Organic light-emitting device

Abstract

The present invention provides an organic light emitting device with improved driving voltage, efficiency and lifetime.

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2021-0024903 dated February 24, 2021, and all contents disclosed in the documents of that Korean patent application are incorporated herein by reference.

[0002] The present invention relates to an organic light emitting device with improved driving voltage, efficiency and lifetime. [Background technology]

[0003] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, and therefore many researches are being conducted on these devices.

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

[0005] In such organic light-emitting devices, there is a continuing demand for the development of organic light-emitting devices with improved driving voltage, efficiency, and life span. [Prior art documents] [Patent documents]

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

[0007] The present invention provides an organic light-emitting device with improved driving voltage, efficiency and lifetime. [Means for solving the problem]

[0008] The present invention provides an organic light-emitting device comprising: A positive electrode and A negative electrode; a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer is an organic light-emitting device including (i) a compound represented by the following Chemical Formula 1, and (ii) a compound represented by the following Chemical Formula 2 or 3: [Chemical formula 1] [ka] In the above Chemical Formula 1, L is a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; X is N; or CH, with the proviso that at least two of X are N; R is hydrogen, deuterium, a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, [Chemical formula 2] [ka] [Chemical formula 3] [ka] In the above Chemical Formulas 2 and 3, R' is a substituent represented by the following chemical formula 4, or a substituted or unsubstituted aryl having 6 to 60 carbon atoms, When R' is a substituent represented by the following chemical formula 4, R' 1 ~R' 6 are each independently hydrogen or deuterium; When R' is not a substituent represented by the following formula 4, R' 1 ~R' 6 one of which is a substituent represented by the following chemical formula 4, and the rest are each independently hydrogen or deuterium; [Chemical formula 4] [ka] In the above Chemical Formula 4, L' is a single bond, a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; L' 1 and L' 2 each independently represents a single bond, a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms containing at least one selected from the group consisting of substituted or unsubstituted N, O, and S; Ar' 1 and Ar' 2 are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S. Effect of the Invention

[0009] The above-mentioned organic light-emitting device is excellent in terms of driving voltage, efficiency and life span. [Brief description of the drawings]

[0010] [Figure 1]FIG. 1 is a diagram showing an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Diagram 2] FIG. 1 is a diagram showing an example of an organic light-emitting element consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8 and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The present invention will now be described in more detail to aid in its understanding.

[0012] In this specification, [ka] or [ka] denotes a bond that is connected to another substituent.

[0013] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthiooxy group; arylthiooxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heterocyclic group containing one or more of N, O and S atoms, or that the group is substituted or unsubstituted with two or more of the above-mentioned exemplified substituents connected to each other. For example, the "substituent having two or more substituents connected to each other" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent having two phenyl groups connected to each other.

[0014] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferably 1 to 40. Specifically, the carbonyl group may have a structure as shown below, but is not limited thereto. [ka]

[0015] In this specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto. [ka]

[0016] In this specification, the number of carbon atoms of the imido group is not particularly limited, but is preferably 1 to 25. Specifically, the imido group may have a structure as shown below, but is not limited thereto. [ka]

[0017] In this specification, specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group, but are not limited to these.

[0018] In this specification, specific examples of the boron group include a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group, but are not limited to these.

[0019] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0020] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0021] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited thereto.

[0022] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples 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, and cyclooctyl, but are not limited thereto.

[0023] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0024] In this specification, the fluorenyl group may be substituted, and two of the substituents may be bonded together to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to these.

[0025] In this specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a hetero element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of heterocyclic groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0026] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aralkyl group, the aralkenyl group, the alkylaryl group, and the aryl group in the arylamine group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the aralkyl group, the alkylaryl group, and the alkylamine group. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heteroaryl in the heteroarylamine. In this specification, the above-mentioned explanation regarding the alkenyl group is applicable to the alkenyl group in the aralkenyl group. In this specification, the above-mentioned explanation regarding the aryl group is applicable to the arylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heteroarylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the aryl group or the cycloalkyl group is applicable to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heterocyclic group, except that it is not a monovalent group but is formed by bonding two substituents.

[0027] The present invention will be described in detail below for each component.

[0028] Positive and negative electrodes The positive electrode and the negative electrode used in the present invention refer to electrodes used in an organic light-emitting device.

[0029] The positive electrode material is preferably a material having a large work function so that holes can be easily injected into the organic layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SNO 2Examples of the conductive polymers include, but are not limited to: a combination of a metal such as Sb with an oxide; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0030] The negative electrode material is preferably a material with a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2 / Al and other multi-layered materials, but are not limited to these.

[0031] Emitting layer The light-emitting layer used in the present invention means a layer capable of emitting light in the visible light region by combining holes and electrons transferred from the positive and negative electrodes. In general, the light-emitting layer includes a host material and a dopant material, and in the present invention, includes (i) a compound represented by the following Chemical Formula 1, and (ii) a compound represented by the following Chemical Formula 2 or 3 together with the host.

[0032] In the above Chemical Formula 1, L is preferably a single bond, phenylene, or naphthylene. More preferably, L is a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, or 1,4-naphthylene.

[0033] Preferably, all X's are N.

[0034] Preferably, R is hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, triphenylenyl, fluoranthenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, or benzonaphthothiophenyl.

[0035] Preferably, Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.

[0036] Representative examples of the compound represented by Chemical Formula 1 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0037] The present invention also provides a method for preparing the compound represented by Chemical Formula 1, as shown in the following Reaction Scheme 1: [Reaction Scheme 1] [ka] In the above reaction scheme 1, the remainder except for X is as defined above, and X is a halogen, preferably bromine or chlorine. The above reaction scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the reaction can be changed according to those known in the art. The above preparation method is further embodied in the preparation examples described below.

[0038] In the above chemical formulas 2 and 3, R' is preferably a substituent represented by the above chemical formula 4, or a substituted or unsubstituted aryl having 6 to 12 carbon atoms. More preferably, R' is a substituent represented by the above chemical formula 4, or a phenyl, biphenyl, or naphthyl.

[0039] Preferably, L' is a single bond, or a substituted or unsubstituted arylene having 6 to 12 carbon atoms. More preferably, L' is a single bond, phenylene, biphenyldiyl, terphenyldiyl, naphthylene, or -(phenylene)-(naphthylene)-. More preferably, L' is a single bond, 1,4-phenylene, 4,4'-biphenyldiyl, or 2,6-naphthylene.

[0040] Preferably, L' 1 and L' 2 are each independently a single bond or a substituted or unsubstituted arylene having 6 to 12 carbon atoms. 1 and L' 2 are each independently a single bond, phenylene, or biphenyldiyl. More preferably, L' 1 and L' 2 each independently is a single bond, 1,4-phenylene, or 4,4'-biphenyldiyl.

[0041] Preferably, Ar' 1 and Ar' 2are each independently phenyl, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

[0042] Preferably, R' 1 ~R' 4 one of R' is a substituent represented by Chemical Formula 4, and the rest are each independently hydrogen or deuterium; 5 and R' 6 are each independently hydrogen or deuterium.

[0043] Preferably, R' 1 ~R' 4 are each independently hydrogen or deuterium; R' 5 and R' 6 One of Ar' is a substituent represented by Chemical Formula 4, and the rest are hydrogen or deuterium. 1 and Ar' 2 are each independently terphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazolyl. 1 is phenyl, and Ar' 2 is phenyl, biphenyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazolyl; or Ar' is 1 is biphenylyl, and Ar' 2 is terphenylyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazolyl, where preferably L' 1 and L' 2are each independently a single bond, phenylene, or biphenyldiyl, and more preferably, L' 1 and L' 2 each independently is a single bond, 1,4-phenylene, or 4,4'-biphenyldiyl.

[0044] Representative examples of the compounds represented by the above formula 2 or 3 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0045] In addition, the present invention relates to a compound represented by the above chemical formula 2, wherein R' 1 The present invention provides a method for preparing the compound represented by formula 4, and the remaining compounds represented by formula 2 and formula 3 can also be prepared in a similar manner. [Reaction Scheme 2] [ka] In the reaction scheme 2, the remainder except for X' and Y' are as defined above, X is a halogen, preferably bromine or chlorine, Y' is hydrogen when L' is a single bond, and -B(OH) when L is not a single bond. 2 The reaction scheme 2 is an amine substitution reaction or a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for each reaction can be changed according to those known in the art. The preparation method is further embodied in the preparation examples described below.

[0046] Meanwhile, the dopant material is not particularly limited as long as it is a material used in an organic light-emitting device. Examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the dopant material includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0047] Hole transport layer The organic light-emitting device according to the present invention may include a hole transport layer between the light-emitting layer and the positive electrode.

[0048] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. As the hole transport material, a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer and has high mobility for holes is preferable.

[0049] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0050] Hole injection layer The organic light-emitting device according to the present invention may optionally include a hole-injection layer between the positive electrode and the hole-transport layer.

[0051] The hole injection layer is a layer that injects holes from the positive electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect from the positive electrode, has an excellent hole injection effect on the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. In particular, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.

[0052] Specific examples of hole injection materials include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0053] electron transport layer The organic light-emitting device according to the present invention may include an electron transport layer between the light-emitting layer and the negative electrode.

[0054] The electron transport layer receives electrons from the negative electrode or the electron injection layer formed on the negative electrode, transports the electrons to the light-emitting layer, and suppresses the transfer of holes from the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the negative electrode and transfer them to the light-emitting layer and has high mobility for electrons is preferable.

[0055] Specific examples of the electron transport material include Al complexes of 8-hydroxyquinoline; Alq 3The electron transport layer may be used with any desired cathode material, such as those used by the prior art. In particular, examples of suitable cathode materials are conventional materials having low work functions, followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, followed in each case by an aluminum or silver layer.

[0056] electron injection layer The organic light-emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the negative electrode, if necessary.

[0057] The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from a negative electrode, has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin-film forming ability.

[0058] Specific examples of the substance used in the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0059] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0060] Organic light-emitting device The structure of an organic light-emitting device according to the present invention is shown in Figures 1 and 2. Figure 1 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Figure 2 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a negative electrode 4.

[0061] The organic light emitting device according to the present invention may be manufactured by sequentially stacking the above-mentioned components. In this case, a metal or conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a positive electrode, and the above-mentioned layers may be formed thereon, followed by deposition of a material to be used as a negative electrode. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a negative electrode material on a substrate in the reverse order of the above-mentioned components to a positive electrode material (WO 2003 / 012890). In addition, the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like.

[0062] Meanwhile, the organic light emitting device according to the present invention may be a front emission type, a rear emission type, or a dual emission type, depending on the materials used.

[0063] The preparation of the organic light emitting device will now be described in detail with reference to examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto.

[0064] [Production Example] Compound 1-1 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz1 (19.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in water (50 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.9 g of compound sub1-A-1. (Yield 71%, MS: [M+H] + =484)

[0065] Compound sub1-A-1 (15 g, 31 mmol) and compound sub1 (6.1 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in water (26 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.3 g of compound 1-1. (Yield 66%, MS: [M+H] + =602)

[0066] Compound 1-2 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound sub1-A-2. (Yield 74%, MS: [M+H] + =434)

[0067] Compound sub1-A-2 (15 g, 34.6 mmol) and compound sub2 (9.4 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in water (29 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.3 g of compound 1-2. (Yield 66%, MS: [M+H] + =626)

[0068] Compound 1-3 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.2 g of compound sub1-A-3. (Yield 79%, MS: [M+H] + =484)

[0069] Compound sub1-A-3 (15 g, 31 mmol) and compound sub3 (7.1 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in water (26 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound 1-3. (Yield 66%, MS: [M+H] + =632)

[0070] Compound 1-4 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz4 (27 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound sub1-A-4 26 g. (Yield 70%, MS: [M+H] + =610)

[0071] Compound sub1-A-4 (15 g, 24.6 mmol) and compound sub4 (5.6 g, 24.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (6.8 g, 49.2 mmol) was dissolved in water (20 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.2 g of compound 1-4. (Yield 60%, MS: [M+H] + =758)

[0072] Compound 1-5 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz5 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of compound sub1-B-1. (Yield 77%, MS: [M+H] + =560)

[0073] Compound sub1-B-1 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in water (22 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound 1-5. (Yield 80%, MS: [M+H]+=602)

[0074] Compound 1-6 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.2 g of compound sub1-B-2. (Yield 62%, MS: [M+H] + =484)

[0075] Compound sub1-B-2 (15 g, 31 mmol) and compound sub6 (7.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in water (26 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.3 g of compound 1-6. (Yield 76%, MS: [M+H] + =650)

[0076] Compound 1-7 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.8 g of compound sub1-B-3. (Yield 79%, MS: [M+H] + =434)

[0077] Compound sub1-B-3 (15 g, 34.6 mmol) and compound sub7 (8.6 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in water (29 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.4 g of compound 1-7. (Yield 74%, MS: [M+H] + =602)

[0078] Compound 1-8 [ka] Compound sub1-B-2 (15 g, 31 mmol) and compound sub8 (8.1 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in water (26 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.5 g of compound 1-8. (Yield 75%, MS: [M+H] + =666)

[0079] Compound 1-9 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz6 (22.4 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.7 g of compound sub1-B-4. (Yield 73%, MS: [M+H] + =534)

[0080] Compound sub1-B-4 (15 g, 28.1 mmol) and compound sub9 (6 g, 28.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in water (23 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6 g of compound 1-9. (Yield 62%, MS: [M+H] + =666)

[0081] Compound 1-10 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz7 (28.6 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.6 g of compound sub1-B-5. (Yield 74%, MS: [M+H] + =636)

[0082] Compound sub1-B-5 (15 g, 23.6 mmol) and compound sub5 (2.9 g, 23.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (6.5 g, 47.2 mmol) was dissolved in water (20 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.4 g of compound 1-5. (Yield 65%, MS: [M+H] + =678)

[0083] Compound 1-11 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz8 (21.8 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.1 g of compound sub1-B-6. (Yield 63%, MS: [M+H] + =524)

[0084] Compound sub1-B-6 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.9 g, 57.3 mmol) was dissolved in water (24 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 1-11. (Yield 65%, MS: [M+H] + =616)

[0085] Compound 1-12 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.6 g of compound sub1-C-1. (Yield 60%, MS: [M+H] + =484)

[0086] Compound sub1-C-1 (15 g, 31 mmol) and compound sub10 (5.3 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in water (26 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound 1-12. (Yield 72%, MS: [M+H] + =576)

[0087] Compound 1-13 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz9 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.5 g of compound sub1-C-2. (Yield 69%, MS: [M+H] + =560)

[0088] Compound sub1-C-2 (15 g, 26.8 mmol) and compound sub10 (4.6 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in water (22 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of compound 1-13. (Yield 80%, MS: [M+H] + =652)

[0089] Compound 1-14 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.5 g of compound sub1-C-3. (Yield 66%, MS: [M+H] + =510)

[0090] Compound sub1-C-3 (15 g, 29.4 mmol) and compound sub11 (7.3 g, 29.4 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.1 g, 58.8 mmol) was dissolved in water (24 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.3 g of compound 1-14. (Yield 77%, MS: [M+H] + =678)

[0091] Compound 1-15 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.7 g of compound sub1-C-4. (Yield 71%, MS: [M+H] + =434)

[0092] Compound sub1-C-4 (15 g, 37.1 mmol) and compound sub12 (9.7 g, 37.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.3 g, 74.3 mmol) was dissolved in water (31 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of compound 1-15. (Yield 64%, MS: [M+H] + =616)

[0093] Compound 1-16 [ka] Compound sub1-C-3 (15 g, 26.8 mmol) and compound sub13 (7.4 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in water (22 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.2 g of compound 1-16. (Yield 80%, MS: [M+H] + =758)

[0094] Compound 1-17 [ka] Compound sub1-C-4 (15 g, 34.6 mmol) and compound sub14 (7.7 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in water (29 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.3 g of compound 1-17. (Yield 62%, MS: [M+H] + =576)

[0095] Compound 1-18 [ka] Compound sub1-C-1 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in water (26 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12 g of compound 1-18. (Yield 63%, MS: [M+H] + =616)

[0096] Compound 1-19 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz11 (22.4 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.4 g of compound sub1-C-5. (Yield 69%, MS: [M+H] + =534)

[0097] Compound sub1-C-5 (15 g, 28.1 mmol) and compound sub15 (6 g, 28.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in water (23 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-19. (Yield 71%, MS: [M+H] + =666)

[0098] Compound 1-20 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz12 (21.8 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound sub1-C-6 21 g. (Yield 66%, MS: [M+H] + =524)

[0099] Compound sub1-C-6 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in water (36 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.3 g of compound 1-20. (Yield 70%, MS: [M+H] + =616)

[0100] Compound 1-21 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of compound sub1-C-7. (Yield 77%, MS: [M+H] + =560)

[0101] Compound sub1-C-7 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in water (33 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.5 g of compound 1-21. (Yield 65%, MS: [M+H] + =602)

[0102] Compound 1-22 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz14 (19.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound sub1-D-1. (Yield 67%, MS: [M+H] + =586)

[0103] Compound sub1-D-1 (15 g, 25.6 mmol) and compound sub5 (3.1 g, 25.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in water (32 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.3 g of compound 1-22. (Yield 64%, MS: [M+H] + =628)

[0104] Compound 1-23 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20 g of compound sub1-D-2. (Yield 76%, MS: [M+H] + =434)

[0105] Compound sub1-D-2 (15 g, 34.6 mmol) and compound sub16 (9.1 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14 g of compound 1-23. (Yield 66%, MS: [M+H] + =616)

[0106] Compound 1-24 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.8 g of compound sub1-D-3. (Yield 67%, MS: [M+H] + =510)

[0107] Compound 1-D-3 (15 g, 29.4 mmol) and compound 17 (7.7 g, 29.4 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in water (37 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 1-24. (Yield 61%, MS: [M+H] + =692)

[0108] Compound 1-25 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz15 (21.8 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.3 g of compound sub1-D-4. (Yield 67%, MS: [M+H] + =524)

[0109] Compound sub1-D-4 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in water (36 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.7 g of compound 1-25. (Yield 61%, MS: [M+H] + =616)

[0110] Compound 1-26 [ka] Compound sub1-D-3 (15 g, 29.4 mmol) and compound sub18 (6.2 g, 29.4 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in water (37 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.3 g of compound 1-26. (Yield 76%, MS: [M+H] + =642)

[0111] Compound 1-27 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz16 (27 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.1 g of compound sub1-D-5. (Yield 73%, MS: [M+H] + =610)

[0112] Compound sub1-D-5 (15 g, 24.6 mmol) and compound sub9 (5.2 g, 24.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in water (31 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound 1-27. (Yield 70%, MS: [M+H] + =742)

[0113] Compound 1-28 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.8 g of compound sub1-D-6. (Yield 61%, MS: [M+H] + =560)

[0114] Compound sub1-D-6 (15 g, 26.8 mmol) and compound sub10 (4.6 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in water (33 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2 g of compound 1-28. (Yield 70%, MS: [M+H] + =652)

[0115] Compound 1-29 [ka]

[0116] Compound 1-E (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.1 g of compound sub1-E-1. (Yield 65%, MS: [M+H] + =434)

[0117] Compound sub1-E-1 (15 g, 34.6 mmol) and compound sub2 (9.4 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.5 g of compound 1-29. (Yield 67%, MS: [M+H] + =626)

[0118] Compound 1-30 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz9 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.9 g of compound sub1-E-2. (Yield 79%, MS: [M+H] + =560)

[0119] Compound sub1-E-2 (15 g, 26.8 mmol) and compound sub19 (7 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in water (33 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.9 g of compound 1-30. (Yield 80%, MS: [M+H] + =742)

[0120] Compound 1-31 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz17 (22.4 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.3 g of compound sub1-E-3. (Yield 78%, MS: [M+H] + =534)

[0121] Compound 1-E-3 (15 g, 28.1 mmol) and compound 20 (7.8 g, 28.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.6 g, 84.3 mmol) was dissolved in water (35 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.8 g of compound 1-31. (Yield 72%, MS: [M+H] + =732)

[0122] Compound 1-32 [ka] Compound sub1-E-1 (15 g, 34.6 mmol) and compound sub21 (7.7 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound 1-32. (Yield 65%, MS: [M+H] + =576)

[0123] Compound 1-33 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz15 (21.8 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.5 g of compound sub1-E-4. (Yield 80%, MS: [M+H] + =524)

[0124] Compound sub1-E-4 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in water (36 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.6 g of compound 1-33. (Yield 60%, MS: [M+H] + =616)

[0125] Compound 1-34 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.6 g of compound sub1-E-5. (Yield 60%, MS: [M+H] + =484)

[0126] Compound sub1-E-5 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 1-34. (Yield 60%, MS: [M+H] + =616)

[0127] Compound 1-35 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound sub1-E-6. (Yield 70%, MS: [M+H] + =510)

[0128] Compound sub1-E-6 (15 g, 29.4 mmol) and compound sub22 (7.7 g, 29.4 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in water (37 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of compound 1-35. (Yield 72%, MS: [M+H] + =692)

[0129] Compound 1-36 [ka] Compound sub1-E-5 (15 g, 31 mmol) and compound sub23 (8.1 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 1-36. (Yield 60%, MS: [M+H] + =666)

[0130] Compound 1-37 [ka] Compound sub1-E-5 (15 g, 31 mmol) and compound sub10 (5.3 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.1 g of compound 1-37. (Yield 79%, MS: [M+H] + =576)

[0131] Compound 1-38 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz18 (27 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.1 g of compound sub1-E-7. (Yield 65%, MS: [M+H] + =610)

[0132] Compound sub1-E-7 (15 g, 24.6 mmol) and compound sub5 (3 g, 24.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in water (31 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.1 g of compound 1-38. (Yield 63%, MS: [M+H] + =652)

[0133] Compound 1-39 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of compound sub1-E-8. (Yield 77%, MS: [M+H]+=560)

[0134] Compound sub1-E-8 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in water (33 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 1-39. (Yield 68%, MS: [M+H] + =602)

[0135] Compound 1-40 [ka] Compound 1-F (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound sub1-F-1. (Yield 73%, MS: [M+H] + =434)

[0136] Compound 1-F (15 g, 34.6 mmol) and compound sub6 (8.5 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.7 g of compound 1-40. (Yield 71%, MS: [M+H] + =600)

[0137] Compound 1-41 [ka] Compound 1-F (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.1 g of compound sub1-F-2. (Yield 68%, MS: [M+H] + =510)

[0138] Compound sub1-F-2 (15 g, 29.4 mmol) and compound sub1 (5.8 g, 29.4 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in water (37 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-41. (Yield 77%, MS: [M+H] + =628)

[0139] Compound 1-42 [ka] Compound Trz7 (15 g, 31.9 mmol) and compound sub9 (6.8 g, 31.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in water (40 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.2 g of compound 1-42. (Yield 79%, MS: [M+H] + =602)

[0140] Compound 1-43 [ka] Compound Trz16 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to THF (300ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in water (42ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15g of compound 1-43. (Yield 77%, MS: [M+H] + =576)

[0141] Compound 1-44 [ka] Compound Trz4 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-44. (Yield 73%, MS: [M+H] + =576)

[0142] Compound 1-45 [ka] Compound Trz1 (15 g, 35.7 mmol) and compound sub9 (7.6 g, 35.7 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in water (44 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2 g of compound 1-45. (Yield 62%, MS: [M+H] + =552)

[0143] Compound 1-46 [ka] Compound Trz19 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.6 g of compound 1-46. (Yield 70%, MS: [M+H] + =576)

[0144] Compound 1-47 [ka] Compound Trz20 (15 g, 35.9 mmol) and compound sub9 (7.6 g, 35.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in water (45 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15 g of compound 1-47. (Yield 76%, MS: [M+H] + =550)

[0145] Compound 1-48 [ka] Compound Trz3 (15 g, 47.2 mmol) and compound sub24 (9.7 g, 47.2 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in water (59 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound sub1-G-1 13 g. (Yield 62%, MS: [M+H] + =444)

[0146] Compound sub1-G-1 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.2 g of compound 1-48. (Yield 78%, MS: [M+H] + =576)

[0147] Compound 1-49 [ka] In a nitrogen atmosphere, Trz15 (15 g, 41.9 mmol) and compound sub25 (8.7 g, 41.9 mmol) were added to THF (300 ml) and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.6 g of compound sub1-G-2. (Yield 62%, MS: [M+H] + =484)

[0148] Compound sub1-G-2 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.7 g of compound 1-49. (Yield 72%, MS: [M+H] + =616)

[0149] Compound 1-50 [ka] Compound Trz21 (15 g, 36.8 mmol) and compound sub26 (5.8 g, 36.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in water (46 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound sub1-G-3. (Yield 72%, MS: [M+H] + =484)

[0150] Compound sub1-G-3 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.2 g of compound 1-50. (Yield 69%, MS: [M+H] + =616)

[0151] Compound 1-51 [ka] Compound Trz16 (15 g, 33.8 mmol) and compound sub27 (5.3 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound sub1-G-4. (Yield 76%, MS: [M+H] + =520)

[0152] Compound sub1-G-4 (15 g, 28.8 mmol) and compound sub9 (6.1 g, 28.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in water (36 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-51. (Yield 71%, MS: [M+H] + =652)

[0153] Compound 1-52 [ka] Compound Trz22 (15 g, 36.8 mmol) and compound sub28 (5.8 g, 36.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in water (46 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound sub1-G-5. (Yield 72%, MS: [M+H] + =484)

[0154] Compound sub1-G-5 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13 g of compound 1-52. (Yield 68%, MS: [M+H] + =616)

[0155] Compound 1-53 [ka] Compound Trz23 (15 g, 34.6 mmol) and compound sub27 (5.4 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.3 g of compound sub1-G-6. (Yield 64%, MS: [M+H] + =510)

[0156] Compound sub1-G-6 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 10 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13 g of compound 1-53. (Yield 68%, MS: [M+H] + =616)

[0157] Compound 1-54 [ka] Compound sub1-G-1 (15 g, 33.8 mmol) and compound 1-E (8.3 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.4 g of compound sub1-E-9. (Yield 70%, MS: [M+H] + =610)

[0158] Compound sub1-E-9 (15 g, 24.6 mmol) and compound sub5 (3 g, 24.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in water (31 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2 g of compound 1-54. (Yield 76%, MS: [M+H] + =652)

[0159] Compound 1-55 [ka] In a nitrogen atmosphere, Trz2 (15 g, 56 mmol) and compound sub24 (11.6 g, 56 mmol) were added to THF (300 ml) and stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in water (70 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.6 g of compound sub1-G-7. (Yield 71%, MS: [M+H] + =394)

[0160] Compound sub1-G-7 (15 g, 38.1 mmol) and compound 1-B (9.4 g, 38.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in water (47 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound sub1-B-7. (Yield 65%, MS: [M+H] + =560)

[0161] Compound sub1-B-7 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in water (33 ml) and added, and stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound 1-55. (Yield 80%, MS: [M+H] + =602)

[0162] Compound 1-56 [ka] Compound Trz24 (15 g, 38.1 mmol) and compound sub25 (9.4 g, 38.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in water (47 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound sub1-G-8. (Yield 65%, MS: [M+H] + =560)

[0163] Compound sub1-G-8 (15 g, 30 mmol) and compound sub9 (6.4 g, 30 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in water (37 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound 1-56. (Yield 71%, MS: [M+H] + =632)

[0164] Compound 1-57 [ka] Compound Trz25 (15 g, 41.9 mmol) and compound sub24 (8.7 g, 41.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound sub1-G-9. (Yield 61%, MS: [M+H] + =484)

[0165] Compound sub1-G-9 (15 g, 31 mmol) and compound 1-F (7.6 g, 31 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in water (39 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of compound sub1-F-3. (Yield 62%, MS: [M+H] + =650)

[0166] Compound sub1-F-3 (15 g, 23.1 mmol) and compound sub5 (2.8 g, 23.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in water (29 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.8 g of compound 1-57. (Yield 80%, MS: [M+H] + =692)

[0167] Compound 1-58 [ka] Compound Trz26 (15 g, 33.8 mmol) and compound sub26 (5.3 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.5 g of compound sub1-G-10. (Yield 60%, MS: [M+H] + =520)

[0168] In a nitrogen atmosphere, sub1-G-10 (15 g, 28.8 mmol) and compound 1-D (7.1 g, 28.8 mmol) were added to THF (300 ml) and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in water (36 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15 g of compound sub1-D-7. (Yield 76%, MS: [M+H] + =686)

[0169] Compound sub1-D-7 (15 g, 21.9 mmol) and compound sub5 (2.7 g, 21.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.1 g, 65.6 mmol) was dissolved in water (27 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.9 g of compound 1-58. (Yield 62%, MS: [M+H] + =728)

[0170] Compound 1-59 [ka] Compound Trz15 (15 g, 41.9 mmol) and compound sub24 (8.7 g, 41.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound sub1-G-11. (Yield 61%, MS: [M+H] + =484)

[0171] In a nitrogen atmosphere, sub1-G-11 (15 g, 28.8 mmol) and compound 1-F (7.1 g, 28.8 mmol) were added to THF (300 ml) and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in water (36 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce compound sub1-F-4 15 g. (Yield 76%, MS: [M+H] + =686)

[0172] Compound sub1-F-4 (15 g, 23.1 mmol) and compound sub5 (2.8 g, 23.1 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in water (29 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.1 g of compound 1-59. (Yield 76%, MS: [M+H] + =692)

[0173] Compound 1-60 [ka] Compound Trz12 (15 g, 41.9 mmol) and compound sub28 (6.6 g, 41.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.1 g of compound sub1-G-12. (Yield 61%, MS: [M+H] + =434)

[0174] Compound sub1-G-12 (15 g, 34.6 mmol) and compound 1-D (8.5 g, 34.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in water (43 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.6 g of compound sub1-D-8. (Yield 79%, MS: [M+H] + =500)

[0175] Compound sub1-D-8 (15 g, 25 mmol) and compound sub10 (4.3 g, 25 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.4 g, 75 mmol) was dissolved in water (31 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-60. (Yield 77%, MS: [M+H] + =692)

[0176] Compound 1-61 [ka] Compound Trz27 (15 g, 31.9 mmol) and compound sub9 (6.8 g, 31.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in water (40 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10 g of compound 1-61. (Yield 52%, MS: [M+H] + =602)

[0177] Compound 1-62 [ka] Compound Trz28 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2 g of compound 1-62. (Yield 63%, MS: [M+H] + =576)

[0178] Compound 1-63 [ka] Compound Trz29 (15 g, 31.9 mmol) and compound sub9 (6.8 g, 31.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in water (40 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7 g of compound 1-63. (Yield 66%, MS: [M+H] + =602)

[0179] Compound 1-64 [ka] Compound Trz30 (15 g, 31.9 mmol) and compound sub9 (6.8 g, 31.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in water (40 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.2 g of compound 1-64. (Yield 69%, MS: [M+H] + =602)

[0180] Compound 1-65 [ka] Compound Trz31 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in water (42 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of compound 1-65. (Yield 75%, MS: [M+H] + =576)

[0181] Compound 1-66 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz30 (28.6 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.3 g of compound sub1-B-7. (Yield 50%, MS: [M+H] + =636)

[0182] Compound sub1-B-7 (15 g, 23.6 mmol) and compound sub5 (2.9 g, 23.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.8 g, 70.7 mmol) was dissolved in water (29 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.5 g of compound 1-66. (Yield 53%, MS: [M+H] + =678)

[0183] Compound 1-67 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz32 (25.6 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.9 g of compound sub1-C-8. (Yield 70%, MS: [M+H] + =586)

[0184] Compound sub1-C-8 (15 g, 25.6 mmol) and compound sub5 (3.1 g, 25.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in water (32 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.6 g of compound 1-67. (Yield 66%, MS: [M+H] + =628)

[0185] Compound 1-68 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz33 (27 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.7 g of compound sub1-D-7. (Yield 80%, MS: [M+H] + =610)

[0186] Compound 1-D-7 (15 g, 24.6 mmol) and compound 5 (3 g, 24.6 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in water (31 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.2 g of compound 1-68. (Yield 70%, MS: [M+H] + =652)

[0187] Compound 1-69 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz34 (24 g, 60.9 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in water (76 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8 g of compound sub1-E-9. (Yield 64%, MS: [M+H] + =560)

[0188] Compound sub1-E-9 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in water (33 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10 g of compound 1-69. (Yield 62%, MS: [M+H] + =602)

[0189] Compound 2-1 [ka] Compound 2-AA (10 g, 35.8 mmol), compound amine 1 (16 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of compound 2-1. (Yield 68%, MS: [M+H] + =691)

[0190] Compound 2-2 [ka] Compound 2-AB (10 g, 35.8 mmol), compound amine 2 (12.9 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-2. (Yield 61%, MS: [M+H] + =605)

[0191] Compound 2-3 [ka] Compound 2-AC (10 g, 35.8 mmol), compound amine 3 (16 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.3 g of compound 2-3. (Yield 70%, MS: [M+H ]+= 691)

[0192] Compound 2-4 [ka] Compound 2-AD (10 g, 35.8 mmol), compound amine 4 (10.6 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.7 g of compound 2-4. (Yield 66%, MS: [M+H] + =539).

[0193] Compound 2-5 [ka] Compound 2-AE (10 g, 35.8 mmol), compound amine 5 (13.3 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-5. (Yield 61%, MS: [M+H] + =615)

[0194] Compound 2-6 [ka] Compound 2-AE (10 g, 35.8 mmol), compound amine 6 (12 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-6. (Yield 65%, MS: [M+H] + =579)

[0195] Compound 2-7 [ka] Compound 2-AF (10 g, 35.8 mmol), compound amine 7 (12.3 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.5 g of compound 2-7. (Yield 64%, MS: [M+H] + =589)

[0196] Compound 2-8 [ka] Compound 2-AA (15 g, 53.6 mmol) and compound amine 8 (25.6 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 2-8. (Yield 68%, MS: [M+H] + =655)

[0197] Compound 2-9 [ka] Compound 2-AB (15 g, 53.6 mmol) and compound amine 9 (29.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 2-9. (Yield 61%, MS: [M+H] + =730)

[0198] Compound 2-10 [ka] Compound 2-AC (15 g, 53.6 mmol) and compound amine 10 (29.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.2 g of compound 2-10. (Yield 62%, MS: [M+H] + =730)

[0199] Compound 2-11 [ka] Compound 2-AD (15 g, 53.6 mmol) and compound amine 11 (24.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.9 g of compound 2-11. (Yield 61%, MS: [M+H] + =641)

[0200] Compound 2-12 [ka] Compound 2-AD (15 g, 53.6 mmol) and compound amine 12 (30.5 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.8 g of compound 2-12. (Yield 65%, MS: [M+H] + =741)

[0201] Compound 2-13 [ka] Compound 2-AE (15 g, 53.6 mmol) and compound amine 13 (21.4 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.6 g of compound 2-13. (Yield 60%, MS: [M+H] + =579)

[0202] Compound 2-14 [ka] Compound 2-AE (15 g, 53.6 mmol) and compound amine 14 (23.4 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.1 g of compound 2-14. (Yield 67%, MS: [M+H] + =615)

[0203] Compound 2-15 [ka] Compound 2-AE (15 g, 53.6 mmol) and compound amine 15 (29.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.2 g of compound 2-15. (Yield 62%, MS: [M+H] + =730)

[0204] Compound 2-16 [ka] Compound 2-AE (15 g, 53.6 mmol) and compound amine 11 (24.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-16. (Yield 67%, MS: [M+H] + =641)

[0205] Compound 2-17 [ka] Compound 2-AF (15 g, 53.6 mmol) and compound amine 16 (27.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.5 g of compound 2-17. (Yield 63%, MS: [M+H] + =695)

[0206] Compound 2-18 [ka] Compound 2-AA (15 g, 53.6 mmol) and compound amine 17 (36.2 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.5 g of compound 2-18. (Yield 63%, MS: [M+H] + =843)

[0207] Compound 2-19 [ka] Compound 2-AD (15 g, 53.6 mmol) and compound amine 18 (24.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.3 g of compound 2-19. (Yield 68%, MS: [M+H] + =641)

[0208] Compound 2-20 [ka] Compound 2-AF (15 g, 53.6 mmol) and compound amine 19 (34.8 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.6 g of compound 2-20. (Yield 63%, MS: [M+H] + =817)

[0209] Compound 2-21 [ka] Compound 2-AA (15 g, 53.6 mmol) and compound amine 20 (33.3 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.5 g of compound 2-21. (Yield 65%, MS: [M+H] + =791)

[0210] Compound 2-22 [ka] Compound 2-AD (15 g, 53.6 mmol) and compound amine 21 (32 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.9 g of compound 2-22. (Yield 68%, MS: [M+H] + =767)

[0211] Compound 2-23 [ka] Compound 2-AE (15 g, 53.6 mmol) and compound amine 22 (23.4 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.4 g of compound 2-23. (Yield 68%, MS: [M+H] + =615)

[0212] Compound 2-24 [ka] Compound 2-AH (10 g, 28.1 mmol), compound amine 23 (11.2 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 2-24. (Yield 70%, MS: [M+H] + =717)

[0213] Compound 2-25 [ka] Compound 2-AJ (10 g, 28.1 mmol), compound amine 24 (12.6 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 2-25. (Yield 61%, MS: [M+H] + =767)

[0214] Compound 2-26 [ka] Compound 2-AJ (10 g, 28.1 mmol), compound amine 25 (10.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-26. (Yield 61%, MS: [M+H] + =691)

[0215] Compound 2-27 [ka] Compound 2-AK (10 g, 28.1 mmol), compound amine 26 (9.8 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.6 g of compound 2-27. (Yield 62%, MS: [M+H] + =669)

[0216] Compound 2-28 [ka] Compound 2-AK (15 g, 42.2 mmol) and compound amine 27 (16.2 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.2 g of compound 2-28. (Yield 60%, MS: [M+H] + =641)

[0217] Compound 2-29 [ka] Compound 2-AI (15 g, 42.2 mmol) and compound amine 28 (19.5 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound 2-29. (Yield 60%, MS: [M+H] + =717)

[0218] Compound 2-30 [ka] Compound 2-AG (15 g, 42.2 mmol) and compound amine 29 (25.1 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-30. (Yield 64%, MS: [M+H] + =843)

[0219] Compound 2-31 [ka] Compound 2-AJ (15 g, 42.2 mmol) and compound amine 30 (22.9 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.4 g of compound 2-31. (Yield 67%, MS: [M+H] + =793)

[0220] Compound 2-32 [ka] Compound 2-AI (15 g, 42.2 mmol) and compound amine 31 (21.8 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.6 g of compound 2-32. (Yield 70%, MS: [M+H] + =767)

[0221] Compound 2-33 [ka] Compound 2-AL (15 g, 42.2 mmol) and compound amine 32 (22.9 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 2-33. (Yield 70%, MS: [M+H] + =793)

[0222] Compound 2-34 [ka] Compound 2-AK (15 g, 42.2 mmol) and compound amine 33 (25.1 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.3 g of compound 2-34. (Yield 60%, MS: [M+H] + =843)

[0223] Compound 2-35 [ka] Compound 2-AI (15 g, 42.2 mmol) and compound amine 34 (22.4 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-35. (Yield 69%, MS: [M+H] + =781)

[0224] Compound 2-36 [ka] Compound 2-AH (15 g, 42.2 mmol) and compound amine 35 (22.8 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-36. (Yield 69%, MS: [M+H] + =791)

[0225] Compound 2-37 [ka] Compound 2-AQ (10 g, 30.3 mmol), compound amine 36 (11.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound 2-37. (Yield 68%, MS: [M+H] + =659)

[0226] Compound 2-38 [ka] Compound 2-AO (10 g, 30.3 mmol), compound amine 37 (13.6 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 2-38. (Yield 64%, MS: [M+H] + =741)

[0227] Compound 2-39 [ka] Compound 2-AQ (10 g, 30.3 mmol), compound amine 38 (10.2 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12 g of compound 2-39. (Yield 63%, MS: [M+H] + =629)

[0228] Compound 2-40 [ka] Compound 2-AQ (15 g, 45.5 mmol) and compound amine 27 (17.4 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 2-40. (Yield 66%, MS: [M+H] + =615)

[0229] Compound 2-41 [ka] Compound 2-AN (15 g, 45.5 mmol) and compound amine 39 (24.7 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.9 g of compound 2-41. (Yield 60%, MS: [M+H] + =767)

[0230] Compound 2-42 [ka] Compound 2-AR (15 g, 45.5 mmol) and compound amine 40 (21.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.7 g of compound 2-42. (Yield 66%, MS: [M+H] + =691)

[0231] Compound 2-43 [ka] Compound 2-AP (15 g, 45.5 mmol) and compound amine 41 (27.8 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.1 g of compound 2-43. (Yield 69%, MS: [M+H] + =831)

[0232] Compound 2-44 [ka] Compound 2-AQ (15 g, 45.5 mmol) and compound amine 42 (23.5 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.9 g of compound 2-44. (Yield 68%, MS: [M+H] + =741)

[0233] Compound 2-45 [ka] Compound 2-AN (15 g, 45.5 mmol) and compound amine 43 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26 g of compound 2-45. (Yield 70%, MS: [M+H] + =817)

[0234] Compound 2-46 [ka] Compound 2-AQ (15 g, 45.5 mmol) and compound amine 44 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-46. (Yield 60%, MS: [M+H] + =817)

[0235] Compound 2-47 [ka] Compound 2-AQ (15 g, 43.4 mmol) and compound amine 45 (25.8 g, 45.5 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18 g, 130.1 mmol) was dissolved in water (54 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound 2-47. (Yield 54%, MS: [M+H] + =833)

[0236] Compound 2-48 [ka] Compound 2-AP (15 g, 45.5 mmol) and compound amine 46 (23.5 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.2 g of compound 2-48. (Yield 60%, MS: [M+H] + =741)

[0237] Compound 2-49 [ka] Compound 2-AN (15 g, 45.5 mmol) and compound amine 47 (23.5 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.5 g of compound 2-49. (Yield 64%, MS: [M+H] + =741)

[0238] Compound 2-50 [ka] Compound 2-BA (10 g, 30.3 mmol), compound amine 48 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-50. (Yield 61%, MS: [M+H] + =641)

[0239] Compound 2-51 [ka] Compound 2-BA (10 g, 30.3 mmol), compound amine 49 (11.3 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.7 g of compound 2-51. (Yield 63%, MS: [M+H] + =615)

[0240] Compound 2-52 [ka] Compound 2-BB (10 g, 30.3 mmol), compound amine 50 (12.9 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 2-52. (Yield 69%, MS: [M+H] + =668)

[0241] Compound 2-53 [ka] Compound 2-BC (10 g, 30.3 mmol), compound amine 51 (14 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.8 g of compound 2-53. (Yield 60%, MS: [M+H] + =704)

[0242] Compound 2-54 [ka] Compound 2-BD (10 g, 30.3 mmol), compound amine 52 (13.6 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-54. (Yield 60%, MS: [M+H] + =691)

[0243] Compound 2-55 [ka] Compound 2-BE (10 g, 30.3 mmol), compound amine 53 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-55. (Yield 68%, MS: [M+H] + =641)

[0244] Compound 2-56 [ka] Compound 2-BA (15 g, 53.6 mmol) and compound amine 54 (27.1 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.9 g of compound 2-56. (Yield 60%, MS: [M+H] + =681)

[0245] Compound 2-57 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 55 (26.5 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-57. (Yield 64%, MS: [M+H] + =671)

[0246] Compound 2-58 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 56 (24.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-58. (Yield 66%, MS: [M+H] + =641)

[0247] Compound 2-59 [ka] Compound 2-BE (15 g, 53.6 mmol) and compound amine 57 (22.3 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-59. (Yield 70%, MS: [M+H] + =595)

[0248] Compound 2-60 [ka] Compound 2-BF (15 g, 53.6 mmol) and compound amine 58 (32.7 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.5 g of compound 2-60. (Yield 61%, MS: [M+H] + =780)

[0249] Compound 2-61 [ka] Compound 2-BE (15 g, 53.6 mmol) and compound amine 59 (36.2 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 31.6 g of compound 2-61. (Yield 70%, MS: [M+H] + =843)

[0250] Compound 2-62 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 60 (29.9 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of compound 2-62. (Yield 67%, MS: [M+H] + =730)

[0251] Compound 2-63 [ka] Compound 2-BD (15 g, 53.6 mmol) and compound amine 61 (27.7 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.2 g of compound 2-63. (Yield 60%, MS: [M+H] + =691)

[0252] Compound 2-64 [ka] Compound 2-BE (15 g, 53.6 mmol) and compound amine 62 (23.4 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.1 g of compound 2-64. (Yield 64%, MS: [M+H] + =615)

[0253] Compound 2-65 [ka] Compound 2-BD (15 g, 53.6 mmol) and compound amine 63 (22.8 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 2-65. (Yield 67%, MS: [M+H] + =605)

[0254] Compound 2-66 [ka] Compound 2-BF (15 g, 53.6 mmol) and compound amine 64 (31.6 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.9 g of compound 2-66. (Yield 66%, MS: [M+H] + =760)

[0255] Compound 2-67 [ka] Compound 2-BB (15 g, 53.6 mmol) and compound amine 65 (32 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.1 g of compound 2-67. (Yield 66%, MS: [M+H] + =767)

[0256] Compound 2-68 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 66 (32 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.8 g of compound 2-68. (Yield 65%, MS: [M+H] + =569)

[0257] Compound 2-69 [ka] Compound 2-BB (15 g, 53.6 mmol) and compound amine 67 (29.1 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.5 g of compound 2-69. (Yield 69%, MS: [M+H] + =717)

[0258] Compound 2-70 [ka] Compound 2-BF (15 g, 53.6 mmol) and compound amine 68 (30.5 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25 g of compound 2-70. (Yield 63%, MS: [M+H] + =741)

[0259] Compound 2-71 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 69 (26.2 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.1 g of compound 2-71. (Yield 62%, MS: [M+H] + =665)

[0260] Compound 2-72 [ka] Compound 2-BF (15 g, 53.6 mmol) and compound amine 70 (23.4 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 2-72. (Yield 66%, MS: [M+H] + =615)

[0261] Compound 2-73 [ka] Compound 2-BE (15 g, 53.6 mmol) and compound amine 71 (32 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.5 g of compound 2-73. (Yield 62%, MS: [M+H] + =767)

[0262] Compound 2-74 [ka] Compound 2-BD (15 g, 53.6 mmol) and compound amine 72 (36.2 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 30.7 g of compound 2-74. (Yield 68%, MS: [M+H] + =843)

[0263] Compound 2-75 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 73 (39.1 g, 56.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (22.2 g, 160.9 mmol) was dissolved in water (67 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.7 g of compound 2-75. (Yield 62%, MS: [M+H] + =893)

[0264] Compound 2-76 [ka] Compound 2-BG (10 g, 28.1 mmol), compound amine 74 (10.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-76. (Yield 65%, MS: [M+H] + =691)

[0265] Compound 2-77 [ka] Compound 2-BI (10 g, 28.1 mmol), compound amine75 (9.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 2-77. (Yield 60%, MS: [M+H] + =655)

[0266] Compound 2-78 [ka] Compound 2-BJ (10 g, 28.1 mmol), compound amine 76 (10.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-78. (Yield 61%, MS: [M+H] + =691)

[0267] Compound 2-79 [ka] Compound 2-BK (10 g, 28.1 mmol), compound amine 77 (11.8 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 2-79. (Yield 63%, MS: [M+H] + =741)

[0268] Compound 2-80 [ka] Compound 2-BJ (15 g, 42.2 mmol) and compound amine 78 (16.2 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound 2-80. (Yield 67%, MS: [M+H] + =641)

[0269] Compound 2-81 [ka] Compound 2-BG (15 g, 42.2 mmol) and compound amine 79 (21.8 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11.5 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 2-81. (Yield 61%, MS: [M+H] + =767)

[0270] Compound 2-82 [ka] Compound 2-BI (15 g, 42.2 mmol) and compound amine 80 (26.3 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.9 g of compound 2-82. (Yield 68%, MS: [M+H] + =869)

[0271] Compound 2-83 [ka] Compound 2-BH (15 g, 42.2 mmol) and compound amine 81 (20.2 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 2-83. (Yield 64%, MS: [M+H] + =731)

[0272] Compound 2-84 [ka] Compound 2-BG (15 g, 42.2 mmol) and compound amine 82 (21.8 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20 g of compound 2-84. (Yield 62%, MS: [M+H] + =767)

[0273] Compound 2-85 [ka] Compound 2-BL (15 g, 42.2 mmol) and compound amine 83 (22.9 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20 g of compound 2-85. (Yield 60%, MS: [M+H] + =793)

[0274] Compound 2-86 [ka] Compound 2-BG (15 g, 42.2 mmol) and compound amine 84 (23.5 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.5 g of compound 2-86. (Yield 69%, MS: [M+H] + =807)

[0275] Compound 2-87 [ka] Compound 2-BI (15 g, 42.2 mmol) and compound amine 85 (22.4 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-87. (Yield 69%, MS: [M+H] + =781)

[0276] Compound 2-88 [ka] Compound 2-BJ (15 g, 42.2 mmol) and compound amine 86 (20.6 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.6 g of compound 2-88. (Yield 66%, MS: [M+H] + =741)

[0277] Compound 2-89 [ka] Compound 2-BI (15 g, 42.2 mmol) and compound amine 87 (22.4 g, 44.3 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.5 g, 126.5 mmol) was dissolved in water (52 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.4 g of compound 2-89. (Yield 62%, MS: [M+H] + =781)

[0278] Compound 2-90 [ka] In a nitrogen atmosphere, compound 2-BN (10 g, 30.3 mmol), compound amine 88 (11.3 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 2-90. (Yield 66%, MS: [M+H] + =665)

[0279] Compound 2-91 [ka] Compound 2-BM (10 g, 30.3 mmol), compound amine 89 (12.8 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-91. (Yield 62%, MS: [M+H] + =715)

[0280] Compound 2-92 [ka] Compound 2-BP (10 g, 30.3 mmol), compound amine 90 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound 2-92. (Yield 66%, MS: [M+H] + =691)

[0281] Compound 2-93 [ka] Compound 2BQ (10 g, 30.3 mmol), compound amine 91 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, after which the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-93. (Yield 64%, MS: [M+H] + =691)

[0282] Compound 2-94 [ka] Compound 2-BP (15 g, 45.5 mmol) and compound amine 92 (25.6 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8 g of compound 2-94. (Yield 61%, MS: [M+H] + =785)

[0283] Compound 2-95 [ka] Compound 2-BN (15 g, 45.5 mmol) and compound amine 93 (26 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.6 g of compound 2-95. (Yield 68%, MS: [M+H] + =795)

[0284] Compound 2-96 [ka] Compound 2-BP (15 g, 45.5 mmol) and compound amine 94 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.6 g of compound 2-96. (Yield 69%, MS: [M+H] + =817)

[0285] Compound 2-97 [ka] Compound 2-BN (15 g, 45.5 mmol) and compound amine 95 (30.7 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.2 g of compound 2-97. (Yield 62%, MS: [M+H] + =893)

[0286] Compound 2-98 [ka] Compound 2-BR (15 g, 45.5 mmol) and compound amine 96 (21.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.1 g of compound 2-98. (Yield 64%, MS: [M+H] + =691)

[0287] Compound 2-99 [ka] Compound 2-BP (15 g, 45.5 mmol) and compound amine 97 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-99. (Yield 62%, MS: [M+H] + =817)

[0288] Compound 2-100 [ka] Compound 2-BN (15 g, 45.5 mmol) and compound amine 98 (24.7 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-100. (Yield 64%, MS: [M+H] + =767)

[0289] Compound 2-101 [ka] Compound 2-BP (15 g, 45.5 mmol) and compound amine 99 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-101. (Yield 60%, MS: [M+H] + =817)

[0290] Compound 2-102 [ka] Compound 2-BM (15 g, 45.5 mmol) and compound amine 100 (25.9 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.6 g of compound 2-102. (Yield 60%, MS: [M+H] + =791)

[0291] Compound 2-103 [ka] Compound 2-BO (15 g, 45.5 mmol) and compound amine 101 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26 g of compound 2-103. (Yield 70%, MS: [M+H] + =817)

[0292] Compound 2-104 [ka] Compound 2-BO (15 g, 45.5 mmol) and compound amine 102 (24.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.6 g of compound 2-104. (Yield 63%, MS: [M+H] + =791)

[0293] Compound 2-105 [ka] Compound 2-BN (15 g, 45.5 mmol) and compound amine 103 (27.1 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.7 g of compound 2-105. (Yield 69%, MS: [M+H] + =755)

[0294] Compound 2-106 [ka] In a nitrogen atmosphere, compound 2-AS (10 g, 35.8 mmol), compound amine 104 (13.8 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform and washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 2-106. (Yield 63%, MS: [M+H] + =629)

[0295] Compound 2-107 [ka] Compound 2-AS (15 g, 45.5 mmol) and compound amine 105 (21.2 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound 2-107. (Yield 61%, MS: [M+H] + =691)

[0296] Compound 2-108 [ka] Compound 2-BS (10 g, 35.8 mmol), compound amine 106 (13.8 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to xylene (200 ml) in a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was cooled to room temperature and the solvent was removed by reducing the pressure. Then, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated and treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 2-108. (Yield 63%, MS: [M+H] + =629)

[0297] Compound 2-109 [ka] Compound 2-BT (15 g, 45.5 mmol) and compound amine 107 (21.2 g, 47.8 mmol) were added to THF (300 ml) in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (18.9 g, 136.5 mmol) was dissolved in water (57 ml) and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium (0) (0.5 g, 1.0 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated, and anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound 2-109. (Yield 61%, MS: [M+H] + =691)

[0298] [Example] Example 1 A glass substrate coated with a 1,000 Å-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent dissolved therein and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was washed for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum deposition machine.

[0299] On the ITO transparent electrode thus prepared, the following HT-1 compound was formed to a thickness of 1150 Å, and at this time, the following A-1 compound was p-doped to a concentration of 1.5 wt % to form a hole injection layer. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a hole transport layer with a thickness of 800 Å. On the hole transport layer, the following EB-1 compound was vacuum-deposited to form an electron blocking layer with a thickness of 150 Å. On the electron blocking layer, the above-prepared compound 1-2, compound 2-1, and the following Dp-7 compound were vacuum-deposited in a weight ratio of 49:49:2 to form a red light-emitting layer with a thickness of 400 Å. On the light-emitting layer, the following HB-1 compound was vacuum-deposited to form a hole blocking layer with a thickness of 30 Å. On the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited in a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were sequentially deposited to a thickness of 12 Å and 1,000 Å on the electron injecting and transporting layer to form a negative electrode. [ka]

[0300] During the above process, the deposition rate of the organic material was maintained at 0.4-0.7 Å / sec, the deposition rate of the negative electrode lithium fluoride was maintained at 0.3 Å / sec, and the deposition rate of the aluminum was maintained at 2 Å / sec. The degree of vacuum during deposition was 2×10 -7 ~5×10 -6 Torr was maintained to fabricate an organic light-emitting device.

[0301] Examples 2 to 200 An organic light emitting device was manufactured in the same manner as in Example 1, except that in the manufacture of the light emitting layer, the compounds shown in Tables 1 to 8 below were used instead of Compound 1-2 and Compound 2-1, respectively.

[0302] Comparative Examples 1 to 188 An organic light-emitting device was manufactured in the same manner as in Example 1, except that in the manufacture of the light-emitting layer, compounds shown in Tables 9 to 17 below were used instead of Compound 1-2 and Compound 2-1. In Tables 9 to 17 below, Compounds B-1 to B-12 and C-1 to C-16 are as follows, respectively. [ka] [ka]

[0303] When a current was applied to the organic light-emitting devices manufactured in the above examples and comparative examples, the voltage and efficiency were measured (15 mA / cm 2 The results are shown in the table below. The lifespan T95 was measured based on 7000 nit as a standard, and T95 means the time (hr) until the initial lifespan decreases to 95%.

[0304] [Table 1]

[0305] [Table 2]

[0306] [Table 3]

[0307] [Table 4]

[0308] [Table 5]

[0309] [Table 6]

[0310]

Table 7

[0311]

Table 8

[0312]

Table 9

[0313]

Table 10

[0314]

Table 11

[0315]

Table 12

[0316]

Table 13

[0317]

Table 14

[0318]

Table 15

[0319]

Table 16

[0320] [Table 17]

[0321] When a current was applied to the organic light emitting devices fabricated in Examples 1 to 200 and Comparative Examples 1 to 188, the results in the above table were obtained. The red organic light emitting device of Example 1 uses materials that have been widely used in the past, and has a structure in which compound EB-1 is used as an electron blocking layer and Dp-7 is used as a dopant in the red light emitting layer. When the compounds B-1 to B-12 of the comparative examples and the compound of Chemical Formula 2 of the present invention were co-deposited together to form a red light emitting layer, the driving voltage generally increased and the efficiency and lifespan decreased compared to the combination of the present invention. When the compounds C-1 to C-16 of the comparative examples and the compound of Chemical Formula 1 of the present invention were co-deposited together to form a red light emitting layer, the driving voltage also increased and the efficiency and lifespan decreased.

[0322] From these results, it can be inferred that the reason for the improved driving voltage and increased efficiency and lifetime is that the combination of the compound of Chemical Formula 1 as the first host of the present invention and the compound of Chemical Formula 2 as the second host of the present invention transfers energy well to the red dopant in the red light-emitting layer. This ultimately confirmed that the combination of Chemical Formula 1 and Chemical Formula 2 of the present invention has a more stable equilibrium in the light-emitting layer than the combination of the compound of the comparative example, and electrons and holes combine to form excitons, thereby greatly increasing efficiency and lifetime. Therefore, it was confirmed that when the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present invention are co-deposited and used as a host for the red light-emitting layer, the driving voltage, luminous efficiency and lifetime characteristics of the organic light-emitting device can be improved. [Explanation of symbols]

[0323] 1 Board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Light-emitting layer 8 Electron transport layer

Claims

1. A positive electrode and A negative electrode; a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer includes (i) a compound represented by the following Chemical Formula 1, and (ii) a compound represented by the following Chemical Formula 2 or 3, [Chemical formula 1] 【Chemistry 460】 In the above Chemical Formula 1, L is a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; X is N; or CH, with the proviso that at least two of X are N; R is hydrogen, deuterium, a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; Ar １ and Ar ２ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl; [Chemical formula 2] 【Chemistry 461】 [Chemical formula 3] 【Chemistry 462】 In the above Chemical Formulas 2 and 3, R' is a substituent represented by the following chemical formula 4, or a substituted or unsubstituted aryl having 6 to 60 carbon atoms, When R' is a substituent represented by the following chemical formula 4, R' １ ~R' ６ are each independently hydrogen or deuterium; When R' is not a substituent represented by the following formula 4, R' １ ~R' ６ one of which is a substituent represented by the following chemical formula 4, and the rest are each independently hydrogen or deuterium, [Chemical formula 4] 【Chemistry 463】 In the above Chemical Formula 4, L' is a single bond, a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; L' １ and L' ２ each independently represents a single bond, a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, Ar' １ and Ar' ２ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of substituted or unsubstituted N, O, and S.

2. 2. The organic light-emitting device according to claim 1, wherein L is a single bond; phenylene; biphenyldiyl; or naphthylene.

3. The organic light-emitting device according to claim 1 , wherein all X's are N.

4. 4. The organic light-emitting device according to claim 1, wherein R is hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, triphenylenyl, fluoranthenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, or benzonaphthothiophenyl.

5. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of: 【Chemistry 464】 【Chemistry 465】 【Chemistry 466】 【Chemistry 467】 【Chemistry 468】 【Chemistry 469】 【Chemistry 470】 【Chemistry 471】 【Chemistry 472】 【Chemistry 473】 【Chemical 474】 【Chemistry 475】 【Chemistry 476】 【Chemistry 477】 【Chemistry 478】 【Chemical 479】 【Chemistry 480】 【Chemistry 481】 【Chemistry 482】 【Chemistry 483】 【Chemistry 484】 【Chemistry 485】 【Chemistry 486】 【Chemistry 487】 【Chemistry 488】 【Chemistry 489】 【Chemistry 490】 【Chemistry 491】 【Chemistry 492】 【Chemistry 493】 【Chemistry 494】 【Chemistry 495】 【Chemistry 496】 【Chemistry 497】 【Chemistry 498】 【Chemistry 499】 【Chemical 500】 【Chemistry 501】 【Chemistry 502】 【Chemistry 503】 【Chemistry 504】 【Chemistry 505】 【Chemistry 506】 【Chemistry 507】 【Chemistry 508】 【Chemistry 509】 【Chemistry 510】 【Chemistry 511】 【Chemistry 512】 【Chemistry 513】 【Chemistry 514】 【Chemistry 515】 【Chemistry 516】 【Chemistry 517】 【Chemistry 518】 【Chemistry 519】 【Chemistry 520】 【Chemistry 521】 【Chemistry 522】 【Chemistry 523】 【Chemistry 524】 【Chemistry 525】 【Chemistry 526】 【Chemistry 527】 【Chemistry 528】 【Chemistry 529】 【Chemistry 530】 【Chemistry 531】 【Chemistry 532】 【Chemistry 533】 【Chemical 534】 【Chemistry 535】 【Chemistry 536】 【Chemistry 537】 【Chemistry 538】 【Chemistry 539】 【Chemistry 540】 【Chemistry 541】 【Chemical 542】 【Chemistry 543】 【Chemical 544】 【Chemistry 545】 【Chemical 546】 【Chemical 547】 【Chemical 549】 【Chemistry 550】 【Chemistry 551】 【Chemistry 552】 【Chemistry 553】 【Chemical Formula 554】 【Chemistry 555】 【Chemistry 556】 【Chemistry 557】 【Chemistry 558】 【Chemical 559】 【Chemistry 560】 【Chemistry 561】 【Chemical 562】 【Chemistry 563】 【Chemical 564】 【Chemistry 565】 【Chemistry 566】 【Chemistry 567】 【Chemistry 568】 【Chemical 569】 【Chemistry 571】 【Chemistry 572】 【Chemistry 573】 【Chemical 574】 【Chemistry 575】 【Chemistry 576】 【Chemistry 577】 【Chemistry 578】 【Chemical 579】 【Chemistry 580】 【Chemistry 581】 【Chemistry 582】 【Chemistry 583】 【Chemistry 584】 【Chemistry 585】 【Chemistry 586】 【Chemistry 587】 【Chemistry 588】 【Chemistry 589】 【Chemistry 590】 【Chemistry 591】 【Chemistry 592】 【Chemistry 593】 【Chemistry 594】 【Chemistry 595】 【Chemistry 596】 【Chemistry 597】 【Chemistry 598】 【Chemistry 599】 【Chemical 600】 【Chemistry 601】 【Chemistry 602】 。

6. 2. The organic light emitting device according to claim 1, wherein R' is a substituent represented by Formula 4, or R' is phenyl, biphenyl, or naphthyl.

7. 7. The organic light-emitting device according to claim 1, wherein L' is a single bond, phenylene, biphenyldiyl, terphenyldiyl, naphthylene, or -(phenylene)-(naphthylene)-.

8. L' １ and L' ２ The organic light-emitting device according to claim 1 , wherein each of the groups is independently a single bond, phenylene, or biphenyldiyl.

9. Ar' １ and Ar' ２ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, 9H-carbazol-9-yl, or 9-phenyl-9H-carbazole.

10. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 2 or Chemical Formula 3 is any one selected from the group consisting of: 【Chemistry 603】 【Chemistry 604】 【Chemistry 605】 【Chemistry 606】 【Chemistry 607】 【Chemistry 608】 【Chemistry 609】 【Chemistry 610】 【Chemistry 611】 【Chemistry 612】 【Chemistry 613】 【Chemistry 614】 【Chemistry 615】 【Chemistry 616】 【Chemistry 617】 【Chemistry 618】 【Chemical Formula 619】 【Chemistry 620】 【Chemistry 621】 【Chemical Formula 622】 【Chemical Formula 623】 【Chemical Formula 624】 【Chemistry 625】 【Chemical 626】 【Chemical 627】 【Chemical Formula 628】 【Chemical Formula 629】 【Chemistry 630】 【Chemistry 631】 【Chemistry 632】 【Chemistry 633】 【Chemical Formula 634】 【Chemistry 635】 【Chemistry 636】 【Chemical 637】 【Chemical 638】 【Chemical 639】 【Chemistry 640】 【Chemistry 641】 【Chemical Formula 642】 【Chemical 643】 【Chemical Formula 644】 【Chemistry 645】 【Chemical 646】 【Chemical Formula 647】 【Chemical Formula 648】 【Chemical 649】 【Chemistry 650】 【Chemistry 651】 【Chemistry 652】 【Chemistry 653】 【Chemistry 654】 【Chemistry 655】 【Chemistry 656】 【Chemistry 657】 【Chemistry 658】 【Chemistry 659】 【Chemistry 660】 【Chemistry 661】 【Chemical 662】 【Chemical 663】 【Chemical 664】 【Chemical 665】 【Chemical Formula 666】 【Chemical 667】 【Chemical Formula 668】 【Chemical Formula 669】 【Chemistry 670】 【Chemistry 671】 【Chemical 672】 【Chemical 673】 【Chemical 674】 【Chemistry 675】 【Chemical 676】 【Chemical 677】 【Chemical 678】 【Chemical 679】 【Chemistry 680】 【Chemistry 681】 【Chemistry 682】 【Chemistry 683】 【Chemistry 684】 【Chemistry 685】 【Chemistry 686】 【Chemistry 687】 【Chemistry 688】 【Chemistry 689】 【Chemistry 690】 【Chemistry 691】 【Chemical Formula 692】 【Chemistry 693】 【Chemical Formula 694】 【Chemistry 695】 【Chemistry 696】 【Chemical Formula 697】 【Chemistry 698】 【Chemistry 699】 【Chemical 700】 【Chemistry 701】 【Chemistry 702】 【Chemistry 703】 【Chemistry 704】 【Chemistry 705】 【Chemistry 706】 【Chemistry 707】 【Chemistry 708】 【Chemistry 709】 【Chemistry 710】 【Chemistry 711】 【Chemistry 712】 【Chemistry 713】 【Chemical Formula 714】 【Chemistry 715】 【Chemical 716】 【Chemistry 717】 【Chemical 718】 【Chemical 719】 【Chemistry 720】 【Chemistry 721】 【Chemical 722】 【Chemical Formula 723】 【Chemical 724】 【Chemistry 725】 【Chemical 726】 【Chemical 727】 【Chemical 728】 【Chemical 729】 。

Images