WO2014104665A1 - Organic compound and organic electroluminescent element including same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent element including the same, and the organic electroluminescent element has improved light-emitting efficiency, driving voltage, and lifespan or the like by introducing, to the organic electroluminescent element, a light-emitting layer which uses the organic compound as a host material.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and to an organic electroluminescent device in which the luminous efficiency, driving voltage and the like of the device are improved.

From the observation of organic thin-film emission by Bernanose in the 1950s, research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') has been continued by blue electroluminescence using anthracene single crystals in 1965. . In 1987, Tang presented an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, long life organic EL device, it has evolved to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp). Metal complex compounds containing Ir, such as ₂ , are used. To date, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of luminescence properties, but due to low glass transition temperature and low thermal stability, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of the material which is more excellent in performance is calculated | required.

It is an object of the present invention to provide a novel organic compound which is excellent in thermal stability due to a high glass transition temperature and can improve the binding force between holes and electrons.

In addition, an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.

The present invention provides a compound represented by Formula 1:

Formula 1

In Chemical Formula 1,

R ₃ to R ₆ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl phosphine group, Substituted or unsubstituted C _{6 Through} C ₄₀ An arylphosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring,

Provided that at least one of R ₃ and R _4, R ₄ and R _5, and R ₅ and R ₆ may be bonded to each other to form a condensed ring represented by Formula 2 below;

Formula 2

In Chemical Formula 2,

The dotted line is a site where condensation occurs with the compound of Formula 1;

R ₁ , R ₂ , and R ₇ to R ₁₀ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C Alkenyl group of ₂ to C ₄₀ , substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted A C ₆ to C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group may be selected, or may be combined with an adjacent group to form a condensed ring;

n is an integer from 0 to 4, and if n is an integer from 1 to 4, at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C Alkenyl group of ₂ to C ₄₀ , substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or An unsubstituted C ₆ -C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

X ₁ and X ₂ are each independently selected from O, S, Se, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ ) and ;

Ar ₁ to Ar ₃ are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group , Substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and Substituted or unsubstituted C ₆ ~ C _{40 It} is selected from the group consisting of arylsilyl group;

In R ₁ to R _10, Ra, and Ar ₁ to Ar ₃ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl jade C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ of is selected from the group consisting arylsilyl It may be substituted with one or more substituents, where the substituents may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, characterized in that at least one of the at least one organic layer comprises the compound. An organic electroluminescent device is provided.

Here, at least one of the one or more organic material layers containing the compound is preferably a light emitting layer.

Since the compound represented by Formula 1 according to the present invention has excellent thermal stability and phosphorescence properties, it may be used as a material of the organic material layer of the organic EL device. In particular, when the compound represented by Chemical Formula 1 according to the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.

Hereinafter, the present invention will be described in detail.

The novel compound according to the present invention forms a basic skeleton by fusion of an indole moiety at the end of an indenoindole moiety, and a structure in which various substituents are bonded to the basic skeleton, represented by Chemical Formula 1 It is characterized by.

The compound represented by Chemical Formula 1 is a structure in which an indole moiety having a large electron donor is bonded to an end of an indenoindole moiety. Various aromatic ring substituents having electrophoretic (Electron Withdrawing) properties can enhance the binding force between holes and electrons while the entire molecule has bipolar properties. Therefore, when the compound is applied to the organic EL device, since it can exhibit excellent properties as a host material of the light emitting layer compared to the conventional CBP, the phosphorescence property of the device is improved, and at the same time, the hole injection capacity and / or transport capacity, luminous efficiency, Driving voltage, lifespan characteristics and the like can be improved. In addition, the energy level may be adjusted according to the substituents to have a wide band gap (sky blue to red), and thus may be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, and the like.

On the other hand, in the phosphorescent layer of the organic EL device, the host material should have a triplet energy gap of the host higher than the dopant. That is, in order to effectively provide phosphorescence from the dopant, the lowest excited state of the host must be higher in energy than the lowest emitted state of the dopant. The compound represented by Formula 1 of the present invention has an indole moiety as a central skeleton and has triplet energy suitable for phosphorescence emission.

In addition, the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the bound indole moiety, thereby improving glass transition temperature, and thus, the conventional CBP (4,4). -dicarbazolybiphenyl) may have a higher thermal stability. In addition, by infusing an indole moiety bound to the end of an indenoindole moiety, thermal stability of the compound may be improved and crystallization of the organic material layer including the compound of Formula 1 may be improved. Effective at suppressing Therefore, the organic EL device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.

In addition, when the compound represented by the formula (1) according to the present invention is adopted as a material of the hole injection / transport layer of the organic EL device, phosphorescent host material of blue, green and / or red, the efficiency and lifespan are superior to the conventional CBP. It can be effective. Therefore, the compound represented by Formula 1 of the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the life of the organic EL device has a great effect on maximizing the performance in the full color organic light emitting panel.

In the compound represented by Formula 1, R ₃ to R ₆ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted A C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted nuclear atom having 5 to 40 Heteroaryl group, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted Or an unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C of ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ Ah Phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine the oxide group, and a substituted or unsubstituted C ₆ ~ selected from the group consisting arylsilyl of C ₄₀ or, or near the condensed ring groups bonded to Can be formed.

At this time, in the above R ₃ to R ₆ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron Group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ one or more selected from the group consisting of C ₄₀ aryl silyl group of Itdoe may be substituted with a group, when the substituent group of a plurality, may be identical to or different from each other.

Preferably, R ₃ to R ₆ are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.

However, at least one of R ₃ and R _4, R ₄ and R _5, and R ₅ and R ₆ may be bonded to each other to form a condensed ring represented by Formula 2 above. For example, when R ₃ and R ₄ combine with each other to form a condensed ring represented by Formula 2, a compound represented by Formula 3 or 4 below is formed.

In Chemical Formula 2, a dotted line means a site where condensation occurs with at least one of R ₃ and R _4, R ₄ and R _5, and R ₅ and R ₆ of Chemical Formula 1.

R ₁ , R ₂ , and R ₇ to R ₁₀ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted number of 5 to 40 heteroaryl unsubstituted nucleus atoms Aryl group, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or Unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ An alkylboron group of -C ₄₀ , a substituted or unsubstituted C ₆ -C ₄₀ arylboron group, a substituted or unsubstituted C ₆ -C ₄₀ arylphosphine group, a substituted or Unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted aryl selected from the group consisting of a silyl C ₆ ~ C ₄₀ of the ring or, or in adjacent groups combine to form a condensed ring.

In this case, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, in R ₁ , R ₂ , and R ₇ to R ₁₀ , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenes group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of the , C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group is selected from, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group consisting of and It may be substituted with one or more substituents, when there are a plurality of substituents, they may be the same or different from each other.

Preferably, R ₁ , R ₂ , and R ₇ to R ₁₀ are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.

N is an integer of 0 to 4. When n is 0, it means that hydrogen is not substituted by the substituent Ra. In addition, when n is an integer of 1 to 4, hydrogen is substituted with a substituent Ra, and at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or Unsubstituted C ₂ to C ₄₀ alkenyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted nuclear atom 5 to 5 40 heteroaryl groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy groups, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy groups, substituted or unsubstituted C ₆ -C ₄₀ arylamine groups , Substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ A arylphosphine group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or a condensed ring in combination with an adjacent group Can be formed.

In this case, in the Ra, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkyl boron group, an aryl boron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 ~ 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ values in the aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group with one or more substituents selected from the group consisting of In the case of plural substituents, the substituents may be the same as or different from each other.

Preferably n is an integer of 0 to 4, when n is an integer of 1 to 4, one or more Ra may be selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.

In the compound represented by Formula 1, X ₁ and X ₂ are each independently selected from O, S, Se, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ ), wherein X ₁ and X ₂ At least one is N (Ar ₁ ), preferably X ₁ and X ₂ may both be N (Ar ₁ ).

Ar ₁ to Ar ₃ are the same as or different from each other, and each independently substituted or unsubstituted C ₁ ~ C ₄₀ Alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ Alkenyl group, substituted or unsubstituted C ₂ Alkynyl group of -C ₄₀ , substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group of 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ -C ₄₀ aryl jade Periodic, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted aryl phosphine oxide of a C ₆ ~ C ₄₀ ring And substituted or unsubstituted selected from the consisting of a arylsilyl a C ₆ ~ C ₄₀ ring group, and considering the luminous efficiency and lifetime of the organic EL device, the said Ar ₁ to Ar ₃ same or different, each independently It is preferably selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms.

In Ar ₁ to Ar ₃ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, Aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ aryl An amine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ optionally substituted with at least one selected from the group consisting of aryl silyl It may be substituted by, wherein if the plurality of substituents may be the same or different from each other.

More preferably, Ar ₁ to Ar ₃ may be the same as or different from each other, and each independently selected from the group consisting of structures represented by the following substituents S1 to S206, but is not limited thereto.

Examples of the compound represented by Formula 1 according to the present invention include, but are not limited to, compounds represented by the following Formulas 3 to 8.

Formula 3

Formula 4

Formula 5

Formula 6

Formula 7

Formula 8

In Chemical Formulas 3 to 8,

R ₁ to R ₁₀ , Ra, X ₁ and X ₂ , Ar ₁ to Ar ₃ and n are the same as defined in Chemical Formula 1, respectively.

Meanwhile, "alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, and iso-amyl. And hexyl.

In the present invention, "alkenyl" is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl, and the like.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond, and examples thereof include ethynyl, 2-propynyl etc. are mentioned.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are attached to each other (pendant) or fused (fused) may also be included, and further construed to include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure. Interpret as included. Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include morpholine, piperazine and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.

Compounds of Formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by Formula 1, preferably a compound represented by Formula 3 to Formula 8.

Specifically, the present invention is an organic electroluminescent device comprising an anode (anode), a cathode (cathode) and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic material layer is It includes a compound represented by the formula (1), preferably a compound represented by the formula (3) to (8). In this case, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1). At this time, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer.

According to an example of the present invention, the light emitting layer of the organic electroluminescent device of the present invention may include a host material, wherein the host material may include the compound of formula (1). As such, when the compound of Formula 1 is included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.

The structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be. Specifically, the compound represented by Formula 1 of the present invention may be used as a phosphorescent host material of the light emitting layer. In some cases, an electron injection layer may be further stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention may be formed using other materials and methods known in the art, except that one or more layers (eg, a light emitting layer) of the organic material layer are formed to include the compound represented by Chemical Formula 1. It can be prepared by forming an organic layer and an electrode.

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

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of Compounds IIC-1 & IIC-2

Step 1 Synthesis of 8-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole

(4-bromophenyl) hydrazine hydrochloride (223.5g, 1.0mol) was added to the reactor, followed by addition of acetic acid (1,000ml) and stirring. 3,3-dimethyl-2,3-dihydro-1H-inden-1-one (160.2g, 1.0mol) was added dropwise to the reactor and mixed, followed by stirring at 130 ° C for 12 hours.

After the reaction was completed, the solvent was concentrated under reduced pressure, the organic layer was extracted with ethyl acetate, water was removed from the organic layer with MgSO ₄ , and purified by column chromatography (Hexane: EA = 4: 1 (v / v)). 8-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (231 g, yield: 74%) was obtained.

¹ H-NMR: δ 1.82 (s, 6H), 7.34 (m, 3H), 7.57 (m, 3H), 8.10 (s, 1H), 11.36 (b, 1H)

Step 2 of 10,10-dimethyl-8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole synthesis

8-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (25 g, 8 mmol), 4,4,4 ', 4' obtained under <Step 1> under a nitrogen stream , 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (24.4 g, 9.6 mmol), Pd (dppf) Cl ₂ (1.75 g, 2.4 mmol), KOAc (23.57 g, 0.24 mol) and 1,4-Dioxane (500 ml) were mixed and then stirred at 130 ° C. for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, water was removed from the organic layer with MgSO ₄ , and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 10,10-dimethyl. -8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (22.35 g, yield: 76%) Got it.

¹ H-NMR: δ 1.21 (s, 12H) 1.70 (s, 6H), 7.34 (m, 4H), 7.60 (m, 2H), 7.75 (s, 1H), 11.36 (b, 1H)

Step 3 Synthesis of 10,10-dimethyl-8- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole

2-bromo-1-nitrobenzene (24.2 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-8- (4,4,5,5-tetramethyl-1,3,2- obtained in <Step 2> above dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol), and THF / H ₂ O (200 ml / 50 ml) After mixing, Pd (PPh ₃ ) ₄ (3.3 g, 3mmol) was added and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-8- (2-nitrophenyl) -5,10-dihydroindeno [1,2 -b] indole (23.7 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.37 (m, 3H), 7.73 (m, 4H), 7.75 (s, 1H), 8.01 (m, 4H), 11.36 (b, 1H)

Step 4 Synthesis of 10,10-dimethyl-8- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole

10,10-dimethyl-8- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol), iodobenzene (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and then stirred at 190 ° C. for 12 hours.

After the reaction was terminated, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give 10,10-dimethyl-8- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno -[1,2-b] indole (20.1 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.32 (m, 3H), 7.60 (m, 7H), 8.01 (m, 4H), 8.21 (m, 2H), 8.52 (m, 4H)

Step 5 Synthesis of Compounds IIC-1 and IIC-2

10,10-dimethyl-8- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole (20.10g 46.7mmol) and triphenylphosphine obtained in <Step 4> under a nitrogen stream (36.7g, 140.0mmol), and 1,2-dichlorobenzene (200 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to give compound IIC-1 (11.2 g, yield: 60%), and compound IIC-2 (3.7 g, Yield: 19.80%).

¹ H-NMR of compound IIC-1: δ 1.75 (s, 6H), 7.32-7.60 (m, 12H), 7.99 (m, 3H), 11.36 (b, 1H)

¹ H-NMR of compound IIC-2: δ 1.72 (s, 6H), 7.36-7.58 (m, 12H), 7.83 (s, 1H), 7.98 (s, 1H), 8.12 (d, 1H), 11.10 ( b, 1H)

Preparation Example 2 Synthesis of Compound IIC-3

Step 1 9-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole, and 7-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b ] indole synthesis

(3-bromophenyl) hydrazine hydrochloride (223.5 g, 1.0mol) was added to the reactor, followed by addition of acetic acid (1,000ml) and stirring. 3,3-dimethyl-2,3-dihydro-1H-inden-1-one (160.2 g, 1.0 mol) was added dropwise to the reactor and mixed, followed by stirring at 130 ° C. for 12 hours.

After the reaction was completed, the solvent was concentrated under reduced pressure, the organic layer was extracted with ethyl acetate, and then water was removed from the organic layer with MgSO ₄ , and purified by column chromatography (Hexane: EA = 8: 1 (v / v)). Compound A (9-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole) (68.7 g, yield: 22%), and Compound B (7-bromo-10,10-dimethyl -5,10-dihydroindeno [1,2-b] indole) (162.3 g, yield: 52%) was obtained.

¹ H-NMR of Compound A: δ 1.72 (s, 6H), 6.98 (dd, 1H), 7.31 (m, 3H), 7.52 (d, 1H), 7.61 (dd, 2H), 11.20 (b, 1H)

¹ H-NMR of Compound B: δ 1.71 (s, 6H), 7.36 (m, 3H), 7.60 (m, 2H), 7.83 (m, 2H), 11.30 (b, 1H)

Step 2 of 10,10-dimethyl-9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole synthesis

9-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (25 g, 8 mmol), 4,4,4 ', 4' obtained under <Step 1> under a nitrogen stream , 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (24.4 g, 9.6 mmol), Pd (dppf) Cl ₂ (1.75 g, 2.4 mmol), KOAc (23.57 g, 0.24 mol), and 1,4-Dioxane (500 ml) were mixed and then stirred at 130 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, water was removed from the organic layer with MgSO ₄ , purified by column chromatography (Hexane: EA = 10: 1 (v / v)), and 10,10-dimethyl-9 -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (22.35 g, yield: 76%) was obtained.

¹ H-NMR: δ 1.21 (s, 12H) 1.70 (s, 6H), 7.30 (m, 4H), 7.58 (m, 3H), 11.39 (b, 1H)

Step 3 Synthesis of 10,10-dimethyl-9- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole

2-bromo-1-nitrobenzene (24.2 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-9- (4,4,5,5-tetramethyl-1,3,2- obtained in <Step 2> above dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol), and THF / H ₂ O (200 ml / 50 ml) After mixing, Pd (PPh ₃ ) ₄ (3.3 g, 3mmol) was added and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-9- (2-nitrophenyl) -5,10-dihydroindeno [1,2 -b] indole (23.7 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.37 (m, 3H), 7.62 (m, 4H), 7.73 (m, 3H), 7.85 (d, 1H), 11.38 (b, 1H)

Step 4 Synthesis of 10,10-dimethyl-9- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole

10,10-dimethyl-9- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol), iodobenzene (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and then stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-9- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole (20.1 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.32 (m, 3H), 7.48 (m, 7H), 7.56 (m, 5H), 7.88 (d, 1H)

Step 5 Synthesis of Compound IIC-3

10,10-dimethyl-8- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole (20.10g 46.7mmol) and triphenylphosphine obtained in <Step 4> under nitrogen stream (36.7 g, 140.0 mmol), and 200 ml of 1,2-dichlorobenzene were mixed and then stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added thereto, and the organic layer was filtered. The solvent was removed from the obtained organic layer and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain a compound IIC-3 (11.2 g, yield: 60%).

¹ H-NMR of compound IIC-3: δ 1.71 (s, 6H) 7.34 (m, 3H), 7.43 (m, 7H), 7.52 (m, 4H), 8.08 (d, 1H), 11.32 (b, 1H )

Preparation Example 3 Synthesis of Compounds IIC-4 and IIC-5

<Step 1>

9-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole, 7-bromo-10,10-dimethyl-5, in the same manner as in <Step 1> of Preparation Example 2 10-dihydroindeno [1,2-b] indole was obtained.

Step 2 of 10,10-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole synthesis

7-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (25 g, 8 mmol), 4,4,4 ', 4' obtained under <Step 1> under a nitrogen stream , 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (24.4 g, 9.6 mmol), Pd (dppf) Cl ₂ (1.75 g, 2.4 mmol), KOAc (23.57 g, 0.24 mol), and 1,4-Dioxane (500 ml) were mixed and stirred at 130 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, and then water was removed from the organic layer with MgSO ₄ , and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 10,10-dimethyl-7. -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (22.35 g, yield: 76%) was obtained.

¹ H-NMR: δ 1.21 (s, 12H) 1.70 (s, 6H), 7.34 (m, 4H), 7.52 (m, 3H), 11.39 (b, 1H)

Step 3 Synthesis of 10,10-dimethyl-7- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole

2-bromo-1-nitrobenzene (24.2 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2- obtained in <Step 2> above dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol), and THF / H ₂ O (200 ml / 50 ml) After mixing, Pd (PPh ₃ ) ₄ (3.3 g, 3mmol) was added thereto and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give 10,10-dimethyl-7- (2-nitrophenyl) -5,10-dihydroindeno [1,2 -b] indole (23.7 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.37 (m, 3H), 7.62 (m, 4H), 7.73 (m, 2H), 7.85 (d, 1H), 8.04 (d, 1H), 11.38 (b , 1H)

Step 4 Synthesis of 10,10-dimethyl-7- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole

10,10-dimethyl-7- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol), iodobenzene (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-7- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole (20.1 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.32 (m, 3H), 7.48 (m, 7H), 7.56 (m, 4H), 7.88 (d, 1H), 8.08 (d, 1H)

Step 5 Synthesis of Compounds IIC-4 and IIC-5

10,10-dimethyl-8- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole (20.10g 46.7mmol) and triphenylphosphine obtained in <Step 4> under a nitrogen stream (36.7 g, 140.0 mmol), and 1,2-dichlorobenzene (200 ml) were mixed and then stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added thereto, and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to give compound IIC-4 (11.2 g, yield: 60%), and compound IIC-5 (3.7 g, Yield: 19.80%).

¹ H-NMR of compound IIC-4: δ 1.71 (s, 6H), 7.32 (m, 3H), 7.48 (m, 6H), 7.56 (m, 4H), 8.08 (d, 1H), 8.12 (s, 1H), 11.34 (b, 1H)

¹ H-NMR of compound IIC-5: δ 1.71 (s, 6H), 7.30 (m, 3H), 7.47 (m, 6H), 7.58 (m, 4H), 8.08 (d, 1H), 8.12 (d, 1H), 11.31 (b, 1H)

Preparation Example 4 Synthesis of Compound IIC-6

Step 1 Synthesis of 6-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole

(2-bromophenyl) hydrazine hydrochloride (223.5 g, 1.0mol) was added to the reactor, followed by addition of acetic acid (1,000 ml) and stirring. Then, 3,3-dimethyl-2,3-dihydro-1H-inden-1-one (160.2 g, 1.0 mol) was added dropwise to the reactor and mixed, followed by stirring at 130 ° C. for 12 hours.

After completion of the reaction, the solvent was concentrated under reduced pressure, the organic layer was extracted with ethyl acetate, water was removed from the organic layer with MgSO ₄ , and purified by column chromatography (Hexane: EA = 4: 1 (v / v)). bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (190 g, yield: 61%) was obtained.

¹ H-NMR: δ 1.82 (s, 6H), 6.80 (dd, 1H), 7.34 (m, 3H), 7.60 (m, 2H), 7.70 (d, 1H), 11.30 (b, 1H)

Step 2 of 10,10-dimethyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole synthesis

6-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (25 g, 8 mmol), 4,4,4 ', 4' obtained in <Step 1> under a nitrogen stream , 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (24.4 g, 9.6 mmol), Pd (dppf) Cl ₂ (1.75 g, 2.4 mmol), KOAc (23.57 g, 0.24 mol) and 1,4-Dioxane (500 ml) were mixed and then stirred at 130 ° C. for 12 hours.

After the reaction was terminated, the organic layer was extracted with ethyl acetate, water was removed from the organic layer with MgSO ₄ , purified by column chromatography (Hexane: EA = 10: 1 (v / v)), and 10,10-dimethyl-6. -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (22.35 g, yield: 76%) was obtained.

¹ H-NMR: δ 1.21 (s, 12H), 1.70 (s, 6H), 7.30 (m, 4H), 7.58 (m, 2H), 8.07 (d, 1H), 11.36 (b, 1H)

Step 3 Synthesis of 10,10-dimethyl-6- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole

2-bromo-1-nitrobenzene (24.2 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-6- (4,4,5,5-tetramethyl-1,3,2- obtained in <Step 2> above dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol) and THF / H ₂ O (200 ml / 50 ml) After mixing, Pd (PPh ₃ ) ₄ (3.3 g, ₃ mmol) was added thereto and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-6- (2-nitrophenyl) -5,10-dihydroindeno [1,2 -b] indole (23.7 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.39 (m, 3H), 7.59 (m, 4H), 7.70 (m, 2H), 7.82 (d, 1H), 8.06 (d, 1H), 11.38 ( b, 1H)

Step 4 Synthesis of 10,10-dimethyl-6- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole

10,10-dimethyl-6- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol), iodobenzene (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-6- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole (20.1 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H) 7.36 (m, 3H), 7.46 (m, 7H), 7.53 (m, 4H), 7.85 (d, 1H), 8.06 (d, 1H)

Step 5 Synthesis of Compound IIC-6

10,10-dimethyl-6- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole (20.10g 46.7mmol) and triphenylphosphine obtained in <Step 4> under nitrogen stream 36.7 g, 140.0 mmol), and 1,2-dichlorobenzene (200 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added thereto, and the organic layer was filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain the compound IIC-6 (11.2g, yield: 60%).

¹ H-NMR of compound IIC-6: δ 1.71 (s, 6H), 7.35 (m, 3H), 7.47 (m, 7H), 7.55 (m, 4H), 8.08 (d, 1H), 11.34 (b, 1H)

Preparation Example 5 Synthesis of Compound IIC7

<Steps 1 and 2>

6-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole, and 10,10-dimethyl, respectively, in the same manner as in <Step 1> and <Step 2> of Preparation Example 4 -6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole was obtained.

Step 3 Synthesis of 6- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole

2-bromo-4-chloro-1-nitrobenzene (28.4 g, 120 mmol) under a stream of nitrogen, 10,10-dimethyl-6- (4,4,5,5-tetramethyl-1, obtained in <Step 2>, 3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol) and THF / H ₂ O (200 ml / 50 ml) was mixed, Pd (PPh ₃ ) ₄ (3.3 g, ₃ mmol) was added thereto, and the mixture was stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give 6- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.39 (m, 2H), 7.42 (s, 1H), 7.44 (d, 1H), 7.59 (m, 4H), 7.82 (d, 1H), 8.06 ( d, 1 H), 11.38 (b, 1 H)

Step 4 Synthesis of 6- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole

6- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) and iodobenzene obtained in <Step 3> under a nitrogen stream (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give 6- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5 , 10-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.39 (m, 7H), 7.42 (s, 1H), 7.44 (d, 1H), 7.59 (m, 4H), 7.82 (d, 1H), 8.06 ( d, 1H)

Step 5 Synthesis of Compound IIC-7

6- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g 46.7 mmol) obtained in <Step 4> under a nitrogen stream ), Triphenylphosphine (36.7 g, 140.0 mmol), and 200 ml of 1,2-dichlorobenzene were mixed and then stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added thereto, and the organic layer was filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain the compound IIC-7 (12.2g, yield: 60%).

¹ H-NMR of compound IIC-7: δ 1.71 (s, 6H), 7.39 (m, 7H), 7.44 (d, 1H), 7.59 (m, 4H), 8.04 (s, 1H), 8.08 (d, 1H), 11.34 (b, 1H)

Preparation Example 6 Synthesis of Compounds IIC-8 and IIC-9

<Steps 1 and 2>

9-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole and 7-bromo-10,10-dimethyl-5, by performing the same procedure as in <Step 1> of Preparation Example 3 10-dihydroindeno [1,2-b] indole was obtained and performed in the same manner as in <Step 2> to 10,10-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl) -5,10-dihydroindeno [1,2-b] indole was obtained.

Step 3 Synthesis of 7- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole

2-bromo-4-chloro-1-nitrobenzene (28.4 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-7- (4,4,5,5-tetramethyl-1, obtained in <Step 2>, 3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol) and THF / H ₂ O (200 ml / 50 ml) was mixed, Pd (PPh ₃ ) ₄ (3.3 g, ₃ mmol) was added thereto, and the mixture was stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the organic layer obtained and purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 7- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.37 (m, 2H), 7.42 (s, 1H), 7.44 (d, 1H), 7.55 (m, 4H), 7.80 (d, 1H), 8.04 ( d, 1 H), 11.36 (b, 1 H)

Step 4 Synthesis of 7- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole

7- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) obtained in <Step 3> under nitrogen stream, iodobenzene (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 7- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5 , 10-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.37 (m, 7H), 7.42 (s, 1H), 7.44 (d, 1H), 7.55 (m, 4H), 7.80 (d, 1H), 8.04 ( d, 1H)

Step 5 Synthesis of Compounds IIC-8 and IIC-9

7- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8g 46.7mmol) obtained in <Step 4> under nitrogen stream ), Triphenylphosphine (36.7g, 140.0mmol), and 1,2-dichlorobenzene (200 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to give Compound IIC-8 (11.2 g, yield: 60%) and Compound IIC-9 (3.7 g, yield). : 19.80%) was obtained.

¹ H-NMR of compound IIC-8: δ 1.71 (s, 6H), 7.32 (m, 3H), 7.48 (m, 6H), 7.56 (m, 3H), 8.08 (s, 1H), 8.12 (s, 1H), 11.34 (b, 1H)

¹ H-NMR of compound IIC-9: δ 1.71 (s, 6H), 7.30 (m, 3H), 7.47 (m, 6H), 7.58 (m, 3H), 8.08 (s, 1H), 8.12 (d, 1H), 11.31 (b, 1H)

Preparation Example 7 Synthesis of Compounds IIC-10 and IIC-11

<Steps 1 and 2>

8-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole, and 10,10-dimethyl, respectively, in the same manner as in <Step 1> and <Step 2> of Preparation Example 1 -8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole was obtained.

Synthesis of 8- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole

2-bromo-4-chloro-1-nitrobenzene (28.4 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-8- (4,4,5,5-tetramethyl-1, obtained in <Step 2>, 3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol) and THF / H ₂ O (200 ml / 50 ml) was mixed, Pd (PPh ₃ ) ₄ (3.3 g, ₃ mmol) was added thereto, and the mixture was stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 8- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.36 (m, 2H), 7.42 (s, 1H), 7.44 (d, 1H), 7.58 (m, 4H), 7.82 (d, 1H), 8.04 ( s, 1 H), 11.38 (b, 1 H)

Step 4 Synthesis of 8- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole

8- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) obtained in <Step 3> under nitrogen stream, iodobenzene (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give 8- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5 , 10-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.37 (m, 7H), 7.42 (s, 1H), 7.44 (d, 1H), 7.55 (m, 4H), 7.80 (d, 1H), 8.04 ( s, 1 H)

Step 5 Synthesis of Compounds IIC-10 and IIC-11

8- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8g 46.7mmol), triphenylphosphine (36.7g, 140.0 mmol), and 1,2-dichlorobenzene (200 ml) were added thereto, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added thereto, and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to give compound IIC-10 (11.2 g, yield: 60%), and compound IIC-11 (3.7 g, Yield: 19.80%).

¹ H-NMR of compound IIC-10: δ 1.71 (s, 6H), 7.32 (m, 3H), 7.48 (m, 6H), 7.56 (m, 3H), 8.08 (d, 1H), 8.12 (s, 1H), 11.34 (b, 1H)

¹ H-NMR of compound IIC-11: δ 1.71 (s, 6H), 7.30 (m, 3H), 7.47 (m, 6H), 7.58 (m, 3H), 8.08 (s, 1H), 8.12 (s, 1H), 11.30 (b, 1H)

Preparation Example 8 Synthesis of Compound IIC-12

<Steps 1 and 2>

8-bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole, and 10,10-dimethyl, respectively, in the same manner as in <Step 1> and <Step 2> of Preparation Example 1 -8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole was obtained.

Step 3 Synthesis of 9- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole

2-bromo-4-chloro-1-nitrobenzene (28.4 g, 120 mmol) under nitrogen stream, 10,10-dimethyl-9- (4,4,5,5-tetramethyl-1, obtained in <Step 2>, 3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole (35.9 g, 100 mmol), NaOH (11.9 g, 300 mmol) and THF / H ₂ O (200 ml / 50 ml) was mixed, Pd (PPh ₃ ) ₄ (3.3 g, ₃ mmol) was added thereto, and the mixture was stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 9- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, yield: 67%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.39 (m, 3H), 7.42 (s, 1H), 7.44 (d, 1H), 7.59 (m, 4H), 7.82 (d, 1H), 11.38 ( b, 1H)

Step 4 Synthesis of 9- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole

9- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) and iodobenzene obtained in <Step 3> under a nitrogen stream (20.46 g, 100. mmol), Cu powder (2.1 g, 33.4 mmol), K ₂ CO ₃ (27.7 g, 200.6 mmol), and nitrobenzene (150 ml) were mixed and stirred at 190 ° C. for 12 hours.

After completion of the reaction, nitrobenzene was removed, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 9- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5 , 10-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%) was obtained.

¹ H-NMR: δ 1.71 (s, 6H), 7.39 (m, 8H), 7.42 (s, 1H), 7.44 (d, 1H), 7.59 (m, 4H), 7.82 (d, 1H)

Step 5 Synthesis of Compound IIC-12

9- (5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g 46.7 mmol) obtained in <Step 4> under a nitrogen stream ), triphenylphosphine (36.7 g, 140.0 mmol), and 1,2-dichlorobenzene (200 ml) were mixed and then stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was extracted with dichloromethane, MgSO ₄ was added, and the organic layer was filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain the compound IIC-12 (12.2g, yield: 60%).

¹ H-NMR of compound IIC-12: δ 1.71 (s, 6H), 7.39 (m, 8H), 7.40 (s, 1H), 7.44 (d, 1H), 7.59 (m, 3H), 8.04 (s, 1H), 11.34 (b, 1H)

Preparation Example 9-1 Synthesis of Compound IIC-7-1

Compound IIC-7 (5.2 g, 12.0 mmol), Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) synthesized in Preparation Example 5 under nitrogen stream After mixing, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-7-1 (4.45g, yield: 78%).

Preparation Example 9-2 Synthesis of Compound IIC-7-2

Compound IIC-7 (5.2 g, 12.0 mmol) synthesized in Preparation Example 5 under nitrogen stream. Pyridin-2-ylboronic acid (1.62g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) Put in and stirred at 80 ℃ for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-7-2 (3.54g, yield: 62%).

Preparation Example 9-3 Synthesis of Compound IIC-7-3

Compound IIC-7 (5.2g, 12.0mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) synthesized in Preparation Example 5 under nitrogen stream -9H-carbazole (4.88g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto. Stir at 80 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-7-3 (5.76g, yield: 75%).

Preparation Example 9-4 Synthesis of Compound IIC-7-4

Compound IIC-7 (5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol), synthesized in Preparation Example 5 under a nitrogen stream; and THF / H ₂ O (80 mL / 20 mL) was mixed, then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) was added and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-7-4 (4.53g, yield: 65%).

Preparation Example 10-1 Synthesis of Compound IIC-8-1

Compound IIC-8 (5.2 g, 12.0 mmol), Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) synthesized in Preparation Example 6 under nitrogen stream After mixing, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-8-1 (4.45g, yield: 78%).

Preparation Example 10-2 Synthesis of Compound IIC-8-2

Compound IIC-8 (5.2 g, 12.0 mmol), pyridin-3-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (synthesized in Preparation Example 6 under nitrogen stream) 80mL / 20mL) was mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-8-2 (3.54g, yield: 62%).

Preparation Example 10-3 Synthesis of Compound IIC-8-3

Compound IIC-8 (5.2g, 12.0mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) synthesized in Preparation Example 6 under nitrogen stream -9H-carbazole (4.88g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto. Stir at 80 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-8-3 (5.76g, yield: 75%).

Preparation Example 10-4 Synthesis of Compound IIC-8-4

Compound IIC-8 (5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 6 under a nitrogen stream and THF / H ₂ O (80mL / 20mL) was mixed, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-8-4 (4.53g, yield: 65%).

Preparation Example 11-1 Synthesis of Compound IIC-9-1

Compound IIC-9 (5.2 g, 12.0 mmol), Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) synthesized in Preparation Example 6 under nitrogen stream After mixing, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-9-1 (4.45g, yield: 78%).

Preparation Example 11-2 Synthesis of Compound IIC-9-2

Compound IIC-9 (5.2 g, 12.0 mmol), pyridin-2-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (synthesized in Preparation Example 6 under nitrogen stream) 80mL / 20mL) was mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-9-2 (3.54g, yield: 62%).

Preparation Example 11-3 Synthesis of Compound IIC-9-3

Compound IIC-9 (5.2g, 12.0mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) synthesized in Preparation Example 6 under nitrogen stream -9H-carbazole (4.88g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto. Stir at 80 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-9-3 (5.76 g, yield: 75%).

Preparation Example 11-4 Synthesis of Compound IIC-9-4

Compound IIC-9 (5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 6 under a nitrogen stream and THF / H ₂ O (80 mL / 20 mL) was mixed, then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) was added and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-9-4 (4.53g, yield: 65%).

Preparation Example 12-1 Synthesis of Compound IIC-10-1

Compound IIC-10 (5.2 g, 12.0 mmol), Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) synthesized in Preparation Example 7 under nitrogen stream After mixing, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-10-1 (4.45g, yield: 78%).

Preparation Example 12-2 Synthesis of Compound IIC-10-2

Compound IIC-10 (5.2 g, 12.0 mmol), pyridin-3-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (synthesized in Preparation Example 7 under nitrogen stream) 80mL / 20mL) was mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-10-2 (3.54g, yield: 62%).

Preparation Example 12-3 Synthesis of Compound IIC-10-3

Compound IIC-10 (5.2g, 12.0mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) synthesized in Preparation Example 7 under nitrogen stream -9H-carbazole (4.88g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto. Stir at 80 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-10-3 (5.76g, yield: 75%).

Preparation Example 12-4 Synthesis of Compound IIC-10-4

Compound IIC-10 (5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 7 under nitrogen stream and THF / H ₂ O (80mL / 20mL) was mixed, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-10-4 (4.53g, yield: 65%).

Preparation Example 13-1 Synthesis of Compound IIC-11-1

Compound IIC-11 (5.2 g, 12.0 mmol), Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) synthesized in Preparation Example 7 under nitrogen stream After mixing, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-11-1 (4.45g, yield: 78%).

Preparation Example 13-2 Synthesis of Compound IIC-11-2

Compound IIC-11 (5.2 g, 12.0 mmol), pyridin-2-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (synthesized in Preparation Example 7 under nitrogen stream) 80mL / 20mL) was mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-11-2 (3.54g, yield: 62%).

Preparation Example 13-3 Synthesis of Compound IIC-11-3

Compound IIC-11 (5.2g, 12.0mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) synthesized in Preparation Example 7 under nitrogen stream -9H-carbazole (4.88g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto. Stir at 80 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-11-3 (5.76g, yield: 75%).

Preparation Example 13-4 Synthesis of Compound IIC-11-4

Compound IIC-11 (5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 7 under nitrogen stream and THF / H ₂ O (80mL / 20mL) was mixed, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-11-4 (4.53g, yield: 65%).

Preparation 14-1 Synthesis of Compound IIC-12-1

Compound IIC-12 (5.2 g, 12.0 mmol), Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) synthesized in Preparation Example 8 under nitrogen stream After mixing, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-12-1 (4.45g, yield: 78%).

Preparation Example 14-2 Synthesis of Compound IIC-12-2

Compound IIC-12 (5.2 g, 12.0 mmol), pyridin-3-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (synthesized in Preparation Example 8 under nitrogen stream) 80mL / 20mL) was mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-12-2 (3.54g, yield: 62%).

Preparation 14-3 Synthesis of Compound IIC-12-3

Compound IIC-12 (5.2g, 12.0mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) synthesized in Preparation Example 8 under nitrogen stream -9H-carbazole (4.88g, 13.2mmol), NaOH (1.44g, 36.0mmol) and THF / H ₂ O (80mL / 20mL) were mixed, and then Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto. Stir at 80 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-12-3 (5.76g, yield: 75%).

Preparation 14-4 Synthesis of Compound IIC-12-4

Compound IIC-12 (5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 8 under nitrogen stream and THF / H ₂ O (80mL / 20mL) was mixed, Pd (PPh ₃ ) ₄ (693mg, 0.600mmol) was added thereto, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and the organic layer was filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to give the compound IIC-12-4 (4.53g, yield: 65%).

Synthesis Example 1 Synthesis of Compound 1

Compound IIC-1 (5.0 g, 12.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.8 mmol), NaH (0.45 g), synthesized in Preparation Example 1 under nitrogen stream , 18.8 mmol) and DMF (100 ml) were mixed and stirred at room temperature for 3 hours.

After the reaction was completed, water was added and the solid product was filtered and purified by column chromatography to obtain Compound 1 (5.06 g, yield: 64%).

GC-Mass (Theoretical value: 629.26 g / mol, Measured value: 629 g / mol)

Synthesis Example 2 Synthesis of Compound 2

Compound IIC-1 (3.0 g, 7.5 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.38 g, 11.3 mmol) synthesized in Preparation Example 1 under a nitrogen stream, Cu powder (0.24 g, 3.75 mmol), K ₂ CO ₃ (1.28 g, 22.5 mmol), Na ₂ SO ₄ (3.1 g, 22.5 mmol) and nitrobenzene (50 ml) were mixed and stirred at 190 ° C. for 12 hours. .

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . After removing the solvent of the organic layer was purified by column chromatography to give the compound 2 (3.2 g, yield: 61%).

GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol)

Synthesis Example 3 Synthesis of Compound 3

Compound IIC-1 (3.0 g, 7.5 mmol), 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.74 g), synthesized in Preparation Example 1 under nitrogen stream. , 11.3 mmol), Pd (OAc) ₂ (0.17 g, 0.75 mmol), NaO (t-bu) (2.2 g, 22.5 mmol), P (t-bu) ₃ (0.34 g, 1.5 mmol) and Toluene (50 ml) were mixed and then stirred at 110 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with ethyl acetate, the water was removed from the organic layer with MgSO ₄ and purified by column chromatography (Hexane: EA = 1: 1 (v / v)) to give compound 3 (3.74 g, yield). : 64%).

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 4 Synthesis of Compound 4

2- (3'-chlorobiphenyl-3-yl) -4,6- instead of 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 3 Except for using diphenyl-1,3,5-triazine (4.75 g, 11.3 mmol), the same procedure as in Synthesis Example 3 was carried out to obtain compound 4 (3.59 g, yield: 61%).

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 5 Synthesis of Compound 5

Except for using 2-bromo-4,6-diphenylpyridine (3.506 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Was obtained in the same manner as in Synthesis Example 2 to obtain compound 5 (2.3 g, yield: 48%).

GC-Mass (Theoretical value: 627.27 g / mol, Measured value: 627 g / mol)

Synthesis Example 6 Synthesis of Compound 6

2- (3-chlorophenyl) -4,6-diphenylpyridine (3.86 g, instead of 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 3 11.3 mmol), except that Compound 6 (2.3 g, yield: 44%) was obtained in the same manner as in Synthesis Example 3.

GC-Mass (Theoretical value: 703.30 g / mol, Measured value: 703 g / mol)

Synthesis Example 7 Synthesis of Compound 7

Except for using 2-bromo-4,6-diphenylpyrimidine (3.51 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Was obtained in the same manner as in Synthesis example 2 to obtain compound 7 (3.1 g, yield: 66%).

GC-Mass (Theoretical value: 628.26 g / mol, Measured value: 6282 g / mol)

Synthesis Example 8 Synthesis of Compound 8

2- (3-chlorophenyl) -4,6-diphenylpyrimidine (3.87 g, instead of 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 3 11.3 mmol) was used, and the same procedure as in Synthesis Example 3 was performed to obtain Compound 8 (2.65 g, yield: 50%).

GC-Mass (Theoretical value: 704.29 g / mol, Measured value: 704 g / mol)

Synthesis Example 9 Synthesis of Compound 9

Except for using 6-bromo-2,3'-bipyridine (2.66 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Then, compound 9 (1.66 g, yield: 40%) was obtained in the same manner as in Synthesis example 2.

GC-Mass (Theoretical value: 552.23 g / mol, Measured value: 552 g / mol)

Synthesis Example 10 Synthesis of Compound 10

Except for using 2-bromo-5-phenylpyridine (2.64 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, Compound 10 (2.03 g, yield: 49%) was obtained in the same manner as in Synthesis example 2.

GC-Mass (Theoretical value: 551.24 g / mol, Measured value: 551 g / mol)

Synthesis Example 11 Synthesis of Compound 11

Except for using 2- (3-bromophenyl) pyridine (2.64 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 , Compound 11 (2.36 g, yield: 57%) was obtained in the same manner as in Synthesis example 2.

GC-Mass (Theoretical value: 551.24 g / mol, Measured value: 551 g / mol)

Synthesis Example 12 Synthesis of Compound 12

Use of 3-bromo-9-phenyl-9H-carbazole (3.64 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Except for the same procedure as in Synthesis example 2, the compound 12 (3.37 g, yield: 70%) was obtained.

GC-Mass (Theoretical value: 639.27 g / mo, Measured value: 639 g / mol)

Synthesis Example 13 Synthesis of Compound 13

2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole (3.94 g instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 , 11.30 mmol) was obtained in the same manner as in Synthesis Example 2 to obtain Compound 13 (3.36 g, yield: 67%).

GC-Mass (Theoretical value: 666.28 g / mol, Measured value: 666 g / mol)

Synthesis Example 14 Synthesis of Compound 14

4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Except for using triazole (4.25 g, 11.30 mmol), to perform the same procedure as in Synthesis Example 2 compound 14 (3.13 g, yield: 60%) was obtained.

GC-Mass (Theoretical value: 693.29 g / mol, Measured value: 693 g / mol)

Synthesis Example 15 Synthesis of Compound 15

2-chloro-4-phenylquinazoline (2.71 g, 11.30 mmol) was used instead of 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 3. Except that, the same procedure as in Synthesis Example 3 was performed to obtain compound 15 (2.49 g, yield: 55%).

GC-Mass (Theoretical value: 602.25 g / mol, Measured value: 602 g / mol)

Synthesis Example 16 Synthesis of Compound 16

2- (3-chlorophenyl) -4-phenylquinazoline (3.58 g, 11.3 mmol instead of 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 3 Except for using), the same procedure as in Synthesis Example 3 was carried out to obtain compound 16 (3.07 g, yield: 60%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 17 Synthesis of Compound 17

4- (biphenyl-4-yl) -2-chloroquinazoline (3.57 g, instead of 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 3 11.30 mmol) was carried out in the same manner as in Synthesis Example 3, to obtain Compound 17 (2.24 g, yield: 44%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 18 Synthesis of Compound 18

Except for using 4-bromo-N, N-diphenylaniline (3.66 g, 11.3 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Was obtained in the same manner as in Synthesis example 2 to obtain compound 18 (2.61 g, yield: 54%).

GC-Mass (Theoretical value: 641.28 g / mol, Measured value: 641 g / mol)

Synthesis Example 19 Synthesis of Compound 19

N- (biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Compound 19 (3.71 g, yield: 62%) was obtained in the same manner as the Synthesis Example 2 except for using (5.38 g, 11.30 mmol).

GC-Mass (Theoretical value: 793.35 g / mol, Measured value: 793 g / mol)

Synthesis Example 20 Synthesis of Compound 20

N- (biphenyl-4-yl) -N- (4-bromophenyl) -9,9- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Except for using dimethyl-9H-fluoren-2-amine (5.84 g, 11.3 mmol), the same procedure as in Synthesis Example 2 was carried out to obtain compound 20 (4.39 g, yield: 70%).

GC-Mass (Theoretical value: 833.38 g / mol, Measured value: 833 g / mol)

Synthesis Example 21 Synthesis of Compound 21

Compound 21 (3.13 g) was carried out in the same manner as in Synthesis Example 1, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 1. , Yield: 66%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 22 Synthesis of Compound 22

A compound 22 (3.14 g) was obtained by the same procedure as in Synthesis Example 2, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 2. , Yield: 59%).

GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol)

Synthesis Example 23 Synthesis of Compound 23

A compound 23 (3.47 g) was prepared in the same manner as in Synthesis Example 3, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 3. , Yield: 59%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 24 Synthesis of Compound 24

Compound 24 (3.83 g) was carried out in the same manner as in Synthesis Example 4, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 4. , Yield: 65%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 25 Synthesis of Compound 25

Compound 25 (2.12 g) was prepared in the same manner as in Synthesis Example 11, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 11. , Yield: 51%).

GC-Mass (Theoretical value: 551.24 g / mol, Measured value: 551 g / mol)

Synthesis Example 26 Synthesis of Compound 26

Compound 26 (2.65 g) was prepared by the same procedure as in Synthesis Example 12, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 12. , Yield: 55%).

GC-Mass (Theoretical value: 639.27 g / mol, Measured value: 639 g / mol)

Synthesis Example 27 Synthesis of Compound 27

A compound 27 (2.81 g) was prepared by the same procedure as in Synthesis Example 15, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 15. , Yield: 62%).

GC-Mass (Theoretical value: 602.25 g / mol, Measured value: 602 g / mol)

Synthesis Example 28 Synthesis of Compound 28

Compound 28 (3.06 g) was carried out in the same manner as in Synthesis Example 16, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 16. , Yield: 60%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 29 Synthesis of Compound 29

Compound 29 (3.83g) was prepared in the same manner as in Synthesis Example 17, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 17. , Yield: 75%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 30 Synthesis of Compound 30

Compound 30 (3.59 g) was performed in the same manner as Synthesis Example 19, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 19. , Yield: 60%).

GC-Mass (Theoretical value: 793.35 g / mol, Measured value: 793 g / mol)

Synthesis Example 31 Synthesis of Compound 31

Compound 31 (3.95 g) was carried out in the same manner as in Synthesis Example 20, except that Compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of Compound IIC-1 used in Synthesis Example 20. , Yield: 63%).

GC-Mass (Theoretical value: 833.38 g / mol, Measured value: 833 g / mol)

Synthesis Example 32 Synthesis of Compound 32

Compound 32 (3.31 g) was carried out in the same manner as in Synthesis Example 1, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 1. , Yield: 70%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 33 Synthesis of Compound 33

Compound 33 (3.39 g) was prepared in the same manner as in Synthesis Example 2, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 2. , Yield: 64%).

GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol)

Synthesis Example 34 Synthesis of Compound 34

Compound 34 (3.59 g) was performed in the same manner as in Synthesis Example 3, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 3. , Yield: 61%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 35 Synthesis of Compound 35

Compound 35 (3.47 g) was prepared by the same procedure as in Synthesis Example 4, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 4. , Yield: 59%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 36 Synthesis of Compound 36

Compound 36 (1.61 g) was carried out in the same manner as in Synthesis Example 11, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 11. , Yield: 39%) was obtained.

GC-Mass (Theoretical value: 551.24 g / mol, Measured value: 551 g / mol)

Synthesis Example 37 Synthesis of Compound 37

Compound 37 (2.65 g) was carried out in the same manner as in Synthesis Example 12, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 12. , Yield: 55%).

GC-Mass (Theoretical value: 639.27 g / mol, Measured value: 639 g / mol)

Synthesis Example 38 Synthesis of Compound 38

Compound 38 (2.81 g) was carried out in the same manner as in Synthesis Example 15, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 15. , Yield: 62%).

GC-Mass (Theoretical value: 602.25 g / mol, Measured value: 602 g / mol)

Synthesis Example 39 Synthesis of Compound 39

Compound 39 (2.55g) was prepared in the same manner as in Synthesis Example 16, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 16. , Yield: 50%) was obtained.

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 40 Synthesis of Compound 40

Compound 40 (3.21g) was prepared in the same manner as in Synthesis Example 17, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 17. , Yield: 63%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 41 Synthesis of Compound 41

Compound 41 (3.28 g) was carried out in the same manner as in Synthesis Example 19, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 1. , Yield: 55%).

GC-Mass (Theoretical value: 793.35 g / mol, Measured value: 793 g / mol)

Synthesis Example 42 Synthesis of Compound 42

Compound 42 (3.76 g) was prepared in the same manner as in Synthesis Example 20, except that Compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of Compound IIC-1 used in Synthesis Example 20. , Yield: 60%).

GC-Mass (Theoretical value: 833.38 g / mol, Measured value: 833 g / mol)

Synthesis Example 43 Synthesis of Compound 43

Compound 43 (3.03 g) was carried out in the same manner as in Synthesis Example 1, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 1. , Yield: 64%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 44 Synthesis of Compound 44

Compound 44 (3.66 g) was prepared by the same procedure as in Synthesis Example 2, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 2. , Yield: 69%).

GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol)

Synthesis Example 45 Synthesis of Compound 45

Compound 45 (3.94 g) was performed in the same manner as in Synthesis Example 3, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 3. , Yield: 67%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 46 Synthesis of Compound 46

Compound 46 (3.65 g) was carried out in the same manner as in Synthesis Example 4, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 4. , Yield: 62%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 47 Synthesis of Compound 47

Compound 47 (1.78 g) was carried out in the same manner as in Synthesis Example 11, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 11. , Yield: 43%).

GC-Mass (Theoretical value: 551.24 g / mol, Measured value: 551 g / mol)

Synthesis Example 48 Synthesis of Compound 48

Compound 48 (2.65 g) was carried out in the same manner as in Synthesis Example 12, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 12. , Yield: 55%).

GC-Mass (Theoretical value: 639.27 g / mol, Measured value: 639 g / mol)

Synthesis Example 49 Synthesis of Compound 49

Compound 49 (3.17 g) was carried out in the same manner as in Synthesis Example 15, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 15. , Yield: 70%).

GC-Mass (Theoretical value: 602.25 g / mol, Measured value: 602 g / mol)

Synthesis Example 50 Synthesis of Compound 50

Compound 50 (3.17g) was prepared in the same manner as in Synthesis Example 16, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 16. , Yield: 62%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 51 Synthesis of Compound 51

A compound 51 (3.52g) was prepared in the same manner as in Synthesis Example 17, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 17. , Yield: 69%).

GC-Mass (Theoretical value: 678.28 g / mol, Measured value: 678 g / mol)

Synthesis Example 52 Synthesis of Compound 52

Compound 52 (4.45 g) was prepared in the same manner as in Synthesis Example 20, except that Compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 20. , Yield: 71%).

GC-Mass (Theoretical value: 833.38 g / mol, Measured value: 833 g / mol)

Synthesis Example 53 Synthesis of Compound 53

Compound 53 (3.23 g) was carried out in the same manner as in Synthesis Example 2, except that Compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 2. , Yield: 61%).

GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol)

Synthesis Example 54 Synthesis of Compound 54

Compound 54 (3.99 g) was carried out in the same manner as in Synthesis Example 3, except that Compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 3. , Yield: 68%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 55 Synthesis of Compound 55

Compound 55 (1.24 g) was carried out in the same manner as in Synthesis Example 11, except that Compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 11. , Yield: 30%).

GC-Mass (Theoretical value: 551.24 g / mol, Measured value: 551 g / mol)

Synthesis Example 56 Synthesis of Compound 56

Compound 56 (0.68 g) was carried out in the same manner as in Synthesis Example 15, except that Compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of Compound IIC-1 used in Synthesis Example 15. , Yield: 15%) was obtained.

GC-Mass (Theoretical value: 602.25 g / mol, Measured value: 602 g / mol)

Synthesis Example 57 Synthesis of Compound 57

A compound 57 (3.27 g) was prepared by the same procedure as in Synthesis Example 1, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 1. , Yield: 69%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 58 Synthesis of Compound 58

Compound 58 (4.24 g) was carried out in the same manner as in Synthesis Example 2, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 2. , Yield: 80%).

GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol)

Synthesis Example 59 Synthesis of Compound 59

Compound 59 (4.529 g) was carried out in the same manner as in Synthesis Example 3, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 3. , Yield: 77%).

GC-Mass (Theoretical value: 781.32 g / mol, Measured value: 781 g / mol)

Synthesis Example 60 Synthesis of Compound 60

Compound 60 (2.95 g) was carried out in the same manner as in Synthesis Example 15, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 15. , Yield: 65%).

GC-Mass (Theoretical value: 602.25 g / mol, Measured value: 602 g / mol)

Synthesis Example 61 Synthesis of Compound 61

A compound 61 (3.45 g) was prepared by the same procedure as in Synthesis Example 20, except that Compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of Compound IIC-1 used in Synthesis Example 20. , Yield: 55%).

GC-Mass (Theoretical value: 833.38 g / mol, Measured value: 833 g / mol)

Synthesis Example 62 Synthesis of Compound 62

Compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 62 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 63 Synthesis of Compound 63

Compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of compound IIC-1 used in Synthesis Example 2 and the same procedure as in Synthesis Example 2 was performed. 63 (3.76 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 64 Synthesis of Compound 64

Compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of compound IIC-1 used in Synthesis Example 3 and was subjected to the same procedure as in Synthesis Example 3 64 (3.91 g, yield: 72%) were obtained.

GC-Mass (Theoretical value: 858.04 g / mol, Measured value: 858 g / mol)

Synthesis Example 65 Synthesis of Compound 65

Except for using the compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9 instead of the compound IIC-1 used in Synthesis Example 15, the compound 65 ( 2.70 g, yield: 63%).

GC-Mass (Theoretical value: 678.82 g / mol, Measured value: 678 g / mol)

Synthesis Example 66 Synthesis of Compound 66

Compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 66 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 910.15 g / mol, Measured value: 910 g / mol)

Synthesis Example 67 Synthesis of Compound 67

Compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 67 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 706.83 g / mol, Measured value: 706 g / mol)

Synthesis Example 68 Synthesis of Compound 68

Compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 68 (3.75 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 782.93 g / mol, Measured value: 782 g / mol)

Synthesis Example 69 Synthesis of Compound 69

Compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of compound IIC-1 used in Synthesis Example 3 and the same procedure as in Synthesis Example 3 was performed. 69 (3.90 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 859.03 g / mol, Measured value: 859 g / mol)

Synthesis Example 70 Synthesis of Compound 70

Compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 70 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 679.81 g / mol, Measured value: 679 g / mol)

Synthesis Example 71 Synthesis of Compound 71

Compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was performed. 71 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 911.14 g / mol, Measured value: 911 g / mol)

Synthesis Example 72 Synthesis of Compound 72

Compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 72 (2.65 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 73 Synthesis of Compound 73

Compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of compound IIC-1 used in Synthesis Example 2 and was subjected to the same procedure as in Synthesis Example 2 73 (3.38 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 947.13 g / mol, Measured value: 947 g / mol)

Synthesis Example 74 Synthesis of Compound 74

Compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of compound IIC-1 used in Synthesis Example 3 and the same procedure as in Synthesis Example 3 was performed. 74 (3.45 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 1023.23 g / mol, Measured value: 1023 g / mol)

Synthesis Example 75 Synthesis of Compound 75

Compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15 75 (2.49 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 844.01 g / mol, Measured value: 844 g / mol)

Synthesis Example 76 Synthesis of Compound 76

Compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was performed. 76 (2.57 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1075.34 g / mol, Measured value: 1075 g / mol)

Synthesis Example 77 Synthesis of Compound 77

Compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 77 (2.73 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 811.99 g / mol, Measured value: 811 g / mol)

Synthesis Example 78 Synthesis of Compound 78

Compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of compound IIC-1 used in Synthesis Example 2, and a compound was prepared in the same manner as in Synthesis Example 2 78 (4.59 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 888.09 g / mol, Measured value: 888 g / mol)

Synthesis Example 79 Synthesis of Compound 79

Compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 79 (3.59 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 964.18 g / mol, Measured value: 964 g / mol)

Synthesis Example 80 Synthesis of Compound 80

Compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 80 (2.55 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 784.97 g / mol, Measured value: 784 g / mol)

Synthesis Example 81 Synthesis of Compound 81

Compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of compound IIC-1 used in Synthesis Example 1 and the same procedure as in Synthesis Example 20 was performed. 81 (2.68 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1016.30 g / mol, Measured value: 1016 g / mol)

Synthesis Example 82 Synthesis of Compound 82

Compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 82 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 83 Synthesis of Compound 83

Compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of compound IIC-1 used in Synthesis Example 2, and a compound was prepared in the same manner as in Synthesis Example 2 83 (3.76 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 84 Synthesis of Compound 84

Compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 64 (3.91 g, yield: 72%) were obtained.

GC-Mass (Theoretical value: 858.04 g / mol, Measured value: 858 g / mol)

Synthesis Example 85 Synthesis of Compound 85

Compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15 85 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 678.82 g / mol, Measured value: 678 g / mol)

Synthesis Example 86 Synthesis of Compound 86

Compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 86 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 910.15 g / mol, Measured value: 910 g / mol)

Synthesis Example 87 Synthesis of Compound 87

Compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 87 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 706.83 g / mol, Measured value: 706 g / mol)

Synthesis Example 88 Synthesis of Compound 88

Compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of compound IIC-1 used in Synthesis Example 2 and was subjected to the same procedure as in Synthesis Example 2 88 (3.75 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 782.93 g / mol, Measured value: 782 g / mol)

Synthesis Example 89 Synthesis of Compound 89

Compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 89 (3.90 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 859.03 g / mol, Measured value: 859 g / mol)

Synthesis Example 90 Synthesis of Compound 90

Compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15 90 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 679.81 g / mol, Measured value: 679 g / mol)

Synthesis Example 91 Synthesis of Compound 91

Compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 91 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 911.14 g / mol, Measured value: 911 g / mol)

Synthesis Example 92 Synthesis of Compound 92

Compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 92 (2.65 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 93 Synthesis of Compound 93

Compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 93 (3.38 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 947.13 g / mol, Measured value: 947 g / mol)

Synthesis Example 94 Synthesis of Compound 94

Compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 94 (3.45 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 1023.23 g / mol, Measured value: 1023 g / mol)

Synthesis Example 95 Synthesis of Compound 95

Compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15 95 (2.49 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 844.01 g / mol, Measured value: 844 g / mol)

Synthesis Example 96 Synthesis of Compound 96

Compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 96 (2.57 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1075.34 g / mol, Measured value: 1075 g / mol)

Synthesis Example 97 Synthesis of Compound 97

Compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 97 (2.73 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 811.99 g / mol, Measured value: 811 g / mol)

Synthesis Example 98 Synthesis of Compound 98

Compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of compound IIC-1 used in Synthesis Example 2 and the same procedure as in Synthesis Example 2 was performed. 98 (4.59 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 888.09 g / mol, Measured value: 888 g / mol)

Synthesis Example 99 Synthesis of Compound 99

Compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of compound IIC-1 used in Synthesis Example 3 and the same procedure as in Synthesis Example 3 was performed. 99 (3.59 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 964.18 g / mol, Measured value: 964 g / mol)

Synthesis Example 100 Synthesis of Compound 100

Compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 100 (2.55 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 784.97 g / mol, Measured value: 784 g / mol)

Synthesis Example 101 Synthesis of Compound 101

Compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 101 (2.68 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1016.30 g / mol, Measured value: 1016 g / mol)

Synthesis Example 102 Synthesis of Compound 102

Compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 102 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 103 Synthesis of Compound 103

Compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 103 (3.76 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 104 Synthesis of Compound 104

Compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 104 (3.91 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 858.04 g / mol, Measured value: 858 g / mol)

Synthesis Example 105 Synthesis of Compound 105

Compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 105 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 678.82 g / mol, Measured value: 678 g / mol)

Synthesis Example 106 Synthesis of Compound 106

Compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 106 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 910.15 g / mol, Measured value: 910 g / mol)

Synthesis Example 107 Synthesis of Compound 107

Compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 107 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 706.83 g / mol, Measured value: 706 g / mol)

Synthesis Example 108 Synthesis of Compound 108

Compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 108 (3.75 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 782.93 g / mol, Measured value: 782 g / mol)

Synthesis Example 109 Synthesis of Compound 109

Compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 109 (3.90 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 859.03 g / mol, Measured value: 859 g / mol)

Synthesis Example 110 Synthesis of Compound 110

Compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 110 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 679.81 g / mol, Measured value: 679 g / mol)

Synthesis Example 111 Synthesis of Compound 111

Compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 111 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 911.14 g / mol, Measured value: 911 g / mol)

Synthesis Example 112 Synthesis of Compound 112

Compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 112 (2.65 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 113 Synthesis of Compound 113

Compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 113 (3.38 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 947.13 g / mol, Measured value: 947 g / mol)

Synthesis Example 114 Synthesis of Compound 114

Compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 114 (3.45 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 1023.23 g / mol, Measured value: 1023 g / mol)

Synthesis Example 115 Synthesis of Compound 115

Compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was carried out to obtain a compound. 115 (2.49 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 844.01 g / mol, Measured value: 844 g / mol)

Synthesis Example 116 Synthesis of Compound 116

Compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 116 (2.57 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1075.34 g / mol, Measured value: 1075 g / mol)

Synthesis Example 117 Synthesis of Compound 117

Compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 117 (2.73 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 811.99 g / mol, Measured value: 811 g / mol)

Synthesis Example 118 Synthesis of Compound 118

Compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 118 (4.59 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 888.09 g / mol, Measured value: 888 g / mol)

Synthesis Example 119 Synthesis of Compound 119

Compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 119 (3.59 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 964.18 g / mol, Measured value: 964 g / mol)

Synthesis Example 120 Synthesis of Compound 120

Compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 120 (2.55 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 784.97 g / mol, Measured value: 784 g / mol)

Synthesis Example 121 Synthesis of Compound 121

Compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of compound IIC-1 used in Synthesis Example 1 and the same procedure as in Synthesis Example 20 was performed. 121 (2.68 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1016.30 g / mol, Measured value: 1016 g / mol)

Synthesis Example 122 Synthesis of Compound 122

Compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 122 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 123 Synthesis of Compound 123

Compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 123 (3.76 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 124 Synthesis of Compound 124

Compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of compound IIC-1 used in Synthesis Example 3 and was subjected to the same procedure as in Synthesis Example 3 124 (3.91 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 858.04 g / mol, Measured value: 858 g / mol)

Synthesis Example 125 Synthesis of Compound 125

Compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 125 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 678.82 g / mol, Measured value: 678 g / mol)

Synthesis Example 126 Synthesis of Compound 126

Compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 126 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 910.15 g / mol, Measured value: 910 g / mol)

Synthesis Example 127 Synthesis of Compound 127

Compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 127 (2.90 g, yield: 65%) were obtained.

GC-Mass (Theoretical value: 706.83 g / mol, Measured value: 706 g / mol)

Synthesis Example 128 Synthesis of Compound 128

Compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 128 (3.75 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 782.93 g / mol, Measured value: 782 g / mol)

Synthesis Example 129 Synthesis of Compound 129

Compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 129 (3.90 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 859.03 g / mol, Measured value: 859 g / mol)

Synthesis Example 130 Synthesis of Compound 130

Compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 130 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 679.81 g / mol, Measured value: 679 g / mol)

Synthesis Example 131 Synthesis of Compound 131

Compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was performed. 131 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 911.14 g / mol, Measured value: 911 g / mol)

Synthesis Example 132 Synthesis of Compound 132

Compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 132 (2.65 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 133 Synthesis of Compound 133

Compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 133 (3.38 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 947.13 g / mol, Measured value: 947 g / mol)

Synthesis Example 134 Synthesis of Compound 134

Compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used in place of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 134 (3.45 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 1023.23 g / mol, Measured value: 1023 g / mol)

Synthesis Example 135 Synthesis of Compound 135

Compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was carried out to obtain a compound. 135 (2.49 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 844.01 g / mol, Measured value: 844 g / mol)

Synthesis Example 136 Synthesis of Compound 136

Compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 136 (2.57 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1075.34 g / mol, Measured value: 1075 g / mol)

Synthesis Example 137 Synthesis of Compound 137

Compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 137 (2.73 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 811.99 g / mol, Measured value: 811 g / mol)

Synthesis Example 138 Synthesis of Compound 138

Compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 138 (4.59 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 888.09 g / mol, Measured value: 888 g / mol)

Synthesis Example 139 Synthesis of Compound 139

Compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 139 (3.59 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 964.18 g / mol, Measured value: 964 g / mol)

Synthesis Example 140 Synthesis of Compound 140

Compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 140 (2.55 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 784.97 g / mol, Measured value: 784 g / mol)

Synthesis Example 141 Synthesis of Compound 141

Compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of compound IIC-1 used in Synthesis Example 1 and the same procedure as in Synthesis Example 20 was performed. 141 (2.68 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1016.30 g / mol, Measured value: 1016 g / mol)

Synthesis Example 142 Synthesis of Compound 142

Compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 142 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 143 Synthesis of Compound 143

Compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of compound IIC-1 used in Synthesis Example 2 and the same procedure as in Synthesis Example 2 was performed. 143 (3.76 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 144 Synthesis of Compound 144

Compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 144 (3.91 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 858.04 g / mol, Measured value: 858 g / mol)

Synthesis Example 145 Synthesis of Compound 145

Compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 145 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 678.82 g / mol, Measured value: 678 g / mol)

Synthesis Example 146 Synthesis of Compound 146

Compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was carried out to obtain a compound. 146 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 910.15 g / mol, Measured value: 910 g / mol)

Synthesis Example 147 Synthesis of Compound 147

Compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 147 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 706.83 g / mol, Measured value: 706 g / mol)

Synthesis Example 148 Synthesis of Compound 148

Compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of compound IIC-1 used in Synthesis Example 2 and the same procedure as in Synthesis Example 2 was performed. 148 (3.75 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 782.93 g / mol, Measured value: 782 g / mol)

Synthesis Example 149 Synthesis of Compound 149

Compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of compound IIC-1 used in Synthesis Example 3 and the same procedure as in Synthesis Example 3 was performed. 149 (3.90 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 859.03 g / mol, Measured value: 859 g / mol)

Synthesis Example 150 Synthesis of Compound 150

Compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 150 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 679.81 g / mol, Measured value: 679 g / mol)

Synthesis Example 151 Synthesis of Compound 151

Compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was performed. 151 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 911.14 g / mol, Measured value: 911 g / mol)

Synthesis Example 152 Synthesis of Compound 152

Compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 152 (2.65 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 153 Synthesis of Compound 153

Compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 153 (3.38 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 947.13 g / mol, Measured value: 947 g / mol)

Synthesis Example 154 Synthesis of Compound 154

Compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used in place of compound IIC-1 used in Synthesis Example 3, and the same procedure as in Synthesis Example 3 was performed. 154 (3.45 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 1023.23 g / mol, Measured value: 1023 g / mol)

Synthesis Example 155 Synthesis of Compound 155

Compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 155 (2.49 g, yield: 63%) were obtained.

GC-Mass (Theoretical value: 844.01 g / mol, Measured value: 844 g / mol)

Synthesis Example 156 Synthesis of Compound 156

Compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 156 (2.57 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1075.34 g / mol, Measured value: 1075 g / mol)

Synthesis Example 157 Synthesis of Compound 157

Compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 157 (2.73 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 811.99 g / mol, Measured value: 811 g / mol)

Synthesis Example 158 Synthesis of Compound 158

Compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 158 (4.59 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 888.09 g / mol, Measured value: 888 g / mol)

Synthesis Example 159 Synthesis of Compound 159

Compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of compound IIC-1 used in Synthesis Example 3 and the same procedure as in Synthesis Example 3 was performed. 159 (3.59 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 964.18 g / mol, Measured value: 964 g / mol)

Synthesis Example 160 Synthesis of Compound 160

Compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 160 (2.55 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 784.97 g / mol, Measured value: 784 g / mol)

Synthesis Example 161 Synthesis of Compound 161

Compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was performed. 161 (2.68 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1016.30 g / mol, Measured value: 1016 g / mol)

 Synthesis Example 162 Synthesis of Compound 162

Compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as Synthesis Example 1 162 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 163 Synthesis of Compound 163

Compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 163 (3.76 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 781.94 g / mol, Measured value: 781 g / mol)

Synthesis Example 164 Synthesis of Compound 164

Compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 164 (3.91 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 858.04 g / mol, Measured value: 858 g / mol)

Synthesis Example 165 Synthesis of Compound 165

Compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 165 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 678.82 g / mol, Measured value: 678 g / mol)

Synthesis Example 166 Synthesis of Compound 166

Compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 166 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 910.15 g / mol, Measured value: 910 g / mol)

Synthesis Example 167 Synthesis of Compound 167

Compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 167 (2.90 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 706.83 g / mol, Measured value: 706 g / mol)

Synthesis Example 168 Synthesis of Compound 168

Compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 168 (3.75 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 782.93 g / mol, Measured value: 782 g / mol)

Synthesis Example 169 Synthesis of Compound 169

Compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of compound IIC-1 used in Synthesis Example 3 and the same procedure as in Synthesis Example 3 was performed. 169 (3.90 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 859.03 g / mol, Measured value: 859 g / mol)

Synthesis Example 170 Synthesis of Compound 170

Compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 170 (2.70 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 679.81 g / mol, Measured value: 679 g / mol)

Synthesis Example 171 Synthesis of Compound 171

Compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 171 (2.93 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 911.14 g / mol, Measured value: 911 g / mol)

Synthesis Example 172 Synthesis of Compound 172

Compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 172 (2.65 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 871.04 g / mol, Measured value: 871 g / mol)

Synthesis Example 173 Synthesis of Compound 173

Compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 3-3 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 173 (3.38 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 947.13 g / mol, Measured value: 947 g / mol)

Synthesis Example 174 Synthesis of Compound 174

Compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 3-3 was used in place of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 174 (3.45 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 1023.23 g / mol, Measured value: 1023 g / mol)

Synthesis Example 175 Synthesis of Compound 175

Compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used in place of compound IIC-1 used in Synthesis Example 15, and the same procedure as in Synthesis Example 15 was performed. 175 (2.49 g, yield: 63%) were obtained.

GC-Mass (Theoretical value: 844.01 g / mol, Measured value: 844 g / mol)

Synthesis Example 176 Synthesis of Compound 176

Compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used in place of compound IIC-1 used in Synthesis Example 20, and the same procedure as in Synthesis Example 20 was performed. 176 (2.57 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1075.34 g / mol, Measured value: 1075 g / mol)

Synthesis Example 177 Synthesis of Compound 177

Compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of compound IIC-1 used in Synthesis Example 1 and was subjected to the same procedure as in Synthesis Example 1 177 (2.73 g, yield: 65%) was obtained.

GC-Mass (Theoretical value: 811.99 g / mol, Measured value: 811 g / mol)

Synthesis Example 178 Synthesis of Compound 178

Compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used in place of compound IIC-1 used in Synthesis Example 2, and the same procedure as in Synthesis Example 2 was performed. 178 (4.59 g, yield: 76%) was obtained.

GC-Mass (Theoretical value: 888.09 g / mol, Measured value: 888 g / mol)

Synthesis Example 179 Synthesis of Compound 179

Compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of compound IIC-1 used in Synthesis Example 3, and a compound was prepared in the same manner as in Synthesis Example 3 179 (3.59 g, yield: 72%) was obtained.

GC-Mass (Theoretical value: 964.18 g / mol, Measured value: 964 g / mol)

Synthesis Example 180 Synthesis of Compound 180

Compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of compound IIC-1 used in Synthesis Example 15, and a compound was prepared in the same manner as in Synthesis Example 15. 180 (2.55 g, yield: 63%) was obtained.

GC-Mass (Theoretical value: 784.97 g / mol, Measured value: 784 g / mol)

Synthesis Example 181 Synthesis of Compound 181

Compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of compound IIC-1 used in Synthesis Example 20 and the same procedure as in Synthesis Example 20 was performed. 181 (2.68 g, yield: 51%) was obtained.

GC-Mass (Theoretical value: 1016.30 g / mol, Measured value: 1016 g / mol)

Example 1 Manufacture of Green Organic EL Device

Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, using Compound 1 of Synthesis Example 1 as a host, m-MTDATA (60 nm) / TCTA (80 nm) / Compound 1 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in order to produce an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used are as follows.

Examples 2 to 181 Fabrication of Green Organic EL Devices

An organic EL device was manufactured in the same manner as in Example 1, except that Compounds 2 to 181, which were synthesized in Synthesis Examples 2 to 181, were used instead of Compound 1 used as a host material in forming the emission layer in Example 1. It was.

Comparative Example Fabrication of Green Organic EL Device

An organic EL device was manufactured in the same manner as in Example 1, except that the following CBP was used instead of Compound 1 used as a host material in forming the emission layer in Example 1. The structure of CBP used is as follows.

Experimental Example 1

For the green organic EL devices prepared in Examples 1 to 181 and Comparative Example 1, the driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

Table 1

	Host	Driving voltage (V)	Current efficiency (cd / A)
Example 1	Compound 1	6.55	42.1
Example 2	Compound 2	6.45	42.2
Example 3	Compound 3	6.50	41.8
Example 4	Compound 4	6.50	41.5
Example 5	Compound 5	6.60	41.9
Example 6	Compound 6	6.55	41.9
Example 7	Compound 7	6.50	42.0
Example 8	Compound 8	6.45	41.9
Example 9	Compound 9	6.50	41.8
Example 10	Compound 10	6.55	41.7
Example 11	Compound 11	6.65	41.9
Example 12	Compound 12	6.50	42.1
Example 13	Compound 13	6.50	42.0
Example 14	Compound 14	6.55	41.7
Example 15	Compound 15	6.65	42.1
Example 16	Compound 16	6.45	41.5
Example 17	Compound 17	6.40	41.9
Example 18	Compound 18	6.55	42.0
Example 19	Compound 19	6.50	41.7
Example 20	Compound 20	6.55	41.6
Example 21	Compound 21	6.60	41.9
Example 22	Compound 22	6.60	42.2
Example 23	Compound 23	6.50	41.7
Example 24	Compound 24	6.55	41.5
Example 25	Compound 25	6.40	41.8
Example 26	Compound 26	6.35	41.7
Example 27	Compound 27	6.40	42.2
Example 28	Compound 28	6.35	41.6
Example 29	Compound 29	6.45	41.5
Example 30	Compound 30	6.50	41.7
Example 31	Compound 31	6.55	41.8
Example 32	Compound 32	6.50	42.2
Example 33	Compound 33	6.60	41.6
Example 34	Compound 34	6.40	41.5
Example 35	Compound 35	6.40	42.1
Example 36	Compound 36	6.60	41.0
Example 37	Compound 37	6.45	41.9
Example 38	Compound 38	6.55	41.7
Example 39	Compound 39	6.50	41.6
Example 40	Compound 40	6.55	41.3
Example 41	Compound 41	6.50	41.5
Example 42	Compound 42	6.60	42.0
Example 43	Compound 43	6.60	41.9
Example 44	Compound 44	6.40	41.8
Example 45	Compound 45	6.45	41.0
Example 46	Compound 46	6.65	41.3
Example 47	Compound 47	6.60	42.3
Example 48	Compound 48	6.45	41.9
Example 49	Compound 49	6.55	41.5
Example 50	Compound 50	6.50	41.9
Example 51	Compound 51	6.60	42.1
Example 52	Compound 52	6.55	41.5
Example 53	Compound 53	6.55	41.5
Example 54	Compound 54	6.50	41.8
Example 55	Compound 55	6.40	42.1
Example 56	Compound 56	6.35	41.8
Example 57	Compound 57	6.45	41.4
Example 58	Compound 58	6.55	41.5
Example 59	Compound 59	6.60	42.1
Example 60	Compound 60	6.50	41.8
Example 61	Compound 61	6.50	41.5
Example 62	Compound 62	6.40	41.5
Example 63	Compound 63	6.45	41.4
Example 64	Compound 64	6.50	41.8
Example 65	Compound 65	6.55	42.1
Example 66	Compound 66	6.55	41.7
Example 67	Compound 67	6.50	41.5
Example 68	Compound 68	6.40	41.9
Example 69	Compound 69	6.60	41.8
Example 70	Compound 70	6.50	41.3
Example 71	Compound 71	6.35	41.9
Example 72	Compound 72	6.40	42.1
Example 73	Compound 73	6.55	42.2
Example 74	Compound 74	6.55	41.7
Example 75	Compound 75	6.40	42.0
Example 76	Compound 76	6.50	41.5
Example 77	Compound 77	6.60	41.9
Example 78	Compound 78	6.55	42.0
Example 79	Compound 79	6.50	42.1
Example 80	Compound 80	6.55	41.6
Example 81	Compound 81	6.45	41.5
Example 82	Compound 82	6.60	42.2
Example 83	Compound 83	6.55	41.5
Example 84	Compound 84	6.50	41.8
Example 85	Compound 85	6.40	41.9
Example 86	Compound 86	6.45	41.7
Example 87	Compound 87	6.50	42.3
Example 88	Compound 88	6.40	41.6
Example 89	Compound 89	6.55	41.5
Example 90	Compound 90	6.50	42.3
Example 91	Compound 91	6.35	41.8
Example 92	Compound 92	6.50	42.1
Example 93	Compound 93	6.50	41.5
Example 94	Compound 94	6.51	41.5
Example 95	Compound 95	6.65	42.1
Example 96	Compound 96	6.55	42.1
Example 97	Compound 97	6.40	41.5
Example 98	Compound 98	6.55	41.7
Example 99	Compound 99	6.50	42.6
Example 100	Compound 100	6.55	41.3
Example 101	Compound 101	6.40	42.0
Example 102	Compound 102	6.45	41.2
Example 103	Compound 103	6.50	42.1
Example 104	Compound 104	6.50	41.9
Example 105	Compound 105	6.55	41.5
Example 106	Compound 106	6.40	42.3
Example 107	Compound 107	6.55	41.5
Example 108	Compound 108	6.45	42.4
Example 109	Compound 109	6.55	42.0
Example 110	Compound 110	6.35	41.3
Example 111	Compound 111	6.55	41.9
Example 112	Compound 112	6.50	42.1
Example 113	Compound 113	6.55	42.2
Example 114	Compound 114	6.50	41.9
Example 115	Compound 115	6.65	42.1
Example 116	Compound 116	6.60	41.5
Example 117	Compound 117	6.40	41.9
Example 118	Compound 118	6.55	42.0
Example 119	Compound 119	6.45	41.8
Example 120	Compound 120	6.40	41.6
Example 121	Compound 121	6.55	41.5
Example 122	Compound 122	6.40	42.2
Example 123	Compound 123	6.50	41.9
Example 124	Compound 124	6.55	41.8
Example 125	Compound 125	6.40	41.5
Example 126	Compound 126	6.45	41.7
Example 127	Compound 127	6.40	42.3
Example 128	Compound 128	6.50	41.6
Example 129	Compound 129	6.55	42.0
Example 130	Compound 130	6.50	41.5
Example 131	Compound 131	6.45	41.7
Example 132	Compound 132	6.30	42.0
Example 133	Compound 133	6.35	41.9
Example 134	Compound 134	6.40	41.5
Example 135	Compound 135	6.45	42.1
Example 136	Compound 136	6.40	41.5
Example 137	Compound 137	6.45	41.9
Example 138	Compound 138	6.55	41.8
Example 139	Compound 139	6.50	41.6
Example 140	Compound 140	6.50	41.6
Example 141	Compound 141	6.55	41.5
Example 142	Compound 142	6.50	42.0
Example 143	Compound 143	6.45	41.7
Example 144	Compound 144	6.40	40.8
Example 145	Compound 145	6.45	41.9
Example 146	Compound 146	6.60	41.6
Example 147	Compound 147	6.40	41.5
Example 148	Compound 148	6.55	41.9
Example 149	Compound 149	6.55	41.5
Example 150	Compound 150	6.50	41.7
Example 151	Compound 151	6.40	42.1
Example 152	Compound 152	6.45	41.5
Example 153	Compound 153	6.55	41.2
Example 154	Compound 154	6.50	41.7
Example 155	Compound 155	6.35	42.0
Example 156	Compound 156	6.40	41.8
Example 157	Compound 157	6.30	41.4
Example 158	Compound 158	6.35	41.7
Example 159	Compound 159	6.45	42.3
Example 160	Compound 160	6.55	41.3
Example 161	Compound 161	6.50	41.2
Example 162	Compound 162	6.50	41.5
Example 163	Compound 163	6.45	41.4
Example 164	Compound 164	6.50	41.8
Example 165	Compound 165	6.55	42.7
Example 166	Compound 166	6.40	41.3
Example 167	Compound 167	6.55	41.5
Example 168	Compound 168	6.45	41.0
Example 169	Compound 169	6.55	41.8
Example 170	Compound 170	6.40	41.3
Example 171	Compound 171	6.40	41.8
Example 172	Compound 172	6.55	42.1
Example 173	Compound 173	6.45	42.2
Example 174	Compound 174	6.50	41.7
Example 175	Compound 175	6.35	42.1
Example 176	Compound 176	6.40	41.6
Example 177	Compound 177	6.45	41.8
Example 178	Compound 178	6.50	42.1
Example 179	Compound 179	6.55	41.9
Example 180	Compound 180	6.50	41.5
Example 181	Compound 181	6.45	41.5
Comparative example	CBP	6.93	38.2

Referring to Table 1, a green organic EL device (Examples 1 to 65) using a compound represented by Formula 1 (Compounds 1 to 181) according to the present invention as a host material of a light emitting layer is green using a conventional CBP as a host material. It was confirmed that the organic EL device (Comparative Example 1) exhibited better performance in terms of current efficiency and driving voltage.

Claims (7)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   (In Formula 1,

   R ₃ to R ₆ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl phosphine group, Substituted or unsubstituted C _{6 Through} C ₄₀ An arylphosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring,

   Provided that at least one of R ₃ and R _4, R ₄ and R _5, and R ₅ and R ₆ may be bonded to each other to form a condensed ring represented by Formula 2 below;

   [Formula 2]

   

   In Chemical Formula 2,

   The dotted line is a site where condensation occurs with the compound of Formula 1;

   R ₁ , R ₂ , and R ₇ to R ₁₀ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C Alkenyl group of ₂ to C ₄₀ , substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted A C ₆ to C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group may be selected, or may be combined with an adjacent group to form a condensed ring;

   n is an integer from 0 to 4, and if n is an integer from 1 to 4, at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C Alkenyl group of ₂ to C ₄₀ , substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or An unsubstituted C ₆ -C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

   X ₁ and X ₂ are each independently selected from O, S, Se, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ ) and ;

   Ar ₁ to Ar ₃ are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group , Substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and Substituted or unsubstituted C ₆ ~ C _{40 It} is selected from the group consisting of arylsilyl group;

   In R ₁ to R _10, Ra, and Ar ₁ to Ar ₃ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl jade C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ of is selected from the group consisting arylsilyl One or more substituents, which may be the same or different from each other when there are a plurality of substituents).
2. The method of claim 1,

   Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of compounds represented by the following formula (3 to 8):

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   (In Chemical Formulas 3 to 8,

   R ₁ to R ₁₀ , Ra, X ₁ and X ₂ , Ar ₁ to Ar ₃ and n are as defined in claim 1 respectively).
3. The method of claim 1,

   X ₁ and X ₂ are both N (Ar ₁ ),

   Ar ₁ is a compound, characterized in that as defined in claim ₁ .
4. The method of claim 1,

   Ar ₁ to Ar ₃ are the same as or different from each other, each independently represent a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,

   In Ar ₁ to Ar ₃ , the aryl group and heteroaryl group are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 ~ 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ An aryl phosphine group, C ₆ ~ C ₄₀ An aryl phosphine oxide group and C ₆ ~ C ₄₀ It may be substituted with one or more substituents selected from the group consisting of, wherein a plurality of substituents If characterized in that they can be the same or different from one another.
5. The method of claim 1,

   Ar ₁ to Ar ₃ are the same or different from each other, and each independently a compound characterized in that it is selected from the group consisting of the structures represented by the following substituents S1 to S206:

   

   

   

   

   

   
6. In an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode,

   At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 5.
7. The method of claim 6,

   At least one of the one or more organic material layer containing the compound is an organic electroluminescent device, characterized in that the light emitting layer.