Organic light-emitting element

Abstract

The present invention provides an organic light emitting device.

Description

Technical Field

[0001] [Cross - reference to Related Applications] This application claims the benefit of priority based on Korean Patent Application No. 10 - 2021 - 0044140, filed on April 5, 2021, and all the contents disclosed in the literature of the Korean patent application are included as part of this specification.

[0002] The present invention relates to an organic light - emitting device.

Background Art

[0003] Generally, the organic light - emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light - emitting device utilizing the organic light - emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and many studies are being conducted due to its excellent luminance, driving voltage, and response speed characteristics. 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 often has a multilayer structure composed of different substances in order to improve the efficiency and safety of the organic light - emitting device. For example, it may consist of a hole injection layer, a hole transport layer, a light - emitting layer, an electron transport layer, an electron injection layer, etc. In such a structure of the organic light - emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode and electrons are injected from the negative electrode. When the injected holes and electrons come into contact, an exciton is formed, and when this exciton falls back to the ground state again, light is emitted.

[0004] There has been a continuous demand for the development of new materials for the organic substances used in the organic light - emitting devices as described above.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] The present invention relates to an organic light-emitting device with improved driving voltage, efficiency, and lifespan.

Means for Solving the Problems

[0007] To solve the above problems, 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, wherein the light-emitting layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [Chemical Formula 1]

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Advantages of the Invention

[0008] The above-described organic light-emitting device is excellent in driving voltage, efficiency, and lifespan.

Brief Description of the Drawings

[0009]

Figure 1

Figure 2

Figure 3

Embodiments for Carrying Out the Invention

[0010] Hereinafter, it will be described in more detail to assist in understanding the present invention.

[0011] In the present invention,

Chemical Formula

[0012] In the present invention, the term "substituted or unsubstituted" means deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfinyl group; an arylsulfinyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the exemplified substituents linked together. For example, the "substituent with two or more substituents linked together" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may also be interpreted as a substituent with two phenyl groups linked together.

[0013] In the present invention, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, compounds having the following structures may be used, but are not limited thereto. [Chem.]

[0014] In the present specification, the oxygen of the ester group 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, compounds having the following structural formulas may be used, but are not limited thereto. [Chem.]

[0015] In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, compounds having the following structures may be used, but are not limited thereto.

Chemical formula

[0016] In this specification, specific examples of the silyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc.

[0017] In this specification, specific examples of the boron group include, but are not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, etc.

[0018] In this specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0019] 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 the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohectylmethyl, 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, etc., but are not limited thereto.

[0020] In this specification, the alkenyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples 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, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0021] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0022] In this 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. As the monocyclic aryl group, the aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. As the polycyclic aryl group, the aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0023] In this 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,

Chemical formula

[0024] In this specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heterocyclic group include, but are not limited to, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinoprazinyl group, an isoquinolinyl group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group.

[0025] In this specification, among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group, the description regarding the aryl group as described above is applicable to the aryl group. In this specification, among the aralkyl group, alkylaryl group, and alkylamine group, the description regarding the alkyl group as described above is applicable to the alkyl group. In this specification, regarding the heteroaryl of heteroarylamine, the description regarding the heterocyclic group as described above is applicable. In this specification, regarding the alkenyl group of the aralkenyl group, the description regarding the alkenyl group as described above is applicable. In this specification, regarding arylene, except that it is a divalent group, the description regarding the aryl group as described above is applicable. In this specification, regarding heteroarylene, except that it is a divalent group, the description regarding the heterocyclic group as described above is applicable. In this specification, regarding the hydrocarbon ring, except that it is not a monovalent group and is formed by bonding two substituents, the description regarding the aryl group or cycloalkyl group as described above is applicable. In this specification, regarding the heterocycle, except that it is not a monovalent group and is formed by bonding two substituents, the description regarding the heterocyclic group as described above is applicable.

[0026] Hereinafter, the present invention will be described in detail for each component.

[0027] Positive electrode and negative electrode The positive electrode and negative electrode used in the present invention mean the electrodes used in the organic light-emitting element.

[0028] As the positive electrode material, a material with a large work function is generally preferred so that hole injection into the organic layer is smooth. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0029] As the negative electrode material, a material with a small work function is preferably used so that electron injection into the organic layer is easy. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0030] Light-emitting layer The light-emitting layer used in the present invention means a layer that can emit light in the visible light region by combining holes and electrons transmitted from the positive electrode and the negative electrode. Generally, the light-emitting layer includes a host material and a dopant material, and the present invention includes the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 as hosts.

[0031] The compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 may each have one or more hydrogens substituted with deuterium. That is, in the chemical formula 1, n may be an integer of 1 or more, and one or more substituents among L and Ar1 to Ar3 may be substituted with deuterium. Also, in the chemical formula 2, n' may be an integer of 1 or more, and one or more substituents among L' and Ar'1 to Ar'3 may be substituted with deuterium. The chemical formula 1 is represented by the following chemical formula 1-1 according to the bonding position of dibenzofuran and triazine: [Chemical formula 1-1] [Chem.] In the chemical formula 1-1, L, Ar1 to Ar3, D, and n are as defined in the chemical formula 1.

[0032] Preferably, L is a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms, and Ar1 and Ar2 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a heteroaryl having 2 to 20 carbon atoms containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S, and Ar3 is a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a heteroaryl having 2 to 20 carbon atoms containing any one or more selected from the group consisting of substituted or unsubstituted N, O, and S.

[0033] Preferably, L is a single bond; phenylene; or naphthalenediyl.

[0034] Preferably, Ar1 and Ar2 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; (naphthyl)naphthyl; dibenzofuranyl; or dibenzothiophenyl.

[0035] Preferably, Ar3 is hydrogen; phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; fluoranthenyl; triphenylenyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthofuranyl; or benzonaphthothiophenyl.

[0036] In the above, (naphthyl)phenyl means phenyl substituted with one naphthyl; (phenyl)naphthyl means naphthyl substituted with one phenyl; (naphthyl)naphthyl means naphthyl substituted with one naphthyl.

[0037] In the above, benzonaphthofuranyl specifically refers to benzo[b]naphtho[2,1-d]furan (

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[0038] In one embodiment, L is a single bond; phenylene; or naphthalenediyl, and Ar1 and Ar2 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; (naphthyl)naphthyl; dibenzofuranyl; or dibenzothiophenyl.

[0039] In one embodiment, Ar1 and Ar2 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; (naphthyl)naphthyl; dibenzofuranyl; or dibenzothiophenyl, and Ar3 is hydrogen; phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; fluoranthenyl; triphenylenyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthofuranyl; or benzonaphthothiophenyl.

[0040] In one embodiment, L is a single bond; phenylene; or naphthalenediyl, and Ar3 is hydrogen; phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; fluoranthenyl; triphenylenyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthofuranyl; or benzonaphthothiophenyl.

[0041] In one embodiment, L is a single bond; phenylene; or naphthalenediyl, and Ar1 and Ar2 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; (naphthyl)naphthyl; dibenzofuranyl; or dibenzothiophenyl, and Ar3 is hydrogen; phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; fluoranthenyl; triphenylenyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthofuranyl; or benzonaphthothiophenyl.

[0042] Typical examples of the compound represented by the chemical formula 1 are as follows: [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical] [Chemical]

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[0043] Further, the present invention provides a method for producing the compound represented by the chemical formula 1.

[0044] For example, the compound represented by the chemical formula 1 may be produced by a production method such as Reaction Formula 1. [Reaction Formula 1] [Chemical formula]

[0045] In the Reaction Formula 1, the remainder except for X1 and X2 is as defined above, and X1 and X2 are each independently a halogen, and more preferably each independently bromo or chloro.

[0046] The Reaction Formula 1 is a Suzuki coupling reaction, and it is preferably carried out in the presence of a palladium catalyst and a base. The reaction groups for the Suzuki coupling reaction can be changed according to those known in the art.

[0047] The production method of the compound represented by the chemical formula 1 will be more specifically described in the production examples described later.

[0048] The chemical formula 2 has a structure including a core in which a benzoxazole ring is fused to a benzofuran ring and an arylamine substituent bonded thereto.

[0049] Specifically, the chemical formula 2 is represented by the following Chemical Formula 2-1 or 2-2: [Chemical Formula 2-1] [Chemical formula] [Chemical Formula 2-2] [Chemical formula] In the Chemical Formulas 2-1 and 2-2, L', Ar'1 to Ar'3, D, and n' are as defined in the chemical formula 2.

[0050] Preferably, L' is a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms.

[0051] Preferably, L' is a single bond; phenylene; or biphenyldiyl.

[0052] Preferably, Ar'1 is a substituted or unsubstituted aryl having 6 to 20 carbon atoms, more preferably phenyl.

[0053] Preferably, Ar'2 and Ar'3 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a heteroaryl having 2 to 20 carbon atoms containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

[0054] More preferably, Ar'2 and Ar'3 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; (naphthyl)phenyl; (phenyl)naphthyl; (naphthyl)biphenylyl; (naphthyl)naphthyl; [(phenyl)naphthyl]phenyl; dibenzofuranyl; dibenzothiophenyl; (dibenzofuranyl)phenyl; (dibenzothiophenyl)phenyl; phenanthrenyl; (phenanthrenyl)phenyl; 9,9-dimethylfluorenyl; or 9-phenylcarbazolyl.

[0055] In the above, (naphthyl)phenyl means phenyl substituted with one naphthyl; (phenyl)naphthyl means naphthyl substituted with one phenyl; (naphthyl)biphenylyl means biphenylyl substituted with one naphthyl; (naphthyl)naphthyl means naphthyl substituted with one naphthyl; [(phenyl)naphthyl]phenyl means phenyl substituted with the above (phenyl)naphthyl; (dibenzofuranyl)phenyl means phenyl substituted with one dibenzofuranyl; (dibenzothiophenyl)phenyl means phenyl substituted with one dibenzothiophenyl.

[0056] In one embodiment, L' is a single bond; phenylene; or biphenyldiyl, and Ar'1 is phenyl.

[0057] In one embodiment, L' is a single bond; phenylene; or biphenyldiyl, and Ar'2 and Ar'3 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; (naphthyl)phenyl; (phenyl)naphthyl; (naphthyl)biphenylyl; (naphthyl)naphthyl; [(phenyl)naphthyl]phenyl; dibenzofuranyl; dibenzothiophenyl; (dibenzofuranyl)phenyl; (dibenzothiophenyl)phenyl; phenanthrenyl; (phenanthrenyl)phenyl; 9,9-dimethylfluorenyl; or 9-phenylcarbazolyl.

[0058] In one embodiment, L' is a single bond; phenylene; or biphenyldiyl, Ar'1 is phenyl, and Ar'2 and Ar'3 are each independently phenyl; biphenylyl; terphenylyl; naphthyl; (naphthyl)phenyl; (phenyl)naphthyl; (naphthyl)biphenylyl; (naphthyl)naphthyl; [(phenyl)naphthyl]phenyl; dibenzofuranyl; dibenzothiophenyl; (dibenzofuranyl)phenyl; (dibenzothiophenyl)phenyl; phenanthrenyl; (phenanthrenyl)phenyl; 9,9-dimethylfluorenyl; or 9-phenylcarbazolyl.

[0059] Typical examples of the compound represented by Chemical Formula 2 are as follows:

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[0060] Furthermore, the present invention provides a method for producing the compound represented by Chemical Formula 2.

[0061] For example, the compound represented by Chemical Formula 2 may be produced by a production method such as Reaction Formula 2-1. Further, when L' is a single bond, the compound represented by Chemical Formula 2 may be produced by a production method such as Reaction Formula 2-2: [Reaction Formula 2-1] [Chemical Formula] [Reaction Formula 2-2] [Chemical Formula] In Reaction Formulas 2-1 and 2-2, the remainder except for X' is as defined above, and X' is independently a halogen, more preferably independently bromo or chloro.

[0062] Reaction Formula 2-1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the Suzuki coupling reaction can be changed according to those known in the art.

[0063] Reaction Formula 2-2 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reaction groups for the amine substitution reaction can be changed according to those known in the art.

[0064] The method for producing the compound represented by Chemical Formula 2 is further embodied in the production examples described below.

[0065] 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 1:99 to 99:1, 5:95 to 95:5, or 10:90 to 90:10.

[0066] The dopant material is not particularly limited as long as it is a substance used in an organic light-emitting element. For example, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, as the aromatic amine derivative, there are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periflanthene having an arylamino group, and as the styrylamine compound, there is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and a substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. Further, as the metal complex, there are iridium complexes, platinum complexes, etc., but are not limited thereto.

[0067] In one embodiment, as the dopant material, one or more of the following compounds can be used, but are not limited thereto:

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[0068] Hole transport layer The organic light-emitting element according to the present invention may include a hole transport layer between the light-emitting layer and the positive electrode.

[0069] The hole transport layer is a layer that receives holes from 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 transfer them to the light-emitting layer is suitable, and a material with high mobility for holes is preferred.

[0070] Specific examples of the hole transport material include arylamine-based organic substances, conductive polymers, and block copolymers that have both a conjugated part and a non-conjugated part, but are not limited thereto.

[0071] Hole injection layer The organic light-emitting device according to the present invention may further include a hole injection layer between the positive electrode and the hole transport layer, if necessary.

[0072] The hole injection layer is a layer that injects holes from the electrode. As the hole injection material, a compound having the ability to transport holes, having an excellent hole injection effect from the positive electrode, an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the transfer of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and having excellent thin film forming ability is preferred. Further, 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.

[0073] Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0074] Electron blocking layer The organic light-emitting device according to the present invention may include an electron blocking layer between the hole transport layer and the light-emitting layer, if necessary.

[0075] The electron suppression layer prevents electrons injected from the negative electrode from being recombined in the light-emitting layer and passing to the hole transport layer, and is also called an electron blocking layer. A substance having a smaller electron affinity than the electron transport layer is preferable for the electron suppression layer.

[0076] Electron transport layer The organic light-emitting device according to the present invention may include an electron transport layer between the light-emitting layer and the negative electrode.

[0077] The electron transport layer receives electrons from the negative electrode or an electron injection layer formed on the negative electrode and transports the electrons to the light-emitting layer, and also suppresses the transfer of holes from the light-emitting layer. As the electron transport material, a substance that can favorably receive electron injection from the negative electrode and transfer it to the light-emitting layer, and has a high mobility with respect to electrons is preferable.

[0078] Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer is used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are normal materials having a low work function followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.

[0079] Electron injection layer The organic light-emitting device according to the present invention may further include an electron injection layer between the electron transport layer and the negative electrode as needed.

[0080] The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the negative electrode and an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the transfer of excitons generated in the light-emitting layer to the hole injection layer, and it is preferable to use a compound having excellent thin film forming ability.

[0081] Specific examples of the material used in the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0082] Examples of the metal complex compound include lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinato)chloride, gallium bis(2-methyl-8-quinolinato)(o-cresolato), aluminum bis(2-methyl-8-quinolinato)(1-naphtholato), gallium bis(2-methyl-8-quinolinato)(2-naphtholato), etc., but are not limited thereto.

[0083] According to an embodiment of the present invention, the electron transport material and the electron injection material can be simultaneously vapor-deposited to manufacture a single layer of the electron injection and transport layer.

[0084] Hole blocking layer The organic light-emitting device according to the present invention may include a hole blocking layer between the electron transport layer and the light-emitting layer, if necessary.

[0085] The hole blocking layer prevents holes injected from the positive electrode from passing to the electron transport layer without recombination in the light-emitting layer, and a material having a large ionization energy is preferably used for the hole blocking layer.

[0086] Organic light-emitting device The structure of the organic light-emitting device according to the present invention is shown in FIG. 1. FIG. 1 is a diagram showing an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Further, FIG. 2 is a diagram showing an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, an electron injection layer 8, and a negative electrode 4. Further, FIG. 3 is a diagram showing an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 3, a hole blocking layer 10, an electron injection and transport layer 11, and a negative electrode 4.

[0087] The organic light-emitting device according to the present invention can be manufactured by sequentially laminating the above-described structures. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal, a metal oxide having conductivity, or an alloy thereof is vapor-deposited on a substrate to form a positive electrode, and after forming each of the above-described layers thereon, a substance used as a negative electrode is further vapor-deposited thereon to manufacture the device.

[0088] In addition to this method, an organic light-emitting device can be made by vapor-depositing in reverse order from the negative electrode material to the positive electrode material in the above-described configuration on a substrate (WO2003 / 012890). Further, the light-emitting layer can be formed by a solution coating method as well as a vacuum evaporation method for the host and the dopant. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0089] The organic light-emitting device according to the present invention may be a bottom emission element, a top emission element, or a double-sided emission element, and particularly may be a bottom emission element that requires relatively high luminous efficiency.

[0090] The manufacture of the organic light-emitting device according to the present invention described above will be specifically described in the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereby.

[0091] [Examples] [Synthesis Example 1: Production of the Compound of Chemical Formula 1] Synthesis Example 1-1 [Chemical Formula]

[0092] Under a nitrogen atmosphere, Chemical Formula 1-A (15 g, 60.9 mmol) and Trz1 (19.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-A-1. (Yield 71%, MS: [M+H]+ = 484)

[0093] Under a nitrogen atmosphere, sub1-A-1 (15 g, 31 mmol) and sub1 (6.1 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0094] Synthesis Example 1-2

Chemical formula

[0095] Under a nitrogen atmosphere, Chemical formula 1-A (15 g, 60.9 mmol) and Trz2 (16.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-A-2. (Yield 74%, MS: [M+H]+ = 434)

[0096] Under a nitrogen atmosphere, sub1-A-2 (15 g, 34.6 mmol) and sub2 (9.4 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0097] Synthesis Example 1-3

Chemical formula

[0098] Under a nitrogen atmosphere, Chemical formula 1-A (15 g, 60.9 mmol) and Trz3 (19.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-A-3. (Yield 79%, MS: [M+H]+ = 484)

[0099] Under a nitrogen atmosphere, sub1-A-3 (15 g, 31 mmol) and sub3 (7.1 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0100] Synthesis Example 1-4

Chemical formula

[0101] Under a nitrogen atmosphere, Chemical formula 1-A (15 g, 60.9 mmol) and Trz4 (27 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-A-4. (Yield 70%, MS: [M+H]+ = 610)

[0102] Under a nitrogen atmosphere, sub1-A-4 (15 g, 24.6 mmol) and sub4 (5.6 g, 24.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (6.8 g, 49.2 mmol) was dissolved in 20 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. 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)

[0103] Synthesis Example 1-5

Chemical formula

[0104] Under a nitrogen atmosphere, chemical formula 1-B (15 g, 60.9 mmol) and Trz5 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of sub1-B-1. (Yield 77%, MS: [M+H]+ = 560)

[0105] Under a nitrogen atmosphere, sub1-B-1 (15 g, 26.8 mmol) and sub5 (3.3 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0106] Synthesis Example 1-6

Chemical formula

[0107] Under a nitrogen atmosphere, Chemical formula 1-B (15 g, 60.9 mmol) and Trz3 (19.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-B-2. (Yield 62%, MS: [M+H]+ = 484)

[0108] Under a nitrogen atmosphere, sub1-B-2 (15 g, 31 mmol) and sub6 (7.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0109] Synthesis Example 1-7

Chemical formula

[0110] Under a nitrogen atmosphere, Chemical formula 1-B (15 g, 60.9 mmol) and Trz2 (16.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-B-3. (Yield 79%, MS: [M+H]+ = 434)

[0111] Under a nitrogen atmosphere, sub1-B-3 (15 g, 34.6 mmol) and sub7 (8.6 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0112] Synthesis Example 1-8

Chemical formula

[0113] Under a nitrogen atmosphere, sub1-B-2 (15 g, 31 mmol) and sub8 (8.1 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0114] Synthesis Example 1-9

Chemical formula

[0115] Under a nitrogen atmosphere, 1-B (15 g, 60.9 mmol) and Trz6 (22.4 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-B-4. (Yield 73%, MS: [M+H]+ = 534)

[0116] Under a nitrogen atmosphere, sub1-B-4 (15 g, 28.1 mmol) and sub9 (6 g, 28.1 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in 23 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0117] Synthesis Example 1-10

Chemical formula

[0118] Under a nitrogen atmosphere, 1-B (15 g, 60.9 mmol) and Trz7 (28.6 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.6 g of sub1-B-5. (Yield 74%, MS: [M+H]+ = 636)

[0119] Under a nitrogen atmosphere, sub1-B-5 (15 g, 23.6 mmol) and sub5 (2.9 g, 23.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (6.5 g, 47.2 mmol) was dissolved in 20 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and then the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration, 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)

[0120] Synthesis Example 1-11

Chemical Structure

[0121] Under a nitrogen atmosphere, 1-B (15 g, 60.9 mmol) and Trz8 (21.8 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-B-6. (Yield 63%, MS: [M+H]+ = 524)

[0122] Under a nitrogen atmosphere, sub1-B-6 (15 g, 28.6 mmol) and sub10 (4.9 g, 28.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (7.9 g, 57.3 mmol) was dissolved in 24 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0123] Synthesis Example 1-12

Chemical formula

[0124] Under a nitrogen atmosphere, 1-C (15 g, 60.9 mmol) and Trz3 (19.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.6 g of sub1-C-1. (Yield 60%, MS: [M+H]+ = 484)

[0125] Under a nitrogen atmosphere, sub1-C-1 (15 g, 31 mmol) and sub10 (5.3 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. 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)

[0126] Synthesis Example 1-13 [Chemical formula]

[0127] Under a nitrogen atmosphere, 1-C (15 g, 60.9 mmol) and Trz9 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-C-2. (Yield 69%, MS: [M+H]+ = 560

[0128] Under a nitrogen atmosphere, sub1-C-2 (15 g, 26.8 mmol) and sub10 (4.6 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0129] Synthesis Example 1-14

Chemical Structure

[0130] Under a nitrogen atmosphere, 1-C (15 g, 60.9 mmol) and Trz10 (20.9 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.5 g of sub1-C-3. (Yield 66%, MS: [M+H]+ = 510)

[0131] Under a nitrogen atmosphere, sub1-C-3 (15 g, 29.4 mmol) and sub11 (7.3 g, 29.4 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (8.1 g, 58.8 mmol) was dissolved in 24 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. 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)

[0132] Synthesis Example 1-15

Chemical Structure

[0133] Under a nitrogen atmosphere, 1-C (15 g, 60.9 mmol) and Trz2 (16.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-C-4. (Yield 71%, MS: [M+H]+ = 434)

[0134] Under a nitrogen atmosphere, sub1-C-4 (15 g, 37.1 mmol) and sub12 (9.7 g, 37.1 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (10.3 g, 74.3 mmol) was dissolved in 31 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0135] Synthesis Example 1-16

Chemical formula

[0136] Under a nitrogen atmosphere, sub1-C- 2(15 g, 26.8 mmol) and sub13 (7.4 g, 26.8 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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, stirred, 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)

[0137] Synthesis Example 1-17

Chemical formula

[0138] Under a nitrogen atmosphere, sub1-C-4 (15 g, 34.6 mmol) and sub14 (7.7 g, 34.6 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.3 g of Compound 1-17. (Yield 62%, MS: [M+H]+ = 576)

[0139] Synthesis Example 1-18

Chemical formula

[0140] Under a nitrogen atmosphere, sub1-C-1 (15 g, 31 mmol) and sub9 (6.6 g, 31 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0141] Synthesis Example 1-19

Chemical formula

[0142] Under a nitrogen atmosphere, Chemical formula 1-C (15 g, 60.9 mmol) and Trz11 (22.4 g, 60.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-C-5. (Yield 69%, MS: [M+H]+ = 534)

[0143] Under a nitrogen atmosphere, sub1-C-5 (15 g, 28.1 mmol) and sub15 (6 g, 28.1 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in 23 ml of water and added, followed by thorough stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. 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)

[0144] Synthesis Example 1-20

Chemical formula

[0145] Under a nitrogen atmosphere, Chemical formula 1-C (15 g, 60.9 mmol) and Trz12 (21.8 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by thorough stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21 g of sub1-C-6. (Yield 66%, MS: [M+H]+ = 524)

[0146] Under a nitrogen atmosphere, sub1-C-6 (15 g, 28.6 mmol) and sub10 (4.9 g, 28.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0147] Synthesis Example 1-21

Chemical formula

[0148] Under a nitrogen atmosphere, chemical formula 1-C (15 g, 60.9 mmol) and Trz13 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-C-7. (Yield 77%, MS: [M+H]+ = 560)

[0149] Under a nitrogen atmosphere, sub1-C-7 (15 g, 26.8 mmol) and sub5 (3.3 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0150] Synthesis Example 1-22

Chemical formula

[0151] Under a nitrogen atmosphere, Chemical formula 1-D (15 g, 60.9 mmol) and Trz14 (19.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-1. (Yield 67%, MS: [M+H]+ = 586)

[0152] Under a nitrogen atmosphere, sub1-D-1 (15 g, 25.6 mmol) and sub5 (3.1 g, 25.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in 32 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0153] Synthesis Example 1-23

Chemical formula

[0154] Under a nitrogen atmosphere, Chemical formula 1-D (15 g, 60.9 mmol) and Trz2 (16.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-2. (Yield 76%, MS: [M+H]+ = 434)

[0155] Under a nitrogen atmosphere, sub1-D-2 (15 g, 34.6 mmol) and sub16 (9.1 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0156] Synthesis Example 1-24

Chemical formula

[0157] Under a nitrogen atmosphere, Chemical formula 1-D (15 g, 60.9 mmol) and Trz10 (20.9 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-3. (Yield 67%, MS: [M+H]+ = 510)

[0158] Under a nitrogen atmosphere, sub1-D-3 (15 g, 29.4 mmol) and sub17 (7.7 g, 29.4 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0159] Synthesis Example 1-25

Chemical formula

[0160] Under a nitrogen atmosphere, Chemical formula 1-D (15 g, 60.9 mmol) and Trz15 (21.8 g, 60.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-4. (Yield 67%, MS: [M+H]+ = 524)

[0161] Under a nitrogen atmosphere, sub1-D-4 (15 g, 28.6 mmol) and sub10 (4.9 g, 28.6 mmol) were placed in 300 ml of THF 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 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0162] Synthesis Example 1-26

Chemical formula

[0163] Under a nitrogen atmosphere, sub1-D-3 (15 g, 29.4 mmol) and sub18 (6.2 g, 29.4 mmol) were placed in 300 ml of THF 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 reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0164] Synthesis Example 1-27

Chemical formula

[0165] Under a nitrogen atmosphere, 1-D (15 g, 60.9 mmol) and Trz16 (27 g, 60.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-5. (Yield 73%, MS: [M+H]+ = 610)

[0166] Under a nitrogen atmosphere, sub1-D-5 (15 g, 24.6 mmol) and sub9 (5.2 g, 24.6 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0167] Synthesis Example 1-28

Chemical Formula

[0168] Under a nitrogen atmosphere, Chemical Formula 1-D (15 g, 60.9 mmol) and Trz13 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-6. (Yield 61%, MS: [M+H]+ = 560)

[0169] Under a nitrogen atmosphere, sub1-D-6 (15 g, 26.8 mmol) and sub10 (4.6 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0170] Synthesis Example 1-29

Chemical Formula

[0171] Under a nitrogen atmosphere, 1-E (15 g, 60.9 mmol) and Trz2 (16.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-1. (Yield 65%, MS: [M+H]+ = 434)

[0172] Under a nitrogen atmosphere, sub1-E-1 (15 g, 34.6 mmol) and sub2 (9.4 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0173] Synthesis Example 1-30

Chemical Structure

[0174] Under a nitrogen atmosphere, 1-E (15 g, 60.9 mmol) and Trz9 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-2. (Yield 79%, MS: [M+H]+ = 560)

[0175] Under a nitrogen atmosphere, sub1-E-2 (15 g, 26.8 mmol) and sub19 (7 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0176] Synthesis Example 1-31

Chemical Structure

[0177] Under a nitrogen atmosphere, 1-E (15 g, 60.9 mmol) and Trz17 (22.4 g, 60.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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, stirred, 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 sub1-E-3. (Yield 78%, MS: [M+H]+ = 534)

[0178] Under a nitrogen atmosphere, sub1-E-3 (15 g, 28.1 mmol) and sub2 0 (7.8 g, 28.1 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (11.6 g, 84.3 mmol) was dissolved in 35 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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, stirred, 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)

[0179] Synthesis Example 1-32

Chemical formula

[0180] Under a nitrogen atmosphere, sub1-E-1 (15 g, 34.6 mmol) and sub21 (7.7 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0181] Synthesis Example 1-33

Chemical formula

[0182] Under a nitrogen atmosphere, Chemical formula 1-E (15 g, 60.9 mmol) and Trz15 (21.8 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-4. (Yield 80%, MS: [M+H]+ = 524)

[0183] Under a nitrogen atmosphere, sub1-E-4 (15 g, 28.6 mmol) and sub10 (4.9 g, 28.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0184] Synthesis Example 1-34

Chemical Structure

[0185] Under a nitrogen atmosphere, Chemical Formula 1-E (15 g, 60.9 mmol) and Trz3 (19.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-5. (Yield 60%, MS: [M+H]+ = 484)

[0186] Under a nitrogen atmosphere, sub1-E-5 (15 g, 31 mmol) and sub9 (6.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0187] Synthesis Example 1-35

Chemical formula

[0188] Under a nitrogen atmosphere, Chemical formula 1-E (15 g, 60.9 mmol) and Trz10 (20.9 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-6. (Yield 70%, MS: [M+H]+ = 510)

[0189] Under a nitrogen atmosphere, sub1-E-6 (15 g, 29.4 mmol) and sub22 (7.7 g, 29.4 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0190] Synthesis Example 1-36

Chemical formula

[0191] Under a nitrogen atmosphere, sub1-E-5 (15 g, 31 mmol) and sub23 (8.1 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0192] Synthesis Example 1-37

Chemical formula

[0193] Under a nitrogen atmosphere, sub1-E-5 (15 g, 31 mmol) and sub10 (5.3 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0194] Synthesis Example 1-38

Chemical Formula

[0195] Under a nitrogen atmosphere, Chemical Formula 1-E (15 g, 60.9 mmol) and Trz18 (27 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-7. (Yield 65%, MS: [M+H]+ = 610)

[0196] Under a nitrogen atmosphere, sub1-E-7 (15 g, 24.6 mmol) and sub5 (3 g, 24.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0197] Synthesis Example 1-39

Chemical formula

[0198] Under a nitrogen atmosphere, Chemical formula 1-E (15 g, 60.9 mmol) and Trz13 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-8. (Yield 77%, MS: [M+H]+ = 560)

[0199] Under a nitrogen atmosphere, sub1-E-8 (15 g, 26.8 mmol) and sub5 (3.3 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0200] Synthesis Example 1-40

Chemical formula

[0201] Under a nitrogen atmosphere, chemical formula 1-F (15 g, 60.9 mmol) and Trz2 (16.3 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-F-1. (Yield 73%, MS: [M+H]+ = 434)

[0202] Under a nitrogen atmosphere sub1-F-1 (15 g, 34.6 mmol) and sub6 (8.5 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, followed by thorough stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0203] Synthesis Example 1-41

Chemical Formula

[0204] Under a nitrogen atmosphere, chemical formula 1-F (15 g, 60.9 mmol) and Trz10 (20.9 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by thorough stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-F-2. (Yield 68%, MS: [M+H]+ = 510)

[0205] Under a nitrogen atmosphere, sub1-F-2 (15 g, 29.4 mmol) and sub1 (5.8 g, 29.4 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0206] Synthesis Example 1-42

Chemical formula

[0207] Under a nitrogen atmosphere, Trz7 (15 g, 31.9 mmol) and sub9 (6.8 g, 31.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.2 g of compound 1-42. (Yield 79%, MS: [M+H]+ = 602)

[0208] Synthesis Example 1-43

Chemical formula

[0209] Under a nitrogen atmosphere, Trz16 (15 g, 33.8 mmol) and sub9 (7.2 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 1-43. (Yield 77%, MS: [M+H]+ = 576)

[0210] Synthesis Example 1-44

Chemical formula

[0211] Under a nitrogen atmosphere, Trz4 (15 g, 33.8 mmol) and sub9 (7.2 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of Compound 1-44. (Yield 73%, MS: [M+H]+ = 576)

[0212] Synthesis Example 1-45 [Chemistry]

[0213] Under a nitrogen atmosphere, Trz1 (15 g, 35.7 mmol) and sub9 (7.6 g, 35.7 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.8 g, 107.2 mmol) was dissolved in 44 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0214] Synthesis Example 1-46 [Chemistry]

[0215] Under a nitrogen atmosphere, Trz19 (15 g, 33.8 mmol) and sub9 (7.2 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 7 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.6 g of Compound 1-46. (Yield 70%, MS: [M+H]+ = 576)

[0216] Synthesis Examples 1 - 47

Chem.

[0217] Under a nitrogen atmosphere, Trz20 (15 g, 35.9 mmol) and sub9 (7.6 g, 35.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.9 g, 107.7 mmol) was dissolved in 45 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0218] Synthesis Example 1 - 48

Chem.

[0219] Under a nitrogen atmosphere, Trz3 (15 g, 47.2 mmol) and sub24 (9.7 g, 47.2 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in 59 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-1. (Yield 62%, MS: [M+H]+ = 444)

[0220] Under a nitrogen atmosphere, sub1-G-1 (15 g, 33.8 mmol) and sub9 (7.2 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0221] Synthesis Example 1-49 [Chemical Formula]

[0222] Under a nitrogen atmosphere Trz15(15 g, 41.9 mmol) and sub25 (8.7 g, 41.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-2. (Yield 62%, MS: [M+H]+ = 484)

[0223] Under a nitrogen atmosphere, sub1-G-2 (15 g, 31 mmol) and sub9 (6.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0224] Synthesis Example 1-50

Chemical Structure

[0225] Under a nitrogen atmosphere, Trz21 (15 g, 36.8 mmol) and sub26 (5.8 g, 36.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-3. (Yield 72%, MS: [M+H]+ = 484)

[0226] Under a nitrogen atmosphere, sub1-G-3 (15 g, 31 mmol) and sub9 (6.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0227] Synthesis Example 1-51 [Chemical Formula]

[0228] Under a nitrogen atmosphere, Trz16 (15 g, 33.8 mmol) and sub27 (5.3 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-4. (Yield 76%, MS: [M+H]+ = 520)

[0229] Under a nitrogen atmosphere, sub1-G-4 (15 g, 28.8 mmol) and sub9 (6.1 g, 28.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0230] Synthesis Example 1-52

Chemical Structure

[0231] Under a nitrogen atmosphere, Trz22 (15 g, 36.8 mmol) and sub28 (5.8 g, 36.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-5. (Yield 72%, MS: [M+H]+ = 484)

[0232] Under a nitrogen atmosphere, sub1-G-5 (15 g, 31 mmol) and sub9 (6.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0233] Synthesis Example 1-53

Chemical formula

[0234] Under a nitrogen atmosphere, Trz23 (15 g, 34.6 mmol) and sub27 (5.4 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-6. (Yield 64%, MS: [M+H]+ = 510)

[0235] Under a nitrogen atmosphere, sub1-G- 6 (15 g, 31 mmol) and sub9 (6.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0236] Synthesis Example 1-54

Chemical formula

[0237] Under a nitrogen atmosphere, sub1-G-1 (15 g, 33.8 mmol) and Chemical Formula 1-E (8.3 g, 33.8 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-9. (Yield 70%, MS: [M+H]+ = 610)

[0238] Under a nitrogen atmosphere, sub1-E-9 (15 g, 24.6 mmol) and sub5 (3 g, 24.6 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0239] Synthesis Example 1-55

Chemical Formula

[0240] Under a nitrogen atmosphere, Trz2 (15 g, 56 mmol) and sub24 (11.6 g, 56 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in 70 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-7. (Yield 71%, MS: [M+H]+ = 394)

[0241] Under a nitrogen atmosphere, sub1-G-7 (15 g, 38.1 mmol) and Chemical Formula 1-B (9.4 g, 38.1 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-B-7. (Yield 65%, MS: [M+H]+ = 560)

[0242] Under a nitrogen atmosphere, sub1-B-7 (15 g, 26.8 mmol) and sub5 (3.3 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water and added, followed by thorough stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, 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 stirred, and then filtered. 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)

[0243] Synthesis Example 1-56

Chemical formula

[0244] Under a nitrogen atmosphere, Trz24 (15 g, 40.1 mmol) and sub25 (9.1 g, 44.1 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.6 g, 120.3 mmol) was dissolved in 50 ml of water and added, followed by thorough stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of sub1-G-8. (Yield 69%, MS: [M+H]+ = 501)

[0245] Under a nitrogen atmosphere, sub1-G-8 (13 g, 26 mmol) and sub9 (6.1 g, 29 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (10.8 g, 78 mmol) was dissolved in 40 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 1-56. (Yield 73%, MS: [M+H]+ = 632)

[0246] Synthesis Example 1-57

Chemical Structure

[0247] Under a nitrogen atmosphere, Trz25 (15 g, 41.9 mmol) and sub24 (8.7 g, 41.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-9. (Yield 61%, MS: [M+H]+ = 484)

[0248] Under a nitrogen atmosphere, sub1-G-9 (15 g, 31 mmol) and Chemical Formula 1-F (7.6 g, 31 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-F-3. (Yield 62%, MS: [M+H]+ = 650)

[0249] Under a nitrogen atmosphere, sub1-F-3 (15 g, 23.1 mmol) and sub5 (2.8 g, 23.1 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in 29 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0250] Synthesis Example 1-58

Chemical Formula

[0251] Under a nitrogen atmosphere, Trz26 (15 g, 33.8 mmol) and sub26 (5.3 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-10. (Yield 60%, MS: [M+H]+ = 520)

[0252] Under a nitrogen atmosphere, sub1-G-10 (15 g, 28.8 mmol) and Chemical Formula 1-D (7.1 g, 28.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-7. (Yield 76%, MS: [M+H]+ = 687)

[0253] Under a nitrogen atmosphere, sub1-D-7 (15 g, 21.9 mmol) and sub5 (2.7 g, 21.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (9.1 g, 65.6 mmol) was dissolved in 27 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0254] Synthesis Example 1-59

Chemical formula

[0255] Under a nitrogen atmosphere, Trz15 (15 g, 41.9 mmol) and sub24 (8.7 g, 41.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-11. (Yield 61%, MS: [M+H]+ = 484)

[0256] Under a nitrogen atmosphere, sub1-G-11 (12.4 g, 25.6 mmol) and Chemical Formula 1-F (6.9 g, 28.2 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (11 g, 76.8 mmol) was dissolved in 36 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-F-4. (Yield 78%, MS: [M+H]+ = 651)

[0257] Under a nitrogen atmosphere, sub1-F-4 (13 g, 19.9 mmol) and sub5 (2.7 g, 21.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (8.3 g, 59.9 mmol) was dissolved in 29 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.2 g of Compound 1-59. (Yield 73%, MS: [M+H]+ = 692)

[0258] Synthesis Example 1-60

Chemical Formula

[0259] Under a nitrogen atmosphere, Trz12 (15 g, 41.9 mmol) and sub28 (6.6 g, 41.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-G-12. (Yield 61%, MS: [M+H]+ = 434)

[0260] Under a nitrogen atmosphere, sub1-G-12 (15 g, 34.6 mmol) and Chemical Formula 1-D (8.5 g, 34.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-8. (Yield 79%, MS: [M+H]+ = 500)

[0261] Under a nitrogen atmosphere, sub1-D-8 (15 g, 25 mmol) and sub10 (4.3 g, 25 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (10.4 g, 75 mmol) was dissolved in 31 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0262] Synthesis Example 1-61

Chemical formula

[0263] Under a nitrogen atmosphere, Trz27 (15 g, 31.9 mmol) and sub9 (6.8 g, 31.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10 g of compound 1-61. (Yield 52%, MS: [M+H]+ = 602)

[0264] Synthesis Example 1-62

Chemical formula

[0265] Under a nitrogen atmosphere, Trz28 (15 g, 33.8 mmol) and sub9 (7.2 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.2 g of Compound 1-62. (Yield 63%, MS: [M+H]+ = 576)

[0266] Synthesis Example 1-63

Chemical formula

[0267] Under a nitrogen atmosphere, Trz29 (15 g, 31.9 mmol) and sub9 (6.8 g, 31.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7 g of Compound 1-63. (Yield 66%, MS: [M+H]+ = 602)

[0268] Synthesis Example 1-64

Chemical formula

[0269] Under a nitrogen atmosphere, Trz30 (15 g, 31.9 mmol) and sub9 (6.8 g, 31.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (13.2 g, 95.8 mmol) was dissolved in 40 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.2 g of compound 1-64. (Yield 69%, MS: [M+H]+ = 602)

[0270] Synthesis Example 1-65

Chemical formula

[0271] Under a nitrogen atmosphere, Trz31 (15 g, 33.8 mmol) and sub9 (7.2 g, 33.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of compound 1-65. (Yield 75%, MS: [M+H]+ = 576)

[0272] Synthesis Example 1-66

Chem.

[0273] Under a nitrogen atmosphere, 1-B (15 g, 60.9 mmol) and Trz30 (28.6 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by sufficient stirring. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.3 g of sub1-B-7. (Yield 50%, MS: [M+H]+ = 636)

[0274] Under a nitrogen atmosphere, sub1-B-7 (15 g, 23.6 mmol) and sub5 (2.9 g, 23.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (9.8 g, 70.7 mmol) was dissolved in 29 ml of water and added, followed by sufficient stirring. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration, 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)

[0275] Synthesis Example 1-67

Chem.

[0276] Under a nitrogen atmosphere, 1-C (15 g, 60.9 mmol) and Trz32 (25.6 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.9 g of sub1-C-8. (Yield 70%, MS: [M+H]+ = 586)

[0277] Under a nitrogen atmosphere, sub1-C-8 (15 g, 25.6 mmol) and sub5 (3.1 g, 25.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in 32 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration. 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)

[0278] Synthesis Example 1-68

Chemical formula

[0279] Under a nitrogen atmosphere, Chemical Formula 1-D (15 g, 60.9 mmol) and Trz33 (27 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-D-7. (Yield 80%, MS: [M+H]+ = 610)

[0280] Under a nitrogen atmosphere, sub1-D-7 (15 g, 24.6 mmol) and sub5 (3 g, 24.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0281] Synthesis Example 1-69

Chemical Structure

[0282] Under a nitrogen atmosphere, 1-E (15 g, 60.9 mmol) and Trz34 (24 g, 60.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 sub1-E-9. (Yield 64%, MS: [M+H]+ = 560)

[0283] Under a nitrogen atmosphere, sub1-E-9 (15 g, 26.8 mmol) and sub5 (3.3 g, 26.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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)

[0284] <Production Example: Production of the Core of the Compound of Chemical Formula 2> (Synthesis Schemes of Production Examples 1 to 4)

Chemical Structure

[0285] Production Example 1: Synthesis of Chemical Formula AA [Chemistry]

[0286] Under a nitrogen atmosphere, 2-amino-5-bromo-4-fluorophenol (15 g, 72.8 mmol) and (3-chloro-2-hydroxyphenyl)boronic acid (12.6 g, 72.8 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (30.2 g, 218.4 mmol) was dissolved in 91 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 chemical formula AA_P1. (Yield 72%, MS: [M+H]+ = 254)

[0287] Under a nitrogen atmosphere, chemical formula AA_P1 (15 g, 59.1 mmol) and potassium carbonate (24.5 g, 177.4 mmol) were placed in 150 ml of DMF and stirred and refluxed.

[0288] After reacting for 9 hours, it was cooled to room temperature and the organic solvent was distilled under reduced pressure. This was further dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.6 g of chemical formula AA_P2. (Yield 70%, MS: [M+H]+ = 234)

[0289] Under a nitrogen atmosphere, chemical formula AA_P2 (15 g, 64.2 mmol), carbon disulfide (5.9 g, 77 mmol), and potassium hydroxide (4.3 g, 77 mmol) were placed in 150 ml of EtOH and stirred and refluxed.

[0290] After reacting for 12 hours, it was cooled to room temperature and the organic solvent was distilled off under reduced pressure. This was further dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled off under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.8 g of chemical formula AA_P3. (Yield 70%, MS: [M+H]+ = 242)

[0291] Under a nitrogen atmosphere, chemical formula AA_P3 (15 g, 62.2 mmol) and phosphorus pentachloride (15.5 g, 74.6 mmol) were placed in 150 ml of toluene and stirred and refluxed. After reacting for 12 hours, it was cooled to room temperature and the organic solvent was distilled off under reduced pressure. This was further dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled off under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.6 g of chemical formula AA. (Yield 79%, MS: [M+H]+ = 278)

[0292] Production Example 2: Synthesis of Chemical Formula AB

Chemical formula

[0293] Chemical formula AB was produced in the same manner as in Production Example 1, except that (4-chloro-2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0294] Production Example 3: Synthesis of Chemical Formula AC

Chemical formula

[0295] Compound AC was produced in the same manner as in Production Example 1, except that (5-chloro-2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0296] Production Example 4: Synthesis of Chemical Formula AD

Chemical Formula

[0297] Compound AD was produced in the same manner as in Production Example 1, except that (2-chloro-6-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0298] (Synthesis Schemes of Production Examples 5-6)

Chemical Formula

[0299] Production Example 5: Synthesis of Chemical Formula AE

Chemical Formula

[0300] Compound AE was produced in the same manner as in Production Example 1, except that 2-amino-5-bromo-3-chloro-4-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol and (2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0301] Production Example 6: Synthesis of Chemical Formula AF

Chemical Formula

[0302] Compound AF was produced in the same manner as in Production Example 1, except that 6-amino-3-bromo-2-chloro-4-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol and (2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0303] Production Example 7: Synthesis of Chemical Formula AG

Chemical Formula

[0304] Compound AG was produced in the same manner as in Production Example 1, except that (2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0305] (Synthesis Schemes of Production Examples 8 to 11)

Chemical Formula

[0306] Production Example 8: Synthesis of Chemical Formula BA

Chemical Formula

[0307] Compound BA was produced in the same manner as in Production Example 1, except that 2-amino-4-bromo-5-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol.

[0308] Production Example 9: Synthesis of Chemical Formula BB

Chemical Formula

[0309] Compound BB was produced in the same manner as in Production Example 1, except that 2-amino-4-bromo-5-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol, and (4-chloro-2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0310] Production Example 10: Synthesis of Chemical Formula BC

Chemical formula

[0311] Compound BC was produced in the same manner as in Production Example 1, except that 2-amino-4-bromo-5-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol, and (5-chloro-2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0312] Production Example 11: Synthesis of Chemical Formula BD

Chemical formula

[0313] Compound BD was produced in the same manner as in Production Example 1, except that 2-amino-4-bromo-5-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol, and (2-chloro-6-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0314] (Synthesis schemes for Production Examples 12 to 13) [Chemical formula]

[0315] Production Example 12: Synthesis of Chemical Formula BE [Chemical formula]

[0316] Chemical Formula BE was produced in the same manner as in Production Example 1, except that 6-amino-4-bromo-2-chloro-3-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol, and (2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0317] Production Example 13: Synthesis of Chemical Formula BF [Chemical formula]

[0318] Chemical Formula BF was produced in the same manner as in Production Example 1, except that 2-amino-4-bromo-3-chloro-5-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol, and (2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0319] Production Example 14: Synthesis of Chemical Formula BG [Chemical formula]

[0320] Compound BG was produced in the same manner as in Production Example 1, except that 2-amino-4-bromo-5-fluorophenol was used instead of 2-amino-5-bromo-4-fluorophenol, and (2-hydroxyphenyl)boronic acid was used instead of (3-chloro-2-hydroxyphenyl)boronic acid.

[0321] <Synthesis Example 2: Production of the Compound of Chemical Formula 2> Synthesis Example 2-1

Chem.

[0322] Under a nitrogen atmosphere, subAA-3 (10 g, 31.3 mmol), amine1 (13.2 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.8 g of Compound 2-1. (Yield 58%, MS: [M+H]+ = 705)

[0323] Synthesis Example 2-2

Chem.

[0324] Under a nitrogen atmosphere, subAA-3 (10 g, 31.3 mmol), amine2 (10.8 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.6 g of compound 2-2. (Yield 54%, MS: [M+H]+ = 629)

[0325] Synthesis Example 2-3

Chemical formula

[0326] Under a nitrogen atmosphere, subAA-3 (10 g, 31.3 mmol), amine3 (11 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.9 g of compound 2-3. (Yield 65%, MS: [M+H]+ = 635)

[0327] Synthesis Example 2-4

Chemical formula

[0328] Under a nitrogen atmosphere, subAA-3 (15 g, 46.9 mmol) and amine4 (20.7 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24 g of compound 2-4. (Yield 74%, MS: [M+H]+ = 691)

[0329] Synthesis Example 2-5

Chemical formula

[0330] Under a nitrogen atmosphere, chemical formula AA (15 g, 53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g, 53.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and added, and after sufficient stirring, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.7 g of subAA-4. (Yield 79%, MS: [M+H]+ = 370)

[0331] Under a nitrogen atmosphere, subAA-4 (15 g, 40.6 mmol) and amine5 (16.8 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.3 g of compound 2-5. (Yield 64%, MS: [M+H]+ = 705)

[0332] Synthesis Example 2-6

Chemical formula

[0333] Under a nitrogen atmosphere, subAB-1 (10 g, 31.3 mmol), amine6 (12.9 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15 g of compound 2-6. (Yield 69%, MS: [M+H]+ = 695)

[0334] Synthesis Example 2-7

Chemical formula

[0335] Under a nitrogen atmosphere, subAB-1 (10 g, 31.3 mmol), amine7 (10.9 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13 g of compound 2-7. (Yield 66%, MS: [M+H]+ = 633)

[0336] Synthesis Example 2-8

Chemical formula

[0337] Under a nitrogen atmosphere, subAB-1 (15 g, 46.9 mmol) and amine8 (24.9 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred well. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.5 g of compound 2-8. (Yield 76%, MS: [M+H]+ = 771)

[0338] Synthesis Example 2-9

Chemical formula

[0339] Under a nitrogen atmosphere, subAB-1 (15 g, 46.9 mmol) and amine9 (26.6 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) was added.

[0340] After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.1 g of compound 2-9. (Yield 69%, MS: [M+H]+ = 807)

[0341] Synthesis Example 2-10

Chemical formula

[0342] Under a nitrogen atmosphere, subAB-1 (15 g, 46.9 mmol) and amine10 (21.7 g, 49.3 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.3 g of compound 2-10. (Yield 51%, MS: [M+H]+ = 681)

[0343] Synthesis Example 2-11 [Chemical formula]

[0344] Under a nitrogen atmosphere, chemical formula AB (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.7 g, 53.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water, added, and stirred thoroughly. After that, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.9 g of subAB-3. (Yield 70%, MS: [M+H]+ = 396)

[0345] Under a nitrogen atmosphere, subAB-3 (10 g, 25.3 mmol), amine11 (6.2 g, 25.3 mmol), and sodium tert-butoxide (8 g, 37.9 mmol) were placed in 200 ml of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.9 g of Compound 2-11. (Yield 65%, MS: [M+H]+ = 605)

[0346] Synthesis Example 2-12 [Chemical formula]

[0347] Under a nitrogen atmosphere, AC with the chemical formula (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water, added, and stirred thoroughly. After that, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12 g of subAC-3. (Yield 70%, MS: [M+H]+ = 320)

[0348] Under a nitrogen atmosphere, subAC-3 (10 g, 31.3 mmol), amine12 (14 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.9 g of compound 2-12. (Yield 61%, MS: [M+H]+ = 731)

[0349] Synthesis Example 2-13

Chemical formula

[0350] Under a nitrogen atmosphere, subAC-3 (10 g, 31.3 mmol), amine13 (11.6 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4 g of compound 2-13. (Yield 51%, MS: [M+H]+ = 655)

[0351] Synthesis Example 2-14

Chemical formula

[0352] Under a nitrogen atmosphere, subAC-3 (10 g, 31.3 mmol), amine14 (11.3 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.7 g of compound 2-14. (Yield 68%, MS: [M+H]+ = 645)

[0353] Synthesis Example 2-15

Chemical formula

[0354] Under a nitrogen atmosphere, subAC-3 (15 g, 46.9 mmol) and amine15 (19.5 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.6 g of compound 2-15. (Yield 77%, MS: [M+H]+ = 655)

[0355] Synthesis Example 2-16

Chemical formula

[0356] Under a nitrogen atmosphere, subAC-3 (15 g, 46.9 mmol) and amine16 (20.7 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-16. (Yield 72%, MS: [M+H]+ = 681)

[0357] Synthesis Example 2-17

Chemical formula

[0358] Under a nitrogen atmosphere, subAC-3 (10 g, 31.3 mmol), amine17 (14 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13 g of compound 2-17. (Yield 57%, MS: [M+H]+ = 731)

[0359] Synthesis Example 2-18

Chemical Structure

[0360] Under a nitrogen atmosphere, chemical formula AC (15 g, 53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g, 53.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water, added, and stirred well. Then, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer 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, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7 g of subAC-4. (Yield 64%, MS: [M+H]+ = 370)

[0361] Under a nitrogen atmosphere, subAC-4 (10 g, 27 mmol), amine18 (8.7 g, 27 mmol), and sodium tert-butoxide (8.6 g, 40.6 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound 2-18. (Yield 53%, MS: [M+H]+ = 655)

[0362] Synthesis Example 2-19

Chemical formula

[0363] Under a nitrogen atmosphere, subAD-1 (10 g, 31.3 mmol), amine19 (13.2 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13 g of compound 2-19. (Yield 59%, MS: [M+H]+ = 705)

[0364] Synthesis Example 2-20

Chemical formula

[0365] Under a nitrogen atmosphere, subAD-1 (15 g, 40.6 mmol) and amine20 (23 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.9 g of compound 2-20. (Yield 64%, MS: [M+H]+ = 807)

[0366] Synthesis Example 2-21

Chemical formula

[0367] Under a nitrogen atmosphere, subAD-1 (10 g, 31.3 mmol), amine21 (12.8 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 2-21. (Yield 53%, MS: [M+H]+ = 694)

[0368] Synthesis Example 2-22

Chemical formula

[0369] Under a nitrogen atmosphere, subAD-1 (15 g, 40.6 mmol) and amine22 (18.5 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.4 g of compound 2-22. (Yield 69%, MS: [M+H]+ = 695)

[0370] Synthesis Example 2-23

Chemical formula

[0371] Under a nitrogen atmosphere, subAD-1 (15 g, 46.9 mmol) and amine23 (24.2 g, 49.3 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.3 g of compound 2-23. (Yield 68%, MS: [M+H]+ = 731)

[0372] Synthesis Example 2-24

Chem.

[0373] Under a nitrogen atmosphere, chemical formula AD (15 g, 53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g, 53.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and added, and after sufficient stirring, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.5 g of subAD-5. (Yield 68%, MS: [M+H]+ = 370)

[0374] Under a nitrogen atmosphere, subAD-5 (10 g, 27 mmol), amine24 (8 g, 27 mmol), and sodium tert-butoxide (8.6 g, 40.6 mmol) were placed in 200 ml of xylene and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2 g of compound 2-24. (Yield 54%, MS: [M+H]+ = 630)

[0375] Synthesis Example 2-25

Chem.

[0376] Under a nitrogen atmosphere, subAE-1 (10 g, 31.3 mmol), amine25 (13.2 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-25. (Yield 60%, MS: [M+H]+ = 705)

[0377] Synthesis Example 2-26

Chemical formula

[0378] Under a nitrogen atmosphere, subAE-1 (15 g, 46.9 mmol) and amine26 (25.4 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 11 hours of reaction, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 2-26. (Yield 64%, MS: [M+H]+ = 781)

[0379] Synthesis Example 2-27

Chemical formula

[0380] Under a nitrogen atmosphere, subAE-1 (15 g, 46.9 mmol) and amine27 (23.1 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-27. (Yield 65%, MS: [M+H]+ = 731)

[0381] Synthesis Example 2-28

Chemical formula

[0382] Under a nitrogen atmosphere, chemical formula AE (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.7 g, 53.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and added, and after sufficient stirring, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 subAE-4. (Yield 62%, MS: [M+H]+ = 396)

[0383] Under a nitrogen atmosphere, subAE-4 (10 g, 25.3 mmol), amine18 (8.1 g, 25.3 mmol), and sodium tert-butoxide (8 g, 37.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 2-28. (Yield 64%, MS: [M+H]+ = 681)

[0384] Synthesis Example 2-29

Chemical formula

[0385] Under a nitrogen atmosphere, subAF-1 (15 g, 46.9 mmol) and amine28 (20.7 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred well. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.1 g of compound 2-29. (Yield 65%, MS: [M+H]+ = 757)

[0386] Synthesis Example 2-30

Chemical formula

[0387] Under a nitrogen atmosphere, subBA-3 (15 g, 40.6 mmol) and amine29 (19.9 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound 2-30. (Yield 61%, MS: [M+H]+ = 731)

[0388] Synthesis Example 2-31

Chemical Structure

[0389] Under a nitrogen atmosphere, subBA-3 (15 g, 40.6 mmol) and amine30 (19.1 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.6 g of compound 2-31. (Yield 75%, MS: [M+H]+ = 711)

[0390] Synthesis Example 2-32 [Chemistry]

[0391] Under a nitrogen atmosphere, subBA-3 (15 g, 40.6 mmol) and amine31 (17.9 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.6 g of compound 2-32. (Yield 71%, MS: [M+H]+ = 681)

[0392] Synthesis Example 2-33 [Chemistry]

[0393] Under a nitrogen atmosphere, subBA-3 (15 g, 46.9 mmol) and amine32 (21.7 g, 49.3 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.5 g of compound 2-33. (Yield 58%, MS: [M+H]+ = 681)

[0394] Synthesis Example 2-34

Chem.

[0395] Under a nitrogen atmosphere, subBB-1 (10 g, 31.3 mmol), amine33 (11.6 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of Compound 2-34. (Yield 53%, MS: [M+H]+ = 655)

[0396] Synthesis Example 2-35

Chem.

[0397] Under a nitrogen atmosphere, subBB-1 (10 g, 31.3 mmol), amine34 (12.4 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of Compound 2-35. (Yield 63%, MS: [M+H]+ = 681)

[0398] Synthesis Example 2-36

Chem.

[0399] Under a nitrogen atmosphere, subBB-1 (15 g, 46.9 mmol) and amine35 (23.1 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25 g of Compound 2-36. (Yield 73%, MS: [M+H]+ = 731)

[0400] Synthesis Example 2-37

Chem.

[0401] Under a nitrogen atmosphere, subBB-1 (15 g, 46.9 mmol) and amine36 (24.3 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, followed by sufficient stirring. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.6 g of compound 2-37. (Yield 61%, MS: [M+H]+ = 757)

[0402] Synthesis Example 2-38

Chemical formula

[0403] Under a nitrogen atmosphere, chemical formula BC (15 g, 53.9 mmol) and phenylboronic acid (6.6 g, 53.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water and added, followed by sufficient stirring. After that, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 11 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated. Then, the organic layer was distilled. This was further dissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of subBC-3. (Yield 72%, MS: [M+H]+ = 320)

[0404] Under a nitrogen atmosphere, subBC-3 (10 g, 31.3 mmol), amine37 (12.9 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-38. (Yield 61%, MS: [M+H]+ = 695)

[0405] Synthesis Example 2-39

Chemical formula

[0406] Under a nitrogen atmosphere, subBC-3 (10 g, 31.3 mmol), amine38 (14 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.8 g of compound 2-39. (Yield 56%, MS: [M+H]+ = 731)

[0407] Synthesis Example 2-40

Chemical formula

[0408] Under a nitrogen atmosphere, subBC-3 (15 g, 46.9 mmol) and amine39 (19.5 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 2-40. (Yield 60%, MS: [M+H]+ = 655)

[0409] Synthesis Example 2-41

Chemical formula

[0410] Under a nitrogen atmosphere, subBC-3 (15 g, 46.9 mmol) and amine40 (18.5 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 2-41. (Yield 70%, MS: [M+H]+ = 635)

[0411] Synthesis Example 2-42

Chemical formula

[0412] Under a nitrogen atmosphere, BC with the chemical formula (15 g, 53.9 mmol) and [1,1'-biphenyl]-4-ylboronic acid (10.7 g, 53.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water, added, and stirred thoroughly. After that, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.8 g of subBC-4. (Yield 74%, MS: [M+H]+ = 396)

[0413] Under a nitrogen atmosphere, subBC-4 (10 g, 25.3 mmol), amine41 (10 g, 25.3 mmol), and sodium tert-butoxide (8 g, 37.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After the reaction ended after 2 hours, it was cooled to room temperature, the pressure was reduced, and the solvent was removed. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-42. (Yield 62%, MS: [M+H]+ = 757)

[0414] Synthesis Example 2-43

Chemical formula

[0415] Under a nitrogen atmosphere, subBD-1 (10 g, 31.3 mmol), amine42 (10.8 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-43. (Yield 60%, MS: [M+H]+ = 629)

[0416] Synthesis Example 2-44

Chemical formula

[0417] Under a nitrogen atmosphere, subBD-1 (10 g, 31.3 mmol), amine43 (11.6 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.7 g of compound 2-44. (Yield 67%, MS: [M+H]+ = 655)

[0418] Synthesis Example 2-45

Chemical formula

[0419] Under a nitrogen atmosphere, subBD-1 (10 g, 31.3 mmol), amine44 (11.6 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 2-45. (Yield 56%, MS: [M+H]+ = 655)

[0420] Synthesis Example 2-46

Chemical formula

[0421] Under a nitrogen atmosphere, subBD-1 (10 g, 31.3 mmol), amine45 (14 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.8 g of compound 2-46. (Yield 65%, MS: [M+H]+ = 731)

[0422] Synthesis Example 2-47

Chemical formula

[0423] Under a nitrogen atmosphere, subBD-1 (10 g, 31.3 mmol), amine46 (14 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain Compound 2-47 14.1 g. (Yield 64%, MS: [M+H]+ = 705)

[0424] Synthesis Example 2-48

Chemical formula

[0425] Under a nitrogen atmosphere, chemical formula BD (15 g, 53.9 mmol) and naphthalen-2-ylboronic acid (9.3 g, 53.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (22.4 g, 161.8 mmol) was dissolved in 67 ml of water, added, and stirred well. Then, Tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, 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 subBD-3. (Yield 69%, MS: [M+H]+ = 370)

[0426] Under a nitrogen atmosphere, subBD-3 (15 g, 40.6 mmol) and amine47 (18.5 g, 40.6 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 2-48. (Yield 72%, MS: [M+H]+ = 745)

[0427] Synthesis Example 2-49

Chemical Structure

[0428] Under a nitrogen atmosphere, subBE-1 (15 g, 46.9 mmol) and amine48 (22 g, 46.9 mmol) were placed in 300 ml of THF and stirred and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.6 g of compound 2-49. (Yield 80%, MS: [M+H]+ = 709)

[0429] Synthesis Example 2-50

Chemical Structure

[0430] Under a nitrogen atmosphere, subBE-1 (15 g, 46.9 mmol) and amine49 (22.6 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.3 g of compound 2-50. (Yield 69%, MS: [M+H]+ = 721)

[0431] Synthesis Example 2-51

Chemical formula

[0432] Under a nitrogen atmosphere, subBE-1 (15 g, 46.9 mmol) and amine50 (24.3 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred thoroughly. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.3 g of compound 2-51. (Yield 74%, MS: [M+H]+ = 757)

[0433] Synthesis Example 2-52

Chem.

[0434] Under a nitrogen atmosphere, subBE-2 (10 g, 27 mmol), amine41 (10.7 g, 27 mmol), and sodium tert-butoxide (8.6 g, 40.6 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of Compound 2-52. (Yield 60%, MS: [M+H]+ = 731)

[0435] Synthesis Example 2-53

Chem.

[0436] Under a nitrogen atmosphere, subBF-1 (15 g, 46.9 mmol) and amine52 (23.1 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water and added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.2 g of Compound 2-53. (Yield 62%, MS: [M+H]+ = 731)

[0437] Synthesis Example 2-54

Chem.

[0438] Under a nitrogen atmosphere, subBF-1 (10 g, 31.3 mmol), amine53 (9.2 g, 31.3 mmol), and sodium tert-butoxide (10 g, 46.9 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of Compound 2-54. (Yield 59%, MS: [M+H]+ = 579)

[0439] Synthesis Example 2-55

Chem.

[0440] Under a nitrogen atmosphere, subBF-1 (15 g, 46.9 mmol) and amine54 (26.6 g, 46.9 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (19.5 g, 140.7 mmol) was dissolved in 58 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.4 g of compound 2-55. (Yield 75%, MS: [M+H]+ = 807)

[0441] Synthesis Example 2-56

Chemical formula

[0442] Under a nitrogen atmosphere, subBF-2 (10 g, 27 mmol), amine55 (9.1 g, 27 mmol), and sodium tert-butoxide (8.6 g, 40.6 mmol) were placed in 200 ml of xylene, stirred, and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of compound 2-56. (Yield 59%, MS: [M+H]+ = 669)

[0443] Synthesis Example 2-57

Chemical formula

[0444] Under a nitrogen atmosphere, subBF-2 (15 g, 40.6 mmol) and amine56 (21 g, 40.6 mmol) were placed in 300 ml of THF, stirred, and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water, added, and stirred well. After that, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then 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 stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20 g of compound 2-57. (Yield 61%, MS: [M+H]+ = 807)

[0445] <Examples and Comparative Examples> Example 1 A glass substrate thinly coated with ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water in which a detergent was dissolved and washed ultrasonically. At this time, a product of Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered through a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes each. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning device. Also, after washing the substrate with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporation device.

[0446] On the thus-prepared ITO transparent electrode, the following HI-1 compound was formed as a hole injection layer with a thickness of 1150 Å, and the following A-1 compound was p-doped at a concentration of 1.5 wt%. The following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 800 Å. Subsequently, the following EB-1 compound was vacuum-deposited on the hole transport layer with a thickness of 150 Å to form an electron blocking layer. Subsequently, the following Compound 1-2, Compound 2-1, and Dp-7 compound were vacuum-deposited on the EB-1 deposited film at a weight ratio of 49:49:2 to form a red light-emitting layer with a thickness of 400 Å. The following HB-1 compound was vacuum-deposited on the light-emitting layer with a thickness of 30 Å to form a hole blocking layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited on the hole blocking layer at a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode. [Chemical formula]

[0447] In the above process, the deposition rate of the organic material was maintained at 0.4 - 0.7 Å / sec, the deposition rate of lithium fluoride for the negative electrode was 0.3 Å / sec, and that of aluminum was 2 Å / sec. The degree of vacuum during deposition was maintained at 2×10 -7 ~5×10 -6 torr to fabricate the organic light-emitting device.

[0448] Examples 2 to 190 An organic light-emitting device was manufactured in the same manner as in Example 1, except that in the organic light-emitting device of Example 1, the first host and the second host described in Table 1 were co-deposited at a ratio of 1:1 instead of Compound 1-2 and Compound 2-1.

[0449] Comparative Examples 1 to 120 An organic light-emitting device was fabricated in the same manner as in Example 1, except that the comparative compounds A-1 to A-12 described in Table 2 below were co-evaporated with the compound of Chemical Formula 2 described in Table 2 at a ratio of 1:1 on the first host, and the comparative compounds B-1 to B-20 described in Table 3 were co-evaporated with the compound of Chemical Formula 1 described in Table 3 at a ratio of 1:1 on the second host.

[0450] Comparative Examples 121 to 280 An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compound of Chemical Formula 1 described in Table 3 below was co-evaporated with the comparative compounds B-1 to B-20 described in Table 3 at a ratio of 1:1 on the first host, and the comparative compounds B-1 to B-20 described in Table 3 were co-evaporated with the compound of Chemical Formula 1 described in Table 3 at a ratio of 1:1 on the second host.

[0451] The comparative compounds A-1 to A-12 and B-1 to B-20 are as follows. [Chemical Formula] [Chemical Formula]

[0452] [Experimental Example] When current was applied to the organic light-emitting devices fabricated in Examples 1 to 190 and Comparative Examples 1 to 280, the voltage and efficiency were measured (at 15 mA / cm 2 reference), and the results are shown in Tables 1 to 3 below. The lifetime T95 was measured based on 7000 nit, and T95 means the time required for the initial lifetime to decrease to 95%.

[0453] [Table 1] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5]

Table 1-6

[0454] [Table 2]

Table 2-1

Table 2-2

Table 2-3

Table 2-4

[0455] [Table 3]

Table 3-1

Table 3-2

Table 3-3

Table 3-4

[0456] When current was applied to the organic light-emitting devices fabricated by Examples 1 to 190 and Comparative Examples 1 to 280, the results in Tables 1 to 3 were obtained. The red organic light-emitting device of Example 1 has a structure using Compound EB-1 in the electron blocking layer and Dp-7 as the dopant in the red light-emitting layer. Referring to Table 1, it can be confirmed that when the compounds of Chemical Formula 1 and Chemical Formula 2 of the present invention are co-evaporated and used in the red light-emitting layer, the driving voltage is low and the efficiency and lifetime are excellent.

[0457] On the one hand, as shown in Table 2, when A-1 to A-12 were co-evaporated with the compound of Chemical Formula 2 of the present invention and used in the red light-emitting layer, the driving voltage generally increased compared to the combination of the present invention, showing results of decreased efficiency and lifespan. Also, as shown in Table 3, when B-1 to B-20 were co-evaporated with the compound of Chemical Formula 1 of the present invention and used as the red light-emitting layer, the driving voltage increased and the efficiency and lifespan decreased as well.

[0458] From such results, it can be confirmed that the organic light-emitting device of the present invention exhibits excellent effects in terms of driving voltage, efficiency, and lifespan. This can be inferred to be because when the combination of compounds used in the comparative example is compared with the combination of the compound of Chemical Formula 1, which is the first host of the present invention, and the compound of Chemical Formula 2, which is the second host, the energy transfer to the red dopant in the red light-emitting layer becomes better.

[0459] Conclusively, it can be confirmed that when the compounds of Chemical Formula 1 and Chemical Formula 2 of the present invention are combined and co-evaporated and used as the host of the red light-emitting layer, there is a possibility of improving the driving voltage, luminous efficiency, and lifespan characteristics of the organic light-emitting device.

Explanation of Symbols

[0460] 1 Substrate 2 Anode 3 Light-emitting layer 4 Cathode 5 Hole injection layer 6 Hole transport layer 7 Electron transport layer 8 Electron injection layer 9 Electron blocking layer 10 Hole blocking layer 11 Electron injection and transport layer

Claims

1. A positive electrode; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, wherein the light-emitting layer contains a compound represented by the following Chemical Formula 1-1 and a compound represented by the following Chemical Formula 2: [Chemical Formula 1-1] 【Chemical 4】 In Chemical Formula 1-1, L is a single bond; or an unsubstituted arylene having 6 to 10 carbon atoms, Ar １ and Ar ２ each independently is an aryl having 6 to 14 carbon atoms which is substituted or unsubstituted with an unsubstituted aryl having 6 to 10 carbon atoms; or a heteroaryl having 12 carbon atoms containing any one selected from the group consisting of unsubstituted O and S, Ar ３ is hydrogen; aryl having 6 to 18 carbon atoms which is substituted or unsubstituted with aryl having 6 to 10 carbon atoms; or heteroaryl having 12 to 16 carbon atoms containing any one selected from the group consisting of unsubstituted O and S, D is deuterium, n is 0, [Chemical Formula 2] [Chemical 2] In Chemical Formula 2, A' １ is represented by the following chemical formula 2-a, [Chemical Formula 2-a] [Chemical Formula 3] In Chemical Formula 2-a, The dotted line is a part that fuses with an adjacent ring, Ar' １ is an unsubstituted aryl having 6 to 12 carbon atoms, L' is a single bond; or an unsubstituted arylene having 6 to 12 carbon atoms, Ar' ２ and Ar' ３ each independently is alkyl having 1 carbon atom, unsubstituted aryl having 6 to 18 carbon atoms, or aryl having 6 to 18 carbon atoms substituted or unsubstituted with heteroaryl having 12 carbon atoms containing 1 unsubstituted O, or heteroaryl having 12 carbon atoms containing any one heteroatom selected from the group consisting of N, O and S substituted or unsubstituted with unsubstituted aryl having 6 carbon atoms, D is deuterium, n' is 0.

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

3. Ar １ and Ar ２ each independently is phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; (naphthyl)naphthyl; dibenzofuranyl; or dibenzothiophenyl, the organic light-emitting device according to claim 1.

4. Ar ３ is hydrogen; phenyl; biphenylyl; terphenylyl; naphthyl; phenanthrenyl; (phenyl)naphthyl; (naphthyl)phenyl; fluoranthenyl; triphenylenyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthofuranyl; or benzonaphthothiophenyl, the organic light-emitting device according to claim 1.

5. The organic light-emitting device according to Claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of the following: 【Chemical Formula 5】 【Chemical Formula 6】 【Chemical Formula 7】 【Chemical Formula 8】 【Chemical Formula 9】 【Chemical Formula 10】 【Chemical 11】 【Chemical Formula 12】 【Chemical 13】 【Chemical Formula 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical 18】 【Chemical Formula 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemical Formula 24】 【Chemical Formula 25】 【Chemical 26】 【Chemical 27】 【Chemical Formula 28】 【Chemical 29】 【Chemical Formula 30】 【Chemical Formula 31】 【Chemical 32】 【Chemical 33】 【Chemical 34】 【Chemical 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 【Chemical Formula 40】 【Chemical 41】 【Chemical Formula 42】 【Chemical 43】 【Chemical 44】 【Chemical 45】 【Chemical 46】 【Chemical 47】 【Chemical 48】 【Chemical Formula 49】 【Chemical Formula 50】 【Chemical Formula 51】 【Chemical 52】 【Chemical 53】 【Chemical 54】 【Chemical Formula 55】 【Chemical 56】 【Chemical 57】 【Chemical Formula 58】 【Chemical 59】 【Chemical Formula 60】 【Chemical Formula 61】 【Chemical Formula 62】 【Chemical Formula 63】 【Chemical Formula 64】 【Chemical Formula 65】 【Chemical 66】 【Chemical 67】 【Chemical Formula 68】 【Chemical Formula 69】 【Chemical 70】 【Chemical 71】 【Chemical 72】 【Chemical 73】 【Chemical Formula 74】 【Chemical 75】 【Chemical 76】 【Chemical 77】 【Chemical 78】 【Chemical Formula 79】 【Chemical 80】 【Chemical 81】 【Chemical 82】 【Chemical 83】 【Chemical 84】 【Chemical 85】 【Chemical 86】 【Chemical 87】 【Chemical 88】 【Chemical 89】 【Chemical Formula 90】 【Chemical Formula 91】 【Chemical Formula 92】 【Chemical Formula 93】 【Chemical Formula 94】 【Chemical Formula 95】 【Chemical Formula 96】 【Chemical 97】 【Chemical Formula 98】 【Chemical Formula 99】 【Chemical 100】 【Chemical 101】 【Chemical 102】 【Chemical Formula 103】 【Chemical Formula 104】 【Chemical 105】 【Chemical 106】 【Chemical 107】 【Chemical 108】 【Chemical 109】 【Chemical 110】 【Chemical 111】 。

6. The organic light-emitting device according to Claim 1, wherein Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2: [Chemical Formula 2-1] 【Chemical 112】 [Chemical Formula 2-2] 【Chemical 113】 In Chemical Formulas 2-1 and 2-2, L', Ar' １ ~Ar' ３ , D, and n' are as defined in claim 1.

7. The organic light-emitting device according to Claim 1, wherein L' is a single bond; phenylene; or biphenyldiyl.

8. Ar' １ The organic light-emitting device according to claim 1, wherein Ar' is phenyl.

9. Ar' ２ and Ar' ３ each independently is phenyl; biphenylyl; terphenylyl; naphthyl; (naphthyl)phenyl; (phenyl)naphthyl; (naphthyl)biphenylyl; (naphthyl)naphthyl; [(phenyl)naphthyl]phenyl; dibenzofuranyl; dibenzothiophenyl; (dibenzofuranyl)phenyl; (dibenzothiophenyl)phenyl; phenanthrenyl; (phenanthrenyl)phenyl; 9,9-dimethylfluorenyl; or 9-phenylcarbazolyl, the organic light-emitting device according to claim 1.

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 the following: 【Chemical 114】 【Chemical 115】 【Chemical 116】 【Chemical 117】 【Chemical 118】 【Chemical 119】 【Chemical 120】 【Chemical 121】 【Chemical 122】 【Chemical 123】 【Chemical 124】 【Chemical 125】 【Chemical 126】 【Chemical 127】 【Chemical 128】 【Chemical 129】 【Chemical 130】 【Chemical 131】 【Chemical 132】 【Chemical 133】 【Chemical 134】 【Chemical 135】 【Chemical 136】 【Chemical 137】 【Chemical 138】 【Chemical 139】 【Chemical 140】 【Chemical 141】 【Chemical 142】 【Chemical 143】 【Chemical 144】 【Chemical 145】 【Chemical 146】 【Chemical 147】 【Chemical 148】 【Chemical 149】 【Chemical 150】 【Chemical 151】 【Chemical 152】 【Chemical 153】 【Chemical 154】 【Chemical 155】 【Chemical 156】 【Chemical 157】 【Chemical 158】 【Chemical 159】 【Chemical 160】 【Chemical Formula 161】 【Chemical 162】 【Chemical 163】 【Chemical 164】 【Chemical 165】 【Chemical 166】 【Chemical 167】 【Chemical 168】 【Chemical 169】 【Chemical 170】 【Chemical 171】 【Chemical 172】 【Chemical 173】 【Chemical 174】 【Chemical 175】 【Chemical 176】 【Chemical 177】 【Chemical 178】 【Chemical 179】 【Chemical 180】 【Chemical 181】 【Chemical 182】 【Chemical 183】 【Chemical 184】 【Chemical 185】 【Chemical 186】 【Chemical 187】 【Chemical 188】 【Chemical 189】 【Chemical 190】 【Chemical Formula 191】 【Chemical Formula 192】 【Chemical 193】 【Chemical Formula 194】 【Chemical Formula 195】 【Chemical 196】 【Chemical 197】 【Chemical 198】 【Chemical 199】 【Chemical 200】 【Chemical 201】 【Chemical 202】 【Chemical 203】 【Chemical 204】 【Chemical 205】 【Chemical 206】 【Chemical 207】 【Chemical formula 208】 【Chemical 209】 【Chemical 210】 【Chemical 211】 【Chemical 212】 【Chemical 213】 【Chemical 214】 【Chemical 215】 【Chemical 216】 【Chemical 217】 【Chemical 218】 【Chemical 219】 【Chemical 220】 【Chemical 221】 【Chemical 222】 【Chemical 223】 【Chemical 224】 【Chemical 225】 【Chemical 226】 【Chemical 227】 【Chemical 228】 【Chemical 229】 。

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