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. Disclosed is a compound represented by the following Chemical Formula 1: [Chemical Formula 1] # imgabs0 #. The compound represented by Chemical Formula 1 can be used as a material of an organic material layer of an organic light-emitting device, and can improve efficiency, achieve a low driving voltage, and / or improve lifespan characteristics in the organic light-emitting device.

Description

[0001] This application is a divisional application of the Chinese patent application with the application date of December 17, 2021, application number "202180055332.8", and invention name "New compounds and organic light-emitting devices containing the same". Technical Field

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

[0003] Generally speaking, organic light emitting diodes (OLEDs) are a type of organic light emitting diode (OLED) that converts electrical energy into light energy using organic materials. These devices have been extensively researched due to their wide viewing angles, excellent contrast, fast response time, excellent brightness, driving voltage, and response speed.

[0004] Organic light-emitting devices typically have a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer typically has a multilayer structure containing different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0005] There is an ongoing need to develop new organic materials for use in organic light emitting devices as described above.

[0006] Prior art literature

[0007] Patent Literature

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

[0009] Technical issues

[0010] The present disclosure relates to new organic light-emitting materials and organic light-emitting devices including 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 Azole ring,

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

[0018] R1 is

[0019] Ar1 to Ar4 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 heteroaryl,

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

[0021] R2 is 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 more and 5 or less.

[0024] In addition, an organic light-emitting device is provided, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged 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.

[0025] Beneficial effects

[0026] The compound represented by Chemical Formula 1 can be used as a material for an organic material layer of an organic light-emitting device, and can improve efficiency, achieve a low driving voltage, and / or improve lifespan characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a material for hole injection, hole transport, luminescence, electron transport, or electron injection. BRIEF 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 in this article, the notation It refers to the bond to another substituent.

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

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

[0034]

[0035] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a substituent having the following structural formula, but is not limited thereto.

[0036]

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

[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 and the like, but is not limited thereto.

[0041] In the present disclosure, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

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

[0043] In the present disclosure, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0044] In the present disclosure, the alkenyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0045] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0046] In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but not limited thereto.

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

[0048] In the present disclosure, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as a heteroatom, and its carbon number is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but are not limited thereto.

[0049] In the present disclosure, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine groups is the same as the aforementioned example of the aryl group. In the present disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the aforementioned example of the alkyl group. In the present disclosure, the heteroaryl group in heteroarylamine can be applied to the aforementioned description of the heteroaryl group. In the present disclosure, the alkenyl group in aralkenyl groups is the same as the aforementioned example of the alkenyl group. In the present disclosure, the aforementioned description of the aryl group can be applied, except that the arylene group is a divalent group. In the present disclosure, the aforementioned description of the heteroaryl group can be applied, except that the heteroarylene group is a divalent group. In the present disclosure, the aforementioned description of the aryl group or cycloalkyl group can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the aforementioned description of the heteroaryl group can be applied, except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

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

[0051] [Chemical Formula 1-1]

[0052]

[0053] [Chemical formula 1-2]

[0054]

[0055] [Chemical formula 1-3]

[0056]

[0057] [Chemical formula 1-4]

[0058]

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

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

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

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

[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.

[0066] More preferably, Ar1 and Ar2 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[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.

[0070] More preferably, Ar3 and Ar4 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phenylcarbazolyl group, or a phenylnaphthyl group.

[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 may each independently be a single bond, a phenylene group, a biphenyldiyl group, or a naphthalenediyl group.

[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; substituted or unsubstituted C 6-20 Arylene; or a substituted or unsubstituted C containing at least one selected from N, O and S 2-20 Heteroarylene.

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

[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 may be a substituted or unsubstituted C 6-60 Aryl, more preferably, at least one of Ar1 and Ar2 may be a substituted or unsubstituted C 6-20 Aryl, more preferably, at least one of Ar1 and Ar2 may be an unsubstituted C 6-20 The aryl group, and most preferably, at least one of Ar1 and Ar2 may be a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

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

[0083] At the same time, R2 is a substituent of ring A.

[0084] Preferably, R2 can be substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 Heteroaryl.

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

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

[0087]

[0088] Preferably, n is an integer of 0.

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

[0090]

[0091]

[0092]

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[0355] In chemical formula 1, L1 is a single bond and R1 is The compound can be prepared by the preparation method shown in the following Reaction Scheme 1. Some compounds can be prepared by the preparation method shown in the following Reaction Scheme 2, and other compounds can be prepared similarly.

[0356] [Reaction Scheme 1]

[0357]

[0358] [Reaction Scheme 2]

[0359]

[0360] In Reaction Schemes 1 and 2, R1, R2, L1, L4, L5, Ar3, Ar4, 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.

[0361] 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 used 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 used for the Suzuki coupling reaction can be varied as known in the art. The preparation method can be described in more detail in the following preparation examples.

[0362] In addition, an organic light-emitting device including the compound represented by Chemical Formula 1 is provided. As an example, an organic light-emitting device including: a first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes at least one compound represented by Chemical Formula 1.

[0363] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers.

[0364] In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 1.

[0365] In addition, the organic material layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes, and the hole transport layer, the hole injection layer, or the hole transport and injection layer may include the compound represented by Chemical Formula 1.

[0366] In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.

[0367] In addition, the organic light emitting device according to the present disclosure may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present disclosure may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to one embodiment of the present disclosure is shown in FIG. Figure 1 middle.

[0368] 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 is shown, 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. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer or the electron blocking layer.

[0369] The organic light-emitting device according to the present disclosure can be manufactured using materials and methods known in the art, except that one or more of the organic material layers contains the compound represented by Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0370] For example, an organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can serve as a cathode on the organic material layer. In addition to such a method, an 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.

[0371] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer by a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0372] In addition to such a method, an 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 preparation method is not limited thereto.

[0373] 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.

[0374] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0375] As the cathode material, a material with a small work function is generally preferred, so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like.

[0376] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, so it has a hole injection effect in the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents the 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. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, but are not limited thereto.

[0377] 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 preferably a material with a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples include, but are not limited to, organic materials based on arylamines, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0378] The electron blocking layer is 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 and not recombining in the light-emitting layer. It is also called an electron suppression layer. For the electron blocking layer, a material with a lower electron affinity than that of the electron transport layer is preferred. Preferably, the material represented by Chemical Formula 1 of the present disclosure can be used as the electron blocking material.

[0379] 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, to combine them, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylvinyl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based compounds; azole-, benzothiazole-, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0380] 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, or the like. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, 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, their weight ratio is 10:90 to 90:10, and more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0381] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, Styrylamine compounds are compounds in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino are substituted or unsubstituted. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0382] For example, at least one selected from the following may be used as the dopant material, but the present disclosure is not limited thereto:

[0383]

[0384]

[0385]

[0386] The hole blocking layer is 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 and not being recombined in the light emitting layer.

[0387] The electron transport layer is a layer that accepts electrons from the electron injection layer and transports the electrons to the light-emitting layer. As an 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 free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the relevant art. In particular, suitable examples of cathode materials are typical materials with low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0388] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an excellent effect of injecting electrons from the cathode and injecting electrons into the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, etc., and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0389] Examples of metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, bis(2-methyl-8-quinolinato)(2-naphthol)gallium, and the like, but are not limited thereto.

[0390] Meanwhile, the “electron injection and transport layer” used herein is a layer that functions as both an electron injection layer and an electron transport layer, and materials for each layer may be used alone or in combination, but the present disclosure is not limited thereto.

[0391] The organic light emitting device according to the present disclosure may be a bottom emission device, a top emission device, or a double-sided emission device, and in particular, may be a bottom emission device requiring relatively high light emission efficiency.

[0392] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

[0393] The preparation of the compound represented by Chemical Formula 1 and the organic light-emitting device including the same will be described in detail in the following examples. However, these examples are provided for illustrative purposes only and are not intended to limit the scope of the present disclosure.

[0394] [Preparation Example]

[0395] Preparation Example 1-1

[0396]

[0397] Compound AA (15 g, 56.2 mmol) and [1,1'-biphenyl]-4-boronic acid (11.1 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.2 g of compound subAA-1 (yield 64%, MS: [M+H] + = 396).

[0398]

[0399] 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-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.6 g, 56.8 mmol) was added and stirred thoroughly, 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 6 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.8 g of compound subAA-2 (yield 75%, MS: [M+H] + = 488).

[0400]

[0401] Compound subAA-2 (15 g, 30.8 mmol) and compound Trz1 (12.1 g, 30.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.8 g, 92.3 mmol) was then dissolved in 38 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 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 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 17.2 g of compound 1-1 (yield 78%, MS: [M+H] + = 719).

[0402] Preparation Example 1-2

[0403]

[0404] Compound AA (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was then added. After reacting 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 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 g of compound subAA-3 (yield 67%, MS: [M+H] + = 320).

[0405]

[0406] Compound subAA-3 (15 g, 46.9 mmol) and compound Trz2 (18.9 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 23.8 g of compound 1-2 (yield 79%, MS: [M+H] + = 643).

[0407] Preparation Examples 1-3

[0408]

[0409] Compound AB (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added thereto. 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAB-1 (yield 76%, MS: [M+H] + = 320).

[0410]

[0411] Compound subAB-1 (15 g, 46.9 mmol) and compound Trz3 (18.9 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, 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 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 19.9 g of compound 1-3 (yield 66%, MS: [M+H] + = 643).

[0412] Preparation Examples 1-4

[0413]

[0414] Compound subAB-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol). After reacting for 5 hours, the mixture 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, and 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 subAB-2 (yield 65%, MS: [M+H] + = 412).

[0415]

[0416] Compound subAB-2 (15 g, 46.9 mmol) and compound Trz4 (17.3 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 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 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 17.6 g of compound 1-4 (yield 61%, MS: [M+H] + = 617).

[0417] Preparation Examples 1-5

[0418]

[0419] Compound AC (15 g, 56.2 mmol) and naphthalene-2-ylboronic acid (9.7 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added thereto. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.5 g of compound subAC-1 (yield 70%, MS: [M+H]+=370).

[0420]

[0421] Compound subAC-1 (15 g, 40.6 mmol) and bis(pinacolato)diboron (11.3 g, 44.6 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Potassium acetate (6 g, 60.8 mmol) was then added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol). After reacting for 10 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then dissolved in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAC-2 (yield 60%, MS: [M+H] + = 462).

[0422]

[0423] Compound subAC-2 (15 g, 40.6 mmol) and compound Trz1 (16 g, 40.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.8 g of compound 1-5 (yield 60%, MS: [M+H]+=693).

[0424] Preparation Examples 1-6

[0425]

[0426] Compound AD (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was then distilled. It was then 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 11.1 g of compound subAD-1 (yield 62%, MS: [M+H] + = 320).

[0427]

[0428] Compound subAD-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Potassium acetate (6.9 g, 70.4 mmol) was then added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium (0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol). After reacting for 5 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 12.5 g of compound subAD-2 (yield 65%, MS: [M+H] + = 412).

[0429]

[0430] Compound subAD-2 (15 g, 46.9 mmol) and compound Trz5 (12.6 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, 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 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 17.7 g of compound 1-6 (yield 73%, MS: [M+H] + = 517).

[0431] Preparation Examples 1-7

[0432]

[0433] Under a nitrogen atmosphere, compound subAD-2 (15 g, 46.9 mmol) and compound Trz6 (16.8 g, 46.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, 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 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 21.6 g of compound 1-7 (yield 76%, MS: [M+H] + = 607).

[0434] Preparation Examples 1-8

[0435]

[0436] Compound subAD-1 (15 g, 36.5 mmol) and compound Trz7 (18 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, 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 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 19.8 g of compound 1-8 (yield 74%, MS: [M+H] + = 733).

[0437] Preparation Examples 1-9

[0438]

[0439] Compound subAD-1 (15 g, 46.9 mmol) and compound Trz8 (18.9 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 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 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 19.3 g of compound 1-9 (yield 64%, MS: [M+H] + = 643).

[0440] Preparation Example 1-10

[0441]

[0442] Compound subAD-2 (15 g, 36.5 mmol) and compound Trz9 (14.7 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 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 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 14.1 g of compound 1-10 (yield 60%, MS: [M+H] + = 643).

[0443] Preparation Example 1-11

[0444]

[0445] Compound AD (15 g, 56.2 mmol) and dibenzo[b,d]thiophene-4-ylboronic acid (12.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 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 17.7 g of compound subAD-3 (yield 74%, MS: [M+H]+=426).

[0446]

[0447] Compound subAD-3 (15 g, 35.2 mmol) and bis(pinacolato)diboron (9.8 g, 38.7 mmol) were added to 300 ml of 1,4-diborane under nitrogen atmosphere. The mixture was stirred and refluxed in oxane. Potassium acetate (5.2 g, 52.8 mmol) was then added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium (0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol). After reacting for 8 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 subAD-4 (yield 68%, MS: [M+H] + = 519).

[0448]

[0449] Compound subAD-4 (15 g, 35.2 mmol) and compound Trz5 (9.4 g, 35.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.7 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 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 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 16.7 g of compound 1-11 (yield 76%, MS: [M+H] + = 623).

[0450] Preparation Example 1-12

[0451]

[0452] Compound AE (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.9 g of compound subAE-1 (yield 72%, MS: [M+H] + = 320).

[0453]

[0454] Compound subAE-1 (15 g, 46.9 mmol) and compound Trz10 (21.3 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, 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 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 22.1 g of compound 1-12 (yield 68%, MS: [M+H]+=693).

[0455] Preparation Example 1-13

[0456]

[0457] Compound AE (15 g, 56.2 mmol) and naphthalene-2-ylboronic acid (9.7 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added thereto. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAE-2 (yield 80%, MS: [M+H]+=370).

[0458]

[0459] Compound subAE-2 (15 g, 40.6 mmol) and bis(pinacolato)diboron (11.3 g, 44.6 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Then, potassium acetate (6 g, 60.8 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol). After reacting for 10 hours, the mixture 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, and 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 subAE-3 (yield 60%, MS: [M+H] + = 462).

[0460]

[0461] Compound subAE-3 (15 g, 32.5 mmol) and compound Trz11 (15.6 g, 32.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (13.5 g, 97.6 mmol) was then dissolved in 40 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 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, and 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 1-13 (yield 79%, MS: [M+H]+=769).

[0462] Preparation Example 1-14

[0463]

[0464] Compound AF (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added thereto. 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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-1 (yield 71%, MS: [M+H] + = 320).

[0465]

[0466] Compound subAF-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol). After reacting for 5 hours, the mixture 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, and 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 subAF-2 (yield 65%, MS: [M+H] + = 412).

[0467]

[0468] Compound subAF-2 (15 g, 46.9 mmol) and compound Trz12 (18.5 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting 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 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 19.6 g of compound 1-14 (yield 65%, MS: [M+H] + = 643).

[0469] Preparation Example 1-15

[0470]

[0471] Compound AF (15 g, 56.2 mmol) and [1,1'-biphenyl]-4-boronic acid (11.1 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.4 g of compound subAF-3 (yield 74%, MS: [M+H] + = 396).

[0472]

[0473] Compound subAF-3 (15 g, 37.9 mmol) and bis(pinacolato)diboron (10.6 g, 41.7 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Potassium acetate (5.6 g, 56.8 mmol) was then added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.3 mmol). After reacting for 8 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 g of compound subAF-4 (yield 76%, MS: [M+H] + = 488).

[0474]

[0475] Compound subAF-4 (15 g, 36.5 mmol) and compound Trz13 (14.4 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, 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 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 16.5 g of compound 1-15 (yield 63%, MS: [M+H] + = 719).

[0476] Preparation Example 1-16

[0477]

[0478] Compound BA (15 g, 56.2 mmol) and dibenzo[b,d]furan-2-ylboronic acid (11.9 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 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 17.9 g of compound subBA-1 (yield 78%, MS: [M+H] + = 410).

[0479]

[0480] Compound subBA-1 (15 g, 36.6 mmol) and bis(pinacolato)diboron (10.2 g, 40.3 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.4 g, 54.9 mmol) was added and stirred thoroughly, followed by addition of bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol). After reacting for 9 hours, cooling to room temperature was carried out. 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 14.7 g of compound subBA-2 (yield 80%, MS: [M+H] + = 502).

[0481]

[0482] Compound subBA-2 (15 g, 29.9 mmol) and compound Trz5 (8 g, 29.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 89.8 mmol) was then dissolved in 37 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.3 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 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 10.9 g of compound 1-16 (yield 60%, MS: [M+H] + = 607).

[0483] Preparation Example 1-17

[0484]

[0485] Compound BA (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 13.6 g of compound subBA-3 (yield 76%, MS: [M+H] + = 320).

[0486]

[0487] Compound subBA-3 (15 g, 46.9 mmol) and compound Trz14 (20.8 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 1-17 (yield 73%, MS: [M+H] + = 683).

[0488] Preparation Example 1-18

[0489]

[0490] Compound BB (15 g, 56.2 mmol) and phenylboronic acid (6.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subBB-1 (yield 61%, MS: [M+H] + = 320).

[0491]

[0492] Compound subBB-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol) were added. After reacting 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, and 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 subBB-2 (yield 79%, MS: [M+H] + = 412).

[0493]

[0494] Compound subBB-2 (15 g, 36.5 mmol) and compound Trz15 (11.6 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.1 g of compound 1-18 (yield 78%, MS: [M+H] + = 567).

[0495] Preparation Example 1-19

[0496]

[0497] Compound BB (15 g, 56.2 mmol) and dibenzo[b,d]furan-1-ylboronic acid (11.9 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.9 g of compound subBB-3 (yield 78%, MS: [M+H]+=410).

[0498]

[0499] Compound subBB-3 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subBB-4 (yield 77%, MS: [M+H] + = 502).

[0500]

[0501] Compound subBB-4 (15 g, 29.9 mmol) and compound Trz5 (8 g, 29.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 89.8 mmol) was then dissolved in 37 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.3 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 1-19 (yield 62%, MS: [M+H] + = 607).

[0502] Preparation Example 1-20

[0503]

[0504] Compound BC (15 g, 56.2 mmol) and dibenzo[b,d]thiophene-4-ylboronic acid (12.8 g, 56.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (23.3 g, 168.5 mmol) was then dissolved in 70 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.6 mmol) was added thereto. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subBC-1 (yield 64%, MS: [M+H]+=426).

[0505]

[0506] Compound subBC-1 (15 g, 35.3 mmol) and bis(pinacolato)diboron (9.8 g, 38.8 mmol) were added to 300 ml of 1,4-diborane under nitrogen atmosphere. The mixture was stirred and refluxed in oxane. Then, potassium acetate (5.2 g, 52.9 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol). After reacting for 5 hours, the mixture 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.5 g of compound subBC-2 (yield 63%, MS: [M+H] + = 518).

[0507]

[0508] Compound subBC-2 (15 g, 29 mmol) and compound Trz5 (7.8 g, 29 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12 g, 87 mmol) was then dissolved in 36 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.3 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 1-20 (yield 80%, MS: [M+H] + = 623).

[0509] Preparation Example 1-21

[0510]

[0511] Compound BD (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Thereafter, it was fully stirred, and 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 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 11.9 g of compound subBD-1 (yield 69%, MS: [M+H] + = 320).

[0512]

[0513] Compound subBD-1 (15 g, 46.9 mmol) and bis(pinacolato)diboron (13.1 g, 51.6 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.9 g, 70.4 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.8 mmol) were added. After reacting for 6 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.2 g of compound subBD-2 (yield 63%, MS: [M+H] + = 412).

[0514]

[0515] Compound subBD-2 (15 g, 36.5 mmol) and compound Trz5 (9.8 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting 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 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 14.7 g of compound 1-21 (yield 78%, MS: [M+H] + = 517).

[0516] Preparation Example 1-22

[0517]

[0518] Compound subBD-2 (15 g, 36.5 mmol) and compound Trz16 (14.7 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 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 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 17.6 g of compound 1-22 (yield 75%, MS: [M+H] + = 643).

[0519] Preparation Example 1-23

[0520]

[0521] Compound subBD-2 (15 g, 36.5 mmol) and compound Trz6 (13.1 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 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 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 17.2 g of compound 1-23 (yield 78%, MS: [M+H] + = 607).

[0522] Preparation Example 1-24

[0523]

[0524] Compound subBD-1 (15 g, 36.5 mmol) and compound Trz9 (14.7 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting 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 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 17.8 g of compound 1-24 (yield 76%, MS: [M+H] + = 643).

[0525] Preparation Example 1-25

[0526]

[0527] Compound subBD-1 (15 g, 36.5 mmol) and compound Trz14 (16.2 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 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 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 16.9 g of compound 1-25 (yield 68%, MS: [M+H] + = 683).

[0528] Preparation Example 1-26

[0529]

[0530] Compound BE (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, it was stirred thoroughly, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subBE-1 (yield 78%, MS: [M+H] + = 320).

[0531]

[0532] Compound subBE-1 (15 g, 46.9 mmol) and compound Trz17 (16.6 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.5 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 20.3 g of compound 1-26 (yield 73%, MS: [M+H] + = 593).

[0533] Preparation Example 1-27

[0534]

[0535] Compound BE (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added thereto. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subBE-2 (yield 63%, MS: [M+H] + = 370).

[0536]

[0537] Compound subBE-2 (15 g, 40.6 mmol) and bis(pinacolato)diboron (11.3 g, 44.6 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Then, potassium acetate (6 g, 60.8 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol). After reacting for 6 hours, the mixture 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, and 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 subBE-3 (yield 67%, MS: [M+H] + = 462).

[0538]

[0539] Compound subBE-3 (15 g, 32.5 mmol) and compound Trz18 (11.6 g, 32.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (13.5 g, 97.5 mmol) was then dissolved in 40 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.3 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.7 g of compound 1-27 (yield 65%, MS: [M+H]+=697).

[0540] Preparation Example 1-28

[0541]

[0542] Compound BF (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, it was fully stirred, and 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 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 11.9 g of compound subBF-1 (yield 69%, MS: [M+H] + = 320).

[0543]

[0544] Compound subBF-1 (15 g, 46.9 mmol) and compound Trz19 (18.9 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 22 g of compound 1-28 (yield 73%, MS: [M+H] + = 643).

[0545] Preparation Example 1-29

[0546]

[0547] Compound BF (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, it was stirred thoroughly, and 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 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 12.3 g of compound subBF-2 (yield 62%, MS: [M+H] + = 370).

[0548]

[0549] Compound subBF-2 (15 g, 40.6 mmol) and bis(pinacolato)diboron (11.3 g, 44.6 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6 g, 60.8 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol). After reacting for 5 hours, cooling to room temperature was performed. 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 13.7 g of compound subBF-3 (yield 73%, MS: [M+H] + = 462).

[0550]

[0551] Compound subBF-3 (15 g, 36.5 mmol) and compound Trz18 (13.1 g, 36.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.4 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting 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 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 1-29 (yield 61%, MS: [M+H] + = 697).

[0552] Preparation Example 1-30

[0553]

[0554] Compound CA (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was then added, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subCA-1 (yield 69%, MS: [M+H] + = 336).

[0555]

[0556] Compound subCA-1 (15 g, 42.2 mmol) and bis(pinacolato)diboron (11.8 g, 46.4 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.2 g, 63.2 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.3 mmol) and tricyclohexylphosphine (0.7 g, 2.5 mmol). After reacting for 8 hours, the mixture 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 11.2 g of compound subCA-2 (yield 62%, MS: [M+H] + = 428).

[0557]

[0558] Compound subCA-2 (15 g, 35.1 mmol) and compound Trz20 (12.6 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting 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 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 16.6 g of compound 1-30 (yield 76%, MS: [M+H] + = 623).

[0559] Preparation Example 1-31

[0560]

[0561] Compound CA (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 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 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 15.3 g of compound subCA-3 (yield 78%, MS: [M+H] + = 386).

[0562]

[0563] Compound subCA-3 (15 g, 38.9 mmol) and compound Trz21 (15.3 g, 38.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 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 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 17.9 g of compound 1-31 (yield 65%, MS: [M+H] + = 709).

[0564] Preparation Example 1-32

[0565]

[0566] Compound CB (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 14.1 g of compound subCB-1 (yield 72%, MS: [M+H] + = 386).

[0567]

[0568] Compound subCB-1 (15 g, 38.9 mmol) and bis(pinacolato)diboron (10.9 g, 42.8 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.7 g, 58.3 mmol) was added and stirred thoroughly, followed by addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.3 mmol). 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 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 12.1 g of compound subCB-2 (yield 65%, MS: [M+H] + = 478).

[0569]

[0570] Compound subCB-2 (15 g, 38.9 mmol) and compound Trz15 (15.3 g, 38.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 17.9 g of compound 1-32 (yield 65%, MS: [M+H] + = 709).

[0571] Preparation Example 1-33

[0572]

[0573] Compound CB (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 11.3 g of compound subCB-3 (yield 66%, MS: [M+H] + = 336).

[0574]

[0575] Under a nitrogen atmosphere, compound subCB-3 (15 g, 44.7 mmol) and compound Trz3 (18 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 20.9 g of compound 1-33 (yield 71%, MS: [M+H] + = 659).

[0576] Preparation Example 1-34

[0577]

[0578] Compound CC (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 13.2 g of compound subCC-1 (yield 77%, MS: [M+H] + = 336).

[0579]

[0580] Compound subCC-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diborane under nitrogen atmosphere. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred thoroughly, followed by addition of bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting 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 14.1 g of compound subCC-2 (yield 74%, MS: [M+H] + = 428).

[0581]

[0582] Under a nitrogen atmosphere, compound subCC-2 (15 g, 35.1 mmol) and compound Trz22 (13.8 g, 35.1 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 16.9 g of compound 1-34 (yield 73%, MS: [M+H] + = 659).

[0583] Preparation Example 1-35

[0584]

[0585] Compound CD (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred, and 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.3 g of compound subCD-1 (yield 60%, MS: [M+H] + = 336).

[0586]

[0587] Compound subCD-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. oxane, and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. After reacting 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, and 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 subCD-2 (yield 71%, MS: [M+H] + = 428).

[0588]

[0589] Compound subCD-2 (15 g, 35.1 mmol) and compound Trz23 (13.8 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.4 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18 g of compound 1-35 (yield 78%, MS: [M+H]+=659).

[0590] Preparation Example 1-36

[0591]

[0592] Compound subCD-1 (15 g, 38.9 mmol) and compound Trz7 (15.3 g, 38.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.4 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 1-36 (yield 62%, MS: [M+H]+=709).

[0593] Preparation Example 1-37

[0594]

[0595] Compound CD (15 g, 51 mmol) and dibenzo[b,d]furan-2-ylboronic acid (10.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.2 g of compound subCD-3 (yield 66%, MS: [M+H]+=424).

[0596]

[0597] Compound subCD-3 (15 g, 35.2 mmol) and bis(pinacolato)diboron (9.8 g, 38.7 mmol) were added to 300 ml of 1,4-diborane under nitrogen atmosphere. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.2 g, 52.8 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol) were added. After reacting 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, and 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 subCD-4 (yield 65%, MS: [M+H] + = 518).

[0598]

[0599] Compound subCD-4 (15 g, 29 mmol) and compound Trz5 (7.8 g, 29 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12 g, 87 mmol) was then dissolved in 36 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.3 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 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, and 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 1-37 (yield 71%, MS: [M+H] + = 623).

[0600] Preparation Example 1-38

[0601]

[0602] Compound CE (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and 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 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 subCE-1 (yield 74%, MS: [M+H] + = 412).

[0603]

[0604] Compound subCE-1 (15 g, 36.4 mmol) and bis(pinacolato)diboron (10.2 g, 40.1 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.4 g, 54.6 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol). After reacting for 6 hours, cooling to room temperature was performed. 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 12.8 g of compound subCE-2 (yield 70%, MS: [M+H] + = 504).

[0605]

[0606] Compound subCE-2 (15 g, 29.8 mmol) and compound Trz23 (11 g, 29.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 89.4 mmol) was then dissolved in 37 ml of water and added thereto. Thereafter, it was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.3 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 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 16 g of compound 1-38 (yield 76%, MS: [M+H]+=709).

[0607] Preparation Example 1-39

[0608]

[0609] Compound CE (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 subCE-3 (yield 76%, MS: [M+H] + = 336).

[0610]

[0611] Compound subCE-3 (15 g, 44.7 mmol) and compound Trz24 (18 g, 44.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.5 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 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 22.9 g of compound 1-39 (yield 78%, MS: [M+H]+=659).

[0612] Preparation Example 1-40

[0613]

[0614] Compound CF (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 13.3 g of compound subCF-1 (yield 78%, MS: [M+H] + = 336).

[0615]

[0616] Compound subCF-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting for 10 hours, cooling to room temperature was carried out. 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 13.5 g of compound subCF-2 (yield 71%, MS: [M+H] + = 428).

[0617]

[0618] Compound subCF-2 (15 g, 35.1 mmol) and compound Trz25 (14.7 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 18 g of compound 1-40 (yield 75%, MS: [M+H] + = 685).

[0619] Preparation Example 1-41

[0620]

[0621] Compound CF (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 subCF-3 (yield 77%, MS: [M+H] + = 386).

[0622]

[0623] Compound subCF-3 (15 g, 38.9 mmol) and compound Trz26 (17.6 g, 38.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred and bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 20.9 g of compound 1-41 (yield 71%, MS: [M+H] + = 759).

[0624] Preparation Example 1-42

[0625]

[0626] Compound DA (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.6 g of compound subDA-1 (yield 64%, MS: [M+H] + = 386).

[0627]

[0628] Compound subDA-1 (15 g, 38.9 mmol) and bis(pinacolato)diboron (10.9 g, 42.8 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.7 g, 58.3 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.3 mmol) were added. After reacting 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 11.9 g of compound subDA-2 (yield 64%, MS: [M+H] + = 478).

[0629]

[0630] Compound subDA-2 (15 g, 31.4 mmol) and compound Trz6 (11.2 g, 31.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (13 g, 94.3 mmol) was then dissolved in 39 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 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 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 14.8 g of compound 1-42 (yield 70%, MS: [M+H] + = 673).

[0631] Preparation Example 1-43

[0632]

[0633] Compound DA (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subDA-3 (yield 65%, MS: [M+H] + = 412).

[0634]

[0635] Compound subDA-3 (15 g, 36.4 mmol) and bis(pinacolato)diboron (10.2 g, 40.1 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.4 g, 54.6 mmol) was added and stirred thoroughly, and then bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol) were added. After reacting for 5 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 12.5 g of compound subDA-4 (yield 68%, MS: [M+H] + = 504).

[0636]

[0637] Compound subDA-4 (15 g, 29.8 mmol) and compound Trz15 (9.5 g, 29.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 89.4 mmol) was then dissolved in 37 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.3 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 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 1-43 (yield 73%, MS: [M+H] + = 659).

[0638] Preparation Example 1-44

[0639]

[0640] Compound DB (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 11.1 g of compound subDB-1 (yield 65%, MS: [M+H] + = 336).

[0641]

[0642] Compound subDB-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium (0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting for 5 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 14.1 g of compound subDB-2 (yield 74%, MS: [M+H] + = 428).

[0643]

[0644] Compound subDB-2 (15 g, 35.1 mmol) and compound Trz6 (12.6 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred and 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. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 15.9 g of compound 1-44 (yield 73%, MS: [M+H] + = 623).

[0645] Preparation Example 1-45

[0646]

[0647] Compound subDB-2 (15 g, 35.1 mmol) and compound Trz27 (12.1 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 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 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 15.2 g of compound 1-45 (yield 71%, MS: [M+H] + = 609).

[0648] Preparation Example 1-46

[0649]

[0650] Compound DC (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 12.1 g of compound subDC-1 (yield 71%, MS: [M+H] + = 336).

[0651]

[0652] Compound subDC-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Potassium acetate (6.6 g, 67 mmol) was then added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium (0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting for 6 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 13.5 g of compound subDC-2 (yield 71%, MS: [M+H] + = 428).

[0653]

[0654] Compound subDC-2 (15 g, 35.1 mmol) and compound Trz28 (13.1 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred and 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. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 1-46 (yield 64%, MS: [M+H] + = 639).

[0655] Preparation Example 1-47

[0656]

[0657] Compound DD (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 13.5 g of compound subDD-1 (yield 79%, MS: [M+H] + = 336).

[0658]

[0659] Compound subDD-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Potassium acetate (6.6 g, 67 mmol) was then added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium (0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting for 6 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 13.5 g of compound subDD-2 (yield 71%, MS: [M+H] + = 428).

[0660]

[0661] Compound subDD-2 (15 g, 35.1 mmol) and compound Trz22 (13.8 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred and 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. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 15.2 g of compound 1-47 (yield 66%, MS: [M+H] + = 659).

[0662] Preparation Example 1-48

[0663]

[0664] Compound DD (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subDD-3 (yield 61%, MS: [M+H] + = 412).

[0665]

[0666] Compound subDD-3 (15 g, 36.4 mmol) and bis(pinacolato)diboron (10.2 g, 40.1 mmol) were added to 300 ml of 1,4-diboron. The mixture was stirred and refluxed in oxane. Then, potassium acetate (5.4 g, 54.6 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol). After reacting for 8 hours, the mixture was cooled to room temperature. The organic layer was then separated using chloroform and water and distilled. It was then 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 subDD-4 (yield 78%, MS: [M+H] + = 504).

[0667]

[0668] Compound subDD-4 (15 g, 29.8 mmol) and compound Trz18 (10.7 g, 29.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 89.4 mmol) was then dissolved in 37 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 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 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 13.5 g of compound 1-48 (yield 65%, MS: [M+H] + = 699).

[0669] Preparation Example 1-49

[0670]

[0671] Compound DD (15 g, 51 mmol) and dibenzo[b,d]furan-2-ylboronic acid (10.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. After this, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was then distilled. It was then 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 15.6 g of compound subDD-5 (yield 72%, MS: [M+H] + = 426).

[0672]

[0673] Compound subDD-5 (15 g, 35.2 mmol) and bis(pinacolato)diboron (9.8 g, 38.7 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (5.2 g, 52.8 mmol) was added and stirred thoroughly, followed by the addition of bis(dibenzylideneacetone)palladium(0) (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol). After reacting for 5 hours, cooling to room temperature was performed. 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 12.4 g of compound subDD-6 (yield 68%, MS: [M+H] + = 518).

[0674]

[0675] Compound subDD-6 (15 g, 29 mmol) and compound Trz5 (7.8 g, 29 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12 g, 87 mmol) was then dissolved in 36 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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 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 1-49 (yield 72%, MS: [M+H] + = 623).

[0676] Preparation Example 1-50

[0677]

[0678] Compound DE (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. After this, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then dissolved in chloroform again and washed twice with water. After this, 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 subDE-1 (yield 61%, MS: [M+H] + = 336).

[0679]

[0680] Compound subDE-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture is stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) is added and stirred thoroughly, followed by addition of bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting for 10 hours, cooling to room temperature is carried out. Then, the organic layer is separated using chloroform and water and distilled. Then, it is dissolved in chloroform again and washed twice with water. Thereafter, the organic layer is separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 13.7 g of compound subDE-2 (yield 72%, MS: [M+H] + = 428).

[0681]

[0682] Compound subDE-2 (15 g, 35.1 mmol) and compound Trz29 (13.1 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 1-50 (yield 69%, MS: [M+H] + = 639).

[0683] Preparation Example 1-51

[0684]

[0685] Compound DE (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, the mixture was stirred thoroughly and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. The mixture was then dissolved in chloroform again and washed twice with water. 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 subDE-3 (yield 65%, MS: [M+H] + = 386).

[0686]

[0687] Compound subDE-3 (15 g, 38.9 mmol) and bis(pinacolato)diboron (10.9 g, 42.8 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture is stirred and refluxed. Then, potassium acetate (5.7 g, 58.3 mmol) is added and stirred thoroughly, followed by addition of bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.3 mmol). After reacting for 9 hours, cooling to room temperature is carried out. Then, the organic layer is separated using chloroform and water and distilled. Then, it is dissolved in chloroform again and washed twice with water. Thereafter, the organic layer is separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is purified by silica gel column chromatography to prepare 11.5 g of compound subDE-4 (yield 62%, MS: [M+H] + = 478).

[0688]

[0689] Under a nitrogen atmosphere, compound subDE-4 (15 g, 31.4 mmol) and compound Trz27 (10.8 g, 31.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (13 g, 94.3 mmol) was then dissolved in 39 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 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 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 13.2 g of compound 1-51 (yield 64%, MS: [M+H] + = 659).

[0690] Preparation Example 1-52

[0691]

[0692] Compound DF (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. After this, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then dissolved in chloroform again and washed twice with water. After this, 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 13.3 g of compound subDF-1 (yield 78%, MS: [M+H] + = 336).

[0693]

[0694] Compound subDF-1 (15 g, 44.7 mmol) and compound Trz30 (21.4 g, 44.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 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 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 g of compound 1-52 (yield 70%, MS: [M+H] + = 735).

[0695] Preparation Example 1-53

[0696]

[0697] Compound subDF-1 (15 g, 44.7 mmol) and bis(pinacolato)diboron (12.5 g, 49.1 mmol) were added to 300 ml of 1,4-diboron. alkane, and the mixture was stirred and refluxed. Then, potassium acetate (6.6 g, 67 mmol) was added and stirred thoroughly, followed by addition of bis(dibenzylideneacetone)palladium(0) (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol). After reacting for 8 hours, cooling to room temperature was performed. 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 11.6 g of compound subDF-2 (yield 61%, MS: [M+H] + = 428).

[0698]

[0699] Compound subDF-2 (15 g, 35.1 mmol) and compound Trz31 (12.9 g, 35.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.6 g, 105.3 mmol) was then dissolved in 44 ml of water and added thereto. Thereafter, it was fully stirred 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 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 16.9 g of compound 1-53 (yield 76%, MS: [M+H] + = 633).

[0700] Preparation Example 2-1

[0701]

[0702] Under a nitrogen atmosphere, compound subAA-3 (10 g, 31.3 mmol), compound amine 1 (13.2 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 3 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 12.8 g of compound 2-1 (yield 58%, MS: [M+H] + = 705).

[0703] Preparation Example 2-2

[0704]

[0705] Under a nitrogen atmosphere, compound subAA-3 (10 g, 31.3 mmol), compound amine 2 (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 3 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 10.6 g of compound 2-2 (yield 54%, MS: [M+H] + = 629).

[0706] Preparation Example 2-3

[0707]

[0708] Under a nitrogen atmosphere, compound subAA-3 (10 g, 31.3 mmol), compound amine 3 (11 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 12.9 g of compound 2-3 (yield 65%, MS: [M+H] + = 635).

[0709] Preparation Example 2-4

[0710]

[0711] Compound subAA-3 (15 g, 46.9 mmol) and compound amine 4 (20.7 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 24 g of compound 2-4 (yield 74%, MS: [M+H] + = 691).

[0712] Preparation Example 2-5

[0713]

[0714] 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 under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Thereafter, it was fully stirred, and 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 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 15.7 g of compound subAA-4 (yield 79%, MS: [M+H] + = 370).

[0715]

[0716] Compound subAA-4 (15 g, 40.6 mmol) and compound amine 5 (16.8 g, 40.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 18.3 g of compound 2-5 (yield 64%, MS: [M+H] + = 705).

[0717] Preparation Example 2-6

[0718]

[0719] Compound subAB-1 (10 g, 31.3 mmol), compound amine 6 (12.9 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-6 (yield 69%, MS: [M+H] + = 695).

[0720] Preparation Example 2-7

[0721]

[0722] Compound subAB-1 (10 g, 31.3 mmol), compound amine 7 (10.9 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-7 (yield 66%, MS: [M+H] + = 633).

[0723] Preparation Example 2-8

[0724]

[0725] Under a nitrogen atmosphere, compound subAB-1 (15 g, 46.9 mmol) and compound amine 8 (24.9 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 fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.5 g of compound 2-8 (yield 76%, MS: [M+H] + = 771).

[0726] Preparation Example 2-9

[0727]

[0728] Compound subAB-1 (15 g, 46.9 mmol) and compound amine 9 (26.6 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.1 g of compound 2-9 (yield 69%, MS: [M+H] + = 807).

[0729] Preparation Example 2-10

[0730]

[0731] Compound AB (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 under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Thereafter, it was fully stirred, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAB-3 (yield 70%, MS: [M+H] + = 396).

[0732]

[0733] Compound subAB-3 (10 g, 25.3 mmol), compound amine 10 (6.2 g, 25.3 mmol) and sodium tert-butoxide (8 g, 37.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 9.9 g of compound 2-10 (yield 65%, MS: [M+H] + = 605).

[0734] Preparation Example 2-11

[0735]

[0736] Compound AC (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, the mixture was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added thereto. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was distilled. The mixture was then dissolved in chloroform again and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAC-3 (yield 70%, MS: [M+H]+=320).

[0737]

[0738] Compound subAC-3 (10 g, 31.3 mmol), compound amine 11 (14 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 13.9 g of compound 2-11 (yield 61%, MS: [M+H] + = 731).

[0739] Preparation Example 2-12

[0740]

[0741] Compound subAC-3 (10 g, 31.3 mmol), compound amine 12 (11.6 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 10.4 g of compound 2-12 (yield 51%, MS: [M+H] + = 655).

[0742] Preparation Example 2-13

[0743]

[0744] Compound subAC-3 (10 g, 31.3 mmol), compound amine 13 (11.3 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 13.7 g of compound 2-13 (yield 68%, MS: [M+H] + = 645).

[0745] Preparation Example 2-14

[0746]

[0747] Under a nitrogen atmosphere, compound subAC-3 (15 g, 46.9 mmol) and compound amine 14 (19.5 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 fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.5 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 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 23.6 g of compound 2-14 (yield 77%, MS: [M+H] + = 655).

[0748] Preparation Example 2-15

[0749]

[0750] Compound subAC-3 (15 g, 46.9 mmol) and compound amine 15 (20.7 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting 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 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 g of compound 2-15 (yield 72%, MS: [M+H] + = 681).

[0751] Preparation Example 2-16

[0752]

[0753] Compound AC (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. After this, it was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added thereto. After reacting for 11 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was distilled. It was then redissolved in chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAC-4 (yield 64%, MS: [M+H]+=370).

[0754]

[0755] Compound subAC-4 (10 g, 27 mmol), compound amine 16 (8.7 g, 27 mmol) and sodium tert-butoxide (8.6 g, 40.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 9.4 g of compound 2-16 (yield 53%, MS: [M+H] + = 655).

[0756] Preparation Example 2-17

[0757]

[0758] Under a nitrogen atmosphere, compound subAD-1 (10 g, 31.3 mmol), compound amine 17 (13.2 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 3 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 2-17 (yield 59%, MS: [M+H] + = 705).

[0759] Preparation Example 2-18

[0760]

[0761] Under a nitrogen atmosphere, compound subAD-1 (15 g, 40.6 mmol) and compound amine 18 (23 g, 40.6 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 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 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 20.9 g of compound 2-18 (yield 64%, MS: [M+H] + = 807).

[0762] Preparation Example 2-19

[0763]

[0764] Compound subAD-1 (10 g, 31.3 mmol), compound amine 19 (12.8 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 11.5 g of compound 2-19 (yield 53%, MS: [M+H] + = 694).

[0765] Preparation Example 2-20

[0766]

[0767] Under a nitrogen atmosphere, compound subAD-1 (15 g, 40.6 mmol) and compound amine 20 (18.5 g, 40.6 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 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 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 19.4 g of compound 2-20 (yield 69%, MS: [M+H] + = 695).

[0768] Preparation Example 2-21

[0769]

[0770] Compound AD (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, the mixture was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was distilled. The mixture was then dissolved in chloroform again and washed twice with water. 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 subAD-5 (yield 68%, MS: [M+H] + = 370).

[0771]

[0772] Under a nitrogen atmosphere, compound subAD-5 (10 g, 27 mmol), compound amine 21 (8 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 9.2 g of compound 2-21 (yield 54%, MS: [M+H] + = 630).

[0773] Preparation Example 2-22

[0774]

[0775] Compound subAE-1 (10 g, 31.3 mmol), compound amine 22 (13.2 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-22 (yield 60%, MS: [M+H] + = 705).

[0776] Preparation Example 2-23

[0777]

[0778] Compound subAE-1 (15 g, 46.9 mmol) and compound amine 23 (25.4 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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, and 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 2-23 (yield 64%, MS: [M+H] + = 781).

[0779] Preparation Example 2-24

[0780]

[0781] Compound subAE-1 (15 g, 46.9 mmol) and compound amine 24 (23.1 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.5 mmol) was added. After reacting 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 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 22.3 g of compound 2-24 (yield 65%, MS: [M+H] + = 731).

[0782] Preparation Example 2-25

[0783]

[0784] Compound AE (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-boronic acid (10.7 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Thereafter, it was fully stirred, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subAE-4 (yield 62%, MS: [M+H] + = 396).

[0785]

[0786] Compound subAE-4 (10 g, 25.3 mmol), compound amine 16 (8.1 g, 25.3 mmol) and sodium tert-butoxide (8 g, 37.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 g of compound 2-25 (yield 64%, MS: [M+H] + = 681).

[0787] Preparation Example 2-26

[0788]

[0789] Compound subAF-1 (15 g, 46.9 mmol) and compound amine 25 (20.7 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 2-26 (yield 65%, MS: [M+H] + = 757).

[0790] Preparation Example 2-27

[0791]

[0792] Compound subBA-3 (15 g, 40.6 mmol) and compound amine 26 (19.9 g, 40.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 18.1 g of compound 2-27 (yield 61%, MS: [M+H] + = 731).

[0793] Preparation Example 2-28

[0794]

[0795] Compound subBA-3 (15 g, 40.6 mmol) and compound amine 27 (19.1 g, 40.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After reacting 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 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 21.6 g of compound 2-28 (yield 75%, MS: [M+H] + = 711).

[0796] Preparation Example 2-29

[0797]

[0798] Compound subBA-3 (15 g, 40.6 mmol) and compound amine 28 (17.9 g, 40.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 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 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 19.6 g of compound 2-29 (yield 71%, MS: [M+H] + = 681).

[0799] Preparation Example 2-30

[0800]

[0801] Compound subBB-1 (10 g, 31.3 mmol), compound amine 29 (11.6 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-30 (yield 53%, MS: [M+H] + = 655).

[0802] Preparation Example 2-31

[0803]

[0804] Compound subBB-1 (10 g, 31.3 mmol), compound amine 30 (12.4 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-31 (yield 63%, MS: [M+H]+=681).

[0805] Preparation Example 2-32

[0806]

[0807] Compound subBB-1 (15 g, 46.9 mmol) and compound amine 31 (23.1 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25 g of compound 2-32 (yield 73%, MS: [M+H] + = 731).

[0808] Preparation Example 2-33

[0809]

[0810] Compound subBB-1 (15 g, 46.9 mmol) and compound amine 32 (24.3 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.5 mmol) was added. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.6 g of compound 2-33 (yield 61%, MS: [M+H] + = 757).

[0811] Preparation Example 2-34

[0812]

[0813] Compound BC (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Afterwards, the mixture was stirred thoroughly, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was distilled. The mixture was then dissolved in chloroform again and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subBC-3 (yield 72%, MS: [M+H] + = 320).

[0814]

[0815] Compound subBC-3 (10 g, 31.3 mmol), compound amine 33 (12.9 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-34 (yield 61%, MS: [M+H] + = 695).

[0816] Preparation Example 2-35

[0817]

[0818] Compound subBC-3 (10 g, 31.3 mmol), compound amine 34 (14 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-35 (yield 56%, MS: [M+H] + = 731).

[0819] Preparation Example 2-36

[0820]

[0821] Compound subBC-3 (15 g, 46.9 mmol) and compound amine 35 (19.5 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.4 g of compound 2-36 (yield 60%, MS: [M+H] + = 655).

[0822] Preparation Example 2-37

[0823]

[0824] Compound subBC-3 (15 g, 46.9 mmol) and compound amine 36 (18.5 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 2-37 (yield 70%, MS: [M+H] + = 635).

[0825] Preparation Example 2-38

[0826]

[0827] Compound BC (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-boronic acid (10.7 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting 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 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 15.8 g of compound subBC-4 (yield 74%, MS: [M+H] + = 396).

[0828]

[0829] Compound subBC-4 (10 g, 25.3 mmol), compound amine 37 (10 g, 25.3 mmol) and sodium tert-butoxide (8 g, 37.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-38 (yield 62%, MS: [M+H] + = 757).

[0830] Preparation Example 2-39

[0831]

[0832] Compound subBD-1 (10 g, 31.3 mmol), compound amine 38 (10.8 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-39 (yield 60%, MS: [M+H] + = 629).

[0833] Preparation Example 2-40

[0834]

[0835] Compound subBD-1 (10 g, 31.3 mmol), compound amine 39 (11.6 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-40 (yield 67%, MS: [M+H] + = 655).

[0836] Preparation Example 2-41

[0837]

[0838] Compound subBD-1 (10 g, 31.3 mmol), compound amine 40 (11.6 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.5 g of compound 2-41 (yield 56%, MS: [M+H] + = 655).

[0839] Preparation Example 2-42

[0840]

[0841] Compound subBD-1 (10 g, 31.3 mmol), compound amine 41 (14 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.8 g of compound 2-42 (yield 65%, MS: [M+H] + = 731).

[0842] Preparation Example 2-43

[0843]

[0844] Compound BD (15 g, 53.9 mmol) and naphthalene-2-ylboronic acid (9.3 g, 53.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.4 g, 161.8 mmol) was then dissolved in 67 ml of water and added thereto. Thereafter, it was fully stirred, and 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 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 13.7 g of compound subBD-3 (yield 69%, MS: [M+H] + = 370).

[0845]

[0846] Compound subBD-3 (15 g, 40.6 mmol) and compound amine 42 (18.5 g, 40.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.7 g of compound 2-43 (yield 72%, MS: [M+H] + = 745).

[0847] Preparation Example 2-44

[0848]

[0849] Compound subBE-1 (15 g, 46.9 mmol) and compound amine 43 (22 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.6 g of compound 2-44 (yield 80%, MS: [M+H] + = 709).

[0850] Preparation Example 2-45

[0851]

[0852] Compound subBE-1 (15 g, 46.9 mmol) and compound amine 44 (22.6 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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, and 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 2-45 (yield 69%, MS: [M+H] + = 721).

[0853] Preparation Example 2-46

[0854]

[0855] Compound subBE-1 (15 g, 46.9 mmol) and compound amine 45 (24.3 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.5 mmol) was added. After reacting 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.3 g of compound 2-46 (yield 74%, MS: [M+H] + = 757).

[0856] Preparation Example 2-47

[0857]

[0858] Compound subBE-2 (10 g, 27 mmol), compound amine 37 (10.7 g, 27 mmol) and sodium tert-butoxide (8.6 g, 40.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-47 (yield 60%, MS: [M+H]+=731).

[0859] Preparation Example 2-48

[0860]

[0861] Compound subBF-1 (15 g, 46.9 mmol) and compound amine 46 (23.1 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 2-48 (yield 62%, MS: [M+H] + = 731).

[0862] Preparation Example 2-49

[0863]

[0864] Compound subBF-1 (10 g, 31.3 mmol), compound amine 47 (9.2 g, 31.3 mmol) and sodium tert-butoxide (10 g, 46.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 10.7 g of compound 2-49 (yield 59%, MS: [M+H] + = 579).

[0865] Preparation Example 2-50

[0866]

[0867] Compound subBF-1 (15 g, 46.9 mmol) and compound amine 48 (26.6 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (19.5 g, 140.7 mmol) was then dissolved in 58 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 28.4 g of compound 2-50 (yield 75%, MS: [M+H] + = 807).

[0868] Preparation Example 2-51

[0869]

[0870] Under a nitrogen atmosphere, compound subBF-2 (10 g, 27 mmol), compound amine 49 (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 3 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 10.7 g of compound 2-51 (yield 59%, MS: [M+H] + = 669).

[0871] Preparation Example 2-52

[0872]

[0873] Under a nitrogen atmosphere, compound subBF-2 (15 g, 40.6 mmol) and compound amine 50 (21 g, 40.6 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.7 mmol) was then dissolved in 50 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 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 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 20 g of compound 2-52 (yield 61%, MS: [M+H] + = 807).

[0874] Preparation Example 2-53

[0875]

[0876] Under a nitrogen atmosphere, compound subCA-1 (10 g, 29.8 mmol), compound amine 51 (13.3 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-53 (yield 63%, MS: [M+H] + = 747).

[0877] Preparation Example 2-54

[0878]

[0879] Under a nitrogen atmosphere, compound subCA-1 (10 g, 29.8 mmol), compound amine 52 (11.5 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 2 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 10.6 g of compound 2-54 (yield 52%, MS: [M+H] + = 685).

[0880] Preparation Example 2-55

[0881]

[0882] Compound subCA-1 (15 g, 46.9 mmol) and compound amine 53 (24.5 g, 46.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.5 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 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 27.9 g of compound 2-55 (yield 78%, MS: [M+H] + = 803).

[0883] Preparation Example 2-56

[0884]

[0885] Compound subCA-2 (15 g, 48.3 mmol) and compound amine 35 (16.1 g, 48.3 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.4 g, 0.4 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 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 19.9 g of compound 2-56 (yield 71%, MS: [M+H] + = 721).

[0886] Preparation Example 2-57

[0887]

[0888] Under a nitrogen atmosphere, compound subCB-3 (10 g, 29.8 mmol), compound amine 54 (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 2 hours, the reaction was complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 12.9 g of compound 2-57 (yield 60%, MS: [M+H] + = 721).

[0889] Preparation Example 2-58

[0890]

[0891] Under a nitrogen atmosphere, compound subCB-3 (10 g, 29.8 mmol), compound amine 55 (11.8 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of dimethylbenzene, 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 complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 g of compound 2-58 (yield 53%, MS: [M+H] + = 697).

[0892] Preparation Example 2-59

[0893]

[0894] Under a nitrogen atmosphere, compound subCB-3 (15 g, 44.7 mmol) and compound amine 56 (21.5 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Afterwards, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then dissolved in chloroform again and washed twice with water. Afterwards, 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 22.4 g of compound 2-59 (yield 68%, MS: [M+H] + = 737).

[0895] Preparation Example 2-60

[0896]

[0897] Under a nitrogen atmosphere, compound subCB-3 (15 g, 44.7 mmol) and compound amine 57 (21.9 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. After this, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After 12 hours of reaction, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then dissolved in chloroform again and washed twice with water. After this, 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 g of compound 2-60 (yield 69%, MS: [M+H] + = 747).

[0898] Preparation Example 2-61

[0899]

[0900] Under a nitrogen atmosphere, compound subCB-3 (15 g, 44.7 mmol) and compound amine 58 (21.5 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After reacting 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 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 24.3 g of compound 2-61 (yield 74%, MS: [M+H] + = 737).

[0901] Preparation Example 2-62

[0902]

[0903] Under a nitrogen atmosphere, compound subCB-3 (15 g, 44.7 mmol) and compound amine 59 (21.9 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. After this, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After 12 hours of reaction, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then dissolved in chloroform again and washed twice with water. After this, 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 g of compound 2-62 (yield 78%, MS: [M+H] + = 747).

[0904] Preparation Example 2-63

[0905]

[0906] Compound CB (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was then distilled. It was then 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 14.9 g of compound subCB-4 (yield 71%, MS: [M+H] + = 412).

[0907]

[0908] Under a nitrogen atmosphere, compound subCB-4 (10 g, 24.3 mmol), compound amine 10 (6 g, 24.3 mmol) and sodium tert-butoxide (7.7 g, 36.4 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, 0.2 mmol) was added thereto. After 2 hours, the reaction was complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 8.9 g of compound 2-63 (yield 59%, MS: [M+H] + = 621).

[0909] Preparation Example 2-64

[0910]

[0911] Under a nitrogen atmosphere, compound subCC-1 (10 g, 29.8 mmol), compound amine 60 (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 complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 2-64 (yield 66%, MS: [M+H] + = 671).

[0912] Preparation Example 2-65

[0913]

[0914] Under a nitrogen atmosphere, compound subCC-1 (10 g, 29.8 mmol), compound amine 61 (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 2 hours, the reaction was complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 10.7 g of compound 2-65 (yield 50%, MS: [M+H] + = 721).

[0915] Preparation Example 2-66

[0916]

[0917] Under a nitrogen atmosphere, compound subCC-1 (15 g, 44.7 mmol) and compound amine 62 (21.9 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After reacting 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 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 22.7 g of compound 2-66 (yield 68%, MS: [M+H] + = 747).

[0918] Preparation Example 2-67

[0919]

[0920] Under a nitrogen atmosphere, compound subCC-1 (15 g, 44.7 mmol) and compound amine 63 (23.7 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 0.4 mmol) was added. After reacting 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 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 26.3 g of compound 2-67 (yield 75%, MS: [M+H] + = 786).

[0921] Preparation Example 2-68

[0922]

[0923] Compound CC (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, the mixture was stirred thoroughly and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. The mixture was then dissolved in chloroform again and washed twice with water. 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 11.8 g of compound subCC-3 (yield 60%, MS: [M+H] + = 386).

[0924]

[0925] Under a nitrogen atmosphere, compound subCC-3 (10 g, 25.9 mmol), compound amine 16 (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 complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 11.5 g of compound 2-68 (yield 66%, MS: [M+H] + = 671).

[0926] Preparation Example 2-69

[0927]

[0928] Compound subCD-1 (10 g, 29.8 mmol), compound amine 64 (11.1 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-69 (yield 60%, MS: [M+H]+=671).

[0929] Preparation Example 2-70

[0930]

[0931] Compound subCD-1 (10 g, 29.8 mmol), compound amine 65 (11.8 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-70 (yield 54%, MS: [M+H] + = 697).

[0932] Preparation Example 2-71

[0933]

[0934] Compound subCD-1 (15 g, 44.7 mmol) and compound amine 66 (25.1 g, 44.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.5 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 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, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.4 g of compound 2-71 (yield 78%, MS: [M+H] + = 817).

[0935] Preparation Example 2-72

[0936]

[0937] Compound CD (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 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 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, and 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 subCD-5 (yield 70%, MS: [M+H] + = 386).

[0938]

[0939] Compound subCD-5 (10 g, 27.3 mmol), compound amine 21 (8.1 g, 27.3 mmol) and sodium tert-butoxide (8.7 g, 41 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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, and 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 2-72 (yield 61%, MS: [M+H] + = 645).

[0940] Preparation Example 2-73

[0941]

[0942] Compound subCE-3 (10 g, 29.8 mmol), compound amine 67 (13.3 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 15.3 g of compound 2-73 (yield 69%, MS: [M+H] + = 747).

[0943] Preparation Example 2-74

[0944]

[0945] Compound subCE-3 (10 g, 29.8 mmol), compound amine 17 (12.6 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 13.1 g of compound 2-74 (yield 61%, MS: [M+H] + = 721).

[0946] Preparation Example 2-75

[0947]

[0948] Compound subCE-3 (15 g, 44.8 mmol) and compound amine 68 (24.2 g, 44.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.6 g, 134.3 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was thoroughly stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 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 27.1 g of compound 2-75 (yield 76%, MS: [M+H] + = 797).

[0949] Preparation Example 2-76

[0950]

[0951] Compound subCE-3 (15 g, 44.8 mmol) and compound amine 69 (22 g, 44.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.6 g, 134.3 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was thoroughly stirred 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 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 21.4 g of compound 2-76 (yield 64%, MS: [M+H] + = 747).

[0952] Preparation Example 2-77

[0953]

[0954] Compound subCE-1 (15 g, 36.4 mmol) and compound amine 70 (13.3 g, 36.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.2 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was thoroughly stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 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 16 g of compound 2-77 (yield 63%, MS: [M+H] + = 697).

[0955] Preparation Example 2-78

[0956]

[0957] Under a nitrogen atmosphere, compound subCF-1 (10 g, 29.8 mmol), compound amine 71 (10.4 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-78 (yield 61%, MS: [M+H] + = 649).

[0958] Preparation Example 2-79

[0959]

[0960] Under a nitrogen atmosphere, compound subCF-1 (10 g, 29.8 mmol), compound amine 72 (13.3 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 2-79 (yield 56%, MS: [M+H] + = 747).

[0961] Preparation Example 2-80

[0962]

[0963] Compound subCF-1 (15 g, 44.8 mmol) and compound amine 73 (23.2 g, 44.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.6 g, 134.3 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting 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 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 25.9 g of compound 2-80 (yield 75%, MS: [M+H] + = 773).

[0964] Preparation Example 2-81

[0965]

[0966] Compound CF (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and 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 in chloroform again and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, and 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 subCF-4 (yield 74%, MS: [M+H] + = 412).

[0967]

[0968] Under a nitrogen atmosphere, compound subCF-4 (15 g, 36.4 mmol) and compound amine 25 (16.1 g, 36.4 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.2 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting 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 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 20.8 g of compound 2-81 (yield 74%, MS: [M+H] + = 773).

[0969] Preparation Example 2-82

[0970]

[0971] Compound DA (15 g, 51 mmol) and phenylboronic acid (6.2 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 13.5 g of compound subDA-5 (yield 79%, MS: [M+H] + = 336).

[0972]

[0973] Compound subDA-5 (10 g, 29.8 mmol), compound amine 74 (12.6 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 11.4 g of compound 2-82 (yield 53%, MS: [M+H] + = 721).

[0974] Preparation Example 2-83

[0975]

[0976] Compound subDA-5 (10 g, 29.8 mmol), compound amine 75 (12.6 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 12.2 g of compound 2-83 (yield 57%, MS: [M+H] + = 721).

[0977] Preparation Example 2-84

[0978]

[0979] Compound subDA-5 (15 g, 44.7 mmol) and compound amine 63 (23.7 g, 44.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting 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 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 22.1 g of compound 2-84 (yield 63%, MS: [M+H] + = 786).

[0980] Preparation Example 2-85

[0981]

[0982] Under a nitrogen atmosphere, compound subDB-1 (10 g, 29.8 mmol), compound amine 40 (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 2 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 13.8 g of compound 2-85 (yield 69%, MS: [M+H] + = 671).

[0983] Preparation Example 2-86

[0984]

[0985] Under a nitrogen atmosphere, compound subDB-1 (10 g, 29.8 mmol), compound amine 76 (10.4 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 11.4 g of compound 2-86 (yield 59%, MS: [M+H] + = 649).

[0986] Preparation Example 2-87

[0987]

[0988] Compound DB (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting 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 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 16.6 g of compound subDB-3 (yield 79%, MS: [M+H] + = 412).

[0989]

[0990] Compound subDB-3 (15 g, 36.4 mmol) and amine 77 (16.6 g, 36.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.1 g, 109.2 mmol) was then dissolved in 45 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 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 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 19.3 g of compound 2-87 (yield 69%, MS: [M+H] + = 767).

[0991] Preparation Example 2-88

[0992]

[0993] Under a nitrogen atmosphere, compound subDC-1 (10 g, 29.8 mmol), compound amine 78 (10 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 complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 2-88 (yield 63%, MS: [M+H] + = 635).

[0994] Preparation Example 2-89

[0995]

[0996] Under a nitrogen atmosphere, compound subDC-1 (15 g, 44.7 mmol) and compound amine 79 (23.1 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 23.8 g of compound 2-89 (yield 69%, MS: [M+H] + = 773).

[0997] Preparation Example 2-90

[0998]

[0999] Compound DC (15 g, 51 mmol) and [1,1'-biphenyl]-4-boronic acid (10.1 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. After this, it was fully stirred, and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer, and the organic layer was then distilled. It was then 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 subDC-3 (yield 62%, MS: [M+H] + = 412).

[1000]

[1001] Under a nitrogen atmosphere, compound subDC-3 (10 g, 24.3 mmol), compound amine 37 (9.6 g, 24.3 mmol) and sodium tert-butoxide (7.7 g, 36.4 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, 0.2 mmol) was added thereto. After 2 hours, the reaction was complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 10.5 g of compound 2-90 (yield 56%, MS: [M+H] + = 773).

[1002] Preparation Example 2-91

[1003]

[1004] Under a nitrogen atmosphere, compound subDD-1 (10 g, 29.8 mmol), compound amine 65 (11.8 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 14.3 g of compound 2-91 (yield 69%, MS: [M+H] + = 697).

[1005] Preparation Example 2-92

[1006]

[1007] Under a nitrogen atmosphere, compound subDD-1 (10 g, 29.8 mmol), compound amine 80 (13.3 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 11.3 g of compound 2-92 (yield 51%, MS: [M+H] + = 747).

[1008] Preparation Example 2-93

[1009]

[1010] Under a nitrogen atmosphere, compound subDD-1 (15 g, 44.8 mmol) and compound amine 81 (20.8 g, 44.8 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.6 g, 134.3 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred 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 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 24.2 g of compound 2-93 (yield 75%, MS: [M+H] + = 721).

[1011] Preparation Example 2-94

[1012]

[1013] Compound subDD-1 (15 g, 44.7 mmol) and compound amine 82 (19.7 g, 44.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred 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 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 22.7 g of compound 2-94 (yield 73%, MS: [M+H] + = 697).

[1014] Preparation Example 2-95

[1015]

[1016] Compound DD (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Thereafter, it was fully stirred and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 subDD-7 (yield 71%, MS: [M+H] + = 386).

[1017]

[1018] Under a nitrogen atmosphere, compound subDD-7 (15 g, 38.9 mmol) and compound amine 77 (17.7 g, 38.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred 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 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 21.3 g of compound 2-95 (yield 72%, MS: [M+H] + = 761).

[1019] Preparation Example 2-96

[1020]

[1021] Under a nitrogen atmosphere, compound subDE-1 (10 g, 29.8 mmol), compound amine 84 (13.3 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 complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 13.6 g of compound 2-96 (yield 61%, MS: [M+H] + = 747).

[1022] Preparation Example 2-97

[1023]

[1024] Under a nitrogen atmosphere, compound subDE-1 (10 g, 29.8 mmol), compound amine 6 (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 2 hours, the reaction was complete, and the solvent was removed under reduced pressure after cooling to room temperature. 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 14.2 g of compound 2-97 (yield 67%, MS: [M+H] + = 712).

[1025] Preparation Example 2-98

[1026]

[1027] Under a nitrogen atmosphere, compound subDE-1 (15 g, 44.7 mmol) and compound amine 85 (23.1 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 8 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 22.1 g of compound 2-98 (yield 64%, MS: [M+H] + = 773).

[1028] Preparation Example 2-99

[1029]

[1030] Under a nitrogen atmosphere, compound subDE-1 (15 g, 44.7 mmol) and compound amine 86 (25.3 g, 44.7 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (18.5 g, 134 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 9 hours, it was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. It was then 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 23.9 g of compound 2-99 (yield 65%, MS: [M+H] + = 823).

[1031] Preparation Example 2-100

[1032]

[1033] Compound subDF-1 (10 g, 24.3 mmol), compound amine 87 (9 g, 24.3 mmol) and sodium tert-butoxide (7.7 g, 36.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 2 hours, the reaction was completed, and the solvent was removed under reduced pressure after cooling to room temperature. 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 8.8 g of compound 2-100 (yield 54%, MS: [M+H] + = 671).

[1034] Preparation Example 2-101

[1035]

[1036] Compound subDF-1 (10 g, 29.8 mmol), compound amine 19 (12.2 g, 29.8 mmol) and sodium tert-butoxide (9.5 g, 44.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, 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 the solvent was removed under reduced pressure after cooling to room temperature. 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 12.5 g of compound 2-101 (yield 59%, MS: [M+H] + = 710).

[1037] Preparation Example 2-102

[1038]

[1039] Compound subDF-1 (15 g, 44.8 mmol) and compound amine 56 (21.6 g, 44.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.6 g, 134.3 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting 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 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 23.7 g of compound 2-102 (yield 72%, MS: [M+H] + = 737).

[1040] Preparation Example 2-103

[1041]

[1042] Compound subDF-1 (15 g, 44.8 mmol) and compound amine 83 (21.1 g, 44.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.6 g, 134.3 mmol) was then dissolved in 56 ml of water and added thereto. Thereafter, it was fully stirred 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 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 2-103 (yield 72%, MS: [M+H] + = 727).

[1043] Preparation Example 2-104

[1044]

[1045] Compound DF (15 g, 51 mmol) and naphthalene-2-ylboronic acid (8.8 g, 51 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.1 g, 153 mmol) was then dissolved in 63 ml of water and added thereto. Afterwards, the mixture was stirred thoroughly and tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and the organic layer was distilled. The mixture was then dissolved in chloroform again and washed twice with water. 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 subDF-3 (yield 76%, MS: [M+H] + = 386).

[1046]

[1047] Under a nitrogen atmosphere, compound subDF-3 (15 g, 38.9 mmol) and compound amine 50 (20.1 g, 38.9 mmol) were added to 300 ml of THF, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.6 mmol) was then dissolved in 48 ml of water and added thereto. Thereafter, it was fully stirred and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting 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 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 19.8 g of compound 2-104 (yield 62%, MS: [M+H] + = 823).

[1048] [Example]

[1049] Comparative Example A

[1050] It is coated with a thickness of The ITO (indium tin oxide) of the present invention is put into the distilled water that is wherein dissolved with detergent as the glass substrate of film, and carry out ultrasonic cleaning.At this moment, use the product manufactured by Fischer Co. as detergent, and use the distilled water filtered twice with the filter manufactured by Millipore Co. as distilled water.After ITO was cleaned 30 minutes, distilled water was used to repeat ultrasonic cleaning twice 10 minutes.After completing with distilled water cleaning, substrate isopropyl alcohol, acetone and methanol solvent are carried out ultrasonic cleaning, dry, then transfer to plasma cleaner.In addition, use oxygen plasma that substrate is cleaned 5 minutes, then transfer to vacuum deposition device.

[1051] A hole injection layer was formed on the prepared ITO transparent electrode using the following compound HI-1. The thickness of the hole injection layer was 1.5 wt% and the following compound A-1 was doped. Then, the compound HT-1 was vacuum deposited on the hole injection layer to Thereafter, the following compounds EB-1 to EB-2 were vacuum deposited on the hole transport layer. Then, the following compounds RH-1 and Dp-7 were vacuum deposited on the EB-1 deposited film at a weight ratio of 98:2 to The red light emitting layer was formed by vacuum depositing the following compound HB-1 onto the light emitting layer. 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 form a hole blocking layer. The thickness of the electron injection and transport layer is formed. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron injection and transport layer to a thickness of and to form a cathode.

[1052]

[1053] In the above process, the deposition rate of organic material is kept at to The deposition rate of lithium fluoride at the cathode was kept at and maintaining the aluminum deposition rate at In addition, the vacuum level during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 support, thereby manufacturing an organic light-emitting device.

[1054] Examples 1 to 29

[1055] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compounds shown in Table 1 were used instead of Compound RH-1 as a host in the organic light-emitting device of Comparative Example A.

[1056] Comparative Examples 1 to 7

[1057] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compounds shown in Table 1 were used instead of Compound RH-1 as a 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.

[1058]

[1059] Examples 30 to 75

[1060] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compound shown in Table 2 was used instead of Compound EB-1 as an electron blocking layer material in the organic light-emitting device of Comparative Example A.

[1061] Comparative Examples 8 to 14

[1062] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the compounds shown in Table 2 were used instead of compound EB-1 as 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.

[1063]

[1064] Examples 76 to 179

[1065] An organic light-emitting device was manufactured in the same manner as in Comparative Example A, except that the first host and second host compounds described in Table 3 were used in a weight ratio of 1:1 instead of the host compound RH-1 in the organic light-emitting device of Comparative Example A.

[1066] [Experimental example]

[1067] The driving voltage and efficiency (based on 15 mA / cm 2 ), and the results are shown in the following Tables 1 to 3. The lifespan T95 means the time taken until the initial luminance (7000 nits) decreases to 95%.

[1068] [Table 1]

[1069]

[1070]

[1071] [Table 2]

[1072]

[1073]

[1074] [Table 3]

[1075]

[1076]

[1077]

[1078]

[1079]

[1080]

[1081] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 179 and Comparative Examples 1 to 14, the results shown in Tables 1 to 3 were obtained.

[1082] As shown in Tables 1 and 2, it was determined that when the compounds of the present disclosure were used in the light-emitting layer or electron blocking layer of an organic light-emitting device, the driving voltage was reduced and the efficiency and lifespan were increased compared to the case where the compounds of the comparative examples were used. In addition, as shown in Table 3, when the compounds of the present disclosure were co-deposited and used as a co-host, the driving voltage was reduced and the efficiency and lifespan were increased compared to the case where a single material host was used.

[1083] In summary, it was determined that when the compound of the present disclosure is used as a host of a red light-emitting layer or as an electron blocking layer in a red device, the driving voltage, luminous efficiency, and lifespan characteristics of an organic light-emitting device can be improved.

[1084] Reference numerals

[1085] 1: substrate 2: anode

[1086] 3: Light-emitting layer 4: Cathode

[1087] 5: Hole injection layer 6: Hole transport layer

[1088] 7: Electron blocking layer 8: Hole blocking layer

[1089] 9: Electron injection and transport layer.

Claims

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

2. The compound according to claim 1, Wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In Chemical Formulas 1-1 to 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, naphthalenediyl, or dibenzofurandiyl.

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

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

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

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

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, The compound represented by Chemical Formula 1 is any one selected from the following compounds:

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

12. The organic light-emitting device according to claim 11, The organic material layer is a light-emitting layer or an electron blocking layer.

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