KR101571598B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device including the organic electroluminescent device. The organic electroluminescent device using the organic compound as a host material is introduced into an organic electroluminescent device to improve the organic electroluminescent Device can be provided.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

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

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity of Bernanose in the 1950s . In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to make a high efficiency and high number of organic EL devices, each organic EL device has been developed in a manner of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can 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. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered due to their low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

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

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

R ₃ to R ₆ are the same or different from each other and each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted 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 heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted A C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkylcarbonyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ ring An aryl phosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to 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 is bonded to each other to form a condensed ring represented by the following formula (2);

In Formula 2,

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

R ₁ , R ₂ and R ₇ to R ₁₀ are the same or different and each independently represents 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 A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, hwandoen C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted 3 to 40 nuclear atoms of a heterocycloalkyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or non-substituted of unsubstituted C ₁ ~ C ₄₀ alkyl boron group, an aryl phosphonic a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ of pingi, substituted or unsubstituted 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 may combine with adjacent groups to form a condensed ring;

n is an integer of 0 to 4, provided that when n is an integer of 1 to 4, at least one Ra is independently selected from the group consisting of 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 A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, hwandoen C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted 3 to 40 nuclear atoms of a heterocycloalkyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or non-substituted of unsubstituted C 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 aryl phosphine group, a substituted or An unsubstituted C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to 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 ) ;

Ar ₁ to Ar ₃ are the same or different, each independently represent a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted of C ₂ ~ C ₄₀ unsubstituted C ₂ ~ of aryl of C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted in the ring C ₆ ~ C ₄₀ of the oxy group , A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a 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 C ₆ ~ C ₄₀ aryl phosphine oxide group, and A substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group;

In R ₁ to R _10, Ra and Ar ₁ to Ar ₃ , 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 alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ of alkyloxy An arylamine group of C ₆ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nucleus atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to 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 May be substituted with one or more substituents, and when the substituents are plural, they may be the same or different from each other.

Also, the present invention is an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes the compound An organic electroluminescent device is provided.

At least one of the one or more organic layers including the compound is preferably a light emitting layer.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 according to the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life time, A full-color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

The novel compound according to the present invention has a structure in which an indole moiety is fused at the terminal of an indenoindole moiety to form a basic skeleton and various substituents are bonded to the basic skeleton. .

The compound represented by Formula 1 has a structure in which a large indole moiety is bonded to an end of an indenoindole moiety and an electron donor has a wide band gap, (Bipolar) property of the whole molecule due to various aromatic ring substituents having an electron withdrawing property, thereby enhancing the bonding force between holes and electrons. Therefore, when the above compound is applied to the organic EL device, the phosphorescent property of the device can be improved and the hole injecting ability and / or transporting ability, luminous efficiency, The driving voltage, the life characteristic, and the like can be improved. Further, the energy level can be controlled according to the substituent, so that it has a wide band gap (sky blue to red), and thus can be applied not only to a light emitting layer but also to a hole transporting layer and a hole injecting layer.

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

Further, since the molecular weight of the compound is significantly increased due to various aromatic ring substituents introduced in many of the bonded indole moieties, the glass transition temperature can be improved, and the conventional CBP (4,4 -dicarbazolybiphenyl). < / RTI > In addition, the indole moiety bonded to the end of the indenoindole moiety is fused to improve the thermal stability of the compound, and the crystallization of the organic compound layer including the compound of the formula (1) Which is effective in suppressing the disease. Therefore, the organic EL device including the compound of Formula 1 according to the present invention can greatly improve durability and lifetime characteristics.

In addition, when the compound represented by Formula 1 according to the present invention is used as a hole injecting / transporting layer material for an organic EL device, a blue, green, and / or red phosphorescent host material, Effect can be exerted. Therefore, the compound represented by the general formula (1) of the present invention can greatly contribute to improvement of the performance and lifetime of the organic EL device, and particularly the lifetime of the organic EL device is greatly improved in maximizing the performance in the full-color organic luminescent panel.

In the compound represented by Formula 1, R ₃ to R ₆ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, of a C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 of the A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, Or an unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus 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 .

In the above R ₃ to R ₆ , 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, A halogen atom, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ alkoxy group, A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to 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 selected from the group consisting of hydrogen, or substituents S1 to S206 shown below, but are not limited thereto.

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

In the formula (2), the dotted line indicates a site where condensation is performed with at least one of R ₃ and R _4, R ₄ and R _5, and R ₅ and R ₆ in the formula (1).

Wherein R ₁ , R ₂ and R ₇ to R ₁₀ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, 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 heteroaryl group having 5 to 40 nuclear atoms aryl group, a substituted or unsubstituted C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ of the alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a 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 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 aryl phosphine group, a substituted or An unsubstituted C ₆ to C ₄₀ aryl phosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring.

In this case, the R _1, R _2, and R ₇ to an alkyl group in R _10, 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, The alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphinoxide group and the arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkene A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , A C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron 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 The substituent may be the same or different from each other when the substituent is plural.

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

And n is an integer of 0 to 4. When n is 0, it means that hydrogen is not substituted with substituent Ra. Further, if the n is an integer from 1 to 4, as the hydrogen is substituted with a substituent Ra, one or more Ra are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or An unsubstituted 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 C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group , A substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ of the alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ Ah 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 may be bonded to an adjacent group to form a condensed ring .

The Ra in Ra may be an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron 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 When the substituents are plural, they may be the same or different.

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

The way the compound represented by Formula 1, X ₁ and X ₂ is selected from each independently 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 all be N (Ar ₁ ).

Wherein Ar ₁ to Ar ₃ are the same or different, each independently represent 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 of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ alkylsulfonyl group, 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 A substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms.

In the above 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, the arylboronic group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 or different from each other and each independently selected from the group consisting of the substituents S1 to S206, but are not limited thereto.

Examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formulas (3) to (8), but are not limited thereto.

In the above 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 Formula 1, respectively.

In the present invention, "alkyl" is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, , Hexyl, and the like.

The "alkenyl" in the present invention is a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, 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 and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2-propynyl, and the like.

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl 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. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. It is also understood that two or more rings may be pendant or fused to each other and further include a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2- isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

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

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may have a linear, branched or cyclic structure . 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 cycloalkyls 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, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. ≪ / RTI > Examples of such heterocycloalkyl include morpholine, piperazine and the like.

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

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compounds of formula (I) 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 . 2457 (1995)). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

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

More particularly, the present invention relates to an organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the organic material layers A compound represented by the formula (1), preferably a compound represented by the formula (3) to (8). At this time, the compounds may be used singly or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1. [ At this time, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device of the present invention may include a host material, which may include the compound of Formula 1 as a host material. When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . Specifically, the compound represented by the general formula (1) of the present invention can be used as a phosphorescent host material in the light emitting layer. In some cases, an electron injecting layer may be further stacked on the electron transporting 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 layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one of the organic material layers (for example, the light emitting layer) An organic material 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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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 multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound IIC-1 & IIC-2

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

After adding (4-bromophenyl) hydrazine hydrochloride (223.5 g, 1.0 mol) into the reactor, acetic acid (1,000 ml) was added and stirred. 3,3-dimethyl-2,3-dihydro-1H-inden-1-one (160.2 g, 1.0 mol) was added dropwise to the reactor, 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, the water was removed from the organic layer using 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%).

¹ H-NMR:? 1.82 (s, 6H), 7.34 (m, 3H), 7.57

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

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

After the reaction was completed, the organic layer was extracted with ethyl acetate, the organic layer was washed with MgSO ₄ to remove water, and then purified by column chromatography (Hexane: EA = 10: 1 (v / v) -8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2- b] indole (22.35 g, .

^{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) and 10,10-dimethyl-8- (4,4,5,5-tetramethyl- 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 / , Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, and the mixture was stirred at 80 DEG C for 12 hours.

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

¹ H-NMR:? 1.71 (s, 6H) 7.37 (m, 3H), 7.73 (m, 4H)

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

Dimethyl-8- (2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol) obtained in the above Step 3, iodobenzene (20.46 g, 100 ml), 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 the reaction was terminated, the nitrobenzene was removed, and 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 purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 10,10-dimethyl-8- (2-nitrophenyl) -5-phenyl-5,10-dihydroindeno - [1,2-b] indole (20.1 g, yield: 70%).

^{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

(2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole (20.10 g, 46.7 mmol) obtained in the above Step 4 and a triphenylphosphine (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, and the organic layer was extracted with dichloromethane, and the organic layer was filtered with MgSO ₄ . Compound IIC-1 (11.2 g, yield: 60%) and compound IIC-2 (3.7 g, yield: 60%) were obtained by removing the solvent from the obtained organic layer and then purifying by column chromatography (Hexane: MC = 2: Yield: 19.80%).

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

Compound IIC-2 ¹ H-NMR of: 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 [ ] Synthesis of indole

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

After the reaction was completed, the solvent was concentrated under reduced pressure, and the organic layer was extracted with ethyl acetate. 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%).

Compound A ¹ H-NMR of: 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)

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

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

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

After the reaction was completed, the organic layer was extracted with ethyl acetate, the water was removed from the organic layer with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v) - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2- b] indole (22.35 g, yield 76%).

¹ H-NMR:? 1.21 (s, 12H) 1.70 (s, 6H), 7.30 (m, 4H)

<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) and 10,10-dimethyl-9- (4,4,5,5-tetramethyl- 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 / , Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, and the mixture was stirred at 80 DEG C for 12 hours.

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

^{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

(2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol) obtained in the above Step 3, iodobenzene (20.46 g, 100 ml), 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, and the organic layer was extracted with methylene chloride. Then, 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%).

^{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

(2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole (20.10 g, 46.7 mmol) obtained in Step 4, triphenylphosphine (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, and the organic layer was extracted with dichloromethane. Then, 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 obtain compound IIC-3 (11.2 g, yield: 60%).

¹ H-NMR of Compound IIC-3:? 1.71 (s, 6H) 7.34 (m, 3H), 7.43 (m, 7H), 7.52 (m, 4H), 8.08 )

[Preparation Example 3] Synthesis of compounds IIC-4 and IIC-5

<Step 1>

Bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole and 7-bromo-10,10-dimethyl- 10-dihydroindeno [1,2-b] indole.

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

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

After the reaction was completed, 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 = 10: 1 (v / v) - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2- b] indole (22.35 g, yield 76%).

¹ H-NMR:? 1.21 (s, 12H) 1.70 (s, 6H), 7.34 (m, 4H)

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) and 10,10-dimethyl-7- (4,4,5,5-tetramethyl- 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 / Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, followed by stirring at 80 DEG C for 12 hours.

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

¹ H-NMR:? 1.71 (s, 6H) 7.37 (m, 3H), 7.62 (m, 4H), 7.73 (m, 2H), 7.85 , 1H)

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

(2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol) obtained in Step 3, iodobenzene (20.46 g, 100 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, and the organic layer was extracted with methylene chloride. Then, MgSO ₄ was added and the organic layer was filtered. The solvent was removed from the obtained organic layer and the residue was 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%).

^{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

(2-nitrophenyl) -5-phenyl-5,10-dihydroindeno- [1,2-b] indole (20.10 g, 46.7 mmol) obtained in the above Step 4 and a triphenylphosphine (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 and the organic layer was extracted with dichloromethane. Then, MgSO ₄ was added and the organic layer was filtered. Compound IIC-4 (11.2 g, yield: 60%) and compound IIC-5 (3.7 g, yield: 60%) were obtained by removing the solvent from the obtained organic layer and then purifying by column chromatography (Hexane: MC = 2: Yield: 19.80%).

Compound IIC-4 ¹ H-NMR of: 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, 1 H)

Compound IIC-5 ¹ H-NMR of: 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, 1 H)

[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, 1.0 mol) was added to the reactor, acetic acid (1,000 ml) was added, and the mixture was stirred. Then, 3,3-dimethyl-2,3-dihydro-1H-inden-1-one (160.2 g, 1.0 mol) was added dropwise to the reactor, and the mixture was stirred 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, the water was removed from the organic layer using MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 4: 1 (v / bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole (190 g, yield: 61%).

^{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 Preparation of 10,10-dimethyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10- dihydroindeno [ synthesis

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

After the reaction was completed, the organic layer was extracted with ethyl acetate, the organic layer was washed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v) - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2- b] indole (22.35 g, yield 76%).

^{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) and 10,10-dimethyl-6- (4,4,5,5-tetramethyl- dioxaborolan-2-yl) -5,10- dihydroindeno [1,2-b] the indole (35.9 g, 100 mmol) , NaOH (11.9 g, 300 mmol) and _{THF / H 2 O (200 ml} / 50 ml) After mixing, Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added and stirred at 80 DEG C for 12 hours.

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

^{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

(2-nitrophenyl) -5,10-dihydroindeno [1,2-b] indole (23.7 g, 66.9 mmol) obtained in Step 3, iodobenzene (20.46 g, 100 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, and the organic layer was extracted with methylene chloride. Then, 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%).

^{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

(2-nitrophenyl) -5-phenyl-5,10-dihydroindeno [1,2-b] indole (20.10 g, 46.7 mmol) obtained in the above Step 4 and a triphenylphosphine 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 and the organic layer was extracted with dichloromethane. Then, 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 obtain compound IIC-6 (11.2 g, yield: 60%).

¹ H-NMR of Compound IIC-6:? 1.71 (s, 6H), 7.35 (m, 3H), 7.47 (m, 7H), 7.55 1H)

[Preparation Example 5] Synthesis of Compound IIC7

<Steps 1 and 2>

10-dimethyl-5,10-dihydroindeno [1,2-b] indole and 10,10-dimethyl indole were obtained in the same manner as in <Step 1> and <Step 2> (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole.

<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) and 10,10-dimethyl- 6- (4,4,5,5-tetramethyl- 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) were mixed, and then Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, followed by stirring at 80 DEG C for 12 hours.

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

^{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

10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) obtained in the above Step 3, 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, and the organic layer was extracted with methylene chloride. Then, 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 6- (5-chloro-2-nitrophenyl) , 10-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%).

^{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, 1 H)

<Step 5> Synthesis of Compound IIC-7

(5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g, 46.7 mmol ), Triphenylphosphine (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 and the organic layer was extracted with dichloromethane. Then, 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 obtain compound IIC-7 (12.2 g, yield: 60%).

Compound IIC-7 ¹ H-NMR of: 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, 1 H)

[Preparation Example 6] Synthesis of compounds IIC-8 and IIC-9

<Steps 1 and 2>

Bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole and 7-bromo-10,10-dimethyl- 10-dihydroindeno [1,2-b] indole was obtained in the same manner as in Step 2 and 10,10-dimethyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl) -5,10-dihydroindeno [1,2-b] indole.

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) and 10,10-dimethyl-7- (4,4,5,5-tetramethyl- 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) were mixed, and then Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, followed by stirring at 80 DEG C for 12 hours.

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

^{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

10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) obtained in the above Step 3, 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, and the organic layer was extracted with methylene chloride. Then, MgSO ₄ was added and the organic layer was filtered. After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain 7- (5-chloro-2-nitrophenyl) , 10-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%).

^{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, 1 H)

<Step 5> Synthesis of compounds IIC-8 and IIC-9

(5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g, 46.7 mmol ), Triphenylphosphine (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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-8 (11.2 g, yield 60%) and compound IIC- : 19.80%).

Compound IIC-8 ¹ H-NMR of: 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, 1 H)

Compound IIC-9 ¹ H-NMR of: 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, 1 H)

[Preparation Example 7] Synthesis of compounds IIC-10 and IIC-11

<Steps 1 and 2>

Bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole and 10,10-dimethyl indole were carried out in the same manner as in <Step 1> and <Step 2> -8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole.

Step 3 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) and 10,10-dimethyl-8- (4,4,5,5-tetramethyl- 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) were mixed, and then Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, followed by stirring at 80 DEG C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, and the organic layer was filtered with MgSO ₄ . 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- [1,2-b] indole (26.0 g, yield: 67%).

^{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

10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) obtained in the above Step 3, 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, and the organic layer was extracted with methylene chloride. Then, 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-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%).

^{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

2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g, 46.7 mmol), triphenylphosphine (36.7 g, 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 and the organic layer was extracted with dichloromethane. Then, 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 obtain compound IIC-10 (11.2 g, yield: 60% Yield: 19.80%).

Compound IIC-10 ¹ H-NMR of: 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, 1 H)

Compound IIC-11 ¹ H-NMR of: 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), &lt; / RTI &gt; 11.30 (b, 1H)

[Preparation Example 8] Synthesis of Compound IIC-12

<Steps 1 and 2>

Bromo-10,10-dimethyl-5,10-dihydroindeno [1,2-b] indole and 10,10-dimethyl indole were carried out in the same manner as in <Step 1> and <Step 2> -8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,10-dihydroindeno [1,2-b] indole.

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) and 10,10-dimethyl-9- (4,4,5,5-tetramethyl- 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) were mixed, and then Pd (PPh3) ₄ (3.3 g, ₃ mmol) was added thereto, followed by stirring at 80 DEG C for 12 hours.

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

^{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

10-dimethyl-5,10-dihydroindeno [1,2-b] indole (26.0 g, 66.9 mmol) obtained in the above Step 3, 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, and the organic layer was extracted with methylene chloride. Then, 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-dihydroindeno [1,2-b] indole (21.8 g, yield: 70%).

^{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

(5-chloro-2-nitrophenyl) -10,10-dimethyl-5-phenyl-5,10-dihydroindeno [1,2-b] indole (21.8 g, 46.7 mmol ), triphenylphosphine (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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the resulting organic layer and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain compound IIC-12 (12.2 g, yield: 60%).

Compound IIC-12 ¹ H-NMR of: 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, 1 H)

[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) synthesized in Preparation Example 5 and THF / H ₂ O (80 mL / 20 mL) a put and mixed, and _{then, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-7-1 (4.45 g, 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 a nitrogen stream. pyridine-2-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL), Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) And the mixture was stirred at 80 ° C for 12 hours.

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

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

Compound IIC-7 (5.2 g, 12.0 mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (4.88g, 13.2mmol) , NaOH (1.44g, 36.0mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , and then, Pd (PPh ₃₎ into a ₄ (693mg, 0.600mmol) Followed by stirring at 80 DEG C for 12 hours.

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

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

(5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol) synthesized in Preparation Example 5, NaOH (1.44 g, 36.0 mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , insert the _{next, Pd (PPh 3) 4 (} 693mg, 0.600mmol), and the mixture was stirred at 80 ℃ for 12 hours.

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

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

(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) mixed into a _{following, Pd (PPh 3) 4 (} 693mg, 0.600mmol), and the mixture was stirred at 80 ℃ for 12 hours.

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

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

(5.2 g, 12.0 mmol), pyridin-3-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 6 and THF / H ₂ O 80 mL / 20 mL) were mixed, and then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) 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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-8-2 (3.54 g, yield: 62%).

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

Compound IIC-8 (5.2 g, 12.0 mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (4.88g, 13.2mmol) , NaOH (1.44g, 36.0mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , and then, Pd (PPh ₃₎ into a ₄ (693mg, 0.600mmol) Followed by stirring at 80 DEG C for 12 hours.

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

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

(5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol) synthesized in Preparation Example 6, NaOH (1.44 g, 36.0 mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , insert the _{next, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

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

Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) were added to a solution of compound IIC-9 (5.2 g, 12.0 mmol) a put and mixed, and _{then, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

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

(5.2 g, 12.0 mmol), pyridin-2-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 6 and THF / H ₂ O 80 mL / 20 mL) were mixed, and then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) 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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-9-2 (3.54 g, yield: 62%).

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

Compound IIC-9 (5.2 g, 12.0 mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (4.88g, 13.2mmol) , NaOH (1.44g, 36.0mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , and then, Pd (PPh ₃₎ into a ₄ (693mg, 0.600mmol) Followed by stirring at 80 DEG C for 12 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer, and the residue was 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

(5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol) synthesized in Preparation Example 6, NaOH (1.44 g, 36.0 mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , insert the _{next, Pd (PPh 3) 4 (} 693mg, 0.600mmol), and the mixture was stirred at 80 ℃ for 12 hours.

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

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

Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) were added to a solution of compound IIC-10 (5.2 g, 12.0 mmol) a put and mixed, and _{then, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

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

(5.2 g, 12.0 mmol), pyridin-3-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 7 and THF / H ₂ O 80 mL / 20 mL) were mixed, and then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) 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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-10-2 (3.54 g, yield: 62%).

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

Compound IIC-10 (5.2 g, 12.0 mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (4.88g, 13.2mmol) , NaOH (1.44g, 36.0mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , and then, Pd (PPh ₃₎ into a ₄ (693mg, 0.600mmol) Followed by stirring at 80 DEG C for 12 hours.

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

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

(5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol) synthesized in Preparation Example 7, NaOH (1.44 g, 36.0 mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , insert the _{next, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

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

Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) were added to a solution of compound IIC-11 (5.2 g, 12.0 mmol) a put and mixed, and _{then, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

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

(5.2 g, 12.0 mmol), pyridin-2-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 7 and THF / H ₂ O 80 mL / 20 mL) were mixed, and then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) 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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-11-2 (3.54 g, yield: 62%).

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

Compound IIC-11 (5.2 g, 12.0 mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (4.88g, 13.2mmol) , NaOH (1.44g, 36.0mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , and then, Pd (PPh ₃₎ into a ₄ (693mg, 0.600mmol) Followed by stirring at 80 DEG C for 12 hours.

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

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

(5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol) synthesized in Preparation Example 7, NaOH (1.44 g, 36.0 mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , insert the _{next, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

[Preparation Example 14-1] Synthesis of Compound IIC-12-1

Phenylboronic acid (1.61 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) and THF / H ₂ O (80 mL / 20 mL) were added to a solution of compound IIC-12 (5.2 g, 12.0 mmol) a put and mixed, and _{then, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

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

(5.2 g, 12.0 mmol), pyridin-3-ylboronic acid (1.62 g, 13.2 mmol), NaOH (1.44 g, 36.0 mmol) synthesized in Preparation Example 8 and THF / H ₂ O 80 mL / 20 mL) were mixed, and then Pd (PPh ₃ ) ₄ (693 mg, 0.600 mmol) 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, and the organic layer was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 20: 1 (v / v)) to obtain compound IIC-12-2 (3.54 g, yield: 62%).

[Preparation Example 14-3] Synthesis of Compound IIC-12-3

Compound IIC-12 (5.2 g, 12.0 mmol), 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (4.88g, 13.2mmol) , NaOH (1.44g, 36.0mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , and then, Pd (PPh ₃₎ into a ₄ (693mg, 0.600mmol) Followed by stirring at 80 DEG C for 12 hours.

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

[Preparation Example 14-4] Synthesis of Compound IIC-12-4

(5.2 g, 12.0 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (3.01 g, 13.2 mmol) synthesized in Preparation Example 8, NaOH (1.44 g, 36.0 mmol) and a mixture of _{THF / H 2 O (80mL /} 20mL) , insert the _{next, Pd (PPh 3) 4 (} 693mg, 0.600mmol) was stirred at 80 ℃ for 12 hours.

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

[Synthesis Example 1] Synthesis of Compound 1

(5.0 g, 12.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.8 mmol) synthesized in Preparation Example 1 and NaH , 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 (calculated: 629.26 g / mol, measured: 629 g / mol)

[Synthesis Example 2] Synthesis of Compound 2

(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, It was mixed with 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) and stirred at 190 ℃ for 12 hours .

After the reaction was completed, the 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, the residue was purified by column chromatography to obtain Compound 2 (3.2 g, yield: 61%).

GC-Mass (calculated: 705.29 g / mol, measured: 705 g / mol)

[Synthesis Example 3] Synthesis of Compound 3

Compound IIC-1 (3.0 g, 7.5 mmol) and 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine synthesized in Preparation Example 1 , 11.3 mmol), Pd (OAc ) 2 (0.17 g, 0.75mmol), 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, followed by stirring at 110 ° C for 12 hours.

After the reaction was completed, 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 obtain Compound 3 : 64%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 4] Synthesis of Compound 4

(3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 2- (4'- (3.59 g, yield: 61%) was obtained by following the same procedure as in Synthesis Example 3, except that diphenyl-1,3,5-triazine (4.75 g, 11.3 mmol) was used.

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 5] Synthesis of Compound 5

Except that 2-bromo-4,6-diphenylpyridine (3.506 g, 11.3 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Was subjected to the same procedure as in Synthesis Example 2 to obtain Compound 5 (2.3 g, yield: 48%).

GC-Mass (calculated: 627.27 g / mol, measured: 627 g / mol)

[Synthesis Example 6] Synthesis of Compound 6

Except that 2- (3-chlorophenyl) -4,6-diphenylpyridine (3.86 g, 0.15 mol) was used instead of 2- (4'- chlorobiphenyl- 11.3 mmol), the same procedure as in Synthesis Example 3 was conducted to obtain Compound 6 (2.3 g, yield: 44%).

GC-Mass (calculated: 703.30 g / mol, measured: 703 g / mol)

[Synthesis Example 7] Synthesis of Compound 7

Except that 2-bromo-4,6-diphenylpyrimidine (3.51 g, 11.3 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 Was subjected to the same procedure as in Synthesis Example 2 to obtain Compound 7 (3.1 g, yield: 66%).

GC-Mass (calculated: 628.26 g / mol, measured: 6282 g / mol)

[Synthesis Example 8] Synthesis of Compound 8

Instead of 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (3.87 g, 0.15 mmol) instead of 2- (4'- chlorobiphenyl- 11.3 mmol), the same procedure as in Synthesis Example 3 was conducted to obtain Compound 8 (2.65 g, yield: 50%).

GC-Mass (calculated: 704.29 g / mol, measured: 704 g / mol)

[Synthesis Example 9] Synthesis of Compound 9

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

GC-Mass (calculated: 552.23 g / mol, measured: 552 g / mol)

[Synthesis Example 10] Synthesis of Compound 10

Except that 2-bromo-5-phenylpyridine (2.64 g, 11.3 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, The same procedure as in Synthesis Example 2 was conducted to obtain Compound 10 (2.03 g, yield: 49%).

GC-Mass (calculated: 551.24 g / mol, measured: 551 g / mol)

[Synthesis Example 11] Synthesis of Compound 11

Except that 2- (3-bromophenyl) pyridine (2.64 g, 11.3 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2 , And the same procedure as in Synthesis Example 2 was carried out to obtain Compound 11 (2.36 g, yield: 57%).

GC-Mass (calculated: 551.24 g / mol, measured: 551 g / mol)

[Synthesis Example 12] Synthesis of Compound 12

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 , The compound 12 (3.37 g, yield: 70%) was obtained in the same manner as in Synthesis Example 2.

GC-Mass (theory: 639.27 g / mo; measured: 639 g / mol)

[Synthesis Example 13] Synthesis of Compound 13

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 2, 2- (4-bromophenyl) , 11.30 mmol), the same procedure as in Synthesis Example 2 was conducted to obtain Compound 13 (3.36 g, yield: 67%).

GC-Mass (calculated: 666.28 g / mol, measured: 666 g / mol)

[Synthesis Example 14] Synthesis of Compound 14

4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazine was used in place of 2- (3-bromophenyl) (3.13 g, yield: 60%) was obtained in the same manner as in Synthesis Example 2, except that triazole (4.25 g, 11.30 mmol) was used.

GC-Mass (calculated: 693.29 g / mol, measured: 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- The procedure of Synthesis Example 3 was repeated to obtain Compound 15 (2.49 g, yield: 55%).

GC-Mass (theory: 602.25 g / mol, measurement: 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 ), The procedure of Synthesis Example 3 was repeated to obtain Compound 16 (3.07 g, yield: 60%).

GC-Mass (theory: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 17] Synthesis of Compound 17

Except that 4- (biphenyl-4-yl) -2-chloroquinazoline (3.57 g, 0.35 mmol) was used instead of 2- (4'- chlorobiphenyl- 11.30 mmol), the procedure of Synthesis Example 3 was repeated to obtain Compound 17 (2.24 g, yield: 44%).

GC-Mass (theory: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 18] Synthesis of Compound 18

Except that 4-bromo-N, N-diphenylaniline (3.66 g, 11.3 mmol) was used in place of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- (2.61 g, yield: 54%) was obtained by carrying out the same processes as in Synthesis Example 2.

GC-Mass (calculated: 641.28 g / mol, measured: 641 g / mol)

[Synthesis Example 19] Synthesis of Compound 19

(Biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine instead of 2- (3-bromophenyl) (3.71 g, yield: 62%) was obtained by following the same procedure as in Synthesis Example 2, except that the title compound (5.38 g, 11.30 mmol) was used.

GC-Mass (calculated: 793.35 g / mol, measured: 793 g / mol)

[Synthesis Example 20] Synthesis of Compound 20

(Biphenyl-4-yl) -N- (4-bromophenyl) -9,9-diol was used in place of 2- (3-bromophenyl) Compound 20 (4.39 g, yield: 70%) was obtained by following the same procedure as in Synthesis Example 2, except that dimethyl-9H-fluoren-2-amine (5.84 g, 11.3 mmol) was used.

GC-Mass (calculated: 833.38 g / mol, measured: 833 g / mol)

[Synthesis Example 21] Synthesis of Compound 21

The procedure of Synthesis Example 1 was repeated, except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 1 to obtain 3.13 g , Yield: 66%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 22] Synthesis of Compound 22

The procedure of Synthesis Example 2 was repeated except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 2 to obtain 3.14 g , Yield: 59%).

GC-Mass (calculated: 705.29 g / mol, measured: 705 g / mol)

[Synthesis Example 23] Synthesis of Compound 23

The procedure of Synthesis Example 3 was repeated, except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 3 to obtain 3.47 g , Yield: 59%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 24] Synthesis of Compound 24

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

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 25] Synthesis of Compound 25

The procedure of Synthesis Example 11 was repeated except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 11 to obtain 2.12 g , Yield: 51%).

GC-Mass (calculated: 551.24 g / mol, measured: 551 g / mol)

[Synthesis Example 26] Synthesis of Compound 26

The procedure of Synthesis Example 12 was repeated except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 12 to obtain 2.65 g , Yield: 55%).

GC-Mass (calculated: 639.27 g / mol, measured: 639 g / mol)

[Synthesis Example 27] Synthesis of Compound 27

The same procedure as in Synthesis Example 15 was carried out, except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 15 to obtain 2.81 g , Yield: 62%).

GC-Mass (theory: 602.25 g / mol, measurement: 602 g / mol)

[Synthesis Example 28] Synthesis of Compound 28

The procedure of Synthesis Example 16 was repeated except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 16 to give 3.06 g , Yield: 60%).

GC-Mass (theory: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 29] Synthesis of Compound 29

The procedure of Synthesis Example 17 was repeated, except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 17 to obtain 3.83 g , Yield: 75%).

GC-Mass (calculated: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 30] Synthesis of Compound 30

The same procedure as in Synthesis Example 19 was carried out, except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 19 to give 3.59 g , Yield: 60%).

GC-Mass (calculated: 793.35 g / mol, measured: 793 g / mol)

[Synthesis Example 31] Synthesis of Compound 31

The procedure of Synthesis Example 20 was repeated except that the compound IIC-2 (3.0 g, 7.5 mmol) synthesized in Preparation Example 1 was used instead of the compound IIC-1 used in Synthesis Example 20 to obtain 3.31 g , Yield: 63%).

GC-Mass (calculated: 833.38 g / mol, measured: 833 g / mol)

[Synthesis Example 32] Synthesis of Compound 32

The procedure of Synthesis Example 1 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 1 to obtain 3.32 g , Yield: 70%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 33] Synthesis of Compound 33

The procedure of Synthesis Example 2 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 2 to obtain 3.33 g , Yield: 64%).

GC-Mass (calculated: 705.29 g / mol, measured: 705 g / mol)

[Synthesis Example 34] Synthesis of Compound 34

The same procedure as in Synthesis Example 3 was carried out, except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 3 to give 3.59 g , Yield: 61%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 35] Synthesis of Compound 35

The procedure of Synthesis Example 4 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 4 to obtain 3.35 g , Yield: 59%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 36] Synthesis of Compound 36

The procedure of Synthesis Example 11 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 11 to obtain Compound 36 (1.61 g , Yield: 39%).

GC-Mass (calculated: 551.24 g / mol, measured: 551 g / mol)

[Synthesis Example 37] Synthesis of Compound 37

The procedure of Synthesis Example 12 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 12 to obtain 2.65 g , Yield: 55%).

GC-Mass (calculated: 639.27 g / mol, measured: 639 g / mol)

[Synthesis Example 38] Synthesis of Compound 38

The procedure of Synthesis Example 15 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 15 to obtain 2.81 g , Yield: 62%).

GC-Mass (theory: 602.25 g / mol, measurement: 602 g / mol)

[Synthesis Example 39] Synthesis of Compound 39

The procedure of Synthesis Example 16 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 16 to obtain Compound 39 (2.55 g , Yield: 50%).

GC-Mass (theory: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 40] Synthesis of Compound 40

The procedure of Synthesis Example 17 was repeated, except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 17 to obtain 3.21 g , Yield: 63%).

GC-Mass (calculated: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 41] Synthesis of Compound 41

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

GC-Mass (calculated: 793.35 g / mol, measured: 793 g / mol)

[Synthesis Example 42] Synthesis of Compound 42

The procedure of Synthesis Example 20 was repeated except that the compound IIC-3 (3.0 g, 7.5 mmol) synthesized in Preparation Example 2 was used instead of the compound IIC-1 used in Synthesis Example 20 to obtain 3.76 g , Yield: 60%).

GC-Mass (calculated: 833.38 g / mol, measured: 833 g / mol)

[Synthesis Example 43] Synthesis of Compound 43

The procedure of Synthesis Example 1 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 1 to obtain 3.03 g , Yield: 64%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 44] Synthesis of Compound 44

The procedure of Synthesis Example 2 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 2 to obtain 3.66 g , Yield: 69%).

GC-Mass (calculated: 705.29 g / mol, measured: 705 g / mol)

[Synthesis Example 45] Synthesis of Compound 45

The procedure of Synthesis Example 3 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 3 to obtain 3.45 g , Yield: 67%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 46] Synthesis of Compound 46

The procedure of Synthesis Example 4 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 4 to obtain 3.65 g , Yield: 62%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 47] Synthesis of Compound 47

The procedure of Synthesis Example 11 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 11 to obtain Compound 47 (1.78 g , Yield: 43%).

GC-Mass (calculated: 551.24 g / mol, measured: 551 g / mol)

[Synthesis Example 48] Synthesis of Compound 48

The procedure of Synthesis Example 12 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 12 to obtain 2.65 g , Yield: 55%).

GC-Mass (calculated: 639.27 g / mol, measured: 639 g / mol)

[Synthesis Example 49] Synthesis of Compound 49

The procedure of Synthesis Example 15 was repeated except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 15 to obtain 3.17 g , Yield: 70%).

GC-Mass (theory: 602.25 g / mol, measurement: 602 g / mol)

[Synthesis Example 50] Synthesis of Compound 50

The procedure of Synthesis Example 16 was repeated, except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 16 to obtain 3.17 g , Yield: 62%).

GC-Mass (theory: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 51] Synthesis of Compound 51

The procedure of Synthesis Example 17 was repeated, except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 17 to obtain 3.52 g , Yield: 69%).

GC-Mass (calculated: 678.28 g / mol, measured: 678 g / mol)

[Synthesis Example 52] Synthesis of Compound 52

The same procedure as in Synthesis Example 20 was conducted, except that the compound IIC-4 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 20 to obtain 4.45 g , Yield: 71%).

GC-Mass (calculated: 833.38 g / mol, measured: 833 g / mol)

[Synthesis Example 53] Synthesis of Compound 53

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

GC-Mass (calculated: 705.29 g / mol, measured: 705 g / mol)

[Synthesis Example 54] Synthesis of Compound 54

The procedure of Synthesis Example 3 was repeated except that the compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 3 to obtain 3.99 g , Yield: 68%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 55] Synthesis of Compound 55

The procedure of Synthesis Example 11 was repeated except that the compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 11 to obtain Compound 55 (1.24 g , Yield: 30%).

GC-Mass (calculated: 551.24 g / mol, measured: 551 g / mol)

[Synthesis Example 56] Synthesis of Compound 56

The procedure of Synthesis Example 15 was repeated except that the compound IIC-5 (3.0 g, 7.5 mmol) synthesized in Preparation Example 3 was used instead of the compound IIC-1 used in Synthesis Example 15 to obtain 0.68 g , Yield: 15%).

GC-Mass (theory: 602.25 g / mol, measurement: 602 g / mol)

[Synthesis Example 57] Synthesis of Compound 57

The procedure of Synthesis Example 1 was repeated except that the compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of the compound IIC-1 used in Synthesis Example 1 to obtain 3.27 g , Yield: 69%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 58] Synthesis of Compound 58

The procedure of Synthesis Example 2 was repeated, except that the compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of the compound IIC-1 used in Synthesis Example 2 to obtain 4.24 g , Yield: 80%).

GC-Mass (calculated: 705.29 g / mol, measured: 705 g / mol)

[Synthesis Example 59] Synthesis of Compound 59

The procedure of Synthesis Example 3 was repeated, except that the compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of the compound IIC-1 used in Synthesis Example 3 to obtain 4.59 g , Yield: 77%).

GC-Mass (theory: 781.32 g / mol, measured: 781 g / mol)

[Synthesis Example 60] Synthesis of Compound 60

The procedure of Synthesis Example 15 was repeated except that the compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of the compound IIC-1 used in Synthesis Example 15 to obtain 2.95 g , Yield: 65%).

GC-Mass (theory: 602.25 g / mol, measurement: 602 g / mol)

[Synthesis Example 61] Synthesis of Compound 61

The procedure of Synthesis Example 20 was repeated except that the compound IIC-6 (3.0 g, 7.5 mmol) synthesized in Preparation Example 4 was used instead of the compound IIC-1 used in Synthesis Example 20 to obtain 3.61 g , Yield: 55%).

GC-Mass (calculated: 833.38 g / mol, measured: 833 g / mol)

[Synthesis Example 62] Synthesis of Compound 62

The procedure of Synthesis Example 1 was repeated except that the compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of the compound IIC-1 used in Synthesis Example 1, 62 (2.90 g, yield 65%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 63] Synthesis of Compound 63

The procedure of Synthesis Example 2 was repeated except that the compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of the compound IIC-1 used in the Preparation Example 2, 63 (3.76 g, yield: 76%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 64] Synthesis of Compound 64

The procedure of Synthetic Example 3 was repeated except that the compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of the compound IIC-1 used in Synthetic Example 3, 64 (3.91 g, yield: 72%).

GC-Mass (calculated: 858.04 g / mol, measured: 858 g / mol)

[Synthesis Example 65] Synthesis of Compound 65

The procedure of Synthesis Example 15 was repeated except that the compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9 was used instead of the compound IIC-1 used in Synthesis Example 15 to obtain Compound 65 2.70 g, yield: 63%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 66] Synthesis of Compound 66

The procedure of Synthetic Example 20 was repeated except that the compound IIC-7-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-1 was used instead of the compound IIC-1 used in Synthesis Example 20, 66 (2.93 g, yield: 51%).

GC-Mass (calculated: 910.15 g / mol, measured: 910 g / mol)

[Synthesis Example 67] Synthesis of Compound 67

The procedure of Synthesis Example 1 was repeated except that the compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of the compound IIC-1 used in Synthesis Example 1, 67 (2.90 g, yield 65%).

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[Synthesis Example 68] Synthesis of Compound 68

The procedure of Synthesis Example 2 was repeated except that the compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of the compound IIC-1 used in Synthesis Example 2, 68 (3.75 g, yield: 76%).

GC-Mass (theory: 782.93 g / mol, measured: 782 g / mol)

[Synthesis Example 69] Synthesis of Compound 69

The procedure of Synthesis Example 3 was repeated except that the compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of the compound IIC-1 used in Synthesis Example 3, 69 (3.90 g, yield: 72%).

GC-Mass (calculated: 859.03 g / mol, measured: 859 g / mol)

[Synthesis Example 70] Synthesis of Compound 70

The procedure of Synthesis Example 15 was repeated except that the compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of the compound IIC-1 used in Synthesis Example 15 to give the compound 70 (2.70 g, yield: 63%).

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[Synthesis Example 71] Synthesis of Compound 71

The procedure of Synthetic Example 20 was repeated except that the compound IIC-7-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 9-2 was used instead of the compound IIC-1 used in Synthetic Example 20, 71 (2.93 g, yield: 51%).

GC-Mass (calculated: 911.14 g / mol, measured: 911 g / mol)

[Synthesis Example 72] Synthesis of Compound 72

The procedure of Synthesis Example 1 was repeated except that the compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of the compound IIC-1 used in Synthesis Example 1, 72 (2.65 g, yield 65%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[Synthesis Example 73] Synthesis of Compound 73

The procedure of Synthesis Example 2 was repeated, except that the compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of the compound IIC-1 used in Synthesis Example 2, 73 (3.38 g, yield: 76%).

GC-Mass (947.13 g / mol, measured: 947 g / mol)

[Synthesis Example 74] Synthesis of Compound 74

The procedure of Synthesis Example 3 was repeated except that the compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of the compound IIC-1 used in Synthesis Example 3, 74 (3.45 g, yield: 72%).

GC-Mass (calculated: 1023.23 g / mol, measured: 1023 g / mol)

[Synthesis Example 75] Synthesis of Compound 75

The procedure of Synthesis Example 15 was repeated, except that the compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of the compound IIC-1 used in Synthesis Example 15, 75 (2.49 g, yield: 63%).

GC-Mass (calculated: 844.01 g / mol, measured: 844 g / mol)

[Synthesis Example 76] Synthesis of Compound 76

The procedure of Synthesis Example 20 was repeated except that the compound IIC-7-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 9-3 was used instead of the compound IIC-1 used in Synthesis Example 20, 76 (2.57 g, yield: 51%).

GC-Mass (calculated: 1075.34 g / mol, measured: 1075 g / mol)

[Synthesis Example 77] Synthesis of Compound 77

The procedure of Synthesis Example 1 was repeated except that the compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 77 (2.73 g, yield 65%).

GC-Mass (calculated: 811.99 g / mol, measured: 811 g / mol)

[Synthesis Example 78] Synthesis of Compound 78

The same procedure as in Synthesis Example 2 was carried out except that the compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of the compound IIC-1 used in the Preparation Example 2, 78 (4.59 g, yield: 76%).

GC-Mass (calculated: 888.09 g / mol, measured: 888 g / mol)

[Synthesis Example 79] Synthesis of Compound 79

The procedure of Synthesis Example 3 was repeated except that the compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of the compound IIC-1 used in Synthesis Example 3, 79 (3.59 g, yield: 72%).

GC-Mass (calculated: 964.18 g / mol, measured: 964 g / mol)

[Synthesis Example 80] Synthesis of Compound 80

The procedure of Synthesis Example 15 was repeated, except that the compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of the compound IIC-1 used in Synthesis Example 15, 80 (2.55 g, yield: 63%).

GC-Mass (calculated: 784.97 g / mol, measured: 784 g / mol)

[Synthesis Example 81] Synthesis of Compound 81

The procedure of Synthetic Example 20 was repeated except that the compound IIC-7-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 9-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 81 (2.68 g, yield: 51%).

GC-Mass (1016.30 g / mol, measured: 1016 g / mol)

[Synthesis Example 82] Synthesis of Compound 82

The procedure of Synthesis Example 1 was repeated except that the compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of the compound IIC-1 used in Synthesis Example 1, 82 (2.90 g, yield 65%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 83] Synthesis of Compound 83

The procedure of Synthesis Example 2 was repeated except that the compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of the compound IIC-1 used in the synthesis example 2, 83 (3.76 g, yield: 76%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 84] Synthesis of Compound 84

The procedure of Synthesis Example 3 was repeated except that the compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of the compound IIC-1 used in Synthesis Example 3, 64 (3.91 g, yield: 72%).

GC-Mass (calculated: 858.04 g / mol, measured: 858 g / mol)

[Synthesis Example 85] Synthesis of Compound 85

The procedure of Synthesis Example 15 was repeated except that the compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of the compound IIC-1 used in Synthesis Example 15, 85 (2.70 g, yield: 63%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 86] Synthesis of Compound 86

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-8-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-1 was used instead of the compound IIC-1 used in Synthesis Example 20, 86 (2.93 g, yield: 51%).

GC-Mass (calculated: 910.15 g / mol, measured: 910 g / mol)

[Synthesis Example 87] Synthesis of Compound 87

The procedure of Synthesis Example 1 was repeated except that the compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of the compound IIC-1 used in Synthesis Example 1, 87 (2.90 g, yield: 65%).

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[Synthesis Example 88] Synthesis of Compound 88

The procedure of Synthesis Example 2 was repeated except that the compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of the compound IIC-1 used in Synthesis Example 2, 88 (3.75 g, yield: 76%).

GC-Mass (theory: 782.93 g / mol, measured: 782 g / mol)

[Synthesis Example 89] Synthesis of Compound 89

The procedure of Synthesis Example 3 was repeated except that the compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of the compound IIC-1 used in Synthesis Example 3, 89 (3.90 g, yield: 72%).

GC-Mass (calculated: 859.03 g / mol, measured: 859 g / mol)

[Synthesis Example 90] Synthesis of Compound 90

The procedure of Synthesis Example 15 was repeated except that the compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of the compound IIC-1 used in Synthesis Example 15, 90 (2.70 g, yield: 63%).

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[Synthesis 91] Synthesis of Compound 91

The procedure of Synthetic Example 20 was repeated except that the compound IIC-8-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 10-2 was used instead of the compound IIC-1 used in Synthetic Example 20, 91 (2.93 g, yield: 51%).

GC-Mass (calculated: 911.14 g / mol, measured: 911 g / mol)

[Synthesis Example 92] Synthesis of Compound 92

The procedure of Synthesis Example 1 was repeated except that the compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of the compound IIC-1 used in Synthesis Example 1, 92 (2.65 g, yield 65%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[Synthesis Example 93] Synthesis of Compound 93

The procedure of Synthesis Example 2 was repeated except that the compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of the compound IIC-1 used in Synthesis Example 2, 93 (3.38 g, yield: 76%).

GC-Mass (947.13 g / mol, measured: 947 g / mol)

[Synthesis Example 94] Synthesis of Compound 94

The procedure of Synthesis Example 3 was repeated except that the compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of the compound IIC-1 used in Synthesis Example 3, 94 (3.45 g, yield: 72%).

GC-Mass (calculated: 1023.23 g / mol, measured: 1023 g / mol)

[Synthesis Example 95] Synthesis of Compound 95

The procedure of Synthesis Example 15 was repeated except that the compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of the compound IIC-1 used in Synthesis Example 15, 95 (2.49 g, yield: 63%).

GC-Mass (calculated: 844.01 g / mol, measured: 844 g / mol)

[Synthesis Example 96] Synthesis of Compound 96

The procedure of Synthesis Example 20 was repeated except that the compound IIC-8-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 10-3 was used instead of the compound IIC-1 used in Synthesis Example 20, 96 (2.57 g, yield: 51%).

GC-Mass (calculated: 1075.34 g / mol, measured: 1075 g / mol)

[Synthesis Example 97] Synthesis of Compound 97

The procedure of Synthesis Example 1 was repeated except that the compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 97 (2.73 g, yield 65%).

GC-Mass (calculated: 811.99 g / mol, measured: 811 g / mol)

[Synthesis Example 98] Synthesis of Compound 98

The procedure of Synthesis Example 2 was repeated except that the compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of the compound IIC-1 used in Synthesis Example 2, 98 (4.59 g, yield: 76%).

GC-Mass (calculated: 888.09 g / mol, measured: 888 g / mol)

[Synthesis Example 99] Synthesis of Compound 99

The procedure of Synthesis Example 3 was repeated except that the compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of the compound IIC-1 used in Synthesis Example 3, 99 (3.59 g, yield: 72%).

GC-Mass (calculated: 964.18 g / mol, measured: 964 g / mol)

[Synthesis Example 100] Synthesis of Compound 100

The procedure of Synthesis Example 15 was repeated except that the compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of the compound IIC-1 used in Synthesis Example 15, 100 (2.55 g, yield: 63%).

GC-Mass (calculated: 784.97 g / mol, measured: 784 g / mol)

[Synthesis Example 101] Synthesis of Compound 101

The procedure of Synthesis Example 20 was repeated, except that the compound IIC-8-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 10-4 was used instead of the compound IIC-1 used in Synthesis Example 20, 101 (2.68 g, yield: 51%).

GC-Mass (1016.30 g / mol, measured: 1016 g / mol)

[ Synthetic example  102] Synthesis of Compound 102

The procedure of Synthesis Example 1 was repeated, except that the compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of the compound IIC-1 used in Synthesis Example 1, 102 (2.90 g, yield 65%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 103] Synthesis of Compound 103

The procedure of Synthesis Example 2 was repeated, except that the compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of the compound IIC-1 used in Synthesis Example 2, 103 (3.76 g, yield: 76%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 104] Synthesis of Compound 104

The procedure of Synthesis Example 3 was repeated except that the compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of the compound IIC-1 used in Synthesis Example 3, 104 (3.91 g, yield: 72%).

GC-Mass (calculated: 858.04 g / mol, measured: 858 g / mol)

[Synthesis Example 105] Synthesis of Compound 105

The procedure of Synthesis Example 15 was repeated, except that the compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of the compound IIC-1 used in Synthesis Example 15, 105 (2.70 g, yield: 63%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 106] Synthesis of Compound 106

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-9-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-1 was used instead of the compound IIC-1 used in Synthetic Example 20, 106 (2.93 g, yield: 51%).

GC-Mass (calculated: 910.15 g / mol, measured: 910 g / mol)

[Synthesis Example 107] Synthesis of Compound 107

The procedure of Synthesis Example 1 was repeated except that the compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of the compound IIC-1 used in Synthesis Example 1, 107 (2.90 g, yield: 65%).

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[Synthesis Example 108] Synthesis of Compound 108

The procedure of Synthesis Example 2 was repeated except that the compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of the compound IIC-1 used in the synthesis example 2, 108 (3.75 g, yield: 76%).

GC-Mass (theory: 782.93 g / mol, measured: 782 g / mol)

[Synthesis Example 109] Synthesis of Compound 109

The procedure of Synthesis Example 3 was repeated except that the compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of the compound IIC-1 used in Synthesis Example 3, 109 (3.90 g, yield: 72%).

GC-Mass (calculated: 859.03 g / mol, measured: 859 g / mol)

[Synthesis Example 110] Synthesis of Compound 110

The procedure of Synthesis Example 15 was repeated except that the compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of the compound IIC-1 used in Synthesis Example 15, 110 (2.70 g, yield: 63%).

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[Synthesis Example 111] Synthesis of Compound 111

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-9-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 11-2 was used instead of the compound IIC-1 used in Synthetic Example 20, 111 (2.93 g, yield: 51%).

GC-Mass (calculated: 911.14 g / mol, measured: 911 g / mol)

[Synthesis Example 112] Synthesis of Compound 112

The procedure of Synthesis Example 1 was repeated except that the compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used instead of the compound IIC-1 used in Synthesis Example 1, 112 (2.65 g, yield 65%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[Synthesis Example 113] Synthesis of Compound 113

The procedure of Synthesis Example 2 was repeated except that the compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used instead of the compound IIC-1 used in Synthesis Example 2, 113 (3.38 g, yield: 76%).

GC-Mass (947.13 g / mol, measured: 947 g / mol)

[Synthesis Example 114] Synthesis of Compound 114

The procedure of Synthesis Example 3 was repeated except that the compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used instead of the compound IIC-1 used in Synthesis Example 3, 114 (3.45 g, yield: 72%).

GC-Mass (calculated: 1023.23 g / mol, measured: 1023 g / mol)

[Synthesis Example 115] Synthesis of Compound 115

The procedure of Synthesis Example 15 was repeated, except that the compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used instead of the compound IIC-1 used in Synthesis Example 15, 115 (2.49 g, yield: 63%).

GC-Mass (calculated: 844.01 g / mol, measured: 844 g / mol)

[Synthesis Example 116] Synthesis of Compound 116

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-9-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 11-3 was used instead of the compound IIC-1 used in Synthesis Example 20, 116 (2.57 g, yield: 51%).

GC-Mass (calculated: 1075.34 g / mol, measured: 1075 g / mol)

[Synthesis Example 117] Synthesis of Compound 117

The procedure of Synthesis Example 1 was repeated except that the compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 117 (2.73 g, yield 65%).

GC-Mass (calculated: 811.99 g / mol, measured: 811 g / mol)

[Synthesis Example 118] Synthesis of Compound 118

The procedure of Synthesis Example 2 was repeated except that the compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of the compound IIC-1 used in Synthesis Example 2, 118 (4.59 g, yield: 76%).

GC-Mass (calculated: 888.09 g / mol, measured: 888 g / mol)

[Synthesis Example 119] Synthesis of Compound 119

The procedure of Synthesis Example 3 was repeated except that the compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of the compound IIC-1 used in Synthesis Example 3, 119 (3.59 g, yield: 72%).

GC-Mass (calculated: 964.18 g / mol, measured: 964 g / mol)

[Synthesis Example 120] Synthesis of Compound 120

The procedure of Synthesis Example 15 was repeated except that the compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of the compound IIC-1 used in Synthesis Example 15, 120 (2.55 g, yield: 63%).

GC-Mass (calculated: 784.97 g / mol, measured: 784 g / mol)

[Synthesis Example 121] Synthesis of Compound 121

The procedure of Synthesis Example 20 was repeated except that the compound IIC-9-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 11-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 121 (2.68 g, yield: 51%).

GC-Mass (1016.30 g / mol, measured: 1016 g / mol)

[Synthesis Example 122] Synthesis of Compound 122

The procedure of Synthesis Example 1 was repeated except that the compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of the compound IIC-1 used in Synthesis Example 1, 122 (2.90 g, yield 65%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 123] Synthesis of Compound 123

The procedure of Synthesis Example 2 was repeated except that the compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of the compound IIC-1 used in Synthesis Example 2, 123 (3.76 g, yield: 76%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 124] Synthesis of Compound 124

The procedure of Synthesis Example 3 was repeated except that the compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of the compound IIC-1 used in Synthesis Example 3, 124 (3.91 g, yield: 72%).

GC-Mass (calculated: 858.04 g / mol, measured: 858 g / mol)

[Synthesis Example 125] Synthesis of Compound 125

The procedure of Synthesis Example 15 was repeated, except that the compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of the compound IIC-1 used in Synthesis Example 15, 125 (2.70 g, yield: 63%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 126] Synthesis of Compound 126

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-10-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-1 was used instead of the compound IIC-1 used in Synthesis Example 20, 126 (2.93 g, yield: 51%).

GC-Mass (calculated: 910.15 g / mol, measured: 910 g / mol)

[Synthesis Example 127] Synthesis of Compound 127

The procedure of Synthesis Example 1 was repeated except that the compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of the compound IIC-1 used in Synthesis Example 1, 127 (2.90 g, yield 65%).

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[Synthesis Example 128] Synthesis of Compound 128

The procedure of Synthesis Example 2 was repeated except that the compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of the compound IIC-1 used in Synthesis Example 2, 128 (3.75 g, yield: 76%).

GC-Mass (theory: 782.93 g / mol, measured: 782 g / mol)

[Synthesis Example 129] Synthesis of Compound 129

The procedure of Synthesis Example 3 was repeated except that the compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of the compound IIC-1 used in the synthesis example 3, 129 (3.90 g, yield: 72%).

GC-Mass (calculated: 859.03 g / mol, measured: 859 g / mol)

[Synthesis Example 130] Synthesis of Compound 130

The procedure of Synthesis Example 15 was repeated except that the compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of the compound IIC-1 used in Synthesis Example 15, 130 (2.70 g, yield: 63%).

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[Synthesis Example 131] Synthesis of Compound 131

The procedure of Synthetic Example 20 was repeated except that the compound IIC-10-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 12-2 was used instead of the compound IIC-1 used in Synthetic Example 20, 131 (2.93 g, yield: 51%).

GC-Mass (calculated: 911.14 g / mol, measured: 911 g / mol)

[Synthesis Example 132] Synthesis of Compound 132

The procedure of Synthesis Example 1 was repeated except that the compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used instead of the compound IIC-1 used in Synthesis Example 1, 132 (2.65 g, yield: 65%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[Synthesis Example 133] Synthesis of Compound 133

The procedure of Synthesis Example 2 was repeated except that the compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used instead of the compound IIC-1 used in Synthesis Example 2, 133 (3.38 g, yield: 76%).

GC-Mass (947.13 g / mol, measured: 947 g / mol)

[Synthesis Example 134] Synthesis of Compound 134

The procedure of Synthesis Example 3 was repeated except that the compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used instead of the compound IIC-1 used in Synthesis Example 3, 134 (3.45 g, yield: 72%).

GC-Mass (calculated: 1023.23 g / mol, measured: 1023 g / mol)

[Synthesis Example 135] Synthesis of Compound 135

The procedure of Synthesis Example 15 was repeated except that the compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used instead of the compound IIC-1 used in Synthesis Example 15, 135 (2.49 g, yield: 63%).

GC-Mass (calculated: 844.01 g / mol, measured: 844 g / mol)

[Synthesis Example 136] Synthesis of Compound 136

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-10-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 12-3 was used instead of the compound IIC-1 used in Synthesis Example 20, 136 (2.57 g, yield: 51%).

GC-Mass (calculated: 1075.34 g / mol, measured: 1075 g / mol)

[Synthesis Example 137] Synthesis of Compound 137

The procedure of Synthesis Example 1 was repeated except that the compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 137 (2.73 g, yield 65%).

GC-Mass (calculated: 811.99 g / mol, measured: 811 g / mol)

[Synthesis Example 138] Synthesis of Compound 138

The procedure of Synthesis Example 2 was repeated except that the compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of the compound IIC-1 used in Synthesis Example 2, 138 (4.59 g, yield: 76%).

GC-Mass (calculated: 888.09 g / mol, measured: 888 g / mol)

[Synthesis Example 139] Synthesis of Compound 139

The procedure of Synthesis Example 3 was repeated except that the compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of the compound IIC-1 used in Synthesis Example 3, 139 (3.59 g, yield: 72%).

GC-Mass (calculated: 964.18 g / mol, measured: 964 g / mol)

[Synthesis Example 140] Synthesis of Compound 140

The procedure of Synthesis Example 15 was repeated except that the compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of the compound IIC-1 used in Synthesis Example 15, 140 (2.55 g, yield: 63%).

GC-Mass (calculated: 784.97 g / mol, measured: 784 g / mol)

[Synthesis Example 141] Synthesis of Compound 141

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-10-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 12-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 141 (2.68 g, yield: 51%).

GC-Mass (1016.30 g / mol, measured: 1016 g / mol)

[Synthesis Example 142] Synthesis of Compound 142

The procedure of Synthesis Example 1 was repeated except that the compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of the compound IIC-1 used in Synthesis Example 1, 142 (2.90 g, yield: 65%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 143] Synthesis of Compound 143

The procedure of Synthesis Example 2 was repeated except that the compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of the compound IIC-1 used in Synthesis Example 2, 143 (3.76 g, yield: 76%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 144] Synthesis of Compound 144

The procedure of Synthesis Example 3 was repeated except that the compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of the compound IIC-1 used in Synthesis Example 3, 144 (3.91 g, yield: 72%).

GC-Mass (calculated: 858.04 g / mol, measured: 858 g / mol)

[Synthesis Example 145] Synthesis of Compound 145

The procedure of Synthesis Example 15 was repeated except that the compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of the compound IIC-1 used in Synthesis Example 15, 145 (2.70 g, yield: 63%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 146] Synthesis of Compound 146

The procedure of Synthetic Example 20 was repeated except that the compound IIC-11-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-1 was used instead of the compound IIC-1 used in Synthetic Example 20, 146 (2.93 g, yield: 51%).

GC-Mass (calculated: 910.15 g / mol, measured: 910 g / mol)

[Synthesis Example 147] Synthesis of Compound 147

The procedure of Synthesis Example 1 was repeated except that the compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of the compound IIC-1 used in Synthesis Example 1, 147 (2.90 g, yield 65%).

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[Synthesis Example 148] Synthesis of Compound 148

The procedure of Synthesis Example 2 was repeated except that the compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of the compound IIC-1 used in the synthesis example 2, 148 (3.75 g, yield: 76%).

GC-Mass (theory: 782.93 g / mol, measured: 782 g / mol)

[Synthesis Example 149] Synthesis of Compound 149

The procedure of Synthesis Example 3 was repeated except that the compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of the compound IIC-1 used in Synthesis Example 3, 149 (3.90 g, yield: 72%).

GC-Mass (calculated: 859.03 g / mol, measured: 859 g / mol)

[Synthesis Example 150] Synthesis of Compound 150

The procedure of Synthesis Example 15 was repeated except that the compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of the compound IIC-1 used in Synthesis Example 15, 150 (2.70 g, yield: 63%).

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[Synthesis Example 151] Synthesis of Compound 151

The procedure of Synthetic Example 20 was repeated except that the compound IIC-11-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 13-2 was used instead of the compound IIC-1 used in Synthetic Example 20, 151 (2.93 g, yield: 51%).

GC-Mass (calculated: 911.14 g / mol, measured: 911 g / mol)

[Synthesis Example 152] Synthesis of Compound 152

The procedure of Synthesis Example 1 was repeated except that the compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used instead of the compound IIC-1 used in Synthesis Example 1, 152 (2.65 g, yield 65%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[Synthesis Example 153] Synthesis of Compound 153

The procedure of Synthesis Example 2 was repeated except that the compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used instead of the compound IIC-1 used in Synthesis Example 2, 153 (3.38 g, yield: 76%).

GC-Mass (947.13 g / mol, measured: 947 g / mol)

[Synthesis Example 154] Synthesis of Compound 154

The procedure of Synthesis Example 3 was repeated except that the compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used instead of the compound IIC-1 used in Synthesis Example 3, 154 (3.45 g, yield: 72%).

GC-Mass (calculated: 1023.23 g / mol, measured: 1023 g / mol)

[Synthesis Example 155] Synthesis of Compound 155

The procedure of Synthesis Example 15 was repeated except that the compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used instead of the compound IIC-1 used in Synthesis Example 15, 155 (2.49 g, yield: 63%).

GC-Mass (calculated: 844.01 g / mol, measured: 844 g / mol)

[Synthesis Example 156] Synthesis of Compound 156

The procedure of Synthetic Example 20 was repeated except that the compound IIC-11-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 13-3 was used instead of the compound IIC-1 used in Synthesis Example 20, 156 (2.57 g, yield: 51%).

GC-Mass (calculated: 1075.34 g / mol, measured: 1075 g / mol)

[Synthesis Example 157] Synthesis of Compound 157

The procedure of Synthesis Example 1 was repeated except that the compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 157 (2.73 g, yield 65%).

GC-Mass (calculated: 811.99 g / mol, measured: 811 g / mol)

[Synthesis Example 158] Synthesis of Compound 158

The procedure of Synthesis Example 2 was repeated except that the compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of the compound IIC-1 used in Synthesis Example 2, 158 (4.59 g, yield: 76%).

GC-Mass (calculated: 888.09 g / mol, measured: 888 g / mol)

[Synthesis Example 159] Synthesis of Compound 159

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

GC-Mass (calculated: 964.18 g / mol, measured: 964 g / mol)

[Synthesis Example 160] Synthesis of Compound 160

The procedure of Synthesis Example 15 was repeated except that the compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of the compound IIC-1 used in Synthesis Example 15, 160 (2.55 g, yield: 63%).

GC-Mass (calculated: 784.97 g / mol, measured: 784 g / mol)

[Synthesis Example 161] Synthesis of Compound 161

The procedure of Synthetic Example 20 was repeated, except that the compound IIC-11-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 13-4 was used instead of the compound IIC-1 used in Synthesis Example 20, 161 (2.68 g, yield: 51%).

GC-Mass (1016.30 g / mol, measured: 1016 g / mol)

 [Synthesis Example 162] Synthesis of Compound 162

The procedure of Synthesis Example 1 was repeated except that the compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of the compound IIC-1 used in Synthesis Example 1, 162 (2.90 g, yield 65%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 163] Synthesis of Compound 163

The procedure of Synthesis Example 2 was repeated except that the compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of the compound IIC-1 used in Synthesis Example 2, 163 (3.76 g, yield: 76%).

GC-Mass (theory: 781.94 g / mol, measured: 781 g / mol)

[Synthesis Example 164] Synthesis of Compound 164

The procedure of Synthesis Example 3 was repeated except that the compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of the compound IIC-1 used in Synthesis Example 3, 164 (3.91 g, yield: 72%).

GC-Mass (calculated: 858.04 g / mol, measured: 858 g / mol)

[Synthesis Example 165] Synthesis of Compound 165

The procedure of Synthesis Example 15 was repeated except that the compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of the compound IIC-1 used in Synthesis Example 15, 165 (2.70 g, yield: 63%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 166] Synthesis of Compound 166

The procedure of Synthesis Example 20 was repeated except that the compound IIC-12-1 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-1 was used instead of the compound IIC-1 used in Synthesis Example 20, 166 (2.93 g, yield: 51%).

GC-Mass (calculated: 910.15 g / mol, measured: 910 g / mol)

[Synthesis Example 167] Synthesis of Compound 167

The procedure of Synthesis Example 1 was repeated except that the compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of the compound IIC-1 used in Synthesis Example 1, 167 (2.90 g, yield 65%).

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[Synthesis Example 168] Synthesis of Compound 168

The procedure of Synthesis Example 2 was repeated except that the compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of the compound IIC-1 used in Synthesis Example 2, 168 (3.75 g, yield: 76%).

GC-Mass (theory: 782.93 g / mol, measured: 782 g / mol)

[Synthesis Example 169] Synthesis of Compound 169

The procedure of Synthesis Example 3 was repeated except that the compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of the compound IIC-1 used in Synthesis Example 3, 169 (3.90 g, yield: 72%).

GC-Mass (calculated: 859.03 g / mol, measured: 859 g / mol)

[Synthesis Example 170] Synthesis of Compound 170

The procedure of Synthesis Example 15 was repeated except that the compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of the compound IIC-1 used in Synthesis Example 15, 170 (2.70 g, yield: 63%).

GC-Mass (calculated: 679.81 g / mol, measured: 679 g / mol)

[Synthesis Example 171] Synthesis of Compound 171

The procedure of Synthetic Example 20 was repeated except that the compound IIC-12-2 (3.0 g, 6.3 mmol) synthesized in Preparation Example 14-2 was used instead of the compound IIC-1 used in Synthetic Example 20, 171 (2.93 g, yield: 51%).

GC-Mass (calculated: 911.14 g / mol, measured: 911 g / mol)

[Synthesis Example 172] Synthesis of Compound 172

The procedure of Synthesis Example 1 was repeated except that the compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used instead of the compound IIC-1 used in Synthesis Example 1, 172 (2.65 g, yield 65%).

GC-Mass (theory: 871.04 g / mol, measured: 871 g / mol)

[Synthesis Example 173] Synthesis of Compound 173

The procedure of Synthesis Example 2 was repeated except that the compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used instead of the compound IIC-1 used in Synthesis Example 2, 173 (3.38 g, yield: 76%).

GC-Mass (947.13 g / mol, measured: 947 g / mol)

[Synthesis Example 174] Synthesis of Compound 174

The procedure of Synthesis Example 3 was repeated except that the compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used instead of the compound IIC-1 used in Synthesis Example 3, 174 (3.45 g, yield: 72%).

GC-Mass (calculated: 1023.23 g / mol, measured: 1023 g / mol)

[Synthesis Example 175] Synthesis of Compound 175

The procedure of Synthesis Example 15 was repeated except that the compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used instead of the compound IIC-1 used in Synthesis Example 15, 175 (2.49 g, yield: 63%).

GC-Mass (calculated: 844.01 g / mol, measured: 844 g / mol)

[Synthesis Example 176] Synthesis of Compound 176

The procedure of Synthesis Example 20 was repeated except that the compound IIC-12-3 (3.0 g, 4.7 mmol) synthesized in Preparation Example 14-3 was used instead of the compound IIC-1 used in Synthesis Example 20, 176 (2.57 g, yield: 51%).

GC-Mass (calculated: 1075.34 g / mol, measured: 1075 g / mol)

[Synthesis Example 177] Synthesis of Compound 177

The procedure of Synthesis Example 1 was repeated except that the compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of the compound IIC-1 used in Synthesis Example 1, 177 (2.73 g, yield 65%).

GC-Mass (calculated: 811.99 g / mol, measured: 811 g / mol)

[Synthesis Example 178] Synthesis of Compound 178

The procedure of Synthesis Example 2 was repeated except that the compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of the compound IIC-1 used in the Synthesis Example 2, 178 (4.59 g, yield: 76%).

GC-Mass (calculated: 888.09 g / mol, measured: 888 g / mol)

[Synthesis Example 179] Synthesis of Compound 179

The procedure of Synthesis Example 3 was repeated except that the compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of the compound IIC-1 used in Synthesis Example 3, 179 (3.59 g, yield: 72%).

GC-Mass (calculated: 964.18 g / mol, measured: 964 g / mol)

[Synthesis Example 180] Synthesis of Compound 180

The procedure of Synthesis Example 15 was repeated, except that the compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of the compound IIC-1 used in Synthesis Example 15, 180 (2.55 g, yield: 63%).

GC-Mass (calculated: 784.97 g / mol, measured: 784 g / mol)

[Synthesis Example 181] Synthesis of Compound 181

The procedure of Synthesis Example 20 was repeated except that the compound IIC-12-4 (3.0 g, 5.2 mmol) synthesized in Preparation Example 14-4 was used instead of the compound IIC-1 used in Synthesis Example 20, 181 (2.68 g, yield: 51%).

GC-Mass (1016.30 g / mol, measured: 1016 g / mol)

[Example 1] Production 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 produced as follows.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech), and then the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

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 that order.

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

[Examples 2 to 181] Preparation of green organic EL device

An organic EL device was manufactured in the same manner as in Example 1 except that the compounds 2 to 181 synthesized in Synthesis Examples 2 to 181 were used instead of the compound 1 used as a host material in the formation of the light emitting layer in Example 1 Respectively.

[ Comparative Example ] Green organic EL  Device manufacturing

An organic EL device was fabricated in the same manner as in Example 1, except that the following CBP was used in place of the compound 1 used as the host material in forming the light emitting layer in Example 1. The structure of CBP used is as follows.

[ Experimental Example  One]

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

Host The 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 Synthesis of 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

As shown in Table 1, the green organic EL devices (Examples 1 to 65) using the compounds represented by Formula 1 (Compound 1 to 181) according to the present invention as a host material in the light emitting layer, It was confirmed that the organic EL device exhibited better current efficiency and better driving voltage than the organic EL device (Comparative Example 1).

Claims (7)

A compound represented by the following formula (1):
[Chemical Formula 1]

(In the formula 1,
R ₃ to R ₆ are the same as or different from each other and each independently hydrogen, or 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 Have;
Provided that at least one of R ₃ and R _4, R ₄ and R _5, and R ₅ and R ₆ is bonded to each other to form a condensed ring represented by the following formula (2);
(2)

In Formula 2,
The dotted line is a site where condensation is carried out with the compound of Formula 1;
R ₁ , R ₂ , and R ₇ to R ₁₀ are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group , And a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, or R ₁ and R ₂ , R ₇ and R ₈ , R ₈ and R ₉ , and at least one of R ₉ and R ₁₀ One may combine with each other to form a condensed ring;
n is an integer from 0 to 4, at least one Ra is each independently hydrogen, or other Ra adjacent to Ra may combine with each other to form a condensed ring;
X ₁ and X ₂ are each independently N (Ar ₁ );
Ar ₁ is the same or different and is selected from the group consisting of a substituted or unsubstituted C ₆ to C ₄₀ aryl group and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms;
An aryl group or a heteroaryl group in the R ₁ , R ₂ , and R ₇ to R ₁₀ ; and in the Ar ₁ , the aryl group and the heteroaryl group are each independently selected from the group consisting of deuterium, a C ₆ to C ₄₀ aryl group, A heteroaryl group having from 5 to 40 carbon atoms, and an arylamine group having from ₆ to ₄₀ carbon atoms, which may be the same or different from each other when plural substituents are present). The method according to claim 1,
Wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (3) to (8):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

(In the above formulas 3 to 8,
R ₁ to R ₁₀ , R a, X ₁ , X ₂ , and n are as defined in claim 1, respectively. delete delete The method according to claim 1,
Wherein Ar ₁ is the same or different from each other and each independently represents a substituent selected from the group consisting of Substituents S 1 to S 31, S 34 to S 112, S 116 to S 140, S 144, S 145 to S 150, S 158 to S 161, S 167 to S 169, S 171 to S 176, S 178 to S 197, 0.0 &gt; S204 &lt; / RTI &gt; and S206.

1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1, 2, and 5. The method according to claim 6,
Wherein at least one of the one or more organic layers including the compound is a light emitting layer.