Novel compound and organic light-emitting device comprising same

Abstract

The present disclosure relates to a novel compound and an organic light emitting device comprising the same. The present invention provides a compound represented by Chemical Formula 1, which can be used as a material of an organic material layer of an organic light-emitting device, and in which efficiency can be improved, a low driving voltage can be achieved, and / or lifespan characteristics can be improved.

Description

[0001] This application is a divisional application of a Chinese patent application with an application date of December 14, 2021, an application number of "202180065246.5", and an invention title of "New Compounds and Organic Light-Emitting Devices Containing the Same". Technical Field

[0002] The present disclosure relates to new compounds and organic light-emitting devices containing the same. Background Art

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic light-emitting devices utilizing the organic light-emitting phenomenon have characteristics such as wide viewing angles, excellent contrast ratios, fast response times, and excellent brightness, driving voltage, and response speed, and thus many studies have been conducted.

[0004] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer often has a multilayer structure containing different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer can be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of an organic light-emitting device, when 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 each other, excitons are formed, and light is emitted when the excitons fall back to the ground state again.

[0005] There is a continuous need to develop new materials for organic materials used in the above-described organic light-emitting devices.

[0006] Prior Art Documents

[0007] Patent Documents

[0008] (Patent Document 1) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention

[0009] Technical Problem

[0010] The present disclosure relates to new organic light-emitting materials and organic light-emitting devices containing the same.

[0011] Technical Solution

[0012] In the present disclosure, a compound represented by the following Chemical Formula 1 is provided:

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] A is a thiazole ring fused to an adjacent ring or an oxazole ring,

[0017] L1 is a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C 2-60 heteroarylene containing at least one selected from N, O, and S,

[0018] R1 is

[0019] Ar1 to Ar4 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from N, O, and S,

[0020] L2 to L5 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C 2-60 heteroarylene containing at least one selected from N, O, and S,

[0021] R2 is a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl,

[0022] D is deuterium, and

[0023] n is an integer of 0 or greater and 5 or less.

[0024] In addition, an organic light-emitting device is provided, which includes: 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 at least one of the organic material layers contains at least one compound represented by Chemical Formula 1.

[0025] Advantageous Effects

[0026] The compound represented by Chemical Formula 1 can be used as a material for the organic material layer of an organic light-emitting device, and can improve the efficiency, achieve a low driving voltage and / or improve the lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a material for hole injection, hole transport, light emission, electron transport, and / or electron injection. Description of the Drawings

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

[0028] Figure 2 An example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 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] In the present disclosure, a compound represented by Chemical Formula 1 is provided.

[0031] As used herein, the symbol or means a bond connected to another substituent.

[0032] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: 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 arylphosphine group; and a heteroaryl containing at least one of N, O, and S atoms, or unsubstituted or substituted with a substituent in which two or more of the above-exemplified substituents are connected. For example, the "substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may also be interpreted as a substituent in which two phenyl groups are connected.

[0033] In the present disclosure, the number of carbon atoms 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 is 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 ester group may be a substituent having the following structural formula, but is not limited thereto.

[0036]

[0037] In the present disclosure, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25.

[0038] Specifically, the imide group may be a substituent having the following structural formula, but is not limited thereto.

[0039]

[0040] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0041] In the present disclosure, the boron group specifically includes trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, and phenylboron, but is not limited thereto.

[0042] In the present disclosure, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0043] In the present disclosure, the alkyl group may be straight-chain or branched-chain, and there is no particular limitation on the number of carbon atoms thereof, but it is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms 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, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

[0044] In the present disclosure, the alkenyl group may be linear or branched, and there is no particular limitation on the number of carbon atoms thereof, but it is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to still another embodiment, the alkenyl group has 2 to 6 carbon atoms. 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-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl)ethenyl-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0045] In the present disclosure, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. 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 still another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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, etc., but are not limited thereto.

[0046] In the present disclosure, the aryl group is not particularly limited, but the number of carbon atoms thereof is preferably 6 to 60, and it 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. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but are not limited thereto. The polycyclic aryl group includes naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited thereto.

[0047] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro ring structure. When the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0048] In the present disclosure, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroatoms, and there is no particular limitation on the number of carbon atoms thereof, but it is preferably 2 to 60. According to an exemplary embodiment, 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, oxazolyl, Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, iso azolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but not limited thereto.

[0049] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl, and arylamino is the same as the aforementioned examples of aryl. In the present disclosure, the alkyl in aralkyl, alkylaryl, and alkylamino is the same as the aforementioned examples of alkyl. In the present disclosure, the heteroaryl in heteroarylamine can apply the aforementioned description of heteroaryl. In the present disclosure, the alkenyl in aralkenyl is the same as the aforementioned examples of alkenyl. In the present disclosure, the aforementioned description of aryl can be applied, with the difference that the arylene is a divalent group. In the present disclosure, the aforementioned description of heteroaryl can be applied, with the difference that the heteroarylene is a divalent group. In the present disclosure, the aforementioned description of aryl or cycloalkyl can be applied, with the difference that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the aforementioned description of heteroaryl can be applied, with the difference that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0050] Preferably, Formula 1 can be represented by any one of the following Formulas 1-1 to 1-4:

[0051] [Formula 1-1]

[0052]

[0053] [Formula 1-2]

[0054]

[0055] [Formula 1-3]

[0056]

[0057] [[ID=?]]

[0058]

[0059] [Formula 1-4]In Formulas 1-1 to 1-4,

[0060] R1, R2, L1, D, and n are defined as in Formula 1.

[0061] Preferably, L1 can be a single bond; a substituted or unsubstituted C 6-20 arylene; or a substituted or unsubstituted C 2-20 heteroarylene containing at least one selected from N, O, and S.

[0062] More preferably, L1 can be a single bond, phenylene, biphenyldiyl, or naphthalenediyl.

[0063] Most preferably, L1 can be a single bond or any one selected from the following:

[0064]

[0065] 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 containing at least one selected from N, O, and S.

[0066] More preferably, Ar1 and Ar2 can each independently be phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl.

[0067] Most preferably, Ar1 and Ar2 can each independently be any one selected from the following:

[0068]

[0069] Preferably, Ar3 and Ar4 can each independently be a substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing at least one selected from N, O, and S.

[0070] More preferably, Ar3 and Ar4 can each independently be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, or phenylnaphthyl.

[0071] Most preferably, Ar3 and Ar4 can each independently be any one selected from the following:

[0072]

[0073] Preferably, L2 and L3 can each independently be a single bond; or a substituted or unsubstituted C 6-20 arylene.

[0074] More preferably, L2 and L3 can each independently be a single bond, phenylene, or naphthalenediyl.

[0075] Most preferably, L2 and L3 can each independently be a single bond or any one selected from the following:

[0076]

[0077] Preferably, L4 and L5 can each independently be a single bond; a substituted or unsubstituted C 6-20 arylene; or a substituted or unsubstituted C 2-20 heteroarylene containing at least one selected from N, O, and S.

[0078] More preferably, L4 and L5 can each independently be a single bond, phenylene, biphenyldiyl, naphthalenediyl, or carbazolediyl.

[0079] Most preferably, L4 and L5 can each independently be a single bond or any one selected from the following:

[0080]

[0081] Preferably, at least one of Ar1 and Ar2 can be a substituted or unsubstituted C 6-60 aryl, more preferably, at least one of Ar1 and Ar2 can be a substituted or unsubstituted C 6-20 aryl, more preferably, at least one of Ar1 and Ar2 can be an unsubstituted C 6-20 aryl, and most preferably, at least one of Ar1 and Ar2 can be phenyl or naphthyl.

[0082] Preferably, at least one of Ar3 and Ar4 can be a substituted or unsubstituted C 6-60 aryl, more preferably, at least one of Ar3 and Ar4 can be a substituted or unsubstituted C 6-20 aryl, more preferably, at least one of Ar3 and Ar4 can be an unsubstituted C 6-20 aryl, and most preferably, at least one of Ar3 and Ar4 can be phenyl, biphenyl, or naphthyl.

[0083] Meanwhile, R2 is a substituent of ring A.

[0084] Preferably, R2 can be a substituted or unsubstituted C 6-20 aryl; or a substituted or unsubstituted C 2-20 heteroaryl containing at least one selected from N, O, and S.

[0085] More preferably, R2 can be phenyl, biphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.

[0086] Most preferably, R2 can be any one selected from the following:

[0087]

[0088] Preferably, n can be 0.

[0089] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

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[0305]

[0306] In Chemical Formula 1, when L1 is a single bond and R1 is the compound can be prepared by the preparation method shown in Reaction Scheme 1 below. Some compounds can be prepared by the preparation method shown in Reaction Scheme 2 below, and other compounds can be prepared similarly.

[0307] [Reaction Scheme 1]

[0308]

[0309] [Reaction Scheme 2]

[0310]

[0311] In Reaction Schemes 1 and 2, R1, R2, L1, L4, L5, Ar3 and Ar4, A, D and n are as defined in Chemical Formula 1 above, and X1 and X2 are each independently a halogen, and preferably chlorine or bromine.

[0312] Reaction Scheme 1 is an amine substitution reaction and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be varied as known in the art. In addition, Reaction Scheme 2 is a Suzuki coupling reaction and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be varied as known in the art. The preparation method can be described more specifically in the Preparation Examples described below.

[0313] In addition, an organic light-emitting device including the compound represented by Chemical Formula 1 described above is provided. As an example, an organic light-emitting device is provided, which includes: 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 at least one layer of the organic material layers contains at least one compound represented by Chemical Formula 1.

[0314] 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 multi-layer 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.

[0315] In addition, the organic material layer may include an electron blocking layer or a light-emitting layer, and the electron blocking layer or the light-emitting layer may contain a compound represented by Chemical Formula 1.

[0316] 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, Figure 1 and Figure 2 illustrate the structure of an organic light-emitting device according to an embodiment of the present disclosure.

[0317] Figure 1 An example of an organic light-emitting device including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 is shown. Figure 2 An example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer or the electron blocking layer.

[0318] The organic light emitting device according to the present disclosure can be manufactured by materials and methods known in the art, except that one or more layers in the organic material layer contain a 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.

[0319] 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 the substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method 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.

[0320] In addition, when manufacturing the organic light emitting device, the compound represented by Chemical Formula 1 can be formed into an organic layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0321] 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 (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0322] 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.

[0323] As an anode material, generally, a material having a large work function is preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material 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 polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0324] As a cathode material, generally, a material having a small work function is preferably used so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include: 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, but are not limited thereto.

[0325] 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, and thus has the effect of injecting holes into the anode, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and is excellent in the ability to form a thin film. The HOMO (highest occupied molecular orbital) of the preferred hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.

[0326] 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 material is suitably a material having 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 arylamine-based organic materials, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, and the like, but are not limited thereto.

[0327] The electron blocking layer is a layer placed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from transferring to the hole transport layer without recombination in the light-emitting layer, and is also referred to as an electron suppression layer. For the electron blocking layer, a material having an electron affinity lower than that of the electron transport layer is preferred. Preferably, the material represented by Chemical Formula 1 in the present disclosure can be used as the electron blocking material.

[0328] The light-emitting material is suitably a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining them, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; distyrylbenzene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benz oxazole, based on benzothiazole and based on benzimidazole compounds; polymers based on poly(p-phenylene vinylene) (PPV); spiro compounds; polyfluorene; rubrene; and the like, but are not limited thereto.

[0329] Specifically, 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, etc. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. Preferably, the material represented by Chemical Formula 1 of the present disclosure may be used as the host material, and one or more materials represented by Chemical Formula 1 may be included as the host material. Preferably, when two types of compounds represented by Chemical Formula 1 are used in the light-emitting layer, the weight ratio thereof is from 10:90 to 90:10, and more preferably from 20:80 to 80:20, from 30:70 to 70:30, or from 40:60 to 60:40.

[0330] The dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having an arylamino group which is substituted or unsubstituted, and examples thereof include pyrene, anthracene, diindenoanthracene, etc. having an arylamino group. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one or two or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, etc., but is not limited thereto.

[0331] For example, at least one selected from the following may be used as the dopant material, but the present disclosure is not limited thereto:

[0332]

[0333]

[0334]

[0335] The hole blocking layer is a layer placed between the electron transport layer and the light-emitting layer to prevent holes injected from the anode from transferring to the electron transport layer without recombining in the light-emitting layer, and is also referred to as a hole suppression layer. For the hole blocking layer, a material having a high ionization energy is preferred.

[0336] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. As the electron transport material, 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 is suitable. Examples thereof include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the related art. In particular, suitable examples of the cathode material are typical materials having a low work function and followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer in each case.

[0337] 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 the effect of injecting electrons from the cathode, and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents excitons generated by 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 thereof include fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, and the like, and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and the like, but are not limited thereto.

[0338] Examples of the metal complex compounds include lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), chloro gallium bis(2-methyl-8-quinolate), (o-cresol) gallium bis(2-methyl-8-quinolate), (1-naphthol) aluminum bis(2-methyl-8-quinolate), (2-naphthol) gallium bis(2-methyl-8-quinolate), and the like, but are not limited thereto.

[0339] Meanwhile, the "electron injection and transport layer" used herein is a layer that performs the functions of both the electron injection layer and the electron transport layer, and the materials for each layer can be used alone or in combination, but the present disclosure is not limited thereto.

[0340] The organic light-emitting device according to the present disclosure can be a bottom-emission device, a top-emission device, or a double-sided emission device, and in particular, can be a bottom-emission device that requires a relatively high luminous efficiency.

[0341] In addition, in addition to the organic light-emitting device, the compound represented by Chemical Formula 1 can also be included in an organic solar cell or an organic transistor.

[0342] The preparation of the compound represented by Chemical Formula 1 and the organic light-emitting device containing the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of the present disclosure.

[0343] [Preparation Example]

[0344] Preparation Example 1-1

[0345]

[0346] Under a nitrogen atmosphere, Compound AA (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.7 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well, and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of Compound subAA-1 (yield 63%, MS: [M+H]+ = 396).

[0347]

[0348] Under a nitrogen atmosphere, Compound subAA-1 (15 g, 37.9 mmol) and bis(pinacolato)diboron (10.6 g, 41.7 mmol) were added to 300 ml of 1,4-di ane, and the mixture was stirred and refluxed. Then, potassium acetate (5.6 g, 56.8 mmol) was added and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.3 mmol) were added. After reacting for 8 hours, it was cooled to room temperature. Then, the organic layer was separated using chloroform and water and distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g of Compound subAA-2 (yield 67%, MS: [M+H]+ = 488).

[0349]

[0350] Under a nitrogen atmosphere, compound subAA-2 (15 g, 30.8 mmol) and Trz1 (9.8 g, 30.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (12.8 g, 92.3 mmol) was dissolved in 38 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9 g of compound 1-1 (yield 60%, MS: [M+H]+ = 643).

[0351] Preparation Example 1-2

[0352]

[0353] Under a nitrogen atmosphere, compound AB (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of compound subAB-1 (yield 78%, MS: [M+H]+ = 320).

[0354]

[0355] Under a nitrogen atmosphere, to 300 ml of 1,4-di Compound subAB-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to an alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol) were added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated using chloroform and water and distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.3 g of compound subAB-2 (yield 74%, MS: [M+H]+ = 412).

[0356]

[0357] Compound subAB-2 (15 g, 36.5 mmol) and Trz2 (9.8 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.1 g, 109.4 mmol) was dissolved in 45 ml of water and then added thereto. Thereafter, it was stirred well, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g of compound 1-2 (yield 66%, MS: [M+H]+ = 517).

[0358] Preparation Example 1-3

[0359]

[0360] Under a nitrogen atmosphere, compound AE (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.7 g of compound subAE-1 (yield 62%, MS: [M+H]+ = 320).

[0361]

[0362] Under a nitrogen atmosphere, compound subAE-1 (15 g, 46.9 mmol) and Trz3 (22.5 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After a 9-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.3 g of compound 1-3 (yield 75%, MS: [M+H]+ = 719).

[0363] Preparation Example 1-4

[0364]

[0365] Under a nitrogen atmosphere, compound subAE-1 (15 g, 46.9 mmol) and Trz4 (20.8 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.1 g of compound 1-4 (yield 69%, MS: [M+H]+ = 683).

[0366] Preparation Example 1-5

[0367]

[0368] Under a nitrogen atmosphere, compound AF (15 g, 53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After the reaction for 8 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1 g of compound subAF-1 (yield 66%, MS: [M+H]+ = 370).

[0369]

[0370] Under a nitrogen atmosphere, compound subAF-1 (15 g, 40.6 mmol) and Trz5 (16.4 g, 40.6 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and then added thereto. Thereafter, it was stirred well, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.4 g of compound 1-5 (yield 62%, MS: [M+H]+ = 693).

[0371] Preparation Example 1-6

[0372]

[0373] Under a nitrogen atmosphere, compound BA (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well, and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.6 g of compound subBA-1 (yield 79%, MS: [M+H]+ = 320).

[0374]

[0375] Under a nitrogen atmosphere, to 300 ml of 1,4-di Compound subBA-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to an alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol) were added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated using chloroform and water and distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1 g of compound subBA-2 (yield 68%, MS: [M+H]+ = 412).

[0376]

[0377] Compound subBA-2 (15 g, 36.5 mmol) and Trz7 (14.4 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.1 g, 109.4 mmol) was dissolved in 45 ml of water and then added thereto. Thereafter, it was stirred well, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.5 g of compound 1-6 (yield 66%, MS: [M+H]+ = 643).

[0378] Preparation Example 1-7

[0379]

[0380] Under a nitrogen atmosphere, compound BB (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well, and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.2 g of compound subBB-1 (yield 65%, MS: [M+H]+ = 320).

[0381]

[0382] Under a nitrogen atmosphere, compound subBB-1 (15 g, 46.9 mmol) and Trz8 (18.9 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.1 g of compound 1-7 (yield 60%, MS: [M+H]+ = 643).

[0383] Preparation Example 1-8

[0384]

[0385] Under a nitrogen atmosphere, compound BE (15 g, 53.9 mmol) and dibenzo[b,d]thiophen-1-ylboronic acid (12.3 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reaction for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.7 g of compound subBE-1 (yield 73%, MS: [M+H]+ = 426).

[0386]

[0387] Under a nitrogen atmosphere, compound subBE-1 (15 g, 35.2 mmol) and Trz9 (14.2 g, 35.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g, 105.7 mmol) was dissolved in 44 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of compound 1-8 (yield 69%, MS: [M+H]+ = 749).

[0388] Preparation Example 1-9

[0389]

[0390] Under a nitrogen atmosphere, compound BF (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.5 g of compound subBF-1 (yield 61%, MS: [M+H]+ = 320).

[0391]

[0392] Under a nitrogen atmosphere, compound subBF-1 (15 g, 46.9 mmol) and Trz10 (22.5 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After a reaction for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.2 g of compound 1-9 (yield 60%, MS: [M+H]+ = 719).

[0393] Preparation Example 1-10

[0394]

[0395] Under a nitrogen atmosphere, compound CA (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.4 g of compound subCA-1 (yield 61%, MS: [M+H]+ = 336).

[0396]

[0397] Under a nitrogen atmosphere, compound subCA-1 (15 g, 44.7 mmol) and Trz12 (19.2 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 8 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.5 g of compound 1-10 (yield 67%, MS: [M+H]+ = 685).

[0398] Preparation Example 1-11

[0399]

[0400] Under a nitrogen atmosphere, compound CB (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound subCB-1 (yield 77%, MS: [M+H]+ = 336).

[0401]

[0402] Under a nitrogen atmosphere, to 300 ml of 1,4-di ane was added compound subCB-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol), and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated using chloroform and water and distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9 g of compound subCB-2 (yield 73%, MS: [M+H]+ = 428).

[0403]

[0404] Under a nitrogen atmosphere, compound subCB-2 (15 g, 35.1 mmol) and Trz13 (13.8 g, 35.1 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g, 105.3 mmol) was dissolved in 44 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.6 g of compound 1-11 (yield 72%, MS: [M+H]+ = 659).

[0405] Preparation Example 1-12

[0406]

[0407] Under a nitrogen atmosphere, compound subCB-1 (15 g, 36.5 mmol) and Trz14 (14.7 g, 36.5 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (15.1 g, 109.4 mmol) was dissolved in 45 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17 g of compound 1-12 (yield 71%, MS: [M+H]+ = 659).

[0408] Preparation Example 1-13

[0409]

[0410] Under a nitrogen atmosphere, compound CE (15 g, 51 mmol) and dibenzo[b,d]furan-1-ylboronic acid (10.8 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.7 g of compound subCE-1 (yield 63%, MS: [M+H]+ = 426).

[0411]

[0412] Under a nitrogen atmosphere, compound subCE-1 (15 g, 35.2 mmol) and Trz15 (12.4 g, 35.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g, 105.7 mmol) was dissolved in 44 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.2 g of compound 1-13 (yield 62%, MS: [M+H]+ = 699).

[0413] Preparation Example 1-14

[0414]

[0415] Under a nitrogen atmosphere, compound CF (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9 g of compound subCF-1 (yield 76%, MS: [M+H]+ = 386).

[0416]

[0417] Under a nitrogen atmosphere, compound subCF-1 (15 g, 38.9 mmol) and Trz5 (15.7 g, 38.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.6 mmol) was dissolved in 48 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of compound 1-14 (yield 66%, MS: [M+H]+ = 709).

[0418] Preparation Example 1-15

[0419]

[0420] Under a nitrogen atmosphere, compound DA (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6 g of compound subDA-1 (yield 68%, MS: [M+H]+ = 336).

[0421]

[0422] Under a nitrogen atmosphere, to 300 ml of 1,4-di ane, compound subDA-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added, and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. After a reaction for 7 hours, it was cooled to room temperature. Then, the organic layer was separated using chloroform and water and distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of compound subDA-2 (yield 70%, MS: [M+H]+ = 428).

[0423]

[0424] Under a nitrogen atmosphere, compound subDA-2 (15 g, 35.1 mmol) and Trz17 (13.8 g, 35.1 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g, 105.3 mmol) was dissolved in 44 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.6 g of compound 1-15 (yield 63%, MS: [M+H]+ = 659).

[0425] Preparation Example 1-16

[0426]

[0427] Under a nitrogen atmosphere, compound DB (15 g, 51 mmol) and naphthalen-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of compound subDB-1 (yield 68%, MS: [M+H]+ = 386).

[0428]

[0429] Under a nitrogen atmosphere, to 300 ml of 1,4-di Compound subDB-1 (15 g, 39 mmol) and bis(pinacolato)diboron (10.9 g, 42.9 mmol) were added to an alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.7 g, 58.5 mmol) was added and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.3 mmol) were added. After a reaction for 7 hours, it was cooled to room temperature. Then, the organic layer was separated using chloroform and water and distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9 g of compound subDB-2 (yield 75%, MS: [M+H]+ = 478).

[0430]

[0431] Compound subDB-2 (15 g, 31.4 mmol) and Trz2 (8.4 g, 31.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (13 g, 94.3 mmol) was dissolved in 39 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After a reaction for 11 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13 g of compound 1-16 (yield 71%, MS: [M+H]+ = 583).

[0432] Preparation Example 1-17

[0433]

[0434] Under a nitrogen atmosphere, compound DF (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g of compound subDF-1 (yield 65%, MS: [M+H]+ = 336).

[0435]

[0436] Under a nitrogen atmosphere, compound subDF-1 (15 g, 44.7 mmol) and Trz18 (18 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of compound 1-17 (yield 62%, MS: [M+H]+ = 659).

[0437] Preparation Example 2-1

[0438]

[0439] Under a nitrogen atmosphere, compound AA (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.3 g of compound subAA-3 (yield 77%, MS: [M+H]+ = 370).

[0440]

[0441] Under a nitrogen atmosphere, compound subAA-3 (10 g, 27 mmol), compound amine 1 (9.1 g, 27 mmol) and sodium tert-butoxide (8.6 g, 40.6 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.8 g of compound 2-1 (yield 60%, MS: [M+H]+ = 669).

[0442] Preparation Example 2-2

[0443]

[0444] Under a nitrogen atmosphere, compound subAB-1 (10 g, 31.3 mmol), compound amine 2 (9.2 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9 g of compound 2-2 (yield 66%, MS: [M+H]+ = 579).

[0445] Preparation Example 2-3

[0446]

[0447] Under a nitrogen atmosphere, compound AC (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1 g of compound subAC-1 (yield 76%, MS: [M+H]+ = 320).

[0448]

[0449] Under a nitrogen atmosphere, compound subAC-1 (10 g, 31.3 mmol), compound amine 3 (12.8 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15 g of compound 2-3 (yield 69%, MS: [M+H]+ = 694).

[0450] Preparation Example 2-4

[0451]

[0452] Under a nitrogen atmosphere, compound subAC-1 (15 g, 46.9 mmol) and compound amine 4 (22.8 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 10 hours of reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.1 g of compound 2-4 (yield 68%, MS: [M+H]+ = 725).

[0453] Preparation Example 2-5

[0454]

[0455] Under a nitrogen atmosphere, compound AE (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.7 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17 g of compound subAE-2 (yield 80%, MS: [M+H]+ = 396).

[0456]

[0457] Under a nitrogen atmosphere, compound subAE-2 (10 g, 25.3 mmol), compound amine 5 (7.5 g, 25.3 mmol) and sodium tert-butoxide (8 g, 37.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.3 g of compound 2-5 (yield 50%, MS: [M+H]+ = 655).

[0458] Preparation Example 2-6

[0459]

[0460] Under a nitrogen atmosphere, compound AF (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.7 g of compound subAF-2 (yield 74%, MS: [M+H]+ = 320).

[0461]

[0462] Under a nitrogen atmosphere, compound subAF-2 (15 g, 46.9 mmol) and compound amine 6 (20.7 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.1 g of compound 2-6 (yield 63%, MS: [M+H]+ = 681).

[0463] Preparation Example 2-7

[0464]

[0465] Under a nitrogen atmosphere, compound subBA-1 (15 g, 46.9 mmol) and compound amine 10 (18.5 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.2 g of compound 2-7 (yield 78%, MS: [M+H]+ = 635).

[0466] Preparation Example 2-8

[0467]

[0468] Under a nitrogen atmosphere, compound subBB-1 (15 g, 46.9 mmol) and compound amine 11 (23.1 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.7 g of compound 2-8 (yield 78%, MS: [M+H]+ = 731).

[0469] Preparation Example 2-9

[0470]

[0471] Under a nitrogen atmosphere, compound subBB-1 (10 g, 31.3 mmol), compound amine 12 (13.3 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound 2-9 (yield 60%, MS: [M+H]+ = 703).

[0472] Preparation Example 2-10

[0473]

[0474] Under a nitrogen atmosphere, compound BC (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After an 11-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.1 g of compound subBC-1 (yield 76%, MS: [M+H]+ = 370).

[0475]

[0476] In a nitrogen atmosphere, compound subBC-1 (10 g, 27 mmol), compound amine 13 (8.7 g, 27 mmol) and sodium tert-butoxide (8.6 g, 40.6 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of compound 2-10 (yield 51%, MS: [M+H]+ = 655).

[0477] Preparation Example 2-11

[0478]

[0479] In a nitrogen atmosphere, compound BC (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After an 11-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.4 g of compound subBC-2 (yield 78%, MS: [M+H]+ = 320).

[0480]

[0481] Under a nitrogen atmosphere, compound subBC-2 (15 g, 46.9 mmol) and compound amine 14 (17.8 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.5 g of compound 2-11 (yield 74%, MS: [M+H]+ = 619).

[0482] Preparation Example 2-12

[0483]

[0484] Under a nitrogen atmosphere, compound BC (15 g, 53.9 mmol) and dibenzo[b,d]furan-1-ylboronic acid (11.4 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9 g of compound subBC-3 (yield 63%, MS: [M+H]+ = 410).

[0485]

[0486] Under a nitrogen atmosphere, compound subBC-3 (15 g, 36.6 mmol) and compound amine 15 (16.2 g, 36.6 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (15.2 g, 109.8 mmol) was dissolved in 46 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a 12-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.3 g of compound 2-12 (yield 65%, MS: [M+H]+ = 771).

[0487] Preparation Example 2-13

[0488]

[0489] Under a nitrogen atmosphere, compound BE (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a 12-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1 g of compound subBE-2 (yield 76%, MS: [M+H]+ = 320).

[0490]

[0491] Under a nitrogen atmosphere, compound subBE-2 (10 g, 31.3 mmol), compound amine 16 (10.8 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13 g of compound 2-13 (yield 66%, MS: [M+H]+ = 629).

[0492] Preparation Example 2-14

[0493]

[0494] Under a nitrogen atmosphere, compound subBE-2 (15 g, 46.9 mmol) and compound amine 17 (21.4 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After a 10-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.4 g of compound 2-14 (yield 72%, MS: [M+H]+ = 695).

[0495] Preparation Example 2-15

[0496]

[0497] Under a nitrogen atmosphere, compound subBF-1 (15 g, 46.9 mmol) and compound amine 18 (22.1 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.3 g of compound 2-15 (yield 70%, MS: [M+H]+ = 711).

[0498] Preparation Example 2-16

[0499]

[0500] Under a nitrogen atmosphere, compound CA (15 g, 51 mmol) and dibenzo[b,d]thiophen-3-ylboronic acid (11.6 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a 9-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.4 g of compound subCA-2 (yield 64%, MS: [M+H]+ = 442).

[0501]

[0502] Under a nitrogen atmosphere, compound subCA-2 (15 g, 33.9 mmol) and compound amine 22 (14.1 g, 33.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.1 g, 101.8 mmol) was dissolved in 42 ml of water and then added thereto. Thereafter, it was stirred well, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.8 g of compound 2-16 (yield 79%, MS: [M+H]+ = 777).

[0503] Preparation Example 2-17

[0504]

[0505] Under a nitrogen atmosphere, compound subCB-1 (10 g, 29.8 mmol), compound amine 23 (12.6 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.5 g of compound 2-17 (yield 58%, MS: [M+H]+ = 722).

[0506] Preparation Example 2-18

[0507]

[0508] Under a nitrogen atmosphere, compound subCB-1 (15 g, 44.7 mmol) and compound amine 24 (21.1 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.1 g of compound 2-18 (yield 62%, MS: [M+H]+ = 727).

[0509] Preparation Example 2-19

[0510]

[0511] Under a nitrogen atmosphere, compound CC (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 8 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.9 g of compound subCC-1 (yield 64%, MS: [M+H]+ = 336).

[0512]

[0513] Under a nitrogen atmosphere, compound subCC-1 (10 g, 29.8 mmol), compound amine 25 (12.3 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14 g of compound 2-19 (yield 66%, MS: [M+H]+ = 711).

[0514] Preparation Example 2-20

[0515]

[0516] Under a nitrogen atmosphere, compound subCC-1 (10 g, 29.8 mmol), compound amine 26 (11.1 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12 g of compound 2-20 (yield 60%, MS: [M+H]+ = 671).

[0517] Preparation Example 2-21

[0518]

[0519] Under a nitrogen atmosphere, compound subCC-1 (10 g, 29.8 mmol), compound amine 27 (14.6 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.8 g of compound 2-21 (yield 53%, MS: [M+H]+ = 747).

[0520] Preparation Example 2-22

[0521]

[0522] Under a nitrogen atmosphere, compound CD (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a 10-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8 g of compound subCD-1 (yield 75%, MS: [M+H]+ = 336).

[0523]

[0524] Under a nitrogen atmosphere, compound subCD-1 (15 g, 44.7 mmol) and compound amine 28 (19.7 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.2 g of compound 2-22 (yield 65%, MS: [M+H]+ = 697).

[0525] Preparation Example 2-23

[0526]

[0527] Under a nitrogen atmosphere, compound CE (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 12 hours of reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.5 g of compound subCE-2 (yield 79%, MS: [M+H]+ = 336).

[0528]

[0529] Under a nitrogen atmosphere, compound subCE-2 (10 g, 29.8 mmol), compound amine 29 (10.3 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.9 g of compound 2-23 (yield 62%, MS: [M+H]+ = 645).

[0530] Preparation Example 2-24

[0531]

[0532] Under a nitrogen atmosphere, compound CF (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction of 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.6 g of compound subCF-2 (yield 68%, MS: [M+H]+ = 336).

[0533]

[0534] Under a nitrogen atmosphere, compound subCF-2 (10 g, 29.8 mmol), compound amine 30 (10.5 g, 29.8 mmol), and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.4 g of compound 2-24 (yield 64%, MS: [M+H]+ = 651).

[0535] Preparation Example 2-25

[0536]

[0537] Under a nitrogen atmosphere, compound subDB-1 (15 g, 38.9 mmol) and compound amine 33 (17.2 g, 38.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.6 mmol) was dissolved in 48 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.2 g of compound 2-25 (yield 73%, MS: [M+H]+ = 747).

[0538] Preparation Example 2-26

[0539]

[0540] Under a nitrogen atmosphere, compound DB (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 10 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound subDB-2 (yield 77%, MS: [M+H]+ = 336).

[0541]

[0542] Under a nitrogen atmosphere, compound subDB-2 (10 g, 31.3 mmol), compound amine 34 (12.9 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15 g of compound 2-26 (yield 69%, MS: [M+H]+ = 695).

[0543] Production Example 2-27

[0544]

[0545] Under a nitrogen atmosphere, compound DC (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well, and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After an 8-hour reaction, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.8 g of compound subDC-1 (yield 65%, MS: [M+H]+ = 386).

[0546]

[0547] Under a nitrogen atmosphere, compound subDC-1 (10 g, 25.9 mmol), compound amine 13 (8.3 g, 25.9 mmol) and sodium tert-butoxide (8.3 g, 38.9 mmol) were added to 200 ml of xylene, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 2 hours, the reaction was completed, and after cooling to room temperature, the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.9 g of compound 2-27 (yield 63%, MS: [M+H]+ = 671).

[0548] Preparation Example 2-28

[0549]

[0550] Under a nitrogen atmosphere, compound DC (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.1 g of compound subDC-2 (yield 65%, MS: [M+H]+ = 336).

[0551]

[0552] Under a nitrogen atmosphere, compound subDC-2 (15 g, 44.7 mmol) and compound amine 7 (21 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (18.5 g, 134 mmol) was dissolved in 56 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 8 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21 g of compound 2-28 (yield 65%, MS: [M+H]+ = 725).

[0553] Preparation Example 2-29

[0554]

[0555] Under a nitrogen atmosphere, compound DE (15 g, 51 mmol) and dibenzo[b,d]furan-2-ylboronic acid (10.8 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction for 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16 g of compound subDE-1 (yield 74%, MS: [M+H]+ = 426).

[0556]

[0557] Under a nitrogen atmosphere, compound subDE-1 (15 g, 35.2 mmol) and compound amine 35 (17.3 g, 35.2 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (14.6 g, 105.7 mmol) was dissolved in 44 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After a reaction for 9 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.7 g of compound 2-29 (yield 67%, MS: [M+H]+ = 837).

[0558] Preparation Example 2-30

[0559]

[0560] Under a nitrogen atmosphere, compound DF (15 g, 51 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.1 g, 51 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (21.1 g, 153 mmol) was dissolved in 63 ml of water and then added thereto. Thereafter, it was stirred well and then tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After a reaction of 12 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.5 g of compound subDF-2 (yield 74%, MS: [M+H]+ = 412).

[0561]

[0562] Under a nitrogen atmosphere, compound subDF-2 (15 g, 57.8 mmol) and compound amine 35 (28.4 g, 57.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Then, potassium carbonate (23.9 g, 173.3 mmol) was dissolved in 72 ml of water and then added thereto. Thereafter, it was stirred well and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After a reaction of 8 hours, it was cooled to room temperature. Then, the organic layer was separated from the aqueous layer, and then the organic layer was distilled. Then, it was dissolved again in chloroform and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.4 g of compound 2-30 (yield 62%, MS: [M+H]+ = 823).

[0563] [Example]

[0564] Comparative Example A

[0565] Coated with a thickness of The ITO (indium tin oxide) glass substrate for the thin film was placed in distilled water containing a detergent and ultrasonically cleaned. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes using distilled water. After cleaning with distilled water was completed, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum depositor.

[0566] A hole injection layer was formed on the prepared ITO transparent electrode with the following compound HI-1 to the thickness, and the following compound A-1 was p-doped at a concentration of 1.5 wt%. Then, the compound HT-1 was vacuum deposited on the hole injection layer to the thickness to form a hole transport layer. Thereafter, the following compound EB-1 was vacuum deposited on the hole transport layer to the thickness as an electron blocking layer. Then, the following compound RH-1 and compound Dp-7 were vacuum deposited on the EB-1 deposited film at a weight ratio of 98:2 to the thickness to form a red light-emitting layer. By vacuum depositing the following compound HB-1 on the light-emitting layer to the thickness, a hole blocking layer was formed. Then, the following compound ET-1 and the following compound LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 2:1 to the thickness to form an electron injection and transport layer. Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron injection and transport layer to thicknesses of and respectively to form a cathode.

[0567]

[0568] In the above process, the deposition rate of the organic material was maintained at / second to / second, the deposition rate of lithium fluoride of the cathode was maintained at / second, and the deposition rate of aluminum was maintained at / second. In addition, the vacuum degree during deposition was maintained at 2×10 -7 Torr to 5×10 -6 Torr, thereby manufacturing an organic light-emitting device.

[0569] Examples 1 to 17

[0570] An organic light-emitting device was fabricated in the same manner as in Comparative Example A, except that the compound shown in Table 1 was used instead of the compound RH-1 which was the host in the organic light-emitting device of Comparative Example A.

[0571] Comparative Examples 1 to 7

[0572] An organic light-emitting device was fabricated in the same manner as in Comparative Example A, except that the compound shown in Table 1 was used instead of the compound RH-1 which was the host in the organic light-emitting device of Comparative Example A. The structures of Compounds B-8 to B-14 in Table 1 are as follows.

[0573]

[0574] Examples 18 to 47

[0575] An organic light-emitting device was fabricated in the same manner as in Comparative Example A, except that the compound shown in Table 2 was used instead of the compound EB-1 which was the electron blocking layer material in the organic light-emitting device of Comparative Example A.

[0576] Comparative Examples 8 to 14

[0577] An organic light-emitting device was fabricated in the same manner as in Comparative Example A, except that the compound shown in Table 2 was used instead of the compound EB-1 which was the electron blocking layer material in the organic light-emitting device of Comparative Example A. The structures of Compounds B-1 to B-7 in Table 2 are as follows.

[0578]

[0579] Examples 48 to 115

[0580] An organic light-emitting device was fabricated in the same manner as in Comparative Example A, except that the compounds of the first host and the second host described in Table 3 were used in a weight ratio of 1:1 instead of the compound RH-1 which was the host in the organic light-emitting device of Comparative Example A.

[0581] [Experimental Example]

[0582] The driving voltage and efficiency (based on 15 mA / cm 2 ) were measured by applying a current to the organic light-emitting devices prepared in Examples 1 to 115, Comparative Example A, and Comparative Examples 1 to 14 above, and the results are shown in Tables 1 to 3. The lifetime T95 means the time taken until the initial brightness (7,000 nits) is reduced to 95%.

[0583] [Table 1]

[0584]

[0585] [Table 2]

[0586]

[0587]

[0588] [Table 3]

[0589]

[0590]

[0591]

[0592] When a current was applied to the organic light emitting devices fabricated in Examples 1 to 115 and Comparative Examples 1 to 14, the results shown in Tables 1 to 3 were obtained.

[0593] It was determined that when Compounds 1-1 to 1-17 of the present disclosure were used as the red host, compared with the case of using the compounds of the comparative examples shown in Table 1, the driving voltage was reduced and the efficiency and lifetime were improved. Even when Compounds 2-1 to 2-30 of the present disclosure were used as the electron blocking layer, compared with the case of using the compounds of the comparative examples shown in Table 2, the driving voltage was also reduced and the efficiency and lifetime were also improved.

[0594] In addition, in Table 3, when one of Compounds 1-1 to 1-17 was selected as the first host and one of Compounds 2-1 to 2-30 was used as the second host, and they were used as the red host by co-deposition, compared with the case of using a single material host, the driving voltage was reduced and the efficiency and lifetime were improved.

[0595] That is, from the results of Tables 1 to 3, it was determined that when the compounds of one embodiment were used as the host of the red light emitting layer or as the electron blocking layer in the red device, the driving voltage, luminous efficiency, and lifetime characteristics of the organic light emitting device could be improved.

[0596] [Explanation of Reference Numerals]

[0597] 1: Substrate 2: Anode

[0598] 3: Light emitting layer 4: Cathode

[0599] 5: Hole injection layer 6: Hole transport layer

[0600] 7: Electron blocking layer 8: Hole blocking layer

[0601] 9: Electron injection and transport layer

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, A is a thiazole ring fused to an adjacent ring, L1 is a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C 2-60 heteroarylene, R1 is Ar1 to Ar4 are each independently a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from N, O, and S, L2 to L5 are each independently a single bond; a substituted or unsubstituted C 6-60 arylene; or a substituted or unsubstituted C 2-60 heteroarylene containing at least one selected from N, O, and S, R2 is a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl containing at least one selected from N, O and S, D is deuterium, and n is an integer of 0 or greater and 5 or less.

2. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-2 and 1-4: [Chemical Formula 1-2] [Chemical Formula 1-4] In Chemical Formulas 1-2 and 1-4, R1, R2, L1, D, and n are as defined in claim 1.

3. The compound according to claim 1, wherein L1 is a single bond, phenylene, biphenyldiyl, or naphthalenediyl.

4. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl.

5. The compound according to claim 1, wherein Ar3 and Ar4 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, or phenylnaphthyl.

6. The compound according to claim 1, wherein L2 and L3 are each independently a single bond, phenylene, or naphthalenediyl.

7. The compound according to claim 1, wherein L4 and L5 are each independently a single bond, phenylene, biphenyldiyl, naphthylenediyl, or carbazolediyl.

8. The compound according to claim 1, wherein at least one of Ar1 and Ar2 is a substituted or unsubstituted C 6-60 aryl.

9. The compound according to claim 1, wherein at least one of Ar3 and Ar4 is a substituted or unsubstituted C 6-60 aryl.

10. The compound according to claim 1, wherein R2 is phenyl, biphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.

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

12. 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 disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains at least one compound according to any one of claims 1 to 11.

13. The organic light-emitting device according to claim 12, wherein the organic material layer is a light-emitting layer or an electron blocking layer.

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