NOVEL COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING THE SAME

Abstract

The present invention relates to a novel compound and an organic light-emitting device containing the same.

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0149074 dated November 9, 2022 and Korean Patent Application No. 10-2023-0150901 dated November 3, 2023, and all contents disclosed in the documents of said Korean patent applications are incorporated herein by reference.

[0002] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Background technology]

[0003] In general, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and are the subject of much research.

[0004] An organic light emitting device generally has a structure including a positive electrode, a negative electrode, and an organic material layer between the positive electrode and the negative electrode. The organic material layer is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic material layer, and when the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0005] There is a continuous demand for the development of new organic materials for use in the organic light emitting devices. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention relates to a novel organic light-emitting material and an organic light-emitting device containing the same. [Means for solving the problem]

[0008] The present invention provides a compound represented by the following formula 1: [ka]

[0009] In the above Chemical Formula 1, Ar1 and Ar2 each independently represent a substituted or unsubstituted C 6-60 aryl; or C containing one or more selected from the group consisting of substituted or unsubstituted N, O and S 2-60 is heteroaryl, Ar3 is a substituted or unsubstituted C 6-60 is aryl, L is a single bond; substituted or unsubstituted C 6-60 arylene; or C containing one or more selected from the group consisting of substituted or unsubstituted N, O and S 2-60 is heteroarylene, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-60 aryl, wherein any one of R1 to R8 is a substituted or unsubstituted phenyl, and any one or more of the remaining are deuterium; R9 is hydrogen or deuterium; n is an integer from 1 to 3.

[0010] The present invention also provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. Effect of the Invention

[0011] The compound represented by Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can improve the efficiency, reduce the driving voltage, and / or improve the life characteristics of the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a light-emitting material. [Brief description of the drawings]

[0012] [Figure 1] An example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3 and a negative electrode 4 is shown. [Diagram 2] 1 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, an emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The present invention will now be described in more detail for a better understanding.

[0014] The present invention provides a compound represented by Chemical Formula 1. In this specification, [ka] or [ka] denotes a bond that is connected to another substituent.

[0015] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthiooxy group; arylthiooxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heteroaryl group containing one or more of N, O and S atoms, or that the group is substituted or unsubstituted with two or more of the above-mentioned exemplary substituents connected. For example, the "substituent having two or more substituents connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent having two phenyl groups connected.

[0016] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the substituent has the following structure, but is not limited thereto. [ka]

[0017] In this specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may be one of the following structural formulas, but is not limited thereto. [ka]

[0018] In this specification, the number of carbon atoms of the imido group is not particularly limited, but is preferably 1 to 25. Specifically, the imido group may have a substituent having the following structure, but is not limited thereto. [ka]

[0019] In this specification, the silyl group may specifically be a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, or the like, but is not limited thereto.

[0020] In this specification, the boron group may specifically be, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, or the like.

[0021] In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0022] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0023] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited to these.

[0024] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0025] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, or a fluorenyl group, but is not limited thereto.

[0026] In the present specification, the fluorenyl group may be substituted, and two of the substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to this.

[0027] In the present specification, the heteroaryl group is a heteroaryl group containing one or more hetero elements selected from the group consisting of O, N, Si, and S, and is not particularly limited in number of carbon atoms, but preferably has 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidine, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazoleyl, phenothiazinyl, and dibenzofuranyl groups.

[0028] In this specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-mentioned aryl group examples. In this specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the above-mentioned alkyl group examples. In this specification, the heteroaryl in the heteroarylamine can be applied to the above-mentioned heteroaryl group. In this specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group examples. In this specification, the aryl group described above can be applied to the arylene, except that it is a divalent group. In this specification, the heteroaryl group described above can be applied to the heteroarylene, except that it is a divalent group. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by bonding two substituents, but the above-mentioned explanation of the aryl group or cycloalkyl group can be applied. In this specification, the heteroaryl is not a monovalent group, but is formed by bonding two substituents, but the above-mentioned explanation of the heteroaryl group can be applied.

[0029] Preferably, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-20 aryl; or C containing one or more selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It may be a heteroaryl.

[0030] More preferably, Ar1 and Ar2 may each independently be phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and said Ar1 and Ar2 may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0031] Most preferably, Ar1 and Ar2 may each independently be any one selected from the group consisting of: [ka]

[0032] Preferably, Ar3 is a substituted or unsubstituted C 6-20 It may be aryl.

[0033] More preferably, Ar3 may be phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; or biphenylyl which is unsubstituted or substituted with 1 to 9 deuteriums.

[0034] More preferably, Ar3 may be phenyl, phenyl substituted with five deuteriums, biphenylyl, or biphenylyl substituted with nine deuteriums.

[0035] Preferably, L is a single bond; substituted or unsubstituted C 6-20 arylene; or C containing one or more selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It may be a heteroarylene.

[0036] More preferably, L may be a single bond.

[0037] Preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20 In the aryl group, any one of R1 to R8 may be a substituted or unsubstituted phenyl, and any one or more of the remaining may be deuterium.

[0038] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20 In the aryl group, any one of R1 to R8 is unsubstituted or phenyl substituted with 1 to 5 deuterium atoms, and any one or more of the remaining groups may be deuterium.

[0039] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted phenyl, provided that any one of R1 to R8 is unsubstituted or phenyl substituted with 1 to 5 deuterium atoms, and any one or more of the remaining may be deuterium.

[0040] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20 In the aryl group, any one of R1 to R8 is phenyl or phenyl substituted with five deuterium atoms, and any one or more of the remaining may be deuterium.

[0041] More preferably, R1 to R8 are each independently hydrogen; deuterium; or substituted or unsubstituted phenyl, provided that any one of R1 to R8 is phenyl or phenyl substituted with five deuterium atoms, and any one or more of the remaining may be deuterium.

[0042] Most preferably, any one of R1 to R8 is phenyl or phenyl substituted with five deuterium atoms, and the remainder may be deuterium.

[0043] Preferably, R1 is phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and one or more of R2 to R8 are deuterium; R2 is phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and one or more of R1 and R3 to R8 are deuterium; R3 is phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and one or more of R1, R2, and R4 through R8 are deuterium; or R4 may be phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and one or more of R1 to R3 and R5 to R8 may be deuterium.

[0044] More preferably, R1 is phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and R2 to R8 are deuterium; R2 is phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and R1 and R3 to R8 are deuterium; R3 is phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and R1, R2 and R4-R8 are deuterium; or R4 may be phenyl that is unsubstituted or substituted with 1 to 5 deuterium atoms, and R1 to R3 and R5 to R8 are deuterium.

[0045] Most preferably, R1 is phenyl that is unsubstituted or substituted with 5 deuteriums, and R2-R8 are deuterium; R2 is unsubstituted or phenyl substituted with 5 deuteriums, and R1 and R3-R8 are deuterium; R3 is unsubstituted or substituted with 5 deuteriums, and R1, R2 and R4-R8 are deuterium; or R4 may be phenyl that is unsubstituted or substituted with five deuterium atoms, and R1-R3 and R5-R8 may be deuterium.

[0046] Representative examples of the compound represented by Formula 1 are as follows:

[0047] [ka]

[0048] [ka]

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] The compound represented by Chemical Formula 1 can be prepared, for example, by the method shown in Reaction Scheme 1 below, and the remaining compounds can be prepared in a similar manner. [ka]

[0058] In the reaction formula 1, Ar1 to Ar3, L, R1 to R9 and n are the same as defined in the chemical formula 1, and X is a halogen, preferably, X is fluorine, chloro or bromo.

[0059] The reaction scheme 1 is preferably carried out in the presence of a palladium catalyst and a base as an amine substitution reaction, and the reactive group for the amine substitution reaction can be changed as known in the art. The preparation method can be more specifically described in the preparation examples described below.

[0060] The present invention also provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. As an example, the present invention provides an organic light-emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1.

[0061] The organic layer of the organic light-emitting device of the present invention may have a layered structure, but may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0062] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1.

[0063] In addition, the organic layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes, and the hole transport layer, the hole injection layer, or the layer that simultaneously transports and injects holes may include a compound represented by Chemical Formula 1.

[0064] In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.

[0065] The organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate. The organic light-emitting device according to the present invention may be an organic light-emitting device having an inverted structure (inverted type) in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIG. 1 and FIG. 2.

[0066] Fig. 1 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, an emitting layer 3, and a negative electrode 4. Fig. 2 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, an emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in the compound layer.

[0067] The organic light emitting device according to the present invention is manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0068] For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a cathode, and an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and a material that can be used as an anode may be deposited thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an anode material, an organic layer, and an anode material on a substrate.

[0069] In addition, the compound represented by Formula 1 can be formed as an organic layer by a solution coating method as well as a vacuum deposition method during the manufacture of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spraying, roll coating, etc.

[0070] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (WO2003 / 012890), but the manufacturing method is not limited to this.

[0071] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0072] The cathode material is preferably a material having a large work function so that holes can be easily injected into the organic layer.Specific examples of the cathode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0073] The negative electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0074] The hole injection layer is a layer that injects holes from the electrode. The hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the positive electrode, has an excellent hole injection effect on the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

[0075] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and move them to the light emitting layer, and is suitable for use as a material with high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers that have both conjugated and non-conjugated parts. For example, when two or more types of hole transport materials are used, they can be mixed and used, or the first, second, or more hole transport layers can be manufactured without mixing them.

[0076] The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the anode from being recombined in the light emitting layer and passing to the hole transport layer, and is also called an electron inhibiting layer. The electron blocking layer is preferably made of a material having a smaller electron affinity than the electron transport layer.

[0077] The light-emitting material is preferably a material that can emit light in the visible light range by transporting and combining holes and electrons from the hole transport layer and electron transport layer, and has good quantum efficiency for fluorescence and phosphorescence.Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzothiazole and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, etc.

[0078] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the fused aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocyclic ring-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc. Preferably, the compound represented by Chemical Formula 1 may be used as a host. The compound represented by Chemical Formula 1 may be used as a co-host together with another host material.

[0079] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periflanthene, which have arylamino groups, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the dopant materials include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0080] The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the positive electrode from passing to the electron transport layer without being recombined in the light emitting layer, and is also called a hole suppression layer. As the hole blocking layer, a material having a large ionization energy is preferable.

[0081] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As the electron transport material, a material that can receive electrons from the negative electrode well and transfer them to the light-emitting layer and has high mobility for electrons is suitable. Specific examples include, but are not limited to, Al complex of 8-hydroxyquinoline; complex containing Alq3; organic radical compound; hydroxyflavone-metal complex. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specific examples are cesium, barium, calcium, ytterbium, and samarium, each of which is followed by an aluminum or silver layer.

[0082] The electron injection layer is a layer that injects electrons from an electrode, and is capable of transporting electrons, has an excellent electron injection effect from a negative electrode, an excellent electron injection effect for the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound with excellent thin-film forming ability.Specific examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0083] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0084] Meanwhile, in the present invention, the "electron injection and transport layer" is a layer that serves as both the electron injection layer and the electron transport layer, and may be made of a material that serves as each of the layers, either alone or in combination, but is not limited thereto.

[0085] The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a dual emission device, and may be a bottom emission device which is particularly required to have a relatively high light emitting efficiency.

[0086] In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

[0087] The present invention will be described in more detail below to help understanding of the present invention. However, the following examples are merely illustrative of the present invention, and the content of the present invention is not limited to the following examples. EXAMPLES

[0088] [Production Example] Preparation Example 1: Preparation of Compound GH1 [ka]

[0089] (Production Example 1-1) Production of Compound 1(a) P-1 Under a nitrogen atmosphere, 1-bromo-9H-carbazole (50 g, 203.2 mmol) and TfOH (10 ml) were added to C6D6 (500 ml) and stirred at 40 degrees for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, D2O (100 ml) was added, and the mixture was stirred for 30 minutes, after which trimethylamine (12 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4 and recrystallized from ethanol to obtain 44.5 g of compound 1(a)P-1. (Yield 87%, MS [M+H] + =254)

[0090] (Production Example 1-2) Production of Compound 1(a) In a nitrogen atmosphere, compound 1(a) P-1 (30 g, 118.5 mmol) and phenylboronic acid (14.4 g, 118.5 mmol) were added to 600 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (49.1 g, 355.5 mmol) was dissolved in 49 ml of water and added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (4.1 g, 3.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered off. The solid was dissolved in 1483 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound 1(a) (21.4 g, 72%, MS: [M+H] + =251.4).

[0091] [ka]

[0092] (Production Example 1-3) Production of Compound GH1P-1 Under a nitrogen atmosphere, 2-([1,1'-biphenyl]-3-yl)-4-3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine (30g, 68.5mmol) and (phenyl-d5)boronic acid (8.7g, 68.5mmol) were added to 600ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (28.4g, 205.5mmol) was dissolved in 28ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (2.4g, 2.1mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered off. The solid was dissolved in 1660mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to give a white solid compound GH1P-1 (22.9 g, 69%, MS: [M+H] + =485.6) was produced.

[0093] (Production Example 1-4) Production of Compound GH1 Under a nitrogen atmosphere, GH1P-1 (30 g, 61.9 mmol) and 1(a) (15.5 g, 61.9 mmol) were added to 600 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (25.7 g, 185.7 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (2.1 g, 1.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature and the resulting solid was filtered off. The solid was dissolved in 2213 mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound GH1 (26.1 g, 59%, MS: [M+H] + =715.9) was produced.

[0094] Preparation Example 2: Preparation of Compound GH2 [ka]

[0095] (Production Example 2-1) Production of Compound 2(a) A white solid compound 2(a) (22.4 g, 74%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-2, except that (phenyl-d5)boronic acid was used instead of phenylboronic acid. + =256.4).

[0096] [ka]

[0097] (Production Example 2-2) Production of Compound GH2P-1 A white solid compound GH2P-1 (25.2 g, 77%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-3, except that 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine and (phenyl-d5)boronic acid were used instead of (phenyl-d5)boronic acid. + =494.5) was produced.

[0098] (Production Example 2-3) Production of Compound GH2 A yellow solid compound GH2 (29.7 g, 67%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH2P-1 was used instead of compound GH1P-1 and compound 2(a) was used instead of compound 1(a). + =729.9).

[0099] Preparation Example 3: Preparation of Compound GH3

[0100] [ka]

[0101] (Preparation Example 3-1) Preparation of Compound 3(a) P-1 A white solid compound 3(a)P-1 (42.5 g, yield 83%, MS [M+H]) was obtained in the same manner as in Preparation Example 1-1, except that 2-bromo-9H-carbazole was used instead of 1-bromo-9H-carbazole. + =254) was produced.

[0102] (Production Example 3-2) Production of Compound 3(a) A white solid compound 3(a) (20.6 g, 68%, MS: [M+H]) was obtained in the same manner as in Preparation Example 2-2, except that compound 3(a) P-1 was used instead of compound 2(a) P-1.+ =256.4).

[0103] [ka]

[0104] (Production Example 3-3) Production of Compound GH3P-1 A white solid compound GH3P-1 (16.2 g, 66%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-3, except that 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine. + =404.5) was produced.

[0105] (Production Example 3-4) Production of Compound GH3 A yellow solid compound GH3 (28 g, 59%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH3P-1 was used instead of compound GH1P-1 and compound 3(a) was used instead of compound 1(a). + =639.8) was produced.

[0106] Production Example 4: Production of Compound GH4 [ka]

[0107] (Production Example 4-1) Production of Compound 4(a) A white solid compound 4(a) (23.4 g, 79%, MS: [M+H]) was obtained in the same manner as in Preparation 3-2, except that phenylboronic acid was used instead of (phenyl-d5)boronic acid. + =251.4).

[0108] [ka]

[0109] (Production Example 4-2) Production of Compound GH4P-1 A white solid compound GH4P-1 (26.4 g, 80%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-3, except that 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine and phenylboronic acid was used instead of (phenyl-d5)boronic acid. + =515.6) was produced.

[0110] (Production Example 4-3) Production of Compound GH4 A yellow solid compound GH4 (28.7 g, 66%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH4P-1 was used instead of compound GH1P-1 and compound 4(a) was used instead of compound 1(a). + =746) was manufactured.

[0111] Preparation Example 5: Preparation of Compound GH5 [ka]

[0112] (Preparation Example 5-1) Preparation of Compound 5(a) P-1 A white solid compound 3(a)P-1 (46.1 g, yield 90%, MS [M+H]) was obtained in the same manner as in Preparation Example 1-1, except that 3-bromo-9H-carbazole was used instead of 1-bromo-9H-carbazole. + =254) was produced.

[0113] (Production Example 5-2) Production of Compound 5(a) A white solid compound 5(a) (21.8 g, 72%, MS: [M+H]) was obtained in the same manner as in Preparation Example 2-2, except that compound 5(a)P-1 was used instead of compound 2(a)P-1. + =256.4).

[0114] [ka]

[0115] (Production Example 5-3) Production of Compound GH5P-1 A white solid compound GH5P-1 (23 g, 68%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-3, except that 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine. + =409.5).

[0116] (Production Example 5-4) Production of Compound GH5 A yellow solid compound GH5 (24.1 g, 51%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH5P-1 was used instead of compound GH1P-1 and compound 5(a) was used instead of compound 1(a). + =644.9) was produced.

[0117] Preparation Example 6: Preparation of Compound GH6 [ka]

[0118] (Production Example 6-1) Production of Compound GH6P-1 A white solid compound GH6P-1 (21.2 g, 64%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-3, except that 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazine. + =485.6) was produced.

[0119] (Production Example 6-2) Production of Compound GH6 A yellow solid compound GH6 (24.8 g, 56%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH6P-1 was used instead of compound GH1P-1 and compound 6(a) was used instead of compound 1(a). + =715.9) was produced.

[0120] (Production Example 7) Production of Compound GH7 [ka]

[0121] (Production Example 7-1) Production of Compound GH7P-1 A white solid compound GH7P-1 (27.8 g, 70%, MS: [M+H]) was obtained in the same manner as in Preparation Example 5-3, except that 4-bromo-1,1'-biphenyl was used instead of (phenyl-d5)boronic acid. + =480.6) was produced.

[0122] (Production Example 7-2) Production of Compound GH7 A yellow solid compound GH6 (23.7 g, 53%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH7P-1 was used instead of compound GH1P-1 and compound 5(a) was used instead of compound 1(a). + =715.9) was produced.

[0123] (Production Example 8) Production of Compound GH8 [ka]

[0124] (Production Example 8-1) Production of Compound GH8P-1 A white solid compound GH8P-1 (22.2 g, 67%, MS: [M+H]) was obtained in the same manner as in Preparation Example 5-3, except that 9-(4-(3-chloro-4-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole was used instead of 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine. + =498.6) was produced.

[0125] (Production Example 8-2) Production of Compound GH8 A yellow solid compound GH8 (22.5 g, 51%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-4, except that compound GH8P-1 was used instead of compound GH1P-1 and compound 5(a) was used instead of compound 1(a). + =734) was manufactured.

[0126] Preparation Example 9: Preparation of Compound GH9 [ka]

[0127] (Preparation Example 9-1) Preparation of Compound 9(a) P-1 A white solid compound 9(a)P-1 (43.9 g, 86% yield, MS [M+H]) was obtained in the same manner as in Preparation Example 1-1, except that 4-bromo-9H-carbazole was used instead of 1-bromo-9H-carbazole. + =254) was produced.

[0128] (Production Example 9-2) Production of Compound 9(a) A white solid compound 9(a) (20.5 g, 69%, MS: [M+H]) was obtained in the same manner as in Preparation Example 2-2, except that compound 9(a)P-1 was used instead of compound 1(a)P-1 and phenylboronic acid was used instead of (phenyl-d5)boronic acid. + =251.4).

[0129] [ka]

[0130] (Production Example 9-3) Production of Compound GH9 A yellow solid compound GH9 (24 g, 51%, MS: [M+H]) was obtained in the same manner as in Preparation Example 3-4, except that compound 9(a) was used instead of compound 3(a). + =634.8) was produced.

[0131] Preparation Example 10: Preparation of Compound GH10 [ka]

[0132] (Preparation Example 10-1) Preparation of Compound 10(a) A white solid compound 10(a) (21.5 g, 71%, MS: [M+H]) was obtained in the same manner as in Preparation Example 9-1, except that (phenyl-d5)boronic acid was used instead of phenylboronic acid. + =256.4). [ka]

[0133] (Production Example 10-2) Production of Compound GH10P-1 A white solid compound GH10P-1 (24.2 g, 74%, MS: [M+H]) was obtained in the same manner as in Preparation 3-3, except that 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine. + =494.5) was produced.

[0134] (Production Example 10-3) Production of Compound GH10 A yellow solid compound GH10 (27.5 g, 62%, MS: [M+H]) was obtained in the same manner as in Preparation Example 3-4, except that compound 10(a) was used instead of compound 3(a) and compound GH10P-1 was used instead of compound GH3P-1. + =729.9).

[0135] [Example] Example 1 A glass substrate coated with a 100 nm-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water containing detergent. The detergent used was made by Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was washed for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition device.

[0136] On the thus prepared ITO transparent electrode, the following compound HI-A was thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer.

[0137] The following compound HAT was vacuum-deposited on the hole injection layer to form a first hole transport layer having a thickness of 5 nm, and the following compound HT-A was vacuum-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 50 nm.

[0138] On the hole transport layer, the following compound HT-B was thermally vacuum deposited to a thickness of 45 nm to form an electron blocking layer. On the electron blocking layer, the previously prepared compound GH1 was mixed with the following compound GH-H in a weight ratio of 1:1, and then the compound was vacuum deposited with the following compound GD in a weight ratio of 90:10 to a thickness of 40 nm to form a light emitting layer. On the light emitting layer, the following compound ET-A was vacuum deposited to a thickness of 5 nm to form a hole blocking layer. On the hole blocking layer, the following compound ET-B and the following compound LiQ were vacuum deposited in a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 35 nm.

[0139] Lithium fluoride (LiF) was deposited on the electron injection and transport layer to a thickness of 1 nm, and then aluminum was deposited to a thickness of 100 nm to form a negative electrode, thereby preparing an organic light emitting device.

[0140] [ka]

[0141] During the above process, the deposition rate of the organic material was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The degree of vacuum during deposition was 1×10 -7 torr~5×10 -5 torr was maintained.

[0142] (Examples 2 to 10 and Comparative Examples 1 to 6) An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1.

[0143] In Table 1 below, the structures of compounds GHA to GHF are as follows, respectively. [ka]

[0144] [Experimental Example] A current was applied to the organic light emitting devices fabricated in Examples 1 to 10 and Comparative Examples 1 to 6, and the voltage, efficiency, luminous color, and lifespan (T95) were measured. The results are shown in Table 1 below. At this time, the voltage and efficiency were 10 mA / cm 2 The T95 value was measured at a current density of 20 mA / cm. 2 means the time (hr) until the initial brightness drops to 95%.

[0145] [Table 1]

[0146] The compound represented by Chemical Formula 1 of the present invention is designed to induce steric hindrance by introducing a substituted / unsubstituted phenyl group into the Ar3 position, and to have a twisted structure between the triazine portion and the carbazole portion. In this case, the electron donating property of the carbazole substituent acts to increase the stability of the whole molecule, and the electron distribution is separated, resulting in additional CT (charge transfer) properties, which can lead to improved voltage / efficiency characteristics.

[0147] However, in this case, there is a high possibility that problems with molecular stability may occur due to the electron deficiency phenomenon of the carbazole substituent. To solve this, it was confirmed that by substituting deuterium into the carbazole substituent, the lifetime increase effect is significantly greater than that of other parts. In addition, the introduction of an additional phenyl group was able to adjust the electron distribution and balance, leading to improvements in efficiency / lifetime.

[0148] In Comparative Example 1, there was no substituent at the Ar3 position of Chemical Formula 1, and therefore the overall molecular structure was flat, and therefore it was confirmed that the above-mentioned effect could not be achieved. In Comparative Example 4, the position of the phenyl group was different, and in this case, sufficient steric hindrance was not generated, and sufficient improvement effect could not be achieved. In Comparative Example 5, it was confirmed that the electron-donating role of the carbazole substituent was not fully achieved due to the substitution of an additional carbazole group on the carbazole group, leading to a decrease in efficiency and lifespan. When a heterocycle such as a carbazole group is additionally substituted on the carbazole, it directly affects the electronic properties of the original carbazole substituent, and when applied to an organic light-emitting device, it shows inferior physical properties. In Comparative Example 6, a fluorene substituent was introduced, but it was confirmed that not only was sufficient steric hindrance not provided to the carbazole group, but the stability of the fluorene substituent was reduced, causing a rapid decrease in lifespan. [Explanation of symbols]

[0149] 1: Substrate 2: Positive electrode 3: Light-emitting layer 4: Negative electrode 5: Hole injection layer 6: First hole transport layer 7: Second hole transport layer 8: Electron blocking layer 9: Hole blocking layer 10: Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, Ar １ and Ar ２ each independently represents a substituted or unsubstituted C ６－６０ aryl; or C containing one or more selected from the group consisting of substituted or unsubstituted N, O and S ２－６０ is heteroaryl, Ar ３ is a substituted or unsubstituted C ６－６０ is aryl, L is a single bond; ６－６０ arylene; or C containing one or more selected from the group consisting of substituted or unsubstituted N, O and S. ２－６０ Heteroarylene, R １ ~R ８ are each independently hydrogen; deuterium; or substituted or unsubstituted C ６－６０ aryl, R １ ~R ８ is a substituted or unsubstituted phenyl, and one or more of the remaining are deuterium; R ９ is hydrogen or deuterium, n is an integer from 1 to 3.

2. Ar １ and Ar ２ are each independently phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; The Ar １ and Ar ２ 11. The compound of claim 1, wherein each is independently unsubstituted or substituted with one or more deuterium atoms.

3. Ar １ and Ar ２ is independently any one selected from the group consisting of: 【Chemistry 2】

4. Ar ３ The compound of claim 1, wherein is phenyl which is unsubstituted or substituted with 1 to 5 deuteriums; or biphenylyl which is unsubstituted or substituted with 1 to 9 deuteriums.

5. The compound of claim 1 , wherein L is a single bond.

6. R １ ~R ８ are each independently hydrogen; deuterium; or substituted or unsubstituted C ６－２０ is an aryl of R １ ~R ８ The compound according to claim 1, wherein any one of is unsubstituted or substituted with 1 to 5 deuterium atoms, and any one or more of the remaining is deuterium.

7. R １ ~R ８ 2. The compound of claim 1, wherein any one of is phenyl that is unsubstituted or substituted with 1 to 5 deuteriums, and the remainder are deuteriums.

8. R １ is unsubstituted or substituted with 1 to 5 deuterium atoms; R ２ ~R ８ is deuterium; R ２ is unsubstituted or substituted with 1 to 5 deuterium atoms; R １ and R ３ ~R ８ is deuterium; R ３ is unsubstituted or substituted with 1 to 5 deuterium atoms; R １ , R ２ and R ４ ~R ８ is deuterium; or R ４ is unsubstituted or substituted with 1 to 5 deuterium atoms; R １ ~R ３ and R ５ ~R ８ The compound of claim 1 , wherein is deuterium.

9. The compound according to claim 1 , wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of: 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】

10. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10 , wherein the organic layer is a light-emitting layer.

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