KR20200131929A - Organic electroluminescence device and monoamine compound for organic electroluminescence device - Google Patents

Abstract

According to one embodiment of the present invention, an organic electroluminescence device comprises: a first electrode; a hole transport area disposed on the first electrode; a light emitting layer disposed on the hole transport area; an electron transport area disposed on the light emitting layer; and a second electrode disposed on the electron transport area. The hole transport area may include a monoamine compound represented by chemical formula 1 to exhibit the high luminous efficiency.

Description

An organic electroluminescent device and a monoamine compound for an organic electroluminescent device {ORGANIC ELECTROLUMINESCENCE DEVICE AND MONOAMINE COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE}

The present invention relates to an organic electroluminescent device and a monoamine compound for an organic electroluminescent device.

Recently, as an image display device, organic electroluminescence displays have been actively developed. An organic electroluminescent display device is different from a liquid crystal display device, and realizes display by recombining holes and electrons injected from the first electrode and the second electrode in the light emitting layer to emit light of a light emitting material containing an organic compound in the light emitting layer. It is a so-called self-luminous display device.

In the application of an organic electroluminescent device to a display device, low driving voltage, high luminous efficiency, and long life of the organic electroluminescent device are required, and development of a material for an organic electroluminescent device capable of stably realizing this is required. have.

An object of the present invention is to provide an amine compound for an organic electroluminescent device and an organic electroluminescent device, and more specifically, to provide an amine compound contained in a hole transport region of a highly efficient organic electroluminescent device and an organic electroluminescent device. For the purpose of work.

An embodiment of the present invention includes a first electrode, a hole transport region provided on the first electrode, a light emitting layer provided on the hole transport region, an electron transport region provided on the light emitting layer, and a second electrode provided on the electron transport region, The hole transport region provides an organic electroluminescent device including a monoamine compound represented by Formula 1 below.

[Formula 1]

In Formula 1, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms, and L is a substituted or unsubstituted arylene group having 6 or more and 30 or less ring carbon atoms, or substituted or unsubstituted Is a heteroarylene group having 2 or more and 30 or less ring carbon atoms, and R ₁ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 or more and 20 or less carbon atoms, and a substituted or unsubstituted ring carbon number 3 or more and 20 The following cycloalkyl groups, or substituted or unsubstituted aryl groups having 6 to 30 carbon atoms forming a ring, R ₂ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or An unsubstituted cycloalkyl group having 3 or more and 20 or less cyclic carbon atoms, a is an integer of 0 or more and 3 or less, m is an integer of 0 or more and 1 or less, n is an integer of 0 or more and 6 or less, and Ar ₁ is 3- In the case of a dibenzofuranyl group, Ar ₂ is not a 9-phenanthryl group, and when Ar ₂ is a 3-dibenzofuranyl group, Ar ₁ is not a 9-phenanthryl group.

The hole transport region may have a multilayer structure having a plurality of layers, and a layer of the plurality of layers in contact with the light emitting layer may include the monoamine compound according to the exemplary embodiment of the present invention.

The hole transport region includes a hole injection layer disposed on the first electrode, a hole transport layer disposed on the hole injection layer, and an electron blocking layer disposed on the hole transport layer, and the electron blocking layer is an embodiment of the present invention described above. It may include a monoamine compound according to an example.

The electron transport region may include a hole blocking layer provided on the emission layer, an electron transport layer provided on the hole blocking layer, and an electron injection layer provided on the electron transport layer.

Formula 1 may be represented by any one of the following Formulas 2 to 8.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 2 to 8, Ar ₁ , Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1.

L may be a substituted or unsubstituted arylene group having 6 or more and 12 or less ring carbon atoms.

L may be a substituted or unsubstituted phenylene group.

Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted aryl group having 6 or more and 12 or less ring carbon atoms.

Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenyl group.

Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted heteroaryl group having 5 or more and 12 or less ring carbon atoms.

Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group.

Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted dibenzothiophene group.

At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted 4-dibenzothiophene group.

The compound represented by Formula 1 may be represented by the following Formula 9.

[Formula 9]

In Formula 9, R ₃ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It may be an aryl group having 6 or more and 30 or less cyclic ring carbon atoms. p may be an integer of 0 or more and 7 or less.

In Formula 9, Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1.

At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted dibenzofuran group.

At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted 1-dibenzofuran group, or a substituted or unsubstituted 4-dibenzofuran group. The compound represented by Formula 1 may be represented by Formula 10 below.

[Formula 10]

In Formula 10, R ₄ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It is a ring-forming aryl group having 6 or more and 30 or less carbon atoms, and q may be an integer of 0 to 7 or less.

In Formula 10, Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1.

The compound represented by Formula 1 may be represented by the following Formula 11.

[Formula 11]

In Formula 11, R ₅ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It is a ring-forming aryl group having 6 to 30 carbon atoms, and r may be an integer of 0 or more and 7 or less.

In Formula 11, Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1.

In Formula 1, at least one of Ar ₁ , Ar ₂ , L, R ₁ , and R ₂ may be substituted with one or more deuterium atoms.

An embodiment of the present invention provides a monoamine compound represented by Chemical Formula 1.

The organic electroluminescent device according to an embodiment of the present invention has excellent efficiency.

The monoamine compound according to an embodiment of the present invention may be used as a material for a hole transport region of an organic electroluminescent device, and by using the monoamine compound, the efficiency and lifespan of the organic electroluminescent device can be improved.

The monoamine compound according to an exemplary embodiment of the present invention may be used as a material for a hole transport region of an organic electroluminescent device, and by using it, there is an effect of reducing the driving voltage of the organic electroluminescent device.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
3 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

The above objects, other objects, features, and advantages of the present invention will be easily understood through the accompanying drawings and the following preferred embodiments. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the embodiments introduced herein are provided so that the disclosed contents may be thorough and complete, and the spirit of the present invention may be sufficiently conveyed to those skilled in the art.

In describing each drawing, similar reference numerals have been used for similar elements. In the accompanying drawings, the dimensions of the structures are shown to be enlarged than actual for clarity of the present invention. Terms such as first and second may be used to describe various components, but the components should not be limited by the terms. These terms are used only for the purpose of distinguishing one component from another component. For example, without departing from the scope of the present invention, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element. Singular expressions include plural expressions unless the context clearly indicates otherwise.

In the present specification, terms such as "comprise" or "have" are intended to designate the presence of features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, but one or more other features. It is to be understood that the presence or addition of elements or numbers, steps, actions, components, parts, or combinations thereof, does not preclude in advance the possibility of being added. Further, when a part such as a layer, film, region, plate, etc. is said to be "on" another part, this includes not only the case where the other part is "directly above", but also the case where there is another part in the middle. Conversely, when a part such as a layer, a film, a region, or a plate is said to be "under" another part, this includes not only the case where the other part is "directly below", but also the case where another part is in the middle.

First, an organic electroluminescent device according to an exemplary embodiment of the present invention will be described with reference to FIGS. 1 to 3.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention. 2 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention. 3 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

1 to 3, the organic electroluminescent device 10 according to an embodiment of the present invention includes a first electrode EL1, a hole transport region HTR, an emission layer EML, and an electron transport region ETR. And a second electrode EL2.

The hole transport region (HTR) includes a monoamine compound according to an embodiment of the present invention. Hereinafter, a monoamine compound according to an embodiment of the present invention will be described in detail, and then each layer of the organic electroluminescent device 10 will be described.

In the present specification, "substituted or unsubstituted" is 1 selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, a silyl group, a boron group, a phosphine group, an alkyl group, an alkenyl group, an aryl group and a heterocyclic group It may mean substituted or unsubstituted with one or more substituents. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, the biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

In the present specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

In the present specification, the alkyl group may be linear, branched or cyclic. The number of carbon atoms in the alkyl group is 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 4 or less. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl Siloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-oxy Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-trico A group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, etc. are mentioned, It is not limited to these.

In the present specification, an aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 12 or less. Examples of the aryl group include phenyl group, naphthyl group, fluorenyl group, anthracenyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, quincphenyl group, sexyphenyl group, biphenylene group, triphenylene group, pyrenyl group, benzofluoro Although a lantenyl group, a chrysenyl group, etc. can be illustrated, it is not limited to these.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the case where the fluorenyl group is substituted are as follows. However, it is not limited thereto.

In the present specification, the heteroaryl group may be a heteroaryl group including one or more of O, N, P, Si, and S as a hetero atom. When the heteroaryl group contains two hetero atoms, the two hetero atoms may be the same as or different from each other. The number of ring carbon atoms in the heteroaryl group is 2 or more and 30 or less or 5 or more and 12 or less. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The polycyclic heteroaryl group may have, for example, a bicyclic or tricyclic structure. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinoline group, quinazoline group, quinoxaline group, phenoxy group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, Indole group, carbazole group, N-aryl carbazole group, N-heteroaryl carbazole group, N-alkylcarbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzoti Offene group, thienothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilol group and dibenzofuran group, etc., but these Not limited.

In the present specification, the silyl group includes an alkyl silyl group and an aryl silyl group. Examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Not limited.

In the present specification, the boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group include, but are not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, diphenyl boron group, and phenyl boron group.

In the present specification, the alkenyl group may be straight or branched. The number of carbon atoms is not particularly limited, but is 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the alkenyl group include, but are not limited to, a vinyl group, 1-butenyl group, 1-pentenyl group, 1,3-butadienyl aryl group, styrenyl group, styrylvinyl group, and the like.

In the present specification, the description of the aryl group is applied except that the arylene group is a divalent group.

In the present specification, the description of the aforementioned heteroaryl group is applied except that the heteroarylene group is a divalent group.

The monoamine compound according to an embodiment of the present invention is represented by the following formula (1).

[Formula 1]

In Formula 1, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

In Formula 1, L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

In Formula 1, R ₁ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It is an aryl group having 6 or more and 30 or less ring carbon atoms.

In Formula 1, R ₂ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms. On the other hand, R ₂ is not an aryl group and a heteroaryl group. When R ₂ is an aryl group and a heteroaryl group, HOMO (Highest Occupied Molecular Orbital) is largely distributed on the naphthalene skeleton side, and accordingly, the electron density on the amine group side is relatively reduced, maintaining the characteristics of the amine group that induces a long life. It is difficult to reduce the lifetime of the organic electroluminescent device. R ₂ a is not an aryl group and a heteroaryl group may comprise all the case when R ₂ is not an aryl group and a heteroaryl group and R ₂ is not substituted with an aryl group, and heteroaryl.

In Formula 1, a is an integer of 0 or more and 3 or less. On the other hand, when a is 2 or more, a plurality of L is the same as or different from each other.

In Formula 1, m is an integer of 0 or more and 1 or less.

In Formula 1, n is an integer of 0 or more and 6 or less. On the other hand, when n is 2 or more, a plurality of R ₂ is the same as or different from each other.

In Formula 1, Ar ₁ is 3-dibenzo-furanyl group if Ar ₂ is a 9-phenanthryl group, not, if Ar ₂ is 3-dibenzo-furanyl group Ar ₁ is not 9-phenanthryl group. That is, the case where 3-dibenzofuranyl group and 9-phenanthryl group are substituted at the same time on a nitrogen atom is excluded. When the 3-dibenzofuranyl group and the 9-phenanthryl group are simultaneously substituted for the nitrogen atom, thermal decomposition may occur due to strong molecular stacking and a high deposition temperature, thereby deteriorating the characteristics of the organic electroluminescent device. I can.

In an embodiment, Formula 1 may be represented by any one of Formulas 2 to 8 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 2 to 8, Ar ₁ , Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1.

In Formula 1, m is 1 and L may be a substituted or unsubstituted arylene group having 6 or more and 12 or less ring carbon atoms. L may be, for example, a substituted or unsubstituted phenylene group. However, it is not limited thereto.

In Formula 1, Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted aryl group having 6 or more and 12 or less ring carbon atoms. Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenyl group. However, it is not limited thereto.

In Formula 1, Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted heteroaryl group having 5 or more and 12 or less ring carbon atoms. Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group. At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted dibenzothiophene group. At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted 4-dibenzothiophene group. At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted dibenzofuran group. At least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted 1-dibenzofuran group, or a substituted or unsubstituted 4-dibenzofuran group. However, it is not limited thereto.

In one embodiment, Formula 1 may be represented by Formula 9 below.

[Formula 9]

In Formula 9, R ₃ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It may be an aryl group having 6 or more and 30 or less carbon atoms forming a ring. R ₃ may be, for example, a hydrogen atom or a deuterium atom.

In Formula 9, p is an integer of 0 or more and 7 or less. Meanwhile, when p is 2 or more, a plurality of R ₃ may be the same or different from each other.

In one embodiment, Formula 1 may be represented by Formula 10 below.

[Formula 10]

In Formula 10, R ₄ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It may be an aryl group having 6 or more and 30 or less carbon atoms forming a ring. R ₄ may be, for example, a hydrogen atom or a deuterium atom.

In Formula 10, q is an integer of 0 or more and 7 or less. Meanwhile, when q is 2 or more, a plurality of R ₄ may be the same or different from each other.

In an embodiment, Formula 1 may be represented by Formula 11.

[Formula 11]

In Formula 11, R ₅ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted It may be an aryl group having 6 or more and 30 or less carbon atoms forming a ring. R ₅ may be, for example, a hydrogen atom or a deuterium atom.

In Formula 11, r is an integer of 0 or more and 7 or less. On the other hand, when r is 2 or more, a plurality of R ₅ may be the same or different from each other.

In Formula 1, R ₂ may be a hydrogen atom or a deuterium atom. In Formula 1, at least one of Ar ₁ , Ar ₂ , L, R ₁ , and R ₂ may be substituted with one or more deuterium atoms. For example, Ar ₁ may be a phenyl group in which two or five deuterium atoms are substituted. Alternatively, each of R ₁ and R ₂ may be a deuterium atom.

The monoamine compound represented by Formula 1 according to an embodiment of the present invention may be any one selected from compounds represented in the following compound groups 1 to 7. However, it is not limited thereto.

[Compound group 1]

[Compound group 2]

[Compound group 3]

[Compound group 4]

[Compound group 5]

[Compound group 6]

[Compound group 7]

The monoamine compound represented by Formula 1 according to an embodiment of the present invention may be any one selected from compounds represented in the following compound group 1-1 to compound group 7-1. However, it is not limited thereto.

[Compound group 1-1]

[Compound group 2-1]

[Compound group 3-1]

[Compound group 4-1]

[Compound group 5-1]

[Compound group 6-1]

[Compound group 7-1]

The monoamine compound according to an embodiment of the present invention includes a condensed ring and a phenylnaphthyl group having high heat resistance and charge resistance, and thus, when applied to an organic electroluminescent device, may contribute to a longer life. Due to the volume of the phenylnaphthyl group, the symmetry of the molecule decreases and crystallization is suppressed, thereby improving the film quality, thus contributing to high efficiency.

Referring again to FIGS. 1 to 3, an organic electroluminescent device according to an embodiment of the present invention will be described. The emission layer (EML) includes the monoamine compound according to the exemplary embodiment of the present invention. For example, the hole transport region (HTR) includes a monoamine compound represented by Chemical Formula 1.

Hereinafter, the difference between the monoamine compound and the monoamine compound according to the exemplary embodiment described above will be described in detail, and portions that are not described depend on the monoamine compound according to the exemplary embodiment of the present invention.

The first electrode EL1 has conductivity. The first electrode EL1 may be a pixel electrode or an anode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium zinc oxide (ITZO). tin zinc oxide). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 is Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg) may be included. Alternatively, a plurality of layer structures including a reflective film or a semi-transmissive film formed of the material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. Can be For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

The thickness of the first electrode EL1 may be about 1000 Å to about 10000 Å, for example, about 1000 Å to about 3000 Å.

The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL.

The hole transport region (HTR) includes a monoamine compound according to an embodiment of the present invention as described above.

The hole transport region HTR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region HTR may have a single layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single layer structure made of a hole injection material and a hole transport material. In addition, the hole transport region HTR has a single layer structure made of a plurality of different materials, or a hole injection layer (HIL)/hole transport layer (HTL) sequentially stacked from the first electrode EL1, and hole injection. Layer (HIL) / hole transport layer (HTL) / hole buffer layer, hole injection layer (HIL) / hole buffer layer, hole transport layer (HTL) / hole buffer layer or hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer ( EBL) may have a structure, but is not limited thereto.

As described above, the hole transport region HTR may have a multilayer structure having a plurality of layers, and a layer contacting the emission layer EML among the plurality of layers may include a monoamine compound represented by Formula 1 . For example, the hole transport region HTR includes a hole injection layer HIL disposed on the first electrode EL1, a hole transport layer HTL disposed on the hole injection layer HIL, and a hole transport layer HTL. The electron blocking layer EBL disposed thereon may be included, and the electron blocking layer EBL may include a monoamine compound represented by Chemical Formula 1. However, the present invention is not limited thereto, and for example, the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport (HTL), and the hole transport layer (HTL) is a monoamine compound represented by Formula 1 It may be to include.

The hole transport region (HTR) may include one or two or more monoamine compounds represented by Chemical Formula 1. For example, the hole transport region HTR may include at least one selected from the compounds represented in compound groups 1 to 7 described above.

For the hole transport area (HTR), various methods such as vacuum evaporation, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI) are used. It can be formed using.

However, the hole transport region may further include the following materials for each layer.

The hole injection layer (HIL) may include, for example, a phthalocyanine compound such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4' ,4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris(N,- (2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA(Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA(Polyaniline /Camphor sulfonicacid), PANI/PSS((Polyaniline)/Poly(4-styrenesulfonate)), NPD(N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), triphenylamine Polyether ketone (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis (pentafluorophenyl) borate], HAT-CN (dipyrazino [2,3-f: 2',3'-h] quinoxaline-2,3 containing ,6,7,10,11-hexacarbonitrile), etc. may be included.

The hole transport layer (HTL) is, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorine derivatives, TPD(N,N'-bis(3-methylphenyl)-N, Triphenylamine derivatives such as N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine), NPD(N ,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), TAPC(4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4 ,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), etc. may also be included.

As described above, the electron blocking layer EBL may include a monoamine compound represented by Chemical Formula 1. However, the present invention is not limited thereto, and the electron blocking layer EBL may include a general material known in the art. The electron blocking layer (EBL) is, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorine derivatives, TPD(N,N'-bis(3-methylphenyl)-N Triphenylamine derivatives such as ,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine), NPD ( N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), TAPC(4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD( 4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl) or mCP.

The thickness of the hole transport region HTR may be about 100 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. The thickness of the hole injection layer HIL may be, for example, about 30 Å to about 1000 Å, and the thickness of the hole transport layer HTL may be about 30 Å to about 1000 Å. For example, the electron blocking layer EBL may have a thickness of about 10 Å to about 1000 Å. When the thickness of the hole transport region (HTR), the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) satisfies the above-described range, satisfactory hole transport characteristics without a substantial increase in driving voltage Can be obtained.

In addition to the aforementioned material, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide. However, it is not limited thereto.

As described above, the hole transport region HTR may further include at least one of a hole buffer layer and an electron blocking layer EBL. The hole buffer layer may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer EML. As a material included in the hole buffer layer, a material capable of being included in the hole transport region HTR may be used. The electron blocking layer EBL is a layer that prevents injection of electrons from the electron transport region ETR to the hole transport region HTR.

The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have a thickness of about 100 Å to about 1000 Å or about 100 Å to about 600 Å, for example. The light emitting layer EML may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

As the material of the light emitting layer (EML), a known light emitting material can be used, and although not particularly limited, a fluoranthene derivative, a pyrene derivative, an arylacetylene derivative, an anthracene derivative, It is selected from fluorene derivatives, perylene derivatives, chrysene derivatives, and the like. Preferably, a pyrene derivative, a perylene derivative, and an anthracene derivative are mentioned. For example, an anthracene derivative represented by the following formula (12) may be used as a host material for the emission layer (EML).

[Formula 12]

In Formula 12, W ₁ to W ₄ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted ring formation An aryl group having 6 or more and 30 or less carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less carbon atoms, or may be bonded to an adjacent group to form a ring, and m1 and m2 are each independently 0 or more 4 They are the following integers, and m3 and m4 are each independently an integer of 0 or more and 5 or less.

When m1 is 1, W ₁ may not be a hydrogen atom, and when m2 is 1, W ₂ may not be a hydrogen atom. When m3 is 1, W ₃ may not be a hydrogen atom, and when m4 is 1 , W ₄ may not be a hydrogen atom.

When m1 is 2 or more, a plurality of W _1s are the same or different from each other. When m2 is 2 or more, the plurality of W ₂ are the same or different from each other. When m3 is 2 or more, a plurality of W ₃ is the same or different from each other. When m4 is 2 or more, a plurality of W ₄ is the same as or different from each other.

As an example, the compound represented by Formula 12 may include a compound represented by the following structural formula. However, the compound represented by Formula 12 is not limited to the following.

The emission layer (EML) is, for example, spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P, 2,2',7,7'-tetrakis(biphenyl-4-yl)-9,9'- Containing any one selected from the group consisting of spirobifluorene (spiro-sexiphenyl)), DSB (distyryl-benzene), DSA (distyryl-arylene), PFO (polyfluorene)-based polymer, and PPV (poly(p-phenylene vinylene)-based polymer) It may also contain a fluorescent material.

The emission layer EML may further include a dopant, and a known material may be used as the dopant. For example, styryl derivatives (eg, 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene(BCzVB), 4-(di-p-tolylamino)-4"-[(di -p-tolylamino)styryl]stilbene(DPAVB), N-(4-((E)-2-(6-((E)-4- (diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)- N-phenylbenzenamine (N-BDAVBi)), perylene and its derivatives (e.g. 2,5,8,11-tetra-t-butylperylene (TBPe)), pyrene and its derivatives (e.g., 1,1 -dipyrene, 1,4-dipyrenylbenzene, 1,4-Bis(N,N-Diphenylamino)pyrene, 1,6-Bis(N,N-Diphenylamino)pyrene), 2,5,8,11-Tetra-t- butylperylene (TBP), TPBi (1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene), etc. may be used as dopants.

The emission layer (EML) is, for example, Alq ₃ (tris(8-hydroxyquinolino)aluminum), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK(poly(N-vinylcarbazole) ), ADN(9,10-di(naphthalene-2-yl)anthracene), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3,5- tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4'-bis( 9-carbazolyl)-2,2′'-dimethyl-biphenyl), MADN(2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), DPEPO(bis[2-(diphenylphosphino)phenyl]ether oxide ), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis (triphenylsilyl) benzene), DPSiO ₃ (Hexaphenylcyclotrisiloxane), DPSiO ₄ (Octaphenylcyclotetra siloxane) or PPF (2,8-Bis (diphenylphosphoryl) dibenzofuran). Can be.

The electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but is not limited thereto.

The electron transport region ETR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure made of an electron injection material and an electron transport material. In addition, the electron transport region ETR has a single layer structure made of a plurality of different materials, or an electron transport layer (ETL)/electron injection layer (EIL) and a hole blocking layer (EIL) sequentially stacked from the light emitting layer EML. HBL)/electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 Å to about 1500 Å.

The electron transport area (ETR) is a vacuum evaporation method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser thermal imaging (LITI), etc. It can be formed using.

When the electron transport region (ETR) includes the electron transport layer (ETL), the electron transport region (ETR) is Alq ₃ (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)- phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, DPEPO(bis[2-(diphenylphosphino) phenyl]ether oxide), 2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2 -yl)phenyl), BCP(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl) )-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1 ,1'-Biphenyl-4-olato)aluminum), Bebq ₂ (berylliumbis(benzoquinolin-10-olate), ADN(9,10-di(naphthalene-2-yl)anthracene), and mixtures thereof, The thickness of the electron transport layers ETL may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layers ETL satisfies the above-described range, Satisfactory electron transport characteristics without a substantial increase in driving voltage. Can be obtained.

When the electron transport region (ETR) includes an electron injection layer (EIL), the electron transport region (ETR) is a lanthanum group metal such as LiF, LiQ (Lithium quinolate), Li ₂ O, BaO, NaCl, CsF, and Yb, Alternatively, a metal halide such as RbCl or RbI may be used, but is not limited thereto. The electron injection layer EIL may also be made of a mixture of an electron transport material and an insulating organo metal salt. The organometallic salt may be a material having an energy band gap of approximately 4 eV or more. Specifically, for example, the organic metal salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. I can. The electron injection layers EIL may have a thickness of about 1 Å to about 100 Å, and about 3 Å to about 90 Å. When the thickness of the electron injection layers EIL satisfies the above-described range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

As mentioned above, the electron transport region ETR may include a hole blocking layer HBL. The hole blocking layer (HBL) is, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), or DPEPO ( bis[2-(diphenylphosphino)phenyl]ether oxide) may be included, but is not limited thereto.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium zinc oxide (ITZO). tin zinc oxide).

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 is Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture containing them (eg, a mixture of Ag and Mg) may be included. Alternatively, a plurality of layer structures including a reflective film or a semi-transmissive film formed of the material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. Can be

Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

In the organic electroluminescent device 10, as voltages are applied to each of the first electrode EL1 and the second electrode EL2, holes injected from the first electrode EL1 pass through the hole transport region HTR. Then, the electrons are transferred to the emission layer EML, and electrons injected from the second electrode EL2 are transferred to the emission layer EML through the electron transport region ETR. Electrons and holes recombine in the emission layer (EML) to generate excitons, and when the excitons fall from the excited state to the ground state, they emit light.

When the organic electroluminescent device 10 is a top emission type, the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a transflective electrode. When the organic electroluminescent device 10 is a bottom emission type, the first electrode EL1 may be a transmissive electrode or a transflective electrode, and the second electrode EL2 may be a reflective electrode.

The organic electroluminescent device 10 according to an embodiment of the present invention is characterized by including a monoamine compound represented by Chemical Formula 1, and thus, high efficiency and long life can be realized. In addition, there is also an effect of reducing the driving voltage.

Hereinafter, the present invention will be described in more detail through specific examples and comparative examples. The following examples are only examples to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

(Synthesis example)

The monoamine compound according to an embodiment of the present invention can be synthesized, for example, as follows. However, the method for synthesizing the monoamine compound according to an embodiment of the present invention is not limited thereto.

One. Synthesis of compound 1

Compound A4, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-1)

In an Ar atmosphere, in a 1 L 3-neck flask, 7-bromo-1-iodonaphthalene 25.00 g (75.1 mmol), phenylboronic acid 10.07 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.13 g (3.0 equiv, 225.2 mmol) ), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-1 (15.95 g, yield 75%) was performed. Got it. FAB-MS was measured, and the mass number m/z = 283 was observed as a molecular ion peak to confirm the intermediate IM-1.

(Synthesis of intermediate IM-2)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-1 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-2 (11.71 g, yield 81%) was performed. Got it. FAB-MS was measured, and the intermediate IM-2 was confirmed by observing the mass number m/z = 314 as a molecular ion peak.

(Synthesis of intermediate IM-3)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 3,5-diphenylaniline 8.57 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-3 (13.81 g, yield 83%) Got it. FAB-MS was measured, and a mass number m/z = 523 was observed as a molecular ion peak to confirm compound IM-3.

(Synthesis of Compound A4)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-3 8.00 g (15.3 mmol), Pd(dba) ₂ 0.26 g (0.03 equiv, 0.5 mmol), NaOtBu 2.94 g (2.0 equiv, 30.6 mmol), Toluene 76 mL, bromobenzene 2.64 g (1.1 equiv, 16.8 mmol) and tBu ₃ P 0.31 g (0.1 equiv, 1.5 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A4 (7.79 g, yield 85%). .

FAB-MS was measured, and a mass number m/z = 599 was observed as a molecular ion peak to confirm Compound A4.

2. Synthesis of Compound A17

Compound A17, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-4)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, p-biphenylamine 5.91 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-4 (11.37 g, yield 80%). Got it. FAB-MS was measured, and the compound IM-4 was confirmed by observing the mass number m/z = 447 as a molecular ion peak.

(Synthesis of Compound A17)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-4 8.00 g (17.9 mmol), Pd(dba) ₂ 0.31 g (0.03 equiv, 0.5 mmol), NaOtBu 3.44 g (2.0 equiv, 35.7 mmol), Toluene 89 mL, 3-bromo-9-phenyl-9 H-carbazole 6.33 g (1.1 equiv, 19.7 mmol) and tBu ₃ P 0.36 g (0.1 equiv, 1.8 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A17 (9.23 g, yield 75%). . FAB-MS was measured, and a mass number m/z = 688 was observed as a molecular ion peak to confirm Compound A17.

3. Synthesis of Compound B13

Compound B13, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-5)

In an Ar atmosphere, in a 1 L 3-neck flask, 7-bromo-2-iodonaphthalene 25.00 g (75.1 mmol), phenylboronic acid 10.07 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.13 g (3.0 equiv, 225.2 mmol) ), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-5 (15.31 g, yield 72%) was performed. Got it. FAB-MS was measured, and the intermediate IM-5 was confirmed by observing the mass number m/z = 283 as a molecular ion peak.

(Synthesis of intermediate IM-6)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-5 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-6 (11.27 g, yield 78%) was performed. Got it. FAB-MS was measured, and the intermediate IM-6 was confirmed by observing the mass number m/z = 314 as a molecular ion peak.

(Synthesis of intermediate IM-7)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-6 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-(naphthalen-2-yl)aniline 7.66 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-7 (12.65 g, yield 80%) Got it. FAB-MS was measured, and the compound IM-7 was confirmed by observing the mass number m/z = 497 as a molecular ion peak.

(Synthesis of Compound B13)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-7 8.00 g (16.1 mmol), Pd(dba) ₂ 0.27 g (0.03 equiv, 0.5 mmol), NaOtBu 3.09 g (2.0 equiv, 32.2 mmol), Toluene 80 mL, 1-bromo-4-triphenylsilylbenzene 7.35 g (1.1 equiv, 17.7 mmol) and tBu ₃ P 0.33 g (0.1 equiv, 1.6 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B13 (9.90 g, yield 74%). . FAB-MS was measured, and a mass number m/z = 832 was observed as a molecular ion peak to confirm compound B13.

4. Synthesis of Compound B20

Compound B20, which is a monoamine compound according to an embodiment of the present invention, may be synthesized by, for example, the following reaction.

(Synthesis of intermediate IM-8)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-6 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, aniline 3.25 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-8 (8.38 g, yield 71%) Got it. FAB-MS was measured, and the compound IM-8 was confirmed by observing the mass number m/z = 371 as a molecular ion peak.

(Synthesis of Compound B20)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-8 8.00 g (21.5 mmol), Pd(dba) ₂ 0.37 g (0.03 equiv, 0.6 mmol), NaOtBu 4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 9-(4-bromophenyl)-9-phenyl-9 H-fluorene 9.41 g (1.1 equiv, 23.7 mmol) and tBu ₃ P 0.44 g (0.1 equiv, 2.1 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B20 (11.41 g, yield 77%). . FAB-MS was measured, and compound B20 was confirmed by observing a molecular ion peak with a mass number of m/z = 687.

5. Synthesis of Compound B40

Compound B40, which is a monoamine compound according to an embodiment of the present invention, may be synthesized by, for example, the following reaction.

(Synthesis of Compound B40)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-8 8.00 g (21.5 mmol), Pd(dba) ₂ 0.37 g (0.03 equiv, 0.6 mmol), NaOtBu 4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 2-bromo-9,9-diphenyl-9 H-fluorene 9.41 g (1.1 equiv, 23.7 mmol) and tBu ₃ P 0.44 g (0.1 equiv, 2.1 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B40 (11.42 g, yield 75%). . FAB-MS was measured, and compound B40 was confirmed by observing a molecular ion peak with a mass number of m/z = 687.

6. Synthesis of Compound C25

Compound C25, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-9)

In an Ar atmosphere, in a 1 L 3-neck flask, 2-bromo-6-iodonaphthalene 25.00 g (75.1 mmol), 2-biphenylboronic acid 16.35 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.13 g (3.0 equiv, 225.2 mmol), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. . After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-9 (18.61 g, yield 69%) was performed. Got it. FAB-MS was measured, and the mass number m/z = 359 was observed as a molecular ion peak to confirm the intermediate IM-9.

(Synthesis of intermediate IM-10)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-9 15.00 g (41.8 mmol), 4-chlorophenylboronic acid 7.18 g (1.1 equiv, 45.9 mmol), K2CO3 17.31 g (3.0 equiv, 125.3 mmol), Pd(PPh ₃ ) ₄ 2.41 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-10 (12.24 g, yield 75%) was performed. Got it. FAB-MS was measured, and the intermediate IM-10 was confirmed by observing the mass number m/z = 390 as a molecular ion peak.

(Synthesis of Compound C25)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-10 10.00 g (25.6 mmol), Pd(dba) ₂ 0.44 g (0.03 equiv, 0.6 mmol), NaOtBu 4.92 g (2.0 equiv, 51.2 mmol), Toluene 128 mL, bis(4-biphenyl)amine 9.04 g (1.1 equiv, 28.1 mmol) and tBu ₃ P 0.52 g (0.1 equiv, 2.6 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C25 (13.83 g, yield 80%). . FAB-MS was measured, and the mass number m/z = 675 was observed as a molecular ion peak to confirm compound C25.

7. Synthesis of Compound C51

Compound C51, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-11)

In an Ar atmosphere, in a 1 L 3-neck flask, 2-bromo-6-iodonaphthalene 25.00 g (75.1 mmol), phenylboronic acid 10.07 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.13 g (3.0 equiv, 225.2 mmol) ), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-11 (15.31 g, yield 72%) was performed. Got it. FAB-MS was measured, and the intermediate IM-11 was confirmed by observing the mass number m/z = 283 as a molecular ion peak.

(Synthesis of intermediate IM-12)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-11 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO4. MgSO4 was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-12 (11.42 g, yield 79%) was obtained. Got it.

FAB-MS was measured, and the intermediate IM-12 was confirmed by observing the mass number m/z = 314 as a molecular ion peak.

(Synthesis of Compound C51)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-12 8.00 g (25.4 mmol), Pd(dba) ₂ 0.44 g (0.03 equiv, 0.8 mmol), NaOtBu 4.88 g (2.0 equiv, 50.8 mmol), Toluene 128 mL, N-([1,1'-biphenyl]-4-yl)dibenzothiophen-4-amine 9.82 g (1.1 equiv, 28.0 mmol) and tBu ₃ P 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added and heated Stir at reflux. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C51 (13.28 g, yield 83%). . FAB-MS was measured, and a mass number m/z = 629 was observed as a molecular ion peak to confirm compound C51.

8. Synthesis of Compound D12

Compound D12, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-13)

In an Ar atmosphere, in a 1 L 3-neck flask, 2-bromo-5-iodonaphthalene 25.00 g (75.1 mmol), phenylboronic acid 10.07 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.13 g (3.0 equiv, 225.2 mmol) ), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-13 (15.95 g, yield 75%) was performed. Got it.

FAB-MS was measured, and the intermediate IM-13 was confirmed by observing the mass number m/z = 283 as a molecular ion peak.

(Synthesis of intermediate IM-14)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-13 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-14 (11.71 g, yield 81%) was performed. Got it. FAB-MS was measured, and the intermediate IM-14 was confirmed by observing the mass number m/z = 314 as a molecular ion peak.

(Synthesis of Compound D12)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-14 9.35 g (2.2 equiv, 29.7 mmol), Pd(dba) ₂ 0.23 g (0.03 equiv, 0.4 mmol), NaOtBu 2.59 g (2.0 equiv, 27.0 mmol) , Toluene 67 mL, 4-fluoroaniline 1.5 g (13.5 mmol) and tBu ₃ P 0.27 g (0.1 equiv, 1.3 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D12 (7.48 g, yield 83%). .

FAB-MS was measured, and compound D12 was confirmed by observing a molecular ion peak with a mass number of m/z = 667.

9. Synthesis of Compound D22

Compound D22, which is a monoamine compound according to an embodiment of the present invention, may be synthesized by, for example, the following reaction.

(Synthesis of Compound D22)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-14 10.00 g (31.8 mmol), (4-(diphenylamino)phenyl)boronic acid 10.10 g (1.1 equiv, 34.9 mmol), K ₂ CO ₃ 13.17 g (3.0 equiv, 95.3 mmol), Pd(PPh ₃ ) ₄ 1.84 g (0.05 eq, 1.6 mmol), and 222 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added and heated at 80°C. Stirred. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D22 (10.98 g, yield 66%). .

FAB-MS was measured, and compound D22 was confirmed by observing a molecular ion peak with a mass number of m/z = 523.

10. Synthesis of Compound E3

Compound E3, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-15)

In an Ar atmosphere, in a 1 L 3-neck flask, 3-bromo-1-iodonaphthalene 25.00 g (75.1 mmol), phenylboronic acid 10.07 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.13 g (3.0 equiv, 225.2 mmol) ), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-15 (15.52 g, yield 73%) was performed. Got it.

FAB-MS was measured, and the intermediate IM-15 was confirmed by observing the mass number m/z = 283 as a molecular ion peak.

(Synthesis of intermediate IM-16)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-15 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-16 (12.57 g, yield 87%) was performed. Got it.

FAB-MS was measured, and the intermediate IM-16 was confirmed by observing the mass number m/z = 314 as a molecular ion peak.

(Synthesis of intermediate IM-17)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-16 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-17 (9.37 g, yield 70%) Got it.

FAB-MS was measured, and the compound IM-17 was confirmed by observing the mass number m/z = 421 as a molecular ion peak.

(Synthesis of Compound E3)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-17 8.00 g (19.0 mmol), Pd(dba) ₂ 0.33 g (0.03 equiv, 0.6 mmol), NaOtBu 3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 2-bromobiphenyl 4.87 g (1.1 equiv, 20.9 mmol) and tBu ₃ P 0.39 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E3 (7.40 g, yield 68%). .

FAB-MS was measured, and compound E3 was confirmed by observing a molecular ion peak with a mass number of m/z = 573.

11. Synthesis of Compound E32

Compound E32, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-18)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-15 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-18 (11.42 g, yield 79%) was performed. Got it.

FAB-MS was measured, and the intermediate IM-18 was confirmed by observing the mass number m/z = 314 as a molecular ion peak.

(Synthesis of Compound E32)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-18 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 6.11 g (2.0 equiv, 63.5 mmol), Toluene 158 mL, bis(4-(naphthalen-1-yl)phenyl)amine 14.73 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E32 (18.23 g, yield 82%). .

FAB-MS was measured, and compound E32 was confirmed by observing the mass number m/z = 699 as a molecular ion peak.

12. Synthesis of Compound F46

Compound F46, which is a monoamine compound according to an embodiment of the present invention, may be synthesized by, for example, the following reaction.

(Synthesis of intermediate IM-19)

In an Ar atmosphere, in a 1 L 3-neck flask, 2,3-dibromonaphthalene 25.00 g (87.4 mmol), phenylboronic acid 11.73 g (1.1 equiv, 96.2 mmol), K ₂ CO ₃ 36.2 g (3.0 equiv, 262.3 mmol), Pd(PPh ₃ ) ₄ 5.05 g (0.05 eq, 3.4 mmol), and 612 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-19 (19.31 g, yield 78%) was performed. Got it.

FAB-MS was measured, and the mass number m/z = 283 was observed as a molecular ion peak to confirm intermediate IM-19.

(Synthesis of intermediate IM-20)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-19 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-20 (12.00 g, yield 83%) Got it.

FAB-MS was measured, and the intermediate IM-20 was confirmed when the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-21)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-20 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-(naphthalen-1-yl)aniline 7.66 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-21 (10.31 g, yield 77%). Got it.

FAB-MS was measured, and compound IM-21 was confirmed by observing a molecular ion peak with a mass number of m/z = 421.

(Synthesis of Compound F46)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-21 8.00 g (19.0 mmol), Pd(dba) ₂ 0.33 g (0.03 equiv, 0.6 mmol), NaOtBu 3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 3-bromo-dibenzothiophen 5.49 g (1.1 equiv, 20.9 mmol) and tBu ₃ P 0.39 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F46 (11.61 g, yield 90%). .

FAB-MS was measured, and compound F46 was confirmed by observing the mass number m/z = 679 as a molecular ion peak.

13. Synthesis of Compound F53

Compound F53, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of Compound F53)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-20 8.00 g (23.4 mmol), Pd(dba) ₂ 0.40 g (0.03 equiv, 0.7 mmol), NaOtBu 4.50 g (2.0 equiv, 46.8 mmol), Toluene 117 mL, bis(dibenzothiophen-4-yl)amine 9.82 g (1.1 equiv, 25.7 mmol) and tBu ₃ P 0.47 g (0.1 equiv, 2.3 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F53 (13.44 g, yield 87%). .

FAB-MS was measured, and compound F53 was confirmed by observing the mass number m/z = 659 as a molecular ion peak.

14. Synthesis of Compound G54

Compound G54, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-22)

In an Ar atmosphere, in a 1 L 3-neck flask, 2-bromo-1-iodo-naphthalene 25.00 g (75.1 mmol), phenylboronic acid 10.07 g (1.1 equiv, 82.6 mmol), K ₂ CO ₃ 31.1 g (3.0 equiv, 225.2 mmol), Pd(PPh ₃ ) ₄ 4.34 g (0.05 eq, 3.8 mmol), and 525 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. . After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-22 (16.16 g, yield 76%) was performed. Got it.

FAB-MS was measured, and the intermediate IM-22 was confirmed by observing the mass number m/z = 283 as a molecular ion peak.

(Synthesis of intermediate IM-23)

In an Ar atmosphere, in a 1 L 3-neck flask, IM-22 13.00 g (45.9 mmol), 4-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H ₂ O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, the organic layer was washed with saturated brine, and then dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and the intermediate IM-23 (10.55 g, yield 73%) was performed. Got it.

FAB-MS was measured, and the intermediate IM-23 was confirmed when the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of compound G54)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-23 8.00 g (25.4 mmol), Pd(dba) ₂ 0.44 g (0.03 equiv, 0.8 mmol), NaOtBu 4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, bis(dibenzofuran-3-yl)amine 9.77 g (1.1 equiv, 28.0 mmol) and tBu ₃ P 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G54 (14.4 g, yield 90%). .

FAB-MS was measured, and compound G54 was confirmed by observing a molecular ion peak with a mass number m/z = 627.

15. Synthesis of Compound G58

Compound G58, which is a monoamine compound according to an embodiment of the present invention, may be synthesized, for example, by the following reaction.

(Synthesis of intermediate IM-24)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-23 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, aniline 3.25 g (1.1 equiv, 34.9 mmol) and tBu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ filtration and concentration of the organic layer were performed, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer), and compound IM-24 (9.56 g, yield 81%) Got it.

FAB-MS was measured, and the compound IM-24 was confirmed by observing the mass number m/z = 371 as a molecular ion peak.

(Synthesis of Compound G58)

In an Ar atmosphere, in a 300 mL 3-neck flask, IM-24 8.00 g (21.5 mmol), Pd(dba) ₂ 0.37 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9'-spirobifluorene 9.36 g (1.1 equiv, 23.7 mmol) and ^t Bu ₃ P 0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO ₄ . MgSO ₄ was filtered and the organic layer was concentrated, and the obtained crude product was purified by silica gel column chromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G58 (10.63 g, yield 72%). .

FAB-MS was measured, and a mass number m/z = 685 was observed as a molecular ion peak to confirm compound G58.

16. Synthesis of Compound A61

(Synthesis of Compound A61 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 8.00 g (25.4 mmol), Pd(dba) ₂ 044 g (0.03 equiv, 0.8 mmol), NaO ^t Bu 4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and ^t Bu ₃ P 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A61 (10.86 g, yield 78%).

FAB-MS was measured, and compound A61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

17. Synthesis of Compound A62

(Synthesis of intermediate IM-25 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-25 (10.71 g, yield 80%).

FAB-MS was measured, and the compound IM-25 was confirmed as the mass number m/z =421 was observed as a molecular ion peak.

(Synthesis of Compound A62 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-25 8.00 g (19.0 mmol), Pd(dba) ₂ 0.33 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and ^t Bu ₃ P 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A62 (10.06 g, yield 85%).

FAB-MS was measured, and compound A62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

18. Synthesis of Compound A63

(Synthesis of intermediate IM-26 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, aniline 3.25 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-26 (8.97 g, yield 76%).

FAB-MS was measured, and the compound IM-26 was confirmed as the mass number m/z = 371 was observed as a molecular ion peak.

(Synthesis of Compound A63 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-26 8.00 g (21.5 mmol), Pd(dba) ₂ 0.37 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9 H- fluorene 9.41 g (1.1 equiv, 23.7 mmol) and ^t Bu ₃ P 0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A63 (10.96 g, yield 74%).

FAB-MS was measured, and compound A63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

19. Synthesis of Compound A64

(Synthesis of intermediate IM-27 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-27 (11.68 g, yield 77%).

FAB-MS was measured, and compound IM-27 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound A64 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A64 (9.81 g, yield 83%).

FAB-MS was measured, and Compound A64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

20. Synthesis of Compound A65

(Synthesis of Compound A65 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A65 (9.34 g, yield 79%).

FAB-MS was measured, and compound A65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

21. Synthesis of Compound A66

(Synthesis of Compound A66 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A66 (8.04 g, yield 68%).

FAB-MS was measured, and compound A66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

22. Synthesis of Compound A67

(Synthesis of Compound A67 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A67 (9.22 g, yield 81%).

FAB-MS was measured, and compound A67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

23. Synthesis of Compound A68

(Synthesis of Compound A68 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A68 (9.79 g, yield 86%).

FAB-MS was measured, and compound A68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

24. Synthesis of Compound A69

(Synthesis of Compound A69 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A69 (9.34 g, yield 82%).

FAB-MS was measured, and compound A69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

25. Synthesis of Compound A70

(Synthesis of Compound A70 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A70 (8.88 g, yield 78%).

FAB-MS was measured, and compound A70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

26. Synthesis of Compound A71

(Synthesis of Compound A71 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(2-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A71 (7.52 g, yield 66%).

FAB-MS was measured, and compound A70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

27. Synthesis of Compound A72

(Synthesis of intermediate IM-28 )

In an Ar atmosphere, in a 1L three-necked flask, IM-1 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H2O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-28 (11.56 g, yield 80%).

FAB-MS was measured, and the intermediate IM-28 was confirmed as the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-29 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-29 (11.38 g, yield 75%).

FAB-MS was measured, and the compound IM-29 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound A72 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-29 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A72 (9.68 g, yield 85%).

FAB-MS was measured, and compound A72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

28. Synthesis of Compound A73

(Synthesis of Compound A73 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the developing layer) to obtain Compound A73 (9.34 g, yield 79%).

FAB-MS was measured, and compound A73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

29. Synthesis of Compound A77

(Synthesis of intermediate IM-30 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-(naphthalen-1-yl)aniline 7.66 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-30 (13.28 g, yield 84%).

FAB-MS was measured, and the compound IM-30 was confirmed as the mass number m/z = 497 was observed as a molecular ion peak.

(Synthesis of Compound A77 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-30 8.00 g (16.1 mmol), Pd(dba) ₂ 0.28 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.09 g (2.0 equiv, 32.2 mmol), Toluene 80 mL, 4-bromo-6-phenyldibenzothiophene 6.00 g (1.1 equiv, 17.7 mmol) and ^t Bu ₃ P 0.33 g (0.1 equiv, 1.6 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A77 (9.72 g, yield 80%).

FAB-MS was measured, and compound A77 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

30. Synthesis of Compound A78

(Synthesis of intermediate IM-31 )

In an Ar atmosphere, in a 1000 mL three-necked flask, [1,1'-biphenyl]-4-ol 15.00 g (80.1 mmol), 1,3-dibromo-2-fluorobenzene 24.61 g (1.1 equiv, 96.9 mmol), Cs ₂ C0 ₃ 114.85 g (4.0 equiv, 352.5 mmol), and DMF 440 mL were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-31 (29.56 g, yield 83%).

FAB-MS was measured, and the intermediate IM-31 was confirmed as the mass number m/z = 404 was observed as a molecular ion peak.

(Synthesis of intermediate IM-32 )

In an Ar atmosphere, in a 1000 mL three-necked flask, IM-31 15.00 g (37.1 mmol), Pd(PPh3)4 2.14 g (0.05 equiv, 1.9 mmol), KOAc 5.46 g (1.5 equiv, 55.7 mmol), and AcNMe2 149 mL It added sequentially, and it heated and refluxed and stirred. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the developing layer) to obtain an intermediate IM-32 (9.24 g, yield 77%).

FAB-MS was measured, and the intermediate IM-32 was confirmed as the mass number m/z = 323 was observed as a molecular ion peak.

(Synthesis of Compound A78 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-30 8.00 g (16.1 mmol), Pd(dba) ₂ 0.28 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.09 g (2.0 equiv, 32.2 mmol), Toluene 80 mL, IM-32 5.72 g (1.1 equiv, 17.7 mmol) and ^t Bu ₃ P 0.33 g (0.1 equiv, 1.6 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A78 (9.87 g, yield 83%).

FAB-MS was measured, and compound A78 was confirmed as the mass number m/z = 739 was observed as a molecular ion peak.

31. Synthesis of Compound A79

(Synthesis of Compound A79 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba) ₂ 0.87 g (0.06 equiv, 1.5 mmol), NaO ^t Bu 7.23 g (4.0 equiv, 75.3 mmol) , Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and ^t Bu ₃ P 1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A79 (14.23 g, yield 75%).

FAB-MS was measured, and compound A79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

32. Synthesis of Compound A81

(Synthesis of Compound A81)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A81 (7.44 g, yield 69%).

FAB-MS was measured, and compound A81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

33. Synthesis of Compound A82

(Synthesis of Compound A82)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A82 (8.20 g, yield 76%).

FAB-MS was measured, and compound A82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

34. Synthesis of Compound A86

(Synthesis of intermediate IM-33)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-33 (11.88 g, yield 81%).

FAB-MS was measured, and compound IM-33 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of Compound A86)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A86 (10.16 g, yield 85%).

FAB-MS was measured, and compound A86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

35. Synthesis of Compound A87

(Synthesis of Compound A87)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A87 (9.21 g, yield 77%).

FAB-MS was measured, and compound A87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

36. Synthesis of Compound A88

(Synthesis of Compound A88)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the developing layer) to obtain Compound A88 (8.49 g, yield 71%).

FAB-MS was measured, and compound A88 was confirmed as a mass number m/z = 689 was observed as a molecular ion peak.

37. Synthesis of Compound A89

(Synthesis of Compound A89)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A89 (10.01 g, yield 87%).

FAB-MS was measured, and compound A89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

38. Synthesis of Compound A90

(Synthesis of Compound A90)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A90 (9.32 g, yield 81%).

FAB-MS was measured, and compound A90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

39. Synthesis of Compound A91

(Synthesis of Compound A91)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A91 (8.98 g, yield 78%).

FAB-MS was measured, and compound A91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

40. Synthesis of Compound A92

(Synthesis of Compound A92)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A92 (9.69 g, yield 81%).

FAB-MS was measured, and compound A92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

41. Synthesis of Compound A93

(Synthesis of Compound A93)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-33 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A93 (9.80 g, 82% yield).

FAB-MS was measured, and compound A93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

42. Synthesis of Compound A96

(Synthesis of intermediate IM-34)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-34 (12.59 g, yield 83%).

FAB-MS was measured, and compound IM-34 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound A96)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A96 (9.23 g, yield 83%).

FAB-MS was measured, and compound A96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

43. Synthesis of Compound A97

(Synthesis of Compound A97)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A97 (9.34 g, yield 79%).

FAB-MS was measured, and compound A97 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

44. Synthesis of Compound A98

(Synthesis of Compound A98)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A98 (8.16 g, yield 69%).

FAB-MS was measured, and compound A98 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

45. Synthesis of Compound A99

(Synthesis of Compound A99)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A99 (9.45 g, yield 83%).

FAB-MS was measured, and compound A99 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

46. Synthesis of Compound A100

(Synthesis of Compound A100)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A100 (9.79 g, yield 86%).

FAB-MS was measured, and compound A100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

47. Synthesis of Compound A101

(Synthesis of Compound A101)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 9-(4-bromophenyl)phenanthrene 6.14 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A101 (9.54 g, yield 78%).

FAB-MS was measured, and compound A101 was confirmed as the mass number m/z = 729 was observed as a molecular ion peak.

48. Synthesis of Compound A102

(Synthesis of Compound A102)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A102 (8.43 g, yield 74%).

FAB-MS was measured, and compound A102 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

49. Synthesis of Compound A103

(Synthesis of Compound A103)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-34 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the developing layer) to obtain Compound A103 (9.46 g, yield 80%).

FAB-MS was measured, and compound A103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

50. Synthesis of Compound A53

(Synthesis of Compound A53)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-27 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound A53 (9.17 g, yield 83%).

FAB-MS was measured, and compound A53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

51. Synthesis of Compound B61

(Synthesis of Compound B61)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-6 8.00 g (25.4 mmol), Pd(dba)2 044 g (0.03 equiv, 0.8 mmol), NaOtBu　4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, Bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and tBu3P　 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B61 (11.41 g, yield 82%).

FAB-MS was measured, and compound B61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

52. Synthesis of Compound B62

(Synthesis of intermediate IM-35)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-6 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and tBu3P　0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-35 (11.11 g, yield 83%).

FAB-MS was measured, and the compound IM-35 was confirmed as the mass number m/z =421 was observed as a molecular ion peak.

(Synthesis of Compound B62)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-35 8.00 g (19.0 mmol), Pd(dba)2 0.33 g (0.03 equiv, 0.6 mmol), NaOtBu　3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and tBu3P　 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B62 (9.35 g, yield 79%).

FAB-MS was measured, and compound B62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

53. Synthesis of Compound B63

(Synthesis of Compound B63)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-8 8.00 g (21.5 mmol), Pd(dba)2 0.37 g (0.03 equiv, 0.6 mmol), NaOtBu　4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9H-fluorene 9.41 g (1.1 equiv, 23.7 mmol) and tBu3P　0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B63 (10.64 g, yield 73%).

FAB-MS was measured, and compound B63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

54. Synthesis of Compound B64

(Synthesis of intermediate IM-36)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-6 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-36 (11.83 g, yield 78%).

FAB-MS was measured, and compound IM-36 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound B64)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B64 (10.05 g, yield 85%).

FAB-MS was measured, and compound B64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

55. Synthesis of Compound B65

(Synthesis of Compound B65)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B65 (9.58 g, yield 81%).

FAB-MS was measured, and compound B65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

56. Synthesis of Compound B66

(Synthesis of Compound B66)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B66 (8.99 g, yield 76%).

FAB-MS was measured, and compound B66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

57. Synthesis of Compound B67

(Synthesis of Compound B67)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B67 (9.57 g, yield 84%).

FAB-MS was measured, and compound B67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

58. Synthesis of Compound B68

(Synthesis of Compound B68)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B68 (9.68 g, yield 85%).

FAB-MS was measured, and compound B68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

59. Synthesis of Compound B69

(Synthesis of Compound B69)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B69 (9.68 g, yield 85%).

FAB-MS was measured, and compound B69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

60. Synthesis of Compound B70

(Synthesis of Compound B70)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B70 (9.45 g, yield 83%).

FAB-MS was measured, and compound B70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

61. Synthesis of Compound B72

(Synthesis of intermediate IM-37)

In an Ar atmosphere, in a 1L three-necked flask, IM-5 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 　7.90 g (1.1 equiv, 50.5 mmol), K2CO3 　 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh3)4 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H2O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-37 (12.00 g, yield 83%).

FAB-MS was measured, and the intermediate IM-37 was confirmed as the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-38)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-37 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-38 (11.68 g, yield 77%).

FAB-MS was measured, and the compound IM-38 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound B72)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B72 (9.11 g, yield 85%).

FAB-MS was measured, and compound B72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

62. Synthesis of Compound B73

(Synthesis of Compound B73)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B73 (9.58 g, yield 81%).

FAB-MS was measured, and compound B73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

63. Synthesis of Compound B79

(Synthesis of Compound B79)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-6 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba)2 0.87 g (0.06 equiv, 1.5 mmol), NaOtBu　7.23 g (4.0 equiv, 75.3 mmol), Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and tBu3P?1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B79 (15.17 g, yield 80%).

FAB-MS was measured, and compound B79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

64. Synthesis of Compound B81

(Synthesis of Compound B81)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B81 (8.20 g, yield 76%).

FAB-MS was measured, and compound B81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

65. Synthesis of Compound B82

(Synthesis of Compound B82)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B82 (8.84 g, yield 82%).

FAB-MS was measured, and compound B82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

66. Synthesis of Compound B86

(Synthesis of intermediate IM-38)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-6 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-38 (11.58 g, yield 79%).

FAB-MS was measured, and compound IM-38 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of Compound B86)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B86 (10.14 g, yield 84%).

FAB-MS was measured, and compound B86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

67. Synthesis of Compound B87

(Synthesis of Compound B87)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B87 (8.85 g, yield 74%).

FAB-MS was measured, and compound B87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

68. Synthesis of Compound B89

(Synthesis of Compound B89)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B89 (9.66 g, yield 84%).

FAB-MS was measured, and compound B89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

69. Synthesis of Compound B90

(Synthesis of Compound B90)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B90 (9.09 g, yield 79%).

FAB-MS was measured, and compound B90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

70. Synthesis of Compound B91

(Synthesis of Compound B91)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B91 (10.15 g, yield 78%).

FAB-MS was measured, and compound B91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

71. Synthesis of Compound B92

(Synthesis of Compound B92)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B92 (9.20 g, yield 80%).

FAB-MS was measured, and compound B92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

72. Synthesis of Compound B93

(Synthesis of Compound B93)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-38 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B93 (10.16 g, yield 85%).

FAB-MS was measured, and compound B93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

73. Synthesis of Compound B96

(Synthesis of intermediate IM-39)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-6 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-39 (12.90 g, yield 85%).

FAB-MS was measured, and the compound IM-39 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound B96)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-39 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound B96 (10.05 g, yield 85%).

FAB-MS was measured, and compound B96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

74. Synthesis of Compound B100

(Synthesis of Compound B100)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-39 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B100 (9.68 g, yield 85%).

FAB-MS was measured, and compound B100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

75. Synthesis of Compound B103

(Synthesis of Compound B103)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-39 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B103 (9.93 g, yield 84%).

FAB-MS was measured, and compound B103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

76. Synthesis of Compound B53

(Synthesis of Compound B53)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-36 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound B53 (9.50 g, yield 86%).

FAB-MS was measured, and compound B53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

77. Synthesis of Compound C61

(Synthesis of Compound C61)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 8.00 g (25.4 mmol), Pd(dba)2 044 g (0.03 equiv, 0.8 mmol), NaOtBu　4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, Bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and tBu3P　 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C61 (11.13 g, yield 80%).

FAB-MS was measured, and compound C61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

78. Synthesis of Compound C62

(Synthesis of intermediate IM-40)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and tBu3P　0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain a compound IM-40 (10.85 g, yield 81%).

FAB-MS was measured, and the compound IM-40 was confirmed as the mass number m/z =421 was observed as a molecular ion peak.

(Synthesis of Compound C62)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-40 8.00 g (19.0 mmol), Pd(dba)2 0.33 g (0.03 equiv, 0.6 mmol), NaOtBu　3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and tBu3P　 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C62 (9.59 g, yield 81%).

FAB-MS was measured, and compound C62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

79. Synthesis of Compound C63

(Synthesis of intermediate IM-41)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 3.25 g (1.1 equiv, 34.9 mmol) of aniline and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-41 (9.68 g, yield 82%).

FAB-MS was measured, and compound IM-41 was confirmed as the mass number m/z = 371 was observed as a molecular ion peak.

(Synthesis of Compound C63)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-41 8.00 g (21.5 mmol), Pd(dba)2 0.37 g (0.03 equiv, 0.6 mmol), NaOtBu　4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9H-fluorene 9.41 g (1.1 equiv, 23.7 mmol) and tBu3P　0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used for the development layer) to obtain compound C63 (11.08 g, yield 76%).

FAB-MS was measured, and compound C63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

80. Synthesis of Compound C64

(Synthesis of intermediate IM-42)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-42 (11.83 g, yield 78%).

FAB-MS was measured, and the compound IM-42 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound C64)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C64 (9.93 g, yield 85%).

FAB-MS was measured, and compound C64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

81. Synthesis of Compound C65

(Synthesis of Compound C65)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C65 (9.34 g, yield 79%).

FAB-MS was measured, and compound C65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

82. Synthesis of Compound C66

(Synthesis of Compound C66)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C66 (9.10 g, yield 77%).

FAB-MS was measured, and compound C66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

83. Synthesis of Compound C67

(Synthesis of Compound C67)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C67 (9.00 g, yield 79%).

FAB-MS was measured, and compound C67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

84. Synthesis of Compound C68

(Synthesis of Compound C68)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C68 (9.22 g, yield 81%).

FAB-MS was measured, and compound C68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

85. Synthesis of Compound C69

(Synthesis of Compound C69)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C69 (9.34 g, yield 82%).

FAB-MS was measured, and compound C69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

86. Synthesis of Compound C70

(Synthesis of Compound C70)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C70 (9.57 g, yield 83%).

FAB-MS was measured, and compound C70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

87. Synthesis of Compound C72

(Synthesis of intermediate IM-43)

In an Ar atmosphere, in a 1L three-necked flask, IM-11 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 　7.90 g (1.1 equiv, 50.5 mmol), K2CO3 　 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh3)4 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H2O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-43 (11.56 g, yield 80%).

FAB-MS was measured, and the intermediate IM-43 was confirmed as the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-44)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-43 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-44 (12.29 g, yield 81%).

FAB-MS was measured, and the compound IM-44 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound C72)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-44 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C72 (9.68 g, yield 85%).

FAB-MS was measured, and compound C72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

88. Synthesis of Compound C73

(Synthesis of Compound C73)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C73 (9.34 g, yield 79%).

FAB-MS was measured, and compound C73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

89. Synthesis of Compound C79

(Synthesis of Compound C79)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba)2 0.87 g (0.06 equiv, 1.5 mmol), NaOtBu　7.23 g (4.0 equiv, 75.3 mmol), Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and tBu3P?1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C79 (15.74 g, yield 83%).

FAB-MS was measured, and compound C79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

90. Synthesis of Compound C81

(Synthesis of Compound C81)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C81 (8.41 g, yield 78%).

FAB-MS was measured, and compound C81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

91. Synthesis of Compound C82

(Synthesis of Compound C82)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C82 (9.17 g, yield 85%).

FAB-MS was measured, and compound C82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

92. Synthesis of Compound C86

(Synthesis of intermediate IM-45)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-45 (11.88 g, yield 81%).

FAB-MS was measured, and compound IM-45 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of Compound C86)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C86 (10.28 g, yield 86%).

FAB-MS was measured, and compound C86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

93. Synthesis of Compound C87

(Synthesis of Compound C87)

Under Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C87 (9.09 g, yield 76%).

FAB-MS was measured, and compound C87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

94. Synthesis of Compound C89

(Synthesis of Compound C89)

Under Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C89 (9.55 g, yield 83%).

FAB-MS was measured, and compound C89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

95. Synthesis of Compound C90

(Synthesis of Compound C90)

Under Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C90 (9.66 g, yield 84%).

FAB-MS was measured, and compound C90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

96. Synthesis of Compound C91

(Synthesis of Compound C91)

Under Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C91 (9.90 g, yield 80%).

FAB-MS was measured, and compound C91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

97. Synthesis of Compound C92

(Synthesis of Compound C92)

Under Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C92 (9.66 g, yield 84%).

FAB-MS was measured, and compound C92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

98. Synthesis of Compound C93

(Synthesis of Compound C93)

Under Ar atmosphere, in a 300 mL three-necked flask, IM-45 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C93 (9.80 g, yield 82%).

FAB-MS was measured, and compound C93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

99. Synthesis of Compound C96

(Synthesis of intermediate IM-46)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-12 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-46 (12.29 g, yield 85%).

FAB-MS was measured, and the compound IM-46 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound C96)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-46 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used for the development layer) to obtain compound C96 (9.93 g, yield 84%).

FAB-MS was measured, and compound C96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

100. Synthesis of Compound C100

(Synthesis of Compound C100)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-46 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C100 (9.91 g, yield 87%).

FAB-MS was measured, and compound C100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

101. Synthesis of Compound C103

(Synthesis of Compound C103)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-46 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C103 (10.17 g, yield 86%).

FAB-MS was measured, and compound C103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

102. Synthesis of Compound C53

(Synthesis of Compound C53)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-42 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound C53 (8.95 g, 　 yield 81%).

FAB-MS was measured, and compound C53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

103. Synthesis of Compound D61

(Synthesis of Compound D61)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 8.00 g (25.4 mmol), Pd(dba)2 044 g (0.03 equiv, 0.8 mmol), NaOtBu　4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, Bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and tBu3P　 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D61 (11.41 g, yield 80%).

FAB-MS was measured, and compound D61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

104. Synthesis of Compound D62

(Synthesis of intermediate IM-47)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and tBu3P　0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-47 (10.44 g, yield 78%).

FAB-MS was measured, and compound IM-47 was confirmed as the mass number m/z =421 was observed as a molecular ion peak.

(Synthesis of Compound D62)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-47 8.00 g (19.0 mmol), Pd(dba)2 0.33 g (0.03 equiv, 0.6 mmol), NaOtBu　3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and tBu3P　 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the developing layer) to obtain Compound D62 (8.88 g, yield 75%).

FAB-MS was measured, and compound D62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

105. Synthesis of Compound D63

(Synthesis of intermediate IM-48)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 3.25 g (1.1 equiv, 34.9 mmol) of aniline and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-48 (9.44 g, yield 80%).

FAB-MS was measured, and the compound IM-48 was confirmed as the mass number m/z = 371 was observed as a molecular ion peak.

(Synthesis of Compound D63)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-48 8.00 g (21.5 mmol), Pd(dba)2 0.37 g (0.03 equiv, 0.6 mmol), NaOtBu　4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9H-fluorene 9.41 g (1.1 equiv, 23.7 mmol) and tBu3P　0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D63 (11.23 g, yield 77%).

FAB-MS was measured, and compound D63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

106. Synthesis of Compound D64

(Synthesis of intermediate IM-49)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-49 (11.53 g, yield 76%).

FAB-MS was measured, and the compound IM-49 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound D64)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D64 (9.58 g, yield 81%).

FAB-MS was measured, and compound D64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

107. Synthesis of Compound D65

(Synthesis of Compound D65)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D65 (9.46 g, yield 80%).

FAB-MS was measured, and compound D65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

108. Synthesis of Compound D66

(Synthesis of Compound D66)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D66 (8.75 g, yield 74%).

FAB-MS was measured, and compound D66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

109. Synthesis of Compound D67

(Synthesis of Compound D67)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D67 (9.34 g, yield 82%).

FAB-MS was measured, and compound D67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

110. Synthesis of Compound D68

(Synthesis of Compound D68)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D68 (9.57 g, yield 81%).

FAB-MS was measured, and compound D68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

111. Synthesis of Compound D69

(Synthesis of Compound D69)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D69 (9.57 g, yield 84%).

FAB-MS was measured, and compound D69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

112. Synthesis of Compound D70

(Synthesis of Compound D70)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D70 (9.34 g, yield 82%).

FAB-MS was measured, and compound D70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

113. Synthesis of Compound D72

(Synthesis of intermediate IM-50)

In an Ar atmosphere, in a 1L three-necked flask, IM-13 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 　7.90 g (1.1 equiv, 50.5 mmol), K2CO3 　19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh3)4 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H2O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-50 (11.71 g, yield 81%).

FAB-MS was measured, and the intermediate IM-50 was confirmed as the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-51)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-50 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-51 (12.14 g, yield 80%).

FAB-MS was measured, and the compound IM-51 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound D72)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-51 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D72 (9.34 g, yield 82%).

FAB-MS was measured, and compound D72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

114. Synthesis of Compound D73

(Synthesis of Compound D73)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D73 (9.93 g, yield 84%).

FAB-MS was measured, and compound D73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

115. Synthesis of Compound D79

(Synthesis of Compound D79)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba)2 0.87 g (0.06 equiv, 1.5 mmol), NaOtBu　7.23 g (4.0 equiv, 75.3 mmol), Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and tBu3P?1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D79 (14.80 g, yield 78%).

FAB-MS was measured, and compound D79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

116. Synthesis of Compound D81

(Synthesis of Compound D81)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D81 (7.87 g, yield 73%).

FAB-MS was measured, and compound D81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

117. Synthesis of Compound D82

(Synthesis of Compound D82)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D82 (8.84 g, yield 82%).

FAB-MS was measured, and compound D82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

118. Synthesis of Compound D86

(Synthesis of intermediate IM-52)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-52 (11.73 g, yield 80%).

FAB-MS was measured, and the compound IM-52 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of Compound D86)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound D86 (9.80 g, yield 82%).

FAB-MS was measured, and compound D86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

119. Synthesis of Compound D87

(Synthesis of Compound D87)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D87 (9.57 g, yield 80%).

FAB-MS was measured, and compound D87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

120. Synthesis of Compound D89

(Synthesis of Compound D89)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D89 (9.89 g, yield 86%).

FAB-MS was measured, and compound D89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

121. Synthesis of Compound D90

(Synthesis of Compound D90)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D90 (9.09 g, yield 79%).

FAB-MS was measured, and compound D90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

122. Synthesis of Compound D91

(Synthesis of Compound D91)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D91 (9.77 g, yield 79%).

FAB-MS was measured, and compound D91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

123. Synthesis of Compound D92

(Synthesis of Compound D92)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D92 (9.66 g, yield 84%).

FAB-MS was measured, and compound D92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

124. Synthesis of Compound D93

(Synthesis of Compound D93)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-52 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D93 (9.57 g, yield 80%).

FAB-MS was measured, and compound D93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

125. Synthesis of Compound D96

(Synthesis of intermediate IM-53)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-14 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-53 (12.14 g, yield 80%).

FAB-MS was measured, and the compound IM-53 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound D96)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-53 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D96 (9.46 g, yield 80%).

FAB-MS was measured, and compound D96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

126. Synthesis of Compound D100

(Synthesis of Compound D100)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-53 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D100 (8.88 g, yield 78%).

FAB-MS was measured, and compound D100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

127. Synthesis of Compound D103

(Synthesis of Compound D103)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-53 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D103 (9.22 g, yield 78%).

FAB-MS was measured, and compound D103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

128. Synthesis of Compound D53

(Synthesis of Compound C53)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-49 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound D53 (9.39 g, 　 yield 85%).

FAB-MS was measured, and compound D53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

129. Synthesis of Compound E61

(Synthesis of Compound E61)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-16 8.00 g (25.4 mmol), Pd(dba)2 044 g (0.03 equiv, 0.8 mmol), NaOtBu　4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, Bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and tBu3P　 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E61 (11.00 g, yield 79%).

FAB-MS was measured, and compound E61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

130. Synthesis of Compound E62

(Synthesis of compound E62)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-17 8.00 g (19.0 mmol), Pd(dba)2 0.33 g (0.03 equiv, 0.6 mmol), NaOtBu　3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and tBu3P　 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E62 (9.00 g, yield 76%).

FAB-MS was measured, and compound E62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

131. Synthesis of Compound E63

(Synthesis of intermediate IM-54)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-16 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 3.25 g (1.1 equiv, 34.9 mmol) of aniline and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-54 (8.97 g, yield 76%).

FAB-MS was measured, and the compound IM-54 was confirmed as the mass number m/z = 371 was observed as a molecular ion peak.

(Synthesis of compound E63)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-54 8.00 g (21.5 mmol), Pd(dba)2 0.37 g (0.03 equiv, 0.6 mmol), NaOtBu　4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9H-fluorene 9.41 g (1.1 equiv, 23.7 mmol) and tBu3P　0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E63 (11.37 g, yield 78%).

FAB-MS was measured, and compound E63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

132. Synthesis of Compound E64

(Synthesis of intermediate IM-55)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-16 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-55 (11.68 g, yield 77%).

FAB-MS was measured, and the compound IM-55 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound E64)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E64 (9.46 g, yield 80%).

FAB-MS was measured, and compound E64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

133. Synthesis of Compound E65

(Synthesis of compound E65)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E65 (8.99 g, yield 80%).

FAB-MS was measured, and compound E65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

134. Synthesis of Compound E66

(Synthesis of Compound E66)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E66 (8.28 g, yield 74%).

FAB-MS was measured, and compound E66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

135. Synthesis of Compound E67

(Synthesis of Compound E67)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E67 (8.65 g, yield 76%).

FAB-MS was measured, and compound E67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

136. Synthesis of Compound E68

(Synthesis of Compound E68)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E68 (9.79 g, yield 86%).

FAB-MS was measured, and compound E68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

137. Synthesis of Compound E69

(Synthesis of Compound E69)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E69 (9.79 g, yield 86%).

FAB-MS was measured, and compound E69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

138. Synthesis of Compound E70

(Synthesis of Compound E70)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound E70 (9.57 g, yield 84%).

FAB-MS was measured, and compound E70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

139. Synthesis of Compound E72

(Synthesis of intermediate IM-56)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-18 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 6.96 g (1.1 equiv, 34.9 mmol) of 4-aminodibenzothiophene and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P　 were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-56 (11.83 g, yield 78%).

FAB-MS was measured, and the compound IM-56 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound E72)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-56 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E72 (9.00 g, yield 79%).

FAB-MS was measured, and compound E72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

140. Synthesis of Compound E73

(Synthesis of Compound E73)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E73 (8.99 g, yield 76%).

FAB-MS was measured, and compound E73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

141. Synthesis of Compound E79

(Synthesis of Compound E79)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-16 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba)2 0.87 g (0.06 equiv, 1.5 mmol), NaOtBu　7.23 g (4.0 equiv, 75.3 mmol), Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and tBu3P?1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E79 (13.66 g, yield 72%).

FAB-MS was measured, and compound E79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

142. Synthesis of Compound E81

(Synthesis of Compound E81)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E81 (8.20 g, yield 76%).

FAB-MS was measured, and compound E81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

143. Synthesis of Compound E82

(Synthesis of Compound E82)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba)2 0.29 g (0.03 equiv, 0.5 mmol), NaOtBu　3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and tBu3P　 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E82 (9.27 g, yield 86%).

FAB-MS was measured, and compound E82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

144. Synthesis of Compound E86

(Synthesis of intermediate IM-57)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-16 10.00 g (31.8 mmol), Pd(dba)2 0.55 g (0.03 equiv, 1.0 mmol), NaOtBu　3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and tBu3P　 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-57 (11.14 g, yield 76%).

FAB-MS was measured, and compound IM-57 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of compound E86)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E86 (9.57 g, yield 80%).

FAB-MS was measured, and compound E86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

145. Synthesis of Compound E87

(Synthesis of Compound E87)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E87 (8.97 g, yield 75%).

FAB-MS was measured, and compound E87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

146. Synthesis of Compound E89

(Synthesis of compound E89)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E89 (9.32 g, yield 81%).

FAB-MS was measured, and compound E89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

147. Synthesis of Compound E90

(Synthesis of compound E90)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound E90 (8.51 g, yield 74%).

FAB-MS was measured, and compound E90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

148. Synthesis of Compound E91

(Synthesis of Compound E91)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and tBu3P　 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E91 (9.28 g, yield 75%).

FAB-MS was measured, and compound E91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

149. Synthesis of Compound E92

(Synthesis of Compound E92)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba)2 0.30 g (0.03 equiv, 0.5 mmol), NaOtBu　3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and tBu3P　0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E92 (8.86 g, yield 77%).

FAB-MS was measured, and compound E92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

150. Synthesis of Compound E93

(Synthesis of Compound E93)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-57 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E93 (9.96 g, yield 75%).

FAB-MS was measured, and compound E93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

151. Synthesis of Compound E96

(Synthesis of intermediate IM-58 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-16 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-58 (11.68 g, yield 77%).

FAB-MS was measured, and the compound IM-58 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound E96 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-58 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E96 (9.56 g, yield 81%).

FAB-MS was measured, and compound E96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

152. Synthesis of Compound E100

(Synthesis of Compound E100 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-58 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E100 (8.43 g, yield 78%).

FAB-MS was measured, and compound E100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

153. Synthesis of Compound E103

(Synthesis of Compound E103 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-58 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E103 (8.87 g, yield 75%).

FAB-MS was measured, and compound E103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

154. Synthesis of Compound E53

(Synthesis of Compound E53 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-55 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound E53 (8.51 g, yield 77%).

FAB-MS was measured, and compound E53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

155. Synthesis of Compound F61

(Synthesis of Compound F61 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 8.00 g (25.4 mmol), Pd(dba) ₂ 044 g (0.03 equiv, 0.8 mmol), NaO ^t Bu 4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and ^t Bu ₃ P 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F61 (11.30 g, yield 74%).

FAB-MS was measured, and compound F61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

156. Synthesis of Compound F62

(Synthesis of intermediate IM-59 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-59 (10.31 g, yield 77%).

FAB-MS was measured, and the compound IM-59 was confirmed as the mass number m/z =421 was observed as a molecular ion peak.

(Synthesis of Compound F62 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-59 8.00 g (19.0 mmol), Pd(dba) ₂ 0.33 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and ^t Bu ₃ P 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F62 (9.45 g, yield 80%).

FAB-MS was measured, and compound F62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

157. Synthesis of Compound F63

(Synthesis of intermediate IM-60 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, aniline 3.25 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-60 (8.73 g, yield 74%).

FAB-MS was measured, and compound IM-60 was confirmed as the mass number m/z = 371 was observed as a molecular ion peak.

(Synthesis of Compound F63 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-60 8.00 g (21.5 mmol), Pd(dba) ₂ 0.37 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9 H- fluorene 9.41 g (1.1 equiv, 23.7 mmol) and ^t Bu ₃ P 0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F63 (10.06 g, yield 69%).

FAB-MS was measured, and compound F63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

158. Synthesis of Compound F64

(Synthesis of intermediate IM-61 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-61 (11.38 g, yield 75%).

FAB-MS was measured, and compound IM-61 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound F64 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F64 (9.10 g, yield 77%).

FAB-MS was measured, and compound F64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

159. Synthesis of Compound F65

(Synthesis of Compound F65 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F65 (8.61 g, yield 73%).

FAB-MS was measured, and compound F65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

160. Synthesis of Compound F66

(Synthesis of Compound F66 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F66 (7.92 g, yield 67%).

FAB-MS was measured, and compound F66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

161. Synthesis of Compound F67

(Synthesis of Compound F67 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F67 (8.43 g, yield 74%).

FAB-MS was measured, and compound F67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

162. Synthesis of Compound F68

(Synthesis of Compound F68 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound F68 (9.00 g, yield 79%).

FAB-MS was measured, and compound F68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

163. Synthesis of Compound F69

(Synthesis of Compound F69 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F69 (9.11 g, yield 80%).

FAB-MS was measured, and compound F69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

164. Synthesis of compound F70

(Synthesis of Compound F70 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F70 (8.77 g, yield 77%).

FAB-MS was measured, and compound F70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

165. Synthesis of Compound F72

(Synthesis of intermediate IM-62 )

In an Ar atmosphere, in a 1L three-necked flask, IM-19 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H2O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-62 (11.27 g, yield 78%).

FAB-MS was measured, and the intermediate IM-62 was confirmed as the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-63 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-62 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-63 (12.74 g, yield 80%).

FAB-MS was measured, and the compound IM-63 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound F72 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-63 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F72 (9.00 g, yield 79%).

FAB-MS was measured, and compound F72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

166. Synthesis of Compound F73

(Synthesis of Compound F73 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F73 (8.75 g, yield 74%).

FAB-MS was measured, and compound F73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

167. Synthesis of Compound F79

(Synthesis of Compound F79 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba) ₂ 0.87 g (0.06 equiv, 1.5 mmol), NaO ^t Bu 7.23 g (4.0 equiv, 75.3 mmol) , Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and ^t Bu ₃ P 1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F79 (12.90 g, yield 68%).

FAB-MS was measured, and compound F79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

168. Synthesis of Compound F81

(Synthesis of Compound F81 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F81 (7.76 g, yield 72%).

FAB-MS was measured, and compound F81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

169. Synthesis of Compound F82

(Synthesis of Compound F82 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F82 (8.73 g, yield 81%).

FAB-MS was measured, and compound F82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

170. Synthesis of Compound F86

(Synthesis of intermediate IM-64 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-64 (10.85 g, yield 74%).

FAB-MS was measured, and the compound IM-64 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of Compound F86 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F86 (9.45 g, yield 79%).

FAB-MS was measured, and compound F86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

171. Synthesis of Compound F87

(Synthesis of Compound F87 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F87 (8.73 g, yield 75%).

FAB-MS was measured, and compound F87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

172. Synthesis of Compound F89

(Synthesis of Compound F89 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F89 (8.74 g, yield 76%).

FAB-MS was measured, and compound F89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

173. Synthesis of Compound F90

(Synthesis of Compound F90 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain Compound F90 (8.17 g, yield 71%).

FAB-MS was measured, and compound F90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

174. Synthesis of Compound F91

(Synthesis of Compound F91 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F91 (8.79 g, yield 71%).

FAB-MS was measured, and compound F91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

175. Synthesis of Compound F92

(Synthesis of Compound F92 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F92 (8.40 g, yield 73%).

FAB-MS was measured, and compound F92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

176. Synthesis of Compound F93

(Synthesis of Compound F93 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-64 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F93 (8.25 g, yield 69%).

FAB-MS was measured, and compound F93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

177. Synthesis of Compound F96

(Synthesis of intermediate IM-65 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-20 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-65 (10.77 g, yield 71%).

FAB-MS was measured, and the compound IM-65 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound F96 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-65 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F96 (8.87 g, yield 75%).

FAB-MS was measured, and compound F96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

178. Synthesis of Compound F100

(Synthesis of Compound F100 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-65 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F100 (7.86, yield 69%).

FAB-MS was measured, and compound F100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

179. Synthesis of Compound F103

(Synthesis of Compound F103 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-65 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F103 (8.39 g, yield 71%).

FAB-MS was measured, and compound F103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

180. Synthesis of Compound F53

(Synthesis of Compound F53 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-61 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound F53 (8.07 g, yield 73%).

FAB-MS was measured, and compound F53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

181. Synthesis of Compound G61

(Synthesis of Compound G61 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-23 8.00 g (25.4 mmol), Pd(dba) ₂ 044 g (0.03 equiv, 0.8 mmol), NaO ^t Bu 4.88 g (2.0 equiv, 50.8 mmol), Toluene 127 mL, bis(1-naphthyl)amine 7.53 g (1.1 equiv, 28.0 mmol) and ^t Bu ₃ P 0.51 g (0.1 equiv, 2.5 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G61 (9.74 g, yield 74%).

FAB-MS was measured, and compound G61 was confirmed as the mass number m/z = 547 was observed as a molecular ion peak.

182. Synthesis of Compound G62

(Synthesis of intermediate IM-66 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-23 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-naphthylamine 5.00 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-66 (10.04 g, yield 75%).

FAB-MS was measured, and the compound IM-66 was confirmed as the mass number m/z =421 was observed as a molecular ion peak.

(Synthesis of Compound G62 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-66 8.00 g (19.0 mmol), Pd(dba) ₂ 0.33 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 3.65 g (2.0 equiv, 38.0 mmol), Toluene 95 mL, 1-(4-bromophenyl)naphthalene 5.91 g (1.1 equiv, 20.9 mmol) and ^t Bu ₃ P 0.38 g (0.1 equiv, 1.9 mmol) were sequentially added, followed by heating and refluxing and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G62 (9.59 g, yield 81%).

FAB-MS was measured, and compound G62 was confirmed as the mass number m/z = 623 was observed as a molecular ion peak.

183. Synthesis of Compound G63

(Synthesis of Compound G63 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-24 8.00 g (21.5 mmol), Pd(dba) ₂ 0.37 g (0.03 equiv, 0.6 mmol), NaO ^t Bu 4.14 g (2.0 equiv, 43.1 mmol), Toluene 108 mL, 4-bromo-9,9-diphenyl-9 H- fluorene 9.41 g (1.1 equiv, 23.7 mmol) and ^t Bu ₃ P 0.44 g (0.1 equiv, 2.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G63 (10.64 g, yield 73%).

FAB-MS was measured, and compound G63 was confirmed as the mass number m/z = 687 was observed as a molecular ion peak.

184. Synthesis of Compound G64

(Synthesis of intermediate IM-67 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-23 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-67 (11.08 g, yield 73%).

FAB-MS was measured, and compound IM-67 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound G64 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G64 (8.87 g, yield 75%).

FAB-MS was measured, and compound G64 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

185. Synthesis of Compound G65

(Synthesis of Compound G65 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G65 (8.28 g, yield 70%).

FAB-MS was measured, and compound G65 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

186. Synthesis of Compound G66

(Synthesis of compound G66 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G66 (8.16 g, yield 69%).

FAB-MS was measured, and compound G66 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

187. Synthesis of Compound G67

(Synthesis of Compound G67 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromo-4-phenylnaphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G67 (8.77 g, yield 77%).

FAB-MS was measured, and compound G67 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

188. Synthesis of Compound G68

(Synthesis of Compound G68)

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G68 (9.45 g, yield 83%).

FAB-MS was measured, and compound G68 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

189. Synthesis of Compound G69

(Synthesis of Compound G69 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G69 (9.45 g, yield 83%).

FAB-MS was measured, and compound G69 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

190. Synthesis of Compound G70

(Synthesis of Compound G70 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(3-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G70 (8.43 g, yield 74%).

FAB-MS was measured, and compound G70 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

191. Synthesis of Compound G72

(Synthesis of intermediate IM-68 )

In an Ar atmosphere, in a 1L three-necked flask, IM-22 13.00 g (45.9 mmol), 3-chlorophenylboronic acid 7.90 g (1.1 equiv, 50.5 mmol), K ₂ CO ₃ 19.04 g (3.0 equiv, 60.7 mmol), Pd(PPh ₃ ) ₄ 2.65 g (0.05 eq, 2.3 mmol), and 321 mL of a mixed solution of Toluene/EtOH/H2O (4/2/1) were sequentially added, followed by heating and stirring at 80°C. After air cooling to room temperature, the reaction solution was extracted with Toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine, and then dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain an intermediate IM-68 (11.27 g, yield 78%).

FAB-MS was measured, and the intermediate IM-68 was identified as the mass number m/z = 314 was observed as a molecular ion peak.

(Synthesis of intermediate IM-69 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-68 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 4-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-69 (11.99 g, yield 79%).

FAB-MS was measured, and the compound IM-69 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound G72 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-69 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G72 (9.11 g, yield 80%).

FAB-MS was measured, and compound G72 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

192. Synthesis of Compound G73

(Synthesis of Compound G73 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G73 (8.39 g, yield 71%).

FAB-MS was measured, and compound G73 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

193. Synthesis of Compound G79

(Synthesis of Compound G79 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-2 17.38 g (55.2 mmol, 2.2 equiv), Pd(dba) ₂ 0.87 g (0.06 equiv, 1.5 mmol), NaO ^t Bu 7.23 g (4.0 equiv, 75.3 mmol) , Toluene 125 mL, 4-aminodibenzothiophene 5.00 g (25.1 mmol) and ^t Bu ₃ P 1.01 g (0.2 equiv, 5.0 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G79 (11.76 g, yield 62%).

FAB-MS was measured, and compound G79 was confirmed as the mass number m/z = 755 was observed as a molecular ion peak.

194. Synthesis of Compound G81

(Synthesis of Compound G81 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 1-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G81 (7.55 g, yield 70%).

FAB-MS was measured, and compound G81 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

195. Synthesis of Compound G82

(Synthesis of compound G82 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 3-bromodibenzofuran 4.55 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G82 (8.20 g, yield 76%).

FAB-MS was measured, and compound G82 was confirmed as the mass number m/z = 643 was observed as a molecular ion peak.

196. Synthesis of Compound G86

(Synthesis of intermediate IM-70 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-23 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzofuran 6.40 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-70 (10.70 g, yield 73%).

FAB-MS was measured, and the compound IM-70 was confirmed as the mass number m/z =461 was observed as a molecular ion peak.

(Synthesis of compound G86 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G86 (9.92 g, yield 83%).

FAB-MS was measured, and compound G86 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

197. Synthesis of Compound G87

(Synthesis of Compound G87 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 3-bromo-1,1':4',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G87 (8.49 g, yield 71%).

FAB-MS was measured, and compound G87 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

198. Synthesis of Compound G89

(Synthesis of Compound G89 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 1-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G89 (8.28 g, yield 72%).

FAB-MS was measured, and compound G89 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

199. Synthesis of Compound G90

(Synthesis of Compound G90 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(4-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G90 (7.82 g, yield 68%).

FAB-MS was measured, and compound G90 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

200. Synthesis of Compound G91

(Synthesis of Compound G91 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 9-(4-bromophenyl)phenanthrene 6.35 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G91 (8.54 g, yield 69%).

FAB-MS was measured, and compound G91 was confirmed as the mass number m/z = 713 was observed as a molecular ion peak.

201.Synthesis of Compound G92

(Synthesis of Compound G92 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 2-(3-bromophenyl)naphthalene 5.40 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G92 (8.51 g, yield 74%).

FAB-MS was measured, and compound G92 was confirmed as the mass number m/z = 663 was observed as a molecular ion peak.

202. Synthesis of Compound G93

(Synthesis of Compound G93 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-70 8.00 g (17.3 mmol), Pd(dba) ₂ 0.30 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.33 g (2.0 equiv, 34.7 mmol), Toluene 87 mL, 4-bromo-1,1':2',1''-terphenyl 5.90 g (1.1 equiv, 19.1 mmol) and ^t Bu ₃ P 0.35 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G93 (8.85 g, yield 74%).

FAB-MS was measured, and compound G93 was confirmed as the mass number m/z = 689 was observed as a molecular ion peak.

203. Synthesis of Compound G96

(Synthesis of intermediate IM-71 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-23 10.00 g (31.8 mmol), Pd(dba) ₂ 0.55 g (0.03 equiv, 1.0 mmol), NaO ^t Bu 3.05 g (1.0 equiv, 31.8 mmol), Toluene 159 mL, 1-aminodibenzothiophene 6.96 g (1.1 equiv, 34.9 mmol) and ^t Bu ₃ P 0.64 g (0.1 equiv, 3.2 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO 4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound IM-71 (10.62 g, yield 70%).

FAB-MS was measured, and the compound IM-71 was confirmed as the mass number m/z = 477 was observed as a molecular ion peak.

(Synthesis of Compound G96 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-71 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':4',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G96 (9.22 g, yield 78%).

FAB-MS was measured, and compound G96 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

204. Synthesis of Compound G100

(Synthesis of Compound G100 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-71 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 2-(4-bromophenyl)naphthalene 5.22 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and refluxing. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G100 (7.97, yield 70%).

FAB-MS was measured, and compound G100 was confirmed as the mass number m/z = 679 was observed as a molecular ion peak.

205. Synthesis of Compound G103

(Synthesis of Compound G103 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-71 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromo-1,1':2',1''-terphenyl 5.70 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating and reflux stirring. . After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G103 (7.92 g, yield 67%).

FAB-MS was measured, and compound G103 was confirmed as the mass number m/z = 705 was observed as a molecular ion peak.

206. Synthesis of Compound G53

(Synthesis of Compound G53 )

In an Ar atmosphere, in a 300 mL three-necked flask, IM-67 8.00 g (16.7 mmol), Pd(dba) ₂ 0.29 g (0.03 equiv, 0.5 mmol), NaO ^t Bu 3.22 g (2.0 equiv, 33.5 mmol), Toluene 84 mL, 4-bromodibenzothiophene 4.85 g (1.1 equiv, 18.4 mmol) and ^t Bu ₃ P 0.34 g (0.1 equiv, 1.7 mmol) were sequentially added, followed by heating under reflux and stirring. After air cooling to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer, the organic layers were combined, washed with brine, and dried over MgSO4. The crude product obtained by filtration of MgSO4 and concentration of the organic layer was purified by silica gel columnchromatography (a mixed solvent of Hexane and Toluene was used in the development layer) to obtain compound G53 (8.18 g, yield 74%).

FAB-MS was measured, and compound G53 was confirmed as the mass number m/z = 659 was observed as a molecular ion peak.

(Device preparation example)

The aforementioned compounds A4, A17, B13, B20, B40, C22, C51, D12, D22, E3, E32, F46, F53, G54, G58, A61-A73, A77, A78, A81, A82, A86-A93, A96 -A103, A53, A79, B61-B70, B72, B73, B81, B82, B86, B87, B89-B93, B96, B100, B103, B53, B79, C61-C70, C72, C73, C81, C82, C86 , C87, C89-C93, C96, C100, C103, C53, C79, D61-D70, D72, D73, D81, D82, D86, D87, D89-D93, D96, D100, D103, D53, D79, E61-E70 , E72, E73, E81, E82, E86, E87, E89-E93, E96, E100, E103, E53, E79, F61-F70, F72, F73, F81, F82, F86, F87, F89-F93, F96, F100 , F103, F53, F79, G61-G70, G72, G73, G81, G82, G86, G87, G89-G93, G96, G100, G103, G53, G79 of Examples 1 to 206 using the electron blocking layer material An organic electroluminescent device was fabricated.

[Example compound]

The organic electroluminescent devices of Comparative Examples 1 to 8 were manufactured using the following Comparative Examples compounds R-1 to R-8 as electron blocking layer materials.

[Comparative Example Compound]

In the organic electroluminescent devices of Examples 1 to 206 and Comparative Examples 1 to 8, a 150 nm first electrode was formed with ITO, a 10 nm-thick hole injection layer doped with 2% HIL was formed on HT1, and 120 nm was formed with HT1. A hole transport layer having a thickness was formed, an electron blocking layer having a thickness of 10 nm was formed with an Example compound or a Comparative Example compound, a light-emitting layer having a thickness of 30 nm was formed by doping 2% of BD on BH, and a hole blocking layer having a thickness of 10 nm with ET1 Then, a 20 nm-thick electron transport layer was formed with ET2, a 1 nm-thick electron injection layer was formed with LiF, and magnesium (Mg) and silver (Ag) were co-deposited at 9:1 (volume ratio) to have a thickness of 120 nm. A second electrode was formed. Each layer was formed by vacuum evaporation.

The voltage, half-life, luminous efficiency and color coordinates of the organic electroluminescent devices according to Examples 1 to 206 and Comparative Examples 1 to 9 are shown in Table 1 below.

E-low layer Voltage
(V) Life LT50(h) Luminous efficiency
(cd/A) Color coordinates
CIE(x,y) Example 1 Example compound A4 4.8 5.5 189 0.141, 0.051 Example 2 Example compound A17 4.6 5.5 190 0.142, 0.051 Example 3 Example compound B13 4.7 5.6 196 0.141, 0.051 Example 4 Example compound B20 4.6 5.5 195 0.141, 0.052 Example 5 Example compound B40 4.6 5.4 197 0.142, 0.052 Example 6 Example compound C25 4.6 5.4 199 0.142, 0.051 Example 7 Example Compound C51 4.8 5.4 196 0.141, 0.051 Example 8 Example compound D12 4.8 5.5 188 0.142, 0.052 Example 9 Example compound D22 4.7 5.4 190 0.142, 0.051 Example 10 Example compound E3 4.8 5.6 184 0.141, 0.052 Example 11 Example compound E32 4.8 5.6 189 0.141, 0.052 Example 12 Example compound F46 4.7 5.3 193 0.141, 0.051 Example 13 Example compound F53 4.8 5.5 192 0.141, 0.051 Example 14 Example compound G54 4.8 5.6 197 0.141, 0.052 Example 15 Example compound G58 4.8 5.6 185 0.142, 0.052 Example 16 Example Compound A61 4.6 5.4 186 0.141, 0.052 Example 17 Example compound A62 4.8 5.4 187 0.141, 0.051 Example 18 Example compound A63 4.7 5.5 185 0.142, 0.051 Example 19 Example Compound A64 4.7 5.3 194 0.141, 0.052 Example 20 Example Compound A65 4.7 5.3 192 0.141, 0.052 Example 21 Example Compound A66 4.6 5.5 190 0.141, 0.052 Example 22 Example Compound A67 4.7 5.4 190 0.142, 0.051 Example 23 Example Compound A68 4.8 5.4 193 0.141, 0.052 Example 24 Example compound A69 4.8 5.3 194 0.141, 0.052 Example 25 Example compound A70 4.7 5.3 189 0.141, 0.052 Example 26 Example Compound A71 4.6 5.5 186 0.142, 0.051 Example 27 Example compound A72 4.7 5.4 190 0.142, 0.051 Example 28 Example Compound A73 4.8 5.4 193 0.142, 0.052 Example 29 Example compound A77 4.8 5.3 193 0.142, 0.052 Example 30 Example compound A78 4.7 5.3 193 0.142, 0.051 Example 31 Example compound A81 4.6 5.6 188 0.141, 0.051 Example 32 Example Compound A82 4.8 5.4 194 0.141, 0.051 Example 33 Example compound A86 4.7 5.5 187 0.141, 0.052 Example 34 Example Compound A87 4.6 5.6 185 0.142, 0.052 Example 35 Example Compound A88 4.5 5.6 183 0.142, 0.052 Example 36 Example Compound A89 4.7 5.6 190 0.141, 0.051 Example 37 Example compound A90 4.7 5.6 191 0.142, 0.051 Example 38 Example compound A91 4.7 5.5 190 0.141, 0.051 Example 39 Example Compound A92 4.6 5.4 189 0.142, 0.052 Example 40 Example Compound A93 4.6 5.5 190 0.141, 0.051 Example 41 Example compound A96 4.7 5.5 188 0.141, 0.051 Example 42 Example compound A97 4.6 5.5 184 0.141, 0.052 Example 43 Example compound A98 4.5 5.8 183 0.142, 0.052 Example 44 Example compound A99 4.7 5.6 191 0.142, 0.052 Example 45 Example compound A100 4.8 5.5 193 0.141, 0.051 Example 46 Example compound A101 4.9 5.6 190 0.141, 0.052 Example 47 Example compound A102 4.6 5.5 188 0.142, 0.051 Example 48 Example compound A103 4.8 5.5 191 0.142, 0.051 Example 49 Example compound A53 4.8 5.4 193 0.141, 0.051 Example 50 Example compound A79 4.7 5.5 194 0.141, 0.052 Example 51 Example Compound B61 4.8 5.3 195 0.141, 0.051 Example 52 Example compound B62 4.8 5.3 197 0.141, 0.052 Example 53 Example compound B63 4.8 5.4 195 0.141, 0.051 Example 54 Example Compound B64 4.7 5.2 197 0.142, 0.051 Example 55 Example Compound B65 4.7 5.3 196 0.142, 0.053 Example 56 Example Compound B66 4.8 5.3 195 0.142, 0.051 Example 57 Example Compound B67 4.6 5.5 194 0.142, 0.052 Example 58 Example Compound B68 4.6 5.4 196 0.141, 0.051 Example 59 Example compound B69 4.6 5.3 198 0.141, 0.051 Example 60 Example compound B70 4.7 5.3 195 0.141, 0.051 Example 61 Example compound B72 4.8 5.4 195 0.142, 0.052 Example 62 Example compound B73 4.7 5.3 196 0.142, 0.052 Example 63 Example Compound B81 4.8 5.4 194 0.142, 0.052 Example 64 Example Compound B82 4.6 5.3 196 0.142, 0.051 Example 65 Example compound B86 4.6 5.4 196 0.142, 0.051 Example 66 Example compound B87 4.6 5.5 195 0.141, 0.051 Example 67 Example compound B89 4.7 5.4 194 0.142, 0.051 Example 68 Example compound B90 4.6 5.3 197 0.142, 0.051 Example 69 Example compound B91 4.8 5.5 195 0.141, 0.051 Example 70 Example Compound B92 4.6 5.4 194 0.141, 0.052 Example 71 Example Compound B93 4.6 5.3 195 0.141, 0.052 Example 72 Example compound B96 4.7 5.4 196 0.141, 0.052 Example 73 Example compound B100 4.7 5.3 196 0.141, 0.051 Example 74 Example compound B103 4.8 5.3 194 0.142, 0.051 Example 75 Example compound B53 4.6 5.5 196 0.142, 0.052 Example 76 Example compound B79 4.7 5.3 196 0.142, 0.052 Example 77 Example compound C61 4.7 5.3 196 0.142, 0.052 Example 78 Example compound C62 4.6 5.3 197 0.141, 0.051 Example 79 Example compound C63 4.6 5.4 196 0.141, 0.052 Example 80 Example compound C64 4.7 5.3 198 0.142, 0.052 Example 81 Example compound C65 4.7 5.4 197 0.141, 0.051 Example 82 Example compound C66 4.6 5.5 196 0.142, 0.051 Example 83 Example Compound C67 4.8 5.4 195 0.142, 0.051 Example 84 Example Compound C68 4.8 5.4 197 0.141, 0.052 Example 85 Example compound C69 4.6 5.3 198 0.141, 0.052 Example 86 Example compound C70 4.7 5.3 194 0.142, 0.051 Example 87 Example compound C72 4.8 5.3 194 0.141, 0.051 Example 88 Example compound C73 4.7 5.4 195 0.142, 0.051 Example 89 Example compound C81 4.6 5.5 194 0.142, 0.051 Example 90 Example compound C82 4.6 5.3 197 0.141, 0.051 Example 91 Example compound C86 4.8 5.4 197 0.142, 0.051 Example 92 Example compound C87 4.8 5.4 196 0.142, 0.051 Example 93 Example compound C89 4.8 5.4 196 0.142, 0.051 Example 94 Example compound C90 4.6 5.3 197 0.141, 0.052 Example 95 Example compound C91 4.7 5.5 195 0.141, 0.052 Example 96 Example Compound C92 4.6 5.4 195 0.142, 0.052 Example 97 Example compound C93 4.6 5.4 196 0.141, 0.052 Example 98 Example compound C96 4.7 5.4 197 0.141, 0.052 Example 99 Example compound C100 4.7 5.4 197 0.142, 0.052 Example 100 Example compound C103 4.8 5.4 194 0.142, 0.051 Example 101 Example compound C53 4.6 5.5 195 0.142, 0.051 Example 102 Example compound C79 4.6 5.5 194 0.141, 0.052 Example 103 Example compound D61 4.6 5.4 190 0.142, 0.051 Example 104 Example compound D62 4.8 5.3 192 0.142, 0.052 Example 105 Example compound D63 4.7 5.4 191 0.141, 0.051 Example 106 Example compound D64 4.7 5.4 192 0.141, 0.051 Example 107 Example compound D65 4.7 5.4 191 0.141, 0.051 Example 108 Example compound D66 4.6 5.5 189 0.141, 0.052 Example 109 Example compound D67 4.6 5.5 190 0.141, 0.052 Example 110 Example compound D68 4.8 5.4 191 0.141, 0.051 Example 111 Example compound D69 4.8 5.3 192 0.141, 0.052 Example 112 Example compound D70 4.8 5.5 188 0.142, 0.051 Example 113 Example compound D72 4.6 5.5 187 0.142, 0.052 Example 114 Example compound D73 4.7 5.4 192 0.141, 0.052 Example 115 Example compound D81 4.8 5.5 187 0.141, 0.052 Example 116 Example compound D82 4.6 5.6 193 0.141, 0.051 Example 117 Example compound D86 4.6 5.5 190 0.141, 0.051 Example 118 Example compound D87 4.8 5.5 189 0.142, 0.052 Example 119 Example compound D89 4.7 5.5 191 0.142, 0.051 Example 120 Example compound D90 4.7 5.4 192 0.142, 0.051 Example 121 Example compound D91 4.6 5.6 193 0.142, 0.051 Example 122 Example compound D92 4.7 5.5 190 0.142, 0.051 Example 123 Example compound D93 4.8 5.5 191 0.142, 0.051 Example 124 Example compound D96 4.7 5.5 190 0.142, 0.051 Example 125 Example compound D100 4.6 5.5 191 0.141, 0.052 Example 126 Example compound D103 4.8 5.5 190 0.141, 0.052 Example 127 Example compound D53 4.7 5.7 192 0.141, 0.052 Example 128 Example compound D79 4.7 5.6 192 0.142, 0.052 Example 129 Example compound E61 4.7 5.4 188 0.142, 0.052 Example 130 Example compound E62 4.6 5.4 189 0.141, 0.052 Example 131 Example compound E63 4.7 5.6 188 0.142, 0.051 Example 132 Example compound E64 4.8 5.5 190 0.141, 0.051 Example 133 Example compound E65 4.8 5.5 189 0.141, 0.052 Example 134 Example compound E66 4.8 5.6 187 0.142, 0.051 Example 135 Example compound E67 4.6 5.6 188 0.142, 0.051 Example 136 Example compound E68 4.8 5.6 190 0.142, 0.052 Example 137 Example compound E69 4.7 5.5 192 0.142, 0.051 Example 138 Example compound E70 4.7 5.6 189 0.142, 0.052 Example 139 Example compound E72 4.6 5.6 188 0.141, 0.052 Example 140 Example compound E73 4.6 5.5 190 0.142, 0.052 Example 141 Example compound E81 4.6 5.7 186 0.141, 0.052 Example 142 Example compound E82 4.7 5.5 191 0.141, 0.052 Example 143 Example compound E86 4.7 5.4 192 0.141, 0.052 Example 144 Example compound E87 4.7 5.6 188 0.141, 0.051 Example 145 Example compound E89 4.8 5.6 190 0.142, 0.051 Example 146 Example compound E90 4.8 5.5 192 0.142, 0.051 Example 147 Example compound E91 4.8 5.6 192 0.141, 0.051 Example 148 Example compound E92 4.8 5.6 186 0.141, 0.052 Example 149 Example compound E93 4.7 5.6 190 0.141, 0.052 Example 150 Example compound E96 4.6 5.4 190 0.141, 0.052 Example 151 Example compound E100 4.6 5.5 193 0.141, 0.052 Example 152 Example compound E103 4.8 5.5 189 0.141, 0.051 Example 153 Example compound E53 4.7 5.6 186 0.141, 0.051 Example 154 Example compound E79 4.6 5.5 191 0.141, 0.051 Example 155 Example compound F61 4.8 5.2 193 0.142, 0.052 Example 156 Example compound F62 4.7 5.2 194 0.142, 0.052 Example 157 Example compound F63 4.8 5.3 193 0.141, 0.052 Example 158 Example compound F64 4.6 5.2 196 0.142, 0.052 Example 159 Example compound F65 4.6 5.3 194 0.141, 0.051 Example 160 Example compound F66 4.7 5.3 193 0.141, 0.051 Example 161 Example compound F67 4.7 5.4 194 0.142, 0.051 Example 162 Example compound F68 4.8 5.3 194 0.141, 0.051 Example 163 Example compound F69 4.8 5.3 197 0.142, 0.051 Example 164 Example compound F70 4.7 5.4 193 0.141, 0.052 Example 165 Example compound F72 4.6 5.4 193 0.141, 0.052 Example 166 Example compound F73 4.7 5.3 194 0.141, 0.052 Example 167 Example compound F81 4.8 5.5 193 0.141, 0.052 Example 168 Example compound F82 4.6 5.2 198 0.142, 0.052 Example 169 Example compound F86 4.7 5.2 196 0.141, 0.051 Example 170 Example compound F87 4.7 5.4 194 0.141, 0.051 Example 171 Example compound F89 4.8 5.4 195 0.142, 0.052 Example 172 Example compound F90 4.8 5.3 196 0.141, 0.052 Example 173 Example compound F91 4.8 5.5 194 0.142, 0.051 Example 174 Example compound F92 4.7 5.3 196 0.142, 0.052 Example 175 Example compound F93 4.7 5.5 196 0.142, 0.052 Example 176 Example compound F96 4.6 5.3 196 0.141, 0.051 Example 177 Example compound F100 4.7 5.3 197 0.141, 0.052 Example 178 Example compound F103 4.6 5.4 195 0.141, 0.052 Example 179 Example compound F53 4.6 5.5 195 0.141, 0.052 Example 180 Example compound F79 4.8 5.8 196 0.141, 0.051 Example 181 Example compound G61 4.8 5.5 188 0.142, 0.051 Example 182 Example compound G62 4.7 5.3 189 0.142, 0.051 Example 183 Example compound G63 4.6 5.6 187 0.141, 0.051 Example 184 Example compound G64 4.7 5.5 190 0.142, 0.052 Example 185 Example compound G65 4.8 5.6 188 0.141, 0.052 Example 186 Example compound G66 4.8 5.6 185 0.141, 0.052 Example 187 Example compound G67 4.6 5.4 188 0.142, 0.052 Example 188 Example compound G68 4.7 5.4 189 0.142, 0.051 Example 189 Example compound G69 4.6 5.5 189 0.141, 0.051 Example 190 Example compound G70 4.8 5.5 187 0.142, 0.052 Example 191 Example compound G72 4.8 5.5 185 0.141, 0.052 Example 192 Example compound G73 4.6 5.8 188 0.141, 0.052 Example 193 Example compound G81 4.7 5.5 186 0.142, 0.052 Example 194 Example compound G82 4.8 5.5 190 0.142, 0.052 Example 195 Example compound G86 4.7 5.6 190 0.141, 0.052 Example 196 Example compound G87 4.6 5.6 187 0.141, 0.051 Example 197 Example compound G89 4.7 5.5 188 0.142, 0.052 Example 198 Example compound G90 4.7 5.4 190 0.142, 0.051 Example 199 Example compound G91 4.8 5.6 189 0.142, 0.052 Example 200 Example compound G92 4.8 5.6 187 0.142, 0.051 Example 201 Example compound G93 4.8 5.5 190 0.141, 0.052 Example 202 Example compound G96 4.7 5.5 189 0.141, 0.052 Example 203 Example compound G100 4.8 5.4 190 0.141, 0.051 Example 204 Example compound G103 4.6 5.6 188 0.142, 0.051 Example 205 Example compound G53 4.8 5.8 186 0.141, 0.051 Example 206 Example compound G79 4.7 5.6 186 0.142, 0.051 Comparative Example 1 Comparative Example Compound R1 5.0 4.9 167 0.140, 0.052 Comparative Example 2 Comparative Example Compound R2 5.2 3.8 165 0.141, 0.053 Comparative Example 3 Comparative Example Compound R3 5.1 4.0 167 0.142, 0.051 Comparative Example 4 Comparative Example Compound R4 5.3 4.2 163 0.139, 0.049 Comparative Example 5 Comparative Example Compound R5 5.1 5.0 168 0.140, 0.050 Comparative Example 6 Comparative Example Compound R6 5.5 3.5 155 0.137, 0.047 Comparative Example 7 Comparative Example Compound R7 4.9 5.0 157 0.143, 0.053 Comparative Example 8 Comparative Example Compound R8 4.9 4.9 169 0.142, 0.052

The luminous efficiency is a value measured at 10mA/cm ² , and the half life is a value at 1.0mA/cm ² .

Referring to Table 1, Examples 1 to 206 have lower driving voltage, longer life, and higher efficiency compared to Comparative Examples 1 to 8. The monoamine compound according to an embodiment of the present invention includes a substituted β-phenylnaphthyl group, thereby achieving low driving voltage, long life, and high efficiency. By introducing a naphthyl group excellent in resistance to heat and electric charges, while maintaining the characteristics of an amine, a long lifespan of the device was realized. In addition, as the phenyl group is substituted in the naphthyl group, the volume increases, the symmetry of the molecule decreases, and crystallization is suppressed. As a result, the film quality can be improved, thereby improving the efficiency.

In Examples 1, 2, 8 to 11, 14 to 50, 103 to 154, and 181 to 206, it can be seen that the efficiency of the device is particularly improved. The compounds included in Examples 1, 2, 8 to 11, 14 to 50, 103 to 154, and 181 to 206 include a substituent at the α position of the naphthyl group, and the substituent bonded to the α position and the α′ position on the other side Since stereoelectronic repulsion occurs between the hydrogen atoms substituted in the naphthyl group, the phenyl group substituted in the naphthyl group and the naphthyl group skeleton are distorted with each other, thereby reducing the planarity of the entire molecule, suppressing crystallinity, and improving the hole transport property. This is believed to be due to the improved probability of recombination of holes and electrons at.

Further, in Examples 16 to 50, 106 to 128, 132 to 154, and 184 to 206, in addition to the naphthyl group skeleton in which the phenyl group is substituted at the α position, 4-fluorene, 4-dibenzothiophene, 1-dibenzofuran or 1 Since a bulky dibenzoheteroaryl group such as -dibenzothiophene is substituted, it can be confirmed that the luminous efficiency of the device is greatly improved because the film-forming property is improved.

In Examples 3 to 7, 12, 13, 51 to 102, and 155 to 180, the device life was particularly improved. The compounds included in Examples 3 to 7, 12, 13, 51 to 102, and 155 to 180 include a substituent at the α-position of the naphthyl group, and the substituent and the naphthyl group bonded to the α-position take a three-dimensional structure close to the plane. By doing so, the conjugate around the amine is delocalized and the radical state is stabilized, so that the lifespan is improved.

In addition, Examples 7, 13, 16 to 50, 54 to 76, 80 to 102, and 158 to using a compound in which 4-fluorene, 4-dibenzothiophene, 1-dibenzofuran or 1-dibenzothiophene is bonded to a nitrogen atom as described above were used. At 180, it was confirmed that the luminous efficiency was improved as the film-forming property was improved, and the result was excellent in both device efficiency and lifetime.

Comparative Example 1 showed a result that the device life was particularly reduced compared to the Example. Comparative Example Compound R1 has an amine group bonded to the α-position of the naphthyl group through a linker, similar to an embodiment of the present invention, but two phenyl groups are substituted in the naphthyl group, and the HOMO orbital is largely distributed in the naphthyl group. , As the electron density on the side of the amine group is relatively small, it is judged that it is difficult to maintain the characteristics of the amine that induces a long life.

Comparative Example Compound 2 included in Comparative Example 2 is an amine compound containing a naphthyl group, but since it does not contain a phenylnaphthyl group, charge resistance is low, and the film quality is insufficient, so that the device life of Comparative Example 2 is short and the efficiency is low. .

Comparative Examples 3 and 4 included in Comparative Examples 3 and 4 are compounds in which an amine group is bonded to the α-position of the naphthyl group through a linker, similar to an embodiment of the present invention, but the naphthyl group is not a phenyl group but a polycyclic aromatic Since the group is bonded, the molecular stacking is very strong due to the influence of the polycyclic aromatic ring group, and it is judged that thermal decomposition easily occurred due to the high deposition temperature. Accordingly, the luminous efficiency and lifespan of Comparative Examples 3 and 4 compared to the Example All of these showed deteriorating results.

Comparative Example Compound 6 included in Comparative Example 6 is a compound in which an amine group is bonded to the α-position of the naphthyl group through a linker, similar to the embodiment of the present invention, but molecular stacking includes two substituents in the phenyl group. Since this is very strong and the deposition temperature is high, thermal decomposition easily occurs, and both the luminous efficiency and lifetime of Comparative Example 6 are lowered compared to the Example.

Comparative Examples 5 and 7 showed a result of particularly lower luminous efficiency compared to Examples. Comparative Example Compound R5 has a heterocyclic dibenzofuran ring substituted on the substituted phenyl group of the naphthyl group, and Comparative Example Compound R7 is a diamine compound, so it is determined that the carrier balance is broken.

Comparative Example 8 showed the result that both luminous efficiency and lifespan were lowered compared to the Example. Comparative Example Compound R8 is judged to easily undergo thermal decomposition by simultaneously binding 3-dibenzofuranly and 9-phenanthlyl to a nitrogen atom. In other words, 9-phenanthlyl, which can be very strong in molecular stacking, is bonded to nitrogen, and at the same time, 3-dibenzofuranly, which increases planarity throughout the molecule, is bonded to nitrogen. Accordingly, it is determined that molecular stacking is enhanced, and thermal decomposition of molecules easily occurs as the deposition temperature increases, resulting in a decrease in the efficiency and lifetime of the device.

The monoamine compound according to an embodiment of the present invention is used in the hole transport region to contribute to low driving voltage, high efficiency, and long life of the organic electroluminescent device.

Although the embodiments of the present invention have been described above, those of ordinary skill in the art to which the present invention pertains will understand that the present invention can be implemented in other specific forms without changing the technical spirit or essential features. . Therefore, it should be understood that the embodiments described above are illustrative in all respects and not limiting.

10: organic electroluminescent element EL1: first electrode
HTR: hole transport region HIL: hole injection layer
HTL: hole transport layer EML: light emitting layer
ETR: electron transport region ETL: electron transport layer
EIL: electron injection layer EL2: second electrode

Claims (41)

A first electrode;
A hole transport region provided on the first electrode;
A light emitting layer provided on the hole transport region;
An electron transport region provided on the emission layer; And
A second electrode provided on the electron transport region,
The hole transport region is an organic electroluminescent device comprising a monoamine compound represented by the following Formula 1:
[Formula 1]

In Formula 1,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted alkyl group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 or more and 20 or less carbon atoms for forming a ring, and 6 or more and 30 or less carbon atoms for forming a substituted or unsubstituted ring. An aryl group of, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
R ₁ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups,
R ₂ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
a is an integer of 0 or more and 3 or less,
m is an integer of 0 or more and 1 or less,
n is an integer of 0 or more and 6 or less,
If the Ar ₁ 3-dibenzo-furanyl group Ar ₂ is a 9-phenanthryl group, not, if Ar ₂ is 3-dibenzo-furanyl group Ar ₁ is not 9-phenanthryl group.
The method of claim 1,
Formula 1 is an organic electroluminescent device represented by any one of the following Formulas 2 to 8:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 2 to 8,
Ar ₁ , Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1. The method of claim 1,
L is an organic electroluminescent device that is a substituted or unsubstituted arylene group having 6 or more and 12 or less ring carbon atoms. The method of claim 3,
L is an organic electroluminescent device that is a substituted or unsubstituted phenylene group. The method of claim 1,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted aryl group having 6 or more and 24 or less ring carbon atoms. The method of claim 5,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted phenanthryl group. Organic electroluminescent device. The method of claim 1,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted heteroaryl group having 5 or more and 24 or less ring carbon atoms. The method of claim 7,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group in an organic electroluminescent device. The method of claim 7,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene organic electroluminescent device. The method of claim 1,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted dibenzothiophene group. The method of claim 10,
Ar ₁ and Ar ₂ At least one of is a substituted or unsubstituted 4-dibenzothiophene organic electroluminescent device. The method of claim 1,
The compound represented by Formula 1 is an organic electroluminescent device represented by Formula 9:
[Formula 9]

In Formula 9,
R ₃ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups,
p is an integer of 0 or more and 7 or less,
Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1. The method of claim 1,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted dibenzofuran group. The method of claim 13,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted 1-dibenzofuran group. The method of claim 1,
The compound represented by Formula 1 is an organic electroluminescent device represented by Formula 10 below:
[Formula 10]

In Chemical Formula 10,
R ₄ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups,
q is an integer of 0 or more and 7 or less,
Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1. The method of claim 13,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted 4-dibenzofuran group. The method of claim 1,
The compound represented by Formula 1 is an organic electroluminescent device represented by Formula 11 below:
[Formula 11]

In Formula 11,
R ₅ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups,
r is an integer of 0 or more and 7 or less,
Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1.
The method of claim 1,
R ₂ is a hydrogen atom or a deuterium atom. The method of claim 1,
At least one of Ar ₁ , Ar ₂ , L, R ₁ , and R ₂ is an organic electroluminescent device in which one or more deuterium atoms are substituted. The method of claim 1,
The hole transport region has a multilayer structure having a plurality of layers,
An organic electroluminescent device in which a layer of the plurality of layers in contact with the emission layer includes a monoamine compound represented by Formula 1 above. The method of claim 1,
The hole transport region is
A hole injection layer disposed on the first electrode;
A hole transport layer disposed on the hole injection layer; And
Including an electron blocking layer disposed on the hole transport layer,
The electron blocking layer is an organic electroluminescent device comprising the monoamine compound represented by the formula (1). The method of claim 1,
The electron transport region is
A hole blocking layer disposed on the emission layer;
An electron transport layer disposed on the hole blocking layer; And
An organic electroluminescent device comprising an electron injection layer disposed on the electron transport layer. The method of claim 1,
The monoamine compound represented by Formula 1 is an organic electroluminescent device that is at least one selected from compounds represented by the following compound groups 1 to 7:
[Compound group 1]

[Compound group 2]

[Compound group 3]

[Compound group 4]

[Compound group 5]

[Compound group 6]

[Compound group 7]

. The method of claim 23,
The monoamine compound represented by Formula 1 is an organic electroluminescent device that is at least one selected from the compounds represented in the following compound group 1-1 to compound group 7-1:
[Compound group 1-1]

[Compound group 2-1]

[Compound group 3-1]

[Compound group 4-1]

[Compound group 5-1]

[Compound group 6-1]

[Compound group 7-1]

. Monoamine compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted alkyl group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 or more and 20 or less carbon atoms for forming a ring, and 6 or more and 30 or less carbon atoms for forming a substituted or unsubstituted ring. An aryl group of, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
R ₁ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups,
R ₂ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
a is an integer of 0 or more and 3 or less,
m is an integer of 0 or more and 1 or less,
n is an integer of 0 or more and 6 or less,
If the Ar ₁ 3-dibenzo-furanyl group Ar ₂ is a 9-phenanthryl group, not, if Ar ₂ is 3-dibenzo-furanyl group Ar ₁ is not 9-phenanthryl group. The method of claim 25,
Formula 1 is a monoamine compound represented by any one of the following Formulas 2 to 8:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 2 to 8,
Ar ₁ , Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1. The method of claim 25,
L is a monoamine compound that is a substituted or unsubstituted phenylene group. The method of claim 25,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted aryl group having 6 or more and 24 or less ring carbon atoms. The method of claim 25,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted heteroaryl group having 5 or more and 24 or less ring carbon atoms. The method of claim 25,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group. The method of claim 25,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, a monoamine compound. The method of claim 25,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted dibenzothiophene group. The method of claim 32,
Ar ₁ and Ar ₂ is a monoamine compound in which at least one is a substituted or unsubstituted 4-dibenzothiophene group. The method of claim 25,
The compound represented by Formula 1 is a monoamine compound represented by the following Formula 9:
[Formula 9]

In Formula 9,
R ₃ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl groups,
p is an integer of 0 or more and 7 or less,
Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1. The method of claim 25,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted dibenzofuran group. The method of claim 35,
At least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted 1-dibenzofuran group, or a substituted or unsubstituted 4-dibenzofuran group. The method of claim 25,
The compound represented by Formula 1 is a monoamine compound represented by Formula 10 or Formula 11:
[Formula 10]

[Formula 11]

In Formulas 10 and 11,
R ₄ and R ₅ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or It is an unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms,
q and r are each independently an integer of 0 or more and 7 or less,
Ar ₂ , L, R ₁ , R ₂ , a, m, and n are the same as defined in Formula 1. The method of claim 25,
R ₂ is a monoamine compound which is a hydrogen atom or a deuterium atom. The method of claim 25,
At least one of Ar ₁ , Ar ₂ , L, R ₁ , and R ₂ is a monoamine compound in which one or more deuterium atoms are substituted. The method of claim 25,
The monoamine compound represented by Formula 1 is any one selected from compounds represented in the following compound groups 1 to 7 monoamine compounds:
[Compound group 1]

[Compound group 2]

[Compound group 3]

[Compound group 4]

[Compound group 5]

[Compound group 6]

[Compound group 7]

. The method of claim 40,
The monoamine compound represented by Formula 1 is at least one selected from compounds represented in the following compound group 1-1 to compound group 7-1:
[Compound group 1-1]

[Compound group 2-1]

[Compound group 3-1]

[Compound group 4-1]

[Compound group 5-1]

[Compound group 6-1]

[Compound group 7-1]

.

Images