] The above R 4 With R 5 When they are bound to each other, they are connected through the -(X)a- binding group.

[0018] The above R 9 With R 10 When they are bound to each other, they are connected through the -(Y)b-binding group.

[0019] The above X and Y are the same or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R",

[0020] R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,

[0021] a and b are 0 or 1 respectively,

[0022] a+b is 1 or 2,

[0023]

[0024]

[0025] In the above Chemical Formula 2-1 and Chemical Formula 2-2,

[0026] * is the site that binds to the above chemical formula 1,

[0027] L 1 is a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms,

[0028] R 17 To R 19 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic,

[0029] o is an integer from 1 to 8,

[0030] p is an integer from 1 to 7,

[0031] q is an integer from 1 to 8,

[0032] m is 0 or 1,

[0033] 1≤m+o≤8,

[0034] 1≤m+p≤7,

[0035] When the above o is 2 or more, the above two or more R 17 Same or different from each other,

[0036] When the above p is 2 or more, the above two or more R 17 Same or different from each other,

[0037] When the above q is 2 or more, the above two or more R 18 The same as or different from each other.

[0038] 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.

[0039] Effects of the Invention

[0040] 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

[0041] 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 9 are stacked in this order is shown.

[0042] Figure 2 The diagram shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in this order.

[0043] Explanation of symbols

[0044] 1: Substrate

[0045] 2: Anode

[0046] 3: Hole injection layer

[0047] 4: Hole transport layer

[0048] 5: Electron blocking layer

[0049] 6: Luminous layer

[0050] 7: Hole blocking layer

[0051] 8: Electron injection and transport layer

[0052] 9: Cathode DETAILED DESCRIPTION

[0053] Next, this specification is described in more detail.

[0054] 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.

[0055] 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.

[0056] In the present specification, "*" indicates a position bonded to a chemical formula or a compound.

[0057] In the present specification, examples of substituents are described below, but are not limited thereto.

[0058] 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.

[0059] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a silyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents of an alkenyl group, an amine group, an aryl group or a heterocyclic group, or may be substituted with a substituent formed by connecting two or more substituents of the substituents exemplified above, or may not have any substituent. For example, "a substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.

[0060] In the present specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an amino group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heterocyclic group, or is substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or has no substituent.

[0061] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0062] Examples of the above substituents are described below, but are not limited thereto.

[0063] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0064] In the present specification, the silyl group can be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0065] 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.

[0066] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but is not limited thereto.

[0067] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all of linear and branched forms.

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

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

[0070] 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.

[0071] In this specification, an amine group is -NH 2 , the above-mentioned alkyl, aryl, heterocyclic group, alkenyl, cycloalkyl, and combinations thereof may be substituted in the above-mentioned amine group. The number of carbon atoms of the above-mentioned substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned amine group is 1 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned amine group is 1 to 10. As specific examples of substituted amine groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0072] 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.

[0073] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group and the arylamine group.

[0074] In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylthio group and alkylsulfonyl group.

[0075] In the present specification, the above description about the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.

[0076] 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.

[0077] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0078] 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.

[0079] In the present specification, the same explanation as for the above-mentioned heteroaryl group is applicable to the heteroarylene group except that the heteroarylene group is divalent.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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, diazines, 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.

[0086] 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.

[0087] Next, the organic compound of the following Chemical Formula 1 will be described in detail.

[0088] [Chemical formula 1]

[0089]

[0090] In the above chemical formula 1,

[0091] R 1 To R 16 At least one of the following chemical formula 2-1 or chemical formula 2-2,

[0092] The above R 1 To R 16 The groups that are not the following chemical formula 2-1 or chemical formula 2-2 are the same or different, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or selectively combine with adjacent groups to form a substituted or unsubstituted ring,

[0093] The above R 4 With R 5 When they are bound to each other, they are connected through the -(X)a- binding group.

[0094] The above R 9 With R 10 When they are bound to each other, they are connected through the -(Y)b-binding group.

[0095] The above X and Y are the same or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R",

[0096] R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,

[0097] a and b are 0 or 1 respectively,

[0098] a+b is 1 or 2,

[0099]

[0100] In the above Chemical Formula 2-1 and Chemical Formula 2-2,

[0101] * is the site that binds to the above chemical formula 1,

[0102] L 1 is a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms,

[0103] R 17 To R 19 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic,

[0104] o is an integer from 1 to 8,

[0105] p is an integer from 1 to 7,

[0106] q is an integer from 1 to 8,

[0107] m is 0 or 1,

[0108] 1≤m+o≤8,

[0109] 1≤m+p≤7,

[0110] When the above o is 2 or more, the above two or more R 17 Same or different from each other,

[0111] When the above p is 2 or more, the above two or more R 17 Same or different from each other,

[0112] When the above q is 2 or more, the above two or more R 18 The same as or different from each other.

[0113] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound of any one of the following Chemical Formulas 1-1 to 1-6.

[0114] [Chemical formula 1-1]

[0115]

[0116] [Chemical formula 1-2]

[0117]

[0118] [Chemical formula 1-3]

[0119]

[0120] [Chemical formula 1-4]

[0121]

[0122] [Chemical formula 1-5]

[0123]

[0124] [Chemical formula 1-6]

[0125]

[0126] In the above Chemical Formulas 1-1 to 1-6, R 1 To R 3 , R 6 To R 16 The definitions of R, R' and R" are the same as those in the above Chemical Formula 1.

[0127] In one embodiment of the present specification, the above Chemical Formula 2-1 is any one of the following Chemical Formulas 2-1-1 to 2-1-5.

[0128]

[0129] [Chemical formula 2-1-5]

[0130]

[0131] In the above Chemical Formulas 2-1-1 to 2-1-5, L 1 The definitions of o and q are the same as those in the above chemical formula 2-1,

[0132] R 17 and R 18 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0133] In one embodiment of the present specification, the above Chemical Formula 2-2 is any one of the following Chemical Formulas 2-2-1 to 2-2-4.

[0134]

[0135] In the above Chemical Formulas 2-2-1 to 2-2-4, L 1 The definitions of and p are the same as those in the above chemical formula 2-2,

[0136] R 17 and R 19 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0137] In one embodiment of the present specification, the above R 1 To R 16 At least one of the above chemical formula 2-1 or chemical formula 2-2, the above R 1 To R 16 The groups not being the above Chemical Formula 2-1 or Chemical Formula 2-2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0138] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-1, and the above R 1 To R 16 The groups other than those of the above Chemical Formula 2-1 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0139] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-1, and the above R 1 To R 16 The groups not belonging to the above Chemical Formula 2-1 are the same as or different from each other and are independently hydrogen or deuterium.

[0140] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-1, and the above R 1 To R 16 The group not being a member of the above chemical formula 2-1 is deuterium.

[0141] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-1, and the above R 1 To R 16 The group not being a member of the above chemical formula 2-1 is hydrogen.

[0142] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-2, and the above R 1 To R 16 The groups not being those of the above Chemical Formula 2-2 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0143] In one embodiment of the present specification, the above R 1 To R 16At least one of them is the above chemical formula 2-2, and the above R 1 To R 16 The groups not being the above chemical formula 2-2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0144] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-2, and the above R 1 To R 16 The group not being a member of the above chemical formula 2-2 is deuterium.

[0145] In one embodiment of the present specification, the above R 1 To R 16 At least one of them is the above chemical formula 2-2, and the above R 1 To R 16 The group not being a member of the above chemical formula 2-2 is hydrogen.

[0146] In one embodiment of the present specification, X and Y are the same as or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R".

[0147] In one embodiment of the present specification, X and Y are the same as or different from each other, and are each independently a direct bond, O, S, CR'R", or SiR'R".

[0148] In one embodiment of the present specification, the above-mentioned X is a direct bond, O, S, CR'R", or SiR'R".

[0149] In one embodiment of the present specification, the above-mentioned Y is a direct bond, O, S, CR'R", or SiR'R".

[0150] In one embodiment of the present specification, the above-mentioned X is a direct bond.

[0151] In one embodiment of the present specification, the above-mentioned X is O.

[0152] In one embodiment of the present specification, the above-mentioned X is S.

[0153] In one embodiment of the present specification, the above-mentioned X is CR'R".

[0154] In one embodiment of the present specification, the above-mentioned X is NR'.

[0155] In one embodiment of the present specification, the above-mentioned X is SiR'R".

[0156] In one embodiment of the present specification, the above-mentioned Y is a direct bond.

[0157] In one embodiment of the present specification, the above-mentioned Y is O.

[0158] In one embodiment of the present specification, the above-mentioned Y is S.

[0159] In one embodiment of the present specification, the above-mentioned Y is CR'R".

[0160] In one embodiment of the present specification, the above-mentioned Y is NR'.

[0161] In one embodiment of the present specification, the above-mentioned Y is SiR'R".

[0162] In one embodiment of the present specification, the above R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0163] In one embodiment of the present specification, R' and R" are the same or different and are 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.

[0164] In one embodiment of the present specification, R' and R" are the same or different and are 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.

[0165] In one embodiment of the present specification, R' and R" are the same or different and are 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 10 carbon atoms.

[0166] In one embodiment of the present specification, the above R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium or methyl.

[0167] In one embodiment of the present specification, both R' and R" are hydrogen.

[0168] In one embodiment of the present specification, both R' and R" are deuterium.

[0169] In one embodiment of the present specification, both R' and R" are methyl groups.

[0170] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 30% or more.

[0171] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 40% or more.

[0172] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 50% or more.

[0173] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 60% or more.

[0174] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 70% or more.

[0175] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 80% or more.

[0176] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound having a deuterium substitution rate of 90% or more.

[0177] In one embodiment of the present specification, the above Chemical Formula 1 is an organic compound with a deuterium substitution rate of 100%.

[0178] In one embodiment of the present specification, the above-mentioned a is 0 or 1.

[0179] In one embodiment of the present specification, the above b is 0 or 1.

[0180] In one embodiment of the present specification, a is 1 and b is 0.

[0181] In one embodiment of the present specification, a is 0 and b is 1.

[0182] In one embodiment of the present specification, a is 1 and b is 1.

[0183] In one embodiment of the present specification, the above-mentioned a+b is 1 or 2.

[0184] In one embodiment of the present specification, the above L 1 It is a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0185] In one embodiment of the present specification, the above L 1 It is a directly bonded or substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0186] In one embodiment of the present specification, the above L 1 It is an arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0187] In one embodiment of the present specification, the above L 1 It is an arylene group having 6 to 20 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0188] In one embodiment of the present specification, the above L 1 It is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0189] In one embodiment of the present specification, the above L 1 It is a direct bond, a phenylene group which may be substituted by deuterium, or a biphenylene group which may be substituted by deuterium.

[0190] In one embodiment of the present specification, the above L 1 It is a direct bond, a phenylene group or a biphenylene group.

[0191] In one embodiment of the present specification, the above L 1 For direct bonding.

[0192] In one embodiment of the present specification, the above L 1 is a substituted or unsubstituted phenylene group.

[0193] In one embodiment of the present specification, the above L 1 In the case of a substituted or unsubstituted phenylene group, the phenylene group is at least one of ortho-substituted, meta-substituted and para-substituted.

[0194] In one embodiment of the present specification, the above L 1 In the case of a substituted or unsubstituted phenylene group, the above phenylene group is ortho-substituted or meta-substituted.

[0195] In one embodiment of the present specification, the above L 1 In the case of a substituted or unsubstituted phenylene group, the above phenylene group is ortho-substituted or para-substituted.

[0196] In one embodiment of the present specification, the above L 1 In the case of a substituted or unsubstituted phenylene group, the above phenylene group is meta-substituted or para-substituted.

[0197] In one embodiment of the present specification, the above L 1 is a substituted or unsubstituted biphenylene group.

[0198] In one embodiment of the present specification, the above R 17 To R 19 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0199] In one embodiment of the present specification, the above R 17 To R19 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0200] In one embodiment of the present specification, the above R 17 To R 19 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0201] In one embodiment of the present specification, the above R 17 To R 19 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 aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0202] In one embodiment of the present specification, the above R 17 To R 19 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 aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0203] In one embodiment of the present specification, the above R 17 To R 19 They 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0204] In one embodiment of the present specification, the above R 17 To R 19 They 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.

[0205] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other and are each independently hydrogen, deuterium, an aryl group having 6 to 30 carbon atoms which may be substituted or not substituted by deuterium, or a heterocyclic group having 2 to 30 carbon atoms which may be substituted or not substituted by deuterium.

[0206] In one embodiment of the present specification, the above R 17 To R 19 They 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.

[0207] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0208] In one embodiment of the present specification, the above R 17 To R 19 For hydrogen.

[0209] In one embodiment of the present specification, the above R 17 To R 19 For deuterium.

[0210] In one embodiment of the present specification, the above R 17 is hydrogen or deuterium.

[0211] In one embodiment of the present specification, the above R 18 is hydrogen or deuterium.

[0212] In one embodiment of the present specification, the above R 19 is hydrogen or deuterium.

[0213] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 2 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 and containing O, S or N.

[0214] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 2 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 20 carbon atoms and containing O, S or N.

[0215] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 2 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 10 carbon atoms and containing O, S or N.

[0216] In one embodiment of the present specification, the above R 17 To R 19 The same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted naphthobenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

[0217] In one embodiment of the present specification, the above R 17 To R 19 The same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

[0218] In one embodiment of the present specification, the above R 17 To R 19 The same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, or substituted or unsubstituted dibenzothienyl.

[0219] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted dibenzofuranyl.

[0220] In one embodiment of the present specification, the above R 17 To R 19 are the same as or different from each other and are each independently hydrogen, deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, or dibenzofuranyl substituted or unsubstituted by deuterium.

[0221] In one embodiment of the present specification, the above R 17 and R 18 Each is independently hydrogen, deuterium, phenyl which may be substituted by deuterium, biphenyl which may be substituted by deuterium, or dibenzofuranyl which may be substituted by deuterium.

[0222] In one embodiment of the present specification, the above R 17 and R 19 Each is independently hydrogen, deuterium, phenyl which may be substituted by deuterium, biphenyl which may be substituted by deuterium, or dibenzofuranyl which may be substituted by deuterium.

[0223] In one embodiment of the present specification, the above R 18 and R 19 Each is independently hydrogen, deuterium, phenyl which may be substituted by deuterium, biphenyl which may be substituted by deuterium, or dibenzofuranyl which may be substituted by deuterium.

[0224] In one embodiment of the present specification, the above R 17 It is hydrogen or phenyl which may be substituted by deuterium.

[0225] In one embodiment of the present specification, the above R 17 It is hydrogen or a dibenzofuranyl group which may be substituted by deuterium.

[0226] In one embodiment of the present specification, the above R 17 It is hydrogen or a dibenzothienyl group which may be substituted by deuterium.

[0227] In one embodiment of the present specification, the above R 18 It is hydrogen or phenyl which may be substituted by deuterium.

[0228] In one embodiment of the present specification, the above R 18 It is hydrogen or a dibenzofuranyl group which may be substituted by deuterium.

[0229] In one embodiment of the present specification, the above R 18 It is hydrogen or a dibenzothienyl group which may be substituted by deuterium.

[0230] In one embodiment of the present specification, the above R 19 It is hydrogen or phenyl which may be substituted by deuterium.

[0231] In one embodiment of the present specification, the above R 19 is a phenyl group which may be substituted with deuterium. 19 It is phenyl.

[0232] In one embodiment of the present specification, the above o is an integer from 1 to 8. In one embodiment of the present specification, the above o is 8.

[0233] In one embodiment of the present specification, the above-mentioned o is 7.

[0234] In one embodiment of the present specification, the above-mentioned o is 6.

[0235] In one embodiment of the present specification, the above-mentioned o is 5.

[0236] In one embodiment of the present specification, the above-mentioned o is 4.

[0237] In one embodiment of the present specification, the above-mentioned o is 3.

[0238] In one embodiment of the present specification, the above-mentioned o is 2.

[0239] In one embodiment of the present specification, the above-mentioned o is 1.

[0240] In one embodiment of the present specification, the above p is an integer of 1 to 7.

[0241] In one embodiment of the present specification, the above-mentioned p is 7.

[0242] In one embodiment of the present specification, the above-mentioned p is 6.

[0243] In one embodiment of the present specification, the above-mentioned p is 5.

[0244] In one embodiment of the present specification, the above-mentioned p is 4.

[0245] In one embodiment of the present specification, the above-mentioned p is 3.

[0246] In one embodiment of the present specification, the above-mentioned p is 2.

[0247] In one embodiment of the present specification, the above-mentioned p is 1.

[0248] In one embodiment of the present specification, the above q is an integer of 1 to 8.

[0249] In one embodiment of the present specification, the above q is 8.

[0250] In one embodiment of the present specification, the above q is 7.

[0251] In one embodiment of the present specification, the above q is 6.

[0252] In one embodiment of the present specification, the above q is 5.

[0253] In one embodiment of the present specification, the above q is 4.

[0254] In one embodiment of the present specification, the above q is 3.

[0255] In one embodiment of the present specification, the above q is 2.

[0256] In one embodiment of the present specification, the above q is 1.

[0257] In one embodiment of the present specification, the above m is 0 or 1.

[0258] In one embodiment of the present specification, the above m is 1.

[0259] In one embodiment of the present specification, the above m is 0.

[0260] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following compounds.

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274] The organic compound of Chemical Formula 1 according to one embodiment of the present specification can produce a core structure as described in the following production examples. The substituents can be bonded 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.

[0275] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the organic compound of 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 shown above.

[0276] In addition, the present specification provides an organic light-emitting device including the above-mentioned organic compound.

[0277] 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.

[0278] 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.

[0279] In the organic light-emitting device of the present specification, the organic light-emitting device includes a light-emitting layer, and the light-emitting layer may include the organic compound.

[0280] For example, the organic compound of the above Chemical Formula 1 may be included as a host of the light emitting layer.

[0281] In the organic light-emitting device of the present specification, the light-emitting layer contains the organic compound as a host and may further contain a dopant.

[0282] In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the organic compound represented by the above Chemical Formula 1.

[0283] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the organic compound represented by Chemical Formula 1.

[0284] 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 injection and transport 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.

[0285] 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.

[0286] 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.

[0287] 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.

[0288] 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 9 are sequentially stacked. In the structure described above, the compound may be contained in the light-emitting layer 6.

[0289] Figure 2 The 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, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9. In the structure described above, the compound may be contained in any one of the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, and the electron injection and transport layer 8, for example, in the light-emitting layer 6.

[0290] 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 material layers contains the above compound, that is, the organic compound represented by the above Chemical Formula 1.

[0291] 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.

[0292] 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, an electron blocking layer, a light-emitting 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.

[0293] The organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0294] 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.

[0295] 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.

[0296] 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. It is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0297] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0298] [Chemical formula HI-1]

[0299]

[0300] In the above chemical formula HI-1,

[0301] R315 to R317 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0302] 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.

[0303] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, the two or more R316 are the same as or different from each other.

[0304] According to one embodiment of the present specification, the above R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0305] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazolyl group, a phenyl group, a biphenyl group, a triphenylene group, and a combination thereof.

[0306] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0307] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently phenyl or biphenyl, or are combined with adjacent groups to form an indene substituted with a methyl group.

[0308] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0309]

[0310] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2, but the present invention is not limited thereto.

[0311] [Chemical formula HI-2]

[0312]

[0313] In the above chemical formula HI-2,

[0314] R401 to R403 are the same as or different from each other and are each independently a halogen group,

[0315] R401 to R403 are 4.

[0316] According to one embodiment of the present specification, R401 to R403 are F.

[0317] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0318]

[0319] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.

[0320] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2 at a weight ratio of 1:99 to 99:1.

[0321] 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.

[0322] According to one embodiment of the present specification, the hole transport layer includes the compound represented by the chemical formula HI-1, but is not limited thereto.

[0323] An electron blocking layer may be provided between the hole transport layer and the light emitting layer.

[0324] According to one embodiment of the present specification, the electron blocking layer may include the compound of Chemical Formula 1.

[0325] The electron blocking layer may use the above-mentioned compounds or materials known in the art.

[0326] The light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0327] The host material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0328] In one embodiment of the present specification, the light-emitting layer includes the organic compound of Chemical Formula 1 as a main component.

[0329] In one embodiment of the present specification, the light-emitting layer includes the organic compound of the above Chemical Formula 1 as a host, and further includes one or more hosts different from the above Chemical Formula 1.

[0330] In one embodiment of the present specification, a host different from the compound of the above Chemical Formula 1 is represented by the following Chemical Formula EN.

[0331] [Chemical formula EN]

[0332]

[0333] In the above chemical formula EN,

[0334] X1 is O or S,

[0335] Ra to Rc 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 aryl group, or a substituted or unsubstituted heteroaryl group.

[0336] In one embodiment of the present specification, the above Ra to Rc are the same as or different from each other, and are each independently hydrogen or deuterium.

[0337] In one embodiment of the present specification, the above-mentioned Ra to Rc are hydrogen.

[0338] In one embodiment of the present specification, the chemical formula EN is the following structure.

[0339]

[0340] In the organic light-emitting device of the present specification, the light-emitting layer contains the organic compound as a host and may further contain a dopant.

[0341] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99, specifically, in a weight ratio of 99:1 to 50:50, and more specifically, in a weight ratio of 99:1 to 95:5.

[0342] When the above-mentioned light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances 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) can be used; 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 2ppy) 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.

[0343] According to one embodiment of the present specification, the dopant is a metal coordination compound.

[0344] According to one embodiment of the present specification, the dopant is a platinum coordination compound.

[0345] According to one embodiment of the present specification, the dopant is an iridium complex.

[0346] According to one embodiment of the present specification, the dopant is represented by the following chemical formula D-1 or D-2, but is not limited thereto.

[0347] [Chemical formula D-1]

[0348]

[0349] [Chemical formula D-2]

[0350]

[0351] In the above chemical formulas D-1 and D-2,

[0352] M is a transition metal,

[0353] A1, A3, A5, A6, K1, K2 and K3 are the same as or different from each other, and are each independently a direct bond, O, S, a divalent ester group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkenyl group, a substituted or unsubstituted divalent allyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0354] A2 and A4 are the same as or different from each other, and are each independently a direct bond, N, a substituted or unsubstituted trivalent alkylene group, a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heteroaryl group,

[0355] n is 1 or 2. When n is 2, the structures in the brackets are the same as or different from each other.

[0356] According to one embodiment of the present specification, the above-mentioned M is iridium or platinum.

[0357] According to one embodiment of the present specification, the dopant may be selected from the following structural formulas, but is not limited thereto.

[0358]

[0359]

[0360]

[0361]

[0362] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.

[0363] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0364] According to one embodiment of the present specification, the hole blocking layer includes a compound represented by the chemical formula EN, but is not limited thereto.

[0365] The electron transport layer or electron injection and transport layer can play a role in smoothing the electron transport. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with high electron mobility are suitable. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, Alq 3 complexes, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these.

[0366] 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.

[0367] 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.

[0368] According to one embodiment of the present specification, the electron injection and transport layer includes a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0369] [Chemical formula ET-1]

[0370]

[0371] In the above chemical formula ET-1,

[0372] At least one of Z11 to Z13 is N, and the rest are CH,

[0373] At least one of Z21 to Z23 is N, and the others are CH,

[0374] L601 and L602 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0375] Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0376] In one embodiment of the present specification, all of Z11 to Z13 are N.

[0377] In one embodiment of the present specification, all of Z21 to Z23 are N.

[0378] In one embodiment of the present specification, L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms. In one embodiment of the present specification, L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 12 carbon atoms.

[0379] In one embodiment of the present specification, L601 and L602 are substituted or unsubstituted phenylene groups.

[0380] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0381] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0382] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 12 carbon atoms.

[0383] In one embodiment of the present specification, Ar601 to Ar604 are substituted or unsubstituted phenyl groups.

[0384] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0385] In one embodiment of the present specification, the chemical formula ET-1 is the following structure.

[0386]

[0387] In one embodiment of the present specification, the electron injection and transport layer may further include a metal coordination compound. The metal coordination compound is as described above.

[0388] 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.

[0389] 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.

[0390] <Production Example 1: Synthesis of Compound 1>

[0391]

[0392] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-chloro-15-oxa-7b-aza-15a-bor abenzo[gh]indeno[1,2,3-de]tetraphene (9-chloro-15-oxa-7b-aza-15a-bor abenzo[gh]indeno[1,2,3-de]tetraphene) (2.50 g, 6.62 mmol) and compound a-1 (2.42 g, 7.28 mmol) were completely dissolved in 210 mL of xylene, and sodium tert-butoxide (NaOtBu) (1.27 g, 13.24 mmol) was added, and bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.10 g, 0.20 mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the base was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce Compound 1 (2.23 g, 50%).

[0393] MS[M+H] + =674

[0394] <Production Example 2: Synthesis of Compound 2>

[0395]

[0396] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 5-chloro-15-oxa-7b-aza-15a-bor abenzo[gh]indeno[1,2,3-de]tetraphene (5-chloro-15-oxa-7b-aza-15a-bor abenzo[gh]indeno[1,2,3-de]tetraphene) (2.50 g, 6.62 mmol) and compound a-1 (2.42 g, 7.28 mmol) were completely dissolved in 200 mL of xylene, and sodium tert-butoxide (NaOtBu) (1.27 g, 13.24 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.10 g, 0.20 mmol) and heated with stirring for 5 hours. The temperature was lowered to room temperature, the base was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized with 220 mL of ethyl acetate to produce Compound 2 (2.42 g, 54%).

[0397] MS[M+H] + =674

[0398] <Production Example 3: Synthesis of Compound 3>

[0399]

[0400] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(3-chlorophenyl)-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]tetraphene) (3.25 g, 7.16 mmol) and compound a-2 (1.32 g, 7.88 mmol) were completely dissolved in 230 mL of xylene, and then sodium tert-butoxide (NaOtBu) (1.38 g, 14.33 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.11 g, 0.21 mmol) and heated with stirring for 4 hours. The temperature was lowered to room temperature, the base was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to produce Compound 3 (2.77 g, 66%).

[0401] MS[M+H] + =585

[0402] <Production Example 4: Synthesis of Compound 4>

[0403]

[0404] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 5,9-dichloro-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]tetraphene (3.50 g, 8.50 mmol) and compound a-3 (1.56 g, 9.34 mmol) were completely dissolved in 250 mL of xylene, and then sodium tert-butoxide (NaOtBu) (1.63 g, 16.99 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.13 g, 0.25 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the base was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce Compound 4 (2.79 g, 49%).

[0405] MS[M+H] + =674

[0406] <Production Example 5: Synthesis of Compound 5>

[0407]

[0408] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 15-chloro-9-oxa-5-thia-16b-aza-8b-bora dibenzo[a,k]perylene (2.50 g, 6.10 mmol) and compound a-4 (2.23 g, 6.71 mmol) were completely dissolved in 220 mL of xylene, and sodium tert-butoxide (NaOtBu) (1.17 g, 12.21 mmol) and bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.09 g, 0.18 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to produce compound 5 (2.58 g, 60%).

[0409] MS[M+H] + =706

[0410] <Production Example 6: Synthesis of Compound 6>

[0411]

[0412] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 15-chloro-5,5-dimethyl-5H-9-oxa-16b-aza-8b-boradibenzo[a,k]perylene (15-chloro-5,5-dimethyl-5H-9-ox a-16b-aza-8b-boradibenzo[a,k]perylene) (2.50 g, 5.96 mmol) and compound a-1 (2.18 g, 6.55 mmol) were completely dissolved in 230 mL of xylene, and sodium tert-butoxide (Na OtBu) (1.15 g, 11.92 mmol) was added, followed by addition of bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.09 g, 0.18 mmol) and heating with stirring for 5 hours. The temperature was lowered to room temperature, the base was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce Compound 6 (2.13 g, 50%).

[0413] MS[M+H] + =716

[0414] <Production Example 7: Synthesis of Compound 7>

[0415]

[0416] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 15-(4-chlorophenyl)-5,9-dioxa-16b-aza-8b-boradibenzo[a,k]perylene (15-(4-chlorophenyl)-5,9-dioxa-16b-aza-8b-boradibenzo[a,k]perylene) (2.50 g, 5.32 mmol) and compound a-2 (0.98 g, 5.85 mmol) were completely dissolved in 200 mL of xylene, and then sodium tert-butoxide (NaOtBu) (1.02 g, 10.64 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.08 g, 0.16 mmol) and heated with stirring for 3 hours. The temperature was lowered to room temperature, the base was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized from 220 mL of ethyl acetate to produce Compound 7 (1.92 g, 60%).

[0417] MS[M+H] + =601

[0418] <Production Example 8: Synthesis of Compound 8>

[0419]

[0420] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 15-(2-chlorophenyl)-9-oxa-5-thia-16b-aza-8b-boradibenzo[a,k]perylene (15-(2-chlorophenyl)-9-oxa-5-thia-16b-aza-8b-boradibenzo[a,k]perylene) (2.50 g, 5.14 mmol) and compound a-2 (0.94 g, 5.66 mmol) were completely dissolved in 210 mL of xylene, and then sodium tert-butoxide (NaOtBu) (0.99 g, 10.29 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.08 g, 0.15 mmol) and heated with stirring for 2 hours. The temperature was lowered to room temperature, the base was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized from 210 mL of ethyl acetate to produce Compound 8 (1.88 g, 59%).

[0421] MS[M+H] + =617

[0422] <Production Example 9: Synthesis of Compound 9>

[0423]

[0424] Under nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 9-chloro-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]benzanthracene-1,2,3,4,5,6,7,8,10,11,12,13,14-d13 was added. -1,2,3,4,5,6,7,8,10,11,12,13,14-d13) (2.50 g, 6.40 mmol) and compound a-1 (2.34 g, 7.04 mmol) were completely dissolved in 200 mL of xylene, and sodium tert-butoxide (NaOtBu) (1.23 g, 12.80 mmol) was added, and bis (tri-tert-butylphosphine) palladium (0) (BTP) (0.10 g, 0.19 mmol) was added, and heated with stirring for 3 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure and recrystallized with 220 mL of ethyl acetate to produce compound 9 (2.02 g, 46%).

[0425] MS[M+H] + =687

[0426] <Production Example 10: Synthesis of Compound 10>

[0427]

[0428] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-chloro-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]benzanthracene-1,2,3,4,5,6,7,8,10,11,12,13,14-d13 (2.50 g, 6.40 mmol) and compound a-5 (2.44 g, 7.04 mmol) were completely dissolved in 180 mL of xylene, sodium tert-butoxide (NaOtBu) (1.23 g, 12.80 mmol) was added, bis(tri-tert-butylphosphine)palladium(0) (BTP) (0.10 g, 0.19 mmol) was added, and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to produce compound 10 (1.95 g, 43%).

[0429] MS[M+H] + =702

[0430] <Production Example 11: Synthesis of Compound 11>

[0431]

[0432] Under nitrogen atmosphere, in a 500 mL round-bottom flask, the compound 9-(3-chlorophenyl)-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]benzanthracene-1,2,3,4,5,6,7,8,10,11,12,13,14-d13 was added. traphene-1,2,3,4,5,6,7,8,10,11,12,13,14-d13) (2.50 g, 5.36 mmol) and compound a-5 (2.04 g, 5.89 mmol) were completely dissolved in 220 mL of xylene, and sodium tert-butoxide (NaOtBu) (1.03 g, 10.71 mmol) was added, and bis (tri-tert-butylphosphine) palladium (0) (BTP) (0.08 g, 0.16 mmol) was added, and then heated and stirred for 5 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 11 (2.24 g, 54%).

[0433] MS[M+H] + =778

[0434] <Production Example 12: Synthesis of Compound 12>

[0435]

[0436] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 5-chloro-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]benzanthracene-1,2,3,4,6,7,8,9,10,11,12,13,14-d13 was added.

[0437] (5-chloro-15-oxa-7b-aza-15a-borabenzo[gh]indeno[1,2,3-de]tetraphene-1,2,3,4,6,7,8,9,10,11,12,13,14-d13) (2.50 g, 6.40 mmol) and compound a-6 (2.44 g, 7.04 mmol) were completely dissolved in 230 mL of xylene, and sodium tert-butoxide (NaOtBu) (1.23 g, 12.80 mmol) was added, and bis(tri-tert-butylphosphine)palladium (0) (0.10 g, 0.19 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized from 210 mL of ethyl acetate to produce compound 12 (2.67 g, 59%).

[0438] MS[M+H] + =702

[0439] <Example 1-1>

[0440] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0441] On the ITO transparent electrode prepared as the anode, the following compound HT1 and the following compound HI1 were mixed in a ratio of 98:2 (molar ratio) and The following compound HT1 was vacuum-deposited on the hole injection layer. Then, on the hole transport layer, a film with a thickness of The compound 1BH (p-type) synthesized in the above-mentioned Preparation Example 1 was vacuum-deposited to form an electron blocking layer. Next, on the above-mentioned electron blocking layer, a mixture of the following compound BH (n-type) and the compound 1BH (p-type) synthesized in the above-mentioned Preparation Example 1 at a weight ratio of 1:1 and the following compound BD at a weight ratio of 88:12 were vacuum-deposited to form an electron blocking layer. On the above-mentioned light-emitting layer, a film thickness of The following compound BH (n-type) was vacuum-deposited to form a hole blocking layer. Next, the following compound ET1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A thickness of is evaporated to form a cathode.

[0442]

[0443] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 ~5×10 -6 A support is provided to produce an organic light-emitting device.

[0444] <Example 1-2 to Example 1-12>

[0445] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds manufactured in Manufacturing Examples 1 to 12 were used instead of Compound 1.

[0446] <Comparative Examples 1-1 to 1-5>

[0447] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1. Compounds C1 to C5 used in Table 1 below are as follows.

[0448]

[0449] <Experimental example>

[0450] When current was applied to the organic light-emitting devices manufactured in the above-mentioned Examples and Comparative Examples, voltage, efficiency, color coordinates and lifetime were measured. The results are shown in the following Table 1. 90 It refers to the time required for the brightness to decrease from the initial brightness (1600 nits) to 90%.

[0451]

Table 1

[0452]

[0453] As shown in Table 1 above, R of the core structure of Chemical Formula 1 of the present application is 4 With R 5 (or R 9 With R 10 ) combined with a p-type host in the core structure and further substituted with a carbazole group, the organic light-emitting devices of Examples 1-1 to 1-12 show excellent characteristics in terms of efficiency, driving voltage and stability of the organic light-emitting devices.

[0454] In contrast, the compounds of Comparative Examples 1-1 to 1-4 are structures in which a carbazole group is bonded to a compound to which a substituent of the core structure is not further bonded, and the organic light-emitting devices using the above compounds show results of increased voltage, decreased efficiency and stability (lifespan) compared to the organic light-emitting devices of Examples 1-1 to 1-12 using the compounds according to Chemical Formula 1 of the present application.

[0455] In addition, the compounds of Comparative Examples 1-5 are structures in which the substituents of the core structure are bonded but not substituted with the carbazole group. The organic light-emitting devices using the above compounds show an increase in voltage and a decrease in efficiency and stability (lifespan) compared with the organic light-emitting devices of Examples 1-1 to 1-12 using the compounds according to Chemical Formula 1 of the present application.

Claims

1. An organic compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R1 to R 16 At least one of the following chemical formula 2-1 or chemical formula 2-2, The R1 to R 16 The groups not being the groups of Chemical Formula 2-1 or Chemical Formula 2-2 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or selectively combine with adjacent groups to form a substituted or unsubstituted ring, When the R4 and R5 are bonded to each other, they are connected via the -(X)a- bonding group. The R9 and R 10 When they are bound to each other, they are connected through the -(Y)b-binding group. The X and Y are the same or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R", R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, a and b are each 0 or 1, a+b is 1 or 2, In the chemical formula 2-1 and the chemical formula 2-2, * is the site that binds to the chemical formula 1, L1 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 17 To R 19 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, o is an integer from 1 to 8, p is an integer from 1 to 7, q is an integer from 1 to 8, m is 0 or 1, 1≤m+o≤8, 1≤m+p≤7, When o is 2 or more, 2 or more R 17 Same or different from each other, When p is 2 or more, two or more R 17 Same or different from each other, When q is 2 or more, two or more R 18 The same as or different from each other.

2. The organic compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] In the chemical formulas 1-1 to 1-6, R1 to R3, R6 to R 16 The definitions of R, R' and R" are the same as those in the chemical formula 1.

3. The organic compound according to claim 1, wherein The chemical formula 2-1 is any one of the following chemical formulas 2-1-1 to 2-1-5: [Chemical formula 2-1-5] In the chemical formula 2-1-1 to the chemical formula 2-1-5, the definitions of L1, o and q are the same as those in the chemical formula 2-1. R 17 and R 18 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

4. The organic compound according to claim 1, wherein The chemical formula 2-2 is any one of the following chemical formulas 2-2-1 to 2-2-4: In the chemical formulae 2-2-1 to 2-2-4, the definitions of L1 and p are the same as those in the chemical formula 2-2. R 17 and R 19 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

5. The organic compound according to claim 1, wherein The above-mentioned L1 is an arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

6. The organic compound according to claim 1, wherein R 17 To R 19 are the same as or different from each other and are each independently hydrogen, deuterium, an aryl group having 6 to 30 carbon atoms which may be substituted or not substituted by deuterium, or a heterocyclic group having 2 to 30 carbon atoms which may be substituted or not substituted by deuterium.

7. The organic compound according to claim 1, wherein The deuterium substitution rate of the chemical formula 1 is greater than 30%.

8. The organic compound according to claim 1, wherein The compound of Chemical Formula 1 is any one of the following compounds:

9. An organic light-emitting device, comprising: 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 organic 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 organic compound.

11. The organic light emitting device according to claim 10, wherein: The organic compound is included as a host of the light emitting layer.

12. The organic light emitting device according to claim 10, wherein: The light-emitting layer includes the organic compound as a host of the light-emitting layer and further includes a dopant of the light-emitting layer.

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