Organic compound and organic light-emitting device including same

Abstract

The invention provides a novel organic compound and an organic light-emitting device comprising the same. An organic light emitting device according to an embodiment of the present invention comprises: a first electrode; a second electrode facing the first electrode; and one or more organic material layers located on the inner sides of the first electrode and the second electrode, and at least one of the one or more organic material layers is a hole transport layer or a hole transport auxiliary layer containing the organic compound represented by the chemical formula 1 of the present invention.

Description

Technical Field

[0001] This invention relates to an organic compound and an organic light-emitting device containing the same. Background Technology

[0002] Compared with other flat panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic light-emitting devices (OLEDs) have a simpler structure and offer several advantages in fabrication processes. They also feature high brightness, excellent viewing angle characteristics, fast response speed, and low driving voltage. Therefore, they are being actively developed and commercialized as light sources for flat panel displays such as wall-mounted TVs, backlighting of displays, illumination, and billboards.

[0003] Organic light-emitting devices consist of an organic layer between two electrodes. They operate on the following principle: electrons and holes are injected into the light-emitting layer from the two electrodes, and the electrons and holes combine to generate excitons. When the generated excitons fall from the excited state to the ground state, light is produced.

[0004] Organic light-emitting devices (OLEDs) may include at least one light-emitting layer. Typically, OLEDs with multiple light-emitting layers include multiple light-emitting layers that emit light with different peak wavelengths, thereby enabling the achievement of a specific color through a combination of light with different peak wavelengths.

[0005] Such organic light-emitting devices can be divided into front-emitting diodes (LEDs) and back-emitting diode structures. Front-emitting diodes use a reflective second electrode (Cathode) to emit light generated from the light-emitting layer towards the semi-transparent first electrode (Anode). Conversely, back-emitting diodes use a reflective first electrode to emit light generated from the light-emitting layer towards the transparent second electrode side, which is the direction in which the thin-film transistor is driven, and the light is reflected back to the first electrode.

[0006] Existing technical documents

[0007] Patent documents

[0008] International Patent Publication WO2021-085982A Summary of the Invention

[0009] The problem the invention aims to solve

[0010] The purpose of this invention is to provide a novel organic compound and an organic light-emitting device containing the organic compound.

[0011] In addition to the technical problems mentioned above, embodiments of the present invention can also be used to address other technical problems not specifically addressed.

[0012] The purpose of this invention is not limited to the purposes stated above. Other purposes and advantages of the invention not stated above can be understood through the following description, and will be more clearly understood through the embodiments of the invention.

[0013] Furthermore, it is readily understood that the objectives and advantages of the present invention can be achieved through the means disclosed in the embodiments of the present invention and combinations thereof.

[0014] means for solving problems

[0015] To address the aforementioned technical problem, according to one embodiment of the present invention, an organic compound represented by the following chemical formula 1 can be provided.

[0016] [Chemical Formula 1]

[0017]

[0018] In the chemical formula 1,

[0019] L1 is selected from the group consisting of arylene groups with 6 to 30 free single bonds, substituted or unsubstituted carbon atoms, and heteroarylene groups with 1 to 30 substituted or unsubstituted carbon atoms.

[0020] Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms.

[0021] If L1 exists, then, based on L1, the Ar1 and the nitrogen atom (N) are in either ortho or meta positions relative to each other.

[0022] R1 to R 24 They may be the same as or different from each other, and each is independently selected from the group consisting of hydrogen, deuterium, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, and heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms.

[0023] When L1, Ar1, Ar2 and R1 to R 24When substituted, the substituents may be the same or different from each other, and may each be independently selected from one or more of the group consisting of deuterium, cyano, nitro, halogen, hydroxyl, alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 30 carbon atoms, heteroaryl with 1 to 30 carbon atoms, alkylamino with 1 to 10 carbon atoms, arylamino with 6 to 30 carbon atoms, heteroarylamino with 1 to 30 carbon atoms, alkylsilyl with 1 to 10 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 10 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 10 carbon atoms, and arylthio with 6 to 30 carbon atoms. When there are multiple substituents, the substituents may be the same or different from each other, and may bond with adjacent groups to form substituted or unsubstituted rings.

[0024] *a indicates the bonding position on the phenylene oxide, R7 to R8. 11 One in the value represents a single bond that bonds with *a.

[0025] According to another embodiment of the present invention, an organic light-emitting device is provided, the organic light-emitting device comprising: a first electrode; a second electrode opposite to the first electrode; and one or more organic layers located inside the first electrode and the second electrode, wherein at least one of the more than one organic layers is a hole transport layer or a hole transport auxiliary layer comprising an organic compound represented by the chemical formula 1.

[0026] Invention Effects

[0027] The organic compound represented by chemical formula 1 of the present invention can achieve excellent hole transport characteristics.

[0028] Furthermore, the organic light-emitting device of the present invention includes a hole transport layer and / or a hole transport auxiliary layer, wherein the hole transport layer and / or the hole transport auxiliary layer contains an organic compound represented by chemical formula 1 of the present invention, which can improve the driving voltage, efficiency and lifetime characteristics of the organic light-emitting device.

[0029] Furthermore, when the organic compound represented by Chemical Formula 1 of the present invention is used as a hole transport auxiliary layer material, it can have a suitable energy level as a hole transport auxiliary layer, the function of which is to transport holes from the hole transport layer to the light-emitting layer and block electrons from the light-emitting layer.

[0030] Furthermore, the organic light-emitting device of the present invention includes a hole transport layer and / or a hole transport auxiliary layer, wherein the hole transport layer and / or the hole transport auxiliary layer contains an organic compound represented by chemical formula 1 of the present invention, which can excellently achieve the target color coordinates of the light-emitting layer even when combined with a light-emitting layer of any color.

[0031] The effects of this specification are not limited to those mentioned above. Those skilled in the art to which this invention pertains can clearly understand other effects not mentioned from the following description. Detailed Implementation

[0032] The above-mentioned objectives, features, and advantages are described in detail below, thereby enabling those skilled in the art to readily implement the technical concept of this invention.

[0033] When describing this invention, detailed descriptions of well-known technologies related to this invention may be omitted if it is determined that such detailed descriptions may unnecessarily obscure the essence of the invention.

[0034] When the terms "including," "having," "constituting," "equipped with," or "possessing" are used in this specification, other parts may be added unless "~only" is used. Unless specifically and explicitly stated, when a constituent element is expressed in the singular, the plural case is included.

[0035] In this specification, when explaining the constituent elements, it is to be understood that the range of error is included, unless otherwise clearly stated.

[0036] In this specification, the provision of any configuration on the "upper (or lower)" or "upper (or lower)" of a constituent element can refer not only to the case where the configuration is provided in contact with the upper (or lower) surface of the constituent element, but also to the case where other configurations can be interposed between the constituent element and the configuration provided on (or below) the constituent element.

[0037] The term "halogen group" as used in this specification includes fluorine, chlorine, bromine, and iodine.

[0038] As used in this specification, the term "alkyl" refers to both straight-chain and branched alkyl groups. Unless otherwise specified, an alkyl group comprises 1 to 10 carbon atoms and may include, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, etc. Furthermore, alkyl groups may be substituted in any way.

[0039] As used in this specification, the term "cycloalkyl" refers to a cyclic alkyl group. Unless otherwise specified, a cycloalkyl group comprises 3 to 10 carbon atoms and may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc. Furthermore, cycloalkyl groups may be substituted in any way.

[0040] As used in this specification, the term "alkenyl" refers to a straight-chain alkenyl or branched alkenyl having at least one carbon-carbon double bond. Unless otherwise specified, an alkenyl comprises 2 to 30 carbon atoms and includes, but is not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc. Furthermore, alkenyl groups may be substituted in any way.

[0041] As used in this specification, the term "cycloalkenyl" refers to a cyclic alkenyl group. Unless otherwise specified, a cycloalkenyl group contains 3 to 20 carbon atoms, and the cycloalkenyl group may be substituted in any way.

[0042] As used in this specification, the term "alkynyl" refers to straight-chain and branched alkynes having at least one carbon-carbon triple bond. Unless otherwise specified, an alkynyl group comprises 2 to 30 carbon atoms and may include, but is not limited to, ethynyl, 2-propynyl, etc. Furthermore, the alkynyl group may be substituted in any way.

[0043] As used in this specification, the term "cycloynyl" refers to a cyclic ynyl group. Unless otherwise specified, a cycloynyl group contains 3 to 20 carbon atoms, and the cycloynyl group may be substituted in any way.

[0044] The terms “arylalkyl” or “aralkyl” used in this specification are used interchangeably and refer to an alkyl group having an aromatic group as a substituent. In addition, arylalkyl (aralkyl) may be substituted in any way.

[0045] The terms "aryl" or "aromatic group" used in this specification have the same meaning, and aryl groups include monocyclic and fused-ring groups. Fused rings can include "fused rings" consisting of two or more rings (two adjacent rings sharing two carbon atoms). Furthermore, they can also include forms where two or more rings are simply attached or fused together. Unless otherwise specified, aryl groups contain 6 to 30 carbon atoms and may include, but are not limited to, phenyl, naphthyl, anthraceneyl, phenanthryl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, etc. Additionally, aryl groups may be substituted in any way.

[0046] The terms "heteroaryl" or "heteroaromatic group" as used in this specification have the same meaning. Heteroaryl groups include monocyclic groups and fused-ring groups. Fused rings can include "fused rings," which are two or more rings sharing two carbon atoms or heteroatoms. Additionally, they can include forms of two or more rings simply attached or condensed together. Unless otherwise specified, heteroaryl groups can have 1 to 30 carbon atoms, and when there are 1 or 2 carbon atoms, rings can be formed by including additional heteroatoms. Furthermore, heteroaryl groups can contain 1 to 30 carbon atoms, in which case one or more carbon atoms in the ring are replaced by heteroatoms such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se), and can include, but are not limited to, six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathiyl, indoleazinyl, indoleyl, purine, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, phenylcarbazole, 9-phenylcarbazole, and carbazole; and 2-furanyl, N-imidazolyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl. In addition, heteroaryl groups can be arbitrarily substituted.

[0047] As used in this specification, the term "heterocyclic group" means that at least one carbon atom in the carbon atoms constituting aryl, cycloalkyl, cycloalkenyl, cycloynyl, aralkyl, arylamino, etc., is replaced by a heteroatom such as oxygen (O), nitrogen (N), sulfur (S) or selenium (Se). Referring to the above definition, it may include heteroaryl, heterocycloalkyl, heterocycloalkenyl, heterocycloynyl, heteroarylalkyl, heteroarylamino, etc. In addition, heterocyclic groups may be arbitrarily substituted.

[0048] The term "carbon ring" as used in this specification may be used as a term that includes "cycloalkyl" as an alicyclic group and "aryl (aromatic group)" as an aromatic group, unless otherwise specified.

[0049] As used in this specification, the terms "heteroalkyl" and "heteroaryl" mean that at least one carbon atom in the alkyl and aryl groups is replaced by a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), or selenium (Se). In addition, heteroalkyl and heteroaryl groups may be substituted in any way.

[0050] As used in this specification, the terms "alkylamino", "aralkylamino", "arylamino", and "heteroarylamino" refer to amino groups (or amine groups) that are substituted by the alkyl, aralkyl, aryl, or heteroaryl groups, and include primary, secondary, and tertiary amino groups (or amine groups). In addition, alkylamino, arylalkylamino, arylamino, and heteroarylamino groups may be substituted in any way.

[0051] The terms “alkylsilyl”, “arylsilyl”, “alkoxy”, “aryloxy”, “alkylthio”, and “arylthio” used in this specification refer to alkylsilyl, oxy, and thio groups in which the alkyl and aryl groups are respectively substituted. In addition, alkylsilyl, arylsilyl, alkoxy, aryloxy, alkylthio, and arylthio can be arbitrarily substituted.

[0052] As used in this specification, the terms "arylene," "arylalkylene," "heteroarylene," and "heteroarylalkylene" mean that each of the aryl, aralkyl, heteroaryl, and heteroaryl groups is a divalent substituent that further includes one substituted component. Furthermore, the arylene, arylalkylene, heteroaryl, and heteroarylalkylene groups may be substituted in any way.

[0053] As used in this specification, the term "substitution" means that the hydrogen (H) atoms bonded to the carbon atoms, carbon atoms, etc., of the compounds of the present invention are replaced by substituents other than hydrogen. When multiple substituents are present, the substituents may be the same or different.

[0054] The substituents may be independently selected from the group consisting of deuterium, cyano, nitro, halogen, hydroxyl, alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 30 carbon atoms, heteroaryl with 1 to 30 carbon atoms, alkylamino with 1 to 10 carbon atoms, arylamino with 6 to 30 carbon atoms, heteroarylamino with 1 to 30 carbon atoms, alkylsilyl with 1 to 10 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkoxy with 1 to 10 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkylthio with 1 to 10 carbon atoms, and arylthio with 6 to 30 carbon atoms.

[0055] The units used in this specification are based on weight (wt) unless otherwise stated. For example, when stated as "%", it is interpreted as weight % (wt%).

[0056] The organic compounds and organic light-emitting devices comprising the organic compounds according to the present invention are described in detail below.

[0057] According to one embodiment of the present invention, in chemical formula 1, L1 can be a single-bonded or substituted or unsubstituted aryl group having 6 to 15 carbon atoms. As an example, L1 can be a single-bonded or substituted or unsubstituted phenylene group.

[0058] In Formula 1, Ar1 can be an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms containing at least one heteroatom selected from the group consisting of O, S, and N. As an example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted carbazole, a substituted or unsubstituted 9-phenylcarbazole, a substituted or unsubstituted dimethylfluorenyl, or a substituted or unsubstituted diphenylfluorenyl.

[0059] Ar2 can be a substituted or unsubstituted aryl group having 6 to 15 carbon atoms. As an example, the Ar2 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted phenanthryl.

[0060] L1, Ar1, Ar2 and R1 to R 24 The substituents may be the same or different from each other, and each is independently selected from one or more of the group consisting of deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, phenyl-naphthyl, anthracene, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazole, phenylcarbazole and 9-phenylcarbazole.

[0061] According to one embodiment of the present invention, in Formula 1, with L1 as the reference, Ar1 and nitrogen atom (N) are in the ortho or meta position relative to each other.

[0062] According to one embodiment of the present invention, in chemical formula 1, Ar2 can be one of the following chemical formulas 2 to 5.

[0063]

[0064] In chemical formulas 2 to 5, the R 25 To R 28 They may be the same as or different from each other, and each is independently selected from the group consisting of hydrogen, deuterium, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, and heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms.

[0065] o is an integer from 1 to 5.

[0066] p is an integer from 1 to 7.

[0067] q is an integer from 1 to 7.

[0068] r is an integer from 1 to 9.

[0069] * indicates the location of the bond.

[0070] According to one embodiment of the present invention, when chemical formula 2 is selected as Ar2, Ar1 can be an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms containing at least one heteroatom selected from the group consisting of O, S, and N. As an example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted carbazole, a substituted or unsubstituted 9-phenylcarbazole, or a substituted or unsubstituted diphenylfluorenyl.

[0071] According to one embodiment of the present invention, when chemical formula 3 or chemical formula 4 is selected as Ar2, Ar1 can be an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms containing at least one heteroatom selected from O and S. As an example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dimethylfluorenyl, or a substituted or unsubstituted diphenylfluorenyl.

[0072] According to one embodiment of the present invention, when chemical formula 5 is selected as Ar2, Ar1 can be an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms containing at least one heteroatom selected from the group consisting of O, S, and N. As an example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted carbazole, a substituted or unsubstituted 9-phenylcarbazole, a substituted or unsubstituted dimethylfluorenyl, or a substituted or unsubstituted diphenylfluorenyl.

[0073] According to one embodiment of the present invention, the chemical formula 1 may be represented by the following chemical formula 6 or chemical formula 7.

[0074] [Chemical Formula 6]

[0075]

[0076] L1, Ar1, Ar2, R1 to R 24 The definitions of Ar1 and its substituents are the same as those described in Formula 1. Ar1 can be one of the following Formulas 8 to 11.

[0077] In the chemical formulas 8 to 11, R 29 To R 32 They may be the same as or different from each other, and each is independently selected from the group consisting of hydrogen, deuterium, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, and heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms.

[0078] s is an integer from 1 to 5, t and v are integers from 1 to 7, and u is an integer from 1 to 9.

[0079] In the chemical formula 11, X can be O, S, or NR. 33 or CR 34 R 35 One of them. According to an embodiment of the present invention, when chemical formula 2 or chemical formula 5 is selected as Ar2, X can be O, S, or CR. 34 R 35 NR 33 According to one embodiment of the present invention, when chemical formula 3 or chemical formula 4 is selected as Ar2, X can be O, S, or CR. 34 R 35 .

[0080] According to one embodiment of the present invention, when chemical formula 5 is selected as Ar2, X can be O, S, or NR. 33 CR 34 R 35 .

[0081] The R 33 To R 35 They may be identical or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 1 to 30 carbon atoms. In this case, when chemical formula 2 is selected as Ar2, R 34 and R 35 They may be the same or different from each other, and may each be an aryl group with 6 to 30 substituted or unsubstituted carbon atoms or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms.

[0082] * indicates the location of the bond.

[0083] According to one embodiment of the present invention, R1 to R 25 They may be the same or different from each other, and can be hydrogen or deuterium independently.

[0084] According to one embodiment of the present invention, L1 can be a single bond or one of the substituents represented by F1 or F2 below. The dashed lines in the following structures indicate connection sites with different substituents. Dn refers to the number of deuterium substituted in the following F1 and F2 structures, where n, representing the number of deuterium, is an integer greater than or equal to 0, with the upper limit being the number of substituted hydrogen atoms in the structure. For example, when n is 0 in F1, it means... (denoted as D0), when n is 1, it means that one of the four hydrogen atoms of the phenyl group is replaced by deuterium. (Referred to as D1).

[0085]

[0086] According to one embodiment of the present invention, Ar1 may be an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted carbon atoms.

[0087] According to one embodiment of the present invention, Ar1 may be an aryl group with 6 to 30, 6 to 25, 6 to 15, 6 to 12 or 6 to 10 substituted or unsubstituted carbon atoms, or a heteroaryl group with 3 to 30, 3 to 18 or 3 to 12 substituted or unsubstituted carbon atoms.

[0088] According to one embodiment of the present invention, Ar1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted tertiary phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraxyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted diphenylfluorenyl, a substituted or unsubstituted naphthyl-phenyl, a substituted or unsubstituted phenanthyl-phenyl, a substituted or unsubstituted naphthyl-biphenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl-phenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted 9-phenylcarbazole, a substituted or unsubstituted dibenzofuranyl-phenyl, a substituted or unsubstituted dibenzothiophenyl-phenyl, a substituted or unsubstituted carbazole-phenyl, or a substituted or unsubstituted 9-phenylcarbazole-phenyl. For example, Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted diphenylfluorenyl, a substituted or unsubstituted naphthyl-phenyl, a substituted or unsubstituted phenanthryl-phenyl, or a substituted or unsubstituted naphthyl-biphenyl.

[0089] Alternatively, Ar1 can be a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthyl, a deuterated or unsubstituted fluorenyl, a deuterated or unsubstituted diphenylfluorenyl, a deuterated or unsubstituted naphthyl-phenyl, a deuterated or unsubstituted phenanthyl-phenyl, or a deuterated or unsubstituted naphthyl-biphenyl.

[0090] According to one embodiment of the present invention, Ar1 may be one of the substituents represented by M1 to M52 below.

[0091] In the following M1 to M52 structures, * indicates the bonding position, and Dn refers to the number of deuterium substituted in the structures M1 to M52. Here, n, representing the number of deuterium substituted ions, is an integer greater than or equal to 0, with the upper limit being the number of hydrogen atoms that can be substituted in that structure. For example, when n is 0 in M1, it means... When n is 1, it means that one of the five hydrogen atoms of the phenyl group is replaced by deuterium.

[0092]

[0093]

[0094] According to one embodiment of the present invention, when an aromatic amino group is bonded to the 1st or 8th position of a dibenzofuran represented by the following chemical formula A and Ar2 (chemical formula 2) is bonded to the 4th or 5th position, the compound of the present invention may have a more suitable energy level as a hole transport auxiliary layer, which functions to transport holes from the hole transport layer to the light-emitting layer and block electrons from the light-emitting layer.

[0095] [Chemical Formula A]

[0096]

[0097] According to one embodiment of the present invention, in the compound of the present invention, when Ar2 is of chemical formula 2, based on L1, Ar1 and nitrogen atoms (N) can be connected to each other in a meta or ortho manner, and compared with the single bond structure, the planarity of the L1 structure is increased, resulting in better thermal stability. Furthermore, due to its higher T1 energy level than the para form, energy transfer is better achieved, thereby improving device efficiency. For example, when Ar2 is of chemical formula 2, based on L1, when Ar1 and nitrogen atoms (N) are in a meta position, a larger steric hindrance is generated, which has the effect of reducing the crystallinity of the thin film, thereby further improving the performance of the organic light-emitting device.

[0098] According to one embodiment of the present invention, the compound of the present invention comprises a structure represented by the following chemical formula B or chemical formula C, where * indicates the bonding position between the dibenzofuran of chemical formula 1 and the nitrogen (N) substituted by L1. When chemical formula C is used, it can exhibit superior device performance.

[0099]

[0100] According to one embodiment of the present invention, when Ar2 is of chemical formula 2 and Ar1 is an aryl group with 6 to 30, 6 to 25, 6 to 15, 6 to 12 or 6 to 10 substituted or unsubstituted carbon atoms, the compound of the present invention can have high thermal stability because it does not contain heteroatoms, thereby achieving better device performance.

[0101] According to one embodiment of the present invention, when Ar2 is of chemical formula 2, the compound of the present invention comprises a structure of chemical formula C, and based on L1, when Ar1 and nitrogen atom (N) are in meta position and Ar1 is an aryl group with 6 to 10 substituted or unsubstituted carbon atoms, it can exhibit characteristics of low voltage, long lifetime and high efficiency.

[0102] According to one embodiment of the present invention, the compound represented by chemical formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] An organic light-emitting device according to an embodiment of the present invention includes a first electrode (anode) and a second electrode (cathode) opposite to the first electrode, and may include one or more organic layers located between the first electrode and the second electrode.

[0137] At least one of the more than one organic layers may contain an organic compound represented by chemical formula 1.

[0138] The organic layer may include at least one of the following: a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, an emitting layer (EML), an electron transport auxiliary layer, an electron transport layer (ETL), and an electron injection layer (EIL).

[0139] For example, an organic light-emitting device may have a structure in which a first electrode, a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, an emissive layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a second electrode are stacked sequentially.

[0140] In addition, the organic light-emitting device may have a structure in which a first electrode, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer (EML), an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a second electrode are stacked in sequence.

[0141] In one embodiment of the present invention, the organic layer comprising a compound represented by chemical formula 1 can be a hole transport layer (HTL) or a hole transport auxiliary layer.

[0142] The organic layer or more may further include at least one selected from the group consisting of a hole injection layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

[0143] For example, when an organic compound represented by chemical formula 1 is used as a hole transport auxiliary layer material, it can have a suitable energy level as a hole transport auxiliary layer, which plays the role of transporting holes from the hole transport layer to the light-emitting layer and blocking electrons from the light-emitting layer.

[0144] In an organic light-emitting device according to an embodiment of the present invention, the hole transport layer and / or hole transport auxiliary layer comprising the organic compound represented by Chemical Formula 1 can achieve the target color coordinates excellently even when combined with a light-emitting layer of any color.

[0145] The first electrode can be an anode, and the first electrode can include transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO).

[0146] The second electrode can be a cathode, and it can include materials such as lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). Furthermore, in the case of the aforementioned organic light-emitting devices, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent second electrode that allows light to pass through.

[0147] A capping layer (CPL) can be formed on the surface of the second electrode using a composition for forming the capping layer.

[0148] In addition, a protective film (encapsulation layer or protecting layer) can be applied to the cover layer to protect the organic light-emitting device from moisture and oxygen. These protective films can be formed from a curable adhesive composition containing an inorganic hygroscopic agent.

[0149] The hole injection layer or hole transport layer compound is not particularly limited; any compound may be used as a commonly used hole injection layer or hole transport layer compound. Non-limiting examples of hole injection layer or hole transport layer compounds may include phthalocyanine derivatives, porphyrin derivatives, triarylamine derivatives, indolecarbazole derivatives, etc. For example, it may include 1,4,5,8,9,11-hexaazatriphenylhexanitrile (HAT-CN), copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), N4,N4,N4',N4'-tetra([1,1'-bi [N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-bis(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB), N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0150] The compounds contained in the luminescent layer are not specifically restricted; any compound can be used as long as it is commonly used as the luminescent layer compound. A standalone luminescent compound or a host luminescent compound can be used.

[0151] The luminescent compound serving as the luminescent layer may include, but is not limited to, compounds that induce luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence (TADF, also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes. The luminescent compound may be selected from a variety of materials depending on the desired emission color. Non-limiting examples of luminescent compounds include phenanthrene, anthracene, pyrene, tetraphenylene, pentaphenylene, perylene, naphthylpyrene, dibenzopyrene, rubrogene, and... Isocyclic ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, diazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bis(styrene) derivatives, bis(styrene)aryl derivatives, diazaindane derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives, dibenzofuran derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethystylene derivatives, anthocyanine derivatives, oxanthene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, quinolone derivatives, acridine derivatives, oxazine derivatives, phenylene ethers. Derivatives of oxides, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanpyridine derivatives, 1,2,5-thiadiazolpyrene derivatives, pyrromethene derivatives, pyrene derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridineone derivatives, deazaflavin derivatives, fluorene derivatives, benzo[a]fluorene derivatives, aromatic boron derivatives, aromatic nitrogen-boron derivatives, and metal complexes (complexes of metals such as Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu with heterocyclic ligands, etc.).Examples include N1,N1,N6,N6-tetrakis(4-(1-methylyl)phenyl)pyrene-1,6-diamine, 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-borona[3,2,1-de]anthracene (t-DABNA-dtB), platinum octaethylporphyrin (PtOEP), and Ir(ppy 3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), fac-tris(2-(3-p-xylyl)phenyl)pyridineiridium(III)(fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(III)), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(BT)2(acac), Ir(DMP)3, Ir(M phq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, FIrpic, etc.

[0152] As the host compound for the luminescent layer, a luminescent host, a hole transport host, and an electron transport host, or a combination thereof, can be used. Non-limiting examples of luminescent host compounds include fused-ring derivatives such as anthracene or pyrene, bis(styrene) derivatives such as bis(styrene)-anthracene derivatives or styrenebenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, N-phenylcarbazole (9-phenylcarbazole) derivatives, carbazole nitrile derivatives, etc. Non-limiting examples of hole transport host substances include carbazole derivatives, dibenzofuran derivatives, diphenylthiophene derivatives, triarylamine derivatives, indole-carbazole derivatives, and benzo[a]oxazinofenoxazine derivatives. Non-limiting examples of electron transport host substances include pyridine derivatives, triazine derivatives, phosphine oxide derivatives, benzo[a]furan-pyridine derivatives, and dibenzo[a]oxazinol derivatives. Examples include 9,10-bis(2-naphthyl)anthracene (ADN), tris(8-hydroxyquinoline)aluminum (Alq3), BAlq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-bistyryl)-1,1'-biphenyl) series, spiro-DPVBi (spiro-4,4'-bis(2,2-bistyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl)-phenol lithium salt), bis(bistyryl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole, and metal complexes of oxazole, etc.

[0153] The electron injection layer or electron transport layer compound is not specifically limited; generally, any compound can be used as long as it is used as an electron injection layer or electron transport layer compound. Non-limiting examples of electron injection layer or electron transport layer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, pyrene derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, dibenzoquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, diazole derivatives, metal complexes of oxin derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzopyrrole compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazine derivatives, and benzoquinone derivatives. Imidazolidine derivatives, borane derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives, naphthidine derivatives, aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bis(styrene) derivatives, quinolinol metal complexes, hydroxyazole metal complexes, azomethine metal complexes, tropolone metal complexes, flavonol metal complexes, benzylquinoline metal complexes, and metal salts, etc. These materials can be used alone or in combination with other materials. For example, it may include substances such as 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzyl[d]imidazole, tris(8-hydroxyquinoline)aluminum (Alq3), LiF, Liq, Li2O, BaO, NaCl, CsF, etc.

[0154] The electron transport auxiliary layer compound located between the electron transport layer and the luminescent layer is not specifically limited; any compound can be used as long as it is commonly used as an electron transport auxiliary layer compound. For example, the electron transport auxiliary layer may include pyrimidine derivatives, etc.

[0155] An embodiment of the organic light-emitting device of the present invention can be a front-emitting device or a back-emitting device.

[0156] An embodiment of the organic light-emitting device of the present invention can be used in a display device.

[0157] The organic light-emitting device of one embodiment of the present invention can be applied to transparent display devices, mobile display devices, flexible display devices, etc., but is not limited thereto.

[0158] An embodiment of the organic light-emitting device of the present invention may include a tandem structure, the tandem structure including multiple light-emitting stacks between an anode and a cathode.

[0159] The following are representative examples illustrating the methods for synthesizing the compounds. However, the methods for synthesizing the compounds of the present invention are not limited to the methods illustrated below, or the embodiments of the present invention are not limited to the following examples and experimental cases.

[0160] [Synthesis example]

[0161] Examples of the synthesis of representative compounds 1-2 (P1) are described. Compounds represented by chemical formula 1 of the present invention can be synthesized in a similar manner to the reaction of compounds 1-2 (P1).

[0162] In the following reaction formulas, the solvent, catalyst, protecting group, leaving group, reaction temperature, reaction time, and stoichiometry of reactants are representative examples, and equivalent solvents, catalysts, protecting groups, leaving groups, reaction temperatures, reaction times, and stoichiometry of reactants can be used.

[0163] [Reaction Formula 1]

[0164]

[0165] Under a nitrogen atmosphere, reactant 1 (33.29 mmol), reactant 2 (32.64 mmol), t-BuONa (65.28 mmol), Pd2(dba)3 (0.49 mmol), Sphos (0.98 mmol), and toluene were added to a reaction flask and stirred under reflux. After the reaction was complete, the organic layer was extracted with toluene and water. The extracted solution was treated with MgSO4 to remove residual water, concentrated under reduced pressure, purified by column chromatography, and then recrystallized to obtain the product of P1. The synthesis results of the product of P1 are shown in Table 1 below.

[0166] Table 1

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] [Experimental Example 1] Measurement of HOMO and LUMO

[0178] The effects of the compounds of the present invention were confirmed through the following experiments, and these are only representative examples, and the experimental examples are not limited thereto.

[0179] Experiment Example 1: Simulation Results of Hole Transport Auxiliary Layer

[0180] The role of the hole transport auxiliary layer is to reduce the number of holes accumulated at the interface of the emissive layer due to the HOMO energy difference between the hole transport layer and the emissive layer. Therefore, it is preferable that the HOMO energy difference between the hole transport layer and the emissive layer is smaller than that between the hole transport layer and the emissive layer. Furthermore, to minimize electron leakage from the emissive layer to the hole transport layer, it needs to have a LUMO energy level higher than that of the emissive layer.

[0181] To confirm whether the compound represented by chemical formula 1 of the present invention is suitable as a hole transport auxiliary layer material, the HOMO level (eV) and LUMO level (eV) were calculated using Spartan software (B3LYP DFT 6-31G*by spartan'16) and are shown in Table 2 below.

[0182] Table 2

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] [Experimental Example 2] Determination of T1

[0189] The effects of the compounds of the present invention were confirmed by the following experiments, which are only typical examples and the experimental examples are not limited thereto.

[0190] Experiment Example 2: Quantum Computing

[0191] Quantum computing experiments were performed on compounds 1-99, 1-25, 1-111, 1-100, 1-101, 1-112, 1-113 of the present invention, and comparative example compounds B, C, D, and E described below, and the lowest triplet energy (E[T1]) values ​​are shown in Table 3 below.

[0192] Quantum computing uses B3LYP / 6-31G*(TD-DFT) Gaussian 16W.

[0193] Table 3

[0194]

[0195] [Example 1] Fabrication of an organic light-emitting device (blue light-emitting layer)

[0196] By using a photo-lithography process, the substrate with the first electrode (anode) of the organic light-emitting device, ITO (100nm), is divided into regions of the second electrode (cathode) and the first electrode (anode), as well as an insulating layer, and patterning is formed. Then, with the aim of increasing the work function of the first electrode (ITO) and cleaning it, UV-ozone treatment and surface treatment using O2:N2 plasma are performed.

[0197] Next, on the anode, a hole implantation layer (HIL) is deposited by mixing a mixture of NDP-9 (2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene) (NDP-9(2-(7-Dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile) and N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) in a ratio of 3:97, forming a thickness of 10 nm. Next, on top of the hole injection layer, as a hole transport layer, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) was vacuum deposited to form a thickness of 100 nm. On top of the hole transport layer (HTL), as a hole transport auxiliary layer, compound 1-99 was formed to form a thickness of 15 nm.

[0198] In the upper part of the hole transport auxiliary layer, 9,10-bis(2-naphthyl)anthracene (ADN) is used as the main component and 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-borona[3,2,1-de]anthracene (2,12-Di-tert-butyl) is used as a dopant. A blue luminescent layer was deposited at 25 nm using t-butyl-5,9-bis(4-(tert-butyl)phenyl)-7-(3,5-di-tert-butylphenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene,t-DABNA-dtB), with a host-to-dopant mixing ratio (by weight) of 97:3. On the blue luminescent layer, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (2-(4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole) and Liq were mixed at a weight ratio of 1:1 and deposited at 25 nm. Above the electron transport layer (ETL), an electron injection layer (Liq) of 1 nm is deposited. At the cathode, a mixture of magnesium and silver in a 1:4 weight ratio is deposited to a thickness of 16 nm. On the cathode, as a capping layer, N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) is deposited to a thickness of 60 nm. On the capping layer, a seal cap containing a desiccant is bonded using a UV-curable adhesive to form a protective film (encapsulation layer or protecting layer) to protect the organic light-emitting device from atmospheric oxygen or moisture, thus fabricating the organic light-emitting device.

[0199] [Examples 2 to 24]

[0200] Except for changing the material of compounds 1-99, which were used as the hole transport auxiliary layer material in Example 1, to the materials listed in Table 4 below, the organic light-emitting devices of Examples 2 to 24 were manufactured in the same manner as in Example 1.

[0201] [Comparative Examples 1 to 7]

[0202] Organic light-emitting devices of Comparative Examples 1 to 7 were manufactured using the same method as in Example 1, except that the materials of compounds 1-99 used as hole transport auxiliary layer materials in Example 1 were changed to the following compounds A, B, C, D, E, F, and G.

[0203] [Experimental Example 3] Performance Evaluation of Organic Light-Emitting Devices (Blue Device)

[0204] For each organic light-emitting device manufactured in Examples 1 to 24 and Comparative Examples 1 to 7, an application of 10 mA / cm² was performed using a CS-2000 from Konica Minolta, Japan. 2 Current was used to determine the driving voltage (V) and external quantum efficiency (EQE) (%). Furthermore, a McScience M6000 was used at 10 mA / cm². 2 Driven by a constant current, the time it took for the brightness to decrease from the initial brightness level to 95% was confirmed, and the lifetime (LT95) (hrs) was determined by this method. The measurement results are shown in Table 4 below.

[0205] [Table 4]

[0206]

[0207]

[0208]

[0209] As shown in Table 4, the organic compound represented by Formula 1 of the present invention is characterized in that when Ar1 linked to the phenylene is bonded to a tertiary amine, it is bonded in a meta or ortho position. It has been confirmed that this compound produces greater steric hindrance compared to the comparative compound, thus having the effect of reducing the crystallinity of the film, thereby exhibiting the characteristics of low voltage, high efficiency and long lifetime.

[0210] The embodiments of this specification have been described in more detail above, but this specification is not necessarily limited to these embodiments, and various modifications can be made without departing from the technical concept of this specification.

[0211] Therefore, the embodiments disclosed in this specification are not intended to limit the technical concept of this specification, but are intended to illustrate that the scope of the technical concept of this specification is not limited to these embodiments. Consequently, it should be understood that all aspects of the above embodiments are exemplary and not restrictive.

Claims

1. An organic compound, characterized by, represented by the following formula 1, [Formula 1] In the formula 1, L1is selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, Ar1is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, the Ar1and the nitrogen atom are in the ortho position or the meta position with respect to the L1, Ar2is the following formula 2, [Formula 2] R1to R 25 each independently is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 1 to 30, o is an integer of 1 to 5, when L1, Ar1, Ar2, and R1to R 25 when substituted, the substituents are the same as or different from each other, and each independently one or more selected from the group consisting of deuterium, a cyano group, a nitro group, a halogen group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 1 to 30 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a heteroarylamino group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and an arylthio group having 6 to 30 carbon atoms, when the substituents are a plurality, the substituents are the same as or different from each other, * a denotes the position of bonding on the phenylene group, R7to R 11 one of R7to R9denotes a single bond to *a.

2. The organic compound according to claim 1, wherein the L1is a substituted or unsubstituted phenylene group.

3. The organic compound according to claim 1, wherein the L1is selected from the group consisting of a substituent represented by the following F1or F2, the Dndenotes the number of deuteriums substituted in the structure of the F1and F2.

4. The organic compound according to claim 1, wherein the formula 1 is selected from the group consisting of a compound represented by the following formula 6 or formula 7, [Formula 6] [Formula 7] In the formula 6 or formula 7, L1, Ar1, Ar2, R1to R 24 and the definitions of substituents thereof are the same as described in the Chemical Formula 1.

5. The organic compound according to claim 1, wherein the Ar1is selected from the group consisting of a compound represented by the following formula 8 to formula 11, [Formula 8] [Formula 9] [Formula 10] [Formula 11] In the formula 8 to formula 11, R 29 to R 32 each independently of one another, is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted aryl group with a carbon atom number of 6 to 30, and a substituted or unsubstituted heteroaryl group with a carbon atom number of 1 to 30, s is an integer of 1 to 5, t is an integer of 1 to 7, v is an integer of 1 to 7, u is an integer of 1 to 9, in the formula 11, Said X is O, S, NR 33 or CR 34 R 35 , R 33 R 35 each independently of one another, is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group with a carbon atom number of 1 to 10, a substituted or unsubstituted aryl group with a carbon atom number of 6 to 30, and a substituted or unsubstituted heteroaryl group with a carbon atom number of 1 to 30, * indicates a bonding position.

6. An organic light emitting device comprising: a first electrode, a second electrode opposed to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, at least one of the one or more organic layers is a hole transport layer or a hole transport auxiliary layer containing the organic compound according to claim 1.

7. A display device comprising the organic light emitting device according to claim 6. ​ ​

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