Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. The compound described in the specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment of the present specification can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifespan characteristics in an organic light-emitting device. In particular, the compound described in the specification can be used as a material for a light-emitting layer. Further, the organic light emitting device has the effects of low driving voltage, high efficiency, and / or long lifespan compared to an existing organic light emitting device.

Description

TECHNICAL FIELD

[0001] This application claims priority to Korean Patent Application No. 10-2024-0051916, filed on April 18, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein.

[0002] The present specification relates to a compound and an organic light emitting device including the same. BACKGROUND

[0003] Generally, an organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using organic substances. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including an anode and a cathode and an organic layer between them. Here, in order to improve efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different substances, respectively, for example, can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when the excitons recombine, light is emitted.

[0004] The performance of the organic light emitting device is greatly affected by the organic material located between the electrodes, and thus there is a continuous demand for development of new materials for high-performance organic light emitting devices. SUMMARY

[0005] Technical Problem

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

[0007] Solution to Problem

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

[0009] [Chemical Formula 1]

[0010]

[0011] In the above Chemical Formula 1,

[0012] X1 to X3 are the same as or different from each other, and each is independently N, CH, or CD, at least one of X1 to X3 is N,

[0013] Ar1 is a substituted or unsubstituted aryl group,

[0014] R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0015] Rb is hydrogen or deuterium,

[0016] p is an integer of 1 to 3, and when p is 2 or more, the two or more of Raare the same as or different from each other,

[0017] q is an integer of 1 to 4, and when q is 2 or more, the two or more of Rb are the same as or different from each other.

[0018] According to another embodiment of the present application, there is provided an organic light emitting device including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers comprising the compound described above.

[0019] Effects of the Invention

[0020] The compound described in the present specification can be used as a material for an organic layer of an organic light emitting device. The compound according to at least one embodiment of the present specification can achieve an increase in efficiency, a lower driving voltage, and / or an increase in lifespan characteristics in an organic light emitting device.

[0021] When the compound described in the present application is used as a material for an emitting layer of an organic light emitting device, by preventing the electrical interaction between the host and the dopant, the LUMO of the host can be lowered. Thus, an organic light emitting device having a low driving voltage, high efficiency, and / or long lifespan characteristics compared to the existing organic light emitting device is provided. BRIEF DESCRIPTION OF DRAWINGS

[0022] Figure 1 and 2 FIG. 1 illustrates an example of an organic light emitting device according to an embodiment of the present specification.

[0023] Explanation of Symbols

[0024] 1: Substrate

[0025] 2: First Electrode

[0026] 3: Hole Injection Layer

[0027] 4: Hole Transport Layer

[0028] 5: Electron Blocking Layer

[0029] 6: Emitting Layer

[0030] 7: Hole Blocking Layer

[0031] 8: electron injection and transport layer

[0032] 9: second electrode DETAILED DESCRIPTION

[0033] Hereinafter, the present specification will be described in more detail.

[0034] In the present specification, when a certain part is referred to as "including / including" a certain component, unless otherwise specifically noted, it means that another component can be further included, rather than excluding another component.

[0035] In the present specification, when a certain member is referred to as being "on" another member, it not only includes the case where the certain member is directly on the other member, but also includes the case where another member is interposed therebetween.

[0036] In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital function (highest occupied molecular orbital) in which an electron is located in the highest energy region in a region that can participate in bonding, LUMO (lowest unoccupied molecular orbital) means a molecular orbital function (lowest unoccupied molecular orbital) in which an electron is located in the lowest energy region in a region that does not participate in bonding, and HOMO level means a distance from a vacuum level to HOMO. In addition, LUMO level means a distance from a vacuum level to LUMO.

[0037] In the present specification, band gap means a difference between HOMO and LUMO levels, that is, HOMO-LUMO gap.

[0038] In the present specification, HOMO level can be measured at atmospheric pressure using a photoelectron spectrometer (manufactured by RIKEN KEIKI CO., LTD: AC3), and LUMO level can be calculated using a wavelength value measured by photoluminescence (PL).

[0039] In the present specification, the term "combinations thereof" included in the expression of Markush form means a mixture or combination of one or more selected from the components described in the expression of Markush form, and means including one or more selected from the above components.

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

[0041] The term "substituted" above means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents can be the same or different from each other.

[0042] In the present specification, the term "deuterated" or "substituted with deuterium" means that at least one available hydrogen in each chemical formula is replaced with deuterium. Specifically, in the definition of each chemical formula or substituent, the substitution with deuterium means that at least one or more of the positions in the molecule where hydrogen can be bonded is replaced with deuterium.

[0043] In addition, in the present specification, the term "deuterium substitution rate" or "deuterium incorporation rate" means the percentage of the number of substituted deuterium in each chemical formula with respect to the total number of hydrogen that can exist.

[0044] In one embodiment of the present specification, the term "substituted or unsubstituted" means that one or two or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group an arylthio group , an alkylsulfonyl group an arylsulfonyl group an alkenyl group, a silyl group, a boron group, an amine group, an aryl group, or a heterocyclic group, or a substituent formed by linking two or more substituents selected from the above exemplified substituents, or does not have any substituent. For example, the "substituent formed by linking two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent formed by linking two phenyl groups.

[0045] In one embodiment of the present specification, the term "substituted or unsubstituted" means that one or two or more substituents selected from deuterium, an alkyl group, an aryl group, and a heterocyclic group, or a substituent formed by linking two or more substituents selected from the above exemplified substituents, or does not have any substituent.

[0046] In the present specification, as examples of the halogen group, a fluorine group (-F), a chlorine group (-Cl), a bromine group (-Br), or an iodine group (-I) is exemplified.

[0047] In the present specification, a silyl group can be represented by the chemical formula of -SiYaYbYc, each of the above-mentioned Ya, Yb, and Yc can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The above-mentioned silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyl dimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto.

[0048] In the present specification, the above-mentioned alkyl group can 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 above-mentioned alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 10. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a t-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, an n-octyl group, and the like, but is not limited thereto.

[0049] The alkyl group described in the present specification and a substituent including an alkyl moiety other than the same are all inclusive of linear or branched forms.

[0050] In the present specification, a cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having a number of carbon atoms of 3 to 60, and according to one embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 6. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

[0051] In the present specification, an aryl group is not particularly limited, but is preferably an aryl group having a number of carbon atoms of 6 to 60, and can be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the above-mentioned aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned aryl group is 6 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned monocyclic aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned monocyclic aryl group is 6 to 20. As the above-mentioned aryl group, as a monocyclic aryl group, there are a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like. According to one embodiment, the number of carbon atoms of the above-mentioned monocyclic aryl group is 10 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned monocyclic aryl group is 10 to 20. As the above-mentioned polycyclic aryl group, there are a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto. As the above-mentioned polycyclic aryl group, there are a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto.

[0052] In the present specification, the substituted aryl group can include a structure in which an aliphatic hydrocarbon ring is fused to an aryl group. According to an embodiment, the above-mentioned substituted aryl group can include tetrahydronaphthyl, and more specifically, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, but is not limited thereto.

[0053] In the present specification, the fluorenyl group can be substituted, and two substituents can be combined with each other to form a spiro structure. At this time, the spiro structure can be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0054] In the case where the above-mentioned fluorenyl group is substituted, it can be a spirofluorenyl group; a (9,9-dimethylfluorenyl) group, and a (9,9-diphenylfluorenyl) group, and the like. However, it is not limited thereto.

[0055] In the present specification, the heterocyclic group is a ring group including one or more of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to an embodiment, the number of carbon atoms of the above-mentioned heterocyclic group is 2 to 30. According to an embodiment, the number of carbon atoms of the above-mentioned heterocyclic group is 2 to 20. As examples of the heterocyclic group, there are a pyridyl group, a pyrrolyl group, a pyrimidinyl group, a quinolyl group, a pyridazinyl group, a furanyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a benzonaphthothienyl group, an indolocarbazolyl group, a triazinyl group, and the like, but is not limited thereto.

[0056] In the present specification, the heteroaryl group is aromatic, and in addition thereto, the above-mentioned description about the heterocyclic group can be applied.

[0057] In the present specification, the above-mentioned arylene group, in addition to being divalent, the above-mentioned description about the aryl group can be applied.

[0058] In the present specification, the above-mentioned heterocyclic group, in addition to being divalent, the above-mentioned description about the heterocyclic group can be applied.

[0059] In the present specification, in a substituted or unsubstituted ring formed by combining with each other adjacent groups, the "ring" means a hydrocarbon ring or a heterocyclic ring.

[0060] The above-mentioned hydrocarbon ring can be an aromatic, aliphatic, or fused ring of an aromatic and aliphatic, and can be selected from the above-mentioned examples of the cycloalkyl group or the aryl group.

[0061] In the present specification, an aliphatic hydrocarbon ring refers to a ring which is not aromatic and is composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, but are not limited thereto.

[0062] In the present specification, an aromatic hydrocarbon ring refers to an aromatic ring composed of only carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, pentacene, hexacene, heptacene, octacene, and the like, but are not limited thereto. In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.

[0063] In the present specification, an aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepin azocane thiazocane and the like, but are not limited thereto.

[0064] In the present specification, an aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, isoxazole, isothiazole, triazole, oxazole, thiazole, isothiazole, triazole, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiapyran, diazine, oxazine, thiazine, dioxine, oxine, quinoline, quinazoline, quinoxaline, naphthylidine, acridine, phenanthridine, pteridine, indolizine, indazole, benzothiazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, diphenylcarbazole, phenoxazine, imidazopyridine, phen azin, indolocarbazole, indolocarbazole, and the like, but are not limited thereto.

[0065] Hereinafter, a preferred embodiment of the present application will be described in detail. However, the embodiment of the present application can be modified in various forms, and the scope of the present application is not limited to the embodiment described below.

[0066] ​​The compound represented by Chemical Formula 1 according to the present application has a structure in which two carbazoles are directly connected to a monocyclic nitrogen-containing ring group and a carbazole substituted with an aryl group are connected with an o-phenylene group as a connecting group, thereby having characteristics of improving luminous efficiency, improving driving voltage, and improving lifespan when the compound is used as a material of an organic light emitting device.

[0067] Hereinafter, the compound represented by Chemical Formula 1 will be described in detail.

[0068] [Chemical Formula 1]

[0069]

[0070] In the above Chemical Formula 1,

[0071] X1 to X3 are the same as or different from each other, and each is independently N, CH, or CD, at least one of X1 to X3 is N,

[0072] Ar1 is a substituted or unsubstituted aryl group,

[0073] R1 to R20 and Ra are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0074] Rb is hydrogen or deuterium,

[0075] p is an integer of 1 to 3, and when p is 2 or more, the two or more of Ra are the same as or different from each other,

[0076] q is an integer of 1 to 4, and when q is 2 or more, the two or more of Rb are the same as or different from each other.

[0077] In an embodiment of the present application, X1 to X3 are the same as or different from each other, and each is independently N, CH, or CD, and at least one of X1 to X3 is N.

[0078] In an embodiment of the present application, X1 to X3 are the same as or different from each other, and each is independently N, CH, or CD, and at least two of X1 to X3 are N.

[0079] In an embodiment of the present application, X1 to X3 are N.

[0080] In an embodiment of the present application, Ar1 is a substituted or unsubstituted aryl group.

[0081] In an embodiment of the present application, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0082] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0083] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0084] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0085] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0086] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted phenyl group.

[0087] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0088] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0089] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0090] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0091] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0092] In one embodiment of the present application, the aforementioned Ar1is a substituted or unsubstituted phenyl group.

[0093] In one embodiment of the present application, the aforementioned R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0094] In one embodiment of the present application, the aforementioned R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0095] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0096] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0097] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0098] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0099] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0100] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0101] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0102] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0103] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0104] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0105] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0106] In one embodiment of the present application, the above R1to R20and Raare the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0107] In one embodiment of the present application, Rb is hydrogen or deuterium.

[0108] In one embodiment of the present application, p is an integer of 1 to 3.

[0109] In one embodiment of the present application, p is 1.

[0110] In one embodiment of the present application, p is 2.

[0111] In one embodiment of the present application, p is 3.

[0112] In one embodiment of the present application, q is an integer of 1 to 4.

[0113] In one embodiment of the present application, q is 1.

[0114] In one embodiment of the present application, q is 2.

[0115] In one embodiment of the present application, q is 3.

[0116] In one embodiment of the present application, q is 4.

[0117] In one embodiment of the present application, R1 to R16 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0118] In one embodiment of the present application, R1 to R16 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0119] In one embodiment of the present application, R1 to R16 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0120] In one embodiment of the present application, R1 to R16 are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0121] In one embodiment of the present application, R1 to R16 are the same as or different from each other, and each independently hydrogen or deuterium.

[0122] In one embodiment of the present application, the above R1to R16are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a silyl group substituted with or not substituted with deuterium, an alkyl group substituted with or not substituted with deuterium, a cycloalkyl group substituted with or not substituted with deuterium, an aryl group substituted with or not substituted with deuterium, or a heteroaryl group substituted with or not substituted with deuterium.

[0123] In one embodiment of the present application, the above R1to R16are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group substituted with or not substituted with deuterium, or an aryl group substituted with or not substituted with deuterium.

[0124] In one embodiment of the present application, the above R1to R16are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group substituted with or not substituted with deuterium, or an aryl group substituted with or not substituted with deuterium.

[0125] In one embodiment of the present application, the above R1to R16are the same as or different from each other, and each independently hydrogen, deuterium, or an aryl group substituted with or not substituted with deuterium.

[0126] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted aryl group.

[0127] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0128] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0129] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0130] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0131] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0132] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted phenyl group.

[0133] In one embodiment of the present application, at least one of the above R1to R16is an aryl group substituted with or not substituted with deuterium.

[0134] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group having 6 to 30 carbon atoms which is substituted with deuterium or is unsubstituted.

[0135] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group having 6 to 20 carbon atoms which is substituted with deuterium or is unsubstituted.

[0136] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group having 6 to 12 carbon atoms which is substituted with deuterium or is unsubstituted.

[0137] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group which is substituted with deuterium or is unsubstituted, a biphenyl group which is substituted with deuterium or is unsubstituted, a terphenyl group which is substituted with deuterium or is unsubstituted, or a naphthyl group which is substituted with deuterium or is unsubstituted.

[0138] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group which is substituted with deuterium or is unsubstituted, or a biphenyl group which is substituted with deuterium or is unsubstituted.

[0139] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group which is substituted with deuterium or is unsubstituted.

[0140] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group which is substituted or is unsubstituted, and the others are hydrogen, deuterium, an alkyl group which is substituted or is unsubstituted, or an aryl group which is substituted or is unsubstituted.

[0141] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group which is substituted or is unsubstituted, and the others are hydrogen, deuterium, or an aryl group which is substituted or is unsubstituted.

[0142] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group which is substituted or is unsubstituted, and the others are hydrogen or deuterium.

[0143] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group having 6 to 30 carbon atoms which is substituted or is unsubstituted, and the others are hydrogen, deuterium, an alkyl group which is substituted or is unsubstituted, or an aryl group which is substituted or is unsubstituted.

[0144] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group having 6 to 20 carbon atoms which is substituted or is unsubstituted, and the others are hydrogen, deuterium, an alkyl group which is substituted or is unsubstituted, or an aryl group which is substituted or is unsubstituted.

[0145] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group having 6 to 12 carbon atoms which is substituted or is unsubstituted, and the others are hydrogen, deuterium, an alkyl group which is substituted or is unsubstituted, or an aryl group which is substituted or is unsubstituted.

[0146] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group, and the others are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0147] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and the others are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0148] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted phenyl group, and the others are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0149] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0150] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0151] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0152] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0153] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0154] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted phenyl group, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0155] In one embodiment of the present application, at least one of the aforementioned R1to R16is a substituted or unsubstituted aryl group, and the others are hydrogen or deuterium.

[0156] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the others are hydrogen or deuterium.

[0157] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the others are hydrogen or deuterium.

[0158] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and the others are hydrogen or deuterium.

[0159] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group, and the others are hydrogen or deuterium.

[0160] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and the others are hydrogen or deuterium.

[0161] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted phenyl group, and the others are hydrogen or deuterium.

[0162] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group, and the others are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0163] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0164] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group, and the others are hydrogen or deuterium.

[0165] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and the others are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0166] In one embodiment of the present application, at least one of the above R1 to R16 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the others are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0167] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0168] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0169] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0170] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0171] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0172] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0173] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0174] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0175] In one embodiment of the present application, at least one of the aforementioned R1to R16is a carbon number 6 to 12 aryl group substituted with deuterium or not, and the rest are hydrogen, deuterium, an alkyl group substituted with deuterium or not, or an aryl group substituted with deuterium or not.

[0176] In one embodiment of the present application, at least one of the above R1 to R16 is a phenyl group substituted with deuterium or non-substituted, and the others are hydrogen, deuterium, or an aryl group substituted with deuterium or non-substituted.

[0177] In one embodiment of the present application, at least one of the above R1 to R16 is an aryl group substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0178] In one embodiment of the present application, at least one of the above R1 to R16 is an aryl group having 6 to 30 carbon atoms substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0179] In one embodiment of the present application, at least one of the above R1 to R16 is an aryl group having 6 to 20 carbon atoms substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0180] In one embodiment of the present application, at least one of the above R1 to R16 is an aryl group having 6 to 12 carbon atoms substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0181] In one embodiment of the present application, at least one of the above R1 to R16 is a phenyl group substituted with deuterium or non-substituted, a biphenyl group substituted with deuterium or non-substituted, a terphenyl group substituted with deuterium or non-substituted, or a naphthyl group substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0182] In one embodiment of the present application, at least one of the above R1 to R16 is a phenyl group substituted with deuterium or non-substituted, or a biphenyl group substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0183] In one embodiment of the present application, at least one of the above R1 to R16 is a phenyl group substituted with deuterium or non-substituted, and the others are hydrogen or deuterium.

[0184] In one embodiment of the present application, the above R17 to R20 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or non-substituted silyl group, a substituted or non-substituted alkyl group, a substituted or non-substituted cycloalkyl group, a substituted or non-substituted aryl group, or a substituted or non-substituted heteroaryl group.

[0185] In one embodiment of the present application, the above R17 to R20 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or non-substituted alkyl group, or a substituted or non-substituted aryl group.

[0186] In one embodiment of the present application, the above R17 to R20 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or non-substituted alkyl group, or a substituted or non-substituted aryl group.

[0187] In one embodiment of the present application, the above R17to R20are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0188] In one embodiment of the present application, the above R17to R20are the same as or different from each other, and each independently hydrogen or deuterium.

[0189] In one embodiment of the present application, the above R17to R20are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a deuterium-substituted or unsubstituted silyl group, a deuterium-substituted or unsubstituted alkyl group, a deuterium-substituted or unsubstituted cycloalkyl group, a deuterium-substituted or unsubstituted aryl group, or a deuterium-substituted or unsubstituted heteroaryl group.

[0190] In one embodiment of the present application, the above R17to R20are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a deuterium-substituted or unsubstituted alkyl group, or a deuterium-substituted or unsubstituted aryl group.

[0191] In one embodiment of the present application, the above R17to R20are the same as or different from each other, and each independently hydrogen, deuterium, a deuterium-substituted or unsubstituted alkyl group, or a deuterium-substituted or unsubstituted aryl group.

[0192] In one embodiment of the present application, the above R17to R20are the same as or different from each other, and each independently hydrogen, deuterium, or a deuterium-substituted or unsubstituted aryl group.

[0193] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 contains at least one deuterium.

[0194] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 10% or more.

[0195] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 20% or more.

[0196] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 30% or more.

[0197] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 40% or more.

[0198] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 50% or more.

[0199] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 60% or more.

[0200] In one embodiment of the present application, the deuterium incorporation rate of the compound represented by the above formula 1 is 70% or more.

[0201] In one embodiment of the present application, the deuterium incorporation rate of the compound represented by the above formula 1 is 80% or more.

[0202] In one embodiment of the present application, the deuterium incorporation rate of the compound represented by the above formula 1 is 90% or more.

[0203] In one embodiment of the present application, the deuterium incorporation rate of the compound represented by the above formula 1 is 100%.

[0204] When the compound represented by formula 1 of the present application contains deuterium, the efficiency and the lifetime of the device are improved. The bond energy of C-D is greater than that of C-H, and thus, when the hydrogen in the compound is replaced with deuterium, the bond energy is stronger than that of the compound without deuterium, and the stability of the compound is improved. Therefore, when the compound contains deuterium, the decrease in quantum efficiency due to collision caused by the decrease in van der Waals force between molecules or the vibration between molecules is prevented, and thus, when the above compound is applied to an organic light emitting device, the lifetime characteristics of the device are improved.

[0205] In one embodiment of the present application, the above formula 1 is a compound represented by any one of the following formulas 1-1 to 1-4.

[0206] [Formula 1-1]

[0207]

[0208] [Formula 1-2]

[0209]

[0210] [Formula 1-3]

[0211]

[0212] [Formula 1-4]

[0213]

[0214] In the above formulas 1-1 to 1-4, X1to X3, Ar1, R1to R20, Rband q have the same definitions as those of formula 1, and Ra1to Ra3, each independently, are the same as or different from each other, and are hydrogen or deuterium.

[0215] In one embodiment of the present application, the above Ra1to Ra3, each independently, are the same as or different from each other, and are hydrogen or deuterium.

[0216] In one embodiment of the present application, the above chemical formula 1 is any one of the following compounds.

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226] The compound represented by chemical formula 1 according to one embodiment of the present specification can be manufactured by the method of the production example described later. The substituents can be combined by a method known in the art, and the kind, position, or number of the substituents can be changed according to a technique known in the art.

[0227] In the present specification, by introducing various substituents in the core structure of the compound represented by the above chemical formula 1, a compound having various energy band gaps can be synthesized. Further, in the present specification, by introducing various substituents in the core structure of the structure as described above, the HOMO and LUMO energy levels of the compound can also be adjusted.

[0228] In addition, the present specification provides an organic light emitting device including the above-mentioned compound.

[0229] In the present specification, "layer" is synonymous with "film" mainly used in the art, and refers to a coating layer covering a target area. The size of the above "layer" is not limited, and the size of each "layer" can be the same or different. According to one embodiment, the size of the "layer" can be equal to the entire device, can correspond to the size of a specific functional area, or can be as small as a single sub-pixel.

[0230] In the present specification, the meaning that a specific A substance is contained in a B layer includes both i) a case where one or more A substances are contained in one B layer, and ii) a case where the B layer is composed of one or more layers and the A substance is contained in one or more of the one or more B layers.

[0231] In the present specification, the meaning that a specific A substance is contained in a C layer or a D layer refers to all of the following cases: i) contained in one or more of the C layers, or ii) contained in one or more of the D layers, or iii) contained in one or more of the C layers and one or more of the D layers, respectively.

[0232] In the present specification, n-type refers to a substance that can take an electron from a host substance (a substance of an organic layer), and a generally known substance can be used, and is not limited thereto. That is, n-type can be defined as a substance having a property of being able to supply an electron to a LUMO (lowest unoccupied molecular orbital) level of a host. In contrast, p-type refers to a substance that, when a layer is formed only with a p-type substance, receives an electron from a HOMO (highest occupied molecular orbital) level of a substance located in a cathode direction, and generates a hole in the substance located in the cathode direction, or a substance that, when a p-type substance is doped in an arbitrary host, receives an electron from a HOMO of the host substance, and generates an equivalent hole in the HOMO of the host, and for this reason, when a layer is formed only with a p-type substance, the more adjacent the HOMO of the substance located in the cathode direction is to the LUMO of the p-type substance, the easier it is to take an electron from the HOMO of the adjacent layer, and generate a hole in the HOMO of the adjacent layer, and in addition, when a p-type substance is doped in an arbitrary host, the more adjacent the LUMO of the p-type substance is to the HOMO of the host, the easier it is to take an electron, and generate a hole in the host.

[0233] The present specification provides an organic light emitting device including: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers containing a compound of Chemical Formula 1.

[0234] The organic layers of the organic light emitting device of the present specification can be formed of a single layer structure, or can be formed of a multi-layer structure in which two or more organic layers are stacked. For example, a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like can be provided. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller number of organic layers.

[0235] According to an embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.

[0236] According to an embodiment of the present specification, the organic layer includes an electron blocking layer.

[0237] According to an embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0238] According to an embodiment of the present specification, the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

[0239] According to an embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

[0240] According to an embodiment of the present specification, the organic layer includes a hole blocking layer.

[0241] According to an embodiment of the present specification, the hole blocking layer of the organic layer includes the compound.

[0242] According to an embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

[0243] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

[0244] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer.

[0245] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as an n-type host of the light emitting layer.

[0246] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as an n-type phosphorescent host of the light emitting layer.

[0247] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as an n-type phosphorescent blue host of the light emitting layer.

[0248] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host, and further includes another host.

[0249] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host, and further includes a host and a dopant.

[0250] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a first host and a second host.

[0251] According to an embodiment of the present specification, the first host is an n-type host, and the second host is a p-type host.

[0252] According to an embodiment of the present specification, the first host is an n-type phosphorescent host, and the second host is a p-type phosphorescent host.

[0253] According to an embodiment of the present specification, the second host is a carbazole-based compound.

[0254] According to an embodiment of the present specification, the second host is a biscarbazole-based compound.

[0255] According to an embodiment of the present specification, the light emitting layer includes the first host and the second host in a weight ratio of 2:8 to 8:2, and the first host is the compound of Chemical Formula 1.

[0256] According to an embodiment of the present specification, the light emitting layer includes the first host and the second host in a weight ratio of 1:1, and the first host is the compound of Chemical Formula 1.

[0257] According to an embodiment of the present specification, the light emitting layer further includes a dopant.

[0258] According to an embodiment of the present specification, the light emitting layer includes the first host and the second host, and further includes a dopant.

[0259] According to an embodiment of the present specification, the dopant is a phosphorescent dopant.

[0260] According to an embodiment of the present specification, the dopant includes 1 to 20 parts by weight with respect to 100 parts by weight of the host.

[0261] According to an embodiment of the present specification, the light emitting layer includes a dopant, and the dopant further includes a phosphorescent dopant.

[0262] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes the phosphorescent dopant.

[0263] According to an embodiment of the present specification, the light emitting layer is a blue light emitting layer.

[0264] According to an embodiment of the present specification, the above-described light-emitting layer contains a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the host and the dopant are contained in a weight ratio of 99:1 to 50:50, more specifically, in a weight ratio of 99:1 to 95:5.

[0265] When the above-described light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrin platinum), or the like; or a fluorescent substance such as Alq3 (tris(8-hydroxyquinolino)aluminum), or the like, but not only limited thereto. When the light-emitting layer emits green light, as a light-emitting dopant, a phosphorescent substance such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium), or the like; or a fluorescent substance such as Alq3 (tris(8-hydroxyquinolino)aluminum), or the like, but not only limited thereto. When the light-emitting layer emits blue light, as a light-emitting dopant, a phosphorescent substance such as a platinum coordination compound, (4,6-F2ppy)2Irpic, or the like; or a fluorescent substance such as spiro-DPVBi, spiro-6P, DSB, DSA, a PFO-based polymer, a PPV-based polymer, or the like, but not only limited thereto.

[0266] According to an embodiment of the present specification, the above-described dopant is a metal coordination compound.

[0267] According to an embodiment of the present specification, the above-described dopant is a platinum coordination compound.

[0268] According to an embodiment of the present specification, the above-described dopant is an iridium coordination compound.

[0269] According to an embodiment of the present specification, the above-described dopant is the following Chemical Formula D-1 or D-2, but not only limited thereto.

[0270] [Chemical Formula D-1]

[0271]

[0272] [Chemical Formula D-2]

[0273]

[0274] In the above Chemical Formulae D-1 and D-2,

[0275] M is a transition metal,

[0276] A1, A3, A5, A6, K1, K2, and K3 are the same as or different from each other, and each is 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,

[0277] A2and A4are the same as or different from each other, and each is 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,

[0278] n is 1 or 2, and when n is 2, the structures within the parentheses are the same as or different from each other.

[0279] According to an embodiment of the present specification, the above M is iridium or platinum.

[0280] According to an embodiment of the present specification, the above dopant can be selected from the following structural formula, but is not limited thereto.

[0281]

[0282]

[0283]

[0284]

[0285] According to an embodiment of the present specification, the above organic layer further includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0286] According to an embodiment of the present specification, the above organic light emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, an emission layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0287] According to an embodiment of the present specification, the above organic light emitting device includes a first electrode; a second electrode disposed opposite to the above first electrode; an emitting layer disposed between the above first electrode and the above second electrode; and two or more organic layers disposed between the above emitting layer and the above first electrode, or between the above emitting layer and the above second electrode.

[0288] According to an embodiment of the present specification, the above two or more organic layers can be selected from two or more of the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0289] According to an embodiment of the present specification, two or more hole transport layers are included between the above emitting layer and the above first electrode. The above two or more hole transport layers can include the same or different substances from each other.

[0290] According to an embodiment of the present specification, the above first electrode is an anode or a cathode.

[0291] According to an embodiment of the present specification, the above second electrode is a cathode or an anode.

[0292] According to an embodiment of the present specification, the above organic light emitting device can be an organic light emitting device of a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0293] According to an embodiment of the present specification, the above organic light emitting device can be an organic light emitting device of an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0294] For example, the structure of an organic light emitting device according to an embodiment of the present specification is illustrated in Figure 1 and 2 . The above Figure 1 and 2 illustrate an organic light emitting device, and are not limited thereto.

[0295] Figure 1 The structure of an organic light emitting device in which a first electrode 2, an emitting layer 6, and a second electrode 9 are sequentially stacked on a substrate 1 is illustrated in FIG. 1. The above compound is included in the emitting layer.

[0296] Figure 2An organic light emitting device in which a first electrode 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 second electrode 9 are sequentially stacked on a substrate 1 is exemplified. The above compound is contained in the light emitting layer 6 and / or the hole blocking layer 7 and / or the electron injection and transport layer 8.

[0297] The organic light emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that the compound of the above formula 1 is contained in the electron injection layer, the electron transport layer, the electron injection and transport layer, the hole blocking layer, and / or the light emitting layer.

[0298] When the above organic light emitting device includes a plurality of organic layers, the above organic layers can be formed of the same substance or different substances.

[0299] For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured by forming an anode by evaporating a metal or a metal oxide having conductivity or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, then forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then evaporating a substance that can be used as a cathode on the organic layer. In addition to this method, an organic light emitting device can be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0300] In addition, the compound of the above formula 1 can be used to form an organic layer when manufacturing an organic light emitting device, not only by a vacuum evaporation method, but also by a solution coating method. Here, the solution coating method refers to a spin coating method, a dip coating method, a blade coating method, an inkjet printing method, a screen printing method, a spray method, a roll coating method, and the like, but is not limited thereto.

[0301] In addition to these methods, an organic light emitting device can be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate. However, the manufacturing method is not limited thereto.

[0302] As the anode material described above, a material having a large work function is generally preferred in order to enable a hole to be favorably injected into the organic layer. Examples include metals such as vanadium, chromium, copper, zinc, gold, and the like, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; electrically conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.

[0303] As the cathode material described above, a material having a small work function is generally preferred in order to enable an electron to be favorably injected into the organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0304] The light-emitting layer described above can include a host material and a dopant material. When the organic light-emitting device according to an embodiment of the present specification includes another light-emitting layer in addition to the light-emitting layer including the chemical formula 1 described above, the host material is an aromatic condensed ring derivative or a heterocyclic compound, or the like.

[0305] Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and as the heterocyclic compound, there are dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0306] As the dopant material described above, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamine group, and there are pyrene, anthracene, phenanthrene, fluoranthene, and the like having an arylamine group, but are not limited thereto. Further, the styrylamine compound is a compound having at least one arylvinyl group substituted on a substituted or unsubstituted arylamine group, and is substituted with one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups, or is unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. Further, as the metal complex, there are iridium complexes, platinum complexes, and the like, but are not limited thereto.

[0307] ​​The above-mentioned hole injection layer is a layer that receives holes from the electrode. The hole injection substance is preferably a substance that has a capability of transporting holes, has an effect of receiving holes from the anode, and has an excellent hole injection effect to the light-emitting layer or the light-emitting material. Further, it is preferable that the substance have an excellent capability of preventing excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Further, it is preferable that the substance have an excellent film formation capability. Further, it is preferable that the HOMO (Highest Occupied Molecular Orbital) of the hole injection substance be between the work function of the anode substance and the HOMO of the surrounding organic layer. As specific examples of the hole injection substance, there are metal porphyrin, oligothiophene, arylamine-based organic substance; hexacarbonitrile hexaazatriphenylene-based organic substance; quinacridone-based organic substance; perylene-based organic substance; anthraquinone, polyaniline, and polythiophene-based conductive polymer, but not limited thereto.

[0308] According to one embodiment of the present specification, the above-mentioned hole injection layer contains a compound represented by the following Chemical Formula HI-1, but not limited thereto.

[0309] [Chemical Formula HI-1]

[0310]

[0311] In the above-mentioned Chemical Formula HI-1,

[0312] R315 to R317 are the same as or different from each other, and each is independently any one selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof, or combine with an adjacent group to form a substituted or unsubstituted ring,

[0313] r315 is an integer of 1 to 5, and when the above-mentioned r315 is 2 or more, 2 or more of the above-mentioned R315 are the same as or different from each other,

[0314] r316 is an integer of 1 to 5, and when the above-mentioned r316 is 2 or more, 2 or more of the above-mentioned R316 are the same as or different from each other.

[0315] According to one embodiment of the present specification, the above-mentioned R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0316] According to one embodiment of the present specification, the above-mentioned R317 is any one selected from the group consisting of a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, and a combination thereof.

[0317] According to one embodiment of the present specification, the above R315 and R316 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or are each independently combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an aryl group or an alkyl group.

[0318] According to one embodiment of the present specification, the above R315 and R316 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or are each independently combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an aryl group or an alkyl group.

[0319] According to one embodiment of the present specification, the above chemical formula HI-1 is represented by any one of the following compounds.

[0320]

[0321]

[0322] According to one embodiment of the present specification, the above hole injection layer contains a compound represented by the following chemical formula HI-2, but is not limited thereto.

[0323] [Chemical Formula HI-2]

[0324]

[0325] In the above chemical formula HI-2,

[0326] R401 to R403 are the same as or different from each other, and each is independently a halogen group,

[0327] r401 to r403 are 4.

[0328] According to one embodiment of the present specification, the above R401 to R403 are F.

[0329] According to one embodiment of the present specification, the above chemical formula HI-2 is represented by the following compound.

[0330]

[0331] According to one embodiment of the present specification, the above hole injection layer contains the above chemical formulas HI-1 and HI-2.

[0332] According to one embodiment of the present specification, the above hole injection layer contains the above chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0333] The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer. The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer them to the light-emitting layer, and is preferably a substance having a large mobility for holes. Specific examples include arylamine-based organic compounds, electrically conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but are not limited thereto.

[0334] According to an embodiment of the present specification, the hole-transporting layer contains a compound represented by Chemical Formula HI-1, but is not limited thereto.

[0335] According to an embodiment of the present specification, the hole-injecting and transporting layer is a layer that transports holes to the light-emitting layer. The substances exemplified in the hole-transporting layer and the hole-injecting layer can be used, but are not limited thereto.

[0336] The electron-transporting layer is a layer that receives electrons from the electron-injecting layer and transports the electrons to the light-emitting layer. The electron-transporting substance is a substance that can receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a substance having a large mobility for electrons. Specific examples include an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, and the like, but are not limited thereto. The electron-transporting layer can be used with any desired cathode substance as used in the prior art. In particular, a suitable cathode substance is a general substance having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, each of which is accompanied by an aluminum layer or a silver layer.

[0337] The electron-injecting layer is a layer that receives electrons from the electrode. As the electron-injecting substance, a substance having an excellent ability to transport electrons, having an effect of receiving electrons from the second electrode, and having an excellent electron-injecting effect on the light-emitting layer or the light-emitting material is preferred. In addition, a substance that prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer and has an excellent film-forming ability is preferred. As the electron-injecting layer substance, specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

[0338] As the above metal coordination compound, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), gallium bis(2-methyl-8-quinolinate) chloride, gallium bis(2-methyl-8-quinolinate) (o-cresol), aluminum bis(2-methyl-8-quinolinate) (o-naphthol), gallium bis(2-methyl-8-quinolinate) (2-naphthol), and the like, but are not limited thereto.

[0339] According to one embodiment of the present specification, the above-mentioned electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the above-mentioned organic light-emitting device includes an electron injection and transport layer other than the electron injection and transport layer including the compound of the above-mentioned Chemical Formula 1, the substances exemplified in the above-mentioned electron transport layer and electron injection layer can be used, but are not limited thereto.

[0340] According to one embodiment of the present specification, the above-mentioned electron injection and transport layer includes a compound represented by the following Chemical Formula ET-1, but is not limited thereto.

[0341] [Chemical Formula ET-1]

[0342]

[0343] In the above-mentioned Chemical Formula ET-1,

[0344] At least one of Z11 to Z13 is N, and the rest are CH,

[0345] At least one of Z21 to Z23 is N, and the rest are CH,

[0346] L601 and L602 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0347] Ar601 to Ar604 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0348] According to one embodiment of the present specification, the above-mentioned L601 and L602 are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0349] According to one embodiment of the present specification, the above-mentioned L601 and L602 are phenylene.

[0350] According to an embodiment of the present specification, the above Ar601 to Ar604 are the same as or different from each other, and each is independently a substituted or unsubstituted, monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0351] According to an embodiment of the present specification, the above Ar601 to Ar604 are phenyl.

[0352] According to an embodiment of the present specification, the above Chemical Formula ET-1 is represented by the following compound.

[0353]

[0354] According to an embodiment of the present specification, the above electron injection and transport layer can further include a metal complex compound. The above metal complex compound is as described above.

[0355] The above electron blocking layer is a layer for preventing electrons injected from the electron injection layer from passing through the light emitting layer to enter the hole injection layer, thereby improving the lifespan and efficiency of the device. In the case where the above electron blocking layer includes an additional electron blocking layer other than the electron blocking layer including the compound of Chemical Formula 1 according to an embodiment of the present specification, a well-known material can be used without limitation, and the substances exemplified in the description of the above hole injection layer can be used, but are not limited thereto. The above electron blocking layer can be formed between the light emitting layer and the hole transport layer, between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer simultaneously performing hole injection and hole transport.

[0356] The above hole blocking layer is a layer for blocking holes from reaching the cathode, and can be formed using the same conditions as the electron injection layer. Specifically, there are A diazole derivative or a triazole derivative, a phenanthroline derivative, an aluminum complex, and the like, but are not limited thereto.

[0357] According to an embodiment of the present specification, in the case where the above organic light emitting device includes a hole blocking layer other than the hole blocking layer including the above compound of Chemical Formula 1, the substances exemplified in the above hole blocking layer can be used, but are not limited thereto.

[0358] For example, the above hole blocking layer includes a compound represented by the following Chemical Formula HB-1, but is not limited thereto.

[0359] [Chemical Formula HB-1]

[0360]

[0361] In the above HB-1,

[0362] At least one of Q1 to Q3 is N, and the rest are CH,

[0363] L701is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroaryl group,

[0364] T1to T3are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0365] According to an embodiment of the present specification, the above-described Q1to Q3are N.

[0366] According to an embodiment of the present specification, the above-described L701is a direct bond, or a substituted or unsubstituted arylene having 6 to 30 carbon atoms.

[0367] According to an embodiment of the present specification, the above-described L701is a direct bond or arylene.

[0368] According to an embodiment of the present specification, the above-described L701is a direct bond, or arylene having 6 to 30 carbon atoms.

[0369] According to an embodiment of the present specification, the above-described L701is a direct bond or phenylene.

[0370] According to an embodiment of the present specification, the above-described T1to T3are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group.

[0371] According to an embodiment of the present specification, the above-described T1to T3are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

[0372] According to an embodiment of the present specification, the above-described T1to T3are the same as or different from each other, and each independently a heteroaryl group.

[0373] According to an embodiment of the present specification, the above-described T1to T3are the same as or different from each other, and each independently a heteroaryl group having 6 to 30 carbon atoms.

[0374] According to an embodiment of the present specification, the above-described T1to T3are carbazolyl.

[0375] According to an embodiment of the present specification, the above-described Chemical Formula HB-1may include, but is not limited to, the following compounds.

[0376]

[0377] According to an embodiment of the present specification, the above-described Chemical Formula HB-1may be used as a first host material of the light-emitting layer.

[0378] According to an embodiment of the present specification, the above-described Chemical Formula HB-1may be used as a second host material of the light-emitting layer.

[0379] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0380] The organic light-emitting device according to the present specification can be included in various electronic devices and used. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0381] In order to specifically explain this specification, the following examples and comparative examples will be given for detailed description. However, the examples and comparative examples of this specification can be modified into various forms, and the scope of this specification is not to be construed as being limited to the examples and comparative examples described in detail below.

[0382] The Examples and Comparative Examples of this specification are provided to more completely explain this specification to those skilled in the art.

[0383] [Manufacturing Example]

[0384] <Production Example 1> Synthesis of Compound 1

[0385]

[0386] Under a nitrogen atmosphere, in a 500 ml round-bottom flask, compounds 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (5.50 g, 12.33 mmol) and a-1 (5.15 g, 14.18 mmol) were completely dissolved in 240 ml of tetrahydrofuran (THF). A 2M aqueous potassium carbonate solution (120 ml) was then added, followed by the addition of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.43 g, 0.37 mmol), and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The mixture was recrystallized from 280 ml of ethyl acetate to produce compound 1 (5.78 g, 64%).

[0387] MS[M+H] + =729

[0388] <Production Example 2> Synthesis of Compound 2

[0389]

[0390] After compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (5.50 g, 12.33 mmol) and compound a-2 (5.15 g, 14.18 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis(triphenylphosphine)palladium (0.43 g, 0.37 mmol), it was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure, and recrystallized with 270 mL of ethyl acetate, thereby producing compound 2 (5.03 g, 56%).

[0391] MS [M+H] + = 729

[0392] <Manufacturing Example 3> Synthesis of compound 3

[0393]

[0394] After compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (5.50 g, 12.33 mmol) and compound a-3 (5.15 g, 15.18 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis(triphenylphosphine)palladium (0.43 g, 0.37 mmol), it was heated and stirred for 7 hours. After the temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate, thereby producing compound 3 (5.34 g, 59%).

[0395] MS [M+H] + = 729

[0396] <Manufacturing Example 4> Synthesis of compound 4

[0397]

[0398] After compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (3.50 g, 7.58 mmol) and compound a-4 (3.30 g, 8.71 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis(triphenylphosphine)palladium (0.26 g, 0.23 mmol), it was heated and stirred for 5 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate, thereby producing compound 4 (3.24 g, 56%).

[0399] MS [M+H] + = 762

[0400] <Manufacturing Example 5> Synthesis of compound 5

[0401]

[0402] After compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (3.50 g, 7.58 mmol) and compound a-5 (3.30 g, 8.71 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M aqueous potassium carbonate solution (120 mL) was added, and after adding tetrakis(triphenylphosphine)palladium (0.26 g, 0.23 mmol), it was heated and stirred for 4 hours. After the temperature was lowered to room temperature, the aqueous layer was removed, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure, and recrystallized with 320 mL of ethyl acetate, thereby producing compound 5 (3.66 g, 63%).

[0403] MS [M+H] + = 762

[0404] <Manufacturing Example 6> Synthesis of compound 6

[0405]

[0406] After compound 9,9'-(6-chloro-1,3,5-triazin-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (3.50 g, 7.58 mmol) and compound a-6 (3.30 g, 8.71 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M aqueous potassium carbonate solution (120 mL) was added, and after Pd(PPh3)4 (0.26 g, 0.23 mmol) was added, it was heated and stirred for 5 hours. After the temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure, and recrystallized with 270 mL of ethyl acetate, thereby producing compound 6 (3.45 g, 60%).

[0407] MS [M+H] + = 762

[0408] <Manufacturing Example 7> Synthesis of compound 7

[0409]

[0410] After compound 9-(4-(9H-carbazol-9-yl)-6-chloro-1,3,5-triazin-2-yl)-3-phenyl-9H-carbazole (4.50 g, 8.62 mmol) and a-1 (3.60 g, 9.91 mmol) were completely dissolved in 240 mL of tetrahydrofuran (THF) in a 500 mL round bottom flask under a nitrogen atmosphere, 2 M aqueous potassium carbonate solution (120 mL) was added, and after Pd(PPh3)4 (0.30 g, 0.26 mmol) was added, it was heated and stirred for 5 hours. After the temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate, thereby producing compound 7 (4.77 g, 69%).

[0411] MS [M+H] + = 805

[0412] <Manufacturing Example 8> Synthesis of compound 8

[0413]

[0414] Under a nitrogen atmosphere, in a 500 ml round-bottom flask, compounds 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (4.50 g, 10.09 mmol) and a-7 (5.09 g, 11.60 mmol) were completely dissolved in 240 ml of tetrahydrofuran (THF). A 2M aqueous potassium carbonate solution (120 ml) was then added, followed by the addition of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.35 g, 0.30 mmol), and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The mixture was recrystallized from 240 ml of ethyl acetate to produce compound 8 (5.12 g, 63%).

[0415] MS[M+H] + =805

[0416] [Example]

[0417] Example 1-1

[0418] ITO (indium tin oxide) is used to The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0419] 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). A hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 was deposited. Then, a hole transport layer is formed by vacuum evaporation. The compound of BH (p-type) was vacuum deposited to form an electron blocking layer. Next, on the electron blocking layer, a mixture of the compound of BH (p-type) which is a p-type host of a light emitting layer and the compound 1 synthesized in the above Production Example 1 which is an n-type host of a light emitting layer were mixed at 1:1 (weight ratio) and a compound represented by the following formula BD was vacuum deposited at a weight ratio of 88:12 to form a light emitting layer. On the light emitting layer, a compound represented by the following formula ET1 was vacuum deposited at a thickness of 10 nm to form an electron injection and transport layer. The compound represented by the following formula HB1 was vacuum deposited to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer at a thickness of 50 nm. On the electron injection and transport layer, lithium fluoride (LiF) was vacuum deposited at a thickness of 1 nm, aluminum was vacuum deposited at a thickness of 200 nm to form a cathode.

[0420]

[0421] In the above process, the deposition rate of the organic material was maintained at 0.1 nm / sec. The deposition rate of the lithium fluoride of the cathode was maintained at 0.1 nm / sec, and the deposition rate of the aluminum was maintained at 1 nm / sec. At the time of deposition, the degree of vacuum was maintained at 2 x 10 -7 -6

[0422] Examples 1-2 to 1-8

[0423] The organic light emitting device was produced by the same method as the above Example 1-1, except that the compound 2 to 8 described in the following Table 1 were used instead of the compound of Production Example 1.

[0424] [Comparative Example]

[0425] Comparative Examples 1-1 to 1-8

[0426] The organic light emitting device was produced by the same method as the above Example 1-1, except that the compound described in the following Table 1 was used instead of the compound of Production Example 1.

[0427] The compounds of BH1 (n-type) to BH8 (n-type) used in the following Table 1 are shown below.

[0428]

[0429] [Experimental Example]

[0430] ​​​​​​​When a current was applied to the organic light emitting devices manufactured in Examples 1-1 to 1-8 and Comparative Examples 1-1 to 1-8 described above, voltage, efficiency, color coordinates, and lifespan were measured, and the results thereof are shown in Table 1 below.

[0431] T95 means a time required for luminance to decrease to 95% from initial luminance (1600 nits).

[0432] [Table 1]

[0433]

[0434] As shown in Table 1 above, the organic light emitting devices of Examples 1-1 to 1-8 using the compound of Chemical Formula 1 according to one embodiment of the present specification in which a carbazole substituted with an aryl group is directly connected to a triazine core with an o-phenylene group as a connecting group showed superior characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device.

[0435] Specifically, Examples 1-1 to 1-8 including the compound of Chemical Formula 1 according to one embodiment of the present specification showed superior characteristics in terms of efficiency, driving voltage, and stability compared to Comparative Example 1-1 including a compound BH1 in which a carbazolyl group has no substituent, Comparative Examples 1-2 and 1-3 including compounds BH2 and BH3 in which a connecting group is a p-phenylene group, Comparative Example 1-4 including a compound BH4 in which three carbazoles are directly connected to a triazine, and Comparative Examples 1-5 to 1-8 including compounds BH5 to BH8 in which a connecting position of a carbazole directly connected to a triazine is different from the present application or one carbazole is directly connected to a triazine.

[0436] Examples 1-1 to 1-8 using the compound of the present specification in which Ar is an aryl group and Rb is hydrogen or deuterium also showed superior characteristics in terms of efficiency, driving voltage, and stability compared to Comparative Examples 9 and 10 using a compound BH9 in which Ar is hydrogen and a compound BH10 in which Ar is hydrogen and Rb is CN.

[0437] The preferred embodiments of the present specification were described through the above content, but the present specification is not limited thereto, and can be variously modified within the scope of the present specification and the detailed description of the invention, and it also belongs to the scope of the present specification.

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] ###0001### In the Chemical Formula 1, X1 to X3 are the same as or different from each other, and each is independently N, CH, or CD, at least one of X1 to X3 is N, Ar1 is a substituted or unsubstituted aryl group, R1 to R20 and Ra are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Rb is hydrogen or deuterium, p is an integer of 1 to 3, and when p is 2 or more, the 2 or more of Ra are the same as or different from each other, and q is an integer of 1 to 4, and when q is 2 or more, the 2 or more of Rb are the same as or different from each other. The Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-4: [Chemical Formula 1-1] ###0002### [Chemical Formula 1-2] ###0003### [Chemical Formula 1-3] ###0004### [Chemical Formula 1-4] ###0005### In the Chemical Formulae 1-1 to 1-4, X1 to X3, Ar1, R1 to R20, Rb, and q are defined the same as in the Chemical Formula 1, and Ra1 to Ra3 are the same as or different from each other, and each is independently hydrogen or deuterium. The X1 to X3 are N. The Ar1 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. At least one of R1 to R16 is a substituted or unsubstituted aryl group. At least one of R1 to R16 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. The compound represented by the Chemical Formula 1 contains at least one deuterium. R1 to R20 and Ra are the same as or different from each other, and each is independently hydrogen, deuterium, an alkyl group substituted or unsubstituted with deuterium, or an aryl group substituted or unsubstituted with deuterium. The Chemical Formula 1 is any one of the following compounds: a compound represented by the following Chemical Formula 2: [Chemical Formula 2] ###0006### a compound represented by the following Chemical Formula 3: [Chemical Formula 3] ###0007### a compound represented by the following Chemical Formula 4: [Chemical Formula 4] ###0008### a compound represented by the following Chemical Formula 5: [Chemical Formula 5] ###0009### a compound represented by the following Chemical Formula 6: [Chemical Formula 6] ###0010### a compound represented by the following Chemical Formula 7: [Chemical Formula 7] ###0011### a compound represented by the following Chemical Formula 8: [Chemical Formula 8] ###0012### a compound represented by the following Chemical Formula 9: [Chemical Formula 9] ###0013### a compound represented by the following Chemical Formula 10: [Chemical Formula 10] ###0014### a compound represented by the following Chemical Formula 11: [Chemical Formula 11] ###0015### a compound represented by the following Chemical Formula 12: [Chemical Formula 12] ###0016### a compound represented by the following Chemical Formula 13: [Chemical Formula 13] ###0017### a compound represented by the following Chemical Formula 14: [Chemical Formula 14] ###0018### a compound represented by the following Chemical Formula 15: [Chemical Formula 15] ###0019### a compound represented by the following Chemical Formula 16: [Chemical Formula 16] ###0020### a compound represented by the following Chemical Formula 17: [Chemical Formula 17] ###0021### a compound represented by the following Chemical Formula 18: [Chemical Formula 18] ###0022### a compound represented by the following Chemical Formula 19: [Chemical Formula 19] ###0023### a compound represented by the following Chemical Formula 20: [Chemical Formula 20] ###0024### a compound represented by the following Chemical Formula 21: [Chemical Formula 21] ###0025### a compound represented by the following Chemical Formula 22: [Chemical Formula 22] ###0026### a compound represented by the following Chemical Formula 23: [Chemical Formula 23] ###0027### a compound represented by the following Chemical Formula 24: [Chemical Formula 24] ###0028### a compound represented by the following Chemical Formula 25: [Chemical Formula 25] ###0029### a compound represented by the following Chemical Formula 26: [Chemical Formula 26] ###0030### a compound represented by the following Chemical Formula 27: [Chemical Formula 27] ###0031### a compound represented by the following Chemical Formula 28: [Chemical Formula 28] ###0032### a compound represented by the following Chemical Formula 29: [Chemical Formula 29] ###0033### a compound represented by the following Chemical Formula 30: [Chemical Formula 30] ###0034### a compound represented by the following Chemical Formula 31: [Chemical Formula 31] ###0035### a compound represented by the following Chemical Formula 32: [Chemical Formula 32] ###0036### a compound represented by the following Chemical Formula 33: [Chemical Formula 33] ###0037### a compound represented by the following Chemical Formula 34: [Chemical Formula 34] ###0038### a compound represented by the following Chemical Formula 35: [Chemical Formula 35] ###0039### a compound represented by the following Chemical Formula 36: [Chemical Formula 36] ###0040### a compound represented by the following Chemical Formula 37: [Chemical Formula 37] ###0041### a compound represented by the following Chemical Formula 38: [Chemical Formula 38] ###0042### a compound represented by the following Chemical Formula 39: [Chemical Formula 39] ###0043### a compound represented by the following Chemical Formula 40: [Chemical Formula 40] ###0044### a compound represented by the following Chemical Formula 41: [Chemical Formula 41] ###0045### a compound represented by the following Chemical Formula 42: [Chemical Formula 42] ###0046### a compound represented by the following Chemical Formula 43: [Chemical Formula 43] ###0047### a compound represented by the following Chemical Formula 44: [Chemical Formula 44] ###0048### a compound represented by the following Chemical Formula 45: [Chemical Formula 45] ###0049### a compound represented by the following Chemical Formula 46: [Chemical Formula 46] ###0050### a compound represented by the following Chemical Formula 47: [Chemical Formula 47] ###0051### a compound represented by the following Chemical Formula 48: [Chemical Formula 48] ###0052### a compound represented by the following Chemical Formula 49: [Chemical Formula 49] ###0053### a compound represented by the following Chemical Formula 50: [Chemical Formula 50] ###0054### a compound represented by the following Chemical Formula 51: [Chemical Formula 51] ###0055### a compound represented by the following Chemical Formula 52: [Chemical Formula 52] ###0056### a compound represented by the following Chemical Formula 53: [Chemical Formula 53] ###0057### a compound represented by the following Chemical Formula 54: [Chemical Formula 54] ###0058### a compound represented by the following Chemical Formula 55: [Chemical Formula 55] ###0059### a compound represented by the following Chemical Formula 56: [Chemical Formula 56] ###0060### a compound represented by the following Chemical Formula 57: [Chemical Formula 57] ###0061### a compound represented by the following Chemical Formula 58: [Chemical Formula 58] ###0062### a compound represented by the following Chemical Formula 59: [Chemical Formula 59] ###0063### a compound represented by the following Chemical Formula 60: [Chemical Formula 60] ###0064### 2. The compound of claim 1, wherein, ​ ​ ​ ​ ​ ​ 3. The compound of claim 1, wherein, ​ 4. The compound of claim 1, wherein, ​ 5. The compound of claim 1, wherein, ​ 6. The compound of claim 1, wherein, ​ 7. The compound of claim 1, wherein, ​ 8. The compound of claim 1, wherein, ​ 9. The compound of claim 1, wherein, ​ 10. An organic light emitting device comprising: ​ ​ 11. The organic light emitting device according to claim 10, wherein, ​ ​ 12. The organic light emitting device of claim 11, wherein, ​ 13. The organic light emitting device of claim 11, wherein, ​ ​ 14. The organic light emitting device of claim 13, wherein, ​ 15. The organic light emitting device of claim 10, wherein, ​ ​ 16. The organic light emitting device of claim 10, wherein, ​ ​

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