KR102577617B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention is used in the organic material layer, preferably the light-emitting layer, of the organic electroluminescent device, thereby improving the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device. etc. can be improved.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same.

Beginning with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. presented an organic electroluminescent device with a layered structure divided into a hole layer and a light-emitting functional layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

To date, NPB, BCP, and Alq ₃ are widely known as hole injection layer, hole transport layer, hole blocking layer, and electron transport layer materials, and anthracene derivatives have been reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

The present invention can be applied to organic electroluminescent devices and aims to provide a new organic compound that has excellent hole and electron injection and transport capabilities, luminescence capabilities, etc.

Another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage, high luminous efficiency, and improved lifespan by including the novel organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

Y is O, S or C(R ₅ )(R ₆ );

Ring A is represented by any one of the following formulas 2 to 5;

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 1 to 5,

The dotted line indicates the part where condensation takes place;

p and q are integers from 0 to 3;

r and m are integers from 0 to 4;

n is an integer from 0 to 6;

l is an integer from 0 to 8;

L ₁ is selected from the group consisting of a direct bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

L ₂ is an arylene group of C ₆ to C ₁₈ or a heteroarylene group of 5 to 18 nuclear atoms;

R ₁ to R ₆ and Ar ₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, selected from the group consisting of a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group; When each of R ₁ to R ₄ is plural, they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, and cycloalkyl group of R ₁ to R ₆ and Ar ₁ , heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and arylsilyl groups of C ₆ to C ₆₀ .

The present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound of Formula 1. .

In the present invention, “alkyl” is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl. etc., but is not limited to this.

In the present invention, “alkenyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond, examples of which include vinyl, Examples include allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond, examples of which include ethynyl. , 2-propynyl, etc., but is not limited thereto.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a monovalent ring in which two or more rings are condensed with each other, contains only carbon as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule has non-aromaticity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, etc.

“Heteroaryl” in the present invention refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, contain heteroatoms selected from N, O, P, S, and Se in addition to carbon as ring forming atoms, and the entire molecule is non-aromatic. It is interpreted to include monovalent groups with aromaticity. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; Examples include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, “alkyloxy” is a monovalent substituent represented by R'O-, where R' means 1 to 40 alkyl, and has a linear, branched or cyclic structure. It is interpreted as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms.

“Cycloalkyl” in the present invention refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon, preferably 1 to 3 carbons in the ring, is N, O, It is substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 5 to 60 carbon atoms.

In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Since the compound of the present invention has excellent thermal stability, carrier transport ability, luminescence ability, etc., it can be usefully applied as an organic layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device containing the compound of the present invention in the organic material layer has greatly improved aspects such as luminous performance, driving voltage, lifespan, and efficiency, and can be effectively applied to full color display panels.

Figure 1 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Figure 2 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

One. new organic compounds

The new compound of the present invention can be represented by the following formula (1):

[Formula 1]

In Formula 1,

Y is O, S or C(R ₅ )(R ₆ );

Ring A is represented by any one of the following formulas 2 to 5;

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 1 to 5,

The dotted line indicates the part where condensation takes place;

p and q are integers from 0 to 3;

r and m are integers from 0 to 4;

n is an integer from 0 to 6;

l is an integer from 0 to 8;

L ₁ is selected from the group consisting of a direct bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

L ₂ is an arylene group of C ₆ to C ₁₈ or a heteroarylene group of 5 to 18 nuclear atoms;

R ₁ to R ₆ and Ar ₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, selected from the group consisting of a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group; When each of R ₁ to R ₄ is plural, they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, and cycloalkyl group of R ₁ to R ₆ and Ar ₁ , heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group and arylsilyl groups of C ₆ to C ₆₀ .

The compounds of the present invention include dibenzofuran, dibenzothiophene, dimethyl fluorene, diphenylfluorene, spirofluorene, phenoxazine, etc. at position 1 of carbazole and a linker such as phenyl, biphenyl, naphthyl, etc. An electron withdrawing group (EWG) with high electron absorption, such as a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.), is bonded to the substituted basic skeleton, giving the entire molecule bipolar characteristics. Therefore, the binding force between holes and electrons can be increased.

The compound of the present invention has steric hindrance due to the substitution structure at position 1 of carbazole. Because of this, it has high triplet energy and can prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer or hole transport layer adjacent to the light-emitting layer. By increasing the number of excitons contributing to light emission within the light-emitting layer, the light-emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, effectively increasing the lifespan of the device.

Therefore, the compound represented by Formula 1 of the present invention is an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (green or red phosphorescent host material), an electron transport layer/injection layer material, a light emitting auxiliary layer material, and an electron transport auxiliary layer. It can be used as a material, more preferably a light emitting layer material, an electron transport layer material, and an electron transport auxiliary layer material. In addition, the performance and lifespan characteristics of an organic electroluminescent device containing the compound of Formula 1 can be greatly improved, and the performance of a full-color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.

According to a preferred embodiment of the present invention, the compound may be represented by any one of the following formulas 6 to 10:

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

In Formulas 6 to 10 above.

R ₁ to R ₄ , m, n, l, p, q, r, L ₁ , L _2, Ar ₁ and Y are as defined in Formula 1.

According to a preferred embodiment of the present invention, R ₁ to R ₆ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. selected,

The alkyl group, aryl group, and heteroaryl group of R ₁ to R ₆ are each independently selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. When substituted or unsubstituted with more than one type of substituent and substituted with multiple substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁ to R ₆ are each independently selected from a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, a pyridinyl group, and a pyridinyl group. It is selected from the group consisting of midinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxynyl group,

R ₁ to R ₆ methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, terphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, di Benzothiophenyl group, carbazolyl group, fluorenyl group, spirofluorenyl group and dibenzodioxynyl group are each independently an alkyl group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , and a C ₆ to C ₆₀ group. It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, L ₁ may be a direct bond or a linker selected from the group consisting of the following formulas A-1 to A-5, more preferably a direct bond or A-1 or A- The linker indicated by 2 may be:

In the above formulas A-1 to A-5,

* indicates the part where the combination takes place.

According to a preferred embodiment of the present invention, L ₂ may be a linker selected from the group consisting of the following formulas A-1 to A-5, and more preferably may be a linker represented by A-1 to A-4. there is:

In the above formulas A-1 to A-5,

* indicates the part where the combination takes place.

According to a preferred embodiment of the present invention, Ar ₁ is selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms,

The alkyl group, aryl group, and heteroaryl group of Ar ₁ are each independently one or more substituents selected from the group consisting of an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ is methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group. , pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, isoquinolinyl group, cynolinyl group, quinoxalinyl group and quinazolinyl group,

Ar ₁ methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, tria Zinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, isoquinolinyl group, cinolinyl group, quinoxalinyl group and quinazolinyl group are each independently an alkyl group of C ₁ to C ₄₀ , C ₆ to C ₆₀ is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ is methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group. , pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, isoquinolinyl group, cynolinyl group, quinoxalinyl group and quinazolinyl group,

Ar ₁ methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, tria Zinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, isoquinolinyl group, cinolinyl group, quinoxalinyl group and quinazolinyl group are each independently methyl group, ethyl group, propyl group, butyl group, pentyl group, Phenyl group, biphenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, It is substituted or unsubstituted with one or more substituents selected from the group consisting of isoquinolinyl group, cynolinyl group, quinoxalinyl group, and quinazolinyl group, and when substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent represented by any one of the following formulas 11 to 13:

[Formula 11]

[Formula 12]

[Formula 13]

In Formulas 11 to 13,

* refers to the part where the combination takes place;

Z ₁ to Z ₅ are each independently N or C(R ₇ );

s is an integer from 0 to 4;

R ₇ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, Heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphospha It is selected from the group consisting of a nyl group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, or is combined with an adjacent group to form a condensed ring, and when R ₇ is plural, they are are the same or different from each other;

R ₈ is each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C 40 alkenyl group, C ₂ to _{C 40 alkynyl} group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , C ₆ to C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, or is combined with an adjacent group to form a condensed ring, and wherein R ₈ is plural In the case of individuals, they may be the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₇ and R ₈ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylboron group, C ₆ At least one substituent selected from the group consisting of an aryl boron group of ~C ₆₀ , an arylphosphanyl group of C ₆ ~ C ₆₀ , a mono or diarylphosphinyl group of C ₆ ~ C ₆₀ , and an arylsilyl group of C ₆ ~ C ₆₀ When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. selected,

The alkyl group, aryl group, and heteroaryl group of R ₇ and R ₈ are each independently selected from the group consisting of an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. When substituted or unsubstituted with more than one type of substituent and substituted with multiple substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently composed of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group. selected from the military,

The methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group and triazinyl group of R ₇ and R ₈ are each independently an alkyl group of C ₁ to C ₄₀ , C ₆ to It is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group at C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms, and when substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently composed of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group. selected from the military,

The methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, and triazinyl group of R ₇ and R ₈ are each independently methyl group, ethyl group, propyl group, butyl group, and phenyl group. It is substituted or unsubstituted with one or more substituents selected from the group consisting of a tyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, and triazinyl group, and when substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 11 may be a substituent represented by Formula 14 below:

[Formula 14]

In Formula 14 above,

* refers to the part where the combination takes place;

R ₉ and R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ It is selected from the group consisting of a C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₉ and R ₁₀ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~C ₆₀ arylamine group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~C ₄₀ alkylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ At least one substituent selected from the group consisting of an aryl boron group of ~C ₆₀ , an arylphosphanyl group of C ₆ ~ C ₆₀ , a mono or diarylphosphinyl group of C ₆ ~ C ₆₀ , and an arylsilyl group of C ₆ ~ C ₆₀ is substituted or unsubstituted, and when substituted with a plurality of substituents, they are the same or different from each other;

Z ₁ , Z ₃ and Z ₅ are as defined in Formula 11.

According to a preferred embodiment of the present invention, the substituent represented by Formula 11 may be a substituent represented by any one of the following Formulas B-1 to B-3:

In the above formulas B-1 to B-3,

* refers to the part where the combination takes place,

R ₉ and R ₁₀ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ selected from the group consisting of a C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₉ and R ₁₀ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~C ₆₀ arylamine group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~C ₄₀ alkylsilyl group, C ₁ ~C ₄₀ alkylboron group, C ₆ At least one substituent selected from the group consisting of an aryl boron group of ~C ₆₀ , an arylphosphanyl group of C ₆ ~ C ₆₀ , a mono or diarylphosphinyl group of C ₆ ~ C ₆₀ , and an arylsilyl group of C ₆ ~ C ₆₀ When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ are each independently selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. is selected;

The alkyl group, aryl group, and heteroaryl group of R ₉ and R ₁₀ are each independently selected from the group consisting of an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. When substituted or unsubstituted with more than one type of substituent and substituted with multiple substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group. is selected from the group consisting of,

Of R ₉ and R ₁₀ Phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group, and dibenzothiophenyl group are each independently an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ and heteroaryl groups having 5 to 60 nuclear atoms. When substituted or unsubstituted with one or more substituents selected from the group consisting of a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group. is selected from the group consisting of,

Of R ₉ and R ₁₀ Phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group are each independently methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, When unsubstituted or substituted with one or more substituents selected from the group consisting of pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group, and substituted with a plurality of substituents, these are the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 12 may be a substituent represented by the following Formula C-1 or C-2:

In the above formula C-1 or C-2,

* refers to the part where the combination takes place,

s, R ₇ and R ₈ are as defined in Formula 12.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. is selected;

The alkyl group, aryl group, and heteroaryl group of R ₇ and R ₈ are each independently selected from the group consisting of an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. When substituted or unsubstituted with more than one type of substituent and substituted with multiple substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group. is selected from the group consisting of,

Of R ₇ and R ₈ Phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group, and dibenzothiophenyl group are each independently an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ and heteroaryl groups having 5 to 60 nuclear atoms. When substituted or unsubstituted with one or more substituents selected from the group consisting of a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group. is selected from the group consisting of,

Of R ₇ and R ₈ Phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group are each independently methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, When unsubstituted or substituted with one or more substituents selected from the group consisting of pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group, and substituted with a plurality of substituents, these are the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 13 may be a substituent represented by Formula 15 below:

[Formula 15]

In Formula 15 above,

* refers to the part where the combination takes place,

s, R ₇ and R ₈ are as defined in Formula 13.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. is selected;

The alkyl group, aryl group, and heteroaryl group of R ₇ and R ₈ are each independently selected from the group consisting of an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , and a heteroaryl group of 5 to 60 nuclear atoms. When substituted or unsubstituted with more than one type of substituent and substituted with multiple substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group. is selected from the group consisting of,

Of R ₇ and R ₈ Phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group, and dibenzothiophenyl group are each independently an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ and heteroaryl groups having 5 to 60 nuclear atoms. When substituted or unsubstituted with one or more substituents selected from the group consisting of a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ and R ₈ are each independently a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, a carbazolyl group, a fluorenyl group, and a dibenzothiophenyl group. is selected from the group consisting of,

Of R ₇ and R ₈ Phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group are each independently methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, When unsubstituted or substituted with one or more substituents selected from the group consisting of pyridinyl group, pyrimidinyl group, dibenzofuranyl group, carbazolyl group, fluorenyl group and dibenzothiophenyl group, and substituted with a plurality of substituents, these are the same or different from each other.

The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

The compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ), etc.). The detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples described later.

2. Organic electric field light emitting element

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic material layers has the formula above. It may include a compound represented by 1.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, but referring to Figure 1 as an example, for example, an anode 10 and a cathode 20 facing each other, and the anode 10 and the cathode ( 20) and includes an organic layer 30 located between them. Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.

Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode. An electron injection layer 36 may be further included between (20).

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 not only improves the interface characteristics between ITO used as the anode and the organic material used as the hole transport layer 31. Rather, it is a layer that is applied on top of the ITO, which has an uneven surface, and functions to smooth the surface of the ITO. It can be used without particular restrictions as long as it is commonly used in the art. For example, an amine compound can be used. It is not limited to this.

In addition, the electron injection layer 36 is a layer that is laminated on top of the electron transport layer 34 to facilitate electron injection from the cathode and ultimately improve power efficiency, and is commonly used in the art. Any material that can be used can be used without particular restrictions. For example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO can be used.

In addition, although not shown in the drawings, in the present invention, a light-emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light-emitting layer 32. The light-emitting auxiliary layer may serve to transport holes to the light-emitting layer 32 and adjust the thickness of the organic layer 30. The light emitting auxiliary layer may include a hole transport material and may be made of the same material as the hole transport layer 31.

In addition, although not shown in the drawings, in the present invention, a lifespan improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light-emitting device to the light-emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer and cannot diffuse or move to the electron transport layer, thereby limiting the holes to the light-emitting layer. . This function of limiting holes to the light-emitting layer prevents holes from diffusing into the electron transport layer, which moves electrons through reduction, and suppresses the phenomenon of lifespan reduction through irreversible decomposition reactions due to oxidation, contributing to improving the lifespan of organic light-emitting devices. You can.

The compound of the present invention has a nitrogen-containing heterocycle (e.g., pyridine group, Its structural characteristic is that it combines an electron withdrawing group (EWG) with high electron absorption, such as a pyrimidine group, triazine group, etc., and has the characteristics of low voltage operation and high refractive index, resulting in physical characteristics of high efficiency and long lifespan.

For this reason, since the compound represented by Formula 1, which is the representative claimed structure of the present invention, has excellent light-emitting properties, any one of the organic material layers of the organic electroluminescent device: a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. It can be used as a material. Preferably, it can be used as a hole transport layer and hole auxiliary transport layer material.

In addition, in the present invention, the organic electroluminescent device not only includes an anode, one or more organic material layers, and a cathode sequentially stacked as described above, but may additionally include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic layers (e.g., electron transport auxiliary layer) includes the compound represented by Formula 1 above. It can be manufactured by forming other organic layers and electrodes.

The organic material layer may be formed by vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

In addition, the anode material may be made of, for example, a conductor with a high work function to facilitate hole injection, and may include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

In addition, the cathode material can be made of a conductor with a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. Same metals or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples only illustrate the present invention, and the present invention is not limited by the following examples.

Example

[Preparation example 1]

Synthesis of 1-(3-(dibenzo[b,d]furan-4-yl)phenyl)-9H-carbazole

1-Bromo-9H-carbazole (50 g, 203 mmol), 2-(3-(dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl under nitrogen stream. -1,3,2-dioxabororane (82.6g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/ H2O was added and stirred at 100°C for 8 hours. After completion of the reaction, the extract was extracted with methylene chloride, concentrated under reduced pressure, and then subjected to column chromatography to obtain 73g (88%) of the target compound.

GC-Mass (theoretical value: 409.15 g/mol, measured value: 409.49 g/mol)

1H-NMR: 11.7 (br, 1H), 8.29(d, 1H), 8.19(d, 1H), 8.06~7.98(m, 5H), 7.63~7.20(m, 11H)

[Preparation example 2]

Synthesis of 1-(3-(dibenzo[b,d]furan-3-yl)phenyl)-9H-carbazole

Except for using 2-(3-(dibenzo[b,d]furan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 409.15 g/mol, measured value: 409.49 g/mol)

[Preparation example 3]

Synthesis of 1-(3-(dibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole

Except for using 2-(3-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 409.15 g/mol, measured value: 409.49 g/mol)

[Preparation example 4]

Synthesis of 1-(3-(dibenzo[b,d]furan-1-yl)phenyl)-9H-carbazole

Except for using 2-(3-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 409.15 g/mol, measured value: 409.49 g/mol)

[Preparation example 5]

Synthesis of 1-(3-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenyl-9H-carbazole

The same procedure as [Preparation Example 1] was performed except that 1-bromo-6-phenyl-9H-carbazole was used as a reactant to obtain 68 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 6]

Synthesis of 1-(3-(dibenzo[b,d]furan-3-yl)phenyl)-6-phenyl-9H-carbazole

The same procedure as [Preparation Example 2] was performed except that 1-bromo-6-phenyl-9H-carbazole was used as a reactant to obtain 75 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 7]

Synthesis of 1-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-9H-carbazole

70g of the target compound was obtained by performing the same procedure as [Preparation Example 3] except that 1-bromo-6-phenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 8]

Synthesis of 1-(3-(dibenzo[b,d]furan-1-yl)phenyl)-6-phenyl-9H-carbazole

The same procedure as [Preparation Example 4] was performed except that 1-bromo-6-phenyl-9H-carbazole was used as a reactant to obtain 69 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 9]

Synthesis of 1-(3-(dibenzo[b,d]furan-4-yl)phenyl)-3-phenyl-9H-carbazole

The same procedure as [Preparation Example 1] was performed except that 1-bromo-3-phenyl-9H-carbazole was used as a reactant to obtain 68 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 10]

Synthesis of 1-(3-(dibenzo[b,d]furan-3-yl)phenyl)-3-phenyl-9H-carbazole

75 g of the target compound was obtained by performing the same procedure as [Preparation Example 2] except that 1-bromo-3-phenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 11]

Synthesis of 1-(3-(dibenzo[b,d]furan-2-yl)phenyl)-3-phenyl-9H-carbazole

70 g of the target compound was obtained by performing the same procedure as [Preparation Example 3] except that 1-bromo-3-phenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 12]

Synthesis of 1-(3-(dibenzo[b,d]furan-1-yl)phenyl)-3-phenyl-9H-carbazole

The same procedure as [Preparation Example 4] was performed except that 1-bromo-3-phenyl-9H-carbazole was used as a reactant to obtain 69 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 13]

Synthesis of 1-(3-(dibenzo[b,d]furan-4-yl)phenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole

74g of the target compound was obtained by performing the same procedure as [Preparation Example 1] except that 1-bromo-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. .;

GC-Mass (theoretical value: 575.19 g/mol, measured value: 575.67 g/mol)

[Preparation example 14]

Synthesis of 1-(3-(dibenzo[b,d]furan-3-yl)phenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole

78g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 1-bromo-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. .;

GC-Mass (theoretical value: 575.19 g/mol, measured value: 575.67 g/mol)

[Preparation example 15]

Synthesis of 1-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole

73g of the target compound was obtained by performing the same procedure as [Preparation Example 3] except that 1-bromo-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. .;

GC-Mass (theoretical value: 575.19 g/mol, measured value: 575.67 g/mol)

[Preparation example 16]

Synthesis of 1-(3-(dibenzo[b,d]furan-1-yl)phenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole

71g of the target compound was obtained by performing the same process as [Preparation Example 4] except that 1-bromo-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. .;

GC-Mass (theoretical value: 575.19 g/mol, measured value: 575.67 g/mol)

[Preparation example 17]

Synthesis of 8-(3-(dibenzo[b,d]furan-4-yl)phenyl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 1] was performed except that 8-bromo-9H-3,9'-bicarbazole was used as a reactant to obtain 76 g of the target compound;

GC-Mass (theoretical value: 574.20 g/mol, measured value: 574.68 g/mol)

[Preparation example 18]

Synthesis of 8-(3-(dibenzo[b,d]furan-3-yl)phenyl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 2] was performed except that 8-bromo-9H-3,9'-bicarbazole was used as a reactant to obtain 72 g of the target compound;

GC-Mass (theoretical value: 574.20 g/mol, measured value: 574.68 g/mol)

[Preparation example 19]

Synthesis of 8-(3-(dibenzo[b,d]furan-2-yl)phenyl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 3] was performed except that 8-bromo-9H-3,9'-bicarbazole was used as a reactant to obtain 75 g of the target compound;

GC-Mass (theoretical value: 574.20 g/mol, measured value: 574.68 g/mol)

[Preparation example 20]

Synthesis of 8-(3-(dibenzo[b,d]furan-1-yl)phenyl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 4] was performed except that 8-bromo-9H-3,9'-bicarbazole was used as a reactant to obtain 69 g of the target compound;

GC-Mass (theoretical value: 574.20 g/mol, measured value: 574.68 g/mol)

[Preparation example 21]

Synthesis of 8-(3-(dibenzo[b,d]furan-4-yl)phenyl)-7H-benzo[c]carbazole

The same procedure as [Preparation Example 1] was performed except that 8-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 76 g of the target compound;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 22]

Synthesis of 8-(3-(dibenzo[b,d]furan-3-yl)phenyl)-7H-benzo[c]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 8-bromo-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 23]

Synthesis of 8-(3-(dibenzo[b,d]furan-2-yl)phenyl)-7H-benzo[c]carbazole

73g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 8-bromo-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 24]

Synthesis of 8-(3-(dibenzo[b,d]furan-1-yl)phenyl)-7H-benzo[c]carbazole

The same process as [Preparation Example 4] was performed except that 8-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 77g of the target compound;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 25]

Synthesis of 4-(3-(dibenzo[b,d]furan-4-yl)phenyl)-5H-benzo[b]carbazole

The same procedure as [Preparation Example 1] was performed except that 4-bromo-5H-benzo[b]carbazole was used as a reactant to obtain 76 g of the target compound;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 26]

Synthesis of 4-(3-(dibenzo[b,d]furan-3-yl)phenyl)-5H-benzo[b]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 4-bromo-5H-benzo[b]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 27]

Synthesis of 4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-5H-benzo[b]carbazole

73 g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 4-bromo-5H-benzo[b]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 28]

Synthesis of 4-(3-(dibenzo[b,d]furan-1-yl)phenyl)-5H-benzo[b]carbazole

The same procedure as [Preparation Example 4] was performed except that 4-bromo-5H-benzo[b]carbazole was used as a reactant to obtain 77 g of the target compound;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 29]

Synthesis of 10-(3-(dibenzo[b,d]furan-4-yl)phenyl)-11H-benzo[a]carbazole

76 g of the target compound was obtained by performing the same process as [Preparation Example 1] except that 10-bromo-11H-benzo[a]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 30]

Synthesis of 10-(3-(dibenzo[b,d]furan-3-yl)phenyl)-11H-benzo[a]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 10-bromo-11H-benzo[a]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 31]

Synthesis of 10-(3-(dibenzo[b,d]furan-2-yl)phenyl)-11H-benzo[a]carbazole

73g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 10-bromo-11H-benzo[a]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 32]

Synthesis of 10-(3-(dibenzo[b,d]furan-1-yl)phenyl)-11H-benzo[a]carbazole

The same process as [Preparation Example 4] was performed except that 10-bromo-11H-benzo[a]carbazole was used as a reactant to obtain 77 g of the target compound;

GC-Mass (theoretical value: 459.15 g/mol, measured value: 459.55 g/mol)

[Preparation example 33]

Synthesis of 10-(3-(dibenzo[b,d]furan-4-yl)phenyl)-9H-dibenzo[a,c]carbazole

The same process as [Preparation Example 1] was performed except that 10-bromo-9H-dibenzo[a,c]carbazole was used as a reactant to obtain 76g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 34]

Synthesis of 10-(3-(dibenzo[b,d]furan-3-yl)phenyl)-9H-dibenzo[a,c]carbazole

The same procedure as [Preparation Example 2] was performed except that 10-bromo-9H-dibenzo[a,c]carbazole was used as a reactant to obtain 72 g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 35]

Synthesis of 10-(3-(dibenzo[b,d]furan-2-yl)phenyl)-9H-dibenzo[a,c]carbazole

The same process as [Preparation Example 3] was performed except that 10-bromo-9H-dibenzo[a,c]carbazole was used as a reactant to obtain 73g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 36]

Synthesis of 10-(3-(dibenzo[b,d]furan-1-yl)phenyl)-9H-dibenzo[a,c]carbazole

The same process as [Preparation Example 4] was performed except that 10-bromo-9H-dibenzo[a,c]carbazole was used as a reactant to obtain 77g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 37]

Synthesis of 1-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

77g of the target compound was obtained by performing the same procedure as [Preparation Example 1] except that 1-(3-bromophenyl)-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 38]

Synthesis of 1-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

The same process as [Preparation Example 2] was performed except that 1-(3-bromophenyl)-9H-carbazole was used as a reactant to obtain 73 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 39]

Synthesis of 1-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

71 g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 1-(3-bromophenyl)-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 40]

Synthesis of 1-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

The same procedure as [Preparation Example 4] was performed except that 1-(3-bromophenyl)-9H-carbazole was used as a reactant to obtain 73 g of the target compound;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 41]

Synthesis of 1-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

The same procedure as [Preparation Example 1] was performed except that 1-(3-bromophenyl)-6-phenyl-9H-carbazole was used as a reactant to obtain 68 g of the target compound;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 42]

Synthesis of 1-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

The same procedure as [Preparation Example 2] was performed except that 1-(3-bromophenyl)-6-phenyl-9H-carbazole was used as a reactant to obtain 75 g of the target compound;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 43]

Synthesis of 1-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

70 g of the target compound was obtained by performing the same procedure as in [Preparation Example 3], except that 1-(3-bromophenyl)-6-phenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 44]

Synthesis of 1-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

The same procedure as [Preparation Example 4] was performed except that 1-(3-bromophenyl)-6-phenyl-9H-carbazole was used as a reactant to obtain 69 g of the target compound;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 45]

Synthesis of 1-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

The same procedure as [Preparation Example 1] was performed except that 1-(3-bromophenyl)-3-phenyl-9H-carbazole was used as a reactant to obtain 68 g of the target compound;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 46]

Synthesis of 1-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

75 g of the target compound was obtained by performing the same procedure as in [Preparation Example 2] except that 1-(3-bromophenyl)-3-phenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 47]

Synthesis of 1-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

70 g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 1-(3-bromophenyl)-3-phenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 48]

Synthesis of 1-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

The same process as [Preparation Example 4] was performed except that 1-(3-bromophenyl)-3-phenyl-9H-carbazole was used as a reactant to obtain 69 g of the target compound;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation example 49]

1-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-6-(dibenzo[b,d]furan-4- 1) Synthesis of -9H-carbazole

The same process as [Preparation Example 1] was performed except that 1-(3-bromophenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. 74g of the target compound was obtained;

GC-Mass (theoretical value: 651.22 g/mol, measured value: 651.77 g/mol)

[Preparation example 50]

1-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-6-(dibenzo[b,d]furan-4- 1) Synthesis of -9H-carbazole

The same process as [Preparation Example 2] was performed except that 1-(3-bromophenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. 78g of the target compound was obtained;

GC-Mass (theoretical value: 651.22 g/mol, measured value: 651.77 g/mol)

[Preparation example 51]

1-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-6-(dibenzo[b,d]furan-4- 1) Synthesis of -9H-carbazole

The same process as [Preparation Example 3] was performed except that 1-(3-bromophenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. 73g of the target compound was obtained;

GC-Mass (theoretical value: 651.22 g/mol, measured value: 651.77 g/mol)

[Preparation example 52]

1-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-6-(dibenzo[b,d]furan-4- 1) Synthesis of -9H-carbazole

The same process as [Preparation Example 4] was performed except that 1-(3-bromophenyl)-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole was used as a reactant. 71g of the target compound was obtained;

GC-Mass (theoretical value: 651.22 g/mol, measured value: 651.77 g/mol)

[Preparation example 53]

Synthesis of 8-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 1] was performed except that 8-(3-bromophenyl)-9H-3,9'-bicarbazole was used as a reactant to obtain 76 g of the target compound;

GC-Mass (theoretical value: 650.24 g/mol, measured value: 650.78 g/mol)

[Preparation example 54]

Synthesis of 8-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 8-(3-bromophenyl)-9H-3,9'-bicarbazole was used as a reactant;

GC-Mass (theoretical value: 650.24 g/mol, measured value: 650.78 g/mol)

[Preparation example 55]

Synthesis of 8-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 3] was performed except that 8-(3-bromophenyl)-9H-3,9'-bicarbazole was used as a reactant to obtain 75 g of the target compound;

GC-Mass (theoretical value: 650.24 g/mol, measured value: 650.78 g/mol)

[Preparation example 56]

Synthesis of 8-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

The same procedure as [Preparation Example 4] was performed except that 8-(3-bromophenyl)-9H-3,9'-bicarbazole was used as a reactant to obtain 69 g of the target compound;

GC-Mass (theoretical value: 650.24 g/mol, measured value: 650.78 g/mol)

[Preparation example 57]

Synthesis of 8-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

76 g of the target compound was obtained by performing the same procedure as [Preparation Example 1] except that 8-(3-bromophenyl)-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 58]

Synthesis of 8-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 8-(3-bromophenyl)-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 59]

Synthesis of 8-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

The same procedure as [Preparation Example 3] was performed except that 8-(3-bromophenyl)-7H-benzo[c]carbazole was used as a reactant to obtain 73 g of the target compound;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 60]

Synthesis of 8-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

77 g of the target compound was obtained by performing the same procedure as [Preparation Example 4] except that 8-(3-bromophenyl)-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 61]

Synthesis of 4-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

76 g of the target compound was obtained by performing the same procedure as [Preparation Example 1] except that 4-(3-bromophenyl)-5H-benzo[b]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 62]

Synthesis of 4-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 4-(3-bromophenyl)-5H-benzo[b]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 63]

Synthesis of 4-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

73 g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 4-(3-bromophenyl)-5H-benzo[b]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 64]

Synthesis of 4-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

77 g of the target compound was obtained by performing the same process as [Preparation Example 4] except that 4-(3-bromophenyl)-5H-benzo[b]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 65]

Synthesis of 10-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

76 g of the target compound was obtained by performing the same process as [Preparation Example 1] except that 10-(3-bromophenyl)-11H-benzo[a]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 66]

Synthesis of 10-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 10-(3-bromophenyl)-11H-benzo[a]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 67]

Synthesis of 10-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

The same process as [Preparation Example 3] was performed except that 10-(3-bromophenyl)-11H-benzo[a]carbazole was used as a reactant to obtain 73 g of the target compound.

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 68]

Synthesis of 10-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

77 g of the target compound was obtained by performing the same process as [Preparation Example 4] except that 10-(3-bromophenyl)-11H-benzo[a]carbazole was used as a reactant;

GC-Mass (theoretical value: 535.19 g/mol, measured value: 535.65 g/mol)

[Preparation example 69]

Synthesis of 10-(3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

The same procedure as [Preparation Example 1] was performed except that 10-(3-bromophenyl)-9H-dibenzo[a,c]carbazole was used as a reactant to obtain 76 g of the target compound;

GC-Mass (theoretical value: 585.21 g/mol, measured value: 585.71 g/mol)

[Preparation example 70]

Synthesis of 10-(3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

72 g of the target compound was obtained by performing the same process as [Preparation Example 2] except that 10-(3-bromophenyl)-9H-dibenzo[a,c]carbazole was used as a reactant;

GC-Mass (theoretical value: 585.21 g/mol, measured value: 585.71 g/mol)

[Preparation example 71]

Synthesis of 10-(3'-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

73 g of the target compound was obtained by performing the same process as [Preparation Example 3] except that 10-(3-bromophenyl)-9H-dibenzo[a,c]carbazole was used as a reactant;

GC-Mass (theoretical value: 585.21 g/mol, measured value: 585.71 g/mol)

[Preparation example 72]

Synthesis of 10-(3'-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

77 g of the target compound was obtained by performing the same process as [Preparation Example 4] except that 10-(3-bromophenyl)-9H-dibenzo[a,c]carbazole was used as a reactant;

GC-Mass (theoretical value: 585.21 g/mol, measured value: 585.71 g/mol)

[Preparation example 73]

Synthesis of 1-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9H-carbazole

Except for using 2-(4-(dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 409.19 g/mol, measured value: 409.49 g/mol)

[Preparation example 74]

Synthesis of 1-(5-(dibenzo[b,d]furan-4-yl)naphthalen-1-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-4-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane The same process as [Preparation Example 1] was performed except that 77g of the target compound was obtained;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 75]

Synthesis of 1-(4-(dibenzo[b,d]furan-3-yl)phenyl)-9H-carbazole

Except for using 2-(4-(dibenzo[b,d]furan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 409.19 g/mol, measured value: 409.49 g/mol)

[Preparation example 76]

Synthesis of 1-(5-(dibenzo[b,d]furan-3-yl)naphthalen-1-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-3-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane The same process as [Preparation Example 1] was performed except that 77g of the target compound was obtained;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 77]

Synthesis of 1-(4-(dibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole

Except for using 2-(4-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 409.19 g/mol, measured value: 409.49 g/mol)

[Preparation example 78]

Synthesis of 1-(5-(dibenzo[b,d]furan-2-yl)naphthalen-1-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-2-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane The same process as [Preparation Example 1] was performed except that 77g of the target compound was obtained;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 79]

Synthesis of 1-(4-(dibenzo[b,d]furan-1-yl)phenyl)-9H-carbazole

Except for using 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane as a reactant. Then, the same process as [Preparation Example 1] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 409.19 g/mol, measured value: 409.49 g/mol)

[Preparation example 80]

Synthesis of 1-(5-(dibenzo[b,d]furan-1-yl)naphthalen-1-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-1-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane The same process as [Preparation Example 1] was performed except that 77g of the target compound was obtained;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 81]

Synthesis of 8-(4-(dibenzo[b,d]furan-4-yl)phenyl)-7H-benzo[c]carbazole

79g of the target compound was obtained by performing the same process as [Preparation Example 21] except that 8-bromo-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 82]

Synthesis of 8-(5-(dibenzo[b,d]furan-4-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

The same process as [Preparation Example 21] was performed except that 8-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 77g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 83]

Synthesis of 8-(4-(dibenzo[b,d]furan-3-yl)phenyl)-7H-benzo[c]carbazole

79g of the target compound was obtained by performing the same process as [Preparation Example 21] except that 8-bromo-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 84]

Synthesis of 8-(5-(dibenzo[b,d]furan-3-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

The same process as [Preparation Example 21] was performed except that 8-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 77g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 85]

Synthesis of 8-(4-(dibenzo[b,d]furan-2-yl)phenyl)-7H-benzo[c]carbazole

79g of the target compound was obtained by performing the same process as [Preparation Example 21] except that 8-bromo-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 86]

Synthesis of 8-(5-(dibenzo[b,d]furan-2-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

The same process as [Preparation Example 21] was performed except that 8-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 77g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 87]

Synthesis of 8-(4-(dibenzo[b,d]furan-1-yl)phenyl)-7H-benzo[c]carbazole

79g of the target compound was obtained by performing the same process as [Preparation Example 21] except that 8-bromo-7H-benzo[c]carbazole was used as a reactant;

GC-Mass (theoretical value: 459.16 g/mol, measured value: 459.55 g/mol)

[Preparation example 88]

Synthesis of 8-(5-(dibenzo[b,d]furan-1-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

The same process as [Preparation Example 21] was performed except that 8-bromo-7H-benzo[c]carbazole was used as a reactant to obtain 77g of the target compound;

GC-Mass (theoretical value: 509.18 g/mol, measured value: 509.61 g/mol)

[Preparation example 89]

Synthesis of 1-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 1] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 90]

Synthesis of 1-(5-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 1] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation example 91]

Synthesis of 1-(5-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 1] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation Example 92]

Synthesis of 1-(5-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-1-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 1] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 485.18 g/mol, measured value: 485.59 g/mol)

[Preparation Example 93]

Synthesis of 1-(5-(6-phenyldibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 4,4,5,5-tetramethyl-2-(5-(6-phenyldibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl) 79g of the target compound was obtained by performing the same process as [Preparation Example 1] except that -1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 561.21 g/mol, measured value: 561.68 g/mol)

[Preparation Example 94]

Synthesis of 1-(5-([4,4'-vidibenzo[b,d]furan]-6-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-([4,4'-vidibenzo[b,d]furan]-6-yl)-[1,1'-biphenyl]-3-yl)-4,4,5, 79g of the target compound was obtained by performing the same procedure as [Preparation Example 1] except that 5-tetramethyl-1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 651.22 g/mol, measured value: 651.77 g/mol)

[Preparation example 95]

6-(dibenzo[b,d]furan-4-yl)-1-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl )-9H-carbazole synthesis

As a reactant, 2-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 13] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 651.22 g/mol, measured value: 651.77 g/mol)

[Preparation example 96]

Synthesis of 8-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 17] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 650.24 g/mol, measured value: 650.78 g/mol)

[Preparation example 97]

Synthesis of 8-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 21] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 535.18 g/mol, measured value: 535.65 g/mol)

[Preparation example 98]

Synthesis of 10-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

As a reactant, 2-(5-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1, 79g of the target compound was obtained by performing the same process as [Preparation Example 33] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 585.21 g/mol, measured value: 585.21 g/mol)

[Preparation example 99]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 1] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 425.12 g/mol, measured value: 425.55 g/mol)

[Preparation example 100]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 2] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 425.12 g/mol, measured value: 425.55 g/mol)

[Preparation example 101]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 3] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 425.12 g/mol, measured value: 425.55 g/mol)

[Preparation example 102]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 4] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 425.12 g/mol, measured value: 425.55 g/mol)

[Preparation example 103]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 5] was performed to obtain 68g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 104]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 6] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 105]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 7] was performed to obtain 70g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 106]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. The same process as [Preparation Example 8] was performed except that 69g of the target compound was obtained;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 107]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. The same process as [Preparation Example 9] was performed except that 68 g of the target compound was obtained;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 108]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 10] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 109]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 11] was performed to obtain 70g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 110]

Synthesis of 1-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. The same process as [Preparation Example 12] was performed except that 69g of the target compound was obtained;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 111]

Synthesis of 6-(dibenzo[b,d]furan-4-yl)-1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 13] was performed to obtain 74 g of the target compound;

GC-Mass (theoretical value: 591.17 g/mol, measured value: 591.73 g/mol)

[Preparation example 112]

Synthesis of 6-(dibenzo[b,d]furan-3-yl)-1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 14] was performed to obtain 78g of the target compound;

GC-Mass (theoretical value: 591.17 g/mol, measured value: 591.73 g/mol)

[Preparation example 113]

Synthesis of 6-(dibenzo[b,d]furan-2-yl)-1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 15] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 591.17 g/mol, measured value: 591.73 g/mol)

[Preparation example 114]

Synthesis of 6-(dibenzo[b,d]furan-1-yl)-1-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 16] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 591.17 g/mol, measured value: 591.73 g/mol)

[Preparation example 115]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 17] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 590.18 g/mol, measured value: 590.74 g/mol)

[Preparation example 116]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 18] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 590.18 g/mol, measured value: 590.74 g/mol)

[Preparation example 117]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 19] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 590.18 g/mol, measured value: 590.74 g/mol)

[Preparation example 118]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 20] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 590.18 g/mol, measured value: 590.74 g/mol)

[Preparation example 119]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 21] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 120]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 22] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 121]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 23] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 122]

Synthesis of 8-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 24] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 123]

Synthesis of 4-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 25] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 124]

Synthesis of 4-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 26] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 125]

Synthesis of 4-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 27] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 126]

Synthesis of 4-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 28] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 127]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 29] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 128]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 30] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 129]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 31] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 130]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 32] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 131]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 33] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 132]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 34] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 133]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 35] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 134]

Synthesis of 10-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 36] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 135]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 37] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 136]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 38] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 137]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 39] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 138]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 40] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 139]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. The same process as [Preparation Example 41] was performed except that 68 g of the target compound was obtained;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 140]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 42] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 141]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 43] was performed to obtain 70g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 142]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 44] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 143]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 45] was performed to obtain 68g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 144]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 46] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 145]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 47] was performed to obtain 70g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 146]

Synthesis of 1-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 48] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 147]

6-(dibenzo[b,d]furan-4-yl)-1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3 -1)-9H-carbazole synthesis

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 49] was performed to obtain 74 g of the target compound;

GC-Mass (theoretical value: 667.20 g/mol, measured value: 667.83 g/mol)

[Preparation example 148]

6-(dibenzo[b,d]furan-3-yl)-1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3 -1)-9H-carbazole synthesis

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 50] was performed to obtain 78 g of the target compound;

GC-Mass (theoretical value: 667.20 g/mol, measured value: 667.83 g/mol)

[Preparation example 149]

6-(dibenzo[b,d]furan-2-yl)-1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3 -1)-9H-carbazole synthesis

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 51] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 667.20 g/mol, measured value: 667.83 g/mol)

[Preparation example 150]

6-(dibenzo[b,d]furan-1-yl)-1-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3 -1)-9H-carbazole synthesis

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 52] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 667.20 g/mol, measured value: 667.83 g/mol)

[Preparation example 151]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 53] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 666.21 g/mol, measured value: 666.84 g/mol)

[Preparation example 152]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 54] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 666.21 g/mol, measured value: 666.84 g/mol)

[Preparation example 153]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 55] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 666.21 g/mol, measured value: 666.84 g/mol)

[Preparation example 154]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 56] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 666.21 g/mol, measured value: 666.84 g/mol)

[Preparation example 155]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 57] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 156]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 58] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 157]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 59] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 158]

Synthesis of 8-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 60] was performed to obtain 77 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 159]

Synthesis of 4-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 61] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 160]

Synthesis of 4-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 62] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 161]

Synthesis of 4-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 63] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 162]

Synthesis of 4-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 64] was performed to obtain 77 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 163]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 65] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 164]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 66] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 165]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 67] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 166]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 68] was performed to obtain 77 g of the target compound;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 167]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 69] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 601.19 g/mol, measured value: 601.77 g/mol)

[Preparation example 168]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 70] was performed to obtain 72 g of the target compound;

GC-Mass (theoretical value: 601.19 g/mol, measured value: 601.77 g/mol)

[Preparation example 169]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 71] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 601.19 g/mol, measured value: 601.77 g/mol)

[Preparation example 170]

Synthesis of 10-(3'-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

2-(3-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 72] was performed to obtain 77 g of the target compound;

GC-Mass (theoretical value: 601.19 g/mol, measured value: 601.77 g/mol)

[Preparation example 171]

Synthesis of 1-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole

2-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 73] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 425.16 g/mol, measured value: 425.55 g/mol)

[Preparation example 172]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-4-yl)naphthalen-1-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 74] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 173]

Synthesis of 1-(4-(dibenzo[b,d]thiophen-3-yl)phenyl)-9H-carbazole

2-(4-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 75] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 425.16 g/mol, measured value: 425.55 g/mol)

[Preparation example 174]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-3-yl)naphthalen-1-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-3-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 76] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 175]

Synthesis of 1-(4-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-carbazole

2-(4-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 77] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 425.16 g/mol, measured value: 425.55 g/mol)

[Preparation example 176]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-2-yl)naphthalen-1-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-2-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant 77g of the target compound was obtained by performing the same process as [Preparation Example 78] except that eggs were used;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 177]

Synthesis of 1-(4-(dibenzo[b,d]thiophen-1-yl)phenyl)-9H-carbazole

2-(4-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 79] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 425.16 g/mol, measured value: 425.55 g/mol)

[Preparation example 178]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-1-yl)naphthalen-1-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-1-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 80] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.61 g/mol)

[Preparation example 179]

Synthesis of 8-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 81] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.65 g/mol)

[Preparation example 180]

Synthesis of 8-(5-(dibenzo[b,d]thiophen-4-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 82] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 181]

Synthesis of 8-(4-(dibenzo[b,d]thiophen-3-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(dibenzo[b,d]thiophen-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 83] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.65 g/mol)

[Preparation example 182]

Synthesis of 8-(5-(dibenzo[b,d]thiophen-3-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

2-(5-(dibenzo[b,d]thiophen-3-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 84] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 183]

Synthesis of 8-(4-(dibenzo[b,d]thiophen-2-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(dibenzo[b,d]thiophen-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 85] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.65 g/mol)

[Preparation example 184]

Synthesis of 8-(5-(dibenzo[b,d]thiophen-2-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

2-(5-(dibenzo[b,d]thiophen-2-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 86] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 185]

Synthesis of 8-(4-(dibenzo[b,d]thiophen-1-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that the same process as [Preparation Example 87] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 475.14 g/mol, measured value: 475.65 g/mol)

[Preparation example 186]

Synthesis of 8-(5-(dibenzo[b,d]thiophen-1-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

2-(5-(dibenzo[b,d]thiophen-1-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaboro as reactant The same process as [Preparation Example 88] was performed except that eggs were used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 525.16 g/mol, measured value: 525.67 g/mol)

[Preparation example 187]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 89] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 188]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 90] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 189]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 91] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 190]

Synthesis of 1-(5-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(5-(dibenzo[b,d]thiophen-1-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 92] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 501.16 g/mol, measured value: 501.65 g/mol)

[Preparation example 191]

Synthesis of 1-(5-(6-phenyldibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 4,4,5,5-tetramethyl-2-(5-(6-phenyldibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl ) The same process as [Preparation Example 93] was performed except that -1,3,2-dioxabororane was used to obtain 79 g of the target compound;

GC-Mass (theoretical value: 577.19 g/mol, measured value: 577.75 g/mol)

[Preparation example 192]

1-(5-(6-(dibenzo[b,d]furan-4-yl)dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl )-9H-carbazole synthesis

As a reactant, 2-(5-(6-(dibenzo[b,d]furan-4-yl)dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3 -1)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used, and the same procedure as [Preparation Example 94] was performed to obtain 79 g of the target compound;

GC-Mass (theoretical value: 667.20 g/mol, measured value: 667.83 g/mol)

[Preparation example 193]

6-(dibenzo[b,d]furan-4-yl)-1-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3- 1) Synthesis of -9H-carbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 95] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 667.20 g/mol, measured value: 667.83 g/mol)

[Preparation example 194]

Synthesis of 8-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 96] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 666.21 g/mol, measured value: 666.84 g/mol)

[Preparation example 195]

Synthesis of 8-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 97] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 551.17 g/mol, measured value: 551.71 g/mol)

[Preparation example 196]

Synthesis of 10-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

2-(5-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1 as reactant , 79g of the target compound was obtained by performing the same process as [Preparation Example 98] except that 3,2-dioxabororane was used;

GC-Mass (theoretical value: 601.19 g/mol, measured value: 601.77 g/mol)

[Preparation example 197]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 1] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 435.20 g/mol, measured value: 435.57 g/mol)

[Preparation example 198]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 3] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 435.20 g/mol, measured value: 435.57 g/mol)

[Preparation example 199]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 4] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 435.20 g/mol, measured value: 435.57 g/mol)

[Preparation example 200]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 5] was performed to obtain 68g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 201]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 7] was performed to obtain 70g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 202]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-6-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 8] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 203]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 9] was performed to obtain 68g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 204]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. 70g of the target compound was obtained by performing the same process as [Preparation Example 11] except that;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 205]

Synthesis of 1-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-3-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 12] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 206]

Synthesis of 6-(dibenzo[b,d]furan-4-yl)-1-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 13] was performed to obtain 74 g of the target compound;

GC-Mass (theoretical value: 601.24 g/mol, measured value: 601.75 g/mol)

[Preparation example 207]

Synthesis of 6-(dibenzo[b,d]furan-4-yl)-1-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 15] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 601.24 g/mol, measured value: 601.75 g/mol)

[Preparation example 208]

Synthesis of 6-(dibenzo[b,d]furan-4-yl)-1-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 16] was performed to obtain 71g of the target compound;

GC-Mass (theoretical value: 601.24 g/mol, measured value: 601.75 g/mol)

[Preparation example 209]

Synthesis of 8-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 17] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 600.26 g/mol, measured value: 600.77 g/mol)

[Preparation example 210]

Synthesis of 8-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 19] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 600.26 g/mol, measured value: 600.77 g/mol)

[Preparation example 211]

Synthesis of 8-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-9H-3,9'-bicarbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 20] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 600.26 g/mol, measured value: 600.77 g/mol)

[Preparation example 212]

Synthesis of 8-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 21] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 213]

Synthesis of 8-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 23] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 214]

Synthesis of 8-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-7H-benzo[c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 24] was performed to obtain 77 g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 215]

Synthesis of 4-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 25] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 216]

Synthesis of 4-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 27] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 217]

Synthesis of 4-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-5H-benzo[b]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 28] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 218]

Synthesis of 10-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 29] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 219]

Synthesis of 10-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 31] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 220]

Synthesis of 10-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-11H-benzo[a]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 32] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 221]

Synthesis of 10-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 33] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 535.23 g/mol, measured value: 535.69 g/mol)

[Preparation example 222]

Synthesis of 10-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 35] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 535.23 g/mol, measured value: 535.69 g/mol)

[Preparation example 223]

Synthesis of 10-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-9H-dibenzo[a,c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 36] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 535.23 g/mol, measured value: 535.69 g/mol)

[Preparation example 224]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 37] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 225]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 39] was performed to obtain 71 g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 226]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 40] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 227]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 41] was performed to obtain 68g of the target compound;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 228]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. 70g of the target compound was obtained by performing the same process as [Preparation Example 43] except that;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 229]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 44] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 230]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 45] was performed to obtain 68g of the target compound;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 231]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 47] was performed to obtain 70g of the target compound;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 232]

Synthesis of 1-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-3-phenyl-9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 48] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 233]

6-(dibenzo[b,d]furan-4-yl)-1-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]- 3-day) Synthesis of -9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 49] was performed to obtain 74 g of the target compound;

GC-Mass (theoretical value: 677.27 g/mol, measured value: 677.85 g/mol)

[Preparation example 234]

6-(dibenzo[b,d]furan-4-yl)-1-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]- 3-day) Synthesis of -9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 51] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 677.27 g/mol, measured value: 677.85 g/mol)

[Preparation example 235]

6-(dibenzo[b,d]furan-4-yl)-1-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]- 3-day) Synthesis of -9H-carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 52] was performed to obtain 71 g of the target compound;

GC-Mass (theoretical value: 677.27 g/mol, measured value: 677.85 g/mol)

[Preparation example 236]

Synthesis of 8-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 53] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 676.29 g/mol, measured value: 676.85 g/mol)

[Preparation example 237]

Synthesis of 8-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 55] was performed to obtain 75 g of the target compound;

GC-Mass (theoretical value: 676.29 g/mol, measured value: 676.85 g/mol)

[Preparation example 238]

Synthesis of 8-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 56] was performed to obtain 69g of the target compound;

GC-Mass (theoretical value: 676.29 g/mol, measured value: 676.85 g/mol)

[Preparation example 239]

Synthesis of 8-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 57] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 240]

Synthesis of 8-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 59] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 241]

Synthesis of 8-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 60] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 242]

Synthesis of 4-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 61] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 243]

Synthesis of 4-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 63] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 244]

Synthesis of 4-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 64] was performed to obtain 77 g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 245]

Synthesis of 10-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 65] was performed to obtain 76 g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 246]

Synthesis of 10-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 67] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 247]

Synthesis of 10-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-11H-benzo[a]carbazole

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 68] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 248]

10-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole synthesis

2-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 69] was performed to obtain 76g of the target compound;

GC-Mass (theoretical value: 611.26 g/mol, measured value: 611.79 g/mol)

[Preparation example 249]

10-(3'-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole synthesis

2-(3-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 71] was performed to obtain 73g of the target compound;

GC-Mass (theoretical value: 611.26 g/mol, measured value: 611.79 g/mol)

[Preparation example 250]

10-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole synthesis

2-(3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 72] was performed to obtain 77g of the target compound;

GC-Mass (theoretical value: 611.26 g/mol, measured value: 611.79 g/mol)

[Preparation example 251]

Synthesis of 1-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9H-carbazole

2-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 73] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 435.20 g/mol, measured value: 435.57 g/mol)

[Preparation example 252]

Synthesis of 1-(5-(9,9-dimethyl-9H-fluoren-2-yl)naphthalen-1-yl)-9H-carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabor 77 g of the target compound was obtained by performing the same process as [Preparation Example 74] except that loran was used;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 253]

Synthesis of 1-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-9H-carbazole

2-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 77] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 435.20 g/mol, measured value: 435.57 g/mol)

[Preparation example 254]

Synthesis of 1-(5-(9,9-dimethyl-9H-fluoren-3-yl)naphthalen-1-yl)-9H-carbazole

2-(5-(9,9-dimethyl-9H-fluoren-3-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabor as reactant 77g of the target compound was obtained by performing the same process as [Preparation Example 78] except that lorane was used;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 255]

Synthesis of 1-(4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-9H-carbazole

2-(4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 79] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 435.20 g/mol, measured value: 435.57 g/mol)

[Preparation example 256]

Synthesis of 1-(5-(9,9-dimethyl-9H-fluoren-4-yl)naphthalen-1-yl)-9H-carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-4-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabor The same process as [Preparation Example 80] was performed except that loran was used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 257]

Synthesis of 8-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 81] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 258]

Synthesis of 8-(5-(9,9-dimethyl-9H-fluoren-2-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabor The same process as [Preparation Example 82] was performed except that lorane was used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 535.23 g/mol, measured value: 535.69 g/mol)

[Preparation example 259]

Synthesis of 8-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 85] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 260]

Synthesis of 8-(5-(9,9-dimethyl-9H-fluoren-3-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-3-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabor The same process as [Preparation Example 86] was performed except that lorane was used to obtain 77 g of the target compound;

GC-Mass (theoretical value: 535.23 g/mol, measured value: 535.69 g/mol)

[Preparation example 261]

Synthesis of 8-(4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-7H-benzo[c]carbazole

2-(4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used as a reactant. Except that, the same process as [Preparation Example 87] was performed to obtain 79g of the target compound;

GC-Mass (theoretical value: 485.21 g/mol, measured value: 485.63 g/mol)

[Preparation example 262]

Synthesis of 8-(5-(9,9-dimethyl-9H-fluoren-4-yl)naphthalen-1-yl)-7H-benzo[c]carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-4-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabor 77g of the target compound was obtained by performing the same process as [Preparation Example 88] except that lorane was used;

GC-Mass (theoretical value: 535.23 g/mol, measured value: 535.69 g/mol)

[Preparation example 263]

Synthesis of 1-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 89] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 264]

Synthesis of 1-(5-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 91] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 265]

Synthesis of 1-(5-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 92] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 511.23 g/mol, measured value: 511.67 g/mol)

[Preparation example 266]

Synthesis of 1-(5-(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole

Reactant 2-(5-(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5 -79g of the target compound was obtained by performing the same process as [Preparation Example 93] except that tetramethyl-1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 587.26 g/mol, measured value: 587.77 g/mol)

[Preparation example 267]

1-(5-(7-(dibenzo[b,d]furan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3 -1)-9H-carbazole synthesis

Reactant 2-(5-(7-(dibenzo[b,d]furan-2-yl)-9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl] -3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxabororane was used, and the same procedure as [Preparation Example 94] was performed to obtain 79 g of the target compound. .;

GC-Mass (theoretical value: 677.27 g/mol, measured value: 677.85 g/mol)

[Preparation example 268]

6-(dibenzo[b,d]furan-4-yl)-1-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3 -1)-9H-carbazole synthesis

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 95] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 677.27 g/mol, measured value: 677.85 g/mol)

[Preparation example 269]

Synthesis of 8-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-3,9'-bicarbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 96] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 676.29 g/mol, measured value: 676.86 g/mol)

[Preparation example 270]

Synthesis of 8-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-7H-benzo[c]carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 97] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 561.25 g/mol, measured value: 561.73 g/mol)

[Preparation example 271]

Synthesis of 10-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9H-dibenzo[a,c]carbazole

As a reactant, 2-(5-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl- 79g of the target compound was obtained by performing the same process as [Preparation Example 98] except that 1,3,2-dioxabororane was used;

GC-Mass (theoretical value: 611.26 g/mol, measured value: 611.79 g/mol)

[Synthesis Example 1] Synthesis of Mat 1

Under a nitrogen stream, 250 mL of xylene was added to 6.13 g (14.99 mmol) of [Preparation Example 1] and 5.6 g (17.99 mmol) of 4-bromo-2,6-diphenylpyrimidine. 30.68 g (0.75 mmol) of Pd2(dba), 30.3 g (1.499 mmol) of P(t-Bu), and 3.59 g (37.47 mol) of NaOtBu were added and heated and refluxed at 120°C for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated by adding 500 mL of ammonium chloride aqueous solution to the reaction solution. The mixed solution was extracted with 500 mL of M.C. and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 8.15 g of the target compound (yield 85%). 1H-NMR: 8.55(d, 1H), 8.29(d 1H), 8.19(dd, 2H), 8.08~7.59(m, 8H), 7.73(t, 1H), 8.06~8.05(m, 2H), 7.94 ~7.90(m, 4H), 7.70~7.48(m, 7H), 7.35(t, 1H), 7.24(s, 1H), 7.16(t, 1H); HRMS [M]+:640.23

[Synthesis Example 2] Synthesis of Mat 2

The same process as [Synthesis Example 1] was performed except that 4-([1,1'-biphenyl]-4-yl)-6-bromo-2-phenylpyrimidine was used as a reactant, and the target compound 14.7 got g.; HRMS [M]+: 716.27

[Synthesis Example 3] Synthesis of Mat 3

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that 4-bromo-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine was used as a reactant. .; HRMS [M]+: 717.25

[Synthesis Example 4] Synthesis of Mat 4

The same process as [Synthesis Example 1] was performed except that 4-bromo-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidinepyrimidine was used as a reactant to produce the target compound. 14.7 g was obtained; HRMS [M]+: 730.24

[Synthesis Example 5] Synthesis of Mat 5

Dissolve [Preparation Example 1] (12.24 g, 29.9 mmol) in 100 ml of DMF under a nitrogen stream and then slowly add NaH (1.07 g, 44.9 mmol) dropwise at room temperature. After sufficient stirring for 1 hour, 2-chloro-4,6-diphenyl-1,3,5-triazine (9.6 g, 35.88 mmol) was slowly added. It was stirred at room temperature for 4 hours. After completion of the reaction, the extract was extracted with methylene chloride, concentrated under reduced pressure, and then subjected to column chromatography to obtain 14.56 g (76%) of the target compound. 1H-NMR: 8.55(d, 1H), 8.36(m 4H), 8.98~7.94(m, 6H), 7.73(t, 1H), 7.51~7.31(m, 13H), 7.16(t, 1H); HRMS [M]+:641.23

[Synthesis Example 6] Synthesis of Mat 6

The same process as [Synthesis Example 5] except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used as a reactant. was performed to obtain 14.2 g of the target compound; HRMS [M]+: 717.26

[Synthesis Example 7] Synthesis of Mat 7

[Synthesis By performing the same process as in Example 5, 13.5 g of the target compound was obtained; HRMS [M]+: 767.28

[Synthesis Example 8] Synthesis of Mat 8

The same process as [Synthesis Example 5] was performed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used as a reactant. 14.8g of the target compound was obtained; HRMS [M]+: 731.24

[Synthesis Example 9] Synthesis of Mat 9

The same process as [Synthesis Example 5] was performed except that 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine was used as a reactant. 14.2 g of the target compound was obtained; HRMS [M]+: 717.26

[Synthesis Example 10] Synthesis of Mat 10

Except that 9-(4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazin-2-yl)-9H-carbazole was used as a reactant. The same process as [Synthesis Example 5] was performed to obtain 15.3 g of the target compound; HRMS [M]+: 821.25

[Synthesis Example 11] Synthesis of Mat 11

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that 2-chloro-4-phenylquinazoline was used as a reactant; HRMS [M]+: 614.22

[Synthesis Example 12] Synthesis of Mat 12

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used as a reactant. ; HRMS [M]+: 670.19

[Synthesis Example 13] Synthesis of Mat 13

The same process as [Synthesis Example 5] was performed except that 2-chloro-3-phenylquinoxaline was used as a reactant to obtain 13.3.2 g of the target compound; HRMS [M]+: 614.22

[Synthesis Example 14] Synthesis of Mat 14

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 730.24

[Synthesis Example 15] Synthesis of Mat 15

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 16] Synthesis of Mat 16

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 17] Synthesis of Mat 17

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 18] Synthesis of Mat 18

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 614.22

[Synthesis Example 19] Synthesis of Mat 19

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 730.24

[Synthesis Example 20] Synthesis of Mat 20

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 21] Synthesis of Mat 21

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 22] Synthesis of Mat 22

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 23] Synthesis of Mat 23

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 614.22

[Synthesis Example 24] Synthesis of Mat 24

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 730.24

[Synthesis Example 25] Synthesis of Mat 25

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 26] Synthesis of Mat 26

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 27] Synthesis of Mat 27

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 28] Synthesis of Mat 28

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 614.22

[Synthesis Example 29] Synthesis of Mat 29

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 730.24

[Synthesis Example 30] Synthesis of Mat 30

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 31] Synthesis of Mat 31

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 32] Synthesis of Mat 32

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 897.28

[Synthesis Example 33] Synthesis of Mat 33

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 34] Synthesis of Mat 34

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 35] Synthesis of Mat 35

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 36] Synthesis of Mat 36

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 37] Synthesis of Mat 37

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 38] Synthesis of Mat 38

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 39] Synthesis of Mat 39

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 40] Synthesis of Mat 40

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 730.24

[Synthesis Example 41] Synthesis of Mat 41

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 42] Synthesis of Mat 42

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 43] Synthesis of Mat 43

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 897.28

[Synthesis Example 44] Synthesis of Mat 44

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 45] Synthesis of Mat 45

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 46] Synthesis of Mat 46

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 47] Synthesis of Mat 47

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 48] Synthesis of Mat 48

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 49] Synthesis of Mat 49

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 50] Synthesis of Mat 50

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 51] Synthesis of Mat 51

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 896.29

[Synthesis Example 52] Synthesis of Mat 52

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 53] Synthesis of Mat 53

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 897.28

[Synthesis Example 54] Synthesis of Mat 54

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 987.29

[Synthesis Example 55] Synthesis of Mat 55

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 56] Synthesis of Mat 56

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 897.28

[Synthesis Example 57] Synthesis of Mat 57

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 58] Synthesis of Mat 58

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 897.28

[Synthesis Example 59] Synthesis of Mat 59

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 60] Synthesis of Mat 60

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 897.28

[Synthesis Example 61] Synthesis of Mat 61

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 62] Synthesis of Mat 62

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 895.30

[Synthesis Example 63] Synthesis of Mat 63

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 806.29

[Synthesis Example 64] Synthesis of Mat 64

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 896.30

[Synthesis Example 65] Synthesis of Mat 65

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 986.31

[Synthesis Example 66] Synthesis of Mat 66

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 779.28

[Synthesis Example 67] Synthesis of Mat 67

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 896.30

[Synthesis Example 68] Synthesis of Mat 68

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 779.28

[Synthesis Example 69] Synthesis of Mat 69

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 896.30

[Synthesis Example 70] Synthesis of Mat 70

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 779.28

[Synthesis Example 71] Synthesis of Mat 71

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 896.30

[Synthesis Example 72] Synthesis of Mat 72

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 779.28

[Synthesis Example 73] Synthesis of Mat 73

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 1] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 74] Synthesis of Mat 74

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 2] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 75] Synthesis of Mat 75

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 3] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 76] Synthesis of Mat 76

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 77] Synthesis of Mat 77

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 691.25

[Synthesis Example 78] Synthesis of Mat 78

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 79] Synthesis of Mat 79

13.5 g of the target compound was obtained by performing the same process as [Synthesis Example 7] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 817.29

[Synthesis Example 80] Synthesis of Mat 80

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 81] Synthesis of Mat 81

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 871.27

[Synthesis Example 82] Synthesis of Mat 82

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 870.28

[Synthesis Example 83] Synthesis of Mat 83

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 84] Synthesis of Mat 84

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 12] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 720.21

[Synthesis Example 85] Synthesis of Mat 85

The same process as [Synthesis Example 13] was performed except that [Preparation Example 21] was used as a reactant to obtain 13.3.2 g of the target compound; HRMS [M]+: 664.23

[Synthesis Example 86] Synthesis of Mat 86

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 87] Synthesis of Mat 87

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 88] Synthesis of Mat 88

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 89] Synthesis of Mat 89

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 871.27

[Synthesis Example 90] Synthesis of Mat 90

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 91] Synthesis of Mat 91

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 92] Synthesis of Mat 92

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 93] Synthesis of Mat 93

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 94] Synthesis of Mat 94

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 871.27

[Synthesis Example 95] Synthesis of Mat 95

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 96] Synthesis of Mat 96

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 97] Synthesis of Mat 97

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 98] Synthesis of Mat 98

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 99] Synthesis of Mat 99

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 871.27

[Synthesis Example 100] Synthesis of Mat 100

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 101] Synthesis of Mat 101

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 102] Synthesis of Mat 102

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 691.25

[Synthesis Example 103] Synthesis of Mat 103

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 104] Synthesis of Mat 104

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 871.27

[Synthesis Example 105] Synthesis of Mat 105

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 106] Synthesis of Mat 106

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 26] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 107] Synthesis of Mat 107

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 26] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 108] Synthesis of Mat 108

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 27] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 109] Synthesis of Mat 109

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 27] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 110] Synthesis of Mat 110

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 28] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 111] Synthesis of Mat 111

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 28] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 112] Synthesis of Mat 112

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 780.26

[Synthesis Example 113] Synthesis of Mat 113

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 691.25

[Synthesis Example 114] Synthesis of Mat 114

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 115] Synthesis of Mat 115

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 871.27

[Synthesis Example 116] Synthesis of Mat 116

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 117] Synthesis of Mat 117

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 30] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 118] Synthesis of Mat 118

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 30] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 119] Synthesis of Mat 119

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 31] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 120] Synthesis of Mat 120

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 31] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 121] Synthesis of Mat 121

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 32] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 122] Synthesis of Mat 122

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 32] was used as a reactant; HRMS [M]+: 664.23

[Synthesis Example 123] Synthesis of Mat 123

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 830.28

[Synthesis Example 124] Synthesis of Mat 124

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 741.26

[Synthesis Example 125] Synthesis of Mat 125

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 126] Synthesis of Mat 126

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 9] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 921.28

[Synthesis Example 127] Synthesis of Mat 127

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 714.25

[Synthesis Example 128] Synthesis of Mat 128

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 34] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 129] Synthesis of Mat 129

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 34] was used as a reactant; HRMS [M]+: 714.25

[Synthesis Example 130] Synthesis of Mat 130

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 35] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 131] Synthesis of Mat 131

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 35] was used as a reactant; HRMS [M]+: 714.25

[Synthesis Example 132] Synthesis of Mat 132

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 36] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 133] Synthesis of Mat 133

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 36] was used as a reactant; HRMS [M]+: 714.25

[Synthesis Example 134] Synthesis of Mat 134

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 37] was used as a reactant; HRMS [M]+: 806.28

[Synthesis Example 135] Synthesis of Mat 135

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 37] was used as a reactant; HRMS [M]+: 717.26

[Synthesis Example 136] Synthesis of Mat 136

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 37] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 137] Synthesis of Mat 137

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 37] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 138] Synthesis of Mat 138

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 37] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 139] Synthesis of Mat 139

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 73] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 140] Synthesis of Mat 140

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 74] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 141] Synthesis of Mat 141

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 38] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 142] Synthesis of Mat 142

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 38] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 143] Synthesis of Mat 143

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 75] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 144] Synthesis of Mat 144

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 76] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 145] Synthesis of Mat 145

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 39] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 146] Synthesis of Mat 146

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 39] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 147] Synthesis of Mat 147

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 77] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 148] Synthesis of Mat 148

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 78] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 149] Synthesis of Mat 149

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 40] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 150] Synthesis of Mat 150

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 40] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 151] Synthesis of Mat 151

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 79] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 152] Synthesis of Mat 152

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 80] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 153] Synthesis of Mat 153

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 41] was used as a reactant; HRMS [M]+: 882.31

[Synthesis Example 154] Synthesis of Mat 154

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 41] was used as a reactant; HRMS [M]+: 793.29

[Synthesis Example 155] Synthesis of Mat 155

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 41] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 156] Synthesis of Mat 156

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 41] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 157] Synthesis of Mat 157

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 42] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 158] Synthesis of Mat 158

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 42] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 159] Synthesis of Mat 159

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 43] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 160] Synthesis of Mat 160

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 43] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 161] Synthesis of Mat 161

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 44] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 162] Synthesis of Mat 162

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 44] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 163] Synthesis of Mat 163

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 45] was used as a reactant; HRMS [M]+: 882.31

[Synthesis Example 164] Synthesis of Mat 164

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 45] was used as a reactant; HRMS [M]+: 793.29

[Synthesis Example 165] Synthesis of Mat 165

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 45] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 166] Synthesis of Mat 166

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 45] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 167] Synthesis of Mat 167

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 46] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 168] Synthesis of Mat 168

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 46] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 169] Synthesis of Mat 169

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 47] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 170] Synthesis of Mat 170

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 47] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 171] Synthesis of Mat 171

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 48] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 172] Synthesis of Mat 172

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 48] was used as a reactant; HRMS [M]+: 766.28

[Synthesis Example 173] Synthesis of Mat 173

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 49] was used as a reactant; HRMS [M]+: 972.32

[Synthesis Example 174] Synthesis of Mat 174

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 49] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 175] Synthesis of Mat 175

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 49] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 176] Synthesis of Mat 176

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 49] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 177] Synthesis of Mat 177

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 50] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 178] Synthesis of Mat 178

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 50] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 179] Synthesis of Mat 179

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 51] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 180] Synthesis of Mat 180

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 51] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 181] Synthesis of Mat 181

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 52] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 182] Synthesis of Mat 182

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 52] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 183] Synthesis of Mat 183

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 53] was used as a reactant; HRMS [M]+: 971.33

[Synthesis Example 184] Synthesis of Mat 184

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 53] was used as a reactant; HRMS [M]+: 882.32

[Synthesis Example 185] Synthesis of Mat 185

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 53] was used as a reactant; HRMS [M]+: 972.23

[Synthesis Example 186] Synthesis of Mat 186

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 53] was used as a reactant; HRMS [M]+: 855.31

[Synthesis Example 187] Synthesis of Mat 187

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 54] was used as a reactant; HRMS [M]+: 972.23

[Synthesis Example 188] Synthesis of Mat 188

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 54] was used as a reactant; HRMS [M]+: 855.31

[Synthesis Example 189] Synthesis of Mat 189

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 55] was used as a reactant; HRMS [M]+: 972.23

[Synthesis Example 190] Synthesis of Mat 190

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 55] was used as a reactant; HRMS [M]+: 855.31

[Synthesis Example 191] Synthesis of Mat 191

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 56] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 192] Synthesis of Mat 192

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 56] was used as a reactant; HRMS [M]+: 855.31

[Synthesis Example 193] Synthesis of Mat 193

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 57] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 194] Synthesis of Mat 194

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 57] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 195] Synthesis of Mat 195

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 57] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 196] Synthesis of Mat 196

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 57] was used as a reactant; HRMS [M]+: 946.31

[Synthesis Example 197] Synthesis of Mat 197

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 57] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 198] Synthesis of Mat 198

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 81] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 199] Synthesis of Mat 199

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 82] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 200] Synthesis of Mat 200

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 58] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 201] Synthesis of Mat 201

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 58] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 202] Synthesis of Mat 202

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 83] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 203] Synthesis of Mat 203

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 84] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 204] Synthesis of Mat 204

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 59] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 205] Synthesis of Mat 205

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 59] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 206] Synthesis of Mat 206

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 85] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 207] Synthesis of Mat 207

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 86] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 208] Synthesis of Mat 208

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 60] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 209] Synthesis of Mat 209

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 60] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 210] Synthesis of Mat 210

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 87] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 211] Synthesis of Mat 211

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 88] was used as a reactant; HRMS [M]+: 831.27

[Synthesis Example 212] Synthesis of Mat 212

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 61] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 213] Synthesis of Mat 213

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 61] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 214] Synthesis of Mat 214

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 61] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 215] Synthesis of Mat 215

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 61] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 216] Synthesis of Mat 216

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 62] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 217] Synthesis of Mat 217

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 62] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 218] Synthesis of Mat 218

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 63] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 219] Synthesis of Mat 219

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 63] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 220] Synthesis of Mat 220

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 64] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 221] Synthesis of Mat 221

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 64] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 222] Synthesis of Mat 222

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 65] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 223] Synthesis of Mat 223

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 65] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 224] Synthesis of Mat 224

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 65] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 225] Synthesis of Mat 225

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 65] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 226] Synthesis of Mat 226

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 66] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 227] Synthesis of Mat 227

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 66] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 228] Synthesis of Mat 228

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 67] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 229] Synthesis of Mat 229

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 67] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 230] Synthesis of Mat 230

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 68] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 231] Synthesis of Mat 231

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 68] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 232] Synthesis of Mat 232

14.7 g of the target compound was obtained through the same process as [Synthesis Example 4], except that [Preparation Example 69] was used as a reactant; HRMS [M]+: 906.31

[Synthesis Example 233] Synthesis of Mat 233

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 69] was used as a reactant; HRMS [M]+: 817.29

[Synthesis Example 234] Synthesis of Mat 234

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 69] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 235] Synthesis of Mat 235

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 69] was used as a reactant; HRMS [M]+: 790.28

[Synthesis Example 236] Synthesis of Mat 236

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 70] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 237] Synthesis of Mat 237

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 70] was used as a reactant; HRMS [M]+: 790.28

[Synthesis Example 238] Synthesis of Mat 238

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 71] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 239] Synthesis of Mat 239

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 71] was used as a reactant; HRMS [M]+: 790.28

[Synthesis Example 240] Synthesis of Mat 240

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 72] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 241] Synthesis of Mat 241

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 72] was used as a reactant; HRMS [M]+: 790.28

[Synthesis Example 242] Synthesis of Mat 242

Under a nitrogen stream, [Preparation Example 1] 6.13 g (14.99 mmol) and 4-(3-bromophenyl)-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine 8.58 g ( 250 mL of xylene was added to the solution (17.99 mmol). 30.68 g (0.75 mmol) of Pd2(dba), 30.3 g (1.499 mmol) of P(t-Bu), and 3.59 g (37.47 mol) of NaOtBu were added and heated and refluxed at 120°C for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated by adding 500 mL of ammonium chloride aqueous solution to the reaction solution. The mixed solution was extracted with 500 mL of M.C. and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain 10.2 g of the target compound (yield 85%). 1H-NMR: 8.55(d, 1H), 8.35~8.21(m 5H), 8.06~7.94(m, 8H), 7.68~7.31(m, 20H), 7.16(t, 1H); HRMS [M]+:806.28

[Synthesis Example 243] Synthesis of Mat 243

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242], except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used as a reactant. .; HRMS [M]+: 717.26

[Synthesis Example 244] Synthesis of Mat 244

[Synthesis example] Except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used as a reactant. 242], the same process was performed to obtain 13.8 g of the target compound; HRMS [M]+: 807.27

[Synthesis Example 245] Synthesis of Mat 245

9-(4-(3-bromophenyl)-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazin-2-yl)-9H-carbazole as reactant The same process as [Synthesis Example 242] was performed except that 13.1 g of the target compound was obtained; HRMS [M]+: 896.30

[Synthesis Example 246] Synthesis of Mat 246

[Synthesis example] Except that 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used as a reactant. 242], the same process was performed to obtain 14.5 g of the target compound; HRMS [M]+: 807.27

[Synthesis Example 247] Synthesis of Mat 247

Reactant 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3 , 15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that 5-triazine was used; HRMS [M]+: 883.30

[Synthesis Example 248] Synthesis of Mat 248

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 249] Synthesis of Mat 249

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 250] Synthesis of Mat 250

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 2] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 251] Synthesis of Mat 251

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 252] Synthesis of Mat 252

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 253] Synthesis of Mat 253

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 254] Synthesis of Mat 254

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 255] Synthesis of Mat 255

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 256] Synthesis of Mat 256

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 257] Synthesis of Mat 257

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 882.31

[Synthesis Example 258] Synthesis of Mat 258

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 793.29

[Synthesis Example 259] Synthesis of Mat 259

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 260] Synthesis of Mat 260

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 261] Synthesis of Mat 261

14.1 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 262] Synthesis of Mat 262

14.6 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 263] Synthesis of Mat 263

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 264] Synthesis of Mat 264

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 882.31

[Synthesis Example 265] Synthesis of Mat 265

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 793.29

[Synthesis Example 266] Synthesis of Mat 266

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 267] Synthesis of Mat 267

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 268] Synthesis of Mat 268

13.7 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 269] Synthesis of Mat 269

15.1 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 11] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 270] Synthesis of Mat 270

12.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 271] Synthesis of Mat 271

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 972.32

[Synthesis Example 272] Synthesis of Mat 272

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 273] Synthesis of Mat 273

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 274] Synthesis of Mat 274

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 275] Synthesis of Mat 275

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 276] Synthesis of Mat 276

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 277] Synthesis of Mat 277

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 278] Synthesis of Mat 278

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 971.33

[Synthesis Example 279] Synthesis of Mat 279

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 882.32

[Synthesis Example 280] Synthesis of Mat 280

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 281] Synthesis of Mat 281

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 282] Synthesis of Mat 282

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 283] Synthesis of Mat 283

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 284] Synthesis of Mat 284

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 285] Synthesis of Mat 285

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 286] Synthesis of Mat 286

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 287] Synthesis of Mat 287

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 288] Synthesis of Mat 288

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 946.31

[Synthesis Example 289] Synthesis of Mat 289

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 290] Synthesis of Mat 290

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 933.32

[Synthesis Example 291] Synthesis of Mat 291

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 946.31

[Synthesis Example 292] Synthesis of Mat 292

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 293] Synthesis of Mat 293

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 933.32

[Synthesis Example 294] Synthesis of Mat 294

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 946.31

[Synthesis Example 295] Synthesis of Mat 295

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 296] Synthesis of Mat 296

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 933.32

[Synthesis Example 297] Synthesis of Mat 297

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 946.31

[Synthesis Example 298] Synthesis of Mat 298

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 299] Synthesis of Mat 299

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 933.32

[Synthesis Example 300] Synthesis of Mat 300

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 301] Synthesis of Mat 301

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 302] Synthesis of Mat 302

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 303] Synthesis of Mat 303

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 304] Synthesis of Mat 304

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 26] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 305] Synthesis of Mat 305

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 27] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 306] Synthesis of Mat 306

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 28] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 307] Synthesis of Mat 307

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 856.29

[Synthesis Example 308] Synthesis of Mat 308

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 767.28

[Synthesis Example 309] Synthesis of Mat 309

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 310] Synthesis of Mat 310

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 29] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 311] Synthesis of Mat 311

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 30] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 312] Synthesis of Mat 312

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 31] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 313] Synthesis of Mat 313

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 32] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 314] Synthesis of Mat 314

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 906.31

[Synthesis Example 315] Synthesis of Mat 315

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 817.29

[Synthesis Example 316] Synthesis of Mat 316

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 317] Synthesis of Mat 317

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 318] Synthesis of Mat 318

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 34] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 319] Synthesis of Mat 319

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 35] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 320] Synthesis of Mat 320

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 36] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 321] Synthesis of Mat 321

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 89] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 322] Synthesis of Mat 322

15.9 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 90] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 323] Synthesis of Mat 323

15.0 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 91] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 324] Synthesis of Mat 324

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 92] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 325] Synthesis of Mat 325

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 89] was used as a reactant; HRMS [M]+: 807.27

[Synthesis Example 326] Synthesis of Mat 326

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 93] was used as a reactant; HRMS [M]+: 883.30

[Synthesis Example 327] Synthesis of Mat 327

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 94] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 328] Synthesis of Mat 328

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 95] was used as a reactant; HRMS [M]+: 973.31

[Synthesis Example 329] Synthesis of Mat 329

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 96] was used as a reactant; HRMS [M]+: 972.33

[Synthesis Example 330] Synthesis of Mat 330

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 97] was used as a reactant; HRMS [M]+: 857.29

[Synthesis Example 331] Synthesis of Mat 331

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 97] was used as a reactant; HRMS [M]+: 740.27

[Synthesis Example 332] Synthesis of Mat 332

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 98] was used as a reactant; HRMS [M]+: 907.30

[Synthesis Example 333] Synthesis of Mat 333

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 89] was used as a reactant; HRMS [M]+: 983.30

[Synthesis Example 334] Synthesis of Mat 334

14.9 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 90] was used as a reactant; HRMS [M]+: 983.30

[Synthesis Example 335] Synthesis of Mat 335

Except that 2-(3-bromophenyl)-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine was used as a reactant [Synthesis Example 331 ], the same process was performed to obtain 15.9 g of the target compound; HRMS [M]+: 973.31

[Synthesis Example 336] Synthesis of Mat 336

As a reactant, 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3, 16.2 g of the target compound was obtained by performing the same process as [Synthesis Example 331] except that 5-triazine was used; HRMS [M]+: 959.33

[Synthesis Example 337] Synthesis of Mat 337

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 746.22

[Synthesis Example 338] Synthesis of Mat 338

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 5] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 657.21

[Synthesis Example 339] Synthesis of Mat 339

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 733.24

[Synthesis Example 340] Synthesis of Mat 340

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 8] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 341] Synthesis of Mat 341

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 836.24

[Synthesis Example 342] Synthesis of Mat 342

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 11] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 630.20

[Synthesis Example 343] Synthesis of Mat 343

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 16] except that [Preparation Example 100] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 344] Synthesis of Mat 344

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 18] except that [Preparation Example 100] was used as a reactant; HRMS [M]+: 630.20

[Synthesis Example 345] Synthesis of Mat 345

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 21] except that [Preparation Example 101] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 346] Synthesis of Mat 346

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 23] except that [Preparation Example 101] was used as a reactant; HRMS [M]+: 630.20

[Synthesis Example 347] Synthesis of Mat 347

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 26] except that [Preparation Example 102] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 348] Synthesis of Mat 348

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 28] except that [Preparation Example 102] was used as a reactant; HRMS [M]+: 630.20

[Synthesis Example 349] Synthesis of Mat 349

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 31] except that [Preparation Example 103] was used as a reactant; HRMS [M]+: 825.25

[Synthesis Example 350] Synthesis of Mat 350

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 33] except that [Preparation Example 103] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 351] Synthesis of Mat 351

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 34] except that [Preparation Example 104] was used as a reactant; HRMS [M]+: 825.25

[Synthesis Example 352] Synthesis of Mat 352

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 35] except that [Preparation Example 104] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 353] Synthesis of Mat 353

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 36] except that [Preparation Example 105] was used as a reactant; HRMS [M]+: 825.25

[Synthesis Example 354] Synthesis of Mat 354

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 37] except that [Preparation Example 105] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 355] Synthesis of Mat 355

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 38] except that [Preparation Example 106] was used as a reactant; HRMS [M]+: 825.25

[Synthesis Example 356] Synthesis of Mat 356

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 39] except that [Preparation Example 106] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 357] Synthesis of Mat 357

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 42] except that [Preparation Example 107] was used as a reactant; HRMS [M]+: 825.25

[Synthesis Example 358] Synthesis of Mat 358

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 44] except that [Preparation Example 107] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 359] Synthesis of Mat 359

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 45] except that [Preparation Example 108] was used as a reactant; HRMS [M]+: 825.25

[Synthesis Example 360] Synthesis of Mat 360

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 46] except that [Preparation Example 108] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 361] Synthesis of Mat 361

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 47] except that [Preparation Example 109] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 362] Synthesis of Mat 362

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 48] except that [Preparation Example 109] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 363] Synthesis of Mat 363

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 49] except that [Preparation Example 110] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 364] Synthesis of Mat 364

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 50] except that [Preparation Example 110] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 365] Synthesis of Mat 365

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 53] except that [Preparation Example 111] was used as a reactant; HRMS [M]+: 913.26

[Synthesis Example 366] Synthesis of Mat 366

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 55] except that [Preparation Example 111] was used as a reactant; HRMS [M]+: 796.24

[Synthesis Example 367] Synthesis of Mat 367

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 56], except that [Preparation Example 112] was used as a reactant; HRMS [M]+: 913.26

[Synthesis Example 368] Synthesis of Mat 368

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 57] except that [Preparation Example 112] was used as a reactant; HRMS [M]+: 796.24

[Synthesis Example 369] Synthesis of Mat 369

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 58] except that [Preparation Example 113] was used as a reactant; HRMS [M]+: 913.26

[Synthesis Example 370] Synthesis of Mat 370

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 59] except that [Preparation Example 113] was used as a reactant; HRMS [M]+: 796.24

[Synthesis Example 371] Synthesis of Mat 371

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 60] except that [Preparation Example 114] was used as a reactant; HRMS [M]+: 913.26

[Synthesis Example 372] Synthesis of Mat 372

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 61] except that [Preparation Example 114] was used as a reactant; HRMS [M]+: 796.24

[Synthesis Example 373] Synthesis of Mat 373

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 64] except that [Preparation Example 115] was used as a reactant; HRMS [M]+: 912.28

[Synthesis Example 374] Synthesis of Mat 374

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 66] except that [Preparation Example 115] was used as a reactant; HRMS [M]+: 795.25

[Synthesis Example 375] Synthesis of Mat 375

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 67] except that [Preparation Example 116] was used as a reactant; HRMS [M]+: 912.28

[Synthesis Example 376] Synthesis of Mat 376

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 68] except that [Preparation Example 116] was used as a reactant; HRMS [M]+: 795.25

[Synthesis Example 377] Synthesis of Mat 377

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 69] except that [Preparation Example 117] was used as a reactant; HRMS [M]+: 912.28

[Synthesis Example 378] Synthesis of Mat 378

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 70] except that [Preparation Example 117] was used as a reactant; HRMS [M]+: 795.25

[Synthesis Example 379] Synthesis of Mat 379

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 71] except that [Preparation Example 118] was used as a reactant; HRMS [M]+: 912.28

[Synthesis Example 380] Synthesis of Mat 380

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 72] except that [Preparation Example 118] was used as a reactant; HRMS [M]+: 795.25

[Synthesis Example 381] Synthesis of Mat 381

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 76] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 796.24

[Synthesis Example 382] Synthesis of Mat 382

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 77] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 707.22

[Synthesis Example 383] Synthesis of Mat 383

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 78] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 783.25

[Synthesis Example 384] Synthesis of Mat 384

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 80] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 385] Synthesis of Mat 385

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 82], except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 886.26

[Synthesis Example 386] Synthesis of Mat 386

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 83] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 387] Synthesis of Mat 387

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 88] except that [Preparation Example 120] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 388] Synthesis of Mat 388

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 90] except that [Preparation Example 120] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 389] Synthesis of Mat 389

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 93] except that [Preparation Example 121] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 390] Synthesis of Mat 390

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 95], except that [Preparation Example 121] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 391] Synthesis of Mat 391

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 98] except that [Preparation Example 122] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 392] Synthesis of Mat 392

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 100] except that [Preparation Example 122] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 393] Synthesis of Mat 393

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 103] except that [Preparation Example 123] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 394] Synthesis of Mat 394

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 105] except that [Preparation Example 123] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 395] Synthesis of Mat 395

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 106] except that [Preparation Example 124] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 396] Synthesis of Mat 396

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 107] except that [Preparation Example 124] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 397] Synthesis of Mat 397

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 108] except that [Preparation Example 125] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 398] Synthesis of Mat 398

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 109] except that [Preparation Example 125] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 399] Synthesis of Mat 399

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 110] except that [Preparation Example 126] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 400] Synthesis of Mat 400

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 111] except that [Preparation Example 126] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 401] Synthesis of Mat 401

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 114] except that [Preparation Example 127] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 402] Synthesis of Mat 402

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 116] except that [Preparation Example 127] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 403] Synthesis of Mat 403

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 117] except that [Preparation Example 128] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 404] Synthesis of Mat 404

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 118] except that [Preparation Example 128] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 405] Synthesis of Mat 405

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 119] except that [Preparation Example 129] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 406] Synthesis of Mat 406

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 120] except that [Preparation Example 129] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 407] Synthesis of Mat 407

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 121] except that [Preparation Example 130] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 408] Synthesis of Mat 408

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 122] except that [Preparation Example 130] was used as a reactant; HRMS [M]+: 680.21

[Synthesis Example 409] Synthesis of Mat 409

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 125] except that [Preparation Example 131] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 410] Synthesis of Mat 410

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 127] except that [Preparation Example 131] was used as a reactant; HRMS [M]+: 730.25

[Synthesis Example 411] Synthesis of Mat 411

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 128] except that [Preparation Example 132] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 412] Synthesis of Mat 412

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 129] except that [Preparation Example 132] was used as a reactant; HRMS [M]+: 730.23

[Synthesis Example 413] Synthesis of Mat 413

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 130] except that [Preparation Example 133] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 414] Synthesis of Mat 414

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 131] except that [Preparation Example 133] was used as a reactant; HRMS [M]+: 730.23

[Synthesis Example 415] Synthesis of Mat 415

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 132] except that [Preparation Example 134] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 416] Synthesis of Mat 416

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 133] except that [Preparation Example 134] was used as a reactant; HRMS [M]+: 730.23

[Synthesis Example 417] Synthesis of Mat 417

14.7 g of the target compound was obtained through the same process as [Synthesis Example 134], except that [Preparation Example 135] was used as a reactant; HRMS [M]+: 822.25

[Synthesis Example 418] Synthesis of Mat 418

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 135] except that [Preparation Example 135] was used as a reactant; HRMS [M]+: 733.24

[Synthesis Example 419] Synthesis of Mat 419

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 136] except that [Preparation Example 135] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 420] Synthesis of Mat 420

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 137] except that [Preparation Example 135] was used as a reactant; HRMS [M]+: 912.28

[Synthesis Example 421] Synthesis of Mat 421

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 138] except that [Preparation Example 135] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 422] Synthesis of Mat 422

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 139] except that [Preparation Example 171] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 423] Synthesis of Mat 423

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 140] except that [Preparation Example 172] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 424] Synthesis of Mat 424

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 141] except that [Preparation Example 136] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 425] Synthesis of Mat 425

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 142] except that [Preparation Example 136] was used as a reactant; HRMS [M]+: 690.25

[Synthesis Example 426] Synthesis of Mat 426

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 143] except that [Preparation Example 173] was used as a reactant; HRMS [M]+: 731.24

[Synthesis Example 427] Synthesis of Mat 427

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 144] except that [Preparation Example 174] was used as a reactant; HRMS [M]+: 781.26

[Synthesis Example 428] Synthesis of Mat 428

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 145] except that [Preparation Example 137] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 429] Synthesis of Mat 429

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 146] except that [Preparation Example 137] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 430] Synthesis of Mat 430

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 147] except that [Preparation Example 175] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 431] Synthesis of Mat 431

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 148] except that [Preparation Example 176] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 432] Synthesis of Mat 432

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 149] except that [Preparation Example 138] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 433] Synthesis of Mat 433

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 150] except that [Preparation Example 138] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 434] Synthesis of Mat 434

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 151] except that [Preparation Example 177] was used as a reactant; HRMS [M]+: 747.22

[Synthesis Example 435] Synthesis of Mat 435

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 152] except that [Preparation Example 178] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 436] Synthesis of Mat 436

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 155] except that [Preparation Example 139] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 437] Synthesis of Mat 437

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 156] except that [Preparation Example 139] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 438] Synthesis of Mat 438

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 157] except that [Preparation Example 140] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 439] Synthesis of Mat 439

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 158] except that [Preparation Example 140] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 440] Synthesis of Mat 440

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 159] except that [Preparation Example 141] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 441] Synthesis of Mat 441

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 160] except that [Preparation Example 141] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 442] Synthesis of Mat 442

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 161] except that [Preparation Example 142] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 443] Synthesis of Mat 443

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 162] except that [Preparation Example 142] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 444] Synthesis of Mat 444

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 165] except that [Preparation Example 143] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 445] Synthesis of Mat 445

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 166] except that [Preparation Example 143] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 446] Synthesis of Mat 446

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 167] except that [Preparation Example 144] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 447] Synthesis of Mat 447

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 168] except that [Preparation Example 144] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 448] Synthesis of Mat 448

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 169] except that [Preparation Example 145] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 449] Synthesis of Mat 449

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 170] except that [Preparation Example 145] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 450] Synthesis of Mat 450

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 171] except that [Preparation Example 146] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 451] Synthesis of Mat 451

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 172] except that [Preparation Example 146] was used as a reactant; HRMS [M]+: 782.26

[Synthesis Example 452] Synthesis of Mat 452

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 175] except that [Preparation Example 147] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 453] Synthesis of Mat 453

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 176] except that [Preparation Example 147] was used as a reactant; HRMS [M]+: 872.27

[Synthesis Example 454] Synthesis of Mat 454

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 177] except that [Preparation Example 148] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 455] Synthesis of Mat 455

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 178] except that [Preparation Example 148] was used as a reactant; HRMS [M]+: 872.27

[Synthesis Example 456] Synthesis of Mat 456

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 179] except that [Preparation Example 149] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 457] Synthesis of Mat 457

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 180] except that [Preparation Example 149] was used as a reactant; HRMS [M]+: 872.27

[Synthesis Example 458] Synthesis of Mat 458

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 181] except that [Preparation Example 150] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 459] Synthesis of Mat 459

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 182] except that [Preparation Example 150] was used as a reactant; HRMS [M]+: 872.27

[Synthesis Example 460] Synthesis of Mat 460

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 185] except that [Preparation Example 151] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 461] Synthesis of Mat 461

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 186] except that [Preparation Example 151] was used as a reactant; HRMS [M]+: 871.29

[Synthesis Example 462] Synthesis of Mat 462

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 187] except that [Preparation Example 152] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 463] Synthesis of Mat 463

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 188] except that [Preparation Example 152] was used as a reactant; HRMS [M]+: 871.29

[Synthesis Example 464] Synthesis of Mat 464

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 189] except that [Preparation Example 153] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 465] Synthesis of Mat 465

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 190] except that [Preparation Example 153] was used as a reactant; HRMS [M]+: 871.29

[Synthesis Example 466] Synthesis of Mat 466

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 191] except that [Preparation Example 154] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 467] Synthesis of Mat 467

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 192] except that [Preparation Example 154] was used as a reactant; HRMS [M]+: 871.29

[Synthesis Example 468] Synthesis of Mat 468

14.7 g of the target compound was obtained through the same process as [Synthesis Example 193], except that [Preparation Example 155] was used as a reactant; HRMS [M]+: 872.27

[Synthesis Example 469] Synthesis of Mat 469

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 194] except that [Preparation Example 155] was used as a reactant; HRMS [M]+: 783.25

[Synthesis Example 470] Synthesis of Mat 470

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 195] except that [Preparation Example 155] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 471] Synthesis of Mat 471

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 196] except that [Preparation Example 155] was used as a reactant; HRMS [M]+: 962.29

[Synthesis Example 472] Synthesis of Mat 472

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 197] except that [Preparation Example 155] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 473] Synthesis of Mat 473

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 198] except that [Preparation Example 179] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 474] Synthesis of Mat 474

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 199] except that [Preparation Example 180] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 475] Synthesis of Mat 475

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 200] except that [Preparation Example 156] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 476] Synthesis of Mat 476

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 201] except that [Preparation Example 156] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 477] Synthesis of Mat 477

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 202] except that [Preparation Example 181] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 478] Synthesis of Mat 478

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 203] except that [Preparation Example 182] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 479] Synthesis of Mat 479

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 204] except that [Preparation Example 157] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 480] Synthesis of Mat 480

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 205] except that [Preparation Example 157] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 481] Synthesis of Mat 481

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 206] except that [Preparation Example 183] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 482] Synthesis of Mat 482

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 207] except that [Preparation Example 184] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 483] Synthesis of Mat 483

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 208] except that [Preparation Example 158] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 484] Synthesis of Mat 484

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 209] except that [Preparation Example 158] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 485] Synthesis of Mat 485

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 210] except that [Preparation Example 185] was used as a reactant; HRMS [M]+: 797.23

[Synthesis Example 486] Synthesis of Mat 486

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 211] except that [Preparation Example 186] was used as a reactant; HRMS [M]+: 847.25

[Synthesis Example 487] Synthesis of Mat 487

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 214] except that [Preparation Example 159] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 488] Synthesis of Mat 488

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 215] except that [Preparation Example 159] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 489] Synthesis of Mat 489

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 216] except that [Preparation Example 160] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 490] Synthesis of Mat 490

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 217] except that [Preparation Example 160] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 491] Synthesis of Mat 491

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 218] except that [Preparation Example 161] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 492] Synthesis of Mat 492

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 219] except that [Preparation Example 161] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 493] Synthesis of Mat 493

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 220] except that [Preparation Example 162] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 494] Synthesis of Mat 494

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 221] except that [Preparation Example 162] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 495] Synthesis of Mat 495

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 224] except that [Preparation Example 163] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 496] Synthesis of Mat 496

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 225] except that [Preparation Example 163] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 497] Synthesis of Mat 497

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 226] except that [Preparation Example 164] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 498] Synthesis of Mat 498

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 227] except that [Preparation Example 164] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 499] Synthesis of Mat 499

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 228] except that [Preparation Example 165] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 500] Synthesis of Mat 500

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 229] except that [Preparation Example 165] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 501] Synthesis of Mat 501

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 230] except that [Preparation Example 166] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 502] Synthesis of Mat 502

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 231] except that [Preparation Example 166] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 503] Synthesis of Mat 503

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 234] except that [Preparation Example 167] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 504] Synthesis of Mat 504

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 235] except that [Preparation Example 167] was used as a reactant; HRMS [M]+: 806.26

[Synthesis Example 505] Synthesis of Mat 505

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 236] except that [Preparation Example 168] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 506] Synthesis of Mat 506

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 237] except that [Preparation Example 168] was used as a reactant; HRMS [M]+: 806.26

[Synthesis Example 507] Synthesis of Mat 507

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 238] except that [Preparation Example 169] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 508] Synthesis of Mat 508

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 239] except that [Preparation Example 169] was used as a reactant; HRMS [M]+: 806.26

[Synthesis Example 509] Synthesis of Mat 509

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 240] except that [Preparation Example 170] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 510] Synthesis of Mat 510

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 241] except that [Preparation Example 170] was used as a reactant; HRMS [M]+: 806.26

[Synthesis Example 511] Synthesis of Mat 511

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 822.25

[Synthesis Example 512] Synthesis of Mat 512

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 733.24

[Synthesis Example 513] Synthesis of Mat 513

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 514] Synthesis of Mat 514

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 912.28

[Synthesis Example 515] Synthesis of Mat 515

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 516] Synthesis of Mat 516

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 99] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 517] Synthesis of Mat 517

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 248] except that [Preparation Example 100] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 518] Synthesis of Mat 518

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 249] except that [Preparation Example 100] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 519] Synthesis of Mat 519

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 250] except that [Preparation Example 100] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 520] Synthesis of Mat 520

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 251] except that [Preparation Example 101] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 521] Synthesis of Mat 521

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 252] except that [Preparation Example 101] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 522] Synthesis of Mat 522

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 253] except that [Preparation Example 101] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 523] Synthesis of Mat 523

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 254] except that [Preparation Example 102] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 524] Synthesis of Mat 524

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 255] except that [Preparation Example 102] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 525] Synthesis of Mat 525

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 256] except that [Preparation Example 102] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 526] Synthesis of Mat 526

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 259] except that [Preparation Example 103] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 527] Synthesis of Mat 527

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 260] except that [Preparation Example 103] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 528] Synthesis of Mat 528

14.1 g of the target compound was obtained by performing the same process as [Synthesis Example 261] except that [Preparation Example 104] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 529] Synthesis of Mat 529

14.6 g of the target compound was obtained by performing the same process as [Synthesis Example 262] except that [Preparation Example 105] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 530] Synthesis of Mat 530

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 263] except that [Preparation Example 106] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 531] Synthesis of Mat 531

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 266] except that [Preparation Example 107] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 532] Synthesis of Mat 532

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 267] except that [Preparation Example 107] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 533] Synthesis of Mat 533

13.7 g of the target compound was obtained by performing the same process as [Synthesis Example 268] except that [Preparation Example 108] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 534] Synthesis of Mat 534

15.1 g of the target compound was obtained by performing the same process as [Synthesis Example 269] except that [Preparation Example 109] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 535] Synthesis of Mat 535

12.8 g of the target compound was obtained by performing the same process as [Synthesis Example 270] except that [Preparation Example 110] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 536] Synthesis of Mat 536

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 271] except that [Preparation Example 111] was used as a reactant; HRMS [M]+: 988.30

[Synthesis Example 537] Synthesis of Mat 537

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 273] except that [Preparation Example 111] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 538] Synthesis of Mat 538

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 274] except that [Preparation Example 111] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 539] Synthesis of Mat 539

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 275] except that [Preparation Example 112] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 540] Synthesis of Mat 540

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 276] except that [Preparation Example 113] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 541] Synthesis of Mat 541

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 277] except that [Preparation Example 114] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 542] Synthesis of Mat 542

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 278] except that [Preparation Example 115] was used as a reactant; HRMS [M]+: 987.31

[Synthesis Example 543] Synthesis of Mat 543

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 280] except that [Preparation Example 115] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 544] Synthesis of Mat 544

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 281] except that [Preparation Example 115] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 545] Synthesis of Mat 545

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 282] except that [Preparation Example 116] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 546] Synthesis of Mat 546

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 283] except that [Preparation Example 117] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 547] Synthesis of Mat 547

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 284] except that [Preparation Example 118] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 548] Synthesis of Mat 548

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 872.27

[Synthesis Example 549] Synthesis of Mat 549

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 783.25

[Synthesis Example 550] Synthesis of Mat 550

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 551] Synthesis of Mat 551

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 962.29

[Synthesis Example 552] Synthesis of Mat 552

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 553] Synthesis of Mat 553

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 119] was used as a reactant; HRMS [M]+: 949.39

[Synthesis Example 554] Synthesis of Mat 554

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 120] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 555] Synthesis of Mat 555

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 120] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 556] Synthesis of Mat 556

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 120] was used as a reactant; HRMS [M]+: 949.39

[Synthesis Example 557] Synthesis of Mat 557

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 121] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 558] Synthesis of Mat 558

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 121] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 559] Synthesis of Mat 559

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 121] was used as a reactant; HRMS [M]+: 949.39

[Synthesis Example 560] Synthesis of Mat 560

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 122] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 561] Synthesis of Mat 561

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 122] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 562] Synthesis of Mat 562

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 122] was used as a reactant; HRMS [M]+: 949.39

[Synthesis Example 563] Synthesis of Mat 563

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 123] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 564] Synthesis of Mat 564

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 123] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 565] Synthesis of Mat 565

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 124] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 567] Synthesis of Mat 567

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 125] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 568] Synthesis of Mat 568

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 126] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 569] Synthesis of Mat 569

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 127] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 570] Synthesis of Mat 570

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 127] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 571] Synthesis of Mat 571

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 128] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 572] Synthesis of Mat 572

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 129] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 573] Synthesis of Mat 573

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 130] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 574] Synthesis of Mat 574

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 131] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 575] Synthesis of Mat 575

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 131] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 576] Synthesis of Mat 576

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 132] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 577] Synthesis of Mat 577

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 133] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 578] Synthesis of Mat 578

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 134] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 579] Synthesis of Mat 579

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 321] except that [Preparation Example 187] was used as a reactant; HRMS [M]+: 823.25

[Synthesis Example 580] Synthesis of Mat 580

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 325] except that [Preparation Example 187] was used as a reactant; HRMS [M]+: 706.23

[Synthesis Example 581] Synthesis of Mat 581

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 326] except that [Preparation Example 191] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 582] Synthesis of Mat 582

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 327] except that [Preparation Example 192] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 583] Synthesis of Mat 583

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 328] except that [Preparation Example 193] was used as a reactant; HRMS [M]+: 989.29

[Synthesis Example 584] Synthesis of Mat 584

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 329] except that [Preparation Example 194] was used as a reactant; HRMS [M]+: 988.31

[Synthesis Example 585] Synthesis of Mat 585

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 330] except that [Preparation Example 195] was used as a reactant; HRMS [M]+: 873.26

[Synthesis Example 586] Synthesis of Mat 586

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 331] except that [Preparation Example 195] was used as a reactant; HRMS [M]+: 756.24

[Synthesis Example 587] Synthesis of Mat 587

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 332] except that [Preparation Example 196] was used as a reactant; HRMS [M]+: 923.28

[Synthesis Example 588] Synthesis of Mat 588

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 333] except that [Preparation Example 187] was used as a reactant; HRMS [M]+: 899.28

[Synthesis Example 589] Synthesis of Mat 589

16.2 g of the target compound was obtained by performing the same process as [Synthesis Example 336] except that [Preparation Example 187] was used as a reactant; HRMS [M]+: 975.31

[Synthesis Example 590] Synthesis of Mat 590

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 4] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 756.30

[Synthesis Example 591] Synthesis of Mat 591

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 6] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 743.31

[Synthesis Example 592] Synthesis of Mat 592

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 16] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 757.29

[Synthesis Example 593] Synthesis of Mat 593

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 10] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 846.32

[Synthesis Example 594] Synthesis of Mat 594

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 18] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 640.27

[Synthesis Example 595] Synthesis of Mat 595

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 21] except that [Preparation Example 198] was used as a reactant; HRMS [M]+: 757.29

[Synthesis Example 596] Synthesis of Mat 596

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 23] except that [Preparation Example 198] was used as a reactant; HRMS [M]+: 640.27

[Synthesis Example 597] Synthesis of Mat 597

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 26] except that [Preparation Example 199] was used as a reactant; HRMS [M]+: 757.29

[Synthesis Example 598] Synthesis of Mat 598

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 28] except that [Preparation Example 199] was used as a reactant; HRMS [M]+: 640.27

[Synthesis Example 599] Synthesis of Mat 599

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 34] except that [Preparation Example 200] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 600] Synthesis of Mat 600

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 35] except that [Preparation Example 200] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 601] Synthesis of Mat 601

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 36] except that [Preparation Example 201] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 602] Synthesis of Mat 602

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 37] except that [Preparation Example 201] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 603] Synthesis of Mat 603

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 38] except that [Preparation Example 202] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 604] Synthesis of Mat 604

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 39] except that [Preparation Example 202] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 605] Synthesis of Mat 605

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 45] except that [Preparation Example 203] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 606] Synthesis of Mat 606

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 46] except that [Preparation Example 203] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 607] Synthesis of Mat 607

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 47] except that [Preparation Example 204] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 608] Synthesis of Mat 608

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 48] except that [Preparation Example 204] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 609] Synthesis of Mat 609

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 49] except that [Preparation Example 205] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 610] Synthesis of Mat 610

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 50] except that [Preparation Example 205] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 611] Synthesis of Mat 611

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 56] except that [Preparation Example 206] was used as a reactant; HRMS [M]+: 923.33

[Synthesis Example 612] Synthesis of Mat 612

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 57] except that [Preparation Example 206] was used as a reactant; HRMS [M]+: 806.31

[Synthesis Example 613] Synthesis of Mat 613

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 58] except that [Preparation Example 207] was used as a reactant; HRMS [M]+: 923.33

[Synthesis Example 614] Synthesis of Mat 614

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 59] except that [Preparation Example 207] was used as a reactant; HRMS [M]+: 806.31

[Synthesis Example 615] Synthesis of Mat 615

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 60] except that [Preparation Example 208] was used as a reactant; HRMS [M]+: 923.33

[Synthesis Example 616] Synthesis of Mat 616

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 61] except that [Preparation Example 208] was used as a reactant; HRMS[M]+: 806.31

[Synthesis Example 617] Synthesis of Mat 617

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 67], except that [Preparation Example 209] was used as a reactant; HRMS [M]+: 922.35

[Synthesis Example 618] Synthesis of Mat 618

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 68] except that [Preparation Example 209] was used as a reactant; HRMS [M]+: 805.33

[Synthesis Example 619] Synthesis of Mat 619

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 69], except that [Preparation Example 210] was used as a reactant; HRMS [M]+: 925.35

[Synthesis Example 620] Synthesis of Mat 620

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 70] except that [Preparation Example 210] was used as a reactant; HRMS [M]+: 805.33

[Synthesis Example 621] Synthesis of Mat 621

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 71] except that [Preparation Example 211] was used as a reactant; HRMS [M]+: 925.35

[Synthesis Example 622] Synthesis of Mat 622

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 72] except that [Preparation Example 211] was used as a reactant; HRMS [M]+: 805.33

[Synthesis Example 623] Synthesis of Mat 623

14.7 g of the target compound was obtained by performing the same process as [Synthesis Example 76], except that [Preparation Example 212] was used as a reactant; HRMS[M]+: 806.31

[Synthesis Example 624] Synthesis of Mat 624

14.2 g of the target compound was obtained by performing the same process as [Synthesis Example 78] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 793.33

[Synthesis Example 625] Synthesis of Mat 625

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 88] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 626] Synthesis of Mat 626

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 82] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 896.33

[Synthesis Example 627] Synthesis of Mat 627

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 90] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 690.29

[Synthesis Example 628] Synthesis of Mat 628

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 93] except that [Preparation Example 213] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 629] Synthesis of Mat 629

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 95] except that [Preparation Example 213] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 630] Synthesis of Mat 630

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 98] except that [Preparation Example 214] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 631] Synthesis of Mat 631

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 100] except that [Preparation Example 214] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 632] Synthesis of Mat 632

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 106] except that [Preparation Example 215] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 633] Synthesis of Mat 633

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 107] except that [Preparation Example 215] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 634] Synthesis of Mat 634

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 108] except that [Preparation Example 216] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 635] Synthesis of Mat 635

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 109] except that [Preparation Example 216] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 636] Synthesis of Mat 636

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 110] except that [Preparation Example 217] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 637] Synthesis of Mat 637

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 111] except that [Preparation Example 217] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 638] Synthesis of Mat 638

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 117] except that [Preparation Example 218] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 639] Synthesis of Mat 639

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 118] except that [Preparation Example 218] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 640] Synthesis of Mat 640

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 119] except that [Preparation Example 219] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 641] Synthesis of Mat 641

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 120] except that [Preparation Example 219] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 642] Synthesis of Mat 642

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 121] except that [Preparation Example 220] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 643] Synthesis of Mat 643

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 122] except that [Preparation Example 220] was used as a reactant; HRMS [M]+: 690.20

[Synthesis Example 644] Synthesis of Mat 644

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 128] except that [Preparation Example 221] was used as a reactant; HRMS [M]+: 857.32

[Synthesis Example 645] Synthesis of Mat 645

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 129] except that [Preparation Example 221] was used as a reactant; HRMS [M]+: 740.30

[Synthesis Example 646] Synthesis of Mat 646

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 130] except that [Preparation Example 222] was used as a reactant; HRMS [M]+: 857.32

[Synthesis Example 647] Synthesis of Mat 647

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 131] except that [Preparation Example 222] was used as a reactant; HRMS [M]+: 740.30

[Synthesis Example 648] Synthesis of Mat 648

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 132] except that [Preparation Example 223] was used as a reactant; HRMS [M]+: 857.32

[Synthesis Example 649] Synthesis of Mat 649

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 133] except that [Preparation Example 223] was used as a reactant; HRMS [M]+: 740.30

[Synthesis Example 650] Synthesis of Mat 650

14.7 g of the target compound was obtained through the same process as [Synthesis Example 134], except that [Preparation Example 224] was used as a reactant; HRMS [M]+: 832.33

[Synthesis Example 651] Synthesis of Mat 651

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 136] except that [Preparation Example 224] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 652] Synthesis of Mat 652

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 137] except that [Preparation Example 224] was used as a reactant; HRMS [M]+: 922.35

[Synthesis Example 653] Synthesis of Mat 653

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 138] except that [Preparation Example 224] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 654] Synthesis of Mat 654

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 139] except that [Preparation Example 251] was used as a reactant; HRMS [M]+: 757.29

[Synthesis Example 655] Synthesis of Mat 655

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 140] except that [Preparation Example 252] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 656] Synthesis of Mat 656

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 145] except that [Preparation Example 225] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 657] Synthesis of Mat 657

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 146] except that [Preparation Example 225] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 658] Synthesis of Mat 658

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 147] except that [Preparation Example 253] was used as a reactant; HRMS [M]+: 757.29

[Synthesis Example 659] Synthesis of Mat 659

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 148] except that [Preparation Example 254] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 660] Synthesis of Mat 660

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 149] except that [Preparation Example 226] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 661] Synthesis of Mat 661

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 150] except that [Preparation Example 226] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 662] Synthesis of Mat 662

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 151] except that [Preparation Example 255] was used as a reactant; HRMS [M]+: 757.29

[Synthesis Example 663] Synthesis of Mat 663

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 152] except that [Preparation Example 256] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 664] Synthesis of Mat 664

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 157] except that [Preparation Example 227] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 665] Synthesis of Mat 665

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 158] except that [Preparation Example 227] was used as a reactant; HRMS [M]+: 792.33

[Synthesis Example 666] Synthesis of Mat 666

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 159] except that [Preparation Example 228] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 667] Synthesis of Mat 667

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 160] except that [Preparation Example 228] was used as a reactant; HRMS [M]+: 792.33

[Synthesis Example 668] Synthesis of Mat 668

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 161] except that [Preparation Example 229] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 669] Synthesis of Mat 669

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 162] except that [Preparation Example 229] was used as a reactant; HRMS [M]+: 792.33

[Synthesis Example 670] Synthesis of Mat 670

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 167] except that [Preparation Example 230] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 671] Synthesis of Mat 671

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 168] except that [Preparation Example 230] was used as a reactant; HRMS [M]+: 792.33

[Synthesis Example 672] Synthesis of Mat 672

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 169] except that [Preparation Example 231] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 673] Synthesis of Mat 673

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 170] except that [Preparation Example 231] was used as a reactant; HRMS [M]+: 792.33

[Synthesis Example 674] Synthesis of Mat 674

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 171] except that [Preparation Example 232] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 675] Synthesis of Mat 675

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 172] except that [Preparation Example 232] was used as a reactant; HRMS [M]+: 792.33

[Synthesis Example 676] Synthesis of Mat 676

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 177] except that [Preparation Example 233] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 677] Synthesis of Mat 677

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 178] except that [Preparation Example 233] was used as a reactant; HRMS [M]+: 882.34

[Synthesis Example 678] Synthesis of Mat 678

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 179] except that [Preparation Example 234] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 679] Synthesis of Mat 679

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 180] except that [Preparation Example 234] was used as a reactant; HRMS [M]+: 882.34

[Synthesis Example 680] Synthesis of Mat 680

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 181] except that [Preparation Example 235] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 681] Synthesis of Mat 681

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 182] except that [Preparation Example 235] was used as a reactant; HRMS [M]+: 882.34

[Synthesis Example 682] Synthesis of Mat 682

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 187] except that [Preparation Example 236] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 683] Synthesis of Mat 683

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 188] except that [Preparation Example 236] was used as a reactant; HRMS [M]+: 881.36

[Synthesis Example 684] Synthesis of Mat 684

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 189] except that [Preparation Example 237] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 685] Synthesis of Mat 685

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 190] except that [Preparation Example 237] was used as a reactant; HRMS [M]+: 881.36

[Synthesis Example 686] Synthesis of Mat 686

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 191] except that [Preparation Example 238] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 687] Synthesis of Mat 687

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 192] except that [Preparation Example 238] was used as a reactant; HRMS [M]+: 881.36

[Synthesis Example 688] Synthesis of Mat 688

14.7 g of the target compound was obtained through the same process as [Synthesis Example 193], except that [Preparation Example 239] was used as a reactant; HRMS [M]+: 882.34

[Synthesis Example 689] Synthesis of Mat 689

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 195] except that [Preparation Example 239] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 690] Synthesis of Mat 690

15.3 g of the target compound was obtained by performing the same process as [Synthesis Example 196] except that [Preparation Example 239] was used as a reactant; HRMS [M]+: 972.37

[Synthesis Example 691] Synthesis of Mat 691

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 197] except that [Preparation Example 239] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 692] Synthesis of Mat 692

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 198] except that [Preparation Example 257] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 693] Synthesis of Mat 693

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 199] except that [Preparation Example 258] was used as a reactant; HRMS [M]+: 857.32

[Synthesis Example 694] Synthesis of Mat 694

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 204] except that [Preparation Example 240] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 695] Synthesis of Mat 695

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 205] except that [Preparation Example 240] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 696] Synthesis of Mat 696

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 206] except that [Preparation Example 259] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 697] Synthesis of Mat 697

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 207] except that [Preparation Example 260] was used as a reactant; HRMS [M]+: 857.32

[Synthesis Example 698] Synthesis of Mat 698

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 208] except that [Preparation Example 241] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 699] Synthesis of Mat 699

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 209] except that [Preparation Example 241] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 700] Synthesis of Mat 700

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 210] except that [Preparation Example 261] was used as a reactant; HRMS [M]+: 807.31

[Synthesis Example 701] Synthesis of Mat 701

15.4 g of the target compound was obtained by performing the same process as [Synthesis Example 211] except that [Preparation Example 262] was used as a reactant; HRMS [M]+: 857.32

[Synthesis Example 702] Synthesis of Mat 702

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 216] except that [Preparation Example 242] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 703] Synthesis of Mat 703

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 217] except that [Preparation Example 242] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 704] Synthesis of Mat 704

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 218] except that [Preparation Example 243] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 705] Synthesis of Mat 705

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 219] except that [Preparation Example 243] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 706] Synthesis of Mat 706

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 220] except that [Preparation Example 244] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 707] Synthesis of Mat 707

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 221] except that [Preparation Example 244] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 708] Synthesis of Mat 708

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 226] except that [Preparation Example 245] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 709] Synthesis of Mat 709

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 227] except that [Preparation Example 245] was used as a reactant; HRMS [M]+: 766,32

[Synthesis Example 710] Synthesis of Mat 710

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 228] except that [Preparation Example 246] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 711] Synthesis of Mat 711

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 229] except that [Preparation Example 246] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 712] Synthesis of Mat 712

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 230] except that [Preparation Example 247] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 713] Synthesis of Mat 713

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 231] except that [Preparation Example 247] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 714] Synthesis of Mat 714

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 236] except that [Preparation Example 248] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 715] Synthesis of Mat 715

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 237] except that [Preparation Example 248] was used as a reactant; HRMS [M]+: 816.33

[Synthesis Example 716] Synthesis of Mat 716

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 238] except that [Preparation Example 249] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 717] Synthesis of Mat 717

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 239] except that [Preparation Example 249] was used as a reactant; HRMS [M]+: 816.33

[Synthesis Example 718] Synthesis of Mat 718

14.8 g of the target compound was obtained by performing the same process as [Synthesis Example 240] except that [Preparation Example 250] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 719] Synthesis of Mat 719

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 241] except that [Preparation Example 250] was used as a reactant; HRMS [M]+: 816.33

[Synthesis Example 720] Synthesis of Mat 720

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 832.33

[Synthesis Example 721] Synthesis of Mat 721

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 243] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 743.31

[Synthesis Example 722] Synthesis of Mat 722

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 723] Synthesis of Mat 723

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 922.35

[Synthesis Example 724] Synthesis of Mat 724

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 833,32

[Synthesis Example 725] Synthesis of Mat 725

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 197] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 726] Synthesis of Mat 726

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 251] except that [Preparation Example 198] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 727] Synthesis of Mat 727

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 252] except that [Preparation Example 198] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 728] Synthesis of Mat 728

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 253] except that [Preparation Example 198] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 729] Synthesis of Mat 729

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 254] except that [Preparation Example 199] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 730] Synthesis of Mat 730

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 255] except that [Preparation Example 199] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 731] Synthesis of Mat 731

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 256] except that [Preparation Example 199] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 732] Synthesis of Mat 732

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 259] except that [Preparation Example 200] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 733] Synthesis of Mat 733

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 260] except that [Preparation Example 200] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 734] Synthesis of Mat 734

14.6 g of the target compound was obtained by performing the same process as [Synthesis Example 262] except that [Preparation Example 201] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 735] Synthesis of Mat 735

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 263] except that [Preparation Example 202] was used as a reactant; HRMS [M]+: 9093.5

[Synthesis Example 736] Synthesis of Mat 736

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 266] except that [Preparation Example 203] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 737] Synthesis of Mat 737

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 267] except that [Preparation Example 203] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 738] Synthesis of Mat 738

15.1 g of the target compound was obtained by performing the same process as [Synthesis Example 269] except that [Preparation Example 204] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 739] Synthesis of Mat 739

12.8 g of the target compound was obtained by performing the same process as [Synthesis Example 270] except that [Preparation Example 205] was used as a reactant; HRMS [M]+: 9093.5

[Synthesis Example 740] Synthesis of Mat 740

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 271] except that [Preparation Example 206] was used as a reactant; HRMS [M]+: 988.37

[Synthesis Example 741] Synthesis of Mat 741

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 273] except that [Preparation Example 206] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 742] Synthesis of Mat 742

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 274] except that [Preparation Example 206] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 743] Synthesis of Mat 743

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 276] except that [Preparation Example 207] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 744] Synthesis of Mat 744

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 277] except that [Preparation Example 208] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 745] Synthesis of Mat 745

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 209] was used as a reactant; HRMS [M]+: 997.39

[Synthesis Example 746] Synthesis of Mat 746

12.9 g of the target compound was obtained by performing the same process as [Synthesis Example 280] except that [Preparation Example 209] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 747] Synthesis of Mat 747

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 281] except that [Preparation Example 209] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 748] Synthesis of Mat 748

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 283] except that [Preparation Example 210] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 749] Synthesis of Mat 749

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 284] except that [Preparation Example 211] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 750] Synthesis of Mat 750

12.7 g of the target compound was obtained by performing the same process as [Synthesis Example 242] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 882.34

[Synthesis Example 751] Synthesis of Mat 751

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 752] Synthesis of Mat 752

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 972.37

[Synthesis Example 753] Synthesis of Mat 753

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 754] Synthesis of Mat 754

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 212] was used as a reactant; HRMS [M]+: 959.37

[Synthesis Example 755] Synthesis of Mat 755

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 213] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 756] Synthesis of Mat 756

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 213] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 757] Synthesis of Mat 757

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 213] was used as a reactant; HRMS [M]+: 959.37

[Synthesis Example 758] Synthesis of Mat 758

13.1 g of the target compound was obtained by performing the same process as [Synthesis Example 245] except that [Preparation Example 214] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 759] Synthesis of Mat 759

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 214] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 760] Synthesis of Mat 760

15.2 g of the target compound was obtained by performing the same process as [Synthesis Example 247] except that [Preparation Example 214] was used as a reactant; HRMS [M]+: 959.37

[Synthesis Example 761] Synthesis of Mat 761

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 215] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 762] Synthesis of Mat 762

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 215] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 763] Synthesis of Mat 763

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 216] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 764] Synthesis of Mat 764

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 217] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 765] Synthesis of Mat 765

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 218] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 766] Synthesis of Mat 766

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 218] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 767] Synthesis of Mat 767

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 219] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 768] Synthesis of Mat 768

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 220] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 769] Synthesis of Mat 769

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 221] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 770] Synthesis of Mat 770

14.5 g of the target compound was obtained by performing the same process as [Synthesis Example 246] except that [Preparation Example 221] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 771] Synthesis of Mat 771

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 222] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 772] Synthesis of Mat 772

13.8 g of the target compound was obtained by performing the same process as [Synthesis Example 244] except that [Preparation Example 223] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 773] Synthesis of Mat 773

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 321] except that [Preparation Example 263] was used as a reactant; HRMS [M]+: 833.32

[Synthesis Example 774] Synthesis of Mat 774

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 325] except that [Preparation Example 263] was used as a reactant; HRMS [M]+: 716.30

[Synthesis Example 775] Synthesis of Mat 775

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 326] except that [Preparation Example 266] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 776] Synthesis of Mat 776

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 327] except that [Preparation Example 267] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 777] Synthesis of Mat 777

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 328] except that [Preparation Example 268] was used as a reactant; HRMS [M]+: 999.37

[Synthesis Example 778] Synthesis of Mat 778

15.6 g of the target compound was obtained by performing the same process as [Synthesis Example 329] except that [Preparation Example 269] was used as a reactant; HRMS [M]+: 998.38

[Synthesis Example 779] Synthesis of Mat 779

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 330] except that [Preparation Example 1270] was used as a reactant; HRMS [M]+: 883.34

[Synthesis Example 780] Synthesis of Mat 780

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 331] except that [Preparation Example 270] was used as a reactant; HRMS [M]+: 766.32

[Synthesis Example 781] Synthesis of Mat 781

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 332] except that [Preparation Example 217] was used as a reactant; HRMS [M]+: 933.35

[Synthesis Example 782] Synthesis of Mat 782

14.3 g of the target compound was obtained by performing the same process as [Synthesis Example 333] except that [Preparation Example 263] was used as a reactant; HRMS [M]+: 909.35

[Synthesis Example 783] Synthesis of Mat 783

16.2 g of the target compound was obtained by performing the same process as [Synthesis Example 336] except that [Preparation Example 263] was used as a reactant; HRMS [M]+: 985.39

[ Example 1 to 47] Fabrication of green organic EL devices

Compounds Mat-1 to Mat-783 synthesized in Synthesis Examples 1 to 783 were purified to high purity by sublimation using a commonly known method, and then a green organic EL device was manufactured according to the process below.

First, a glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). Then, the substrate is cleaned using UV for 5 minutes and then vacuum evaporated. The substrate was transferred to .

On the ITO transparent electrode prepared in this way, each compound of m-MTDATA (60 nm)/TCTA (80 nm)/MAt-6 to Mat-783 + 10% Ir(ppy) ₃ (30nm)/BCP (10 nm)/Alq An organic EL device was manufactured by stacking ₃ (30 nm)/LiF (1 nm)/Al (200 nm) in the order.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , C-2-L, C-3-L, CBP and BCP are as follows.

[ Comparative example 1~3] Fabrication of green organic EL devices

A green organic EL device was manufactured in the same process as Example 1, except that CBP, C-2-L, or C-3-L was used instead of compound Mat-6 as the light-emitting host material when forming the light-emitting layer.

[ Evaluation example ]

For each green organic EL device manufactured in Examples 1 to 47 and Comparative Example 1, the driving voltage, current efficiency, and luminescence peak at a current density (10) mA/cm2 were measured, and the results are shown in Table 1 below. It was.

Sample host driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 Mat 6 6.80 516 41.2 Example 2 Mat 8 6.77 516 42.3 Example 3 Mat 9 6.83 516 40.7 Example 4 Mat 10 6.80 516 40.8 Example 5 Mat 16 6.87 516 41.5 Example 6 Mat 20 6.79 516 41.5 Example 7 Mat 27 6.81 516 40.6 Example 8 Mat 31 6.80 516 40.2 Example 9 Mat 53 6.80 516 40.1 Example 10 Mat 64 6.81 516 41.3 Example 11 Mat 80 6.80 516 40.6 Example 12 Mat 136 6.80 516 41.5 Example 13 Mat 139 6.80 516 40.6 Example 14 Mat 155 6.71 516 40.2 Example 15 Mat 181 6.79 516 40.1 Example 16 Mat 244 6.81 516 41.3 Example 17 Mat 246 6.80 516 40.2 Example 18 Mat 250 6.80 516 40.1 Example 19 Mat 273 6.77 516 41.3 Example 20 Mat 290 6.83 516 41.2 Example 21 Mat 321 6.80 516 42.3 Example 22 Mat 340 6.80 516 40.7 Example 23 Mat 349 6.79 516 40.8 Example 24 Mat 365 6.81 516 41.5 Example 25 Mat 373 6.80 516 41.5 Example 26 Mat 419 6.80 516 40.6 Example 27 Mat 460 6.81 516 40.2 Example 28 Mat 513 6.80 516 40.1 Example 29 Mat 531 6.80 516 41.3 Example 30 Mat 540 6.80 516 40.6 Example 31 Mat 550 6.71 516 41.5 Example 32 Mat 579 6.79 516 40.6 Example 33 Mat 592 6.81 516 40.2 Example 34 Mat 605 6.80 516 40.1 Example 35 Mat 611 6.77 516 41.3 Example 36 Mat 619 6.83 516 41.2 Example 37 Mat 664 6.80 516 42.3 Example 38 Mat 678 6.80 516 40.7 Example 39 Mat 722 6.79 516 40.8 Example 40 Mat 724 6.80 516 41.5 Example 41 Mat 725 6.80 516 40.6 Example 42 Mat 742 6.71 516 40.2 Example 43 Mat 747 6.79 516 40.1 Example 44 Mat 773 6.80 516 42.3 Example 45 Mat 777 6.80 516 40.7 Example 46 Mat 782 6.79 516 40.8 Example 47 Mat 783 6.80 516 40.7 Comparative Example 1 CBP 6.93 516 38.2 Comparative Example 2 C-2-L 6.88 516 37.8 Comparative Example 3 C-3-L 6.86 516 38.9

As shown in Table 1, when the compounds according to the present invention (Mat-6 to MAt-783) were used as the emitting layer of a green organic EL device (Example 1-47), conventional CBP, C-2-L, C Compared to the green organic EL device using -3-L (Comparative Examples 1 to 3), it can be seen that it exhibits better performance in terms of efficiency and driving voltage.

[ Example 48 ~ 78] Fabrication of red organic EL devices

The compound synthesized in the synthesis example was purified to high purity by sublimation using a commonly known method, and then a red organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a 1500Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaning the substrate for 5 minutes using UV, and vacuum evaporation. The substrate was transferred to .

On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/Compound of Mat 11 ~ Mat 780 + 10% (piq) ₂ Ir(acac) (30nm)/BCP (10 nm)/Alq ₃ An organic electroluminescent device was manufactured by stacking (30 nm)/LiF (1 nm)/Al (200 nm) in that order.

[ Comparative example 4~6] Fabrication of red organic EL device

A red organic electroluminescent device was manufactured in the same process as Example 48, except that CBP was used instead of the compound of Synthesis Example 4 as the light-emitting host material when forming the light-emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir(acac), C-2-LQ, C-3-LQ, CBP, and BCP used in Examples 48 to 78 and Comparative Examples 4 to 6 are as follows.

[ Evaluation example ]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each organic electroluminescent device manufactured in Examples 48 to 78 and Comparative Examples 4 to 6, and the results are shown in Table 2 below.

Sample host Driving voltage (V) Current efficiency (cd/A) Example 48 Mat 11 5.11 9.0 Example 49 Mat 33 4.99 8.6 Example 50 Mat 50 4.98 9.0 Example 51 Mat 61 5.14 8.6 Example 52 Mat 66 5.00 9.4 Example 53 Mat 83 5.12 9.5 Example 54 Mat 127 4.80 9.1 Example 55 Mat 138 5.12 8.9 Example 56 Mat 156 4.80 8.9 Example 57 Mat 186 5.11 9.1 Example 58 Mat 235 4.99 9.0 Example 59 Mat 331 4.98 8.6 Example 60 Mat 342 5.00 9.3 Example 61 Mat 350 5.00 9.0 Example 62 Mat 370 5.12 8.8 Example 63 Mat 374 4.98 8.9 Example 64 Mat 390 5.14 9.1 Example 65 Mat 421 5.11 9.0 Example 66 Mat 461 4.99 8.6 Example 67 Mat 472 4.80 8.9 Example 68 Mat 504 5.11 9.1 Example 69 Mat 580 4.99 9.0 Example 70 Mat 600 5.00 9.4 Example 71 Mat 612 5.12 9.5 Example 72 Mat 618 5.12 9.5 Example 73 Mat 627 4.80 9.1 Example 74 Mat 667 5.12 8.9 Example 75 Mat 685 5.14 8.6 Example 76 Mat 715 5.00 9.4 Example 77 Mat 774 5.12 9.5 Example 78 Mat 780 5.11 9.1 Comparative Example 4 CBP 5.25 8.2 Comparative Example 5 C-2-LQ 5.31 7.8 Comparative Example 6 C-3-LQ 5.27 8.0

As shown in Table 2, when the compound according to the present invention was used as a material for the emitting layer of a red organic electroluminescent device (Examples 48-78), conventional CBP, C-2-LQ, and C-3-LQ were used as the emitting layer. Compared to the red organic electroluminescent device (4-6) used as a material, it can be seen that it exhibits excellent performance in terms of efficiency and driving voltage.

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer

Claims (14)

Compound, represented by formula 6:
[Formula 6]

In Formula 6 above.
Y is C(R ₅ )(R ₆ ),
p and q are integers from 0 to 3;
r and m are integers from 0 to 4;
L ₁ is a direct bond, an unsubstituted or phenyl group-substituted phenylene group or biphenylene group,
L ₂ is a phenylene group or biphenylene group,
R ₁ is hydrogen, a phenyl group, a dibenzofuran group, or a carbazole group,
R ₂ is hydrogen or a biphenyl group, R ₃ and R ₄ are hydrogen, and R ₅ and R ₆ are methyl groups;
Ar ₁ is a substituent represented by the following formula (11);

[Formula 11]

Z ₁ and Z ₅ are N, Z ₂ and Z ₄ are C(R ₇ ), and if one of Z ₂ or R ₇ of Z ₄ forms a benzene ring with Z ₃ , the other is a phenyl group and Z ₃ is C (R ₇ ) and at least one of R ₁ or R ₂ is not hydrogen,
Z ₁ and Z ₅ are N, Z ₂ and Z ₄ are C(R ₇ ), and if one of R ₇ of Z ₂ or Z ₄ does not form a benzene ring with Z ₃ , R ₇ of Z ₂ or Z ₄ One of them is a phenyl group, the other is a dibenzofuran group, and Z ₃ is N.
delete delete delete delete delete delete delete delete delete delete According to paragraph 1,
The compound is characterized in that it is selected from the group consisting of the following compounds:







An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the one or more organic layers includes the compound represented by the formula (6) of claim 1.
According to clause 13,
The organic material layer includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.

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