KR101547623B1 - Organic electroluminescent device - Google Patents

Abstract

The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device using an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by introducing a light emitting layer using an indole compound and an iridium compound as host / Can be provided.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device,

The present invention relates to an organic electroluminescent device in which characteristics such as a driving voltage, a luminous efficiency and a lifetime are improved.

Electroluminescent (EL) devices, which led to blue electroluminescence using anthracene single crystals in 1965, were followed up with the observation of the organic thin film emission of Bernanose in the 1950s. In 1987, Layer and a functional layer of a light-emitting layer. Hereinafter, the organic electroluminescent device has been developed to introduce characteristic organic layers in the device to improve the efficiency and lifetime of the device.

In the organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic layer, and the injected holes and electrons meet to form an exciton. When the exciton formed drops to a ground state The light comes out. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

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. The development of a phosphorescent dopant has been studied not only for a phosphorescent dopant but also for a phosphorescent host since it can theoretically improve luminescence efficiency up to four times that of a fluorescent dopant.

To date, hole transport materials. NPB, BCP, and Alq ₃ are widely known as hole injecting materials and electron transporting materials, and anthracene derivatives are used as light emitting materials. In particular, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like, which have great advantages in terms of efficiency improvement of light emitting materials, are blue, green, It is used as a red phosphorescent dopant material, and CBP is used as a phosphorescent host material.

However, conventional luminescent materials have good luminescence characteristics, but have low glass transition temperature and poor thermal stability, which is not satisfactory in terms of lifetime of an organic electroluminescent device. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

In order to solve the above problems, it is an object of the present invention to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and life span.

In order to achieve the above object, cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the organic material layers is composed of a compound represented by the following formula (1) and a compound represented by the following formula (3) An organic electroluminescent device is provided.

[Chemical Formula 1]

In Formula 1,

Y ₁ to Y ₄ are each independently N or CR ₃ , and Y ₁ and Y ₂ , Y ₂ and Y ₃ , or one of Y ₃ and Y ₄ form a condensed ring represented by the following formula (2)

(2)

In Formula 2,

Y ₅ to Y ₈ each independently represent N or CR ₄ ,

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) , X ₁ and X ₂ At least one of them is N (Ar ₁ )

Each of R ₁ to R ₄ and Ar ₁ to Ar ₅ is independently hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkynyl group, ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ is selected from ~ C ₆₀ aryl boron group, the group consisting of C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of,

R ₁ to R ₄ may be bonded to adjacent groups to form a condensed ring,

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of R ₁ to R ₄ and Ar ₁ to Ar ₅ A halogen atom, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, an aryloxy group, _A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₄₀ aryl group, a substituted or unsubstituted a heteroaryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ from the group consisting of an aryl amine of the C ₆₀ of the And may be substituted with at least one selected.

(3)

In Formula 3,

X is an organic ligand, X is a heteroaryl group having 3 to 40 nuclear atoms, Y is an aryl group having ₆ to ₄₀ carbon atoms or a heteroaryl group having 3 to 40 nuclear atoms, and R ₁₁ to R ₁₈ are independently, hydrogen, deuterium, a halogen, a cyano group, a nitro group, an amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C ₆ ~ C ₆₀ of An aryl group of 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ An arylamine group of C ₆₀ , and may form a condensed ring by bonding with adjacent groups, and n is an integer of 1 to 3.

The alkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl, and the like.

The alkenyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like.

The alkynyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Non-limiting examples thereof include ethynyl, 2-propynyl, and the like.

The cycloalkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

The heterocycloalkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and includes at least one carbon of the ring, preferably 1 To three carbons are substituted with a heteroatom such as N, O or S; Non-limiting examples thereof include morpholine, piperazine, and the like.

The aryl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, triphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, indenyl and the like.

The heteroaryl used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms and is a monovalent group having at least one carbon atom, Carbon atoms are replaced by heteroatoms such as nitrogen (N), oxygen (O), sulfur (S), or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

The alkyloxy used in the present invention means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms and includes a linear, branched or cyclic structure . Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

The aryloxy used in the present invention means a monovalent functional group represented by R'O-, and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

The alkylsilyl used in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms, arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms, arylamine is substituted with aryl having 6 to 60 carbon atoms ≪ / RTI >

The condensed rings used in the present invention means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The organic electroluminescent device of the present invention is characterized in that an indole compound represented by Formula 1 is used as a phosphorescent host in a light emitting layer and an iridium compound represented by Formula 3 is used as a phosphorescent dopant in a light emitting layer, And the characteristics such as light emitting performance, driving voltage and lifetime are excellent.

Hereinafter, the present invention will be described.

The present invention relates to an organic electroluminescent device comprising a cathode, a cathode, and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by the formula An organic electroluminescent device comprising a compound represented by the general formula (3) is provided.

The compound represented by the general formula (1) has a condensed carbon ring or a condensed heterocyclic moiety, preferably a condensed heterocyclic moiety, linked to the indole basic skeleton, and the energy level is controlled by various substituents, to red). Therefore, when the compound represented by the general formula (1) is used for an organic material layer of an organic electroluminescent device, phosphorescence characteristics can be improved and electron and / or hole transporting ability and light emitting ability can be enhanced.

The compound represented by the general formula (1) of the present invention is preferably used in a hole transporting layer, an electron transporting layer and a light emitting layer in the organic material layer, and exhibits excellent characteristics as a light emitting host material compared to the conventional CBP due to the indole based basic skeleton. It is more preferable to use it as a host material.

Specifically, the compound represented by Formula (1) has a structure in which aromatic rings are substituted with various aromatic rings in the indole-based basic skeleton, and the molecular weight of the compound is significantly increased. As a result, the glass transition temperature is improved, And may have thermal stability. In addition, since the molecules have bipolar characteristics due to various aromatic ring substituents and can increase the bonding force between holes and electrons, they can exhibit excellent characteristics as a host material of a light emitting layer as compared with conventional CBP.

In the compounds represented by the formula (1), it is preferable that all of the groups not forming a condensed ring at Y ₁ to Y ₄ are CR ₃ , and a plurality of R _{3 s} may be the same as or different from each other. It is preferable that all of Y ₅ to Y ₈ of the compound represented by the formula (1) are all CR ₄ , and a plurality of R _{4 s} may be the same or different from each other.

Here, considering the wide band-gap and thermal stability of the compound, R ₁ to R ₄ in the formula (1) are each independently selected from the group consisting of hydrogen, a C ₆ -C ₆₀ aryl group (eg, phenyl, naphthyl, Biphenyl) or a heteroaryl group having 5 to 60 nuclear atoms (e.g., pyridine).

The compound represented by the formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the following formulas (1a) to (1f).

[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

In the above formulas (1a) to (1f), X ₁ , X ₂ and R ₁ to R ₄ are as defined above.

It is preferable that X ₁ and X ₂ in formula ( ₁ ) are each independently N (Ar ₁ ) or S, taking into consideration the characteristics such as luminous efficiency, driving voltage and lifetime of the organic electroluminescent device. That is, it is preferable that X ₁ is N (Ar ₁ ), X ₂ is S, X ₁ is S, X ₂ is N (Ar ₁ ), or X ₁ and X ₂ are both N (Ar ₁ ).

More specifically, the compound represented by the formula (1) of the present invention may be selected from the group consisting of compounds represented by the following formulas (C1) to (C66).

In the above formulas C1 to C66, R ₁ to R ₄ are as defined above, and a plurality of R ₃ and R ₄ may be the same or different from each other. Further, Ar ₁ to Ar ₅ are sounds as defined above, particularly C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ C ₆₀ of which is selected from the group consisting of an aryl amine . More specifically, it is more preferable that each of Ar ₁ to Ar ₅ is independently selected from the following substituent (functional group) group (S1-S192).

On the other hand, the compound represented by the above formula (3) has an aromatic ring connected to one side and an organic ligand connected to the other side with iridium (Ir) as a center. Since the organic ligand is connected to the compound represented by Formula 3 of the present invention, the energy gap between the HOMO and the triplet MLCT state can be increased. Accordingly, when the compound represented by the general formula (3) is used for an organic material layer of an organic electroluminescent device, specifically, a hole injecting layer, a hole transporting layer and a light emitting layer, phosphorescence characteristics can be improved and color purity can be increased.

In particular, when the compound represented by Formula 1 is used in an organic electroluminescent device, its performance can be enhanced. That is, in the organic electroluminescent device, the light emitting layer is made of a host / dopant material. In order to efficiently transfer energy between the host and the dopant, the compound represented by Formula 1 is used as a host material in the light emitting layer, The organic electroluminescent device having excellent color purity as well as driving voltage, luminous efficiency and lifetime characteristics by using the compound represented by the general formula (3) as a dopant material of the light emitting layer can be provided.

In the compound of formula (3) of the present invention, X and Y are bonded to each other to form an organic ligand represented by XY, wherein X is a heteroaryl group having 3 to 40 nuclear atoms, preferably N- Containing heteroaryl group, and Y is a C ₆ to C ₄₀ aryl group or a heteroaryl group having 3 to 40 nuclear atoms.

The X and Y of the aryl group or heteroaryl group, halogen, a cyano group, an amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₂ ~ C of ₄₀ alkenyl, C alkynyl group of _{2 ~ C 40, C 1 ~} C 40 alkoxy group, C ₆ ~ C ₄₀ aryl group and a nuclear atoms least one member selected from the group consisting of a heteroaryl group of from 5 to 40 substituents . ≪ / RTI > The substituent may be bonded to an adjacent group to form a condensed ring or a spiro bond.

The compound represented by the formula (3) of the present invention is preferably selected from the group consisting of the compounds represented by the following formulas (3a) to (3d).

[Chemical Formula 3]

(3b)

[Chemical Formula 3c]

(3d)

In the above formulas (3a) to (3d), X, Y, n and R ₁₁ to R ₁₈ are the same as defined above.

Wherein Ra and R ₂₁ to R ₂₅ each independently represent hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ An arylsilyl group of C ₆ to C ₆₀ , a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ An arylphosphine oxide group and an arylamine group of C ₆ to C ₆₀ , and may form a condensed ring by combining with adjacent groups, and m is an integer of 0 to 3.

X-Y, which is an organic ligand in Formula 3, is preferably selected from the group consisting of the structures represented by the following Al-A24 in view of the characteristics of the organic electroluminescent device.

R ₃₁ to R ₄₂ in the structures represented by A 1 to A 24 each independently represent hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine pingi, is selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine, the combination adjacent groups may form a condensed ring.

Specific examples of the compound represented by the formula (3) of the present invention include, but are not limited to, the following compounds (1-170).

The compound represented by formula (1) and the compound represented by formula (3) of the present invention described above can be synthesized on the basis of the following synthesis examples.

Meanwhile, the organic electroluminescent device of the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, Can be made of materials and structures known in the art, except for including the compounds represented by formulas (1) and (3).

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

It is preferable that at least one of the hole injecting layer, the hole transporting layer, and the light emitting layer corresponding to the organic material layer includes the compound represented by the above formulas (1) and (3). More preferably, the compound represented by Formula 1 of the present invention may be used as a phosphorescent host of the light emitting layer and the compound represented by Formula 3 may be used as a phosphorescent dopant of the light emitting layer.

The substrate may be a silicon wafer, quartz or glass plate, a metal plate, a plastic film, or a sheet.

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 and polyaniline; Or carbon black may be used.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; A multilayer structure material such as LiF / Al or LiO ₂ / Al, or the like can be used.

In addition, the electron injection layer and the electron transport layer are not particularly limited as long as they are materials known in the art.

The method of manufacturing the organic electroluminescent device of the present invention is not particularly limited as long as it is a method known in the art, but the organic material layer may be formed by a vacuum evaporation method or a solution coating method. Examples of the solution coating method include a spin coating method, a dip coating method, a doctor blading method, an ink jet printing method, and a thermal transfer method.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[ Preparation Example  One] IC Synthesis of -1

≪ Step 1 > 5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indole Synthesis of

(25 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (48.58 g , 0.191 mol), mixed with _{Pd (dppf) Cl 2 (5.2} g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and 130 ℃ Lt; / RTI > for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indole (22.32 g, yield 72%).

¹ H-NMR:? 1.24 (s, 12H), 6.45 (d, IH), 7.27 (d, IH), 7.42 s, 1 H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) -1H- indole Synthesis of

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- g, 90.49 mmol), NaOH (9.05 g, 226.24 mmol) and THF / H ₂ O (400 ml / 200 ml) were mixed and Pd (PPh ₃ ) ₄ (4.36 g, 5 mol%) And the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1H-indole (11.32 g, yield 63%).

^{1 H-NMR: δ 6.47 (} d, 1H), 7.25 (d, 1H), 7.44 (d, 1H), 7.53 (d, 1H), 7.65 (t, 1H), 7.86 (t, 1H), 7.95 ( (s, 1 H), 8.00 (d, 1 H), 8.09 (t,

&Lt; Step 3 > 5- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

(11 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol) and K ₂ CO ₃ (6.38 g, 46.17 mmol), Na ₂ SO ₄ (6.56 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1- 71%).

^{1 H-NMR: δ 6.48 (} d, 1H), 7.26 (d, 1H), 7.45 (m, 3H), 7.55 (m, 4H), 7.63 (t, 1H), 7.84 (t, 1H), 7.93 ( s, 1 H), 8.01 (d, 1 H), 8.11 (t, 1 H)

<Step 4> IC Synthesis of -1

(5 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1,2-dichlorobenzene (50 ml) were mixed in a nitrogen gas stream for 12 hours Lt; / RTI &gt;

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-1 (2.38 g, yield 53%).

^{1 H-NMR: δ 6.99 (} d, 1H), 7.12 (t, 1H), 7.27 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.50 (d, 1H), 7.60 ( (d, IH), 8.05 (d, IH)

[ Preparation Example  2] IC Synthesis of -2

Step 4 of Preparation Example 1 was carried out using the above 5- (2-nitrophenyl) -1-phenyl-1H-indole, triphenylphosphine and 1,2-dichlorobenzene to obtain IC- -2.

^{1 H-NMR: δ 6.98 (} d, 1H), 7.13 (t, 1H), 7.26 (t, 1H), 7.33 (d, 1H), 7.42 (t, 1H), 7.51 (s, 1H), 7.61 ( (d, IH), 8.03 (s, IH), 10.58 (s, IH)

[ Preparation Example  3] IC Synthesis of -3

&Lt; Step 1 > 6- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 6-bromo-1H-indole was used instead of 5-bromo-1H-indole to obtain 6- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) -1H-indole.

¹ H-NMR:? 1.25 (s, 12H), 6.52 (d, IH), 7.16 (d, IH), 7.21 s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl ) -1H- indole Synthesis of

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole was used instead of 5- (4,4,5,5-tetramethyl- (2-nitrophenyl) -1H-indole was obtained in the same manner as in <Step 2> of Preparation Example 1 except that dioxaborolan-2-yl) -1H-indole was used.

^{1 H-NMR: δ 6.57 (} d, 1H), 7.07 (d, 1H), 7.24 (d, 1H), 7.35 (s, 1H), 7.43 (t, 1H), 7.50 (d, 1H), 7.58 ( t, 1 H), 7.66 (d, 1 H), 7.78 (d,

&Lt; Step 3 > 6- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

The procedure of Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1H- -nitrophenyl) -1-phenyl-1H-indole.

^{1 H-NMR: δ 6.81 (} d, 1H), 7.12 (t, 1H), 7.22 (t, 1H), 7.35 (s, 1H), 7.43 (d, 1H), 7.51 (m, 3H), 7.56 ( (m, 2H), 7.62 (m, 2H), 7.85 (d,

<Step 4> IC Synthesis of -3

Step 4 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) And IC-3 was obtained.

^{1 H-NMR: δ 6.80 (} d, 1H), 7.11 (t, 1H), 7.23 (t, 1H), 7.42 (d, 1H), 7.50 (m, 3H), 7.57 (m, 2H), 7.63 ( (m, 2H), 7.86 (d, 1H), 8.03 (d,

[ Preparation Example  4] IC Synthesis of -4

Step 4 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) To obtain IC-3 and the structural isomer IC-4.

^{1 H-NMR: δ 6.81 (} d, 1H), 7.12 (t, 1H), 7.22 (t, 1H), 7.43 (s, 1H), 7.51 (m, 3H), 7.58 (m, 2H), 7.64 ( (m, 2H), 7.85 (d, 1H), 8.02 (s,

[ Preparation Example  5] IC Synthesis of -5

<Step 1> Synthesis of 4- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 4-bromo-1H-indole was used instead of 5-bromo-1H-indole to obtain 4- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) -1H-indole.

^{1 H NMR: δ 1.26 (s} , 12H), 6.43 (d, 1H), 7.26 (t, 1H), 7.48 (d, 1H), 7.74 (d, 1H), 7.85 (d, 1H), 8.23 (s , 1H)

<Step 2> Synthesis of 4- (2- nitrophenyl ) -1H- indole Synthesis of

Instead of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H- dioxaborolan-2-yl) -1H-indole, the procedure of Step 2 of Preparation Example 1 was repeated to obtain 4- (2-nitrophenyl) -1H-indole.

^{1 H NMR: δ 6.45 (d} , 1H), 7.27 (t, 1H), 7.50 (d, 1H), 7.66 (t, 1H), 7.75 (d, 1H), 7.89 (m, 2H), 7.99 (d , &Lt; / RTI &gt; 1H), 8.04 (d, 1H), 8.24

<Step 3> Synthesis of 4- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

The procedure of Step 3 of Preparation Example 1 was repeated except that 4- (2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1H- nitrophenyl) -1-phenyl-1H-indole.

^{1 H NMR: δ 6.47 (d} , 1H), 7.28 (t, 1H), 7.47 (m, 2H), 7.52 (m, 2H), 7.60 (m, 2H), 7.67 (t, 1H), 7.75 (d , 7.89 (m, 2H), 8.00 (d, IH), 8.06 (d, IH)

<Step 4> IC Synthesis of -5

Step 4 of Preparation Example 1 was repeated except that 4- (2-nitrophenyl) -1-phenyl-1H-indole was used in place of 5- (2-nitrophenyl) To obtain IC-5.

^{1 H NMR: δ 6.49 (d} , 1H), 7.29 (t, 1H), 7.46 (m, 2H), 7.54 (m, 2H), 7.61 (d, 1H), 7.69 (t, 1H), 7.74 (d , 8.01 (d, IH), 8.04 (d, IH), 8.23 (s, IH)

[ Preparation Example  6] IC Synthesis of -6

&Lt; Step 1 > 7- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 7-bromo-1H-indole was used instead of 5-bromo-1H-indole to obtain 7- (4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl) -1H-indole.

^{1 H NMR: δ 1.25 (s} , 12H), 6.43 (d, 1H), 7.25 (d, 1H), 7.45 (t, 1H), 7.56 (d, 1H), 7.71 (d, 1H), 8.22 (s , 1H)

&Lt; Step 2 > 7- (2- nitrophenyl ) -1H- indole Synthesis of

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole was used instead of 5- (4,4,5,5-tetramethyl- (2-nitrophenyl) -1H-indole was obtained in the same manner as in <Step 2> of Preparation Example 1 except that dioxaborolan-2-yl) -1H-indole was used.

^{1 H NMR: δ 6.42 (d} , 1H), 7.24 (d, 1H), 7.43 (t, 1H), 7.55 (d, 1H), 7.70 (m, 2H), 7.88 (t, 1H), 8.01 (d , 8.11 (d, 1 H), 8.23 (s, 1 H)

&Lt; Step 3 > 7- (2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

The procedure of Step 3 of Preparation Example 1 was repeated except that 7- (2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1H- nitrophenyl) -1-phenyl-1H-indole.

^{1 H NMR: δ 6.43 (d} , 1H), 7.26 (d, 1H), 7.44 (m, 3H), 7.56 (m, 4H), 7.71 (m, 2H), 7.89 (t, 1H), 8.02 (d , &Lt; / RTI &gt; 1H), 8.10 (d, 1H)

<Step 4> IC Synthesis of -6

Step 4 of Preparation Example 1 was repeated except that 7- (2-nitrophenyl) -1-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) To obtain IC-6.

^{1 H NMR: δ 6.45 (d} , 1H), 7.24 (d, 1H), 7.45 (m, 3H), 7.57 (m, 3H), 7.63 (d, 1H), 7.70 (d, 1H), 7.88 (t , 8.00 (d, IH), 8.09 (d, IH), 8.22 (s, IH)

[ Preparation Example  7] IC Synthesis of -7

<Step 1> 5- (5- bromo -2- nitrophenyl ) -1H- indole Synthesis of

5-bromo-2-nitrophenyl) -methanone was obtained in the same manner as in <Step 2> of Preparation Example 1 except that 2,4-dibromo-1-nitrobenzene was used instead of 1-bromo- 1H-indole.

^{1 H NMR: δ 6.45 (d} , 1H), 7.26 (d, 1H), 7.45 (d, 1H), 7.55 (d, 1H), 7.64 (d, 1H), 7.85 (d, 1H), 7.96 (s , &Lt; / RTI &gt; 1H), 8.13 (s, 1H), 8.21

&Lt; Step 2 > 5- (5- bromo -2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

The procedure of Step 3 of Preparation Example 1 was repeated except that 5- (5-bromo-2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) - (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole.

^{1 H NMR: δ 6.44 (d} , 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 4H), 7.65 (d, 1H), 7.86 (d, 1H), 7.95 (s , &Lt; / RTI &gt; 1H), 8.11 (s, 1H)

<Step 3> IC Synthesis of -7

Step 4 of Preparation Example 1 was repeated except that 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) Gt; IC-7 < / RTI > was obtained.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.26 (d, 1H), 7.38 (m, 2H), 7.45 (d, 1H), 7.51 (d, 1H), 7.57 (m, 3H), 7.64 ( (d, IH), 7.85 (d, IH), 8.10 (s, IH), 8.23

[ Preparation Example  8] IC Synthesis of -8

<Step 1> 6- (5- bromo -2- nitrophenyl ) -1H- indole Synthesis of

1-nitrobenzene and 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H- indole instead of 1-bromo- Step 2 of Preparation Example 1 was repeated except that 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole was used instead of 4- (5-bromo-2-nitrophenyl) -1H-indole.

^{1 H NMR: δ 6.51 (d} , 1H), 7.31 (d, 1H), 7.50 (d, 1H), 7.60 (d, 1H), 7.69 (d, 1H), 7.90 (d, 1H), 8.01 (s , &Lt; / RTI &gt; 1H), 8.14 (s, 1H), 8.25

&Lt; Step 2 > 6- (5- bromo -2- nitrophenyl )-One- phenyl -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 6- (5-bromo-2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) - (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole.

^{1 H NMR: δ 6.49 (d} , 1H), 7.30 (d, 1H), 7.51 (m, 3H), 7.61 (m, 4H), 7.70 (d, 1H), 7.91 (d, 1H), 8.00 (s , &Lt; / RTI &gt; 1H), 8.16 (s, 1H)

<Step 3> IC Synthesis of -8

Step 4 of Preparation Example 1 was repeated except that 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole was used in place of 5- (2-nitrophenyl) Gt; IC-8 < / RTI > was obtained.

^{1 H-NMR: δ 6.47 (} d, 1H), 7.28 (d, 1H), 7.40 (m, 2H), 7.47 (d, 1H), 7.53 (d, 1H), 7.59 (m, 3H), 7.66 ( (d, IH), 7.87 (d, IH), 8.12 (s, IH), 8.25

[ Preparation Example  9] IC Synthesis of -9

<Step 1> 5- (2- nitrophenyl ) -1-o- tolyl -1H- indole Synthesis of

5- (2-nitrophenyl) -1-o-tolyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1, except that 1-bromo-2-methylbenzene was used instead of iodobenzene.

^{1 H-NMR: δ 1.92 (} s, 3H), 6.47 (d, 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 3H), 7.64 (t, 1H), 7.85 ( t, 1 H), 7.94 (s, 1 H), 8.00 (d,

<Step 2> IC - 9 of  synthesis

Step 4 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) -1-o-tolyl-1H-indole was used instead of 5- (2-nitrophenyl) The same procedure was followed to obtain IC-9.

^{1 H-NMR: δ 1.93 (} s, 3H), 6.98 (d, 1H), 7.11 (t, 1H), 7.28 (t, 1H), 7.31 (d, 1H), 7.42 (t, 1H), 7.51 ( (d, IH), 7.61 (m, 4H), 7.86 (d,

[ Preparation Example  10] IC Synthesis of -10

<Step 1> 1- ( biphenyl -4- yl ) -5- (2- nitrophenyl ) -1H- indole Synthesis of

(Biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1 except that 4-bromobiphenyl was used in place of iodobenzene.

^{1 H-NMR: δ 6.73 (} d, 1H), 7.18 (d, 1H), 7.39 (m, 2H), 7.47 (m, 3H), 7.54 (d, 1H), 7.59 (m, 3H), 7.64 ( m, 4H), 7.75 (d, 2H), 7.82 (d, IH)

<Step 2> IC Synthesis of -10

Except that the 1- (biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole was used in place of 5- (2-nitrophenyl) Step 4 &gt; to obtain IC-10.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.20 (d, 1H), 7.42 (m, 2H), 7.51 (m, 3H), 7.56 (d, 1H), 7.62 (m, 3H), 7.68 ( (d, 2H), 7.85 (d, 1H), 10.45 (s, 1H)

[ Preparation Example  11] IC Synthesis of -11

<Step 1> IC Synthesis of -11-1

IC-11-1 was obtained in the same manner as in <Step 3> of Preparation Example 1 except that 1-bromo-3,5-diphenyl benzene was used in place of iodobenzene.

^{1 H-NMR: δ 6.98 (} d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (t, 2H), 7.46 (m, 6H), 7.58 (d, 1H), 7.81 ( (d, IH), 7.87 (m, 4H), 7.93

<Step 2> IC Synthesis of -11

IC-11 was obtained in the same manner as in <Step 4> of Preparation Example 1 except that IC-11-1 was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole.

^{1 H-NMR: δ 6.97 (} d, 1H), 7.10 (t, 1H), 7.23 (t, 1H), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, 1H), 7.80 ( (d, IH), 7.86 (d, IH), 7.86 (d,

[ Preparation Example  12] IC Synthesis of -12

<Step 1> 5- (2- nitrophenyl ) -1- (2- ( trifluoromethyl ) phenyl ) -1H- indole Synthesis of

(2-nitrophenyl) -1- (2- trifluoromethyl) benzene was prepared by following the procedure of Step 3 of Preparation Example 1, except that 1-bromo-2- (trifluoromethyl) benzene was used in place of iodobenzene. ) -1H-indole.

¹ H-NMR:? 6.48 (d, IH), 7.26 (d, IH), 7.47 (m, 3H), 7.57 s, 1 H), 8.01 (d, 1 H), 8.13 (t, 1 H)

<Step 2> IC Synthesis of -12

Except that the 5- (2-nitrophenyl) -1- (2- (trifluoromethyl) phenyl) -1H-indole was used in place of 5- (2-nitrophenyl) IC-12 was obtained by performing the same procedure as in < Step 4 >.

^{1 H-NMR: δ 6.97 (} d, 1H), 7.12 (t, 1H), 7.29 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.52 (d, 1H), 7.60 ( (s, 1H), 7.85 (d, 1H), 8.01 (d,

[ Preparation Example  13] IC Synthesis of -13

<Step 1> 1- ( biphenyl -3- yl ) -5- (2- nitrophenyl ) -1H- indole Synthesis of

(Biphenyl-3-yl) -5- (2-nitrophenyl) -1H-indole was obtained in the same manner as in <Step 3> of Preparation Example 1 except that 3-bromobiphenyl was used instead of iodobenzene.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.19 (d, 1H), 7.38 (m, 2H), 7.48 (m, 3H), 7.52 (d, 1H), 7.58 (m, 3H), 7.65 ( m, 4H), 7.76 (m, 2H), 7.85 (d, IH)

<Step 2> IC Synthesis of -13

Except that the 1- (biphenyl-3-yl) -5- (2-nitrophenyl) -1H-indole was used in place of 5- (2-nitrophenyl) Step 4 &gt; to obtain IC-13.

^{1 H-NMR: δ 6.74 (} d, 1H), 7.21 (d, 1H), 7.41 (m, 2H), 7.52 (m, 3H), 7.56 (d, 1H), 7.61 (m, 3H), 7.69 ( m, 3H), 7.77 (m, 2H), 7.86 (d,

[ Preparation Example  14] IC Synthesis of -14

<Step 1> 1- ( biphenyl -3- yl ) -6- (2- nitrophenyl ) -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-indole and 3-bromobiphenyl were used instead of 5- (2-nitrophenyl) -1H-indole and iodobenzene To obtain 1- (biphenyl-3-yl) -6- (2-nitrophenyl) -1H-indole.

^{1 H-NMR: δ 6.76 (} d, 1H), 7.18 (d, 1H), 7.37 (m, 2H), 7.47 (m, 3H), 7.51 (d, 1H), 7.57 (m, 3H), 7.64 ( m, 4H), 7.75 (m, 2H), 7.86 (d, IH)

<Step 2> IC Synthesis of -14

Except that the 1- (biphenyl-3-yl) -6- (2-nitrophenyl) -1H-indole was used in place of 5- (2-nitrophenyl) IC-14 was obtained by performing the same procedure as in < Step 4 >.

^{1 H-NMR: δ 6.75 (} d, 1H), 7.20 (d, 1H), 7.40 (m, 2H), 7.51 (m, 3H), 7.57 (d, 1H), 7.62 (m, 3H), 7.70 ( (s, 3H), 7.76 (m, 2H), 7.85 (d,

[ Preparation Example  15] IC Synthesis of -15

<Step 1> 1- ( biphenyl -4- yl ) -6- (2- nitrophenyl ) -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-indole and 4-bromobiphenyl were used instead of 5- (2-nitrophenyl) -1H- indole and iodobenzene To obtain 1- (biphenyl-4-yl) -6- (2-nitrophenyl) -1H-indole.

^{1 H-NMR: δ 6.74 (} d, 1H), 7.19 (d, 1H), 7.40 (m, 2H), 7.46 (m, 3H), 7.55 (d, 1H), 7.58 (m, 3H), 7.63 ( m, 4H), 7.75 (d, 2H), 7.83 (d, IH)

<Step 2> IC Synthesis of -15

Except that the 1- (biphenyl-4-yl) -6- (2-nitrophenyl) -1H-indole was used in place of 5- (2-nitrophenyl) &Lt; Step 4 > was performed to obtain IC-15.

^{1 H-NMR: δ 6.74 (} d, 1H), 7.19 (d, 1H), 7.43 (m, 2H), 7.52 (m, 3H), 7.57 (d, 1H), 7.63 (m, 3H), 7.69 ( (m, 3H), 7.75 (d, 2H), 7.86 (d,

[ Preparation Example  16] IC Synthesis of -16

<Step 1> IC Synthesis of -16-1

Except that 6- (2-nitrophenyl) -1H-indole and 1-bromo-3,5-diphenyl benzene were used in place of iodobenzene and 5- (2-nitrophenyl) IC-16-1 < / RTI > was obtained in the same manner as in &lt; Step 3 &gt;

^{1 H-NMR: δ 6.98 (} d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (m, 2H), 7.45 (m, 6H), 7.57 (d, 1H), 7.80 ( (d, IH), 7.86 (m, 4H), 7.92

<Step 2> IC Synthesis of -16

IC-16 was obtained in the same manner as in <Step 4> of Preparation Example 1 except that IC-16-1 was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole.

^{1 H-NMR: δ 6.97 (} d, 1H), 7.10 (t, 1H), 7.23 (t, 1H), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, 1H), 7.80 ( (d, IH), 7.86 (d, IH), 7.86 (m,

[ Preparation Example  17] IC Synthesis of -17

&Lt; Step 1 > 6- (2- nitrophenyl ) -1- (3- ( trifluoromethyl ) phenyl ) -1H- indole Synthesis of

Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-indole and 1-bromo-3- (trifluoromethyl) benzene were used in place of iodobenzene and 5- (2-nitrophenyl) (2-nitrophenyl) -1- (3- (trifluoromethyl) phenyl) -1H-indole was obtained in the same manner as in <Step 3>.

^{1 H-NMR: δ 6.80 (} d, 1H), 7.11 (t, 1H), 7.21 (t, 1H), 7.36 (s, 1H), 7.42 (s, 1H), 7.50 (m, 2H), 7.55 ( (m, 2H), 7.63 (m, 2H), 7.86 (d,

<Step 2> IC Synthesis of -17

Except that the 6- (2-nitrophenyl) -1- (3- (trifluoromethyl) phenyl) -1H-indole was used in place of 5- (2-nitrophenyl) IC-17 < / RTI > was obtained in the same manner as in &lt; Step 4 &gt;

^{1 H-NMR: δ 6.81 (} d, 1H), 7.12 (t, 1H), 7.24 (t, 1H), 7.43 (d, 1H), 7.51 (m, 2H), 7.58 (m, 2H), 7.64 ( (m, 2H), 7.85 (d, 1H), 8.02 (d,

[ Preparation Example  18] IC Synthesis of -18

<Step 1> Synthesis of 3- (5- (2- nitrophenyl ) -1H- indole -One- yl ) -9- phenyl -9H- carbazole Synthesis of

Except that 6- (2-nitrophenyl) -1H-indole and 3-bromo-9-phenyl-9H-carbazole were used instead of 5- (2-nitrophenyl) -1H- indole and Iodobenzene. 3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9-phenyl-9H-carbazole was obtained.

GC-Mass (calculated: 479.16 g / mol, measured: 479 g / mol)

<Step 2> IC Synthesis of -18

Except that the above 3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9-phenyl-9H-carbazole was used instead of 5- (2-nitrophenyl) IC-18 was obtained in the same manner as in <Step 4> of Preparation Example 1 above.

GC-Mass (calculated: 447.17 g / mol, measured: 447 g / mol)

[ Preparation Example  19] IC -19 Synthesis

&Lt; Step 1 > 9- (4,6- 피덴 -1,3,5- triazin -2- yl ) -3- (5- (2- nitrophenyl ) -1H-indol-1-yl) -9H-carbazole

(2-nitrophenyl) -1H-indole and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2- yl ) -9H-carbazole, the procedure of Step 3 of Preparation Example 1 was repeated to give 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9H-carbazole.

GC-Mass (calculated: 634.21 g / mol, measured: 634 g / mol)

&Lt; Step 2 > 3- (9- (4,6- 피덴 -1,3,5- triazin -2- yl ) -9H- carbazole -3- yl ) -3,10-dihydropyrrolo [3,2-a] carbazole

(2-nitrophenyl) -1-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) 1H-indol-1-yl) -9H-carbazole, IC-19 was obtained in the same manner as in <Step 4> of Preparation Example 1 above.

GC-Mass (theory: 602.22 g / mol, measured: 602 g / mol)

[ Preparation Example  20] IC Synthesis of -20

<Step 1> 5- bromo -2- phenyl -1H- indole Synthesis of

Pd (OAc) ₂ (1.43 g, 5 mol%), Triphenylphosphine (1.67 g, 5 mol%) was added to a solution of 5-bromo-1H- indole (25 g, 0.13 mol), Iodobenzene (31.22 g, 0.15 mol) , KOAc (37.55 g, 0.38 mol) and H ₂ O (300 ml) were mixed and stirred at 110 ° C for 24 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5-bromo-2-phenyl- 16.66 g, yield: 48%).

^{1 H-NMR: δ 6.89 (} dd, 1H), 7.20 (dd, 1H), 7.34 (m, 1H), 7.36 (d, 1H), 7.47 (t, 2H), 7.71 (d, 1H), 7.86 ( dd, 2 H), 11.74 (s, 1 H)

<Step 2> Synthesis of 5- (2- nitrophenyl )-2- phenyl -1H- indole Synthesis of

2-phenyl-1H-indole (15 g, 55.12 mmol), NaOH (6.61 g, 165.36 mmol), and THF / H ₂ O (10 mL) were added to a solution of 2-nitrophenylboronic acid (11.04 g, 66.14 mmol) a mixture of 200 ml / 100 ml), and then, Pd (PPh ₃₎ at 40 ℃ into the ₄ (3.18 g, 5 mol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. 2-Nitrophenyl-2-phenyl-1H-indole (10.74 g, yield 62%) was obtained after purification by column chromatography (Hexane: EA = 5: 1 (v / v) &Lt; / RTI &gt;

^{1 H-NMR: δ 6.88 (} dd, 1H), 7.21 (d, 1H), 7.32 (m, 1H), 7.34 (d, 1H), 7.46 (m, 3H), 7.64 (m, 2H), 7.77 ( d, 2H), 8.02 (d, 2H), 11.73 (s, 1H)

&Lt; Step 3 > 5- (2- nitrophenyl ) -1,2- 피덴 -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) -2-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) - (2-nitrophenyl) -1,2-diphenyl-1H-indole.

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

<Step 4> IC Synthesis of -20

Step 4 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) -1,2-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) And IC-20 was obtained.

GC-Mass (358.15 g / mol, measured: 358 g / mol)

[ Preparation Example  21] IC Synthesis of -21

<Step 1> 6- chloro -2- phenyl -1H- indole Synthesis of

1H-indole and 6-chloro-1H-indole and bromobenzene were used in place of 5-bromo-1H-indole and Iodobenzene to obtain 6-chloro-2-phenyl-1H -indole.

^{1 H-NMR: δ 6.92 (} d, 1H), 7.02 (dd, 1H), 7.33 (t, 1H), 7.41 (s, 1H), 7.47 (t, 2H), 7.54 (d, 1H), 7.85 ( d, 2 H), 11.68 (s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl )-2- phenyl -1H- indole Synthesis of

Step 2 of Preparation Example 20 was repeated except that 6-chloro-2-phenyl-1H-indole was used in place of 5-bromo-2-phenyl-1H- -nitrophenyl) -2-phenyl-1H-indole.

^{1 H-NMR: δ 6.91 (} d, 1H), 7.03 (d, 1H), 7.31 (t, 1H), 7.42 (s, 1H), 7.48 (m, 3H), 7.53 (d, 1H), 7.76 ( m, 3H), 8.01 (d, 2H), 11.66 (s, IH)

&Lt; Step 3 > 6- (2- nitrophenyl ) -1,2- 피덴 -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -2-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) - (2-nitrophenyl) -1,2-diphenyl-1H-indole.

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

<Step 4> Synthesis of 6- (2- nitrophenyl ) -1,2- 피덴 -1H- indole Synthesis of

Step 4 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1,2-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) And IC-21 was obtained.

GC-Mass (358.15 g / mol, measured: 358 g / mol)

[ Preparation Example  22] IC Synthesis of -22

<Step 1> 6- chloro -3- phenyl -1H- indole Synthesis of

Pd (OAc) ₂ (1.86 g, 5 moles), triphenylphosphine (2.17 g, 5 mol%), bromobenzene (31.19 g, 0.20 mol) K ₂ CO ₃ (68.64 g, 0.50 mol) and 1,4-dioxane (300 ml) were mixed and stirred at 130 ° C for 18 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 6-chloro-3-phenyl- 24.5 g, yield 65%).

^{1 H-NMR: δ 7.10 (} dd, 1H), 7.25 (m, 1H), 7.43 (t, 2H), 7.49 (d, 1H), 7.67 (dd, 2H), 7.73 (d, 1H), 7.85 ( d, 1 H), 11.49 (s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl ) -3- phenyl -1H- indole Synthesis of

The procedure of Step 2 of Preparation Example 20 was repeated except that 6-chloro-3-phenyl-1H-indole was used in place of 5-bromo-2-phenyl- -nitrophenyl) -3-phenyl-1H-indole.

^{1 H-NMR: δ 7.11 (} d, 1H), 7.26 (m, 1H), 7.44 (t, 2H), 7.48 (m, 2H), 7.55 (m, 3H), 7.61 (d, 1H), 7.73 ( d, 1 H), 8.00 (d, 2H), 11.48 (s, 1 H)

&Lt; Step 3 > 6- (2- nitrophenyl ) -1,3- 피덴 -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -3-phenyl-1H-indole was used instead of 5- (2-nitrophenyl) - (2-nitrophenyl) -1,3-diphenyl-1H-indole.

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

<Step 4> Synthesis of 6- (2- nitrophenyl ) -1,3- 피덴 -1H- indole Synthesis of

Step 4 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1,3-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) And IC-21 was obtained.

GC-Mass (358.15 g / mol, measured: 358 g / mol)

[ Preparation Example  23] IC Synthesis of -23

<Step 1> 5- bromo -2,3- 피덴 -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 22 was followed except that 5-bromo-2-phenyl-1H-indole was used instead of 6-chloro-1H-indole to obtain 5-bromo-2,3-diphenyl -1H-indole.

^{1 H-NMR: δ 7.23 (} d, 1H), 7.31 (t, 2H), 7.43 (m, 6H), 7.67 (d, 1H), 7.71 (d, 1H), 7.84 (d, 2H), 11.34 ( s, 1 H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) -2,3- 피덴 -1H- indole Synthesis of

The procedure of Step 2 of Preparation Example 20 was repeated except that 5-bromo-2,3-diphenyl-1H-indole was used instead of 5-bromo-2-phenyl- (2-nitrophenyl) -2,3-diphenyl-1H-indole.

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

&Lt; Step 3 > 5- (2- nitrophenyl ) -1,2,3- 트리 피닐 -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) -2,3-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) To obtain 5- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole.

GC-Mass (calculated: 466.17 g / mol, measured: 466 g / mol)

<Step 4> IC Synthesis of -23

Except that 5- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was used in place of 5- (2-nitrophenyl) -1- 4 &gt; to obtain IC-23.

GC-Mass (calculated: 434.18 g / mol, measured: 434 g / mol)

[ Preparation Example  24] IC Synthesis of -24

<Step 1> 6- chloro -2,3- 피덴 -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 22 was repeated except that 6-chloro-2-phenyl-1H-indole was used instead of 6-chloro-1H-indole to obtain 6-chloro-2,3- -1H-indole.

^{1 H-NMR: δ 7.18 (} d, 1H), 7.29 (t, 2H), 7.50 (m, 6H), 7.62 (d, 1H), 7.75 (d, 1H), 7.89 (d, 2H), 11.35 ( s, 1 H)

&Lt; Step 2 > 6- (2- nitrophenyl ) -2,3- 피덴 -1H- indole Synthesis of

The procedure of Step 2 of Preparation Example 20 was repeated except that 6-chloro-2,3-diphenyl-1H-indole was used instead of 5-bromo-2-phenyl- (2-nitrophenyl) -2,3-diphenyl-1H-indole.

GC-Mass (theory: 390.14 g / mol, measured: 390 g / mol)

&Lt; Step 3 > 6- (2- nitrophenyl ) -1,2,3- 트리 피닐 -1H- indole Synthesis of

Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -2,3-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) To obtain 6- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole.

GC-Mass (calculated: 466.17 g / mol, measured: 466 g / mol)

<Step 4> IC Synthesis of -24

Except that 6- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was used in place of 5- (2-nitrophenyl) -1- 4 &gt; to obtain IC-24.

GC-Mass (calculated: 434.18 g / mol, measured: 434 g / mol)

[ Preparation Example  25] IC Synthesis of -25

&Lt; Step 1 > 1- (3- (4,6- 피덴 -1,3,5- triazin -2- yl ) phenyl ) -6- (2-nitrophenyl) -1H-indole

(10 g, 41.97 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (17.32 g, 50.37 mmol) in a nitrogen atmosphere. , P (t-bu) ₃ (0.85 g, 4.19 mmol) and Toluene (100 ml) were added to a solution of Pd (OAc) ₂ (0.47 g, 5 mol%), NaO And the mixture was stirred at 110 DEG C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 1- (3- (4- 1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole (15.8 g, yield 69%).

GC-Mass (calculated: 545.19 g / mol, measured: 545 g / mol)

<Step 2> IC Synthesis of -25

Phenyl-6- (2-nitrophenyl) -1- phenyl-1H-indole in place of 5- (2-nitrophenyl) ) -1H-indole was used in place of IC-25, IC-25 was obtained in the same manner as in <Step 4> of Preparation Example 1 above.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[ Preparation Example  26] IC Synthesis of -26

&Lt; Step 1 > 1- (3- (4,6- diphenylpyrimidine -2- yl ) phenyl ) -6- (2- nitrophenyl ) -1H-indole &lt; / RTI &gt;

Except that 2- (3-chloro phenyl) -4,6-diphenylpyrimidine was used in place of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- 1 -> was carried out to obtain 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole.

GC-Mass (calculated: 544.19 g / mol, measured: 544 g / mol)

<Step 2> IC Synthesis of -26

(2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl- IC-26 was obtained in the same manner as in <Step 4> of Preparation Example 1 except for the following.

GC-Mass (calculated: 512.20 g / mol, measured: 512 g / mol)

[ Preparation Example  27] IC -27

&Lt; Step 1 > 1- (3- (4,6- 피덴 -1,3,5- triazin -2- yl ) phenyl ) -5- (2-nitrophenyl) -1H-indole &lt; / RTI &gt;

The procedure of Step 1 of Preparation Example 25 was repeated except that 5- (2-nitrophenyl) -1H-indole was used instead of 6- (2-nitrophenyl) -1H- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitro phenyl) -1H-indole.

GC-Mass (calculated: 545.19 g / mol, measured: 545 g / mol)

<Step 2> IC -27

(3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) - phenylalanine obtained in the above Step 1 was used instead of 5- (2-nitrophenyl) IC-27 was obtained in the same manner as in <Step 4> of Preparation Example 1 except that 5- (2-nitro phenyl) -1H-indole was used.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[ Preparation Example  28] IC -28 Synthesis

&Lt; Step 1 > 1- (3- (4,6- diphenylpyrimidine -2- yl ) phenyl ) -5- (2- nitrophenyl ) -1H-indole &lt; / RTI &gt;

(2-nitrophenyl) -1H-indole and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- (4,6-diphenylpyrimidin-2-yl) phenyl) -4,6-diphenylpyrimidine was used in the same manner as in <Step 1> of Preparation Example 25, -5- (2-nitrophenyl) -1H-indole.

GC-Mass (calculated: 544.19 g / mol, measured: 544 g / mol)

<Step 2> IC -28 Synthesis

Phenyl-5- (2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl- IC-28 was obtained in the same manner as in < Step 4 >

GC-Mass (calculated: 512.20 g / mol, measured: 512 g / mol)

[ Preparation Example  29] IC -29a and IC Synthesis of -29b

<Step 1> 2- ( benzo [b] thiophen-5- yl ) -4,4,5,5- tetramethyl -1,3,2-dioxaborolane

(Benzo [b] thiophen-5-yl) - (4-fluorophenyl) -lH-indole was obtained in the same manner as in <Step 1> of Preparation Example 1 except that 5-bromobenzo [b] thiophene was used instead of 5-bromo- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

¹ H NMR: 8 1.24 (s, 12H), 7.65 (d, IH), 7.85 (d, IH), 7.98

<Step 2> Synthesis of 5- (2- nitrophenyl ) benzo [b] thiophene Synthesis of

(Benzo [b] thiophen-5-yl) -4,4,5-thiophene instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- , 2-nitrophenyl benzo [b] thiophene was obtained in the same manner as in <Step 2> of Preparation Example 1 except that 5-tetramethyl-1,3,2-dioxaborolane was used.

¹ H NMR: 8 7.67 (m, 2H), 7.88 (m, 2H), 7.98 (d,

<Step 3> IC -29a and IC Synthesis of -29b

Step 4 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) benzo [b] thiophene was used instead of 5- (2-nitrophenyl) -1- 1.70 g (7.60 mmol, yield: 35%) of IC-29a and 1.89 g (8.46 mmol, yield: 39%) of IC-29b were obtained.

¹ H-NMR of the IC-29a: δ 7.29 (t , 1H), 7.59 (m, 3H), 7.79 (m, 3H), 8.11 (d, 1H), 8.26 (s, 1H)

¹ H-NMR of the IC-29b: δ 7.29 (t , 1H), 7.53 (m, 2H), 7.81 (m, 3H), 8.12 (m, 2H), 8.25 (s, 1H)

[ Preparation Example  30] IC - Thirty  synthesis

&Lt; Step 1 > 7- (2- nitrophenyl ) benzo [b] thiophene Synthesis of

To a solution of 12.2 g (35.2 mmol) of 7-bromobenzo [b] thiophene, 6.44 g (38.7 mmol) of 2-nitrophenylboronic acid, 4.22 g (105.6 mmol) of NaOH and 300 ml / 150 ml of THF / H ₂ O And the mixture was stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 2.03 g (5 mol%) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 7.38 g (28.9 mmol, yield 82%) of 7- (2-nitrophenyl) benzo [b] thiophene was obtained by column chromatography.

^{1 H-NMR: δ 7.63 (} m, 5H), 7.96 (m, 3H), 8.21 (d, 1H)

<Step 2> IC - Thirty  synthesis

5.53 g (21.7 mmol) of 7- (2-nitrophenyl) benzo [b] thiophene, 14.2 g (54.2 mmol) of triphenylphosphine and 100 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and 3.29 g (14.8 mmol, yield: 68%) of IC-30 was obtained by column chromatography.

^{1 H-NMR: δ 7.37 (} t, 1H), 7.46 (m, 5H), 7.87 (d, 1H), 8.20 (d, 1H), 8.24 (s, 1H)

[ Preparation Example  31] IC -31a and IC Synthesis of -31b

&Lt; Step 1 > 6- (2- nitrophenyl ) benzo [b] thiophene Synthesis of

The procedure of Step 1 of Preparation Example 30 was repeated except for using 12.2 g (35.2 mmol) of 6-bromobenzo [b] thiophene instead of 7-bromobenzo [b] thiophene to obtain 6- (2-nitrophenyl) benzo [b] thiophene (7.01 g, 27.5 mmol, yield: 78%).

^{1 H-NMR: δ 7.68 (} m, 3H), 7.98 (m, 6H)

<Step 2> IC -31a and IC Synthesis of -31b

Step 2 of Preparation Example 30 was repeated except that 5.53 g (21.7 mmol) of 6- (2-nitrophenyl) benzo [b] thiophene was used instead of 7- (2-nitrophenyl) benzo [ To obtain 1.60 g (7.16 mmol, yield: 33%) of IC-31a and 1.79 g (8.03 mmol, yield: 37%) of IC-31b.

The ^{IC-31a 1 H-NMR:} δ 7.27 (t, 1H), 7.53 (m, 4H), 7.78 (d, 1H), 7.92 (d, 1H), 8.10 (d, 1H), 8.25 (s, 1H )

¹ H-NMR of the IC-31b: δ 7.29 (t , 1H), 7.63 (m, 3H), 7.79 (m, 3H), 8.11 (d, 1H), 8.25 (s, 1H)

[ Preparation Example  32] IC Synthesis of -32

<Step 1> Synthesis of 4- (2- nitrophenyl ) benzo [b] thiophene Synthesis of

Step 2 was carried out in the same manner as in Step 1 of Preparation Example 30 except that 12.2 g (35.2 mmol) of 4-bromobenzo [b] thiophene was used instead of 7-bromobenzo [b] thiophene to obtain 4- (2-nitrophenyl) benzo 7.28 g (28.5 mmol, yield: 81%) of [b] thiophene was obtained.

^{1 H-NMR: δ 7.68 (} m, 4H), 7.89 (m, 3H), 8.01 (m, 2H)

<Step 2> IC - 32  synthesis

Step 2 of Preparation Example 30 was repeated except that 5.53 g (21.7 mmol) of 4- (2-nitrophenyl) benzo [b] thiophene was used instead of 7- (2-nitrophenyl) benzo [ To obtain 3.05 g (13.7 mmol, yield: 63%) of IC-32.

¹ H-NMR:? 7.31 (m, 2H), 7.73 (m, 4H), 7.96 (d,

[ Preparation Example  33] IC Synthesis of -33

<Step 1> Synthesis of 4- (2- isopropylphenyl ) -1H- indole Synthesis of

Instead of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -1H-indole and that 1-bromo-2-isopropylbenzene was used instead of 1-bromo-2-nitrobenzene, the procedure of Step 2 of Preparation Example 1 was repeated to obtain 4- (2-isopropylphenyl) -1H-indole.

^{1 H NMR: δ 1.21 (s} , 6H), 2.87 (m, 1H), 6.43 (d, 1H), 7.26 (t, 1H), 7.35 (m, 3H), 7.48 (d, 1H), 7.74 (m , 2H), 7.85 (d, 1 H), 8.23 (s, 1 H)

<Step 2> IC Synthesis of -33

Under nitrogen gas stream, the 4- (2-isopropylphenyl) -1H- indole (5 g, 21.25 mmol) and RhCl (PPh _{3) 3} was dissolved in a 1,4-dioxane 50 ml (98.3 mg , 0.5 mol%) , and then 135 ℃ Lt; / RTI &gt; for 1 hour.

After completion of the reaction, the solvent was removed and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v: v)) to obtain IC-33 (4 g, yield 81%).

¹ H NMR:? 1.20 (s, 6H), 6.45 (d, IH), 7.25 (d, IH), 7.37 , &Lt; / RTI &gt; 1H), 8.22 (s, 1H)

[ Preparation Example  34] IC Synthesis of -34

<Step 1> Synthesis of 4- (2- benzhydrylphenyl ) -1H- indole Synthesis of

Instead of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -1H-indole and that (2-bromophenyl) methylene) dibenzene was used instead of 1-bromo-2-nitrobenzene, the procedure of Step 2 of Preparation Example 1 was repeated to obtain 4 - (2-benzhydrylphenyl) -1H-indole.

^{1 H NMR: δ 2.88 (m} , 1H), 6.44 (d, 1H), 7.27 (m, 6H), 7.34 (m, 8H), 7.47 (d, 1H), 7.75 (m, 2H), 7.86 (d , &Lt; / RTI &gt; 1H), 8.21 (s, 1H)

<Step 2> IC Synthesis of -34

The procedure of Step 2 of Preparation Example 33 was followed except that 4- (2-benzhydrylphenyl) -1H-indole was used instead of 4- (2-isopropylphenyl) -1H-indole to obtain IC-34.

^{1 H NMR: δ 6.43 (d} , 1H), 7.26 (m, 5H), 7.34 (m, 8H), 7.46 (d, 1H), 7.76 (m, 2H), 7.85 (d, 1H), 8.20 (s , 1H)

[ Preparation Example  35] IC - Thirty-five  synthesis

&Lt; Step 1 > 6- (2- bromophenyl ) -7- chloro -1H- indole Synthesis of

Bromo-7-chloro-1H-indole, 9.54 g (47.5 mmol) of 2-bromophenylboronic acid, 4.75 g (118.8 mmol) of NaOH and 200 ml / 100 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 2.29 g (5 mol%) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 8.86 g (28.9 mmol, yield: 73%) of 6- (2-bromophenyl) -7-chloro-1H- indole was obtained by column chromatography.

¹ H-NMR:? 6.45 (d, 1 H), 7.35 (m, 3H), 7.74

<Step 2> ethyl  3- (2- (7- chloro -1H- indole -6- yl ) 메틸THIO ) propanoate Synthesis of

(24.3 mmol) of 6- (2-bromophenyl) -7-chloro-1H-indole, 3.59 g (26.77 mmol) of ethyl 3-mercaptopropanoate, 167 mg (0.18 mmol) of Pd ₂ dba ₃ , 197 mg (0.37 mmol) of dpephos and 8.4 g (61 mmol) of K ₂ CO ₃ were added to 100 ml of toluene and the mixture was stirred at 110 ° C for 15 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 6.38 g (17.7 mmol, yield: 72%) of ethyl 3- (2- (7-chloro-1H-indol-6-yl) phenylthio) propanoate was obtained by column chromatography.

^{1 H-NMR: δ 1.29 (} t, 3H), 2.58 (t, 2H), 3.12 (t, 2H), 4.12 (q, 2H), 6.25 (d, 1H), 7.37 (m, 4H), 7.70 ( m, 2 H), 8.06 (d, 1 H), 8.60 (s, 1 H)

<Step 3> IC Synthesis of -35

To a solution of 6.34 g (15.4 mmol) of ethyl 3- (2- (7-chloro-1H-indol-6-yl) phenylthio) propanoate and 2.60 g (23.2 mmol) potassium tert- And the mixture was stirred at 50 ° C for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 2.30 g (10.3 mmol, yield: 67%) of IC-35 was obtained by column chromatography.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.25 (d, 1H), 7.51 (m, 3H), 8.00 (m, 2H), 8.40 (d, 1H), 8.63 (s, 1H)

[ Preparation Example  36] IC Synthesis of -36

<Step 1> 2- ( benzofuran -5- yl ) -4,4,5,5- tetramethyl -1,3,2- dioxaborolane Synthesis of

A solution of 5-bromobenzofuran (25 g, 0.126 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane (38.67 g, 0.152 mol), Pd (dppf) Cl ₂ (3.11 g, 3 mol%), KOAc (37.36 g, 0.381 mol) and 1,4- dioxane Lt; / RTI &gt;

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to give 2- (benzofuran- 4,5,5-tetramethyl-1,3,2-dioxaborolane (23.23 g, yield 75%).

¹ H-NMR:? 1.25 (s, 12H), 6.46 (d, IH), 7.28 (d, IH), 7.43

<Step 2> Synthesis of 5- (2- nitrophenyl ) benzofuran Synthesis of

Benzofuran-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23 g, 78.52 mmol) was added to a solution of 1-bromo- _{94.23 mmol), K 2 CO 3} (32.56 g, 235.57 mmol) and 1,4-dioxane / H ₂ O, and then, Pd (PPh ₃ at 40 ℃ mix (400 ml / 200 ml)) 4 (4.54 g, 5 mol%) was added thereto, and the mixture was stirred at 110 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) benzofuran (12.40 g, yield 66%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.26 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.66 (t, 1H), 7.85 (t, 1H), 7.96 ( s, 1 H), 8.01 (d, 1 H), 8.06 (t, 1 H)

<Step 3> IC Synthesis of -36

5- (2-Nitrophenyl) benzofuran (10 g, 41.80 mmol), triphenylphosphine (27.41 g, 104.50 mmol) and 1,2-dichlorobenzene (150 ml) were mixed under a nitrogen stream and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-36 (4.76 g, yield 55%).

^{1 H-NMR: δ 6.51 (} d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.54 (d, 1H), 7.68 (t, 1H), 7.86 (t, 1H), 8.00 ( d, 1 H), 8.05 (t, 1 H), 10.58 (s, 1 H)

[ Preparation Example  37] IC Synthesis of -37

<Step 1> 2- ( benzofuran -6- yl ) -4,4,5,5- tetramethyl -1,3,2- dioxaborolane Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 6-bromobenzofuran was used instead of 5-bromobenzofuran to prepare 2- (benzofuran-6-yl) -4,4,5,5-tetramethyl-1 , 3,2-dioxaborolane.

¹ H-NMR:? 1.25 (s, 12H), 6.46 (d, IH), 7.28 (d, IH), 7.43

&Lt; Step 2 > 6- (2- nitrophenyl ) benzofuran Synthesis of

Benzofuran-6-yl) -4,4,5,5-tetramethyl-1 (2-benzofuran-5-yl) -4,4,5,5-tetramethyl- (2-nitrophenyl) benzofuran was obtained by following the procedure of <Step 2> of Preparation Example 36, except that 3,2-dioxaborolane was used.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.26 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.66 (t, 1H), 7.85 (t, 1H), 7.96 ( s, 1 H), 8.01 (d, 1 H), 8.06 (t, 1 H)

<Step 3> IC Synthesis of -37

IC-37 was obtained in the same manner as in <Step 3> of Preparation Example 36 except that 6- (2-nitrophenyl) benzofuran was used instead of 5- (2-nitrophenyl) benzofuran.

^{1 H-NMR: δ 6.51 (} d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.54 (d, 1H), 7.68 (t, 1H), 7.86 (t, 1H), 8.00 ( d, 1 H), 8.05 (t, 1 H), 10.58 (s, 1 H)

[ Preparation Example  38] IC Synthesis of -38

<Step 1> dibenzo [b, d] furan-3- amine Synthesis of

(10.0 ml, 150 mmol) and Cu (0.10 g, 5 mol%) were added to a solution of 3-bromodibenzo [b, d] furan (7.41 g, 30.0 mmol) , And the mixture was stirred at 110 DEG C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent of the filtered organic layer was removed and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 4.45 g (yield: 81%) of dibenzo [b, d] furan-3-amine.

^{1 H-NMR: δ 5.32 (} s, 2H), 6.33 (d, 1H), 7.34 (m, 2H), 7.43 (s, 1H), 7.65 (d, 2H), 7.89 (d, 1H)

&Lt; Step 2 > 3H- benzofuro [2,3-e] indole

(4.45 g, 24.29 mmol) was dissolved in H ₂ O / dioxane (10 ml / 90 ml) and then triethanolammonium chloride (0.45 g, 2.43 mmol) and RuCl ₃ put the <sub>`H 2 O (0.055 g,</sub> 0.2 mmol) and <sub>PPh 3 (0.191 g, 0.7 mmol</sub> ), SnCl 2` 2H 2 O (0.548 g, 2.43 mmol), and stirred at 180 ℃ for 20 hours. After the reaction was completed, the reaction mixture was poured into aqueous 5% HCl, extracted with methylene chloride, and charged with MgSO ₄ . The solvent of the filtered organic layer was removed and the residue was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain IC-38 2.7 g (yield: 53%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.13 (d, 1H), 7.27 (d, 1H), 7.35 (m, 2H), 7.66 (d, 1H), 7.88 (d, 2H), 10.46 ( s, 1 H)

[ Preparation Example  39] IC Synthesis of -39

&Lt; Step 1 > 5,5- dimethyl -5H- dibenzo [b, d] silol-3- amine Synthesis of

The same procedure as in <Step 1> of Preparation Example 38 was carried out except that 3-bromo-5,5-dimethyl-5H-dibenzo [b, d] silole was used instead of 3-bromodibenzo [b, 5,5-dimethyl-5H-dibenzo [b, d] silol-3-amine.

^{1 H-NMR: δ 0.68 (} s, 6H), 5.31 (s, 2H), 6.68 (d, 1H), 6.80 (s, 1H), 7.33 (t, 1H), 7.52 (d, 1H), 7.61 ( t, 1 H), 7.64 (d, 1 H), 7.91 (d, 1 H)

<Step 2> IC Synthesis of -39

Step 2 of Preparation Example 38 was repeated except that 5,5-dimethyl-5H-dibenzo [b, d] silol-3-amine was used in place of dibenzo [b, d] furan- And IC-39 was obtained.

^{1 H-NMR: δ0.66 (s} , 6H), 6.45 (d, 1H), 7.27 (d, 1H), 7.33 (t, 1H), 7.52 (d, 1H), 7.61 (t, 1H), 7.79 (d, IH), 7.89 (d, IH), 7.97 (d, IH), 10.42

[ Preparation Example  40] IC Synthesis of -40

&Lt; Step 1 > 5,5- 피덴 -5H- dibenzo [b, d] silol-3- amine Synthesis of

The same procedure as in <Step 1> of Preparation Example 38 was carried out except that 3-bromo-5,5-diphenyl-5H-dibenzo [b, d] silole was used instead of 3-bromodibenzo [b, 5,5-diphenyl-5H-dibenzo [b, d] silol-3-amine.

^{1 H-NMR: δ 5.33 (} s, 2H), 6.67 (d, 1H), 6.81 (s, 1H), 7.31 (t, 1H), 7.37 (m, 4H), 7.46 (m, 4H), 7.54 ( (m, 3H), 7.62 (t, IH), 7.66 (d, IH), 7.92

<Step 2> IC Synthesis of -40

Step 2 of Preparation Example 38 was repeated except that 5,5-diphenyl-5H-dibenzo [b, d] silol-3-amine was used in place of dibenzo [b, d] furan- And IC-40 was obtained.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.35 (m, 5H), 7.47 (m, 4H), 7.53 (m, 3H), 7.62 (t, 1H), 7.78 ( (d, IH), 7.90 (d, IH), 7.96 (d, IH), 10.41

[ Preparation Example  41] IC Synthesis of -41

<Step 1> IC Synthesis of -41

The same procedure as in <Step 2> of Preparation Example 38 was carried out except that dibenzo [b, d] selenophen-3-amine was used instead of dibenzo [b, d] furan- .

^{1 H-NMR: δ 6.47 (} d, 1H), 7.15 (d, 1H), 7.26 (d, 1H), 7.36 (m, 2H), 7.67 (d, 1H), 7.89 (d, 2H), 10.45 ( s, 1 H)

[ Preparation Example  42] IC Synthesis of -42

<Step 1> 2- ( benzo [b] selenophen-5- yl ) -4,4,5,5- tetramethyl -1,3,2-dioxaborolane

Benzo [b] selenophen-5-yl) -4,4-dioxolan-4-one was obtained by following the procedure of Step 1 of Preparation Example 36, except that 5-bromobenzo [b] selenophene was used instead of 5-bromobenzofuran. , 5,5-tetramethyl-1,3,2-dioxaborolane.

^{1 H-NMR: δ 1.26 (} s, 12H), 6.45 (d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.54 (d, 1H), 8.00 (s, 1H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) benzo [b] selenophene Synthesis of

Benzo [b] selenophen-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 2- (benzofuran- (2-nitrophenyl) benzo [b] selenophene was obtained in the same manner as in <Step 2> of Preparation Example 36 except that -tetramethyl-1,3,2-dioxaborolane was used.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.51 (d, 1H), 7.65 (t, 1H), 7.84 (t, 1H), 7.94 ( s, 1 H), 8.00 (d, 1 H), 8.05 (t, 1 H)

<Step 3> IC Synthesis of -42

IC-42 was obtained in the same manner as in <Step 3> of Preparation Example 36 except that 5- (2-nitrophenyl) benzo [b] selenophene was used instead of 5- (2-nitrophenyl) benzofuran.

^{1 H-NMR: δ 6.52 (} d, 1H), 7.26 (d, 1H), 7.44 (d, 1H), 7.55 (d, 1H), 7.69 (t, 1H), 7.85 (t, 1H), 7.96 ( d, 1 H), 8.03 (t, 1 H), 10.56 (s, 1 H)

[ Preparation Example  43] IC Synthesis of -43

<Step 1> 2- ( benzo [b] selenophen-6- yl ) -4,4,5,5- tetramethyl -1,3,2-dioxaborolane

Benzo [b] selenophen-6-yl) -4,4-dioxolan-4-one was obtained by following the procedure of Step 1 of Preparation Example 36, except that 6-bromobenzo [b] selenophene was used instead of 5-bromobenzofuran. , 5,5-tetramethyl-1,3,2-dioxaborolane.

¹ H-NMR:? 1.24 (s, 12H), 6.45 (d, IH), 7.28 (d, IH), 7.44

&Lt; Step 2 > 6- (2- nitrophenyl ) benzo [b] selenophene Synthesis of

Benzo [b] selenophen-6-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane in place of 2- (benzofuran-5- (2-nitrophenyl) benzo [b] selenophene was obtained by following the procedure of <Step 2> of Preparation Example 36, except that tetramethyl-1,3,2-dioxaborolane was used.

^{1 H-NMR: δ 6.46 (} d, 1H), 7.26 (d, 1H), 7.43 (d, 1H), 7.54 (d, 1H), 7.67 (t, 1H), 7.86 (t, 1H), 7.93 ( s, 1 H), 8.02 (d, 1 H), 8.08 (t, 1 H)

<Step 3> IC Synthesis of -43

IC-43 was obtained in the same manner as in <Step 3> of Preparation Example 36 except that 6- (2-nitrophenyl) benzo [b] selenophene was used instead of 5- (2-nitrophenyl) benzofuran.

^{1 H-NMR: δ 6.52 (} d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.52 (d, 1H), 7.67 (t, 1H), 7.85 (t, 1H), 8.01 ( d, 1 H), 8.09 (t, 1 H), 10.55 (s, 1 H)

[ Synthetic example  One] Inv Synthesis of -1

IC-1 (3 g, 10.63 mmol) in a nitrogen atmosphere, 3-bromobiphenyl (3.72 g, 15.94 mmol), Cu powder (0.07 g, 1.06 mmol), K 2 CO 3 (1.47 g, 10.63 mmol), Na 2 SO ₄ (1.51 g, 10.63 mmol) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C for 24 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which the water had been removed, and the residue was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to give 2.26 g (yield: 49%) of the target compound Inv-1.

GC-Mass (calculated: 434.18 g / mol, measured: 434 g / mol)

[ Synthetic example  2] Inv Synthesis of -2

Inv-2 (2.13 g, 46%) was obtained in the same manner as in Synthesis Example 1, except that 3- (4-bromophenyl) pyridine was used in place of 3-bromobiphenyl.

GC-Mass (calculated: 435.17 g / mol, measured: 435.17 g / mol)

[ Synthetic example  3] Inv Synthesis of -3

(3 g, 10.63 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.38 g, 12.75 mmol), Pd (OAc) ₂ (2.01 g, 21.25 mmol), P (t-bu) ₃ (0.21 g, 1.06 mmol) and Toluene (100 ml) were mixed and heated at 110 ° C for 12 hours Lt; / RTI &gt;

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and then water was removed with MgSO _{4. The} residue was purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain 4.79 g %).

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  4] Inv Synthesis of -4

Instead of 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) -1,3,5-triazine in place of 2- (3-chlorophenyl) (4.97 g, 79%) was obtained in the same manner as in Synthesis Example 3, except that the compound represented by Inv-4 was used.

GC-Mass (calculated: 591.22 g / mol, measured: 591 g / mol)

[ Synthetic example  5] Inv Synthesis of -5

The procedure of Synthesis Example 1 was repeated except that 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 3-bromobiphenyl, -5 (3.21 g, 50%).

GC-Mass (theory: 603.24 g / mol, measured: 603 g / mol)

[ Synthetic example  6] Inv Synthesis of -6

The same procedure as in Synthesis Example 1 was carried out except that 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine was used in place of 3-bromobiphenyl, -6 (3.47 g, 49%).

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  7] Inv Synthesis of -7

2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -1,3,5-triazine was used instead of 2- (3-chlorophenyl) (Inv-7) (5.38 g, 76%) was obtained in the same manner as in Synthesis Example 3, except that

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  8] Inv Synthesis of -8

The procedure of Synthesis Example 3 was repeated except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Inv-8 (4.63 g, 74%) was obtained as a target compound.

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  9] Inv Synthesis of -9

Except that 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) pyrimidine was used instead of 2- (3-chlorophenyl) -4,6-diphenyl- The procedure of Synthetic Example 3 was repeated to obtain the target compound Inv-9 (4.83 g, 77%).

GC-Mass (calculated: 590.22 g / mol, measured: 590 g / mol)

[ Synthetic example  10] Inv Synthesis of -10

Inv-10 (3.53 g, 50%) was obtained in the same manner as in Synthesis Example 1 except that 4- (5-bromobiphenyl-3-yl) -2,6-diphenylpyrimidine was used in place of 3-bromobiphenyl. ).

GC-Mass (calculated: 664.26 g / mol, measured: 664 g / mol)

[ Synthetic example  11] Inv Synthesis of -11

The same procedure as in Synthesis Example 1 was carried out except that 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole was used instead of 3-bromobiphenyl The target compound Inv-11 (3.39 g, 47%) was obtained.

GC-Mass (calculated: 678.25 g / mol, measured: 678 g / mol)

[ Synthetic example  12] Inv Synthesis of -12

Inv-12 (2.44 g, 44%) was obtained in the same manner as in Synthesis Example 1, except that (4-bromophenyl) diphenylborane was used in place of 3-bromobiphenyl.

GC-Mass (calculated: 522.23 g / mol, measured: 522 g / mol)

[ Synthetic example  13] Inv Synthesis of -13

Inv-13 (2.59 g, 45%) was obtained in the same manner as in Synthesis Example 1, except that (4-bromophenyl) diphenylphosphine was used in place of 3-bromobiphenyl.

GC-Mass (calculated: 542.19 g / mol, measured: 542 g / mol)

[ Synthetic example  14] Inv Synthesis of -14

Except that (4-chlorophenyl) triphenylsilane was used in place of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 14 (4.92 g, 75%).

GC-Mass (theory: 616.23 g / mol, measured: 616 g / mol)

[ Synthetic example  15] Inv Synthesis of -15

Inv-15 (4.51 g, 72%) was obtained in the same manner as in Synthesis Example 3, except that IC-2 was used instead of IC-1.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  16] Inv Synthesis of -16

Inv-16 (2.35 g, 51%) was obtained in the same manner as in Synthesis Example 1, except that IC-3 was used instead of IC-1.

GC-Mass (calculated: 434.18 g / mol, measured: 434 g / mol)

[ Synthetic example  17] Inv Synthesis of -17

Inv-17 (2.45 g, 53%) was obtained in the same manner as in Synthesis Example 1, except that IC-3 and 3- (4-bromophenyl) pyridine were used instead of IC-1 and 3-bromobiphenyl. .

GC-Mass (calculated: 435.17 g / mol, measured: 435 g / mol)

[ Synthetic example  18] Inv Synthesis of -18

Inv-18 (4.32 g, 69%) was obtained in the same manner as in Synthesis Example 3, except that IC-3 was used instead of IC-1.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  19] Inv -19 Synthesis

IC-1 and 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) -4,6-diphenyl- -1,3,5-triazine was used in place of the compound obtained in Synthesis Example 3 to obtain the desired compound Inv-19 (4.53 g, 72%).

GC-Mass (calculated: 591.22 g / mol, measured: 591 g / mol)

[ Synthetic example  20] Inv Synthesis of -20

Except that IC-3 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl in Synthesis Example 1 (Inv-20, 2.95 g, 46%) was obtained.

GC-Mass (theory: 603.24 g / mol, measured: 603 g / mol)

[ Synthetic example  21] Inv Synthesis of -21

Except that IC-3 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl in Synthesis Example 1 (3.18 g, 45%) of the desired compound, Inv-21, was obtained.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  22] Inv Synthesis of -22

IC-1 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -4,6-diphenyl- -1,3,5-triazine, the procedure of Synthesis Example 3 was repeated to obtain the desired compound, Inv-22 (6.07 g, 77%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  23] Inv Synthesis of -23

Except using IC-3 and 2- (3-chlorophenyl) -4,6-diphenylpyrimidine instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 3 was carried out to obtain the target compound Inv-23 (4.69 g, 75%).

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  24] Inv Synthesis of -24

IC-1 and 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) -4,6-diphenyl- pyrimidine, the target compound Inv-24 (4.46 g, 71%) was obtained by carrying out the same procedure as in Synthesis Example 3 above.

GC-Mass (calculated: 590.22 g / mol, measured: 590 g / mol)

[ Synthetic example  25] Inv Synthesis of -25

The procedure of Synthesis Example 1 was repeated except that IC-3 and 4- (5-bromobiphenyl-3-yl) -2,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl, -25 (3.04 g, 43%).

GC-Mass (calculated: 664.26 g / mol, measured: 664 g / mol)

[ Synthetic example  26] Inv Synthesis of -26

Except for using IC-3 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole instead of IC-1 and 3-bromobiphenyl. The procedure of Example 1 was followed to obtain the target compound Inv-26 (2.96 g, 41%).

GC-Mass (calculated: 678.25 g / mol, measured: 678 g / mol)

[ Synthetic example  27] Inv -27

Inv-27 (2.66 g, 48%) was obtained in the same manner as in Synthesis Example 1 except that IC-3 and (4-bromophenyl) diphenylborane were used instead of IC-1 and 3-bromobiphenyl .

GC-Mass (calculated: 522.23 g / mol, measured: 522 g / mol)

[ Synthetic example  28] Inv -28 Synthesis

Inv-28 (2.54 g, 44%) was obtained in the same manner as in Synthesis Example 1 except that IC-3 and (4-bromophenyl) diphenylphosphine were used instead of IC-1 and 3-bromobiphenyl .

GC-Mass (calculated: 542.19 g / mol, measured: 542 g / mol)

[ Synthetic example  29] Inv Synthesis of -29

Except that IC-3 and (4-chlorophenyl) triphenylsilane were used in place of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- To obtain the target compound Inv-29 (4.65 g, 71%).

GC-Mass (theory: 616.23 g / mol, measured: 616 g / mol)

[ Synthetic example  30] Inv Synthesis of -30

Inv-30 (4.70 g, 75%) was obtained in the same manner as in Synthesis Example 3 except that IC-4 was used instead of IC-1.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  31] Inv Synthesis of -31

Inv-31 (4.57 g, 73%) was obtained in the same manner as in Synthesis Example 3 except that IC-5 was used instead of IC-1.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  32] Inv Synthesis of -32

Inv-32 (4.82 g, 77%) was obtained in the same manner as in Synthesis Example 3, except that IC-6 was used instead of IC-1.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  33] Inv Synthesis of -33

The mixture was mixed with IC-7 (5 g, 13.84 mmol), phenylboronic acid (2.03 g, 16.61 mmol), NaOH (1.66 g, 41.52 mmol) and THF / H ₂ O (100 ml / 500 ml) Pd (PPh ₃ ) ₄ (0.80 g, 5 mol%) was added thereto at 40 ° C, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 3,7-diphenyl-3,10-dihydropyrrolo [3,2-a] carbazole.

Inv-33 (6.27 g, 68%) was obtained in the same manner as in Synthesis Example 3 except that 3,7-diphenyl-3,10-dihydropyrrolo [3,2-a] carbazole was used instead of IC- .

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  34] Inv Synthesis of -34

Inv-34 (7.94 g, 69%) was obtained in the same manner as in Synthesis Example 33 except that 9-phenyl-9H-carbazol-3-ylboronic acid was used in place of phenylboronic acid.

GC-Mass (calculated: 830.32 g / mol, measured: 830 g / mol)

[ Synthetic example  35] Inv Synthesis of -35

Inv-35 (6.64 g, 72%) was obtained in the same manner as in Synthesis Example 33 except that IC-8 was used instead of IC-7.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  36] Inv Synthesis of -36

The same procedure as in Synthesis Example 33 was carried out except that IC-7 and IC-8 and 9- (4,6-diphenylpyridin-2-yl) -9H-carbazol-3-ylboronic acid were used instead of phenylboronic acid The target compound Inv-36 (10.22 g, 75%) was obtained.

GC-Mass (theory: 983.37 g / mol, measurement: 983 g / mol)

[ Synthetic example  37] Inv Synthesis of -37

Inv-37 (4.34 g, 71%) was obtained in the same manner as in Synthesis Example 3, except that IC-9 was used instead of IC-1.

GC-Mass (theory: 603.24 g / mol, measured: 603 g / mol)

[ Synthetic example  38] Inv Synthesis of -38

Except that IC-9 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl in Synthesis Example 1 (Inv-38, 3.58 g, 52%) was obtained.

GC-Mass (calculated: 679.27 g / mol, measured: 679 g / mol)

[ Synthetic example  39] Inv Synthesis of -39

IC-1 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -4,6-diphenyl- -1,3,5-triazine was used in place of the target compound, Inv-39 (5.20 g, 68%) was obtained in the same manner as in Synthesis Example 3.

GC-Mass (calculated: 775.30 g / mol, measured: 775 g / mol)

[ Synthetic example  40] Inv Synthesis of -40

Inv-40 (3.90 g, 70%) was obtained in the same manner as in Synthesis Example 3, except that IC-10 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  41] Inv Synthesis of -41

The procedure of Synthesis Example 1 was repeated except that IC-10 and 2- (4-bromophenyl) -4,6-diphenylpyrimidine were used in place of IC-1 and 3-bromobiphenyl, g, 48%).

GC-Mass (calculated: 664.26 g / mol, measured: 664 g / mol)

[ Synthetic example  42] Inv Synthesis of -42

Inv-42 (3.74 g, 73%) was obtained in the same manner as in Synthesis Example 3 except that IC-11 was used instead of IC-1.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  43] Inv Synthesis of -43

Except that IC-11 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl in Synthesis Example 1 To obtain the target compound Inv-43 (2.94 g, 52%).

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[ Synthetic example  44] Inv Synthesis of -44

The procedure of Synthesis Example 1 was repeated except that IC-11 and 3,3 '- (5-bromo-1,3-phenylene) dipyridine were used instead of IC-1 and 3-bromobiphenyl, -44 (2.34 g, 51%).

GC-Mass (calculated: 664.26 g / mol, measured: 664 g / mol)

[ Synthetic example  45] Inv Synthesis of -45

Except that IC-11 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole were used instead of IC-1 and 3-bromobiphenyl. The procedure of Example 1 was repeated to obtain the target compound Inv-45 (2.81 g, 49%).

GC-Mass (calculated: 830.32 g / mol, measured: 830 g / mol)

[ Synthetic example  46] Inv Synthesis of -46

Inv-46 (4.05 g, 72%) was obtained in the same manner as in Synthesis Example 3, except that IC-12 was used instead of IC-1.

GC-Mass (657.21 g / mol, measured: 657 g / mol)

[ Synthetic example  47] Inv Synthesis of -47

IC-1 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin) instead of IC-12 and 2- (3-chlorophenyl) -2-yl) -9H-carbazole was used in place of the target compound, Inv-47 (3.66 g, 65%) was obtained in the same manner as in Synthesis Example 3.

GC-Mass (657.21 g / mol, measured: 657 g / mol)

[ Synthetic example  48] Inv Synthesis of -48

The procedure of Synthesis Example 1 was repeated except that IC-12 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl, g, 47%).

GC-Mass (calculated: 656.22 g / mol, measured: 656 g / mol)

[ Synthetic example  49] Inv Synthesis of -49

Inv-49 (3.90 g, 70%) was obtained in the same manner as in Synthesis Example 3, except that IC-13 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  50] Inv Synthesis of -50

IC-1 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -4,6-diphenyl- -1,3,5-triazine was used in place of the target compound, Inv-50 (5.00 g, 73%) was obtained in the same manner as in Synthesis Example 3.

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[ Synthetic example  51] Inv Synthesis of -51

Inv-51 (3.85 g, 69%) was obtained in the same manner as in Synthesis Example 3, except that IC-14 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  52] Inv Synthesis of -52

The same procedure as in Synthesis Example 1 was carried out except that IC-15 and 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl Inv-52 (2.90 g, 52%) as a target compound was obtained.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  53] Inv Synthesis of -53

Inv-53 (3.85 g, 69%) was obtained by carrying out the same procedure as in Synthesis Example 3, except that IC-15 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  54] Inv Synthesis of -54

The procedure of Synthesis Example 1 was repeated except that IC-15 and 2- (4-bromophenyl) -5-phenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl to obtain the desired compound Inv-54 (2.66 g, 54%).

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  55] Inv Synthesis of -55

Inv-55 (3.48 g, 68%) was obtained in the same manner as in Synthesis Example 3, except that IC-16 was used instead of IC-1.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  56] Inv Synthesis of -56

(1.99 g, 49%) was obtained by carrying out the same processes as in Synthesis Example 1 except that IC-16 and 2- (4-bromophenyl) pyrimidine were used instead of IC-1 and 3-bromobiphenyl. .

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  57] Inv Synthesis of -57

Inv-57 (4.00 g, 71%) was obtained in the same manner as in Synthesis Example 3, except that IC-17 was used instead of IC-1.

GC-Mass (657.21 g / mol, measured: 657 g / mol)

[ Synthetic example  58] Inv Synthesis of -58

Except that IC-17 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl. (Inv-58, 2.89 g, 46%) was obtained.

GC-Mass (733.25 g / mol, measured: 733 g / mol)

[ Synthetic example  59] Inv Synthesis of -59

Inv-59 (3.49 g, 69%) was obtained by carrying out the same procedure as in Synthesis Example 3, except that IC-18 was used instead of IC-1.

GC-Mass (calculated: 754.28 g / mol, measured: 754 g / mol)

[ Synthetic example  60] Inv Synthesis of -60

Except that IC-1 and 3-bromobiphenyl were replaced by IC-18 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) The procedure of Example 1 was repeated to obtain the target compound Inv-60 (2.49 g, 44%).

GC-Mass (calculated: 843.31 g / mol, measured: 843 g / mol)

[ Synthetic example  61] Inv Synthesis of -61

Inv-61 (1.62 g, 48%) was obtained in the same manner as in Synthesis Example 1 except that IC-19 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.

GC-Mass (calculated: 678.25 g / mol, measured: 678 g / mol)

[ Synthetic example  62] Inv Synthesis of -62

The procedure of Synthesis Example 1 was repeated except that IC-19 and 1-bromo-3,5-diphenyl benzene were used instead of IC-1 and 3-bromobiphenyl to obtain the desired compound Inv-62 (1.94 g, 47 %).

GC-Mass (calculated: 830.32 g / mol, measured: 830 g / mol)

[ Synthetic example  63] Inv Synthesis of -63

Inv-63 (3.79 g, 68%) was obtained in the same manner as in Synthesis Example 3 except that IC-20 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  64] Inv Synthesis of -64

Inv-64 (4.18 g, 75%) was obtained in the same manner as in Synthesis Example 3, except that IC-21 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665.26 g / mol)

[ Synthetic example  65] Inv Synthesis of -65

IC-1 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -4,6-diphenyl- -1,3,5-triazine, the procedure of Synthetic Example 3 was repeated to give the target compound Inv-65 (5.07 g, 74%).

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[ Synthetic example  66] Inv Synthesis of -66

Inv-66 (4.01 g, 72%) was obtained in the same manner as in Synthesis Example 3, except that IC-22 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  67] Inv Synthesis of -67

The procedure of Synthesis Example 1 was repeated except that IC-22 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl, g, 51%).

GC-Mass (calculated: 664.26 g / mol, measured: 664 g / mol)

[ Synthetic example  68] Inv Synthesis of -68

Inv-68 (3.74 g, 73%) was obtained in the same manner as in Synthesis Example 3, except that IC-23 was used instead of IC-1.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  69] Inv Synthesis of -69

The same procedure as in Synthesis Example 1 was carried out except that IC-23 was used instead of IC-1 and 3-bromobiphenyl and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5- To obtain the target compound Inv-69 (2.71 g, 48%).

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[ Synthetic example  70] Inv Synthesis of -70

Inv-70 (2.07 g, 51%) was prepared in the same manner as in Synthesis Example 1, except that IC-24 and 2- (4-bromophenyl) pyridine were used instead of IC-1 and 3-bromobiphenyl. .

GC-Mass (calculated: 587.24 g / mol, measured: 587 g / mol)

[ Synthetic example  71] Inv Synthesis of -71

Inv-71 (4.00 g, 78%) was obtained in the same manner as in Synthesis Example 3, except that IC-24 was used instead of IC-1.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  72] Inv Synthesis of -72

Inv-72 (1.83 g, 53%) was obtained in the same manner as in Synthesis Example 1 except that IC-25 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  73] Inv Synthesis of -73

The procedure of Synthesis Example 1 was repeated except that IC-25 and 1-bromo-3,5-diphenyl benzene were used instead of IC-1 and 3-bromobiphenyl to obtain the desired compound Inv-73 (2.25 g, 52 %).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  74] Inv Synthesis of -74

Inv-74 (1.91 g, 49%) was obtained in the same manner as in Synthesis Example 1, except that IC-25 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  75] Inv Synthesis of -75

Inv-75 (1.55 g, 45%) was obtained in the same manner as in Synthesis Example 1 except that IC-26 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  76] Inv Synthesis of -76

Inv-76 (1.83 g, 47%) was obtained in the same manner as in Synthesis Example 1, except that IC-26 and 4- (4-bromophenyl) pyridine were used instead of IC-1 and 3-bromobiphenyl. .

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  77] Inv Synthesis of -77

Inv-77 (1.48 g, 43%) was obtained in the same manner as in Synthesis Example 1, except that IC-27 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[ Synthetic example  78] Inv Synthesis of -78

Inv-78 (1.87 g, 48%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that IC-27 was used instead of IC-1.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[ Synthetic example  79] Inv Synthesis of -79

Inv-79 (1.75 g, 45%) was obtained in the same manner as in Synthesis Example 1 except that IC-27 and 4-bromobiphenyl were used instead of IC-1 and 3-bromobiphenyl.

GC-Mass (calculated: 665.26 g / mol, measured: 665.26 g / mol)

[ Synthetic example  80] Inv Synthesis of -80

The procedure of Synthesis Example 1 was repeated except that IC-27 and 1-bromo-3,5-diphenyl benzene were used instead of IC-1 and 3-bromobiphenyl to obtain the desired compound Inv-80 (2.12 g, 49 %).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  81] Inv Synthesis of -81

Inv-81 (1.79 g, 52%) was obtained in the same manner as in Synthesis Example 1 except that IC-28 and iodobenzene were used instead of IC-1 and 3-bromobiphenyl.

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  82] Inv Synthesis of -82

The procedure of Synthesis Example 1 was repeated except that IC-28 and 1-bromo-3,5-diphenyl benzene were used instead of IC-1 and 3-bromobiphenyl to obtain the desired compound Inv-82 (1.99 g, 46 %).

GC-Mass (calculated: 740.29 g / mol, measured: 740 g / mol)

[ Synthetic example  83] Inv Synthesis of -83

Except that IC-14 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 3-bromobiphenyl in Synthesis Example 1 (Inv-83, 3.54 g, 57%) was obtained.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[ Synthetic example  84] Inv Synthesis of -84

The procedure of Synthesis Example 1 was repeated except that IC-20 and 2,2 '- (5-bromo-1,3-phenylene) dipyridine were used instead of IC-1 and 3-bromobiphenyl, -84 (2.61 g, 53%).

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[ Synthetic example  85] Inv Synthesis of -85

(2.23 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.21 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) and DMF 30 ml) were mixed and stirred at room temperature for 3 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered and purified by column chromatography to obtain the target compound Inv-85 (3.77 g, yield: 83%).

GC-Mass (theory: 454.55 g / mol, measured: 454 g / mol)

[ Synthetic example  86] Inv Synthesis of -86

(2.26 g, 10.0 mmol), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.0 mmol), NaH ) And DMF (30 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added and the solid compound was filtered and purified by column chromatography to obtain the target compound Inv-86 (3.45 g, yield: 65%).

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  87] Inv Synthesis of -87

(2.26 g, 10.0 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.0 mmol), NaH ) And DMF (30 ml) were mixed and stirred at room temperature for 3 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered and purified by column chromatography to obtain the target compound Inv-87 (3.77 g, yield: 71%).

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  88] Inv Synthesis of -88

Inv-88 (3.45 g, yield: 65%) was obtained by following the same procedure as in Synthesis Example 87 except that IC-29b (2.23 g, 10.0 mmol) was used instead of IC-29a.

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  89] Inv Synthesis of -89

Inv-89 (3.33 g, yield: 63%) was obtained by following the same procedure as Synthesis Example 87, except that IC-30 (2.23 g, 10.0 mmol) was used instead of IC-29a.

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  90] Inv Synthesis of -90

Inv-90 (3.18 g, yield: 60%) was obtained by following the same procedure as in Synthesis Example 87 except that IC-31a (2.23 g, 10.0 mmol) was used instead of IC-29a.

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  91] Inv Synthesis of -91

Inv-91 (3.28 g, yield: 62%) was obtained by following the same procedure as in Synthesis Example 87 except that IC-31b (2.23 g, 10.0 mmol) was used instead of IC-29a.

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  92] Inv Synthesis of -92

Inv-92 (3.50 g, yield: 77%) was obtained by following the same procedure as in Synthesis Example 87 except that IC-32 (2.23 g, 10.0 mmol) was used instead of IC-29a.

GC-Mass (theory: 454.55 g / mol, measured: 454 g / mol)

[ Synthetic example  93] Inv Synthesis of -93

The procedure of Synthesis Example 1 was repeated except that IC-33 was used instead of IC-1 and 1-bromo-4-phenylisoquinoline was used instead of 2-bromo-4,6-diphenylpyridine. 3.26 g, yield: 58%).

GC-Mass (calculated: 436.19 g / mol, measured: 436 g / mol)

[ Synthetic example  94] Inv Synthesis of -94

The procedure of Synthesis Example 1 was repeated except that IC-34 was used instead of IC-1 and 4-bromo-2,6-diphenylpyridine was used instead of 2-bromo-4,6-diphenylpyridine. 94 (3.11 g, yield 63%).

GC-Mass (calculated: 586.24 g / mol, measured: 586 g / mol)

[ Synthetic example  95] Inv - 95's  synthesis

Inv-95 (3.40 g, yield: 64%) was obtained by carrying out the same procedure as in Synthesis Example 87 except that IC-35 (2.23 g, 10.0 mmol) was used instead of IC-29a.

GC-Mass (calculated: 530.64 g / mol, measured: 530 g / mol)

[ Synthetic example  96] Inv Synthesis of -96

(5.97 g, 17.37 mmol), Pd (OAc) ₂ (0.16 g, 17.37 mmol), IC-36 (3 g, 14.48 mmol) (2.78 g, 28.95 mmol), P (t-bu) ₃ (0.29 g, 1.45 mmol) and Toluene (100 ml) were mixed and heated at 110 ° C. for 12 hours Lt; / RTI &gt;

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain Inv-96 (5.59 g, yield 75% .

GC-Mass (calculated: 514.18 g / mol, measured: 514 g / mol)

[ Synthetic example  97] Inv Synthesis of -97

Inv-97 (5.29 g, 71%) was obtained in the same manner as in Synthesis Example 96 except that IC-37 was used instead of IC-36.

GC-Mass (calculated: 514.18 g / mol, measured: 514 g / mol)

[ Synthetic example  98] Inv Synthesis of -98

Inv-98 (5.44 g, 73%) was obtained in the same manner as in Synthesis Example 96 except that IC-38 was used instead of IC-36.

GC-Mass (calculated: 514.18 g / mol, measured: 514 g / mol)

[ Synthetic example  99] Inv Synthesis of -99

Inv-99 (4.62 g, 69%) was obtained in the same manner as in Synthesis Example 96, except that IC-39 was used instead of IC-36.

GC-Mass (calculated: 556.21 g / mol, measured: 556 g / mol)

[ Synthetic example  100] Inv Synthesis of -100

Inv-100 (3.66 g, 67%) was obtained in the same manner as in Synthesis Example 96 except that IC-40 was used instead of IC-36.

GC-Mass (calculated: 680.24 g / mol, measured: 680 g / mol)

[ Synthetic example  101] Inv Synthesis of -101

Inv-101 (4.87 g, 76%) was obtained in the same manner as in Synthesis Example 96 except that IC-41 was used instead of IC-36.

GC-Mass (calculated: 578.10 g / mol, measured: 578 g / mol)

[ Synthetic example  102] Inv Synthesis of -102

Inv-102 (4.75 g, 74%) was obtained in the same manner as in Synthesis Example 96, except that IC-42 was used instead of IC-36.

GC-Mass (calculated: 578.10 g / mol, measured: 578 g / mol)

[ Synthetic example  103] Inv Synthesis of -103

Inv-103 (4.68 g, 73%) was obtained in the same manner as in Synthesis Example 96 except that IC-43 was used instead of IC-36.

GC-Mass (calculated: 578.10 g / mol, measured: 578 g / mol)

[ Synthetic example  104] Inv Synthesis of -104

2-chloro-4-phenylquinazoline (10.2 g, 42.53 mmol), Cu powder (0.22 g, 3.544 mmol), K ₂ CO ₃ (9.8 g, 70.88 mmol) Na ₂ SO ₄ (10 g, 70.88 mmol) and nitrobenzene (350 ml) were mixed and stirred at 190 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain Inv-104 (8.6 g, yield 50%).

GC-Mass (calculated: 486.18 g / mol, measured: 486 g / mol)

[ Synthetic example  105] Inv Synthesis of -105

Inv-105 was obtained in the same manner as in Synthesis Example 104 except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline was used in place of 2-chloro-4-phenylquinazoline.

GC-Mass (calculated: 612.23 g / mol, measured: 612 g / mol)

[ Synthetic example  106] Inv Synthesis of -106

Inv-106 was obtained in the same manner as in Synthesis Example 104 except that IC-2 was used instead of IC-1.

GC-Mass (calculated: 486.18 g / mol, measured: 486 g / mol)

[ Synthetic example  107] Inv Synthesis of -107

Inv-107 was obtained in the same manner as in Synthesis Example 104 except that IC-4 was used instead of IC-1.

GC-Mass (calculated: 486.18 g / mol, measured: 486 g / mol)

[ Synthetic example  108] Inv Synthesis of -108

Inv-108 was obtained in the same manner as in Synthesis Example 104 except that IC-5 was used instead of IC-1.

GC-Mass (calculated: 486.18 g / mol, measured: 486 g / mol)

[ Synthetic example  109] Synthesis of compound 1

<Step 1> 2,5- Diphenylpyridine Synthesis of

A mixture of 23.70 g (0.1 mol) of 2,5-dibromopyridine, 30.48 g (0.25 mol) of phenylboronic acid, 41.46 g (0.3 mol) of anhydrous K ₂ CO ₃ and 800 ml / 300 ml of toluene / H ₂ O And the mixture was stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 5.78 g (5 mol%) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 19.20 g (yield: 83%) of 2,5-diphenylpyridine (L1) was obtained by column chromatography.

&Lt; Step 2 > Diphenylpyridinato iridium dimer Synthesis of

5.0 g (13.8 mmol) of IrCl ₃ .xH ₂ O and L1 (9.6 g, 41.4 mmol) were refluxed in a mixed solvent of 120 ml of 2-methoxyethanol and 40 ml of water under a nitrogen stream for 20 hours. The reaction mixture was cooled to room temperature, and the resulting precipitate was filtered, and the product was purified with a solvent mixture of acetone and ethanol in a ratio of 1: 1 to obtain D1 (9.31 g, yield 98%).

&Lt; Step 3 > Coordination Cationic  Synthesis of intermediates

The D1 (8.0 g, 5.81 mmol) and AgPF ₆ (3.67 g, 14.53 mmol) were added to a mixed solvent of methylene chloride (300 ml) and methanol (100 ml), and the mixture was stirred at room temperature for 6 hours in a nitrogen stream. The reaction mixture was passed through Celite to remove AgCl and the filtrate was distilled under reduced pressure to remove about 90% of the solvent. Then, ethyl ether and hexane were further added to obtain the desired intermediate compound I1 (8.62 g, yield 86%) .

<Step 4> Synthesis of Compound 1

The intermediate compound I1 (8.62 g, 10.0 mmol) and L1 (6.94 g, 30 mmol) were refluxed in 300 ml of ethanol under a nitrogen atmosphere for 20 hours. After completion of the reaction, the precipitate obtained by filtration was purified by column chromatography to obtain the target compound compound 1 (8.12 g, yield 92%).

GC-Mass (calculated: 883.07 g / mol, measured: 883 g / mol)

[ Synthetic example  110] Synthesis of Compound 9

<Step 1> 2- 페닐 피딘 Synthesis of

L2 (13.2 g, yield 85%) was obtained in the same manner as in <Step 1> of the synthesis example 104 except that 2-bromopyridine was used in place of 2,5-dibromopyridine.

&Lt; Step 2 > 2- phenylpyridinato iridium dimer Synthesis of

D2 (7.59 g, yield 92%) was obtained in the same manner as in <Step 2> of Preparation Example 104, except that the above-mentioned L2 was used instead of L1.

&Lt; Step 3 > Coordination Cationic  Synthesis of intermediates

Intermediate compound I2 (6.28 g, yield 85%) was obtained in the same manner as in <Step 3> of Preparation Example 104 except that D2 was used instead of D1.

<Step 4> Synthesis of Compound 9

Compound 9 (6.07 g, yield 83%) was obtained in the same manner as in <Step 4> of the above Synthesis Example except that I2 was used instead of I1.

GC-Mass (calculated: 730.88 g / mol, measured: 731 g / mol)

[ Synthetic example  111] Preparation of Compound 149

<Step 1> 2- biphenyl -3- yl - 피리딘 Synthesis of

L3 (20.59 g, yield 89%) was obtained in the same manner as in <Step 1> of Preparation Example 105, except that 3-biphenylboronic acid was used in place of phenylboronic acid.

<Step 2> Synthesis of Compound 149

5.0 g (10.0 mmol) of Ir (acac) ₃ and L3 (6.94 g, 30.0 mmol) were added to glycerol (30 ml) under a nitrogen stream and refluxed for 24 hours. After completion of the reaction, the precipitate obtained by filtration was purified by column chromatography to obtain the target compound compound 149 (2.47 g, 28% yield).

GC-Mass (calculated: 883.07 g / mol, measured: 883 g / mol)

[ Synthetic example  112] Synthesis of Compound 164

<Step 1> 2- phenylquinoline Synthesis of

Insert the 20.8 g (0.1 mol) 2- bromoquinoline, 14.63 g (0.12 mol) phenylboronic acid, 41.46 g (0.3 mol) of anhydrous K ₂ CO ₃ and toluene / H ₂ O in 800 ml / 300 ml of the under nitrogen gas stream, Lt; / RTI &gt; At 40 ℃ into the Pd (PPh _{3) 4} of 5.78 g (5 mol%) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.40 g (yield: 80%) of 2-phenylquinoline (L4) was obtained by column chromatography.

&Lt; Step 2 > 2- phenylquinolinato iridium dimer Synthesis of

5.0 g (13.8 mmol) of IrCl ₃ .xH ₂ O and L4 (8.49 g, 41.4 mmol) were refluxed in a mixed solvent of 120 ml of 2-methoxyethanol and 40 ml of water under a nitrogen stream for 20 hours. The reaction mixture was cooled to room temperature, and the resulting precipitate was filtered, and the product was purified with a solvent mixture of acetone and ethanol at a ratio of 1: 1 to obtain D4 (8.49 g, yield 95%).

<Step 3> Synthesis of Compound 164

The D4 (5.01 g, 5.81 mmol), 2,4-pentanedione (1.74 g, 17.4 mmol) and anhydrous Na ₂ CO ₃ (4.82 g, 34.86 mol) were added to 120 ml of 2-ethoxyethanol and refluxed. The reaction mixture was cooled to room temperature, and the resulting precipitate was filtered and separated by column chromatography to obtain recrystallized compound 164 as a target compound (2.64 g, yield 92%).

GC-Mass (calculated: 496.09 g / mol, measured: 496 g / mol)

[ Example  1 ~ 103] Organic Field  Fabrication of light emitting device

The compound 1 of Inv-1 to Inv-103 synthesized in Synthesis Example 1-103 and the compound 1 of Synthesis Example 109 were subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was fabricated according to the following procedure.

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

Each compound (90%) of m-MTDATA (60 nm) / TCTA (80 nm) / Inv-1 to Inv-103 + Compound 1 (10%) (300 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Example  104 ~ 114] Organic Field  Fabrication of light emitting device

Inv-3, Inv-5, Inv-6, Inv-7, Inv-8, Inv-18, Inv-21, Inv-23, Inv-30, Inv- 87 was prepared in the same manner as in Example 1, except that compound 9 of Synthesis Example 110 was used as the luminescent dopant material, thereby preparing a green organic electroluminescent device.

[ Example  115 ~ 125] Organic Field  Fabrication of light emitting device

Inv-3, Inv-5, Inv-6, Inv-7, Inv-8, Inv-18, Inv-21, Inv-23, Inv-30, Inv- A green organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound 149 of Synthesis Example 111 was used as the luminescent dopant material.

[ Example  126 ~ 131] Organic Field  Fabrication of light emitting device

Except that compound Inv-18, Inv-104, Inv-105, Inv-106, Inv-107 and Inv-108 were used as the luminescent host material in the formation of the light emitting layer and compound 164 of Synthesis Example 112 was used as the luminescent dopant substance A green organic electroluminescent device was fabricated in the same manner as in Example 1.

[ Comparative Example  1] Organic Field  Fabrication of light emitting device

The procedure of Example 1 was repeated, except that CBP was used instead of Compound Inv-1 as a luminescent host material in the formation of the light emitting layer, and Ir (ppy) ₃ was used in place of compound 1 of Synthesis Example 109 as a luminescent dopant material. Respectively.

[ Comparative Example  2] Organic Field  Fabrication of light emitting device

The procedure of Example 126 was repeated except that CBP was used instead of Compound Inv-18 as a luminescent host material in the formation of the light emitting layer and Ir (piq) ₂ (acac) was used in place of Compound 164 of Synthetic Example 112 as a luminescent dopant material. An electroluminescent device was fabricated.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , Ir (piq) ₂ (acac), CBP and BCP used are as follows.

[ Evaluation example  One]

The driving voltage, the emission peak and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1-125 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Dopant The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Inv-1 Compound 1 6.60 545 41.4 Example 2 Inv-2 Compound 1 6.55 549 42.9 Example 3 Inv-3 Compound 1 6.52 546 43.2 Example 4 Inv-4 Compound 1 6.65 546 43.5 Example 5 Inv-5 Compound 1 6.72 543 41.7 Example 6 Inv-6 Compound 1 6.68 546 42.1 Example 7 Inv-7 Compound 1 6.62 546 42.6 Example 8 Inv-8 Compound 1 6.66 547 42.4 Example 9 Inv-9 Compound 1 6.85 548 41.8 Example 12 Inv-12 Compound 1 6.72 549 41.1 Example 11 Inv-11 Compound 1 6.65 545 42.1 Example 12 Inv-12 Compound 1 6.62 544 42.8 Example 13 Inv-13 Compound 1 6.75 546 42.2 Example 14 Inv-14 Compound 1 6.73 545 42.9 Example 15 Inv-15 Compound 1 6.72 543 41.2 Example 16 Inv-16 Compound 1 6.64 546 39.9 Example 17 Inv-17 Compound 1 6.59 547 40.9 Example 18 Inv-18 Compound 1 6.61 543 42.6 Example 19 Inv-19 Compound 1 6.69 548 41.2 Example 22 Inv-22 Compound 1 6.62 544 42.7 Example 21 Inv-21 Compound 1 6.65 546 41.3 Example 22 Inv-22 Compound 1 6.67 548 42.0 Example 23 Inv-23 Compound 1 6.62 545 41.1 Example 24 Inv-24 Compound 1 6.75 546 42.0 Example 25 Inv-25 Compound 1 6.72 547 41.9 Example 26 Inv-26 Compound 1 6.75 545 42.3 Example 27 Inv-27 Compound 1 6.64 547 42.2 Example 28 Inv-28 Compound 1 6.62 548 41.1 Example 29 Inv-29 Compound 1 6.64 547 42.0 Example 32 Inv-32 Compound 1 6.72 546 41.8 Example 31 Inv-31 Compound 1 6.65 543 41.3 Example 32 Inv-32 Compound 1 6.66 549 42.2 Example 33 Inv-33 Compound 1 6.64 541 41.3 Example 34 Inv-34 Compound 1 6.75 546 41.8 Example 35 Inv-35 Compound 1 6.72 543 42.5 Example 36 Inv-36 Compound 1 6.69 546 42.9 Example 37 Inv-37 Compound 1 6.65 544 41.3 Example 38 Inv-38 Compound 1 6.68 547 41.7 Example 39 Inv-39 Compound 1 6.61 548 41.6 Example 42 Inv-42 Compound 1 6.72 544 42.4 Example 41 Inv-41 Compound 1 6.65 546 42.3 Example 42 Inv-42 Compound 1 6.62 548 41.2 Example 43 Inv-43 Compound 1 6.61 545 41.8 Example 44 Inv-44 Compound 1 6.55 546 42.1 Example 45 Inv-45 Compound 1 6.66 547 41.0 Example 46 Inv-46 Compound 1 6.63 546 42.2 Example 47 Inv-47 Compound 1 6.65 547 41.3 Example 48 Inv-48 Compound 1 6.62 548 42.1 Example 49 Inv-49 Compound 1 6.69 545 42.6 Example 52 Inv-52 Compound 1 6.62 546 41.1 Example 51 Inv-51 Compound 1 6.72 544 42.5 Example 52 Inv-52 Compound 1 6.65 546 41.2 Example 53 Inv-53 Compound 1 6.66 548 41.5 Example 54 Inv-54 Compound 1 6.67 543 42.0 Example 55 Inv-55 Compound 1 6.59 547 41.9 Example 56 Inv-56 Compound 1 6.51 546 42.3 Example 57 Inv-57 Compound 1 6.55 544 42.3 Example 58 Inv-58 Compound 1 6.63 546 41.2 Example 59 Inv-59 Compound 1 6.65 545 42.2 Example 62 Inv-62 Compound 1 6.65 546 41.3 Example 61 Inv-61 Compound 1 6.62 542 41.5 Example 62 Inv-62 Compound 1 6.72 542 42.0 Example 63 Inv-63 Compound 1 6.72 546 42.3 Example 64 Inv-64 Compound 1 6.68 546 41.2 Example 65 Inv-65 Compound 1 6.65 545 41.0 Example 66 Inv-66 Compound 1 6.71 546 41.1 Example 67 Inv-67 Compound 1 6.65 547 41.3 Example 68 Inv-68 Compound 1 6.67 548 41.1 Example 69 Inv-69 Compound 1 6.62 547 42.1 Example 72 Inv-72 Compound 1 6.69 544 41.9 Example 71 Inv-71 Compound 1 6.65 544 41.1 Example 72 Inv-72 Compound 1 6.73 542 42.3 Example 73 Inv-73 Compound 1 6.75 544 42.2 Example 74 Inv-74 Compound 1 6.65 543 41.2 Example 75 Inv-75 Compound 1 6.74 547 42.7 Example 76 Inv-76 Compound 1 6.72 547 41.3 Example 77 Inv-77 Compound 1 6.82 547 42.5 Example 78 Inv-78 Compound 1 6.65 545 41.1 Example 79 Inv-79 Compound 1 6.65 547 41.0 Example 82 Inv-82 Compound 1 6.73 547 42.0 Example 81 Inv-81 Compound 1 6.73 545 41.5 Example 82 Inv-82 Compound 1 6.65 546 42.2 Example 83 Inv-83 Compound 1 6.74 544 41.8 Example 84 Inv-84 Compound 1 6.72 546 41.3 Example 85 Inv-85 Compound 1 6.69 547 42.1 Example 86 Inv-86 Compound 1 6.65 546 42.0 Example 87 Inv-87 Compound 1 6.62 544 41.3 Example 88 Inv-88 Compound 1 6.66 543 41.1 Example 89 Inv-89 Compound 1 6.59 547 40.1 Example 92 Inv-92 Compound 1 6.62 545 41.9 Example 91 Inv-91 Compound 1 6.65 548 41.1 Example 92 Inv-92 Compound 1 6.62 544 40.3 Example 93 Inv-93 Compound 1 6.72 541 42.2 Example 94 Inv-94 Compound 1 6.65 545 41.2 Example 95 Inv-95 Compound 1 6.64 542 40.7 Example 96 Inv-96 Compound 1 6.59 542 41.3 Example 97 Inv-97 Compound 1 6.55 544 40.8 Example 98 Inv-98 Compound 1 6.55 543 41.1 Example 99 Inv-99 Compound 1 6.68 543 40.8 Example 100 Inv-100 Compound 1 6.72 544 40.9 Example 101 Inv-101 Compound 1 6.65 545 41.1 Example 102 Inv-102 Compound 1 6.72 544 42.3 Example 103 Inv-103 Compound 1 6.72 544 42.2 Example 104 Inv-3 Compound 9 6.65 541 41.8 Example 105 Inv-5 Compound 9 6.52 542 42.7 Example 106 Inv-6 Compound 9 6.65 542 41.5 Example 107 Inv-7 Compound 9 6.69 542 42.5 Example 108 Inv-8 Compound 9 6.62 543 41.9 Example 109 Inv-18 Compound 9 6.55 542 42.0 Example 110 Inv-21 Compound 9 6.59 541 42.0 Example 111 Inv-23 Compound 9 6.72 541 41.5 Example 112 Inv-30 Compound 9 6.72 541 42.2 Example 113 Synthesis of Inv-31 Compound 9 6.65 543 41.8 Example 114 Inv-87 Compound 9 6.59 545 41.3 Example 115 Inv-3 Compound 149 6.62 522 42.1 Example 116 Inv-5 Compound 149 6.71 519 41.7 Example 117 Inv-6 Compound 149 6.65 517 41.3 Example 118 Inv-7 Compound 149 6.62 518 41.1 Example 119 Inv-8 Compound 149 6.64 517 42.1 Example 122 Inv-18 Compound 149 6.59 522 41.9 Example 121 Inv-21 Compound 149 6.62 518 41.1 Example 122 Inv-23 Compound 149 6.64 519 42.3 Example 123 Inv-30 Compound 149 6.62 521 42.2 Example 124 Inv-31 Compound 149 6.62 522 41.2 Example 125 Inv-87 Compound 149 6.72 522 42.7 Comparative Example 1 CBP Ir (ppy) ₃ 6.93 516 38.2

As shown in Table 1, compounds (Inv-1 to Inv-103) according to the present invention were used as hosts of organic electroluminescent devices and compounds (compounds 1, 9 and 149) When the light emitting layer is used as a dopant, the organic electroluminescent device using the CBP exhibits superior performance in terms of efficiency and driving voltage as compared with the organic electroluminescent device using the conventional CBP (Comparative Example 1), and has various emission wavelengths depending on the dopant.

[ Evaluation example  2]

The driving voltage, the emission peak and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 126-131 and Comparative Example 2. The results are shown in Table 2 below.

Sample Host Dopant The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 126 Inv-18 Compound 164 6.60 610 14.4 Example 127 Inv-104 Compound 164 6.55 612 43.9 Example 128 Inv-105 Compound 164 6.52 619 14.2 Example 129 Inv-106 Compound 164 6.65 617 13.5 Example 130 Inv-107 Compound 164 6.72 618 13.7 Example 131 Inv-108 Compound 164 6.68 617 13.1 Comparative Example 2 CBP Ir (piq) ₂ (acac) 5.25 620 8.2

As shown in Table 2, the compounds (Inv-18, Inv-104 to Inv-108) according to the present invention were used as hosts of organic electroluminescent devices, It can be seen that the organic electroluminescent device of the present invention exhibits superior performance in terms of efficiency and driving voltage as compared with the organic electroluminescent device using the conventional CBP (Comparative Example 2).

Claims (8)

anode; cathode; And at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic material layers comprises a compound selected from the group consisting of compounds represented by the following formulas (1a) to (1f) and a compound represented by the following formula (3)
[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

&Lt; RTI ID = 0.0 &

[Formula 1e]

(1f)

In the above general formulas (1a) to (1f)
X ₁ and X ₂ are each independently S or N (Ar ₁ ), wherein at least one of X ₁ and X ₂ is N (Ar ₁ )
R ₁ to R ₄ and Ar ₁ are each independently, hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an alkenyl group of an amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of the group, C ₂ ~ C ₄₀ the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60, a plurality of R ₃ are the same or different, , Plural R &lt; ₄ &gt; s are the same or different from each other,
Wherein R ₁ to R ₄ and an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boronic of Ar ₁ A halogen atom, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkene group, an aryloxy group, an aryloxy group, A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group , C group ₆ to C ₆₀ aryl boron, C ₆ to C ₆₀ aryl phosphine of pingi, C ₆ to C ₆₀ aryl phosphine oxide group, and a C ₆ to C ₆₀ aryl amine group selected from the group consisting of 1 It may be substituted with at least,
(3)

In Formula 3,
X is an organic ligand, X is a heteroaryl group having 3 to 40 nuclear atoms, Y is an aryl group having ₆ to ₄₀ carbon atoms or a heteroaryl group having 3 to 40 nuclear atoms,
R ₁₁ to R ₁₈ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, An alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine of C ₆₀ is selected from the group consisting of pins oxide groups and C ₆ ~ C ₆₀ aryl amine, combine adjacent groups may form a fused ring,
n is an integer of 1 to 3; delete The method according to claim 1,
Wherein the compound represented by Formula 3 is selected from the group consisting of compounds represented by the following Chemical Formulas 3a to 3d:
[Chemical Formula 3]

(3b)

[Chemical Formula 3c]

(3d)

Wherein X, Y, n and R &lt; ₁₁ &gt; to R &lt; ₁₈ &gt; are as defined in claim 1,
Wherein Ra and R ₂₁ to R ₂₅ each independently represent hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ An arylsilyl group of C ₆ to C ₆₀ , a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ An arylphosphine oxide group and an arylamine group having ₆ to ₆₀ carbon atoms, and may be bonded to adjacent groups to form a condensed ring,
M is an integer of 0 to 3; delete The method according to claim 1,
The organic electroluminescent device, characterized in that said Ar ₁ is selected from the group consisting of an arylamine C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ C _60. The method according to claim 1,
Wherein XY in Formula 3 is selected from the group consisting of structures represented by the following Al to A24:

The R ₃₁ to R ₄₂ Are each independently, hydrogen, deuterium, a halogen, a cyano group, a nitro group, an amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ of for C ₆₀ aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ group C ₆₀ aryl silyl group, C ₁ ~ alkyl boron C ₄₀ of, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C of An arylamine group having ₆ to ₆₀ carbon atoms, and may be bonded to adjacent groups to form a condensed ring. The method according to claim 1,
Wherein the organic compound layer comprising a compound selected from the group consisting of the compounds represented by the above formulas (1a) to (1f) and the compound represented by the above formula (3) is selected from the group consisting of a hole injecting layer, a hole transporting layer and a light emitting layer device. The method according to claim 1,
The organic compound layer including the compound represented by the above Chemical Formulas 1a to 1f and the compound represented by the Chemical Formula 3 is a light emitting layer,
Wherein the compound selected from the group consisting of the compounds represented by Chemical Formulas 1 a to 1f is a host material of the light emitting layer and the compound represented by Chemical Formula 3 is a dopant material of the light emitting layer.