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. The compound represented by Chemical Formula 1 can be used as a material for an organic material layer in an organic light-emitting device and can improve efficiency, low driving voltage, and lifespan characteristics in the organic light-emitting device.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2021-0020507 filed on February 16, 2021, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2022-0019692 filed on February 15, 2022, in the Korean Intellectual Property Office, the disclosures of which are incorporated herein by reference in their entirety.

[0003] The present disclosure relates to novel compounds and organic light-emitting devices comprising the same. Background Art

[0004] Generally speaking, organic light emitting diodes (OLEDs) are a phenomenon in which electrical energy is converted into light energy by utilizing organic materials. OLEDs utilizing organic light emitting diodes (OLEDs) have characteristics such as wide viewing angles, excellent contrast, fast response time, excellent brightness, driving voltage, and response speed, and therefore have been widely researched.

[0005] An organic light-emitting device typically has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer typically has a multilayer structure containing different materials to enhance the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0006] There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices as described above.

[0007] [Prior art literature]

[0008] [Patent Document]

[0009] (Patent Document 1) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] An object of the present disclosure is to provide a novel organic light-emitting material and an organic light-emitting device comprising the same.

[0012] Technical Solution

[0013] According to one aspect of the present disclosure, there is provided a compound represented by the following Chemical Formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In Chemical Formula 1,

[0017] R1 to R 12 Any one of them is a substituent represented by the following Chemical Formula 2, and the rest are hydrogen or deuterium.

[0018] [Chemical Formula 2]

[0019]

[0020] In Chemical Formula 2,

[0021] L1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthalenediyl group,

[0022] L2 and L3 are each independently a single bond; substituted or unsubstituted C 6-60 Arylene; or a substituted or unsubstituted C containing at least one selected from N, O and S 2-60 Heteroarylene, and

[0023] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl.

[0024] According to another aspect of the present disclosure, an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains a compound represented by Chemical Formula 1.

[0025] Beneficial effects

[0026] The compound represented by Chemical Formula 1 can be used as a material for an organic material layer of an organic light-emitting device, and can improve efficiency, achieve low driving voltage, and / or improve lifespan characteristics in 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

[0027] Figure 1 An example of an organic light-emitting device including a substrate 1 , an anode 2 , an electron blocking layer 3 , a light-emitting layer 4 , and a cathode 5 is shown.

[0028] Figure 2An example of an organic light emitting device including a substrate 1 , an anode 2 , a hole injection layer 6 , a hole transport layer 7 , an electron blocking layer 3 , a light emitting layer 4 , a hole blocking layer 8 , an electron transport and injection layer 9 , and a cathode 5 is shown. DETAILED DESCRIPTION

[0029] Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.

[0030] Provided herein are compounds represented by Chemical Formula 1.

[0031] As used herein, the notation or It refers to the bond to another substituent.

[0032] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heteroaryl group containing at least one of N, O, and S atoms, or unsubstituted or substituted with a substituent in which two or more substituents are linked together from among the substituents exemplified above. For example, a "substituent in which two or more substituents are linked together" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are linked together.

[0033] In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a substituent having the following structural formula, but is not limited thereto.

[0034]

[0035] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group may be substituted by 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 ester group may be a substituent having the following structural formula, but is not limited thereto.

[0036]

[0037] In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a substituent having the following structural formula, but is not limited thereto.

[0038]

[0039] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0040] In the present disclosure, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0041] In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0042] In the present disclosure, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include 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, but are not limited thereto.

[0043] In the present disclosure, the alkenyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof 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, stilbene, styryl, etc., but are not limited thereto.

[0044] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0045] In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but not limited thereto.

[0046] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0047] In the present disclosure, the heteroaryl group is a heteroaryl group containing at least one of O, N, Si and S as a heteroatom, and its carbon number is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment of the heteroaryl group, the heteroaryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but are not limited thereto.

[0048] In the present disclosure, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine groups is the same as the above-mentioned examples of aryl groups. In the present disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the above-mentioned examples of alkyl groups. In the present disclosure, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of heteroaryl groups. In the present disclosure, the alkenyl group in aralkenyl groups is the same as the above-mentioned examples of alkenyl groups. In the present disclosure, the above-mentioned description of aryl groups can be applied, except that the arylene group is a divalent group. In the present disclosure, the above-mentioned description of heteroaryl groups can be applied, except that the heteroarylene group is a divalent group. In the present disclosure, the above-mentioned description of aryl or cycloalkyl groups can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the above-mentioned description of heteroaryl groups can be applied, except that the heteroaryl group is not a monovalent group but is formed by combining two substituents.

[0049] Preferably, R1, R3 to R 10 and R 12 Any one of them is a substituent represented by Chemical Formula 2, and the others are each independently hydrogen or deuterium, and R2 and R 11 can be independently hydrogen or deuterium. Preferably, R1, R3 to R 10 and R 12 Any one of them is a substituent represented by Chemical Formula 2, the others are each independently hydrogen, and R2 and R 11 may each independently be hydrogen.

[0050] Preferably, L1 may be a phenylene group which is unsubstituted or substituted with one phenyl group, a biphenyldiyl group which is unsubstituted or substituted with one phenyl group, or a naphthalenediyl group.

[0051] More preferably, L1 can be any one selected from the following:

[0052]

[0053] More preferably, L1 can be any one selected from the following:

[0054]

[0055] Preferably, L2 and L3 can each independently be a single bond; substituted or unsubstituted C 6-20 Arylene; or a substituted or unsubstituted C containing at least one selected from N, O and S 2-20 Heteroarylene.

[0056] More preferably, L2 and L3 may each independently be a single bond, a phenylene group, a biphenyldiyl group, or a naphthalene diyl group, and still more preferably, L2 and L3 are each independently a single bond, a phenylene group, a phenylene group substituted with one phenyl group, a biphenyldiyl group, or a naphthalene diyl group.

[0057] Most preferably, L2 and L3 may each independently be a single bond or any one selected from the following:

[0058]

[0059] Preferably, Ar1 and Ar2 can each independently be a substituted or unsubstituted C 6-20 aryl, or a substituted or unsubstituted C 2-20 Heteroaryl.

[0060] More preferably, Ar1 and Ar2 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a phenylnaphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phenylcarbazolyl group, a dimethylfluorenyl group, a benzonaphthofuranyl group, or a benzonaphthothiophenyl group.

[0061] More preferably, Ar1 and Ar2 may each independently be any one selected from the following:

[0062]

[0063] Most preferably, Ar1 and Ar2 can each independently be any one selected from the following:

[0064]

[0065] Preferably, any one of Ar1 and Ar2 may be a substituted or unsubstituted C 6-60 More preferably, any one of Ar1 and Ar2 may be a substituted or unsubstituted C 6-20 Still more preferably, any one of Ar1 and Ar2 may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group or a dimethylfluorenyl group.

[0066] Most preferably, any one of Ar1 and Ar2 may be any one selected from the following:

[0067]

[0068] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0069]

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[0190] As an example, the compound represented by Chemical Formula 1 (wherein R1 to R 12 Any one of them is a substituent represented by the following Chemical Formula 2, and the rest are hydrogen) can be prepared by the preparation method shown in the following Reaction Scheme 1, and the remaining compounds can be prepared in a similar manner.

[0191] [Reaction Scheme 1]

[0192]

[0193] In Reaction Scheme 1, L1 to L3, Ar1 and Ar2 are as defined in Chemical Formula 1, X is a halogen, and preferably, X is chlorine or bromine.

[0194] Reaction Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used in the Suzuki coupling reaction can be modified as known in the art. The above preparation method can be further embodied in the preparation examples described below.

[0195] In another embodiment of the present disclosure, an organic light-emitting device is provided that includes a compound represented by Chemical Formula 1. In one example, the present disclosure provides an organic light-emitting device that includes: a first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers includes the compound represented by Chemical Formula 1.

[0196] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers.

[0197] In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer may include the compound represented by Chemical Formula 1.

[0198] In addition, the organic material layer may include a hole transport layer, a hole injection layer, or a layer for simultaneous hole transport and injection, wherein the hole transport layer, the hole injection layer, or the layer for simultaneous hole transport and injection may contain the compound represented by Chemical Formula 1.

[0199] In addition, the organic material layer may include an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.

[0200] In addition, the organic light emitting device according to the present disclosure may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present disclosure may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to one embodiment of the present disclosure is shown in FIG. Figure 1 and Figure 2 middle.

[0201] Figure 1 An example of an organic light-emitting device including a substrate 1 , an anode 2 , an electron blocking layer 3 , a light-emitting layer 4 , and a cathode 5 is shown. Figure 2 An example of an organic light-emitting device is shown, including a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, an electron blocking layer 3, a light-emitting layer 4, a hole blocking layer 8, an electron transport and injection layer 9, and a cathode 5. In such a structure, the compound represented by Chemical Formula 1 may be contained in the hole transport layer, the electron blocking layer, or the light-emitting layer.

[0202] The organic light-emitting device according to the present disclosure can be manufactured using materials and methods known in the art, except that at least one of the organic material layers contains the compound represented by Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0203] For example, the organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0204] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer by a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0205] In addition to such a method, an organic light emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0206] As an example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.

[0207] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include: 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; conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0208] As the cathode material, a material with a small work function is generally preferred, so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials 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; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like.

[0209] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, so it has the effect of injecting holes in the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and is also excellent in the ability to form a thin film. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, but are not limited thereto.

[0210] The 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 layer is suitably a material with a large hole mobility, which can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers in which conjugated and non-conjugated parts are present simultaneously, etc., but are not limited thereto. Preferably, the compound represented by Chemical Formula 1 can be used as a material for the hole transport layer.

[0211] The electron blocking layer is a layer disposed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from transferring to the hole transport layer and not recombining in the light-emitting layer. It can also be called an electron suppression layer. The electron blocking layer is preferably made of a material with a lower electron affinity than the electron transport layer. Preferably, the compound represented by Chemical Formula 1 can be used as the material for the electron blocking layer.

[0212] The light-emitting material is preferably a material that can receive holes and electrons transferred from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light-emitting material include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based compounds; azole-, benzothiazole-, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0213] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic compound, or the like. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocyclic compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Preferably, the compound represented by Chemical Formula 1 may be included as the host material.

[0214] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, , diindenopyrene, etc. Styrylamine compounds are compounds in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0215] The hole blocking layer is provided between the electron transport layer and the light emitting layer to prevent holes injected from the anode from transferring to the electron transport layer and not being recombined in the light emitting layer.

[0216] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material is suitably a material that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer, and has a large electron mobility. Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline, complexes including Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the relevant technology. In particular, suitable examples of cathode materials are typical materials with a small work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0217] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an excellent effect of injecting electrons from the cathode and injecting electrons into the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, The examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives and the like.

[0218] Examples of metal complex compounds include 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-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, bis(2-methyl-8-quinolinato)(2-naphthol)gallium, and the like, but are not limited thereto.

[0219] On the other hand, in the present disclosure, an “electron injection and transport layer” or an “electron transport and injection layer” is a layer that functions as both an electron injection layer and an electron transport layer, and the materials that function as each layer can be used alone or in combination without limitation.

[0220] The organic light emitting device according to the present disclosure may be a front-side emission type, a rear-side emission type, or a dual-side emission type based on the materials used.

[0221] Meanwhile, the organic light emitting device according to the present disclosure may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.

[0222] Hereinafter, preferred embodiments are presented to help understand the present disclosure. However, the following embodiments are provided only for a better understanding of the present disclosure and are not intended to limit the present disclosure.

[0223] [Preparation Example]

[0224] Preparation Example 1

[0225]

[0226] Under a nitrogen atmosphere, compound A (15g, 57.1mmol) and compound amine 1 (29.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water, and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 11.9g compound 1. (yield: 31%, MS:[M+H] + =674)

[0227] Preparation Example 2

[0228]

[0229] Under a nitrogen atmosphere, compound A (15g, 57.1mmol) and compound amine 2 (31.3g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 15.3g compound 2. (yield: 38%, MS:[M+H]+ =704)

[0230] Preparation Example 3

[0231]

[0232] Under a nitrogen atmosphere, compound A (15g, 57.1mmol) and compound amine 3 (26.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 9 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 11.4g compound 3. (yield: 32%, MS:[M+H] + =624)

[0233] Preparation Example 4

[0234]

[0235] Under a nitrogen atmosphere, compound A (15g, 57.1mmol) and compound amine 4 (35.6g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 14.6g compound 4. (yield: 33%, MS:[M+H] + =776)

[0236] Preparation Example 5

[0237]

[0238] Under a nitrogen atmosphere, compound A (15g, 57.1mmol) and compound amine 5 (35.6g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 15g of compound 5. (yield: 34%, MS:[M+H] + =776)

[0239] Preparation Example 6

[0240]

[0241] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 6 (24.9g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 24.6g compound 6. (yield: 72%, MS:[M+H] + =598)

[0242] Preparation Example 7

[0243]

[0244] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 7 (26.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 26.7g compound 7. (yield: 75%, MS:[M+H] + =624)

[0245] Preparation Example 8

[0246]

[0247] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 8 (27.3g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 23.6g compound 8. (yield: 65%, MS:[M+H] + =638)

[0248] Preparation Example 9

[0249]

[0250] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 9 (22.7g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 21.8g compound 9. (yield: 68%, MS:[M+H] + =562)

[0251] Preparation Example 10

[0252]

[0253] Under nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 10 (29.1g, 59.9mmol) are added in 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 27g compound 10. (yield: 71%, MS:[M+H] + =668)

[0254] Preparation Example 11

[0255]

[0256] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 11 (32.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 33g compound 11. (yield: 80%, MS:[M+H] + =724)

[0257] Preparation Example 12

[0258]

[0259] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 12 (38.6g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 33.5g compound 12. (yield: 71%, MS:[M+H] + =826)

[0260] Preparation Example 13

[0261]

[0262] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 13 (32.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 9 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 27.3g compound 13. (yield: 66%, MS:[M+H] + =724)

[0263] Preparation Example 14

[0264]

[0265] Under a nitrogen atmosphere, compound B (15g, 57.1mmol) and compound amine 14 (34g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 30.8g compound 14. (yield: 72%, MS:[M+H] + =750)

[0266] Preparation Example 15

[0267]

[0268] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 15 (26.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 28.5g of compound 15. (yield: 80%, MS:[M+H] + =624)

[0269] Preparation Example 16

[0270]

[0271] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 16 (29.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 23.8g compound 16. (yield: 62%, MS:[M+H] + =674)

[0272] Preparation Example 17

[0273]

[0274] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 17 (27.2g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 9 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 24.7g compound 17. (yield: 68%, MS:[M+H] + =637)

[0275] Preparation Example 18

[0276]

[0277] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 18 (28.1g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 28.3g of compound 18. (yield: 76%, MS:[M+H] + =652)

[0278] Preparation Example 19

[0279]

[0280] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 19 (30.7g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 30.5g of compound 19. (yield: 77%, MS:[M+H] + =694)

[0281] Preparation Example 20

[0282]

[0283] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 20 (25.7g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 24.4g compound 20. (yield: 70%, MS:[M+H] + =612)

[0284] Preparation Example 21

[0285]

[0286] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 21 (29.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 25.4g compound 21. (yield: 66%, MS:[M+H] + =674)

[0287] Preparation Example 22

[0288]

[0289] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 22 (38.6g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 9 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 30.2g compound 22. (yield: 64%, MS:[M+H] + =826)

[0290] Preparation Example 23

[0291]

[0292] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 23 (38.6g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 33.9g compound 23. (yield: 72%, MS:[M+H] + =826)

[0293] Preparation Example 24

[0294]

[0295] Under a nitrogen atmosphere, compound C (15g, 57.1mmol) and compound amine 24 (29.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 23.8g compound 24. (yield: 62%, MS:[M+H] + =674)

[0296] Preparation Example 25

[0297]

[0298] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 25 (31g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 29.5g compound 25. (yield: 74%, MS:[M+H] + =700)

[0299] Preparation Example 26

[0300]

[0301] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 26 (30.1g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 9 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 25.4g compound 26. (yield: 65%, MS:[M+H] + =684)

[0302] Preparation Example 27

[0303]

[0304] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 27 (28.9g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 29.2g compound 27. (yield: 77%, MS:[M+H] + =664)

[0305] Preparation Example 28

[0306]

[0307] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 28 (26.7g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 21.8g compound 28. (yield: 61%, MS:[M+H] + =628)

[0308] Preparation Example 29

[0309]

[0310] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 29 (31g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 31.9g compound 29. (yield: 80%, MS:[M+H] + =700)

[0311] Preparation Example 30

[0312]

[0313] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 30 (37g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 32.4g compound 30. (yield: 71%, MS:[M+H] + =800)

[0314] Preparation Example 31

[0315]

[0316] Under a nitrogen atmosphere, compound D (15g, 57.1mmol) and compound amine 31 (32.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 29.3g compound 31. (yield: 71%, MS:[M+H] + =724)

[0317] Preparation Example 32

[0318]

[0319] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 32 (21.9g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 19.1g compound 32. (yield: 61%, MS:[M+H] + =548)

[0320] Preparation Example 33

[0321]

[0322] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 33 (35.6g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 31.9g compound 33. (yield: 72%, MS:[M+H] + =776)

[0323] Preparation Example 34

[0324]

[0325] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 34 (28.3g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 25g of compound 34. (yield: 67%, MS:[M+H] + =654)

[0326] Preparation Example 35

[0327]

[0328] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 35 (31.8g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 26.4g compound 35. (yield: 65%, MS:[M+H] + =713)

[0329] Preparation Example 36

[0330]

[0331] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 36 (24.3g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 21.1g compound 36. (yield: 63%, MS:[M+H] + =588)

[0332] Preparation Example 37

[0333]

[0334] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 37 (25.7g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 25.5g of compound 37. (yield: 73%, MS:[M+H] + =612)

[0335] Preparation Example 38

[0336]

[0337] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 38 (26.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 23.1g compound 38. (yield: 65%, MS:[M+H] + =624)

[0338] Preparation Example 39

[0339]

[0340] Under a nitrogen atmosphere, compound E (15g, 57.1mmol) and compound amine 39 (32.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 25.2g of compound 39. (yield: 61%, MS:[M+H] + =724)

[0341] Preparation Example 40

[0342]

[0343] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 40 (32.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is again dissolved in chloroform, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 26g compound 40. (yield: 63%, MS:[M+H] + =724)

[0344] Preparation Example 41

[0345]

[0346] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 41 (27.9g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 11 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 26.6g compound 41. (yield: 72%, MS:[M+H] + =648)

[0347] Preparation Example 42

[0348]

[0349] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 42 (27.3g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 29.1g compound 42. (yield: 80%, MS:[M+H] + =638)

[0350] Preparation Example 43

[0351]

[0352] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 43 (26.7g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 23.3g compound 43. (yield: 65%, MS:[M+H] + =628)

[0353] Preparation Example 44

[0354]

[0355] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 44 (26.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine) palladium (0) (0.3g, 0.6mmol) is added. After reacting for 10 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 26g compound 44. (yield: 73%, MS:[M+H] + =624)

[0356] Preparation Example 45

[0357]

[0358] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 45 (32.5g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 12 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 30.6g compound 45. (yield: 74%, MS:[M+H] + =724)

[0359] Preparation Example 46

[0360]

[0361] Under a nitrogen atmosphere, compound F (15g, 57.1mmol) and compound amine 46 (31g, 59.9mmol) are added to 300ml THF, and the mixture is stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) is dissolved in 71ml water and added to the mixture, and the mixture is fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3g, 0.6mmol) is added. After reacting for 8 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is then distilled. It is dissolved in chloroform again, washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 25.6g of compound 46. (yield: 64%, MS:[M+H] + =700)

[0362] [Example]

[0363] Example 1-1

[0364] It is coated with a thickness of The glass substrate of the film of ITO (indium tin oxide) of 1000nm is put into the distilled water that comprises the detergent that is dissolved therein, and washes by ultrasonic wave.In this case, the detergent used is the product that can be commercially available from Fischer Co., and distilled water is the distilled water that is filtered twice by using the filter that can be commercially available from Millipore Co..ITO was cleaned 30 minutes, then repeated twice ultrasonic cleaning 10 minutes by using distilled water.After completing with distilled water washing, by substrate isopropyl alcohol, acetone and methanol solvent ultrasonic washing and drying, be transferred to plasma cleaning machine afterwards.Then, substrate was cleaned 5 minutes with oxygen plasma, then transferred to vacuum evaporator.

[0365] On the ITO transparent electrode prepared in this way, the following compound HI-1 was applied as The hole injection layer was formed with a thickness of 1.5 wt % by weight, and the following compound A-1 was p-doped. The following compound HT-1 was vacuum deposited on the hole injection layer to form a film with a thickness of Then, the compound 1 prepared in Preparation Example 1 was thermally vacuum deposited onto The thickness of the electron blocking layer is then vacuum deposited onto the following compound BH and the following compound BD at a weight ratio of 25:1. Then, the following compound HB-1 was vacuum deposited onto Then, the following compound ET-1 and the following compound LiQ were thermally vacuum deposited onto the substrate at a weight ratio of 1:1. The thickness of the layer is used as a layer for both electron transport and electron injection. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron injection and transport layer to a thickness of and To form a cathode, thereby manufacturing an organic light-emitting device.

[0366]

[0367] During the above process, the deposition rate of the organic material is kept at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 support, thereby manufacturing an organic light-emitting device.

[0368] Example 1-2 to Example 1-46

[0369] Organic light-emitting devices of Examples 1-2 to 1-46 were manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 below were used instead of Compound 1.

[0370] Comparative Examples 1-1 to 1-9

[0371] Organic light-emitting devices of Comparative Examples 1-1 to 1-9 were manufactured in the same manner as in Example 1-1, except that the following compounds EB1 to EB9 were used instead of Compound 1.

[0372]

[0373] [Experimental example]

[0374] By applying a current (10 mA / cm 2 ) were used to measure the driving voltage and efficiency, and the results are shown in the following Table 1. The lifespan T95 means the time required for the luminance to decrease to 95% of the initial luminance (1000 nits).

[0375] [Table 1]

[0376]

[0377]

[0378]

[0379] As shown in Table 1, it was confirmed that the compound of the present disclosure has excellent electron blocking ability, and thus, the organic light emitting device including it as an electron blocking layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

[0380] <Reference Signs>

[0381] 1: substrate 2: anode

[0382] 3: Electron blocking layer 4: Light-emitting layer

[0383] 5: cathode 6: hole injection layer

[0384] 7: Hole transport layer 8: Hole blocking layer

[0385] 9: Electron transport and injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In Chemical Formula 1, R1 to R 12 Any one of them is a substituent represented by the following Chemical Formula 2, and the rest are hydrogen or deuterium, [Chemical Formula 2] In Chemical Formula 2, L1 is unsubstituted or substituted phenylene, unsubstituted or substituted biphenyldiyl, or naphthalene diyl, L2 and L3 are each independently a single bond, a phenylene group, a phenylene group substituted with one phenyl group, a biphenyldiyl group, or a naphthalenediyl group, and Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a phenylnaphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phenylcarbazolyl group, a dimethylfluorenyl group, a benzonaphthofuranyl group, or a benzonaphthothiophenyl group.

2. The compound according to claim 1, wherein L1 is any one selected from the following:

3. The compound according to claim 1, wherein L2 and L3 are each independently a single bond or any one selected from the following:

4. The compound according to claim 1, wherein: Ar1 and Ar2 are each independently any one selected from the following:

5. The compound according to claim 1, wherein Any one of Ar1 and Ar2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, or a phenylnaphthyl group.

6. The compound according to claim 1, wherein The compound represented by Chemical Formula 1 is any one selected from the following:

7. An organic light-emitting device, comprising: a first electrode; a second electrode disposed 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 6. The organic light emitting device according to claim 7 , wherein The organic material layer is an electron blocking layer.

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