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. 10-2021-0022497 filed on February 19, 2021 and Korean Patent Application No. 10-2022-0021927 filed on February 21, 2022, and all contents disclosed in the documents of said Korean patent applications 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 the above organic light emitting devices, there is a continuing demand for development of organic light emitting devices having 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 relates to 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; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer comprises a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2, which is an organic light-emitting device: [Chemical formula 1] [ka] In the above Chemical Formula 1, Ar1 and Ar2 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; L1 to L3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, R1 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; a is an integer from 0 to 7; [Chemical formula 2] [ka] In the above Chemical Formula 2, R'1~R' 12 one of which is the following chemical formula 3, and the rest are hydrogen or deuterium; [Chemical formula 3] [ka] In the above Chemical Formula 3, L'1 is a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; L'2 and L'3 each independently represent 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 N, O, and S. Effect of the Invention

[0009] The above-mentioned organic light-emitting device includes the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 in the light-emitting layer, thereby improving efficiency, lowering driving voltage, and / or improving life characteristics in the organic light-emitting device. [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 shows 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, 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, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, 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-listed substituents. For example, the "substituent having two or more substituents connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent having two phenyl groups connected.

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

[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 in one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In 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 a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc., but is not limited thereto.

[0024] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to 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, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

[0026] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aryl group among the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the alkyl group among 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 among the heteroarylamine. In this specification, the above-mentioned explanation regarding the alkenyl group is applicable to the alkenyl group among 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 heterocycle, 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, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; 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 having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0031] Hole injection layer The organic light-emitting device according to the present invention may further include a hole injection layer on the positive electrode, if necessary.

[0032] The hole injection layer is a layer that injects holes from the 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 addition, 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.

[0033] 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.

[0034] Hole transport layer The organic light-emitting device according to the present invention may optionally include a hole transport layer on the anode (or on the hole injection layer, if present).

[0035] The hole transport layer is a layer that receives holes from the positive electrode or the hole injection layer and transports the holes 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.

[0036] 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.

[0037] Electron Blocking Layer The organic light-emitting device according to the present invention may optionally include an electron blocking layer on the anode (or on the hole injection layer if a hole injection layer is present, or on the electron transport layer if an electron transport layer is present).

[0038] The electron blocking layer is a layer disposed between the hole transport layer and the light emitting layer to prevent the electrons injected from the anode from being recombined in the light emitting layer and passing to the hole transport layer, and is also called an electron inhibiting layer or an electron blocking layer. The electron blocking layer is preferably made of a material having a smaller electron affinity than the electron transport layer.

[0039] 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 electrode and the negative electrode. In general, the light-emitting layer includes a host material and a dopant material, and in the present invention, the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 are included as hosts.

[0040] Preferably, the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 1A: [Chemical formula 1A] [ka] In the above Chemical Formula 1A, Ar1, Ar2, L1 to L3, R1 and a are as defined in Chemical Formula 1 above.

[0041] Preferably, the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3: [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] In the above Chemical Formulas 1-1 to 1-3, Ar1, Ar2, L1 to L3, and R1 are as defined in Chemical Formula 1.

[0042] Preferably, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S;

[0043] More preferably, Ar1 and Ar2 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl;

[0044] Most preferably, Ar1 and Ar2 can each independently be any one selected from the group consisting of: [ka]

[0045] Preferably, L1 to L3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms,

[0046] More preferably, L1 to L3 may each independently be a single bond, phenylene, biphenylylene, or naphthylene;

[0047] Most preferably, L1 to L3 are each independently a single bond or any one selected from the group consisting of: [ka]

[0048] Preferably, R1 may be hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S;

[0049] More preferably, R1 can be hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, fluoranthenyl, dihydroindenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

[0050] Preferably, a may be 0 or 1.

[0051] Representative examples of the compound represented by Formula 1 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0052] The compound represented by Chemical Formula 1 can be prepared, for example, by the method shown in Reaction Scheme 1 below, and the remaining compounds can be prepared by similar methods. [Reaction Scheme 1] [ka] In the reaction formula 1, Ar1, Ar2, L1 to L3, R1 and a are as defined in the chemical formula 1, and X is a halogen, preferably, X is chloro or bromo.

[0053] The reaction scheme 1 is preferably carried out as a Suzuki coupling reaction in the presence of a palladium catalyst and a base, and the reactive group for the Suzuki coupling reaction can be changed according to those known in the art. The preparation method is more specifically described in the preparation examples described below.

[0054] Preferably, R'1 to R'3, R'5 to R'9, R' 11 and 'R' 12 One of the substituents is represented by the following chemical formula 3, and the rest are each independently hydrogen or deuterium, and R'4 and R' 10 may each independently be hydrogen or deuterium. More preferably, R'1 to R'3, R'5 to R'9, and R' 11 and 'R' 12One of the substituents is represented by the following chemical formula 3, and the rest are hydrogen, and R'4 and R' 10 may each be hydrogen.

[0055] Preferably, the compound represented by Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-6 below: [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] [Chemical formula 2-5] [ka] [Chemical formula 2-6] [ka] In the above Chemical Formula 2-1 to Chemical Formula 2-6, R'1~R' 12 , L′1 to L′3, Ar′1 and Ar′2 are as defined in Chemical Formula 2.

[0056] Preferably, L'1 is a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms; More preferably, L'1 can be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, or substituted or unsubstituted naphthalenediyl.

[0057] Most preferably, L'1 may be phenyl.

[0058] Preferably, L'2 and L'3 are each independently a single bond; a substituted or unsubstituted arylene having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S;

[0059] More preferably, L'2 and L'3 may each independently be a single bond, phenylene, biphenyldiyl, or naphthalenediyl.

[0060] Preferably, Ar'1 and Ar'2 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S,

[0061] More preferably, Ar'1 and Ar'2 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazole, dimethylfluorenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

[0062] More preferably, Ar'1 and Ar'2 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenyl-9H-carbazole, dimethylfluorenyl, benzo[b]naphtho[2,1-d]furanyl, benzo[b]naphtho[2,3-d]furanyl, benzo[b]naphtho[1,2-d]furanyl, benzo[b]naphtho[2,1-d]thiophenyl, benzo[b]naphtho[2,3-d]thiophenyl, or benzo[b]naphtho[1,2-d]thiophenyl.

[0063] Representative examples of the compound represented by Formula 2 are as follows: [ka] [ka]

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[0064] In the compound represented by the above formula 2, R1 to R 12 When any one of the above is a substituent represented by the following chemical formula 3 and the rest are hydrogen, it can be prepared, for example, by a preparation method shown in the following reaction formula 2, and the remaining compounds can also be prepared by a similar method. [Reaction Scheme 2] [ka] In the reaction formula 2, L'1 to L'3, Ar'1 and Ar'2 are as defined in the chemical formula 2, and X' is a halogen, preferably X' is chloro or bromo.

[0065] The reaction scheme 2 is preferably carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction, and the reactive group for the Suzuki coupling reaction can be changed according to those known in the art. The preparation method is more specifically described in the preparation examples described below.

[0066] Preferably, in the light-emitting layer, the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 is 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0067] Meanwhile, the light-emitting layer may further include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material used in an organic light-emitting device. For example, aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. are included. Specifically, 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 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, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0068] Preferably, the dopant material may be any one or more selected from the group consisting of: [ka] [ka] [ka] [ka]

[0069] Hole Blocking Layer The organic light-emitting device according to the present invention may optionally include a hole-blocking layer on the light-emitting layer.

[0070] The hole blocking layer is a layer disposed between the electron transport layer and the light emitting layer to prevent holes injected from the positive electrode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole suppression layer. A material having a large ionization energy is preferable for the hole blocking layer.

[0071] electron transport layer The organic light-emitting device according to the present invention may optionally include an electron transport layer on the light-emitting layer.

[0072] The electron transport layer is a layer that 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 transmission 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.

[0073] Specific examples of the electron transport material include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are those that have a low work function and are usually followed by an aluminum or silver layer. In particular, cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.

[0074] electron injection layer The organic light-emitting device according to the present invention may further comprise an electron injection layer on the light-emitting layer (or on the electron transport layer, if present) as required.

[0075] The electron injection layer is a layer that injects electrons from an electrode, and it is preferable to use a compound that has the ability to transport electrons, has an excellent electron injection effect from the negative electrode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin-film forming ability. 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, perylenetetracarboxylic acid, preolenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives. Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0076] 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a negative electrode 4.

[0077] 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, and then a material to be used as a negative electrode may be deposited thereon. In addition to this method, an organic light emitting device may be manufactured by depositing a negative electrode material on a substrate in the reverse order of the above-mentioned components, followed by a positive electrode material (WO2003 / 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, ink jet printing, screen printing, spraying, roll coating, and the like.

[0078] Meanwhile, the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and may be a bottom emission device which requires relatively high light emitting efficiency.

[0079] In the following, preferred examples are presented to aid in the understanding of the present invention. However, the following examples are provided only to facilitate the understanding of the present invention, and are not intended to limit the scope of the present invention.

[0080] [Production Example] Manufacturing Example 1-1 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz1 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water 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 further dissolved in chloroform and 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 20.9 g of compound sub1-A-1. (Yield 71%, MS: [M+H] + =484)

[0081] [ka] Compound sub1-A-1 (15 g, 31 mmol) and compound sub1 (6.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 12.3 g of compound 1-1. (Yield 66%, MS: [M+H] + =602)

[0082] Manufacturing Example 1-2 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 19.5 g of compound sub1-A-2. (Yield 74%, MS: [M+H] + =434)

[0083] [ka] Compound sub1-A-2 (15 g, 34.6 mmol) and compound sub2 (9.4 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.3 g of compound 1-2. (Yield 66%, MS: [M+H] + =626)

[0084] Manufacturing Example 1-3 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 23.2 g of compound sub1-A-3. (Yield 79%, MS: [M+H] + =484)

[0085] [ka] Compound sub1-A-3 (15 g, 31 mmol) and compound sub3 (7.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 1-3. (Yield 66%, MS: [M+H] + =632)

[0086] Manufacturing Example 1-4 [ka] Compound 1-A (15 g, 60.9 mmol) and compound Trz4 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 to separate the organic layer and the aqueous layer, and the organic layer was distilled. This was further dissolved in chloroform and 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 sub1-A-4. (Yield 70%, MS: [M+H] + =610)

[0087] [ka] Compound sub1-A-4 (15 g, 24.6 mmol) and compound sub4 (5.6 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (6.8 g, 49.2 mmol) was dissolved in 20 ml of water 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 further dissolved in chloroform and 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 11.2 g of compound 1-4. (Yield 60%, MS: [M+H] + =758)

[0088] Manufacturing Example 1-5 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz5 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 26.2 g of compound sub1-B-1. (Yield 77%, MS: [M+H] + =560)

[0089] [ka] Compound sub1-B-1 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 1-5. (Yield 80%, MS: [M+H] + =602)

[0090] Manufacturing Example 1-6 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 18.2 g of compound sub1-B-2. (Yield 62%, MS: [M+H] + =484)

[0091] [ka] Compound sub1-B-2 (15 g, 31 mmol) and compound sub6 (7.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 15.3 g of compound 1-6. (Yield 76%, MS: [M+H] + =650)

[0092] Manufacturing Example 1-7 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 20.8 g of compound sub1-B-3. (Yield 79%, MS: [M+H] + =434)

[0093] [ka] Compound sub1-B-3 (15 g, 34.6 mmol) and compound sub7 (8.6 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 15.4 g of compound 1-7. (Yield 74%, MS: [M+H] + =602)

[0094] Manufacturing Example 1-8 [ka] Compound sub1-B-2 (15 g, 31 mmol) and compound sub8 (8.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 15.5 g of compound 1-8. (Yield 75%, MS: [M+H] + =666)

[0095] Manufacturing Example 1-9 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz6 (22.4 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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)

[0096] [ka] Compound sub1-B-4 (15 g, 28.1 mmol) and compound sub9 (6 g, 28.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in 23 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 11.6 g of compound 1-9. (Yield 62%, MS: [M+H] + =666)

[0097] Manufacturing Example 1-10 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz7 (28.6 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 28.6 g of compound sub1-B-5. (Yield 74%, MS: [M+H] + =636)

[0098] [ka] Compound sub1-B-5 (15 g, 23.6 mmol) and compound sub5 (2.9 g, 23.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (6.5 g, 47.2 mmol) was dissolved in 20 ml of water 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 further dissolved in chloroform and 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 10.4 g of compound 1-10. (Yield 65%, MS: [M+H] + =678)

[0099] Manufacturing Example 1-11 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz8 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and stirred thoroughly, and then 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 further dissolved in chloroform and 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)

[0100] [ka] Compound sub1-B-6 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.9 g, 57.3 mmol) was dissolved in 24 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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)

[0101] Manufacturing Example 1-12 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 17.6 g of compound sub1-C-1. (Yield 60%, MS: [M+H] + =484)

[0102] [ka] Compound sub1-C-1 (15 g, 31 mmol) and compound sub10 (5.3 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 12.8 g of compound 1-12. (Yield 72%, MS: [M+H] + =576)

[0103] Manufacturing Example 1-13 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz9 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 23.5 g of compound sub1-C-2. (Yield 69%, MS: [M+H] + =560)

[0104] [ka] Compound sub1-C-2 (15 g, 26.8 mmol) and compound sub10 (4.6 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 14 g of compound 1-13. (Yield 80%, MS: [M+H] + =652)

[0105] Manufacturing Example 1-14 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 20.5 g of compound sub1-C-3. (Yield 66%, MS: [M+H] + =510)

[0106] [ka] Compound sub1-C-3 (15 g, 29.4 mmol) and compound sub11 (7.3 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.1 g, 58.8 mmol) was dissolved in 24 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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)

[0107] Manufacturing Example 1-15 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 18.7 g of compound sub1-C-4. (Yield 71%, MS: [M+H] + =434)

[0108] [ka] Compound sub1-C-4 (15 g, 37.1 mmol) and compound sub12 (9.7 g, 37.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.3 g, 74.3 mmol) was dissolved in 31 ml of water and added, and the mixture was thoroughly stirred, 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 further dissolved in chloroform and 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)

[0109] Manufacturing Example 1-16 [ka] Compound sub1-C-3 (15 g, 26.8 mmol) and compound sub13 (7.4 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 16.2 g of compound 1-16. (Yield 80%, MS: [M+H] + =758)

[0110] Manufacturing Example 1-17 [ka] Compound sub1-C-4 (15 g, 34.6 mmol) and compound sub14 (7.7 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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)

[0111] Manufacturing Example 1-18 [ka] Compound sub1-C-1 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 g of compound 1-18. (Yield 63%, MS: [M+H] + =616)

[0112] Manufacturing Example 1-19 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz11 (22.4 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 22.4 g of compound sub1-C-5. (Yield 69%, MS: [M+H] + =534)

[0113] [ka] Compound sub1-C-5 (15 g, 28.1 mmol) and compound sub15 (6 g, 28.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in 23 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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)

[0114] Manufacturing Example 1-20 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz12 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 21 g of compound sub1-C-6. (Yield 66%, MS: [M+H] + =524)

[0115] [ka] Compound sub1-C-6 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 12.3 g of compound 1-20. (Yield 70%, MS: [M+H] + =616)

[0116] Manufacturing Example 1-21 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 26.2 g of compound sub1-C-7. (Yield 77%, MS: [M+H] + =560)

[0117] [ka] Compound sub1-C-7 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 10.5 g of compound 1-21. (Yield 65%, MS: [M+H] + =602)

[0118] Manufacturing Example 1-22 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz14 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 23.9 g of compound sub1-D-1. (Yield 67%, MS: [M+H] + =586)

[0119] [ka] Compound sub1-D-1 (15 g, 25.6 mmol) and compound sub5 (3.1 g, 25.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in 32 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 10.3 g of compound 1-22. (Yield 64%, MS: [M+H] + =628)

[0120] Manufacturing Example 1-23 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 20 g of compound sub1-D-2. (Yield 76%, MS: [M+H] + =434)

[0121] [ka] Compound sub1-D-2 (15 g, 34.6 mmol) and compound sub16 (9.1 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14 g of compound 1-23. (Yield 66%, MS: [M+H] + =616)

[0122] Manufacturing Example 1-24 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 20.8 g of compound sub1-D-3. (Yield 67%, MS: [M+H] + =510)

[0123] [ka] Compound 1-D-3 (15 g, 29.4 mmol) and compound 17 (7.7 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water and added, and stirred thoroughly, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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)

[0124] Manufacturing Example 1-25 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz15 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 21.3 g of compound sub1-D-4. (Yield 67%, MS: [M+H] + =524)

[0125] [ka] Compound sub1-D-4 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 10.7 g of compound 1-25. (Yield 61%, MS: [M+H] + =616)

[0126] Manufacturing Example 1-26 [ka] Compound sub1-D-3 (15 g, 29.4 mmol) and compound sub18 (6.2 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.3 g of compound 1-26. (Yield 76%, MS: [M+H] + =642)

[0127] Manufacturing Example 1-27 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz16 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 27.1 g of compound sub1-D-5. (Yield 73%, MS: [M+H] + =610)

[0128] [ka] Compound sub1-D-5 (15 g, 24.6 mmol) and compound sub9 (5.2 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water 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 further dissolved in chloroform and 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 12.8 g of compound 1-27. (Yield 70%, MS: [M+H] + =742)

[0129] Manufacturing Example 1-28 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 20.8 g of compound sub1-D-6. (Yield 61%, MS: [M+H] + =560)

[0130] [ka] Compound sub1-D-6 (15 g, 26.8 mmol) and compound sub10 (4.6 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 12.2 g of compound 1-28. (Yield 70%, MS: [M+H] + =652)

[0131] Manufacturing Example 1-29 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 17.1 g of compound sub1-E-1. (Yield 65%, MS: [M+H] + =434)

[0132] [ka] Compound sub1-E-1 (15 g, 34.6 mmol) and compound sub2 (9.4 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.5 g of compound 1-29. (Yield 67%, MS: [M+H] + =626)

[0133] Manufacturing Example 1-30 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz9 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and stirred thoroughly, and then 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 further dissolved in chloroform and 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)

[0134] [ka] Compound sub1-E-2 (15 g, 26.8 mmol) and compound sub19 (7 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 15.9 g of compound 1-30. (Yield 80%, MS: [M+H] + =742)

[0135] Manufacturing Example 1-31 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz17 (22.4 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 25.3 g of compound sub1-E-3. (Yield 78%, MS: [M+H] + =534)

[0136] [ka] Compound sub1-E-3 (15 g, 28.1 mmol) and compound sub20 (7.8 g, 28.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.6 g, 84.3 mmol) was dissolved in 35 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 14.8 g of compound 1-31. (Yield 72%, MS: [M+H] + =732)

[0137] Manufacturing Example 1-32 [ka] Compound sub1-E-1 (15 g, 34.6 mmol) and compound sub21 (7.7 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 1-32. (Yield 65%, MS: [M+H] + =576)

[0138] Manufacturing Example 1-33 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz15 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 25.5 g of compound sub1-E-4. (Yield 80%, MS: [M+H] + =524)

[0139] [ka] Compound sub1-E-4 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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)

[0140] Manufacturing Example 1-34 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 17.6 g of compound sub1-E-5. (Yield 60%, MS: [M+H] + =484)

[0141] [ka] Compound sub1-E-5 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 11.4 g of compound 1-34. (Yield 60%, MS: [M+H] + =616)

[0142] Manufacturing Example 1-35 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 21.7 g of compound sub1-E-6. (Yield 70%, MS: [M+H] + =510)

[0143] [ka] Compound sub1-E-6 (15 g, 29.4 mmol) and compound sub22 (7.7 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.6 g of compound 1-35. (Yield 72%, MS: [M+H] + =692)

[0144] Manufacturing Example 1-36 [ka] Compound sub1-E-5 (15 g, 31 mmol) and compound sub23 (8.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 12.4 g of compound 1-36. (Yield 60%, MS: [M+H] + =666)

[0145] Manufacturing Example 1-37 [ka] Compound sub1-E-5 (15 g, 31 mmol) and compound sub10 (5.3 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.1 g of compound 1-37. (Yield 79%, MS: [M+H] + =576)

[0146] Manufacturing Example 1-38 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz18 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 24.1 g of compound sub1-E-7. (Yield 65%, MS: [M+H] + =610)

[0147] [ka] Compound sub1-E-7 (15 g, 24.6 mmol) and compound sub5 (3 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water 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 further dissolved in chloroform and 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 10.1 g of compound 1-38. (Yield 63%, MS: [M+H] + =652)

[0148] Manufacturing Example 1-39 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 26.2 g of compound sub1-E-8. (Yield 77%, MS: [M+H] + =560)

[0149] [ka] Compound sub1-E-8 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 10.9 g of compound 1-39. (Yield 68%, MS: [M+H] + =602)

[0150] Manufacturing Example 1-40 [ka] Compound 1-F (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 19.2 g of compound sub1-F-1. (Yield 73%, MS: [M+H] + =434)

[0151] [ka] Compound 1-F-1 (15 g, 34.6 mmol) and compound sub6 (8.5 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.7 g of compound 1-40. (Yield 71%, MS: [M+H] + =600)

[0152] Manufacturing Example 1-41 [ka] Compound 1-F (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water 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 further dissolved in chloroform and 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 21.1 g of compound sub1-F-2. (Yield 68%, MS: [M+H] + =510)

[0153] [ka] Compound sub1-F-2 (15 g, 29.4 mmol) and compound sub1 (5.8 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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)

[0154] Manufacturing Example 1-42 [ka] Compound Trz7 (15g, 31.9mmol) and compound sub9 (6.8g, 31.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2g, 95.8mmol) was dissolved in 40ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) 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 further dissolved in chloroform and 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 15.2g of compound 1-42. (Yield 79%, MS: [M+H] + =602)

[0155] Manufacturing Example 1-43 [ka] Compound Trz16 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in 42ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) 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 further dissolved in chloroform and 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 15g of compound 1-43. (Yield 77%, MS: [M+H] + =576)

[0156] Manufacturing Example 1-44 [ka] Compound Trz4 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in 42ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) 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 further dissolved in chloroform and 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 14.2g of compound 1-44. (Yield 73%, MS: [M+H] + =576)

[0157] Manufacturing Example 1-45 [ka] Compound Trz1 (15 g, 35.7 mmol) and compound sub9 (7.6 g, 35.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in 44 ml of water 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 further dissolved in chloroform and 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 12.2 g of compound 1-45. (Yield 62%, MS: [M+H] + =552)

[0158] Manufacturing Example 1-46 [ka] Compound Trz19 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in 42ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) 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 further dissolved in chloroform and 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 13.6g of compound 1-46. (Yield 70%, MS: [M+H] + =576)

[0159] Manufacturing Example 1-47 [ka] Compound Trz20 (15 g, 35.9 mmol) and compound sub9 (7.6 g, 35.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in 45 ml of water 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 further dissolved in chloroform and 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 g of compound 1-47. (Yield 76%, MS: [M+H] + =550)

[0160] Manufacturing Example 1-48 [ka] Compound Trz3 (15 g, 47.2 mmol) and compound sub24 (9.7 g, 47.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in 59 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 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 further dissolved in chloroform and 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 13 g of compound sub1-G-1. (Yield 62%, MS: [M+H] + =444)

[0161] [ka] Compound sub1-G-1 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 15.2 g of compound 1-48. (Yield 78%, MS: [M+H] + =576)

[0162] Manufacturing Example 1-49 [ka] Compound Trz15 (15 g, 41.9 mmol) and compound sub25 (8.7 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water 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 further dissolved in chloroform and 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 12.6 g of compound sub1-G-2. (Yield 62%, MS: [M+H] + =484)

[0163] [ka] Compound sub1-G-2 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 13.7 g of compound 1-49. (Yield 72%, MS: [M+H] + =616)

[0164] Manufacturing Example 1-50 [ka] Compound Trz21 (15 g, 36.8 mmol) and compound sub26 (5.8 g, 36.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 ml of water 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 further dissolved in chloroform and 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 12.8 g of compound sub1-G-3. (Yield 72%, MS: [M+H] + =484)

[0165] [ka] Compound sub1-G-3 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 13.2 g of compound 1-50. (Yield 69%, MS: [M+H] + =616)

[0166] Manufacturing Example 1-51 [ka] Compound Trz16 (15 g, 33.8 mmol) and compound sub27 (5.3 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 13.3 g of compound sub1-G-4. (Yield 76%, MS: [M+H] + =520)

[0167] [ka] Compound sub1-G-4 (15 g, 28.8 mmol) and compound sub9 (6.1 g, 28.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 13.3 g of compound 1-51. (Yield 71%, MS: [M+H] + =652)

[0168] Manufacturing Example 1-52 [ka] Compound Trz22 (15 g, 36.8 mmol) and compound sub28 (5.8 g, 36.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 ml of water 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 further dissolved in chloroform and 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 12.8 g of compound sub1-G-5. (Yield 72%, MS: [M+H] + =484)

[0169] [ka] Compound sub1-G-5 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 13 g of compound 1-52. (Yield 68%, MS: [M+H] + =616)

[0170] Manufacturing Example 1-53 [ka] Compound Trz23 (15 g, 34.6 mmol) and compound sub27 (5.4 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 11.3 g of compound sub1-G-6. (Yield 64%, MS: [M+H] + =510)

[0171] [ka] Compound sub1-G-6 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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)

[0172] Manufacturing Example 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 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 14.4 g of compound sub1-E-9. (Yield 70%, MS: [M+H] + =610)

[0173] [ka] Compound sub1-E-9 (15 g, 24.6 mmol) and compound sub5 (3 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water 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 further dissolved in chloroform and 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 12.2 g of compound 1-54. (Yield 76%, MS: [M+H] + =652)

[0174] Manufacturing Example 1-55 [ka] Compound Trz2 (15 g, 56 mmol) and compound sub24 (11.6 g, 56 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in 70 ml of water 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 further dissolved in chloroform and 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)

[0175] [ka] Compound sub1-G-7 (15 g, 38.1 mmol) and formula 1-B (9.4 g, 38.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 ml of water 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 further dissolved in chloroform and 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 13.8 g of compound sub1-B-7. (Yield 65%, MS: [M+H] + =560)

[0176] [ka] Compound sub1-B-7 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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)

[0177] Manufacturing Example 1-56 [ka] Compound Trz24 (15 g, 38.1 mmol) and compound sub25 (9.4 g, 38.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 ml of water 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 further dissolved in chloroform and 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 13.8 g of compound sub1-G-8. (Yield 65%, MS: [M+H] + =560)

[0178] [ka] Compound sub1-G-8 (15 g, 30 mmol) and compound sub9 (6.4 g, 30 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.4 g, 90 mmol) was dissolved in 37 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 13.4 g of compound 1-56. (Yield 71%, MS: [M+H] + =632)

[0179] Manufacturing Example 1-57 [ka] Compound Trz25 (15 g, 41.9 mmol) and compound sub24 (8.7 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water 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 further dissolved in chloroform and 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 12.4 g of compound sub1-G-9. (Yield 61%, MS: [M+H] + =484)

[0180] [ka] Compound sub1-G-9 (15 g, 31 mmol) and formula 1-F (7.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 12.5 g of compound sub1-F-3. (Yield 62%, MS: [M+H] + =650)

[0181] [ka] Compound sub1-F-3 (15 g, 23.1 mmol) and compound sub5 (2.8 g, 23.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in 29 ml of water 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 further dissolved in chloroform and 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 12.8 g of compound 1-57. (Yield 80%, MS: [M+H] + =692)

[0182] Manufacturing Example 1-58 [ka] Compound Trz26 (15 g, 33.8 mmol) and compound sub26 (5.3 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 10.5 g of compound sub1-G-10. (Yield 60%, MS: [M+H] + =520)

[0183] [ka] Compound sub1-G-10 (15 g, 28.8 mmol) and compound 1-D (7.1 g, 28.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 g of compound sub1-D-7. (Yield 76%, MS: [M+H] + =686)

[0184] [ka] Compound sub1-D-7 (15 g, 21.9 mmol) and compound sub5 (2.7 g, 21.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.1 g, 65.6 mmol) was dissolved in 27 ml of water 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 further dissolved in chloroform and 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 9.9 g of compound 1-58. (Yield 62%, MS: [M+H] + =728)

[0185] Manufacturing Example 1-59 [ka] Compound Trz15 (15 g, 41.9 mmol) and compound sub24 (8.7 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water 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 further dissolved in chloroform and 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 12.4 g of compound sub1-G-11. (Yield 61%, MS: [M+H] + =484)

[0186] [ka] Compound sub1-G-11 (15 g, 28.8 mmol) and compound 1-F (7.1 g, 28.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 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 further dissolved in chloroform and 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 g of compound sub1-F-4. (Yield 76%, MS: [M+H] + =686)

[0187] [ka] Compound sub1-F-4 (15 g, 23.1 mmol) and compound sub5 (2.8 g, 23.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in 29 ml of water 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 further dissolved in chloroform and 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 12.1 g of compound 1-59. (Yield 76%, MS: [M+H] + =692)

[0188] Manufacturing Example 1-60 [ka] Compound Trz12 (15 g, 41.9 mmol) and compound sub28 (6.6 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water 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 further dissolved in chloroform and 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 11.1 g of compound sub1-G-12. (Yield 61%, MS: [M+H] + =434)

[0189] [ka] Compound sub1-G-12 (15 g, 34.6 mmol) and compound 1-D (8.5 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 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 further dissolved in chloroform and 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 13.6 g of compound sub1-D-8. (Yield 79%, MS: [M+H] + =500)

[0190] [ka] Compound sub1-D-8 (15 g, 25 mmol) and compound sub10 (4.3 g, 25 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.4 g, 75 mmol) was dissolved in 31 ml of water 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 further dissolved in chloroform and 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 13.3 g of compound 1-60. (Yield 77%, MS: [M+H] + =692)

[0191] Manufacturing Example 1-61 [ka] Compound Trz27 (15g, 31.9mmol) and compound sub9 (6.8g, 31.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2g, 95.8mmol) was dissolved in 40ml of water and added, and the mixture was thoroughly stirred, after which Tetrakis(triphenylphosphine)palladium(0) (0.4g, 0.3mmol) 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 further dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10g of compound 1-61. (Yield 52%, MS: [M+H] + =602)

[0192] Manufacturing Example 1-62 [ka] Compound Trz28 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in 42ml of water and added, and after thorough stirring, Tetrakis(triphenylphosphine)palladium(0) (0.4g, 0.3mmol) 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 further dissolved in chloroform and 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 12.2g of compound 1-62. (Yield 63%, MS: [M+H] + =576)

[0193] Manufacturing Example 1-63 [ka] Compound Trz29 (15g, 31.9mmol) and compound sub9 (6.8g, 31.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2g, 95.8mmol) was dissolved in 40ml of water and added, and the mixture was thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.4g, 0.3mmol) 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 further dissolved in chloroform and 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 12.7g of compound 1-63. (Yield 66%, MS: [M+H] + =602)

[0194] Manufacturing Example 1-64 [ka] Compound Trz30 (15g, 31.9mmol) and compound sub9 (6.8g, 31.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (13.2g, 95.8mmol) was dissolved in 40ml of water and added, and stirred thoroughly, and then Tetrakis(triphenylphosphine)palladium(0) (0.4g, 0.3mmol) 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 further dissolved in chloroform and 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 13.2g of compound 1-64. (Yield 69%, MS: [M+H] + =602)

[0195] Manufacturing Example 1-65 [ka] Compound Trz31 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (14g, 101.4mmol) was dissolved in 42ml of water and added, and stirred thoroughly, and then Tetrakis(triphenylphosphine)palladium(0) (0.4g, 0.3mmol) 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 further dissolved in chloroform and 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 14.6g of compound 1-65. (Yield 75%, MS: [M+H] + =576)

[0196] Manufacturing Example 1-66 [ka] Compound 1-B (15 g, 60.9 mmol) and compound Trz30 (28.6 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and stirred thoroughly, and then Tetrakis (triphenylphosphine) palladium (0) (0.7 g, 0.6 mmol) was added. After reacting for 12 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 further dissolved in chloroform and 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)

[0197] [ka] Compound sub1-B-7 (15 g, 23.6 mmol) and compound sub5 (2.9 g, 23.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (9.8 g, 70.7 mmol) was dissolved in 29 ml of water and added, and the mixture was thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.3 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 further dissolved in chloroform and 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)

[0198] Manufacturing Example 1-67 [ka] Compound 1-C (15 g, 60.9 mmol) and compound Trz32 (25.6 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and stirred thoroughly, and then Tetrakis (triphenylphosphine) palladium (0) (0.7 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 further dissolved in chloroform and 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)

[0199] [ka] Compound sub1-C-8 (15 g, 25.6 mmol) and compound sub5 (3.1 g, 25.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in 32 ml of water and added, and the mixture was thoroughly stirred, and then Tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.3 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 further dissolved in chloroform and 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 10.6 g of compound 1-67. (Yield 66%, MS: [M+H] + =628)

[0200] Manufacturing Example 1-68 [ka] Compound 1-D (15 g, 60.9 mmol) and compound Trz33 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and stirred thoroughly, and then Tetrakis (triphenylphosphine) palladium (0) (0.7 g, 0.6 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 further dissolved in chloroform and 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)

[0201] [ka] Compound 1-D-7 (15 g, 24.6 mmol) and compound 5 (3 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water and added, and stirred thoroughly, and then Tetrakis (triphenylphosphine) palladium (0) (0.3 g, 0.2 mmol) was added. After reacting for 11 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 further dissolved in chloroform and 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 11.2 g of compound 1-68. (Yield 70%, MS: [M + H] + =652)

[0202] Manufacturing Example 1-69 [ka] Compound 1-E (15 g, 60.9 mmol) and compound Trz34 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and the mixture was thoroughly stirred, and then Tetrakis (triphenylphosphine) palladium (0) (0.7 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 further dissolved in chloroform and 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)

[0203] [ka] Compound sub1-E-9 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and stirred thoroughly, and then Tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.3 mmol) was added. After reacting for 11 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 further dissolved in chloroform and 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 10 g of compound 1-69. (Yield 62%, MS: [M+H] + =602)

[0204] Manufacturing Example 2-1 [ka] Compound A (15g, 57.1mmol) and compound amine 1 (34g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 29.1g of compound 2-1. (Yield 68%, MS: [M+H] + =750)

[0205] Manufacturing Example 2-2 [ka] Compound A (15g, 57.1mmol) and compound amine 2 (32.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 31g of compound 2-2. (Yield 75%, MS: [M+H] + =724)

[0206] Manufacturing Example 2-3 [ka] Compound A (15g, 57.1mmol) and compound amine 3 (24.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.2g of compound 2-3. (Yield 74%, MS: [M+H] + =598)

[0207] Manufacturing Example 2-4 [ka] Compound A (15g, 57.1mmol) and compound amine 4 (32.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 26.8g of compound 2-4. (Yield 65%, MS: [M+H] + =724)

[0208] Manufacturing Example 2-5 [ka] Compound A (15g, 57.1mmol) and compound amine 5 (31.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 26.5g of compound 2-5. (Yield 65%, MS: [M+H] + =714)

[0209] Manufacturing Example 2-6 [ka] Compound A (15g, 57.1mmol) and compound amine 6 (28.3g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 27.2g of compound 2-6. (Yield 73%, MS: [M+H] + =654)

[0210] Manufacturing Example 2-7 [ka] Compound A (15g, 57.1mmol) and compound amine 7 (27.2g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 28.3g of compound 2-7. (Yield 78%, MS: [M+H] + =637)

[0211] Manufacturing Example 2-8 [ka] Compound A (15g, 57.1mmol) and compound amine 8 (24.3g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 21.1g of compound 2-8. (Yield 63%, MS: [M+H] + =588)

[0212] Manufacturing Example 2-9 [ka] Compound A (15g, 57.1mmol) and compound amine 9 (29.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.2g of compound 2-9. (Yield 63%, MS: [M+H] + =674)

[0213] Manufacturing Example 2-10 [ka] Compound A (15g, 57.1mmol) and compound amine 10 (29.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 27.3g of compound 2-10. (Yield 71%, MS: [M+H] + =674)

[0214] Manufacturing Example 2-11 [ka] Compound A (15g, 57.1mmol) and compound amine 11 (29.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 26.5g of compound 2-11. (Yield 69%, MS: [M+H] + =674)

[0215] Manufacturing Example 2-12 [ka] Compound A (15g, 57.1mmol) and compound amine 12 (32.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.8g of compound 2-12. (Yield 60%, MS: [M+H] + =724)

[0216] Manufacturing Example 2-13 [ka] Compound A (15g, 57.1mmol) and compound amine 13 (34g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 33.8g of compound 2-13. (Yield 79%, MS: [M+H] + =750)

[0217] Manufacturing Example 2-14 [ka] Compound A (15 g, 57.1 mmol) and compound amine 14 (31 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 30.3 g of compound 2-14. (Yield 76%, MS: [M+H] + =700)

[0218] Manufacturing Example 2-15 [ka] Compound B (15g, 57.1mmol) and compound amine 15 (24.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 21.8g of compound 2-15. (Yield 64%, MS: [M+H] + =598)

[0219] Manufacturing Example 2-16 [ka] Compound B (15g, 57.1mmol) and compound amine 16 (31g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 26.3g of compound 2-16. (Yield 66%, MS: [M+H] + =700)

[0220] Manufacturing Example 2-17 [ka] Compound B (15g, 57.1mmol) and compound amine 17 (29.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 27.7g of compound 2-17. (Yield 72%, MS: [M+H] + =674)

[0221] Manufacturing Example 2-18 [ka] Compound B (15g, 57.1mmol) and compound amine 18 (27.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.4g of compound 2-18. (Yield 66%, MS: [M+H] + =648)

[0222] Manufacturing Example 2-19 [ka] Compound B (15g, 57.1mmol) and compound amine 19 (28.1g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 27.5g of compound 2-19. (Yield 74%, MS: [M+H] + =652)

[0223] Manufacturing Example 2-20 [ka] Compound B (15g, 57.1mmol) and compound amine 20 (30.3g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 28.3g of compound 2-20. (Yield 72%, MS: [M+H] + =688)

[0224] Manufacturing Example 2-21 [ka] Compound B (15g, 57.1mmol) and compound amine 21 (28.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.8g of compound 2-21. (Yield 68%, MS: [M+H] + =664)

[0225] Manufacturing Example 2-22 [ka] Compound B (15g, 57.1mmol) and compound amine 22 (30.3g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 30.6g of compound 2-22. (Yield 78%, MS: [M+H] + =688)

[0226] Manufacturing Example 2-23 [ka] Compound C (15g, 57.1mmol) and compound amine 23 (26.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.6g of compound 2-23. (Yield 69%, MS: [M+H] + =624)

[0227] Manufacturing Example 2-24 [ka] Compound C (15g, 57.1mmol) and compound amine 24 (27.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 27.3g of compound 2-24. (Yield 74%, MS: [M+H] + =648)

[0228] Manufacturing Example 2-25 [ka] Compound C (15g, 57.1mmol) and compound amine 25 (26.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 23.5g of compound 2-25. (Yield 66%, MS: [M+H] + =624)

[0229] Manufacturing Example 2-26 [ka] Compound C (15g, 57.1mmol) and compound amine 26 (30.1g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.2g of compound 2-26. (Yield 62%, MS: [M+H] + =684)

[0230] Manufacturing Example 2-27 [ka] Compound C (15g, 57.1mmol) and compound amine 27 (26.7g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.7g of compound 2-27. (Yield 69%, MS: [M+H] + =628)

[0231] Manufacturing Example 2-28 [ka] Compound D (15 g, 57.1 mmol) and compound amine 28 (26.5 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 24.2 g of compound 2-28. (Yield 68%, MS: [M+H] + =624)

[0232] Manufacturing Example 2-29 [ka] Compound D (15 g, 57.1 mmol) and compound amine 29 (32.5 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 24.8 g of compound 2-29. (Yield 60%, MS: [M+H] + =724)

[0233] Manufacturing Example 2-30 [ka] Compound D (15g, 57.1mmol) and compound amine 30 (31g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 31.9g of compound 2-30. (Yield 80%, MS: [M+H] + =700)

[0234] Manufacturing Example 2-31 [ka] Compound D (15 g, 57.1 mmol) and compound amine 31 (29.5 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 30.8 g of compound 2-31. (Yield 80%, MS: [M+H] + =674)

[0235] Manufacturing Example 2-32 [ka] Compound D (15 g, 57.1 mmol) and compound amine 32 (29.5 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 28.1 g of compound 2-32. (Yield 73%, MS: [M+H] + =674)

[0236] Manufacturing Example 2-33 [ka] Compound D (15g, 57.1mmol) and compound amine 33 (28.9g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 29.9g of compound 2-33. (Yield 79%, MS: [M+H] + =664)

[0237] Manufacturing Example 2-34 [ka] Compound D (15g, 57.1mmol) and compound amine 34 (29.1g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 27.4g of compound 2-34. (Yield 72%, MS: [M+H] + =668)

[0238] Manufacturing Example 2-35 [ka] Compound D (15 g, 57.1 mmol) and compound amine 35 (30.3 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 23.5 g of compound 2-35. (Yield 60%, MS: [M+H] + =688)

[0239] Manufacturing Example 2-36 [ka] Compound D (15 g, 57.1 mmol) and compound amine 36 (26.7 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 25.4 g of compound 2-36. (Yield 71%, MS: [M+H] + =628)

[0240] Manufacturing Example 2-37 [ka] Compound D (15 g, 57.1 mmol) and compound amine 37 (31 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 31.9 g of compound 2-37. (Yield 80%, MS: [M+H] + =700)

[0241] Manufacturing Example 2-38 [ka] Compound D (15 g, 57.1 mmol) and compound amine 38 (24.9 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 23.5 g of compound 2-38. (Yield 69%, MS: [M+H] + =598)

[0242] Manufacturing Example 2-39 [ka] Compound D (15 g, 57.1 mmol) and compound amine 39 (32.5 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 30.6 g of compound 2-39. (Yield 74%, MS: [M+H] + =724)

[0243] Manufacturing Example 2-40 [ka] Compound D (15 g, 57.1 mmol) and compound amine 40 (34 g, 59.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water 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 further dissolved in chloroform and 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 30.8 g of compound 2-40. (Yield 72%, MS: [M+H] + =750)

[0244] Manufacturing Example 2-41 [ka] Compound D (15g, 57.1mmol) and compound amine 41 (32.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 26g of compound 2-41. (Yield 63%, MS: [M+H] + =724)

[0245] Manufacturing Example 2-42 [ka] Compound E (15g, 57.1mmol) and compound amine 42 (26.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.6g of compound 2-42. (Yield 72%, MS: [M+H] + =624)

[0246] Manufacturing Example 2-43 [ka] Compound E (15g, 57.1mmol) and compound amine 43 (29.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 29.2g of compound 2-43. (Yield 76%, MS: [M+H] + =674)

[0247] Manufacturing Example 2-44 [ka] Compound E (15g, 57.1mmol) and compound amine 44 (32.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 26.4g of compound 2-44. (Yield 64%, MS: [M+H] + =724)

[0248] Manufacturing Example 2-45 [ka] Compound E (15g, 57.1mmol) and compound amine 45 (22.7g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 22.4g of compound 2-45. (Yield 70%, MS: [M+H] + =562)

[0249] Manufacturing Example 2-46 [ka] Compound E (15g, 57.1mmol) and compound amine 46 (31.8g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.6g of compound 2-46. (Yield 63%, MS: [M+H] + =713)

[0250] Manufacturing Example 2-47 [ka] Compound E (15g, 57.1mmol) and compound amine 47 (25.7g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 24.4g of compound 2-47. (Yield 70%, MS: [M+H] + =612)

[0251] Manufacturing Example 2-48 [ka] Compound E (15g, 57.1mmol) and compound amine 48 (31g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 31.5g of compound 2-48. (Yield 79%, MS: [M+H] + =700)

[0252] Manufacturing Example 2-49 [ka] Compound E (15g, 57.1mmol) and compound amine 49 (32.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.2g of compound 2-49. (Yield 61%, MS: [M+H] + =724)

[0253] Manufacturing Example 2-50 [ka] Compound F (15g, 57.1mmol) and compound amine 50 (26.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.3g of compound 2-50. (Yield 71%, MS: [M+H] + =624)

[0254] Manufacturing Example 2-51 [ka] Compound F (15g, 57.1mmol) and compound amine 51 (31g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.2g of compound 2-51. (Yield 63%, MS: [M+H] + =700)

[0255] Manufacturing Example 2-52 [ka] Compound F (15g, 57.1mmol) and compound amine 52 (29.5g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 28.1g of compound 2-52. (Yield 73%, MS: [M+H] + =674)

[0256] Manufacturing Example 2-53 [ka] Compound F (15g, 57.1mmol) and compound amine 53 (31g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 25.9g of compound 2-53. (Yield 65%, MS: [M+H] + =700)

[0257] Manufacturing Example 2-54 [ka] Compound F (15g, 57.1mmol) and compound amine 54 (34g, 59.9mmol) were added to 300ml of THF under a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.7g, 171.3mmol) was dissolved in 71ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.6mmol) 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 further dissolved in chloroform and 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 30.4g of compound 2-54. (Yield 71%, MS: [M+H] + =750)

[0258] [Example] Example 1 A glass substrate coated with a 1000Å-thick thin film of ITO (indium tin oxide) was placed in distilled water containing detergent 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 cleaned 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 cleaning device. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition device.

[0259] On the ITO transparent electrode thus prepared, the following compound HI-1 was formed as a hole injection layer with a thickness of 1150 Å, and the following compound A-1 was p-doped with a concentration of 1.5 wt %. The following compound HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 800 Å. Then, the following compound EB-1 was vacuum-deposited on the hole transport layer with a thickness of 150 Å to form an electron blocking layer. Then, the prepared compounds 1-2, 2-1 and Dp-7 were vacuum-deposited on the EB-1 deposition film in a weight ratio of 49:49:2 to form a red light-emitting layer with a thickness of 400 Å. The following compound HB-1 was vacuum-deposited on the light-emitting layer with a thickness of 30 Å to form a hole blocking layer. Then, the following compound ET-1 and the following LiQ compound were vacuum-deposited on the hole blocking layer in a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) was sequentially deposited to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron injecting and transporting layer to form a negative electrode. [ka]

[0260] During the above process, the deposition rate of the organic material was maintained at 0.4 to 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 aluminum was maintained at 2 Å / sec. The degree of vacuum during deposition was 2×10 -7 ~5×10-6 Torr was maintained to manufacture an organic light emitting device.

[0261] Example 2 to Example 200 An organic light emitting device was prepared in the same manner as in Example 1, except that the first host compound and the second host compound shown in Tables 1 to 5 were co-deposited in a ratio of 1:1 instead of Compound 1-2 and / or Compound 2-1 in the organic light emitting device of Example 1.

[0262] Comparative Example 1 to Comparative Example 60 An organic light emitting device was manufactured in the same manner as in Example 1, except that the first host compound and the second host compound shown in Tables 6 and 7 were co-deposited in a ratio of 1:1 instead of Compound 1-2 and / or Compound 2-1 in the organic light emitting device of Example 1. The structures of Compounds B-1 to B-12 in Tables 6 and 7 are as follows. [ka]

[0263] Comparative Example 61 to Comparative Example 132 An organic light emitting device was manufactured in the same manner as in Example 1, except that the first host compound and the second host compound shown in Tables 8 and 9 were co-deposited in a ratio of 1:1 instead of Compound 1-2 and / or Compound 2-1 in the organic light emitting device of Example 1. The structures of Compounds C-1 to C-9 in Tables 8 and 9 are as follows. [ka]

[0264] [Experimental Example] When a current was applied to the organic light-emitting devices manufactured in Examples 1 to 200 and Comparative Examples 1 to 132, the voltage and efficiency were measured (15 mA / cm 2 The results are shown in Tables 1 to 9 below. The lifespan T95 was measured based on 7000 nits, and T95 means the time required for the lifespan to decrease to 95% from the initial lifespan.

[0265] [Table 1]

Table 1

[0266]

Table 2

[0267] [Table 2]

Table 3

[0268]

Table 4

[0269] [Table 3]

Table 5

[0270]

Table 6

[0271] [Table 4]

Table 7

[0272]

Table 8

[0273] [Table 5]

Table 9

[0274]

Table 10

[0275] [Table 6] [Table 11]

[0276] [Table 12]

[0277] [Table 7] [Table 13]

[0278] [Table 8] [Table 14]

[0279] [Table 9] [Table 15]

[0280] [Table 16]

[0281] When a current was applied to the organic light emitting devices fabricated in Examples 1 to 200 and Comparative Examples 1 to 132, the results shown in Tables 1 to 9 were obtained. The red organic light emitting device of Example 1 used materials that have been widely used in the past as components thereof, and used compound EB-1 as an electron blocking layer and compound Dp-7 as a dopant in the red light emitting layer.

[0282] As shown in Tables 6 and 7, when any one of the comparative compounds B-1 to B-12 and the compound represented by Chemical Formula 2 of the present invention were co-deposited and used as a red light-emitting layer, the driving voltage was generally increased and the efficiency and lifespan were decreased compared to the combination of the present invention. As shown in Tables 8 and 9, when any one of the comparative compounds C-1 to C-9 and the compound represented by Chemical Formula 1 of the present invention were co-deposited and used as a red light-emitting layer, the driving voltage was also increased and the efficiency and lifespan were decreased.

[0283] From this, it can be seen that when a combination of a compound represented by Chemical Formula 1 as a first host and a compound represented by Chemical Formula 2 as a second host of the present invention is used, energy transfer to the red dopant in the red light-emitting layer is improved and a more stable balance is achieved in the light-emitting layer, so that electrons and holes combine to form excitons, thereby improving the driving voltage and increasing efficiency and lifetime.

[0284] In conclusion, it was confirmed that when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 of the present invention are co-deposited and used as a host for a red light-emitting layer, the driving voltage, luminous efficiency and life characteristics of an organic light-emitting device can be improved. [Explanation of symbols]

[0285] 1 Board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Electron Blocking Layer 8 Hole Blocking Layer 9 Electron injection and transport layer

Claims

1. Positive electrode; A negative electrode; and A light-emitting layer between the positive electrode and the negative electrode, the light-emitting layer is a red light-emitting layer, The light-emitting layer includes a compound represented by the following Chemical Formula 1A and a compound represented by the following Chemical Formula 2: [Chemical formula 1A] 【Chemistry 541】 In the above Chemical Formula 1A, 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, L １ ~L ３ each independently represents a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, R １ 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, a is an integer from 0 to 7; [Chemical formula 2] 【Chemistry 539】 In the above Chemical Formula 2, R' １ ~R' １２ one of which is the following chemical formula 3, and the rest are hydrogen or deuterium; [Chemical formula 3] 【Chemistry 540】 In the above Chemical Formula 3, L' １ is phenylene which is unsubstituted or substituted with one phenyl, biphenyldiyl which is unsubstituted or substituted with one phenyl, naphthalenediyl which is unsubstituted or substituted with one phenyl, or 【Chemical 738】 and L' ２ and L' ３ 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. The compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3. [Chemical formula 1-1] 【Chemical 542】 [Chemical formula 1-2] 【Chemistry 543】 [Chemical formula 1-3] 【Chemical 544】 In the above Chemical Formulas 1-1 to 1-3, Ar １ and Ar ２ , L １ ~L ３ and R １ is as defined in claim 1.

3. Ar １ and Ar ２ The organic light-emitting device of claim 1 , wherein each independently is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.

4. L １ ~L ３ Each of the groups independently represents a single bond or any one selected from the group consisting of: 【Chemistry 545】 。

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

6. The organic light-emitting device according to claim 1 , wherein a is 0 or 1.

7. 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: 【Chemical 546】 【Chemical 547】 【Chemistry 548】 【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 570】 【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】 【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 622】 【Chemical Formula 623】 【Chemical 624】 【Chemistry 625】 【Chemical 626】 【Chemical Formula 627】 【Chemical 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 Formula 643】 【Chemical 644】 【Chemistry 645】 【Chemical Formula 646】 【Chemical 647】 【Chemical Formula 648】 【Chemical Formula 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 666】 【Chemical Formula 667】 【Chemical Formula 668】 【Chemical Formula 669】 【Chemistry 670】 【Chemistry 671】 【Chemical 672】 【Chemical 673】 【Chemical 674】 【Chemistry 675】 【Chemical Formula 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 714】 【Chemistry 715】 【Chemical 716】 【Chemistry 717】 【Chemical 718】 【Chemical 719】 【Chemistry 720】 【Chemistry 721】 【Chemical 722】 【Chemical 723】 【Chemical 724】 【Chemistry 725】 【Chemical 726】 【Chemical 727】 【Chemical 728】 【Chemical 729】 【Chemistry 730】 【Chemistry 731】 。

8. L' ２ and L' ３ The organic light-emitting device according to claim 1 , wherein each of the is independently a single bond, phenylene, phenylene substituted with one phenyl, biphenyldiyl, biphenyldiyl substituted with one phenyl, or naphthalenediyl.

9. Ar' １ and Ar' ２ The organic light-emitting device according to claim 1 , wherein each independently is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, dimethylfluorenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

10. The organic light-emitting device according to claim 1, wherein the compound represented by Chemical Formula 2 is any one selected from the group consisting of: 【Chemistry 740】 【Chemical Formula 741】 【Chemical 742】 【Chemical 743】 【Chemical 744】 【Chemical 745】 【Chemical 747】 【Chemical 748】 【Chemical 749】 【Chemistry 750】 【Chemical 752】 【Chemical 753】 【Chemical 754】 【Chemistry 755】 【Chemical 756】 【Chemical 758】 【Chemical 759】 【Chemistry 760】 【Chemical 761】 【Chemical 762】 【Chemical 764】 【Chemical 765】 【Chemical 766】 【Chemical 768】 【Chemical 769】 【Chemical 771】 【Chemical 772】 【Chemical 773】 【Chemical 775】 【Chemical 776】 【Chemical 778】 【Chemical 779】 【Chemistry 780】 【Chemical 782】 【Chemical 783】 【Chemistry 785】 【Chemical 786】 【Chemical 787】 【Chemical 789】 【Chemical 790】 【Chemical 793】 【Chemical 794】 【Chemical 797】 【Chemical 798】 【Chemistry 801】 【Chemical 802】 【Chemistry 805】 【Chemistry 806】 【Chemistry 807】 【Chemistry 808】 【Chemistry 809】 【Chemical 810】 【Chemistry 812】 【Chemistry 813】 【Chemistry 814】 【Chemistry 815】 【Chemical 816】 【Chemical 818】 【Chemistry 819】 【Chemistry 820】 【Chemistry 821】 【Chemistry 822】 【Chemical 824】 【Chemistry 825】 【Chemistry 826】 【Chemical 827】 【Chemistry 828】 【Chemistry 830】 【Chemistry 832】 【Chemistry 833】 【Chemistry 834】 【Chemistry 835】 【Chemistry 836】 【Chemistry 837】 【Chemistry 839】 【Chemistry 840】 【Chemistry 841】 【Chemistry 842】 【Chemistry 843】 【Chemical 844】 【Chemistry 845】 【Chemistry 846】 【Chemistry 847】 【Chemistry 848】 【Chemistry 849】 【Chemical 850】 【Chemistry 851】 【Chemistry 852】 【Chemistry 853】 【Chemistry 854】 【Chemistry 855】 【Chemistry 856】 【Chemistry 857】 【Chemistry 858】 【Chemistry 859】 【Chemistry 860】 【Chemistry 861】 【Chemistry 862】 【Chemistry 863】 【Chemistry 864】 【Chemistry 865】 【Chemistry 866】 【Chemistry 867】 【Chemistry 868】 【Chemistry 869】 【Chemistry 870】 【Chemistry 871】 【Chemistry 872】 【Chemistry 873】 【Chemistry 874】 【Chemistry 875】 【Chemistry 876】 【Chemistry 877】 【Chemistry 878】 【Chemistry 879】 【Chemical 880】 【Chemistry 881】

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