Organic light-emitting devices

Abstract

The present disclosure relates to organic light emitting devices with improved driving voltage, efficiency, and lifetime.

Description

Technical Field

[0001] The present disclosure relates to organic light emitting devices with improved driving voltage, efficiency, and lifetime. Background Art

[0002] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed, and therefore many studies have been conducted.

[0003] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer disposed between the anode and the cathode. The organic material layer generally has a multilayer structure including different materials to improve the efficiency and stability of the organic light-emitting device, for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0004] Among the organic light emitting devices as described above, there is a continuous demand for developing organic light emitting devices having improved driving voltage, efficiency, and lifespan.

[0005] Prior art literature

[0006] Patent Literature

[0007] (Patent Document 1) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the invention

[0008] Technical issues

[0009] The present disclosure relates to organic light emitting devices with improved driving voltage, efficiency, and lifetime.

[0010] Technical Solution

[0011] The following organic light emitting devices are provided herein:

[0012] The organic light emitting device comprises: an anode, a cathode and a light emitting layer arranged between the anode and the cathode.

[0013] The light emitting layer includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2.

[0014] [Chemical formula 1]

[0015]

[0016] Wherein in Chemical Formula 1,

[0017] Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0018] L 1 To L 3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0019] R 1 is hydrogen; deuterium; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0020] a is an integer from 0 to 7,

[0021] [Chemical formula 2]

[0022]

[0023] Wherein in Chemical Formula 2,

[0024] Ar 3 is hydrogen; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0025] Ar 4 and Ar 5 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C 2-60 Heteroaryl,

[0026] L 4 To L 6 are each independently a single bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C 2-60 Heteroarylene, and

[0027] L 7 is substituted or unsubstituted C 6-60 Arylene.

[0028] Beneficial Effects

[0029] The above-mentioned organic light emitting device may improve efficiency, achieve low driving voltage, and / or improve lifespan characteristics by including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 in a light emitting layer. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 is shown.

[0031] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9 and a cathode 4 is shown. DETAILED DESCRIPTION

[0032] Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.

[0033] As used herein, the notation It refers to the bond to another substituent.

[0034] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphino group; or heteroaryl group containing at least one of N, O and S atoms, or unsubstituted or substituted with substituents connected by two or more substituents among the substituents exemplified above. For example, "substituents connected by two or more substituents" can be biphenyl. That is, the biphenyl group can be an aryl group, or it can also be interpreted as a substituent connected by two phenyl groups.

[0035] In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a group having the following structural formula, but is not limited thereto.

[0036]

[0037] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group having the following structural formula, but is not limited thereto.

[0038]

[0039] In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a group having the following structural formula, but is not limited thereto.

[0040]

[0041] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0042] In the present disclosure, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0043] In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0044] In the present disclosure, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0045] In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0046] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0047] In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., which are monocyclic aryl groups, but are not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, base, etc., but not limited thereto.

[0048] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0049] In the present disclosure, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.

[0050] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl and arylamine is the same as the example of the aforementioned aryl. In the present disclosure, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the example of the aforementioned alkyl. In the present disclosure, the heteroaryl in heteroarylamine can apply the description of the aforementioned heterocyclic group. In the present disclosure, the alkenyl in aralkenyl is the same as the example of the aforementioned alkenyl. In the present disclosure, the description of the aforementioned aryl can be applied, except that the arylene group is a divalent group. In the present disclosure, the description of the aforementioned heteroaryl can be applied, except that the heteroarylene group is a divalent group. In the present disclosure, the description of the aforementioned aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the description of the aforementioned heterocyclic group can be applied, except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

[0051] Hereinafter, the present disclosure will be described in detail with respect to each configuration.

[0052] Anode and cathode

[0053] An anode and a cathode used in the present disclosure mean electrodes used in an organic light emitting device.

[0054] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; and the like, but not limited thereto.

[0055] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO 2 / Al; and so on, but not limited to.

[0056] Hole injection layer

[0057] If necessary, the organic light emitting device according to the present disclosure may further include a hole injection layer on the anode.

[0058] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, a hole injection effect in the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and has excellent film forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0059] Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, Organic materials, conductive polymers based on anthraquinone, polyaniline and polythiophene, etc., but not limited thereto.

[0060] Hole transport layer

[0061] If necessary, the organic light-emitting device according to the present disclosure may include a hole transport layer on the anode (or on the hole injection layer when the hole injection layer is present).

[0062] The hole transport layer is a layer that receives holes from the anode or the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility that can receive holes from the anode or the hole injection layer and transport the holes to the light emitting layer.

[0063] Specific examples of the hole transport material include arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion exist simultaneously, and the like, but are not limited thereto.

[0064] Electron blocking layer

[0065] The electron blocking layer is a layer disposed between the hole transport layer and the light emitting layer to prevent the electrons injected into the cathode from being transferred to the hole transport layer without being recombined in the light emitting layer, and it can also be called an electron suppression layer or an electron blocking layer. The electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.

[0066] Luminescent layer

[0067] The light-emitting layer used in the present disclosure means a layer that can emit light in the visible light region by combining holes and electrons transmitted from the anode and the cathode. Generally, the light-emitting layer includes a host material and a dopant material, and in the present disclosure, includes a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 as a host.

[0068] Preferably, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3:

[0069] [Chemical formula 1-1]

[0070]

[0071] [Chemical formula 1-2]

[0072]

[0073] [Chemical formula 1-3]

[0074]

[0075] In chemical formulas 1-1 to 1-3,

[0076] Ar 1 and Ar 2 , L 1 To L 3 and R 1 As defined in Chemical Formula 1.

[0077] Preferably, Ar 1 and Ar 2 may be independently substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 Heteroaryl,

[0078] More preferably, Ar 1 and Ar 2 may each independently be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl or dibenzothienyl, and

[0079] Most preferably, Ar 1 and Ar2 Can be independently any one selected from the following:

[0080]

[0081] Preferably, L 1 To L 3 may be each independently a single bond, or a substituted or unsubstituted C 6-20 Arylene,

[0082] More preferably, L 1 To L 3 may each independently be a single bond, a phenylene group, a biphenylene group or a naphthylene group, and

[0083] Most preferably, L 1 To L 3 can each independently be a single bond or any one selected from the following:

[0084]

[0085] Preferably, each R 1 may independently be hydrogen; deuterium; substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 Heteroaryl, and

[0086] More preferably, each R 1 The radicals may independently be hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, naphthylphenyl, phenylnaphthyl, fluoranthenyl, indenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl.

[0087] Preferably, a may be 0 or 1. More preferably, a may be 1.

[0088] Preferably, Ar 1 ,Ar 2 and R 1 At least one of them may be naphthyl, phenylnaphthyl, naphthylphenyl, phenanthryl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl.

[0089] More preferably, Ar 1 ,Ar 2 and R 1 At least one of them may be naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, dibenzofuranyl, benzonaphthofuranyl or benzonaphthothiophenyl.

[0090] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0091]

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[0246] For example, the compound represented by Chemical Formula 1 may be prepared according to the preparation method as shown in the following Reaction Scheme 1, and the other remaining compounds may be prepared in a similar manner.

[0247] [Reaction scheme 1]:

[0248]

[0249] In reaction scheme 1, Ar 1 ,Ar 2 , L 1 To L 3 , R 1 and a are as defined in Chemical Formula 1, and X 1 is halogen, preferably X 1 Chlorine or bromine.

[0250] Reaction Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the Suzuki coupling reaction can be modified as known in the art. The above preparation method can be further presented in the preparation examples described below.

[0251] Preferably, Ar 3 It may be hydrogen; substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 Heteroaryl, and

[0252] More preferably, Ar 3 It may be hydrogen or phenyl.

[0253] Preferably, Ar 4 and Ar 5 may be independently substituted or unsubstituted C 6-20 Aryl; or a substituted or unsubstituted C 2-20 Heteroaryl,

[0254] More specifically, Ar 4 and Ar 5 each independently may be phenyl, phenyl substituted with 5 deuteriums, biphenyl, biphenyl substituted with 4 deuteriums, biphenyl substituted with 9 deuteriums, terphenyl, terphenyl substituted with 4 deuteriums, quaterphenyl, naphthyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl or phenyldibenzofuranyl, and

[0255] Most preferably, Ar 4 and Ar 5 Can be independently any one selected from the following:

[0256]

[0257] Preferably, L 4 To L 6 may be independently a single bond; substituted or unsubstituted C 6-20 or a substituted or unsubstituted C 2-20 Heteroarylene,

[0258] More preferably, L 4 To L 6 may each independently be a single bond, a phenylene group, a phenylene group substituted with four deuterium groups, a biphenylene group, a naphthylene group, a phenylnaphthylene group, a carbazolylene group, a phenylcarbazolylene group, a phenylcarbazolylene group substituted with four deuterium groups, a dibenzofuranyl group, a phenyldibenzofuranyl group, a phenyldibenzofuranyl group substituted with four deuterium groups, or a dimethylfluorenyl group, and

[0259] Most preferably, L 4 To L 6 can each independently be a single bond or any one selected from the following:

[0260]

[0261] Preferably, L 4 is a single bond, and L 5 and L 6 may be independently a single bond; substituted or unsubstituted C 6-20 or a substituted or unsubstituted C 2-20 Heteroarylene,

[0262] More preferably, L 4 is a single bond, and L 5 and L 6 may each independently be a single bond, a phenylene group, a phenylene group substituted with four deuterium groups, a biphenylene group, a naphthylene group, a phenylnaphthylene group, a carbazolylene group, a phenylcarbazolylene group, a phenylcarbazolylene group substituted with four deuterium groups, a dibenzofuranyl group, a phenyldibenzofuranyl group, a phenyldibenzofuranyl group substituted with four deuterium groups, or a dimethylfluorenyl group, and

[0263] Most preferably, L 4 is a single bond, and L 5 and L 6 can each independently be a single bond or any one selected from the following:

[0264]

[0265] Preferably, L 7 It can be substituted or unsubstituted C 6-20 Arylene,

[0266] More preferably, L 7 may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group, and

[0267] Most preferably, L 7 It may be a phenylene group, a phenylene group substituted with four deuterium atoms, a biphenylene group, or a naphthylene group.

[0268] Preferably, the compound represented by Chemical Formula 2 can be represented by the following Chemical Formula 2-1:

[0269] [Chemical formula 2-1]

[0270]

[0271] In chemical formula 2-1,

[0272] Ar 3 To Ar 5 and L 4 To L 6 As defined in Chemical Formula 2,

[0273] R 2 is hydrogen, deuterium, or substituted or unsubstituted C 6-60 Aryl, and

[0274] b is an integer from 0 to 4.

[0275] Preferably, R 2 It can be hydrogen, deuterium, or substituted or unsubstituted C 6-20 Aryl, and

[0276] More preferably, R 2 It may be hydrogen or deuterium.

[0277] Representative examples of the compound represented by Chemical Formula 2 are as follows:

[0278]

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[0325] For example, the compound represented by Chemical Formula 2 may be prepared according to the preparation method as shown in the following Reaction Scheme 2, and the other remaining compounds may be prepared in a similar manner.

[0326] [Reaction scheme 2]:

[0327]

[0328] In reaction scheme 2, Ar 3 To Ar 5 and L 4 To L 7 As defined in Chemical Formula 2, and X 2 is halogen, preferably X 2 Chlorine or bromine.

[0329] Reaction Scheme 2 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be modified as known in the art. The above preparation method can be further presented in the preparation examples described below.

[0330] Preferably, a weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 in the light emitting layer is 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0331] Meanwhile, the light-emitting layer may further include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material used for an organic light-emitting device. As examples, aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. may be mentioned. Specific examples of aromatic amine derivatives include substituted or unsubstituted fused aromatic ring derivatives having an arylamino group, examples of which include pyrene, anthracene, and diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, examples of metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0332] Hole blocking layer

[0333] The hole blocking layer is disposed between the electron transport layer and the light emitting layer to prevent holes injected into the anode from being transferred to the electron transport layer without being recombined in the light emitting layer. The hole blocking layer is preferably a material with large ionization energy.

[0334] Electron transport layer

[0335] If necessary, the organic light emitting device according to the present disclosure may include an electron transport layer on the light emitting layer.

[0336] The electron transport layer is a layer that receives electrons from the electron injection layer formed on the cathode and the cathode and transports the electrons to the light-emitting layer, and suppresses the transfer of holes from the light-emitting layer, and the electron transport material is appropriately a material that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer and has a large electron mobility.

[0337] Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline, 3The electron transport layer may be used together with any desired cathode material as used according to conventional techniques. In particular, suitable examples of cathode materials are typical materials with a small work function followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0338] Electron injection layer

[0339] If necessary, the organic light-emitting device according to the present disclosure may further include an electron injection layer on the light-emitting layer (or on the electron transport layer when the electron transport layer is present).

[0340] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated from the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film.

[0341] Specific examples of materials that can be used as the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, Tetracarboxylic acid, fluorenyl methane, anthrone and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but not limited thereto.

[0342] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0343] Meanwhile, in the present disclosure, “electron injection and transport layer” is a layer that functions as both an electron injection layer and an electron transport layer, and materials used as each layer may be used alone or in combination, but are not limited thereto.

[0344] Organic light-emitting devices

[0345] Figure 1 The structure of an organic light emitting device according to the present disclosure is shown. Figure 1An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 is shown. Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9 and a cathode 4 is shown.

[0346] The organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking the above-mentioned structures. In this case, the organic light-emitting device can be manufactured as follows: by using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate to form an anode, forming the above-mentioned layers on the anode, and then depositing a material that can be used as a cathode thereon. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing from a cathode material to an anode material on a substrate in the reverse order of the above-mentioned configuration (WO2003 / 012890). In addition, the light-emitting layer can be formed by subjecting the host and the dopant to a vacuum deposition method and a solution coating method. In this article, the solution coating method means spin coating, dip coating, scraping, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0347] On the other hand, the organic light emitting device according to the present disclosure may be a front side emission type, a rear side emission type, or a double side emission type according to the materials used.

[0348] Hereinafter, preferred embodiments of the present disclosure are presented to help understand the present invention. However, these embodiments are presented only for illustrative purposes, and the scope of the present disclosure is not limited thereto.

[0349] [Preparation Example]

[0350] Preparation Example 1-1: Preparation of Compound 1-1

[0351]

[0352] Compound 1-A (15 g, 60.9 mmol) and compound Trz27 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.8 g, 121.7 mmol) was dissolved in 50 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.9 g of compound sub1-A-1. (Yield: 71%, MS: [M+H] + =484)

[0353]

[0354] Compound sub1-A-1 (15 g, 31 mmol) and compound sub1 (6.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound 1-1. (Yield: 66%, MS: [M+H] + =602)

[0355] Preparation Example 1-2: Preparation of Compound 1-2

[0356]

[0357] Compound 1-A (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.5 g of compound sub1-A-2. (Yield: 74%, MS: [M+H] + =434)

[0358]

[0359] Compound sub1-A-2 (15 g, 34.6 mmol) and compound sub2 (9.4 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 1-2. (Yield: 66%, MS: [M+H] + =626)

[0360] Preparation Example 1-3: Preparation of Compound 1-3

[0361]

[0362] Compound 1-A (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.2 g of compound sub1-A-3. (Yield: 79%, MS: [M+H] + =484)

[0363]

[0364] Compound sub1-A-3 (15 g, 31 mmol) and compound sub3 (7.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (8.6 g, 62 mmol) was then dissolved in 26 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-3. (Yield: 66%, MS: [M+H] + =632)

[0365] Preparation Example 1-4: Preparation of Compound 1-4

[0366]

[0367] Compound 1-A (15 g, 60.9 mmol) and compound Trz4 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26 g of compound sub1-A-4. (Yield: 70%, MS: [M+H] + =610)

[0368]

[0369] Compound sub1-A-4 (15 g, 24.6 mmol) and compound sub4 (5.6 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (6.8 g, 49.2 mmol) was dissolved in 20 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 1-4. (Yield: 60%, MS: [M+H] + =758)

[0370] Preparation Example 1-5: Preparation of Compound 1-5

[0371]

[0372] Compound 1-B (15 g, 60.9 mmol) and compound Trz5 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.2 g of compound sub1-B-1. (Yield: 77%, MS: [M+H] + =560)

[0373]

[0374] Compound sub1-B-1 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-5. (Yield: 80%, MS: [M+H] + =602)

[0375] Preparation Example 1-6: Preparation of Compound 1-6

[0376]

[0377] Compound 1-B (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.2 g of compound sub1-B-2. (Yield: 62%, MS: [M+H] + =484)

[0378]

[0379] Compound sub1-B-2 (15 g, 31 mmol) and compound sub6 (7.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.3 g of compound 1-6. (Yield: 76%, MS: [M+H] + =650)

[0380] Preparation Example 1-7: Preparation of Compound 1-7

[0381]

[0382] Compound 1-B (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.8 g of compound sub1-B-3. (Yield: 79%, MS: [M+H] + =434)

[0383]

[0384] Compound sub1-B-3 (15 g, 34.6 mmol) and compound sub7 (8.6 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.4 g of compound 1-7. (Yield: 74%, MS: [M+H] + =602)

[0385] Preparation Example 1-8: Preparation of Compound 1-8

[0386]

[0387] Compound sub1-B-2 (15 g, 31 mmol) and compound sub8 (8.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.5 g of compound 1-8. (Yield: 75%, MS: [M+H] + =666)

[0388] Preparation Example 1-9: Preparation of Compound 1-9

[0389]

[0390] Compound 1-B (15 g, 60.9 mmol) and compound Trz6 (22.4 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.7 g of compound sub1-B-4. (Yield: 73%, MS: [M+H] + =534)

[0391]

[0392] Compound sub1-B-4 (15 g, 28.1 mmol) and compound sub9 (6 g, 28.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in 23 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.6 g of compound 1-9. (Yield: 62%, MS: [M+H] + =666)

[0393] Preparation Example 1-10: Preparation of Compound 1-10

[0394]

[0395] Compound 1-B (15 g, 60.9 mmol) and compound Trz7 (28.6 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 28.6 g of compound sub1-B-5. (Yield: 74%, MS: [M+H] + =636)

[0396]

[0397] Compound sub1-B-5 (15 g, 23.6 mmol) and compound sub5 (2.9 g, 23.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (6.5 g, 47.2 mmol) was dissolved in 20 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-10. (Yield: 65%, MS: [M+H] + =678)

[0398] Preparation Example 1-11: Preparation of Compound 1-11

[0399]

[0400] Compound 1-B (15 g, 60.9 mmol) and compound Trz8 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.1 g of compound sub1-B-6. (Yield: 63%, MS: [M+H] + =524)

[0401]

[0402] Compound sub1-B-6 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.9 g, 57.3 mmol) was dissolved in 24 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 1-11. (Yield: 65%, MS: [M+H] + =616)

[0403] Preparation Example 1-12: Preparation of Compound 1-12

[0404]

[0405] Compound 1-C (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.6 g of compound sub1-C-1. (Yield: 60%, MS: [M+H] + =484)

[0406]

[0407] Compound sub1-C-1 (15 g, 31 mmol) and compound sub10 (5.3 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (8.6 g, 62 mmol) was dissolved in 26 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-12. (Yield: 72%, MS: [M+H] + =576)

[0408] Preparation Example 1-13: Preparation of Compound 1-13

[0409]

[0410] Compound 1-C (15 g, 60.9 mmol) and compound Trz9 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.5 g of compound sub1-C-2. (Yield: 69%, MS: [M+H] + =560)

[0411]

[0412] Compound sub1-C-2 (15 g, 26.8 mmol) and compound sub10 (4.6 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 1-13. (Yield: 80%, MS: [M+H] + =652)

[0413] Preparation Example 1-14: Preparation of Compound 1-14

[0414]

[0415] Compound 1-C (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.5 g of compound sub1-C-3. (Yield: 66%, MS: [M+H] + =510)

[0416]

[0417] Compound sub1-C-3 (15 g, 29.4 mmol) and compound sub11 (7.3 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (8.1 g, 58.8 mmol) was dissolved in 24 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.3 g of compound 1-14. (Yield: 77%, MS: [M+H] + =678)

[0418] Preparation Example 1-15: Preparation of Compound 1-15

[0419]

[0420] Compound 1-C (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.7 g of compound sub1-C-4. (Yield: 71%, MS: [M+H] + =434)

[0421]

[0422] Compound sub1-C-4 (15 g, 37.1 mmol) and compound sub12 (9.7 g, 37.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (10.3 g, 74.3 mmol) was dissolved in 31 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.6 g of compound 1-15. (Yield: 64%, MS: [M+H] + =616)

[0423] Preparation Example 1-16: Preparation of Compound 1-16

[0424]

[0425] Compound sub1-C-2 (15 g, 26.8 mmol) and compound sub13 (7.4 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.4 g, 53.6 mmol) was dissolved in 22 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.2 g of compound 1-16. (Yield: 80%, MS: [M+H] + =758)

[0426] Preparation Example 1-17: Preparation of Compound 1-17

[0427]

[0428] Compound sub1-C-4 (15 g, 34.6 mmol) and compound sub14 (7.7 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (9.6 g, 69.1 mmol) was dissolved in 29 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound 1-17. (Yield: 62%, MS: [M+H] + =576)

[0429] Preparation Example 1-18: Preparation of Compound 1-18

[0430]

[0431] Compound sub1-C-1 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (8.6 g, 62 mmol) was then dissolved in 26 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12 g of compound 1-18. (Yield: 63%, MS: [M+H] + =616)

[0432] Preparation Example 1-19: Preparation of Compound 1-19

[0433]

[0434] Compound 1-C (15 g, 60.9 mmol) and compound Trz11 (22.4 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.4 g of compound sub1-C-5. (Yield: 69%, MS: [M+H] + =534)

[0435]

[0436] Compound sub1-C-5 (15 g, 28.1 mmol) and compound sub15 (6 g, 28.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.8 g, 56.2 mmol) was dissolved in 23 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 1-19. (Yield: 71%, MS: [M+H] + =666)

[0437] Preparation Example 1-20: Preparation of Compound 1-20

[0438]

[0439] Compound 1-C (15 g, 60.9 mmol) and compound Trz12 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21 g of compound sub1-C-6. (Yield: 66%, MS: [M+H] + =524)

[0440]

[0441] Compound sub1-C-6 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound 1-20. (Yield: 70%, MS: [M+H] + =616)

[0442] Preparation Example 1-21: Preparation of Compound 1-21

[0443]

[0444] Compound 1-C (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.2 g of compound sub1-C-7. (Yield: 77%, MS: [M+H] + =560)

[0445]

[0446] Compound sub1-C-7 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.1 g, 80.3 mmol) was then dissolved in 33 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.5 g of compound 1-21. (Yield: 65%, MS: [M+H] + =602)

[0447] Preparation Example 1-22: Preparation of Compound 1-22

[0448]

[0449] Compound 1-D (15 g, 60.9 mmol) and compound Trz14 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.9 g of compound sub1-D-1. (Yield: 67%, MS: [M+H] + =586)

[0450]

[0451] Compound sub1-D-1 (15 g, 25.6 mmol) and compound sub5 (3.1 g, 25.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (10.6 g, 76.8 mmol) was dissolved in 32 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3 g of compound 1-22. (Yield: 64%, MS: [M+H] + =628)

[0452] Preparation Example 1-23: Preparation of Compound 1-23

[0453]

[0454] Compound 1-D (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20 g of compound sub1-D-2. (Yield: 76%, MS: [M+H] + =434)

[0455]

[0456] Compound sub1-D-2 (15 g, 34.6 mmol) and compound sub16 (9.1 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 1-23. (Yield: 66%, MS: [M+H] + =616)

[0457] Preparation Example 1-24: Preparation of Compound 1-24

[0458]

[0459] Compound 1-D (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.8 g of compound sub1-D-3. (Yield: 67%, MS: [M+H] + =510)

[0460]

[0461] Compound sub1-D-3 (15 g, 29.4 mmol) and compound sub17 (7.7 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 1-24. (Yield: 61%, MS: [M+H] + =692)

[0462] Preparation Example 1-25: Preparation of Compound 1-25

[0463]

[0464] Compound 1-D (15 g, 60.9 mmol) and compound Trz15 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.3 g of compound sub1-D-4. (Yield: 67%, MS: [M+H] + =524)

[0465]

[0466] Compound sub1-D-4 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (11.9 g, 85.9 mmol) was dissolved in 36 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-25. (Yield: 61%, MS: [M+H] + =616)

[0467] Preparation Example 1-26: Preparation of Compound 1-26

[0468]

[0469] Compound sub1-D-3 (15 g, 29.4 mmol) and compound sub18 (6.2 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 1-26. (Yield: 76%, MS: [M+H] + =642)

[0470] Preparation Example 1-27: Preparation of Compound 1-27

[0471]

[0472] Compound 1-D (15 g, 60.9 mmol) and compound Trz16 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 27.1 g of compound sub1-D-5. (Yield: 73%, MS: [M+H] + =610)

[0473]

[0474] Compound sub1-D-5 (15 g, 24.6 mmol) and compound sub9 (5.2 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-27. (Yield: 70%, MS: [M+H] + =742)

[0475] Preparation Example 1-28: Preparation of Compound 1-28

[0476]

[0477] Compound 1-D (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.8 g of compound sub1-D-6. (Yield: 61%, MS: [M+H] + =560)

[0478]

[0479] Compound sub1-D-6 (15 g, 26.8 mmol) and compound sub10 (4.6 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 1-28. (Yield: 70%, MS: [M+H] + =652)

[0480] Preparation Example 1-29: Preparation of Compound 1-29

[0481]

[0482] Compound 1-E (15 g, 60.9 mmol) and compound Trz12 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of compound sub1-E-1. (Yield: 65%, MS: [M+H] + =434)

[0483]

[0484] Compound sub1-E-1 (15 g, 34.6 mmol) and compound sub2 (9.4 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.5 g of compound 1-29. (Yield: 67%, MS: [M+H] + =626)

[0485] Preparation Example 1-30: Preparation of Compound 1-30

[0486]

[0487] Compound 1-E (15 g, 60.9 mmol) and compound Trz9 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.9 g of compound sub1-E-2. (Yield: 79%, MS: [M+H] + =560)

[0488]

[0489] Compound sub1-E-2 (15 g, 26.8 mmol) and compound sub19 (7 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.1 g, 80.3 mmol) was then dissolved in 33 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.9 g of compound 1-30. (Yield: 80%, MS: [M+H] + =742)

[0490] Preparation Example 1-31: Preparation of Compound 1-31

[0491]

[0492] Compound 1-E (15 g, 60.9 mmol) and compound Trz17 (22.4 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 25.3 g of compound sub1-E-3. (Yield: 78%, MS: [M+H] + =534)

[0493]

[0494] Compound sub1-E-3 (15 g, 28.1 mmol) and compound sub20 (7.8 g, 28.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.6 g, 84.3 mmol) was then dissolved in 35 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-31. (Yield: 72%, MS: [M+H] + =732)

[0495] Preparation Example 1-32: Preparation of Compound 1-32

[0496]

[0497] Compound sub1-E-1 (15 g, 34.6 mmol) and compound sub21 (7.7 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.3 g, 103.7 mmol) was then dissolved in 43 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-32. (Yield: 65%, MS: [M+H] + =576)

[0498] Preparation Example 1-33: Preparation of Compound 1-33

[0499]

[0500] Compound 1-E (15 g, 60.9 mmol) and compound Trz15 (21.8 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 25.5 g of compound sub1-E-4. (Yield: 80%, MS: [M+H] + =524)

[0501]

[0502] Compound sub1-E-4 (15 g, 28.6 mmol) and compound sub10 (4.9 g, 28.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.9 g, 85.9 mmol) was then dissolved in 36 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-33. (Yield: 60%, MS: [M+H] + =616)

[0503] Preparation Example 1-34: Preparation of Compound 1-34

[0504]

[0505] Compound 1-E (15 g, 60.9 mmol) and compound Trz3 (19.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.6 g of compound sub1-E-5. (Yield: 60%, MS: [M+H] + =484)

[0506]

[0507] Compound sub1-E-5 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 1-34. (Yield: 60%, MS: [M+H] + =616)

[0508] Preparation Example 1-35: Preparation of Compound 1-35

[0509]

[0510] Compound 1-E (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.7 g of compound sub1-E-6. (Yield: 70%, MS: [M+H] + =510)

[0511]

[0512] Compound sub1-E-6 (15 g, 29.4 mmol) and compound sub22 (7.7 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.6 g of compound 1-35. (Yield: 72%, MS: [M+H] + =692)

[0513] Preparation Example 1-36: Preparation of Compound 1-36

[0514]

[0515] Compound sub1-E-5 (15 g, 31 mmol) and compound sub23 (8.1 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 1-36. (Yield: 60%, MS: [M+H] + =666)

[0516] Preparation Example 1-37: Preparation of Compound 1-37

[0517]

[0518] Compound sub1-E-5 (15 g, 31 mmol) and compound sub10 (5.3 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 1-37. (Yield: 79%, MS: [M+H] + =576)

[0519] Preparation Example 1-38: Preparation of Compound 1-38

[0520]

[0521] Compound 1-E (15 g, 60.9 mmol) and compound Trz18 (27 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.1 g of compound sub1-E-7. (Yield: 65%, MS: [M+H] + =610)

[0522]

[0523] Compound sub1-E-7 (15 g, 24.6 mmol) and compound sub5 (3 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (10.2 g, 73.8 mmol) was then dissolved in 31 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of compound 1-38. (Yield: 63%, MS: [M+H] + =652)

[0524] Preparation Example 1-39: Preparation of Compound 1-39

[0525]

[0526] Compound 1-E (15 g, 60.9 mmol) and compound Trz13 (24 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.2 g of compound sub1-E-8. (Yield: 77%, MS: [M+H] + =560)

[0527]

[0528] Compound sub1-E-8 (15 g, 26.8 mmol) and compound sub5 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.1 g, 80.3 mmol) was then dissolved in 33 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 1-39. (Yield: 68%, MS: [M+H] + =602)

[0529] Preparation Example 1-40: Preparation of Compound 1-40

[0530]

[0531] Compound 1-F (15 g, 60.9 mmol) and compound Trz2 (16.3 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.2 g of compound sub1-F-1. (Yield: 73%, MS: [M+H] + =434)

[0532]

[0533] Compound sub1-F-1 (15 g, 34.6 mmol) and compound sub6 (8.5 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.7 g of compound 1-40. (Yield: 71%, MS: [M+H] + =600)

[0534] Preparation Example 1-41: Preparation of Compound 1-41

[0535]

[0536] Compound 1-F (15 g, 60.9 mmol) and compound Trz10 (20.9 g, 60.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (25.2 g, 182.6 mmol) was then dissolved in 76 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.1 g of compound sub1-F-2. (Yield: 68%, MS: [M+H] + =510)

[0537]

[0538] Compound sub1-F-2 (15 g, 29.4 mmol) and compound sub1 (5.8 g, 29.4 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.2 g, 88.2 mmol) was dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.2 g of compound 1-41. (Yield: 77%, MS: [M+H] + =628)

[0539] Preparation Example 1-42: Preparation of Compound 1-42

[0540]

[0541] Compound Trz7 (15g, 31.9mmol) and compound sub9 (6.8g, 31.9mmol) were added to 300ml THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (13.2g, 95.8mmol) was then dissolved in 40ml water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2g, 0.3mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.2g of compound 1-42. (Yield: 79%, MS: [M+H] + =602)

[0542] Preparation Example 1-43: Preparation of Compound 1-43

[0543]

[0544] Compound Trz16 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-43. (Yield: 77%, MS: [M+H] + =576)

[0545] Preparation Example 1-44: Preparation of Compound 1-44

[0546]

[0547] Compound Trz4 (15g, 33.8mmol) and compound sub9 (7.2g, 33.8mmol) were added to 300ml THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14g, 101.4mmol) was then dissolved in 42ml water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2g, 0.3mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.2g of compound 1-44. (Yield: 73%, MS: [M+H] + =576)

[0548] Preparation Example 1-45: Preparation of Compound 1-45

[0549]

[0550] Compound Trz1 (15 g, 35.7 mmol) and compound sub9 (7.6 g, 35.7 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.8 g, 107.2 mmol) was then dissolved in 44 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 1-45. (Yield: 62%, MS: [M+H] + =552)

[0551] Preparation Example 1-46: Preparation of Compound 1-46

[0552]

[0553] Compound Trz19 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound 1-46. (Yield: 70%, MS: [M+H] + =576)

[0554] Preparation Example 1-47: Preparation of Compound 1-47

[0555]

[0556] Compound Trz20 (15 g, 35.9 mmol) and compound sub9 (7.6 g, 35.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14.9 g, 107.7 mmol) was then dissolved in 45 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-47. (Yield: 76%, MS: [M+H] + =550)

[0557] Preparation Example 1-48: Preparation of Compound 1-48

[0558]

[0559] Compound Trz3 (15 g, 47.2 mmol) and compound sub24 (9.7 g, 47.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in 59 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 sub1-G-1. (Yield: 62%, MS: [M+H] + =444)

[0560]

[0561] Compound sub1-G-1 (15 g, 33.8 mmol) and compound sub9 (7.2 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (14 g, 101.4 mmol) was then dissolved in 42 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.2 g of compound 1-48. (Yield: 78%, MS: [M+H] + =576)

[0562] Preparation Example 1-49: Preparation of Compound 1-49

[0563]

[0564] Compound Trz15 (15 g, 41.9 mmol) and compound sub25 (8.7 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound sub1-G-2. (Yield: 62%, MS: [M+H] + =484)

[0565]

[0566] Compound sub1-G-2 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-49. (Yield: 72%, MS: [M+H] + =616)

[0567] Preparation Example 1-50: Preparation of Compound 1-50

[0568]

[0569] Compound Trz21 (15 g, 36.8 mmol) and compound sub26 (5.8 g, 36.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 sub1-G-3. (Yield: 72%, MS: [M+H] + =484)

[0570]

[0571] Compound sub1-G-3 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-50. (Yield: 69%, MS: [M+H] + =616)

[0572] Preparation Example 1-51: Preparation of Compound 1-51

[0573]

[0574] Compound Trz16 (15 g, 36.8 mmol) and compound sub27 (5.3 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound sub1-G-4. (Yield: 76%, MS: [M+H] + =520)

[0575]

[0576] Compound sub1-G-4 (15 g, 28.8 mmol) and compound sub9 (6.1 g, 28.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12 g, 86.5 mmol) was then dissolved in 36 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 1-51. (Yield: 71%, MS: [M+H] + =652)

[0577] Preparation Example 1-52: Preparation of Compound 1-52

[0578]

[0579] Compound Trz22 (15 g, 36.8 mmol) and compound sub28 (5.8 g, 36.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.2 g, 110.3 mmol) was dissolved in 46 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 sub1-G-5. (Yield: 72%, MS: [M+H] + =484)

[0580]

[0581] Compound sub1-G-5 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-52. (Yield: 68%, MS: [M+H] + =616)

[0582] Preparation Example 1-53: Preparation of Compound 1-53

[0583]

[0584] Compound Trz23 (15 g, 34.6 mmol) and compound sub27 (5.4 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.3 g of compound sub1-G-6. (Yield: 64%, MS: [M+H] + =510)

[0585]

[0586] Compound sub1-G-6 (15 g, 31 mmol) and compound sub9 (6.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.9 g, 93 mmol) was then dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-53. (Yield: 68%, MS: [M+H] + =616)

[0587] Preparation Example 1-54: Preparation of Compound 1-54

[0588]

[0589] Compound sub-G-1 (15 g, 33.8 mmol) and compound 1-E (8.3 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound sub1-E-9. (Yield: 70%, MS: [M+H] + =610)

[0590]

[0591] Compound sub1-E-9 (15 g, 24.6 mmol) and compound sub10 (3 g, 24.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (10.2 g, 73.8 mmol) was dissolved in 31 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 1-54. (Yield: 76%, MS: [M+H] + =652)

[0592] Preparation Example 1-55: Preparation of Compound 1-55

[0593]

[0594] Compound Trz2 (15 g, 56 mmol) and compound sub24 (11.6 g, 56 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (23.2 g, 168.1 mmol) was dissolved in 70 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.6 g of compound sub1-G-7. (Yield: 71%, MS: [M+H] + =394)

[0595]

[0596] Compound sub1-G-7 (15 g, 38.1 mmol) and compound 1-B (9.4 g, 38.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound sub1-B-7. (Yield: 65%, MS: [M+H] + =560)

[0597]

[0598] Compound sub1-B-7 (15 g, 26.8 mmol) and compound sub10 (3.3 g, 26.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (11.1 g, 80.3 mmol) was dissolved in 33 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-55. (Yield: 80%, MS: [M+H] + =602)

[0599] Preparation Example 1-56: Preparation of Compound 1-56

[0600]

[0601] Compound Trz24 (15 g, 38.1 mmol) and compound sub25 (9.4 g, 38.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (15.8 g, 114.3 mmol) was dissolved in 47 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound sub1-G-8. (Yield: 65%, MS: [M+H] + =560)

[0602]

[0603] Compound sub1-G-8 (15 g, 30 mmol) and compound sub9 (6.4 g, 30 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 90 mmol) was then dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-56. (Yield: 71%, MS: [M+H] + =632)

[0604] Preparation Example 1-57: Preparation of Compound 1-57

[0605]

[0606] Compound Trz25 (15 g, 41.9 mmol) and compound sub24 (8.7 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound sub1-G-9. (Yield: 61%, MS: [M+H] + =484)

[0607]

[0608] Compound sub1-G-9 (15 g, 31 mmol) and compound 1-F (7.6 g, 31 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12.9 g, 93 mmol) was dissolved in 39 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.5 g of compound sub1-F-3. (Yield: 62%, MS: [M+H] + =650)

[0609]

[0610] Compound sub1-F-3 (15 g, 23.1 mmol) and compound sub10 (2.8 g, 23.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in 29 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-57. (Yield: 80%, MS: [M+H] + =692)

[0611] Preparation Example 1-58: Preparation of Compound 1-58

[0612]

[0613] Compound Trz26 (15 g, 33.8 mmol) and compound sub26 (5.3 g, 33.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14 g, 101.4 mmol) was dissolved in 42 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.5 g of compound sub1-G-10. (Yield: 60%, MS: [M+H] + =520)

[0614]

[0615] Compound sub1-G-10 (15 g, 28.8 mmol) and compound 1-D (7.1 g, 28.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 sub1-D-7. (Yield: 76%, MS: [M+H] + =686)

[0616]

[0617] Compound sub1-D-7 (15 g, 21.9 mmol) and compound 10 (2.7 g, 21.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (9.1 g, 65.6 mmol) was then dissolved in 27 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 12 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 1-58. (Yield: 62%, MS: [M+H] + =728)

[0618] Preparation Example 1-59: Preparation of Compound 1-59

[0619]

[0620] Compound Trz15 (15 g, 41.9 mmol) and compound sub24 (8.7 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound sub1-G-11. (Yield: 61%, MS: [M+H] + =484)

[0621]

[0622] Compound sub1-G-11 (15 g, 28.8 mmol) and compound 1-F (7.1 g, 28.8 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (12 g, 86.5 mmol) was dissolved in 36 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 sub1-F-4. (Yield: 76%, MS: [M+H] + =686)

[0623]

[0624] Compound sub1-F-4 (15 g, 23.1 mmol) and compound sub10 (2.8 g, 23.1 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (9.6 g, 69.2 mmol) was dissolved in 29 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.1 g of compound 1-59. (Yield: 76%, MS: [M+H] + =692)

[0625] Preparation Example 1-60: Preparation of Compound 1-60

[0626]

[0627] Compound Trz12 (15 g, 41.9 mmol) and compound sub28 (6.6 g, 41.9 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (17.4 g, 125.8 mmol) was dissolved in 52 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.1 g of compound sub1-G-12. (Yield: 61%, MS: [M+H] + =434)

[0628]

[0629] Compound sub1-G-12 (15 g, 34.6 mmol) and compound 1-D (8.5 g, 34.6 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (14.3 g, 103.7 mmol) was dissolved in 43 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound sub1-D-8. (Yield: 79%, MS: [M+H] + =500)

[0630]

[0631] Compound sub1-D-8 (15 g, 25 mmol) and compound sub10 (4.3 g, 25 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (10.4 g, 75 mmol) was dissolved in 31 ml of water, added to the mixture, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved in chloroform again, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 1-60. (Yield: 77%, MS: [M+H] + =692)

[0632] Preparation Example 2-1: Preparation of Compound 2-1

[0633]

[0634] Compound 2-A (15 g, 58.3 mmol) and compound 2-B (10 g, 64.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.7 mmol) was then dissolved in 48 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound sub2-A-1. (Yield: 75%, MS: [M+H] + =289)

[0635]

[0636] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-1 (12.9 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.7 g of compound 2-1. (Yield: 59%, MS: [M+H] + =624)

[0637] Preparation Example 2-2: Preparation of Compound 2-2

[0638]

[0639] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-2 (11.1 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.1 g of compound 2-2. (Yield: 51%, MS: [M+H] + =574)

[0640] Preparation Example 2-3: Preparation of Compound 2-3

[0641]

[0642] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-3 (14.3 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 2-3. (Yield: 53%, MS: [M+H] + =664)

[0643] Preparation Example 2-4: Preparation of Compound 2-4

[0644]

[0645] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-4 (13.9 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 2-4. (Yield: 62%, MS: [M+H] + =654)

[0646] Preparation Example 2-5: Preparation of Compound 2-5

[0647]

[0648] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-5 (13.8 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 2-5. (Yield: 50%, MS: [M+H] + =650)

[0649] Preparation Example 2-6: Preparation of Compound 2-6

[0650]

[0651] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-6 (14.8 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2 g of compound 2-6. (Yield: 52%, MS: [M+H] + =680)

[0652] Preparation Example 2-7: Preparation of Compound 2-7

[0653]

[0654] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-7 (12.2 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 1 g of compound 2-7. (Yield: 50%, MS: [M+H] + =61)

[0655] Preparation Example 2-8: Preparation of Compound 2-8

[0656]

[0657] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-8 (13.9 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 2-8. (Yield: 59%, MS: [M+H] + =654)

[0658] Preparation Example 2-9: Preparation of Compound 2-9

[0659]

[0660] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-9 (9.3 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 2-9. (Yield: 62%, MS: [M+H] + =522)

[0661] Preparation Example 2-10: Preparation of Compound 2-10

[0662]

[0663] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-10 (14.5 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 2-10. (Yield: 62%, MS: [M+H] + =572)

[0664] Preparation Example 2-11: Preparation of Compound 2-11

[0665]

[0666] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-11 (13.4 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4 g of compound 2-11. (Yield: 56%, MS: [M+H] + =638)

[0667] Preparation Example 2-12: Preparation of Compound 2-12

[0668]

[0669] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-12 (12 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 2-12. (Yield: 53%, MS: [M+H] + =598)

[0670] Preparation Example 2-13: Preparation of Compound 2-13

[0671]

[0672] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-13 (14.3 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.6 g of compound 2-13. (Yield: 68%, MS: [M+H] + =664)

[0673] Preparation Example 2-14: Preparation of Compound 2-14

[0674]

[0675] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-14 (13.3 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-14. (Yield: 60%, MS: [M+H] + =638)

[0676] Preparation Example 2-15: Preparation of Compound 2-15

[0677]

[0678] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-15 (13.9 g, 34.6 mmol) and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12 g of compound 2-15. (Yield: 53%, MS: [M+H] + =654)

[0679] Preparation Example 2-16: Preparation of Compound 2-16

[0680]

[0681] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-16 (12.7 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.7 g of compound 2-16. (Yield: 64%, MS: [M+H] + =618)

[0682] Preparation Example 2-17: Preparation of Compound 2-17

[0683]

[0684] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-17 (12.1 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 2-17. (Yield: 55%, MS: [M+H] + =602)

[0685] Preparation Example 2-18: Preparation of Compound 2-18

[0686]

[0687] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-18 (12.1 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 2-18. (Yield: 69%, MS: [M+H] + =602)

[0688] Preparation Example 2-19: Preparation of Compound 2-19

[0689]

[0690] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-19 (13.2 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 2-19. (Yield: 52%, MS: [M+H] + =634)

[0691] Preparation Example 2-20: Preparation of Compound 2-20

[0692]

[0693] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-20 (12.5 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-20. (Yield: 62%, MS: [M+H] + =614)

[0694] Preparation Example 2-21: Preparation of Compound 2-21

[0695]

[0696] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-21 (14.3 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.2 g of compound 2-21. (Yield: 62%, MS: [M+H] + =664)

[0697] Preparation Example 2-22: Preparation of Compound 2-22

[0698]

[0699] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-22 (12 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 2-22. (Yield: 54%, MS: [M+H] + =598)

[0700] Preparation Example 2-23: Preparation of Compound 2-23

[0701]

[0702] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-23 (11.1 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.9 g of compound 2-23. (Yield: 60%, MS: [M+H] + =572)

[0703] Preparation Example 2-24: Preparation of Compound 2-24

[0704]

[0705] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-24 (12.9 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound 2-24. (Yield: 63%, MS: [M+H] + =624)

[0706] Preparation Example 2-25: Preparation of Compound 2-25

[0707]

[0708] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-25 (13.3 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.3 g of compound 2-25. (Yield: 65%, MS: [M+H] + =638)

[0709] Preparation Example 2-26: Preparation of Compound 2-26

[0710]

[0711] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-26 (12.5 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of compound 2-26. (Yield: 51%, MS: [M+H] + =614)

[0712] Preparation Example 2-27: Preparation of Compound 2-27

[0713]

[0714] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-27 (14.6 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.1 g of compound 2-27. (Yield: 69%, MS: [M+H] + =674)

[0715] Preparation Example 2-28: Preparation of Compound 2-28

[0716]

[0717] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-28 (13.8 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 2-28. (Yield: 50%, MS: [M+H] + =650)

[0718] Preparation Example 2-29: Preparation of Compound 2-29

[0719]

[0720] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-29 (16.4 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.1 g of compound 2-29. (Yield: 68%, MS: [M+H] + =726)

[0721] Preparation Example 2-30: Preparation of Compound 2-30

[0722]

[0723] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-30 (13.8 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 2-30. (Yield: 64%, MS: [M+H] + =650)

[0724] Preparation Example 2-31: Preparation of Compound 2-31

[0725]

[0726] Compound 2-A (15 g, 58.3 mmol) and compound 2-C (10 g, 64.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.7 mmol) was then dissolved in 48 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and 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 sub2-A-2. (Yield: 63%, MS: [M+H] + =289)

[0727]

[0728] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub2-31 (15.1 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.7 g of compound 2-31. (Yield: 70%, MS: [M+H] + =688)

[0729] Preparation Example 2-32: Preparation of Compound 2-32

[0730]

[0731] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub2-32 (17.7 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.6 g of compound 2-32. (Yield: 63%, MS: [M+H] + =763)

[0732] Preparation Example 2-33: Preparation of Compound 2-33

[0733]

[0734] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub2-33 (14.6 g, 34.6 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-33. (Yield: 54%, MS: [M+H] + =674)

[0735] Preparation Example 2-34: Preparation of Compound 2-34

[0736]

[0737] Compound 2-A (15 g, 58.3 mmol) and compound 2-D (14.9 g, 64.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.7 mmol) was then dissolved in 48 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 10 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of compound sub2-A-3. (Yield: 79%, MS: [M+H] + =365)

[0738]

[0739] Compound sub2-A-3 (10 g, 27.4 mmol), compound sub2-34 (8.8 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound 2-34. (Yield: 63%, MS: [M+H] + =650)

[0740] Preparation Example 2-35: Preparation of Compound 2-35

[0741]

[0742] Compound sub2-A-3 (10 g, 27.4 mmol), compound sub2-35 (8.1 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 2-35. (Yield: 51%, MS: [M+H] + =624)

[0743] Preparation Example 2-36: Preparation of Compound 2-36

[0744]

[0745] Compound sub2-A-3 (10 g, 27.4 mmol), compound sub2-36 (9.6 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.1 g of compound 2-36. (Yield: 65%, MS: [M+H] + =680)

[0746] Preparation Example 2-37: Preparation of Compound 2-37

[0747]

[0748] Compound 2-A (15 g, 58.3 mmol) and compound 2-E (14.9 g, 64.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.7 mmol) was then dissolved in 48 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.2 g of compound sub2-A-4. (Yield: 67%, MS: [M+H] + =365)

[0749]

[0750] Compound sub2-A-4 (10 g, 27.4 mmol), compound sub2-37 (10.9 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.9 g of compound 2-37. (Yield: 70%, MS: [M+H] + =726)

[0751] Preparation Example 2-38: Preparation of Compound 2-38

[0752]

[0753] Compound sub2-A-4 (10 g, 27.4 mmol), compound sub2-38 (10.2 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of compound 2-38. (Yield: 56%, MS: [M+H] + =700)

[0754] Preparation Example 2-39: Preparation of Compound 2-39

[0755]

[0756] Compound sub2-A-4 (10 g, 27.4 mmol), compound sub2-39 (10 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-39. (Yield: 62%, MS: [M+H] + =694)

[0757] Preparation Example 2-40: Preparation of Compound 2-40

[0758]

[0759] Compound 2-A (15 g, 58.3 mmol) and compound 2-F (14.9 g, 64.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.7 mmol) was then dissolved in 48 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 8 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound sub2-A-5. (Yield: 68%, MS: [M+H] + =365)

[0760]

[0761] Compound sub2-A-5 (10 g, 27.4 mmol), compound sub2-40 (10.2 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7 g of compound 2-40. (Yield: 56%, MS: [M+H] + =700)

[0762] Preparation Example 2-41: Preparation of Compound 2-41

[0763]

[0764] Compound sub2-A-5 (10 g, 27.4 mmol), compound sub2-41 (10.2 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8 g of compound 2-41. (Yield: 51%, MS: [M+H] + =700)

[0765] Preparation Example 2-42: Preparation of Compound 2-42

[0766]

[0767] Compound sub2-A-5 (10 g, 27.4 mmol), compound sub2-42 (11.3 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound 2-42. (Yield: 57%, MS: [M+H] + =740)

[0768] Preparation Example 2-43: Preparation of Compound 2-43

[0769]

[0770] Compound 2-A (15 g, 58.3 mmol) and compound 2-G (14.9 g, 64.2 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.1 g, 116.7 mmol) was then dissolved in 48 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 9 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.7 g of compound sub2-A-6. (Yield: 69%, MS: [M+H] + =365)

[0771]

[0772] Compound sub2-A-6 (10 g, 27.4 mmol), compound sub2-43 (8.1 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound 2-43. (Yield: 57%, MS: [M+H] + =624)

[0773] Preparation Example 2-44: Preparation of Compound 2-44

[0774]

[0775] Compound sub2-A-6 (10 g, 27.4 mmol), compound sub2-44 (11.7 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12 g of compound 2-44. (Yield: 58%, MS: [M+H] + =756)

[0776] Preparation Example 2-45: Preparation of Compound 2-45

[0777]

[0778] Compound sub45 (10 g, 70.3 mmol), compound sub2-A-2 (42.6 g, 147.7 mmol) and sodium tert-butoxide (16.9 g, 175.8 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.7 g, 1.4 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 31 g of compound 2-45. (Yield: 68%, MS: [M+H] + =648)

[0779] Preparation Example 2-46: Preparation of Compound 2-46

[0780]

[0781] Compound sub46 (10 g, 59.1 mmol), compound sub2-A-2 (35.8 g, 124.1 mmol) and sodium tert-butoxide (14.2 g, 147.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.7 g of compound 2-46. (Yield: 67%, MS: [M+H] + =674)

[0782] Preparation Example 2-47: Preparation of Compound 2-47

[0783]

[0784] Compound sub47 (10 g, 38.6 mmol), compound sub2-A-2 (23.4 g, 81 mmol) and sodium tert-butoxide (9.3 g, 96.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15 g of compound 2-47. (Yield: 51%, MS: [M+H] + =764)

[0785] Preparation Example 2-48: Preparation of Compound 2-48

[0786]

[0787] Compound sub2-A-6 (10 g, 27.4 mmol), compound sub48 (6 g, 27.4 mmol) and sodium tert-butoxide (2.9 g, 30.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9 g of compound sub2-B-1. (Yield: 60%, MS: [M+H] + =548)

[0788]

[0789] Compound sub2-B-1 (10 g, 18.3 mmol), compound sub2-A-1 (5.3 g, 18.3 mmol) and sodium tert-butoxide (2.3 g, 23.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 2-48. (Yield: 53%, MS: [M+H] + =800)

[0790] Preparation Example 2-49: Preparation of Compound 2-49

[0791]

[0792] Compound sub49 (10 g, 59.1 mmol), compound sub2-A-1 (35.8 g, 124.1 mmol) and sodium tert-butoxide (14.2 g, 147.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.7 g of compound 2-49. (Yield: 57%, MS: [M+H] + =674)

[0793] Preparation Example 2-50: Preparation of Compound 2-50

[0794]

[0795] Compound sub50 (10 g, 47.8 mmol), compound sub2-A-1 (29 g, 100.3 mmol) and sodium tert-butoxide (11.5 g, 119.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.9 g of compound 2-50. (Yield: 70%, MS: [M+H] + =714)

[0796] Preparation Example 2-51: Preparation of Compound 2-51

[0797]

[0798] Compound sub51 (10 g, 38.7 mmol), compound sub2-A-1 (23.5 g, 81.3 mmol) and sodium tert-butoxide (9.3 g, 96.8 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of compound 2-51. (Yield: 57%, MS: [M+H] + =763)

[0799] Preparation Example 2-52: Preparation of Compound 2-52

[0800]

[0801] Compound sub2-A-6 (10 g, 27.4 mmol), compound sub46 (4.6 g, 27.4 mmol) and sodium tert-butoxide (2.9 g, 30.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4 g of compound sub2-B-2. (Yield: 69%, MS: [M+H] + =498)

[0802]

[0803] Compound sub2-B-2 (10 g, 20.1 mmol), compound sub2-A-2 (5.8 g, 20.1 mmol) and sodium tert-butoxide (2.5 g, 26.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.3 g of compound 2-52. (Yield: 55%, MS: [M+H] + =750)

[0804] Preparation Example 2-53: Preparation of Compound 2-53

[0805]

[0806] Compound sub2-A-6 (10 g, 27.4 mmol), compound sub52 (2.6 g, 27.4 mmol) and sodium tert-butoxide (2.9 g, 30.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 5.9 g of compound sub2-B-3. (Yield: 51%, MS: [M+H] + =422)

[0807]

[0808] Compound sub2-B-3 (10 g, 23.7 mmol), compound sub2-A-1 (6.9 g, 23.7 mmol) and sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound 2-53. (Yield: 58%, MS: [M+H] + =674)

[0809] Preparation Example 2-54: Preparation of Compound 2-54

[0810]

[0811] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub53 (8.5 g, 34.6 mmol) and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5 g of compound sub2-B-4. (Yield: 67%, MS: [M+H] + =498)

[0812]

[0813] Compound sub2-B-4 (10 g, 20.1 mmol), compound sub2-A-1 (5.8 g, 20.1 mmol) and sodium tert-butoxide (2.5 g, 26.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound 2-54. (Yield: 50%, MS: [M+H] + =750)

[0814] Preparation Example 2-55: Preparation of Compound 2-55

[0815]

[0816] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub45 (5 g, 34.6 mmol) and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3 g of compound sub2-B-5. (Yield: 68%, MS: [M+H] + =396)

[0817]

[0818] Compound sub2-B-5 (10 g, 25.3 mmol), compound sub2-A-1 (7.3 g, 25.3 mmol) and sodium tert-butoxide (3.2 g, 32.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10 g of compound 2-55. (Yield: 61%, MS: [M+H] + =648)

[0819] Preparation Example 2-56: Preparation of Compound 2-56

[0820]

[0821] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub54 (6.7 g, 34.6 mmol) and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6 g of compound sub2-B-6. (Yield: 56%, MS: [M+H] + =446)

[0822]

[0823] Compound sub2-B-6 (10 g, 22.4 mmol), compound sub2-A-1 (6.5 g, 22.4 mmol) and sodium tert-butoxide (2.8 g, 29.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8 g of compound 2-56. (Yield: 56%, MS: [M+H] + =698)

[0824] Preparation Example 2-57: Preparation of Compound 2-57

[0825]

[0826] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub55 (11.5 g, 34.6 mmol) and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound sub2-B-7. (Yield: 65%, MS: [M+H] + =586)

[0827]

[0828] Compound sub2-B-7 (10 g, 17.1 mmol), compound sub2-A-1 (4.9 g, 17.1 mmol) and sodium tert-butoxide (2.1 g, 22.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound 2-57. (Yield: 54%, MS: [M+H] + =838)

[0829] Preparation Example 2-58: Preparation of Compound 2-58

[0830]

[0831] Compound sub2-A-2 (10 g, 34.6 mmol), compound sub51 (8.9 g, 34.6 mmol) and sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8 g of compound sub2-B-8. (Yield: 61%, MS: [M+H] + =511)

[0832]

[0833] Compound sub2-B-8 (10 g, 19.6 mmol), compound sub2-A-1 (5.7 g, 19.6 mmol) and sodium tert-butoxide (2.4 g, 25.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.6 g of compound 2-58. (Yield: 51%, MS: [M+H] + =763)

[0834] Preparation Example 2-59: Preparation of Compound 2-59

[0835]

[0836] Compound sub2-A-6 (10 g, 27.4 mmol), compound sub56 (5.5 g, 27.4 mmol) and sodium tert-butoxide (2.9 g, 30.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.5 g of compound sub2-B-9. (Yield: 52%, MS: [M+H] + =528)

[0837]

[0838] Compound sub2-B-9 (10 g, 19 mmol), compound sub2-A-1 (5.5 g, 19 mmol) and sodium tert-butoxide (2.4 g, 24.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 2-59. (Yield: 59%, MS: [M+H] + =780)

[0839] Preparation Example 2-60: Preparation of Compound 2-60

[0840]

[0841] Compound 2-H (15 g, 45 mmol) and compound 2-B (7.7 g, 49.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 90 mmol) was then dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound sub2-C-1. (Yield: 75%, MS: [M+H] + =365)

[0842]

[0843] Compound sub2-C-1 (10 g, 27.4 mmol), compound sub2-57 (9.5 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.7 g of compound 2-60. (Yield: 69%, MS: [M+H] + =674)

[0844] Preparation Example 2-61: Preparation of Compound 2-61

[0845]

[0846] Compound sub2-C-1 (10 g, 27.4 mmol), compound sub2-32 (14 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-61. (Yield: 55%, MS: [M+H] + =839)

[0847] Preparation Example 2-62: Preparation of Compound 2-62

[0848]

[0849] Compound sub2-C-1 (10 g, 27.4 mmol), compound sub2-58 (10.3 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.5 g of compound 2-62. (Yield: 65%, MS: [M+H] + =704)

[0850] Preparation Example 2-63: Preparation of Compound 2-63

[0851]

[0852] Compound 2-H (15 g, 45 mmol) and compound 2-C (7.7 g, 49.5 mmol) were added to 300 ml of THF under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.4 g, 90 mmol) was then dissolved in 37 ml of water, added to the mixture, and the mixture was fully stirred, and then tetrakis(triphenylphosphine)palladium(0) (1 g, 0.9 mmol) was added. After 11 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and the organic layer was then distilled. It was dissolved again in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound sub2-C-2. (Yield: 75%, MS: [M+H] + =365)

[0853]

[0854] Compound sub2-C-2 (10 g, 27.4 mmol), compound sub2-59 (10.3 g, 27.4 mmol) and sodium tert-butoxide (3.4 g, 35.6 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.5 g of compound 2-63. (Yield: 70%, MS: [M+H] + =704)

[0855] Preparation Example 2-64: Preparation of Compound 2-64

[0856]

[0857] Compound sub52 (10 g, 107.4 mmol), compound sub2-C-1 (82.3 g, 225.5 mmol) and sodium tert-butoxide (25.8 g, 268.4 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (1.1 g, 2.1 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 41 g of compound 2-64. (Yield: 51%, MS: [M+H] + =750)

[0858] Preparation Example 2-65: Preparation of Compound 2-65

[0859]

[0860] Compound sub46 (10 g, 59.1 mmol), compound sub2-C-1 (45.3 g, 124.1 mmol) and sodium tert-butoxide (14.2 g, 147.7 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.2 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 31.2 g of compound 2-65. (Yield: 64%, MS: [M+H] + =826)

[0861] Preparation Example 2-66: Preparation of Compound 2-66

[0862]

[0863] Compound sub60 (10 g, 45.6 mmol), compound sub2-C-1 (34.9 g, 95.8 mmol) and sodium tert-butoxide (11 g, 114 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.7 g of compound 2-66. (Yield: 67%, MS: [M+H] + =876)

[0864] Preparation Example 2-67: Preparation of Compound 2-67

[0865]

[0866] Compound sub61 (10 g, 54.6 mmol), compound sub2-C-1 (41.8 g, 114.6 mmol) and sodium tert-butoxide (13.1 g, 136.5 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) was added thereto. After 5 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 32.1 g of compound 2-67. (Yield: 70%, MS: [M+H] + =840)

[0867] Preparation Example 2-68: Preparation of Compound 2-68

[0868]

[0869] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-62 (15.6 g, 38.1 mmol) and potassium phosphate (22.1 g, 103.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added thereto. After 2 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-68. (Yield: 55%, MS: [M+H] + =663)

[0870] Preparation Example 2-69: Preparation of Compound 2-69

[0871]

[0872] Compound sub2-A-1 (10 g, 34.6 mmol), compound sub2-63 (16.2 g, 38.1 mmol) and potassium phosphate (22.1 g, 103.9 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added thereto. After 2 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-69. (Yield: 54%, MS: [M+H] + =677)

[0873] Preparation Example 2-70: Preparation of Compound 2-70

[0874]

[0875] Compound sub2-C-1 (10 g, 27.4 mmol), compound sub2-64 (7.8 g, 30.1 mmol) and potassium phosphate (17.5 g, 82.2 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 2 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2 g of compound sub2-B-10. (Yield: 70%, MS: [M+H] + =587)

[0876]

[0877] Compound sub2-B-10 (10 g, 17 mmol), compound sub2-A-1 (5.4 g, 18.7 mmol) and potassium phosphate (10.9 g, 51.1 mmol) were added to 200 ml of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added thereto. After 3 hours, when the reaction was complete, the reaction mixture was 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, and then the organic layer was separated, treated with anhydrous magnesium sulfate, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7 g of compound 2-70. (Yield: 61%, MS: [M+H] + =839)

[0878] [Examples and Comparative Examples]

[0879] Comparative Example 1

[0880] It is coated with a thickness of The glass substrate of ITO (indium tin oxide) film is put into the distilled water comprising the detergent dissolved therein, and by ultrasonic cleaning.In this case, the detergent used is the product commercially available from Fischer Co., and distilled water is the distilled water filtered twice by using the filter commercially available from Millipore Co..ITO was washed 30 minutes, then repeated ultrasonic cleaning twice 10 minutes by using distilled water.After completing with distilled water washing, by substrate isopropyl alcohol, acetone and methanol solvent ultrasonic cleaning, and dry, transferred to plasma cleaning machine afterwards.Then, substrate oxygen plasma was cleaned 5 minutes, then transferred to vacuum evaporator.

[0881] On the thus prepared ITO transparent electrode, the following compound HI-1 was formed as a hole injection layer, but the following compound A-1 was p-doped in an amount of 1.5 wt %. The following compound HT-1 was vacuum deposited on the hole injection layer to form a film with a thickness of Then, the following compound EB-1 was vacuum deposited on the hole transport layer to a film thickness of Then, the following compound 1-2 and the following compound Dp-7 were vacuum deposited on the EB-1 deposited film at a weight ratio of 98:2 to form a film with a thickness of The following compound HB-1 was vacuum deposited on the light-emitting layer to a thickness of Then, the following compound ET-1 and the following compound LiQ were vacuum deposited on the hole blocking layer at a ratio of 2:1 to form a layer with a thickness of The electron injection and transport layer is sequentially deposited with lithium fluoride (LiF) and aluminum to have a thickness of 100 Å and 100 Å, respectively. and to form a cathode.

[0882]

[0883] During the above process, the deposition rate of the organic material is maintained at / second to / sec, and the deposition rates of lithium fluoride and aluminum at the cathode were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2*10 -7 Up to 5*10 -6 Entrust.

[0884] Examples 1 to 155

[0885] An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the first host and the second host listed in the following Table 1 were co-deposited at a weight ratio of 1:1 and used instead of Compound 1-2 as a host.

[0886] Comparative Examples 2 to 61

[0887] An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that a host material shown in Table 2 was used instead of Compound 1-2 as a host, and a compound shown in the following Table 2 was used instead of Compound EB-1 as an electron blocking layer material.

[0888] Comparative Examples 62 to 121

[0889] An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the first host and the second host listed in the following Table 3 were co-deposited at a weight ratio of 1:1 and used instead of Compound 1-2 as a host.

[0890] Compounds B-1 to B-12 in Table 3 are as follows.

[0891]

[0892] Comparative Examples 122 to 227

[0893] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the first host and the second host listed in the following Table 4 were co-deposited at a weight ratio of 1:1 and used instead of Compound 1-2 as a host.

[0894] Compounds C-1 to C-12 in Table 4 are as follows.

[0895]

[0896] [Experimental example]

[0897] The voltage, efficiency and lifespan (based on 15 mA / cm 2 ), and the results are shown in the following Tables 1 to 4. The lifespan T95 means the time required for the luminance to decrease to 95% of the initial luminance (6000 nits).

[0898] [Table 1]

[0899]

[0900]

[0901]

[0902]

[0903]

[0904]

[0905]

[0906]

[0907]

[0908]

[0909] [Table 2]

[0910]

[0911]

[0912]

[0913]

[0914] [Table 3]

[0915]

[0916]

[0917]

[0918]

[0919] [Table 4]

[0920]

[0921]

[0922]

[0923]

[0924]

[0925]

[0926] When current was applied to the organic light emitting devices manufactured according to Examples 1 to 155 and Comparative Examples 1 to 227, the results of the above Tables 1 to 4 were obtained. In the organic light emitting device of Comparative Example 1, conventionally widely used materials were used.

[0927] In Comparative Examples 2 to 61, organic light-emitting devices were manufactured by using the compound represented by Chemical Formula 2 of the present disclosure as an electron blocking layer and using a single host as a light-emitting layer in the same manner as in Comparative Example 1. When the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 were co-deposited and used as a light-emitting layer as in the examples of Table 1, it was determined that the driving voltage was reduced and the efficiency and lifespan were increased compared to the comparative examples of Table 2.

[0928] In addition, when the comparative example compounds B-1 to B-12 and the compound represented by Chemical Formula 2 of the present disclosure were co-deposited and used as the light-emitting layer as shown in Table 3, the results showed that the driving voltage was generally increased and the efficiency and lifespan were reduced compared to the combination of the present disclosure. As shown in Table 4, even when the comparative example compounds C-1 to C-12 and the compound represented by Chemical Formula 1 of the present disclosure were co-deposited and used as the light-emitting layer, the results showed that the driving voltage increased and the efficiency and lifespan were reduced.

[0929] From these results, it can be seen that when the compound represented by Chemical Formula 1 as the first host and the compound represented by Chemical Formula 2 as the second host are used in combination, energy transfer to the red dopant in the light-emitting layer is well performed, thereby improving the driving voltage and increasing the efficiency and lifespan. In addition, it can be inferred that the combination of the compounds of the embodiment can form a more stable balance in the light-emitting layer than the combination of the compounds of the comparative example to form excitons by the combination of electrons and holes, thereby further improving the efficiency and lifespan of the manufactured organic light-emitting device.

[0930] That is, when the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 of the present disclosure are used in combination as a host of a light emitting layer, driving voltage, light emitting efficiency, and lifespan characteristics of an organic light emitting device may be improved.

[0931] <Reference Numbers>

[0932] 1: Substrate 2: Anode

[0933] 3: Light-emitting layer 4: Cathode

[0934] 5: Hole injection layer 6: Hole transport layer

[0935] 7: Electron blocking layer 8: Hole blocking layer

[0936] 9: Electron injection and transport layer

Claims

1. An organic light emitting device, include: anode; cathode; as well as A light-emitting layer is disposed between the anode and the cathode, wherein the light emitting layer comprises a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2, [Chemical formula 1] Wherein in Chemical Formula 1, Ar 1 and Ar 2 are each independently deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted phenanthryl, dibenzofuranyl, or dibenzothiophenyl, L 1 To L 3 are each independently a single bond, a phenylene group, a biphenylene group or a naphthylene group, and L 1 To L 3 each independently unsubstituted or deuterium-substituted, R 1 is hydrogen, deuterium, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted phenanthryl, triphenylene, naphthylphenyl, phenylnaphthyl, fluoranthenyl, indanyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, a is an integer from 0 to 7, [Chemical formula 2] Wherein in Chemical Formula 2, Ar 3 is hydrogen; or phenyl which may be substituted with or without deuterium, Ar 4 and Ar 5 each independently represents a phenyl group, a phenyl group substituted with 5 deuterium groups, a biphenyl group, a biphenyl group substituted with 4 deuterium groups, a biphenyl group substituted with 9 deuterium groups, a terphenyl group, a terphenyl group substituted with 4 deuterium groups, a quaterphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, or a dibenzothiophenyl group, L 4 is a single bond, phenylene, phenylene substituted with 4 deuteriums, biphenylene, naphthylene, phenylnaphthylene, carbazolylene, phenylcarbazolylene, phenylcarbazolylene, dibenzofuranylene, phenyldibenzofuranylene, phenyldibenzofuranylene, or dimethylfluorenylene, L 5 and L 6 Each is independently a single bond or any one selected from the following: as well as L 7 is phenylene, biphenylene, or naphthylene, and L 7 Unsubstituted or deuterium substituted.

2. The organic light-emitting device according to claim 1, The compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In chemical formulas 1-1 to 1-3, Ar 1 and Ar 2 , and L 1 To L 3 As defined in claim 1, and R 1 is deuterium, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted phenanthryl, triphenylene, naphthylphenyl, phenylnaphthyl, fluoranthenyl, indanyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

3. The organic light emitting device according to claim 1, Among them, Ar 1 and Ar 2 Each is independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl or dibenzothiophenyl.

4. The organic light emitting device according to claim 1, Where L 1 To L 3 Each is independently a single bond or any one selected from the following:

5. The organic light emitting device according to claim 1, Each R 1 Each is independently hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, naphthylphenyl, phenylnaphthyl, fluoranthenyl, dihydroindenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl or benzonaphthothiophenyl.

6. The organic light emitting device according to claim 1, Among them, Ar 1 ,Ar 2 and R 1 At least one of is naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothienyl, or R 1 is phenylnaphthyl, naphthylphenyl, fluoranthenyl, benzonaphthofuranyl or benzonaphthothienyl.

7. The organic light emitting device according to claim 1, Where a is 0 or 1.

8. The organic light emitting device according to claim 1, The compound represented by Chemical Formula 1 is any one selected from the following:

9. The organic light emitting device according to claim 1, Among them, Ar 3 It is hydrogen or phenyl.

10. The organic light emitting device according to claim 1, Among them, Ar 4 and Ar 5 Each is independently selected from any one of the following:

11. The organic light emitting device according to claim 1, Where L 4 is a single bond or any one selected from the following:

12. The organic light emitting device according to claim 1, The compound represented by Chemical Formula 2 is represented by the following Chemical Formula 2-1: [Chemical formula 2-1] In chemical formula 2-1, Ar 3 To Ar 5 and L 4 To L 6 As defined in claim 1, R 2 is hydrogen, or deuterium, and b is an integer from 0 to 4.

13. The organic light emitting device according to claim 12, wherein R 2 For hydrogen.

14. The organic light emitting device according to claim 1, Wherein the compound represented by Chemical Formula 2 is selected from the following:

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