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. 10-2024-0051905, filed on April 18, 2024, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety.

[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 said to "comprise" a certain component, unless particularly stated to the contrary, it means that further components can be further included, rather than excluding other components.

[0035] In the present specification, when a certain member is said to be positioned "on" another member, it includes not only the case where the certain member is in contact with the other member, but also the case where other members are present between the two members.

[0036] In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital function (highest occupied molecular orbital) in which an electron is present 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 present 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 the levels of HOMO and LUMO, 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 phrase "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 that one or more selected from the above components is included.

[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, substituted 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 deuterium substituted 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 substituted with one or two or more substituents selected from the group consisting of 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 substituted with a substituent in which two or more of the above-mentioned substituents are linked, or not having any substituent. For example, the "substituent in which two or more are linked" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent in which two phenyl groups are linked.

[0045] In one embodiment of the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or not having any substituent.

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

[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.

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

[0053] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0054] In the case where the above fluorenyl group is substituted, it can be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups, but are not limited thereto.

[0055] In the present specification, a heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of heterocyclic groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, and triazinyl.

[0056] In the present specification, a heteroaryl group is aromatic, and other than this, the above description of the heterocyclic group is applicable.

[0057] In the present specification, the description of the above-mentioned aryl group is applicable to the above-mentioned arylene group except that the above-mentioned arylene group is divalent.

[0058] In the present specification, the same description as for the above-mentioned heterocyclic group applies to the divalent heterocyclic group except that the divalent group is divalent.

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

[0060] The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from the examples of the cycloalkyl group or aryl group described above.

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

[0062] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, Examples include, but are not limited to, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.

[0063] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctanes etc., but not limited thereto.

[0064] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, isocyanates Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolocarbazole, indenocarbazole, etc., but are not limited to these.

[0065] According to the present invention, the compound represented by Chemical Formula 1 has a structure in which two carbazole cores are directly connected to a monocyclic nitrogen-containing ring group and the carbazoles substituted by aryl groups are connected via a m-phenylene group as a connecting group. Therefore, when the above compound is used as a material for an organic light-emitting device, it has the characteristics of improving the luminous efficiency of the organic light-emitting device, improving the driving voltage, and increasing the life of the organic light-emitting device.

[0066] Hereinafter, the compound represented by Chemical Formula 1 will be described in detail.

[0067] [Chemical Formula 1]

[0068]

[0069] In the above Chemical Formula 1,

[0070] X1 to X3 are the same as or different from each other and are each independently N, CH or CD, at least one of X1 to X3 is N,

[0071] Ar1 is a substituted or unsubstituted aryl group,

[0072] R1 to R20 and Ra are the same as or different from each other, and are 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,

[0073] Rb is hydrogen or deuterium,

[0074] p is an integer from 1 to 3. When p is 2 or more, the two or more Ra are the same as or different from each other.

[0075] q is 1 to 4.

[0076] In one embodiment of the present invention, X1 to X3 are the same as or different from each other, and are independently N, CH or CD, and at least one of X1 to X3 is N.

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

[0078] In one embodiment of the present invention, X1 to X3 are N.

[0079] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted aryl group.

[0080] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0081] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0082] In one embodiment of the present invention, Ar1 is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0083] In one embodiment of the present application, the above 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.

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

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

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

[0087] In one embodiment of the present application, the above Ar1is a substituted or unsubstituted phenyl group.

[0088] In one embodiment of the present application, the above Ar1is a substituted or unsubstituted phenyl group.

[0089] In one embodiment of the present application, the above Ar1is a substituted or unsubstituted phenyl group.

[0090] In one embodiment of the present application, the above Ar1is a substituted or unsubstituted phenyl group.

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

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

[0093] 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 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 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.

[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 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.

[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, p is an integer of 1 to 3.

[0108] In one embodiment of the present application, p is 1.

[0109] In one embodiment of the present application, p is 2.

[0110] In one embodiment of the present application, p is 3.

[0111] In one embodiment of the present application, q is an integer of 1 to 4.

[0112] In one embodiment of the present application, q is 1.

[0113] In one embodiment of the present application, q is 2.

[0114] In one embodiment of the present application, q is 3.

[0115] In one embodiment of the present application, q is 4.

[0116] In one embodiment of the present application, R1to R16are 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.

[0117] In one embodiment of the present application, R1to R16are 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.

[0118] In one embodiment of the present application, R1to R16are 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.

[0119] In one embodiment of the present application, R1to R16are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0120] In one embodiment of the present application, R1to R16are the same as or different from each other, and each independently hydrogen or deuterium.

[0121] In one embodiment of the present application, R1to R16are 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.

[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, an alkyl group substituted with or not substituted with deuterium, or an aryl 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, 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, or an aryl group substituted with or not substituted with deuterium.

[0125] In one embodiment of the present application, at least one of the above R1to R16is a substituted or unsubstituted aryl group.

[0126] 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.

[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 20 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 12 carbon atoms.

[0129] 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.

[0130] 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.

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

[0132] 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.

[0133] In one embodiment of the present application, at least one of the above R1to R16is an aryl group having 6 to 30 carbon atoms substituted with or not substituted with deuterium.

[0134] In one embodiment of the present application, at least one of the above R1to R16is an aryl group having 6 to 20 carbon atoms substituted with or not substituted with deuterium.

[0135] 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 not substituted.

[0136] 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 not substituted, a biphenyl group which is substituted with deuterium or is not substituted, a terphenyl group which is substituted with deuterium or is not substituted, or a naphthyl group which is substituted with deuterium or is not substituted.

[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 not substituted, or a biphenyl group which is substituted with deuterium or is not substituted.

[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 not substituted.

[0139] 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 not substituted, and the rest is hydrogen, deuterium, an alkyl group which is substituted or is not substituted, or an aryl group which is substituted or is not substituted.

[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 not substituted, and the rest is hydrogen, deuterium, or an aryl group which is substituted or is not substituted.

[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 not substituted, and the rest is hydrogen or deuterium.

[0142] 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 not substituted, and the rest is hydrogen, deuterium, an alkyl group which is substituted or is not substituted, or an aryl group which is substituted or is not substituted.

[0143] 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 not substituted, and the rest is hydrogen, deuterium, an alkyl group which is substituted or is not substituted, or an aryl group which is substituted or is not substituted.

[0144] 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 not substituted, and the rest is hydrogen, deuterium, an alkyl group which is substituted or is not substituted, or an aryl group which is substituted or is not substituted.

[0145] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group which is substituted or is not substituted, a biphenyl group which is substituted or is not substituted, a terphenyl group which is substituted or is not substituted, or a naphthyl group which is substituted or is not substituted, and the rest is hydrogen, deuterium, an alkyl group which is substituted or is not substituted, or an aryl group which is substituted or is not substituted.

[0146] 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, 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 above 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.

[0148] 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, and the others are hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0149] 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, 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 above 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.

[0151] 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, 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 above 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.

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

[0155] 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, and the others are hydrogen or deuterium.

[0156] 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, 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 12 carbon atoms, and the rest 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 phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group, and the rest 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, or a substituted or unsubstituted biphenyl group, and the rest 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, and the rest 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 aryl group, and the rest are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[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 rest are hydrogen, deuterium, 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 rest are hydrogen or deuterium.

[0164] 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 rest are hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[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 20 carbon atoms, and the rest 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 12 carbon atoms, and the rest 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 R1 to R16 is a phenyl group substituted with deuterium or an unsubstituted phenyl group, a biphenyl group substituted with deuterium or an unsubstituted biphenyl group, a terphenyl group substituted with deuterium or an unsubstituted terphenyl group, or a naphthyl group substituted with deuterium or an unsubstituted naphthyl group, and the rest is hydrogen, deuterium, an alkyl group substituted with deuterium or an unsubstituted alkyl group, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0168] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group substituted with deuterium or an unsubstituted phenyl group, or a biphenyl group substituted with deuterium or an unsubstituted biphenyl group, and the rest is hydrogen, deuterium, an alkyl group substituted with deuterium or an unsubstituted alkyl group, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0169] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group substituted with deuterium or an unsubstituted phenyl group, and the rest is hydrogen, deuterium, an alkyl group substituted with deuterium or an unsubstituted alkyl group, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0170] 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 substituted with deuterium or an unsubstituted aryl group, and the rest is hydrogen, deuterium, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0171] 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 substituted with deuterium or an unsubstituted aryl group, and the rest is hydrogen, deuterium, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0172] 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 substituted with deuterium or an unsubstituted aryl group, and the rest is hydrogen, deuterium, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0173] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group substituted with deuterium or an unsubstituted phenyl group, a biphenyl group substituted with deuterium or an unsubstituted biphenyl group, a terphenyl group substituted with deuterium or an unsubstituted terphenyl group, or a naphthyl group substituted with deuterium or an unsubstituted naphthyl group, and the rest is hydrogen, deuterium, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0174] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group substituted with deuterium or an unsubstituted phenyl group, or a biphenyl group substituted with deuterium or an unsubstituted biphenyl group, and the rest is hydrogen, deuterium, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0175] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is a phenyl group substituted with deuterium or an unsubstituted phenyl group, and the rest is hydrogen, deuterium, or an aryl group substituted with deuterium or an unsubstituted aryl group.

[0176] In one embodiment of the present application, at least one of the aforementioned R1 to R16 is an aryl group substituted with deuterium or an unsubstituted aryl group, and the rest is hydrogen or deuterium.

[0177] In one embodiment of the present application, at least one of the aforementioned R1to R16is an aryl group having a carbon number of 6 to 30 which is substituted with deuterium or is unsubstituted, and the rest are hydrogen or deuterium.

[0178] In one embodiment of the present application, at least one of the aforementioned R1to R16is an aryl group having a carbon number of 6 to 20 which is substituted with deuterium or is unsubstituted, and the rest are hydrogen or deuterium.

[0179] In one embodiment of the present application, at least one of the aforementioned R1to R16is an aryl group having a carbon number of 6 to 12 which is substituted with deuterium or is unsubstituted, and the rest are hydrogen or deuterium.

[0180] In one embodiment of the present application, at least one of the aforementioned R1to R16is 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, and the rest are hydrogen or deuterium.

[0181] In one embodiment of the present application, at least one of the aforementioned R1to R16is a phenyl group which is substituted with deuterium or is unsubstituted, or a biphenyl group which is substituted with deuterium or is unsubstituted, and the rest are hydrogen or deuterium.

[0182] In one embodiment of the present application, at least one of the aforementioned R1to R16is a phenyl group which is substituted with deuterium or is unsubstituted, and the rest are hydrogen or deuterium.

[0183] In one embodiment of the present application, the aforementioned R17to R20are 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.

[0184] In one embodiment of the present application, the aforementioned R17to R20are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0185] In one embodiment of the present application, the aforementioned R17to R20are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0186] In one embodiment of the present application, the aforementioned R17to R20are the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

[0187] In one embodiment of the present application, the aforementioned R17to R20are the same as or different from each other, and each is independently hydrogen or deuterium.

[0188] 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.

[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 alkyl group, or a deuterium-substituted or unsubstituted aryl 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 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, or a deuterium-substituted or unsubstituted aryl group.

[0192] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 contains at least one deuterium.

[0193] 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.

[0194] 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.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] 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.

[0199] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 70% or more.

[0200] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 80% or more.

[0201] In one embodiment of the present application, the compound represented by the above Chemical Formula 1 has a deuterium enrichment rate of 90% or more.

[0202] In an embodiment of the present application, the deuterium ratio of the compound represented by Chemical Formula 1 is 100%.

[0203] When the compound represented by Chemical Formula 1 of the present application contains deuterium, the efficiency and the lifespan 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. Thus, 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 lifespan characteristics of the device are improved.

[0204] In an embodiment of the present application, Chemical Formula 1 is a compound represented by any one of Chemical Formulas 1-1 to 1-4 below.

[0205] [Chemical Formula 1-1]

[0206]

[0207] [Chemical Formula 1-2]

[0208]

[0209] [Chemical Formula 1-3]

[0210]

[0211] [Chemical Formula 1-4]

[0212]

[0213] In Chemical Formulas 1-1 to 1-4 above, X1to X3, Ar1, R1to R20, Rb, and q are defined the same as in Chemical Formula 1.

[0214] In an embodiment of the present application, Ra1to Ra3are the same as or different from each other, and each is independently hydrogen or deuterium.

[0215] In an embodiment of the present application, Ra1to Ra3are the same as or different from each other, and each is independently hydrogen, deuterium, an alkyl group substituted with or without deuterium, or an aryl group substituted with or without deuterium.

[0216] In an embodiment of the present application, Ra1to Ra3are the same as or different from each other, and each is independently hydrogen, deuterium, or an aryl group substituted with or without deuterium.

[0217] In an embodiment of the present application, Chemical Formula 1 is any one of the following compounds.

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227] The compound represented by Chemical Formula 1 according to an embodiment of the present specification can be manufactured by the method of the manufacturing 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.

[0228] 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 bandgaps can be synthesized. In addition, 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.

[0229] In addition, the present specification provides an organic light emitting device including the above-mentioned compound.

[0230] 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 an 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.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] According to an embodiment of the present specification, the organic layer includes an electron blocking layer.

[0238] 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.

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

[0242] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer contains the compound.

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

[0244] According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer contains the compound as an n-type 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 contains the compound as an n-type phosphorescent 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 contains the compound as an n-type phosphorescent blue 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 contains the compound as a host, and further contains another host.

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

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

[0250] 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.

[0251] 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.

[0252] According to an embodiment of the present specification, the second host is a carbazole-based compound.

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

[0254] According to an embodiment of the present specification, the light-emitting layer comprises 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.

[0255] According to an embodiment of the present specification, the light-emitting layer comprises 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.

[0256] According to an embodiment of the present specification, the light-emitting layer further comprises a dopant.

[0257] According to an embodiment of the present specification, the light-emitting layer comprises the first host and the second host, and further comprises a dopant.

[0258] According to an embodiment of the present specification, the dopant is a phosphorescent dopant.

[0259] According to an embodiment of the present specification, the dopant comprises 1 to 20 parts by weight with respect to 100 parts by weight of the host.

[0260] According to an embodiment of the present specification, the light-emitting layer comprises a dopant, and the dopant comprises a phosphorescent dopant.

[0261] According to an embodiment of the present specification, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host and a dopant, the host comprises the compound, and the dopant comprises the phosphorescent dopant.

[0262] According to an embodiment of the present specification, the light-emitting layer is a blue light-emitting layer.

[0263] According to an embodiment of the present specification, the light-emitting layer comprises 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, and more specifically, in a weight ratio of 99:1 to 95:5.

[0264] When the light-emitting layer emits red light, as the light-emitting dopant, phosphorescent substances such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum), and the like; or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino) aluminum), and the like, but not limited thereto, can be used. When the light-emitting layer emits green light, as the light-emitting dopant, phosphorescent substances such as Ir(ppy)3 (fac tris(2-phenylpyridine) iridium), and the like; or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino) aluminum), and the like, but not limited thereto, can be used. When the light-emitting layer emits blue light, as the light-emitting dopant, phosphorescent substances such as platinum coordination compounds, (4,6-F2ppy)2Irpic, and the like; or fluorescent substances such as spiro-DPVBi, spiro-6P, DSB (diphenylstyrylbenzene), DSA (diphenylstyrylarylene), PFO-based polymers, PPV-based polymers, and the like, but not limited thereto, can be used.

[0265] According to an embodiment of the present specification, the above-described dopant is a metal coordination compound.

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

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

[0268] According to an embodiment of the present specification, the above-described dopant is the following Chemical Formula D-1 or D-2, but not limited thereto.

[0269] [Chemical Formula D-1]

[0270]

[0271] [Chemical Formula D-2]

[0272]

[0273] In the above Chemical Formulae D-1 and D-2,

[0274] M is a transition metal,

[0275] A1, A3, A5, A6, K1, K2, and K3 are the same as or different from each other, and each independently a direct bond, O, S, a divalent ester group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkenyl group, a substituted or unsubstituted divalent allyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0276] A2and A4are the same as or different from each other, and each independently a direct bond, N, a substituted or unsubstituted trivalent alkylene group, a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heteroaryl group,

[0277] n is 1 or 2, and when n is 2, the structures within the parentheses are the same as or different from each other.

[0278] According to an embodiment of the present specification, the above M is iridium or platinum.

[0279] According to an embodiment of the present specification, the above dopant can be selected from the following structural formula, but is not limited thereto.

[0280]

[0281]

[0282]

[0283]

[0284] 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.

[0285] 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.

[0286] 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 first electrode; an emission layer disposed between the first electrode and the second electrode; and two or more organic layers disposed between the emission layer and the first electrode, or between the emission layer and the second electrode.

[0287] According to an embodiment of the present specification, the two or more organic layers can be selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light 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.

[0288] According to an embodiment of the present specification, the light emitting layer and the first electrode include two or more hole transport layers. The two or more hole transport layers can include the same or different substances from each other.

[0289] According to an embodiment of the present specification, the first electrode is an anode or a cathode.

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

[0291] According to an embodiment of the present specification, the organic light emitting device can be an organic light emitting device of a normal type in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

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

[0293] For example, the structure of the 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 The organic light emitting device is illustrated, and is not limited thereto.

[0294] Figure 1 The structure of the organic light emitting device in which a first electrode 2, a light emitting layer 6, and a second electrode 9 are sequentially stacked on a substrate 1 is illustrated in FIG. 1. The above compound is contained in the light emitting layer.

[0295] Figure 2 The structure of the 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 illustrated in FIG. 2. The above compound is contained in the light emitting layer 6 and / or the hole blocking layer 7.

[0296] The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that the electron injection layer, the electron transport layer, the electron injection and transport layer, the hole blocking layer, and / or the light emitting layer contain the compound of Chemical Formula 1.

[0297] When the organic light emitting device includes a plurality of organic layers, the organic layers can be formed of the same material or different materials.

[0298] 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 material that can be used as a cathode on the organic layer. In addition to this method, the organic light emitting device can be manufactured by sequentially evaporating a cathode material, an organic layer, and an anode material on a substrate.

[0299] In addition, the compound of Chemical Formula 1 above can be used to form an organic layer in the manufacture of 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, etc., but is not limited thereto.

[0300] In addition to these methods, the organic light emitting device can be manufactured by sequentially evaporating a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.

[0301] As the anode material, a material having a large work function is generally preferred in order to enable the smooth injection of holes into the organic layer. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0302] As the cathode material, a material having a small work function is generally preferred in order to enable the easy injection of electrons into the organic layer. For example, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multi-layered structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0303] The light-emitting layer described above can include a host material and a dopant material. According to an embodiment of the present specification, when the organic light-emitting device includes another light-emitting layer in addition to the light-emitting layer including the above-described Chemical Formula 1, the host material is an aromatic condensed ring derivative or a heterocyclic compound, etc.

[0304] Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compound, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but not limited thereto.

[0305] As the dopant material described above, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted aryl amine group, and there are pyrene having an aryl amine group, anthracene, phenanthrene, fluoranthene, etc., but not limited thereto. Indenopyrene, etc. In addition, the styryl amine compound is a compound having at least one aryl vinyl group substituted on a substituted or unsubstituted aryl amine, and is substituted with one or more than two substituents selected from aryl, silyl, alkyl, cycloalkyl, and aryl amine groups, or is unsubstituted. Specifically, there are styryl amine, styryl diamine, styryl triamine, styryl tetramine, etc., but not limited thereto. In addition, as the metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0306] The hole injection layer described above is a layer that receives holes from the electrode. The hole injection material is preferably a material having a capability of transporting holes, having an effect of receiving holes from the anode, and having an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferable to be a material having an excellent capability of preventing excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. In addition, it is preferable to be a material having an excellent thin film formation capability. In addition, it is preferable for the HOMO (highest occupied molecular orbital) of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. As a specific example of the hole injection material, there are metal porphyrin, oligothiophene, aryl amine-based organic matter; hexacarbonitrile hexaazatriphenylene-based organic matter; quinacridone-based organic matter; perylene-based organic matter; anthraquinone, polyaniline, and polythiophene-based conductive polymer, etc., but not limited thereto.

[0307] According to an embodiment of the present specification, the hole injection layer described above includes a compound represented by the following Chemical Formula HI-1, but not limited thereto.

[0308] [Chemical Formula HI-1]

[0309]

[0310] In the above formula HI-1,

[0311] 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 each other to form a substituted or unsubstituted ring,

[0312] r315 is an integer of 1 to 5, and when r315 is 2 or more, two or more of the above R315 are the same as or different from each other,

[0313] r316 is an integer of 1 to 5, and when r316 is 2 or more, two or more of the above R316 are the same as or different from each other.

[0314] According to one embodiment of the present specification, the above 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.

[0315] According to one embodiment of the present specification, the above 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 terphenyl group, and a combination thereof.

[0316] 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 combine with an adjacent group to each other to form an aromatic hydrocarbon ring substituted with an aryl group or an alkyl group.

[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 phenyl group, or a substituted or unsubstituted biphenyl group, or combine with an adjacent group to each other to form a fluorenyl group substituted with or unsubstituted with a phenyl group or a methyl group.

[0318] According to one embodiment of the present specification, the above formula HI-1 is represented by any one of the following compounds.

[0319]

[0320]

[0321] According to one embodiment of the present specification, the above hole injection layer contains a compound represented by the following formula HI-2, but is not limited thereto.

[0322] [Formula HI-2]

[0323]

[0324] In the above formula HI-2,

[0325] R401 to R403 are the same as or different from each other, and each independently a halogen group,

[0326] r401 to r403 are 4.

[0327] According to one embodiment of the present specification, the above R401 to R403 are F.

[0328] According to one embodiment of the present specification, the above formula HI-2 is represented by the following compound.

[0329]

[0330] According to one embodiment of the present specification, the above hole injection layer contains the above formulas HI-1 and HI-2.

[0331] According to one embodiment of the present specification, the above hole injection layer contains the above formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0332] The above hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is preferably a substance having a large mobility for holes. As specific examples, there are arylamine-based organic substances, electrically conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but are not limited thereto.

[0333] According to one embodiment of the present specification, the above hole transport layer contains a compound represented by the above formula HI-1, but is not limited thereto.

[0334] According to one embodiment of the present specification, the above hole injection and transport layer is a layer that transports holes to the light-emitting layer. The substances exemplified in the above hole transport layer and hole injection layer can be used, but are not limited thereto.

[0335] The above-described electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport substance is a substance that can receive electrons from the cathode and transport 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 including Alq3, an organic radical compound, a hydroxyflavone-metal complex, and the like, but are not limited thereto. The electron transport 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, with an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, each with an aluminum layer or a silver layer.

[0336] The above-described electron injection layer is a layer that receives electrons from the electrode. As the electron injection 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 injection effect on the light-emitting layer or the light-emitting material is preferred. Furthermore, a substance that prevents the migration of excitons generated in the light-emitting layer to the hole injection layer and has an excellent film formation ability is preferred. As the above-described electron injection layer substance, specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

[0337] As the above-described metal complex 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-quinolate) chloride, gallium bis(2-methyl-8-quinolate) (o-cresol), aluminum bis(2-methyl-8-quinolate) (o-naphthol), gallium bis(2-methyl-8-quinolate) (2-naphthol), and the like, but are not limited thereto.

[0338] According to an embodiment of the present specification, the above-described electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the above-described 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-described Chemical Formula 1, the substances exemplified in the above-described electron transport layer and electron injection layer can be used, but are not limited thereto.

[0339] According to an embodiment of the present specification, the above-described electron injection and transport layer includes a compound represented by the following Chemical Formula ET-1, but is not limited thereto.

[0340] [Chemical Formula ET-1]

[0341]

[0342] In the above Chemical Formula ET-1,

[0343] at least one of Z11to Z13is N, and the others are CH,

[0344] at least one of Z21to Z23is N, and the others are CH,

[0345] L601and L602are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0346] Ar601to Ar604are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0347] According to an embodiment of the present specification, the above L601and L602are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0348] According to an embodiment of the present specification, the above L601and L602are phenylene.

[0349] According to an embodiment of the present specification, the above Ar601to Ar604are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0350] According to an embodiment of the present specification, the above Ar601to Ar604are phenyl.

[0351] According to an embodiment of the present specification, the above Chemical Formula ET-1 is represented by the following compound.

[0352]

[0353] 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.

[0354] The electron-blocking layer is a layer that prevents electrons injected from the electron-injection layer from passing through the light-emitting layer to enter the hole-injection layer, and thus can improve the lifespan and efficiency of the device. In the case where the electron-blocking layer includes another electron-blocking layer in addition to the electron-blocking layer including the compound according to the embodiment of the present specification, a known material can be used without limitation, and the substances exemplified in the description of the hole-injection layer can be used, but are not limited thereto. The 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 that simultaneously performs hole injection and hole transport.

[0355] The hole-blocking layer is a layer that blocks holes from reaching the cathode, and can be formed under the same conditions as the electron-injection layer. Specifically, there are aluminum complexes, but are not limited thereto.

[0356] According to the embodiment of the present specification, in the case where the organic light-emitting device includes a hole-blocking layer in addition to the hole-blocking layer including the compound of the above chemical formula 1, the substances exemplified in the hole-blocking layer can be used, but are not limited thereto.

[0357] For example, the hole-blocking layer includes a compound represented by the following chemical formula HB-1, but is not limited thereto.

[0358] [Chemical Formula HB-1]

[0359]

[0360] In the above HB-1,

[0361] at least one of Q1 to Q3 is N, and the others are CH,

[0362] L701 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0363] T1 to T3 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0364] According to the embodiment of the present specification, Q1 to Q3 are N.

[0365] According to the embodiment of the present specification, L701 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0366] According to the embodiment of the present specification, L701 is a direct bond or an arylene group.

[0367] According to an embodiment of the present specification, the above L701 is a direct bond, or an arylene group having 6 to 30 carbon atoms.

[0368] According to an embodiment of the present specification, the above L701 is a direct bond or a phenylene group.

[0369] According to an embodiment of the present specification, the above T1 to T3 are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group.

[0370] According to an embodiment of the present specification, the above T1 to T3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0371] According to an embodiment of the present specification, the above T1 to T3 are the same as or different from each other, and each independently a heteroaryl group.

[0372] According to an embodiment of the present specification, the above T1 to T3 are the same as or different from each other, and each independently a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0373] According to an embodiment of the present specification, the above T1 to T3 are a carbazolyl group.

[0374] According to an embodiment of the present specification, the above Chemical Formula HB-1 can include, but is not limited to, the following compounds.

[0375]

[0376] According to an embodiment of the present specification, the above Chemical Formula HB-1 can also be used as a first host material of the light-emitting layer.

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

[0378] The organic light-emitting device according to the present specification can be a top emission type, a bottom emission type, or a dual emission type, depending on the materials used.

[0379] The organic light-emitting device according to the present specification can be used in various electronic devices. For example, the above electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., and is not limited thereto.

[0380] Hereinafter, examples and comparative examples will be cited to explain the present specification in detail. However, the examples and comparative examples according to the present specification can be modified in various different forms, and are not construed as limiting the scope of the present specification to the examples and comparative examples detailed below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those skilled in the art.

[0381] [Manufacturing Example]

[0382] [Manufacturing Example 1] Synthesis of Compound 1

[0383]

[0384] After 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (6.50 g, 14.57 mmol) and compound a-2 (5.82 g, 16.03 mmol) were completely dissolved in 240 mL of tetrahydrofuran (THF) in a 500 mL round-bottom flask under a nitrogen atmosphere, 2 M of a potassium carbonate aqueous solution (120 mL) was added, and then tetrakis(triphenylphosphine)palladium (0.51 g, 0.44 mmol) was added, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure, and recrystallized with 210 mL of ethyl acetate, thereby manufacturing compound 2 (6.14 g, 58%).

[0385] MS [M+H] + = 729

[0386] [Manufacturing Example 2] Synthesis of Compound 2

[0387]

[0388] After 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (6.50 g, 14.57 mmol) and compound a-2 (5.82 g, 16.03 mmol) were completely dissolved in 240 mL of tetrahydrofuran (THF) in a 500 mL round-bottom flask under a nitrogen atmosphere, 2 M of a potassium carbonate aqueous solution (120 mL) was added, and then tetrakis(triphenylphosphine)palladium (0.51 g, 0.44 mmol) was added, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure, and recrystallized with 210 mL of ethyl acetate, thereby manufacturing compound 2 (6.14 g, 58%).

[0389] MS [M+H]+ =729

[0390] <Production Example 3> Synthesis of Compound 3

[0391]

[0392] Under a nitrogen atmosphere, compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (6.50 g, 14.57 mmol) and compound a-3 (5.82 g, 16.03 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask. A 2M aqueous potassium carbonate solution (120 mL) was then added, followed by tetrakis(triphenylphosphine)palladium (0.43 g, 0.37 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 330 mL of ethyl acetate to produce compound 3 (6.51 g, 61%).

[0393] MS[M+H] + =729

[0394] <Production Example 4> Synthesis of Compound 4

[0395]

[0396] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, 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 (3.13 g, 8.33 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then a 2M aqueous potassium carbonate solution (120 ml) was added. After adding tetrakis(triphenylphosphine)palladium (0.26 g, 0.23 mmol), the mixture was heated with stirring for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 340 mL of ethyl acetate to produce Compound 4 (3.45 g, 60%).

[0397] MS[M+H] + =762

[0398] <Production Example 5> Synthesis of Compound 5

[0399]

[0400] 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 (3.13 g, 8.33 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 2 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 350 mL of ethyl acetate, thereby producing compound 5 (4.11 g, 71%).

[0401] MS [M+H] + = 762

[0402] <Manufacturing Example 6> Synthesis of compound 6

[0403]

[0404] 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-6 (3.13 g, 8.33 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 3 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 310 mL of ethyl acetate, thereby producing compound 6 (3.77 g, 65%).

[0405] MS [M+H] + = 762

[0406] <Manufacturing Example 7> Synthesis of compound 7

[0407]

[0408] Under a nitrogen atmosphere, in a 500 ml round-bottom flask, the compounds 9-(4-(9H-carbazol-9-yl)-6-chloro-1,3,5-triazin-2-yl)-4-phenyl-9H-carbazole (9-(4-(9H-carbazol-9-yl)-6-chloro-1,3,5-triazin-2-yl)-4-phenyl-9H-carbazole) (4.50 g, 8.62 mmol) and a-3 (3.60 g, 9.91 mmol) were completely dissolved in 240 ml of tetrahydrofuran (THF), and then a 2M aqueous potassium carbonate solution (120 ml) was added. After adding tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.30 g, 0.26 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 240 ml of ethyl acetate to produce Compound 7 (4.88 g, 70%).

[0409] MS[M+H] + =805

[0410] <Production Example 8> Synthesis of Compound 8

[0411]

[0412] Under a nitrogen atmosphere, in a 500ml round-bottom flask, compounds 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (4.50g, 10.09mmol) and a-7 (5.09g, 11.60mmol) were completely dissolved in 240ml of tetrahydrofuran (THF). A 2M aqueous potassium carbonate solution (120ml) was then added, followed by the addition of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.35g, 0.30mmol), and the mixture was heated and stirred for 7 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 240ml of ethyl acetate to produce compound 8 (5.64g, 69%).

[0413] MS[M+H] + =805

[0414] [Example]

[0415] Example 1-1

[0416] ITO (indium tin oxide) is used to The glass substrate coated with a film of a thickness of 1000 nm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used was a Fischer Co. product, and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol and dried, and then the substrate was transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum deposition machine.

[0417] 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 BH (p-type) compound was vacuum-deposited to form an electron blocking layer. Next, on the electron blocking layer, a mixture of the following chemical formula BH (p-type), i.e., the p-type host of the light-emitting layer, and the compound 1 synthesized in the above-mentioned manufacturing example 1, i.e., the n-type host of the light-emitting layer, was mixed in a weight ratio of 1:1, and a compound represented by the following chemical formula BD was vacuum-deposited in a weight ratio of 88:12, thereby forming a light-emitting layer. On the above-mentioned light-emitting layer, a film thickness of The compound represented by the following chemical formula HB1 was vacuum-deposited to form a hole blocking layer. Next, the compound represented by the following chemical formula ET1 and the compound represented by the following chemical formula LiQ were vacuum-deposited on the hole blocking layer at a weight ratio of 1:1, thereby forming a hole blocking layer. The electron injection and transport layer is formed with a thickness of The thickness of the aluminum A thickness of 1000 nm is evaporated to form a cathode.

[0418]

[0419] In the above process, the evaporation rate of organic matter is maintained at Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 ~5×10 -6 The organic light-emitting device is thus produced.

[0420] Examples 1-2 to 1-8

[0421] An organic light emitting device was produced by the same method as described in Example 1-1, except that the compound described in Table 1 below was used instead of the compound of Production Example 1.

[0422] [Comparative Example]

[0423] Comparative Examples 1-1 to 1-8

[0424] An organic light emitting device was produced by the same method as described in Example 1-1, except that the compound described in Table 1 below was used instead of the compound of Production Example 1. The compounds of BH1(n-type) to BH8(n-type) used in Table 1 below are shown below.

[0425]

[0426] [Experimental Example]

[0427] When a current was applied to the organic light emitting devices produced in Examples 1-1 to 1-8 and Comparative Examples 1-1 to 1-8 described above, the voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in Table 1 below.

[0428] T95 means the time required for the luminance to decrease to 95% from the initial luminance (1600 nits).

[0429] [Table 1]

[0430]

[0431] As shown in Table 1 above, the organic light emitting devices of Examples 1-1 to 1-8 using the compound of Formula 1 according to one embodiment of the present specification in which a carbazole substituted with an aryl group is connected to a triazine nucleus with a m-phenylene group as a connecting group directly on the triazine showed excellent characteristics in terms of the efficiency, driving voltage, and stability of the organic light emitting device.

[0432] Specifically, Examples 1-1 to 1-8 containing the compound of Formula 1 according to one embodiment of the present specification showed excellent characteristics in terms of the efficiency, driving voltage, and stability compared to Comparative Example 1-1 containing the compound BH1 having no substituent of a carbazolyl group connected by a connecting group, Comparative Examples 1-2 and 1-3 containing the compounds BH2 and BH3 in which the connecting group is a p-phenylene group, Comparative Example 1-4 containing the compound BH4 in which three carbazoles are directly connected on a triazine, and Comparative Examples 1-5 to 1-8 containing the compounds BH5 to BH8 in which the connecting position of a carbazole directly connected to a triazine is different from the present application or one carbazole is directly connected on a triazine.

[0433] The preferred embodiments of the present application have been described above with reference to the accompanying drawings, whilst the present application is not limited to the above examples, but can be variously changed within the scope of the present application claimed and the scope of the detailed description of the present application, and it also belongs to the scope of the present application.

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 Chemical Formula 1, and Ra1 to Ra3 are 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### a compound represented by the following Chemical Formula 61: [Chemical Formula 61] ###0065### a compound represented by the following Chemical Formula 62: [Chemical Formula 62] ###0066### 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 11, 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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