WO2014065498A1 - Organic electroluminescent device - Google Patents

Abstract

The present invention relates to an organic electroluminescent device, in which a light-emitting layer using an indole-based compound and an iridium compound as a host material and dopant material, respectively, is introduced into the organic electroluminescent device so that the organic electroluminescent device can be provided with improved luminous efficiency, driving voltage, life characteristics, and the like.

Description

Organic electroluminescent element

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

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer, holes and electrons meet to form an exciton, and when the exciton falls to the ground, it shines. do. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

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

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of phosphorescent dopants, in theory, can improve the luminous efficiency up to four times compared to fluorescent dopants, and therefore, research has been conducted on phosphorescent dopants as well as phosphorescent hosts.

Hole transport material to date. NPB, BCP, Alq ₃ and the like are known as hole injection materials and electron transport materials, and anthracene derivatives are known as light emitting materials. Among the light emitting materials, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ are blue, green, and red phosphorescent dopant materials. CBP is used as a phosphorescent host material.

However, the conventional luminescent material has good luminescence properties, but the glass transition temperature is low, so the thermal stability is not good, and thus it is not a satisfactory level in terms of the lifetime of the organic EL device. Therefore, there is a demand for the development of an organic electroluminescent device including a light emitting material having excellent performance.

An object of the present invention is to provide an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifetime in order to solve the above problems.

The present invention to achieve the above object; cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by Formula 1 and a compound represented by Formula 3 below. It provides an organic electroluminescent device.

[Formula 1]

In Chemical Formula 1,

Y ₁ to Y ₄ are each independently N or CR ₃ , and _one of Y ₁ and Y ₂ , Y ₂ and Y ₃ , or Y ₃ and Y ₄ forms a condensed ring represented by the following Chemical Formula 2,

[Formula 2]

In Chemical Formula 2,

The dotted line means a site where condensation occurs with the compound of Formula 1, and Y ₅ to Y ₈ are each independently 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 ), wherein At least one of X ₁ and X ₂ is N (Ar ₁ ),

R ₁ to R ₄ and Ar ₁ to Ar ₅ are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C Alkynyl group of ₂ to C ₄₀ , cycloalkyl group of C ₃ to C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ 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 an adjacent group 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, arylsilyl group of R ₁ to R ₄ and Ar ₁ to Ar ₅ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 Heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, 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 May be substituted with one or more selected

[Formula 3]

In Chemical Formula 3,

XY is an organic ligand, X is an aryl heteroaryl of nuclear atoms of 3 to 40 group, Y is a C ₆ ~ C ₄₀ heteroaryl group of the aryl group or nuclear atoms of 3 to 40, R ₁₁ to R ₁₈ are each Independently, hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ the aryl group, the number of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ 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 ~ It is selected from the group consisting of C ₆₀ arylamine groups, may be bonded to adjacent groups to form a condensed ring, n is an integer of 1 to 3.

Alkyl used in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl , Pentyl, iso-amyl, hexyl and the like.

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

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

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.

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 preferably at least one carbon in the ring, preferably 1 To 3 carbons are substituted with a hetero atom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine and the like.

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 alone or in combination of two or more rings. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, triphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, indenyl and the like.

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 at least one carbon in the ring, preferably 1 to 3 Carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

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

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

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, and arylamine is substituted with aryl having 6 to 60 carbon atoms. Amine.

As used herein, the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Hereinafter, the present invention will be described.

The present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is a compound represented by Formula 1 and the It provides an organic electroluminescent device comprising a compound represented by the formula (3).

Compound represented by the formula (1) is a condensed carbon ring or a condensed heterocyclic moiety, preferably a condensed heterocyclic moiety is connected to the indole-based skeleton, the energy level is controlled by a number of substituents wide band gap (sky blue ~ red) Therefore, when the compound represented by Formula 1 is used in the organic material layer of the organic electroluminescent device, the phosphorescence property may be improved, and the electron and / or hole transport ability and the light emitting ability may be enhanced.

Herein, the compound represented by Formula 1 of the present invention is preferably used in the hole transport layer, the electron transport layer and the light emitting layer of the organic material layer, and because of the indole-based skeleton exhibits excellent properties as a light emitting host material compared to the conventional CBP, More preferably used as the host material.

Specifically, the compound represented by Chemical Formula 1 has various aromatic rings bonded to the indole-based backbone as a substituent to significantly increase the molecular weight of the compound, thereby improving glass transition temperature and higher thermal stability than conventional CBP. Can have In addition, since the whole molecule has a bipolar (bipolar) nature of the various aromatic ring substituents, the binding force between the holes and the electrons can be increased, and thus it can exhibit excellent characteristics as a host material of the light emitting layer compared to the conventional CBP.

It is preferable that all of the compounds represented by the formula (1) that do not form a condensed ring in Y ₁ to Y ₄ is CR ₃ , wherein a plurality of R ₃ may be the same or different from each other. In addition, it is preferable that all of Y ₅ to Y ₈ of the compound represented by Formula 1 are CR ₄ , and at this time, a plurality of R ₄ may be identical to or different from each other.

On the other hand, considering the wide band-gap and thermal stability of the compound, R ₁ to R ₄ of Formula 1 are each independently hydrogen, an aryl group of C ₆ ~ C ₆₀ (eg phenyl, naphthyl, bis Phenyl) or a heteroaryl group having 5 to 60 nuclear atoms (for example, pyridine).

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

[Formula 1a]

[Formula 1b]

[Formula 1c]

[Formula 1d]

[Formula 1e]

[Formula 1f]

In Formulas 1a to 1f, X ₁ , X ₂ and R ₁ to R ₄ are the same as defined above.

On the other hand, in consideration of characteristics such as luminous efficiency, driving voltage, and lifespan of the organic EL device, X ₁ and X ₂ of Formula 1 are each independently N (Ar ₁ ) or S is preferred. That is, it is preferable that X ₁ is N (Ar ₁ ) and X ₂ is S, X ₁ is S and X ₂ is N (Ar ₁ ), or both X ₁ and X ₂ are N (Ar ₁ ).

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

In Formulas C1 to C66, R ₁ to R ₄ are as defined above, wherein 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 It is preferable. Specifically, Ar ₁ to Ar ₅ are each independently selected from the following substituent (functional group) groups (S1-S192).

Meanwhile, the compound represented by Chemical Formula 3 has an iridium (Ir) as its center, and an aromatic ring is connected to one side, and an organic ligand is connected to the other side. The compound represented by Formula 3 of the present invention may increase the energy gap between the HOMO and triplet MLCT states because the organic ligand is linked. Therefore, when the compound represented by Chemical Formula 3 is used in the organic material layer of the organic EL device, specifically, the hole injection layer, the hole transport layer, and the light emitting layer, phosphorescence characteristics may be improved and color purity may be increased.

In particular, when used in the organic electroluminescent device with the compound represented by the formula (1) can improve the performance. That is, the light emitting layer of the organic material layer of the organic EL device is made of a host / dopant material, the present invention is a compound represented by the formula (1) as a host material of the light emitting layer so that energy can be efficiently transferred between the host / dopant, By using the compound represented by Formula 3 as a dopant material of the light emitting layer, it is possible to provide an organic EL device having excellent color purity as well as driving voltage, luminous efficiency, and lifetime characteristics.

In the compound represented by the 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- and containing heteroaryl group, Y is a heteroaryl group of C ₆ ~ C ₄₀ aryl group or a nuclear atoms of 3 to 40.

The aryl group or heteroaryl group of X and Y is halogen, cyano group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₂ ~ C 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 It may be substituted by. In addition, the substituents may be bonded to adjacent groups 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 compound represented by the formulas (3a to 3d).

[Formula 3a]

[Formula 3b]

[Formula 3c]

[Formula 3d]

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

Ra and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 Heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ Is selected from the group consisting of an aryl phosphine oxide group and an arylamine group of C ₆ ~ C ₆₀ , may be combined with adjacent groups to form a condensed ring, wherein m is an integer of 0 to 3.

X-Y, which is an organic ligand in Chemical Formula 3, is preferably selected from the group consisting of structures represented by A1-A24 in consideration of characteristics of the organic electroluminescent device.

R ₃₁ to R ₄₂ of the structure represented by A1 to A24 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having ₆ to C ₆₀ atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having ₁ to C ₄₀ atoms, aryl jade having ₆ to C ₆₀ atoms group, C ₁ ~ 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 ~ aryl phosphine of C ₆₀ It is selected from the group consisting of a pin group, a C ₆ ~ C ₆₀ aryl phosphine oxide group and a C ₆ ~ C ₆₀ arylamine group, it may be combined with adjacent groups to form a condensed ring.

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

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

Meanwhile, the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and any one or more of the one or more organic material layers may be represented by the above chemical formula. Except for including the compounds represented by 1 and 3 may be made of materials and structures known in the art.

Specifically, the organic EL device of the present invention may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. It may also be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode (anode or cathode) and the organic material layer.

At least one of the hole injection layer, the hole transport layer, and the light emitting layer corresponding to the organic material layer may preferably include a compound represented by Chemical 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.

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

The anode material may be a metal such as vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black and the like can be used.

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

In addition, the electron injection layer and the electron transport layer may be used without particular limitation as long as it is a material known in the art.

The manufacturing method of the organic EL device of the present invention is not particularly limited as long as it is known in the art, but the organic material layer may be formed by a vacuum deposition method or a solution coating method. Here, examples of the solution coating method may include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer.

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

Preparation Example 1 Synthesis of IC-1

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

5-bromo-1H-indole (25 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3) under nitrogen stream , 2-dioxaborolane) (48.58 g, 0.191 mol), Pd (dppf) Cl ₂ (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) were mixed and 130 ° C Stir at 12 h.

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

¹ H-NMR: δ 1.24 (s, 12H), 6.45 (d, 1H), 7.27 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.95 (s, 1H), 8.21 ( s, 1 H)

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

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22) under nitrogen stream 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%) was added at 40 ° C. Put and stirred at 80 ℃ for 12 hours.

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

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, 1H), 8.00 (d, 1H), 8.09 (t, 1H), 8.20 (s, 1H)

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

5- (2-nitrophenyl) -1H-indole (11 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol), 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, 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, which was freed of water, and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give 5- (2-nitrophenyl) -1-phenyl-1H-indole (10.30 g, yield). 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, 1H), 8.01 (d, 1H), 8.11 (t, 1H)

Step 4 Synthesis of IC-1

Mix the above 5- (2-nitrophenyl) -1-phenyl-1H-indole (5 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1,2-dichlorobenzene (50 ml) under nitrogen stream for 12 hours Was stirred.

After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed with MgSO ₄ and the resulting organic layer was 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 ( m, 5H), 7.85 (d, 1H), 8.02 (d, 1H), 10.59 (s, 1H)

Preparation Example 2 Synthesis of IC-2

Using the 5- (2-nitrophenyl) -1-phenyl-1H-indole, triphenylphosphine and 1,2-dichlorobenzene, the same process as in <Step 4> of Preparation Example 1 was performed, and the IC-1 and the isomer of IC are structural isomers. -2 was obtained.

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 ( m, 5H), 7.84 (d, 1H), 8.03 (s, 1H), 10.58 (s, 1H)

Preparation Example 3 Synthesis of IC-3

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

Except for using 6-bromo-1H-indole instead of 5-bromo-1H-indole by following the same procedure as in <Step 1> of Preparation Example 1 6- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) -1H-indole was obtained.

¹ H-NMR: δ 1.25 (s, 12H), 6.52 (d, 1H), 7.16 (d, 1H), 7.21 (d, 1H), 7.49 (d, 1H), 7.53 (s, 1H), 8.15 ( s, 1 H)

Step 2 Synthesis of 6- (2-nitrophenyl) -1H-indole

5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole instead of 6- (4,4,5,5-tetramethyl-1,3,2- Except for using dioxaborolan-2-yl) -1H-indole was carried out the same procedure as in <Step 2> of Preparation Example 1 to obtain 6- (2-nitrophenyl) -1H-indole.

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, 1H), 7.66 (d, 1H), 7.78 (d, 1H), 8.19 (s, 1H)

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

Except for using the 6- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1H-indole was carried out the same process as in <Step 3> of Preparation Example 6 6- (2 -nitrophenyl) -1-phenyl-1H-indole was obtained.

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, 1H), 8.02 (d, 1H)

Step 4 Synthesis of IC-3

Except for using the 6- (2-nitrophenyl) -1-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole is the same as in <Step 4> of Preparation Example 1 The procedure was followed to obtain IC-3.

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, 1H), 9.81 (s, 1H)

Preparation Example 4 Synthesis of IC-4

Except for using the 6- (2-nitrophenyl) -1-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole is the same as in <Step 4> of Preparation Example 1 The procedure was followed 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, 1H), 9.82 (s, 1H)

Preparation Example 5 Synthesis of IC-5

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

Except for using 4-bromo-1H-indole instead of 5-bromo-1H-indole by performing the same process as in <Step 1> of Preparation Example 1 4- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) -1H-indole was obtained.

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

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

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 , 1H), 8.04 (d, 1H), 8.24 (s, 1H)

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

Except for using 4- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1H-indole, the same procedure as in <Step 3> of Preparation Example 1 was performed. nitrophenyl) -1-phenyl-1H-indole was obtained.

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 , 1H), 7.89 (m, 2H), 8.00 (d, 1H), 8.06 (d, 1H)

Step 4 Synthesis of IC-5

The same procedure as in <Step 4> of Preparation Example 1, except that 4- (2-nitrophenyl) -1-phenyl-1H-indole is used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole. Was carried out 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 , 1H), 7.88 (m, 2H), 8.01 (d, 1H), 8.04 (d, 1H), 8.23 (s, 1H)

Preparation Example 6 Synthesis of IC-6

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

Except for using 7-bromo-1H-indole instead of 5-bromo-1H-indole by following the same procedure as in <Step 1> of Preparation Example 1 7- (4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl) -1H-indole was obtained.

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)

Step 2 Synthesis of 7- (2-nitrophenyl) -1H-indole

5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole instead of 7- (4,4,5,5-tetramethyl-1,3,2- Except for using dioxaborolan-2-yl) -1H-indole was carried out the same process as <step 2> of Preparation Example 1 to obtain 7- (2-nitrophenyl) -1H-indole.

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 , 1H), 8.11 (d, 1H), 8.23 (s, 1H)

<Step 3> Synthesis of 7- (2-nitrophenyl) -1-phenyl-1H-indole

Except for using 7- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1H-indole, the same procedure as in <Step 3> of Preparation Example 1 was performed to obtain 7- (2- nitrophenyl) -1-phenyl-1H-indole was obtained.

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 , 1H), 8.10 (d, 1H)

Step 4 Synthesis of IC-6

The same procedure as in <Step 4> of Preparation Example 1, except that 7- (2-nitrophenyl) -1-phenyl-1H-indole is used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole. Was carried out 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 , 1H), 8.00 (d, 1H), 8.09 (d, 1H), 8.22 (s, 1H)

Preparation Example 7 Synthesis of IC-7

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

Except for using 2,4-dibromo-1-nitrobenzene instead of 1-bromo-2-nitrobenzene, the process was carried out in the same manner as in <Step 2> of Preparation Example 1 to 5- (5-bromo-2-nitrophenyl)- 1H-indole was obtained.

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 , 1H), 8.13 (s, 1H), 8.21 (s, 1H)

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

Except for using 5- (5-bromo-2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1H-indole was carried out in the same manner as in <Step 3> of Preparation Example 5 -(5-bromo-2-nitrophenyl) -1-phenyl-1H-indole was obtained.

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 , 1H), 8.11 (s, 1H)

Step 3 Synthesis of IC-7

<Step 4 of Preparation Example 1 except for using the 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-7 was obtained by following the same procedure as>.

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, 1H), 7.85 (d, 1H), 8.10 (s, 1H), 8.23 (s, 1H)

Preparation Example 8 Synthesis of IC-8

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

2,4-dibromo-1-nitrobenzene and 6- instead of 1-bromo-2-nitrobenzene and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole Except for using (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole, the same procedure as in <Step 2> of Preparation Example 1 was performed. (5-bromo-2-nitrophenyl) -1H-indole was obtained.

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 , 1H), 8.14 (s, 1H), 8.25 (s, 1H)

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

Except for using 6- (5-bromo-2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1H-indole was carried out in the same manner as in <Step 3> of Preparation Example 6 -(5-bromo-2-nitrophenyl) -1-phenyl-1H-indole was obtained.

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 , 1H), 8.16 (s, 1H)

Step 3 Synthesis of IC-8

<Step 4 of Preparation Example 1 except for using the 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-8 was obtained by following the same procedure as>.

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, 1H), 7.87 (d, 1H), 8.12 (s, 1H), 8.25 (s, 1H)

Preparation Example 9 Synthesis of IC-9

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

A 5- (2-nitrophenyl) -1-o-tolyl-1H-indole was obtained in the same manner as in <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, 1H), 7.94 (s, 1H), 8.00 (d, 1H), 8.12 (t, 1H)

Step 2 Synthesis of IC-9

Except for using the 5- (2-nitrophenyl) -1-o-tolyl-1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole and <Step 4> of Preparation Example 1 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, 1H), 7.61 (m, 4H), 7.86 (d, 1H), 8.01 (d, 1H), 10.58 (s, 1H)

Preparation Example 10 Synthesis of IC-10

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

A 1- (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 instead 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, 1H)

<Step 2> Synthesis of IC-10

Except for using 1- (biphenyl-4-yl) -5- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole < IC-10 was obtained by the same procedure as in step 4>.

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 ( m, 3H), 7.76 (d, 2H), 7.85 (d, 1H), 10.45 (s, 1H)

Preparation Example 11 Synthesis of IC-11

Step 1 Synthesis of IC-11-1

Except for using 1-bromo-3,5-diphenyl benzene instead of iodobenzene to obtain IC-11-1 by the same process as in <Step 3> of Preparation Example 1.

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, 4H), 7.87 (m, 4H), 7.93 (d, 1H), 7.99 (d, 1H)

Step 2 Synthesis of IC-11

Except for using IC-11-1 instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole, IC-11 was obtained by the same process as <Step 4> of Preparation Example 1.

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, 4H), 7.86 (m, 3H), 7.92 (d, 1H), 7.98 (d, 1H), 10.60 (s, 1H)

Preparation Example 12 Synthesis of IC-12

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

Except for using 1-bromo-2- (trifluoromethyl) benzene instead of iodobenzene, the same process as in <Step 3> of Preparation Example 1 was carried out to give 5- (2-nitrophenyl) -1- (2- (trifluoromethyl) phenyl ) -1H-indole was obtained.

¹ H-NMR: δ 6.48 (d, 1H), 7.26 (d, 1H), 7.47 (m, 3H), 7.57 (m, 3H), 7.63 (t, 1H), 7.84 (t, 1H), 7.95 ( s, 1H), 8.01 (d, 1H), 8.13 (t, 1H)

Step 2 Synthesis of IC-12

Preparation Example 1 except that 5- (2-nitrophenyl) -1- (2- (trifluoromethyl) phenyl) -1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole 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 ( m, 4H), 7.85 (d, 1H), 8.01 (d, 1H), 10.57 (s, 1H)

Preparation Example 13 Synthesis of IC-13

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

A 1- (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, 1H)

<Step 2> Synthesis of IC-13

Except for using 1- (biphenyl-3-yl) -5- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole, IC-13 was obtained by performing the same procedure as in Step 4>.

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, 1H), 10.44 (s, 1H)

Preparation 14 Synthesis of IC-14

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

The same procedure as in <Step 3> of Preparation Example 1 was performed except that 6- (2-nitrophenyl) -1H-indole and 3-bromobiphenyl were used instead of 5- (2-nitrophenyl) -1H-indole and iodobenzene. 1- (biphenyl-3-yl) -6- (2-nitrophenyl) -1H-indole was obtained.

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, 1H)

Step 2 Synthesis of IC-14

Preparation Example 1 except that 1- (biphenyl-3-yl) -6- (2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-14 was obtained by 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 ( m, 3H), 7.76 (m, 2H), 7.85 (d, 1H), 10.43 (s, 1H)

Preparation Example 15 Synthesis of IC-15

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

The same procedure as in <Step 3> of Preparation Example 1 was performed except that 6- (2-nitrophenyl) -1H-indole and 4-bromobiphenyl were used instead of 5- (2-nitrophenyl) -1H-indole and iodobenzene. 1- (biphenyl-4-yl) -6- (2-nitrophenyl) -1H-indole was obtained.

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, 1H)

Step 2 Synthesis of IC-15

Preparation Example 1 except that 1- (biphenyl-4-yl) -6- (2-nitrophenyl) -1H-indole is used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-15 was obtained by performing the same procedure as in <Step 4>.

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, 1H), 10.46 (s, 1H)

Preparation Example 16 Synthesis of IC-16

<Step 1> Synthesis of IC-16-1

<Step 3 of Preparation Example 1 except that 6- (2-nitrophenyl) -1H-indole and 1-bromo-3,5-diphenyl benzene were used instead of 5- (2-nitrophenyl) -1H-indole and iodobenzene. IC-16-1 was obtained by following the same procedure as>.

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, 4H), 7.86 (m, 4H), 7.92 (d, 1H), 7.98 (d, 1H)

Step 2 Synthesis of IC-16

Except for using the IC-16-1 instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole was carried out the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-16.

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, 4H), 7.86 (m, 3H), 7.92 (d, 1H), 7.98 (d, 1H), 10.59 (s, 1H)

Preparation 17 Synthesis of IC-17

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

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

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, 1H), 8.01 (d, 1H)

<Step 2> Synthesis of IC-17

Preparation Example 1 except that 6- (2-nitrophenyl) -1- (3- (trifluoromethyl) phenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-17 was obtained by the same procedure as in <Step 4>.

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, 1H), 9.82 (s, 1H)

Preparation Example 18 Synthesis of IC-18

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

<Step of Preparation Example 1 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> was carried out in the same manner to obtain 3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9-phenyl-9H-carbazole.

GC-Mass (Theoretical value: 479.16 g / mol, Measured value: 479 g / mol)

<Step 2> Synthesis of IC-18

Except for using 3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9-phenyl-9H-carbazole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole Was obtained in the same manner as in <Step 4> of Preparation Example 1 to obtain an IC-18.

GC-Mass (Theoretical value: 447.17 g / mol, Measured value: 447 g / mol)

Preparation Example 19 Synthesis of IC-19

<Step 1> of 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (5- (2-nitrophenyl) -1H-indol-1-yl) -9H-carbazole synthesis

6- (2-nitrophenyl) -1H-indole and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl instead of 5- (2-nitrophenyl) -1H-indole and iodobenzene Except for using) -9H-carbazole, 9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- was carried out in the same manner as in <Step 3> of Preparation Example 1 (5- (2-nitrophenyl) -1H-indol-1-yl) -9H-carbazole was obtained.

GC-Mass (Theoretical value: 634.21 g / mol, Measured value: 634 g / mol)

<Step 2> 3- (9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol-3-yl) -3,10-dihydropyrrolo [3,2-a] Synthesis of carbazole

9- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (5- (2-nitrophenyl)-instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole Except for using 1H-indol-1-yl) -9H-carbazole was carried out the same process as in <Step 4> of Preparation Example 1 to obtain an IC-19.

GC-Mass (Theoretical value: 602.22 g / mol, Measured value: 602 g / mol)

Preparation Example 20 Synthesis of IC-20

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

5-bromo-1H-indole (25 g, 0.13 mol), iodobenzene (31.22 g, 0.15 mol), Pd (OAc) ₂ (1.43 g, 5 mol%), Triphenylphosphine (1.67 g, 5 mol%) under nitrogen stream , KOAc (37.55 g, 0.38 mol) and H ₂ O (300 ml) were mixed and stirred at 110 ° C. for 24 h.

After the reaction was completed, the mixture was extracted with ethyl acetate and then dried with MgSO ₄ , purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5-bromo-2-phenyl-1H-indole ( 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, 2H), 11.74 (s, 1H)

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

2-nitrophenylboronic acid (11.04 g, 66.14 mmol) and 5-bromo-2-phenyl-1H-indole (15 g, 55.12 mmol), NaOH (6.61 g, 165.36 mmol) and THF / H ₂ O 200 ml / 100 ml) was mixed, Pd (PPh ₃ ) ₄ (3.18 g, 5 mol) was added at 40 ° C., and the mixture was stirred at 80 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to give 5- (2-nitrophenyl) -2-phenyl-1H-indole (10.74 g, yield 62%). Got.

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)

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

Except for using the 5- (2-nitrophenyl) -2-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1H-indole was carried out in the same manner as in <Step 3> of Preparation Example 5 -(2-nitrophenyl) -1,2-diphenyl-1H-indole was obtained.

GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

Step 4 Synthesis of IC-20

<Step 4> of Preparation Example 1, except that 5- (2-nitrophenyl) -1,2-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole. IC-20 was obtained by performing the same procedure as in the following.

GC-Mass (Theoretical value: 358.15 g / mol, Measured value: 358 g / mol)

Preparation Example 21 Synthesis of IC-21

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

Except for using 6-chloro-1H-indole and bromobenzene instead of 5-bromo-1H-indole and iodobenzene 6-chloro-2-phenyl-1H was carried out in the same manner as in <Step 1> of Preparation Example 20 got -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, 2H), 11.68 (s, 1H)

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

Except for using the 6-chloro-2-phenyl-1H-indole instead of 5-bromo-2-phenyl-1H-indole was carried out the same process as in <Step 2> of Preparation Example 20 6- (2 -nitrophenyl) -2-phenyl-1H-indole was obtained.

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, 1H)

Step 3 Synthesis of 6- (2-nitrophenyl) -1,2-diphenyl-1H-indole

Except for using 6- (2-nitrophenyl) -2-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1H-indole was carried out in the same manner as in <Step 3> of Preparation Example 6 -(2-nitrophenyl) -1,2-diphenyl-1H-indole was obtained.

GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

Step 4 Synthesis of IC-21

<Step 4 of Preparation Example 1> except that 6- (2-nitrophenyl) -1,2-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-21 was obtained by performing the same procedure as in the following.

GC-Mass (Theoretical value: 358.15 g / mol, Measured value: 358 g / mol)

Preparation Example 22 Synthesis of IC-22

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

6-chloro-1H-indole (25 g, 0.17 mol), bromobenzene (31.19 g, 0.20 mol), Pd (OAc) ₂ (1.86 g, 5 mol), Triphenylphosphine (2.17 g, 5 mol%), under nitrogen stream 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 completion of the reaction, the mixture was extracted with ethyl acetate, followed by removing water with MgSO ₄ , and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 6-chloro-3-phenyl-1H-indole ( 24.5 g, yield 65%) was obtained.

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)

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

Except for using the 6-chloro-3-phenyl-1H-indole instead of 5-bromo-2-phenyl-1H-indole was carried out the same procedure as in <Step 2> of Preparation Example 20 6- (2 -nitrophenyl) -3-phenyl-1H-indole was obtained.

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, 1H), 8.00 (d, 2H), 11.48 (s, 1H)

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

Except for using 6- (2-nitrophenyl) -3-phenyl-1H-indole instead of 5- (2-nitrophenyl) -1H-indole was carried out in the same manner as in <Step 3> of Preparation Example 6 -(2-nitrophenyl) -1,3-diphenyl-1H-indole was obtained.

GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

Step 4 Synthesis of IC-22

<Step 4> of Preparation Example 1, except that 6- (2-nitrophenyl) -1,3-diphenyl-1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole. IC-22 was obtained by performing the same procedure as in the following.

GC-Mass (Theoretical value: 358.15 g / mol, Measured value: 358 g / mol)

Preparation Example 23 Synthesis of IC-23

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

Except for using 5-bromo-2-phenyl-1H-indole instead of 6-chloro-1H-indole to perform the same process as in <Step 1> of Preparation Example 22 5-bromo-2,3-diphenyl -1 H-indole was obtained.

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-diphenyl-1H-indole

Except for using 5-bromo-2,3-diphenyl-1H-indole instead of 5-bromo-2-phenyl-1H-indole, the same procedure as in <Step 2> of Preparation Example 20 was performed. (2-nitrophenyl) -2,3-diphenyl-1H-indole was obtained.

GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

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

Except for using 5- (2-nitrophenyl) -2,3-diphenyl-1H-indole instead of 5- (2-nitrophenyl) -1H-indole, the same procedure as in <Step 3> of Preparation Example 1 was performed. 5- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was obtained.

GC-Mass (Theoretical value: 466.17 g / mol, Measured value: 466 g / mol)

Step 4 Synthesis of IC-23

<Step of Preparation Example 1 except that 5- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole IC-23 was obtained by the same procedure as 4>.

GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

Preparation Example 24 Synthesis of IC-24

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

Except for using 6-chloro-2-phenyl-1H-indole instead of 6-chloro-1H-indole was carried out the same process as in <Step 1> of Preparation Example 22 6-chloro-2,3-diphenyl -1 H-indole was obtained.

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)

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

Except for using the 6-chloro-2,3-diphenyl-1H-indole instead of 5-bromo-2-phenyl-1H-indole to perform the same process as in <Step 2> of Preparation Example 20 6- (2-nitrophenyl) -2,3-diphenyl-1H-indole was obtained.

GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

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

Except for using 6- (2-nitrophenyl) -2,3-diphenyl-1H-indole instead of 5- (2-nitrophenyl) -1H-indole, the same procedure as in <Step 3> of Preparation Example 1 was performed. To 6- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole.

GC-Mass (Theoretical value: 466.17 g / mol, Measured value: 466 g / mol)

Step 4 Synthesis of IC-24

<Step of Preparation Example 1 except that 6- (2-nitrophenyl) -1,2,3-triphenyl-1H-indole was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole. IC-24 was obtained by following the same procedure as 4>.

GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

Preparation Example 25 Synthesis of IC-25

<Step 1> Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole

6- (2-nitrophenyl) -1H-indole (10 g, 41.97 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (17.32 g, 50.37 mmol) under nitrogen stream , Pd (OAc) ₂ (0.47 g, 5 mol%), NaO (t-bu) (8.07 g, 83.95 mmol), P (t-bu) ₃ (0.85 g, 4.19 mmol) and Toluene (100 ml) Mix and stir at 110 ° C. for 12 h.

After completion of the reaction, the mixture was extracted with ethyl acetate and then dried with MgSO ₄ , purified by column chromatography (Hexane: EA = 3: 1 (v / v)), and purified by 1- (3- (4,6-diphenyl-). 1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole (15.8 g, yield 69%) was obtained.

GC-Mass (Theoretical value: 545.19 g / mol, Measured value: 545 g / mol)

<Step 2> Synthesis of IC-25

5- (2-nitrophenyl) -1-phenyl-1H-indole instead of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl Except for using) -1H-indole was carried out the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-25.

GC-Mass (Theoretical value: 513.20 g / mol, Measured value: 513 g / mol)

Preparation 26 Synthesis of IC-26

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

<Step of Preparation Example 25 except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. 1> was carried out in the same manner to obtain 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole.

GC-Mass (Theoretical value: 544.19 g / mol, Measured value: 544 g / mol)

<Step 2> Synthesis of IC-26

Using 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole Except for the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-26.

GC-Mass (Theoretical value: 512.20 g / mol, Measured value: 512 g / mol)

Preparation 27 Synthesis of IC-27

<Step 1> Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2- nitrophenyl) -1H-indole

Except for using 5- (2-nitrophenyl) -1H-indole instead of 6- (2-nitrophenyl) -1H-indole, 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitrophenyl) -1H-indole was obtained.

GC-Mass (Theoretical value: 545.19 g / mol, Measured value: 545 g / mol)

<Step 2> Synthesis of IC-27

5- (2-nitrophenyl) -1-phenyl-1H-indole instead of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -5- (2-nitrophenyl Except for using) -1H-indole was carried out the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-27.

GC-Mass (Theoretical value: 513.20 g / mol, Measured value: 513 g / mol)

Preparation Example 28 Synthesis of IC-28

<Step 1> Synthesis of 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -5- (2-nitrophenyl) -1H- indole

6- (2-nitrophenyl) -1H-indole and 2- (3 instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl)-was subjected to the same process as in <Step 1> of Preparation Example 25, except that -chlorophenyl) -4,6-diphenylpyrimidine was used. 5- (2-nitrophenyl) -1H-indole was obtained.

GC-Mass (Theoretical value: 544.19 g / mol, Measured value: 544 g / mol)

<Step 2> Synthesis of IC-28

Using 1- (3- (4,6-diphenylpyrimidin-2-yl) phenyl) -5- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole Except for the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-28.

GC-Mass (Theoretical value: 512.20 g / mol, Measured value: 512 g / mol)

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

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

Except for using 5-bromobenzo [b] thiophene instead of 5-bromo-1H-indole, 2- (benzo [b] thiophen-5-yl)-was carried out in the same manner as in <Step 1> of Preparation Example 1 4,4,5,5-tetramethyl-1,3,2-dioxaborolane was obtained.

¹ H NMR: δ 1.24 (s, 12H), 7.65 (d, 1H), 7.85 (d, 1H), 7.98 (d, 1H), 8.07 (d, 1H), 8.12 (s, 1H)

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

5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole instead of 2- (benzo [b] thiophen-5-yl) -4,4,5 A 5- (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: δ 7.67 (m, 2H), 7.88 (m, 2H), 7.98 (d, 1H), 8.00 (d, 1H), 8.07 (m, 2H), 8.13 (s, 1H)

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

The same procedure as in <Step 4> of Preparation Example 1 was performed except that 5- (2-nitrophenyl) benzo [b] thiophene was used instead of 5- (2-nitrophenyl) -1-phenyl-1H-indole. 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 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 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 Synthesis of IC-30

Step 1 Synthesis of 7- (2-nitrophenyl) benzo [b] thiophene

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 under a nitrogen stream Was added and stirred. 2.03 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the organic layer was filtered using column chromatography to obtain 7.38 g (28.9 mmol, yield 82%) of 7- (2-nitrophenyl) benzo [b] thiophene.

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

<Step 2> Synthesis of IC-30

Under nitrogen stream, 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 added thereto, followed by stirring for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was removed with water with MgSO ₄ , and obtained 3.29 g, (14.8 mmol, yield: 68%) of IC-30 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 Synthesis of IC-31a and IC-31b

Step 1 Synthesis of 6- (2-nitrophenyl) benzo [b] thiophene

Except for using 12.2 g (35.2 mmol) of 6-bromobenzo [b] thiophene instead of 7-bromobenzo [b] thiophene, 6- (2-nitrophenyl) benzo was prepared in the same manner as in <Step 1> of Preparation Example 30. 7.01 g of [b] thiophene were obtained (27.5 mmol, yield: 78%).

¹ H-NMR: δ 7.68 (m, 3H), 7.98 (m, 6H)

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

The same procedure as in <Step 2> of Preparation Example 30, except that 5.53 g (21.7 mmol) of 6- (2-nitrophenyl) benzo [b] thiophene was used instead of 7- (2-nitrophenyl) benzo [b] thiophene. 1.60 g (7.16 mmol, yield: 33%) of IC-31a and 1.79 g (8.03 mmol, yield: 37%) of IC-31b were obtained.

¹ H-NMR of IC-31a: 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 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 Synthesis of IC-32

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

Except for using 12.2 g (35.2 mmol) of 4-bromobenzo [b] thiophene instead of 7-bromobenzo [b] thiophene, 4- (2-nitrophenyl) benzo was subjected to the same procedure as in <Step 1> of Preparation Example 30. 7.28 g (28.5 mmol, yield: 81%) of [b] thiophene were obtained.

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

<Step 2> Synthesis of IC-32

The same procedure as in <Step 2> of Preparation Example 30, except that 5.53 g (21.7 mmol) of 4- (2-nitrophenyl) benzo [b] thiophene was used instead of 7- (2-nitrophenyl) benzo [b] thiophene. This yielded 3.05 g (13.7 mmol, yield: 63%) of IC-32.

¹ H-NMR: δ 7.31 (m, 2H), 7.73 (m, 4H), 7.96 (d, 1H), 8.10 (d, 1H), 8.26 (s, 1H)

Preparation 33 Synthesis of IC-33

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

5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole instead of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan Except for using 2-yl) -1H-indole and using 1-bromo-2-isopropylbenzene instead of 1-bromo-2-nitrobenzene, the same procedure as in <Step 2> of Preparation Example 1 was performed. (2-isopropylphenyl) -1H-indole was obtained.

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, 1H), 8.23 (s, 1H)

<Step 2> Synthesis of IC-33

Dissolve the 4- (2-isopropylphenyl) -1H-indole (5 g, 21.25 mmol) and RhCl (PPh ₃ ) ₃ (98.3 mg, 0.5 mol%) in 50 ml of 1,4-dioxane under nitrogen stream, and then 135 ° C. Stirred for 1 h.

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

¹ H NMR: δ 1.20 (s, 6H), 6.45 (d, 1H), 7.25 (d, 1H), 7.37 (m, 3H), 7.49 (d, 1H), 7.75 (d, 1H), 7.86 (d , 1H), 8.22 (s, 1H)

Preparation 34 Synthesis of IC-34

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

5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole instead of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan Except for using 2-yl) -1H-indole and using (2-bromophenyl) methylene) dibenzene instead of 1-bromo-2-nitrobenzene, the same procedure as in <Step 2> of Preparation Example 1 was performed. -(2-benzhydrylphenyl) -1H-indole was obtained.

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 , 1H), 8.21 (s, 1H)

<Step 2> Synthesis of IC-34

IC-34 was obtained by the same procedure as in <Step 2> of Preparation Example 33 using the 4- (2-benzhydrylphenyl) -1H-indole instead of 4- (2-isopropylphenyl) -1H-indole.

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 35 Synthesis of IC-35

Step 1 Synthesis of 6- (2-bromophenyl) -7-chloro-1H-indole

9.13 g (39.6 mmol) of 6-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 under nitrogen stream / H ₂ O was added and stirred. 2.29 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give 8.86 g (28.9 mmol, yield: 73%) of 6- (2-bromophenyl) -7-chloro-1H-indole.

¹ H-NMR: δ 6.45 (d, 1H), 7.35 (m, 3H), 7.74 (m, 3H), 8.06 (d, 1H), 8.64 (s, 1H)

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

7.45 g (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 , under a nitrogen stream 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 stirred at 110 ° C. for 15 hours.

After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 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, 2H), 8.06 (d, 1H), 8.60 (s, 1H)

<Step 3> Synthesis of IC-35

Under nitrogen stream, 6.34 g (15.4 mmol) ethyl 3- (2- (7-chloro-1H-indol-6-yl) phenylthio) propanoate, 2.60 g (23.2 mmol) potassium tert-butoxide were added to 100 ml THF. The mixture was stirred at 50 ° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain 2.30 g (10.3 mmol, yield: 67%) IC-35.

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 36 Synthesis of IC-36

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

5-bromobenzofuran (25 g, 0.126 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane under nitrogen stream ) (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 (500 ml) were mixed and 12 hours at 130 ° C. Was stirred.

After the reaction was completed, the mixture was extracted with ethyl acetate, followed by removing moisture with MgSO ₄ , and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to give 2- (benzofuran-5-yl) -4, 4,5,5-tetramethyl-1,3,2-dioxaborolane (23.23 g, yield 75%) was obtained.

¹ H-NMR: δ 1.25 (s, 12H), 6.46 (d, 1H), 7.28 (d, 1H), 7.43 (d, 1H), 7.53 (d, 1H), 7.98 (s, 1H)

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

1-bromo-2-nitrobenzene (15.86 g, 78.52 mmol) and 2- (benzofuran-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23 g, 94.23 mmol), K ₂ CO ₃ (32.56 g, 235.57 mmol) and 1,4-dioxane / H ₂ O (400 ml / 200 ml) were mixed and then Pd (PPh ₃ ) ₄ (4.54 g, 5 mol%) was added and stirred at 110 ° C. for 12 hours.

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

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, 1H), 8.01 (d, 1H), 8.06 (t, 1H)

Step 3 Synthesis of IC-36

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

After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed with MgSO _4, and the organic layer was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-36 (4.76 g, 55% yield).

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, 1H), 8.05 (t, 1H), 10.58 (s, 1H)

Preparation Example 37 Synthesis of IC-37

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

Except for using 6-bromobenzofuran instead of 5-bromobenzofuran was carried out the same process as in <Step 1> of Preparation Example 1 2- (benzofuran-6-yl) -4,4,5,5-tetramethyl-1 , 3,2-dioxaborolane was obtained.

¹ H-NMR: δ 1.25 (s, 12H), 6.46 (d, 1H), 7.28 (d, 1H), 7.43 (d, 1H), 7.53 (d, 1H), 7.98 (s, 1H)

Step 2 Synthesis of 6- (2-nitrophenyl) benzofuran

2- (benzofuran-6-yl) -4,4,5,5-tetramethyl-1 instead of 2- (benzofuran-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane A 6- (2-nitrophenyl) benzofuran was obtained in the same manner as in <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, 1H), 8.01 (d, 1H), 8.06 (t, 1H)

Step 3 Synthesis of IC-37

IC-37 was obtained by the same procedure as <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, 1H), 8.05 (t, 1H), 10.58 (s, 1H)

Preparation 38 Synthesis of IC-38

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

Dissolve 3-bromodibenzo [b, d] furan (7.41 g, 30.0 mmol) in THF 100 ml under nitrogen stream, add 28% aqueous ammonia (10.2 ml, 150 mmol) and Cu (0.10 g, 5 mol%). And stirred at 110 ° C. for 12 h. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. The solvent of the filtered organic layer was removed and 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)

Step 2 Synthesis of IC-38

Dibenzo [b, d] furan-3-amine (4.45 g, 24.29 mmol) was dissolved in H ₂ O / dioxane (10 ml / 90 ml) under a stream of nitrogen, followed by triethanolammonium chloride (0.45 g, 2.43 mmol) and RuCl _{3 `</sub> H <sub>2</sub> O (0.055 g, 0.2 mmol), PPh <sub>3</sub> (0.191 g, 0.7 mmol) and SnCl <sub>2`} 2H ₂ O (0.548 g, 2.43 mmol) were added thereto, followed by stirring at 180 ° C. for 20 hours. After completion of the reaction, the reaction mixture was poured into aqueous 5% HCl, extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to give 2.7 g (yield: 53%) of IC-38.

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 39 Synthesis of IC-39

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

The same procedure as in <Step 1> of Preparation Example 38 was performed except that 3-bromo-5,5-dimethyl-5H-dibenzo [b, d] silole was used instead of 3-bromodibenzo [b, d] furan. To 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, 1H), 7.64 (d, 1H), 7.91 (d, 1H)

<Step 2> Synthesis of IC-39

Except for using 5,5-dimethyl-5H-dibenzo [b, d] silol-3-amine instead of dibenzo [b, d] furan-3-amine, the same as in <Step 2> of Preparation Example 38 The procedure was followed to obtain IC-39.

¹ H-NMR: δ 0.66 (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, 1H), 7.89 (d, 1H), 7.97 (d, 1H), 10.42 (s, 1H)

Preparation 40 Synthesis of IC-40

Step 1 Synthesis of 5,5-diphenyl-5H-dibenzo [b, d] silol-3-amine

The same procedure as in <Step 1> of Preparation Example 38 was performed except that 3-bromo-5,5-diphenyl-5H-dibenzo [b, d] silole was used instead of 3-bromodibenzo [b, d] furan. To 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, 1H), 7.66 (d, 1H), 7.92 (d, 1H)

<Step 2> Synthesis of IC-40

Except for using the 5,5-diphenyl-5H-dibenzo [b, d] silol-3-amine instead of dibenzo [b, d] furan-3-amine, the same as in <Step 2> of Preparation Example 38 The procedure was followed to obtain IC-40.

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, 1H), 7.90 (d, 1H), 7.96 (d, 1H), 10.41 (s, 1H)

Preparation Example 41 Synthesis of IC-41

Except for using dibenzo [b, d] selenophen-3-amine instead of dibenzo [b, d] furan-3-amine, IC-41 was obtained by the same procedure as in <Step 2> of Preparation Example 38 above. .

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 Synthesis of IC-42

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

Except for using 5-bromobenzo [b] selenophene instead of 5-bromobenzofuran, the same procedure as in <Step 1> of Preparation Example 36 was carried out to give 2- (benzo [b] selenophen-5-yl) -4,4 , 5,5-tetramethyl-1,3,2-dioxaborolane was obtained.

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

2- (benzo [b] selenophen-5-yl) -4,4,5,5 instead of 2- (benzofuran-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane A 5- (2-nitrophenyl) benzo [b] selenophene was obtained by following the same procedure 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, 1H), 8.00 (d, 1H), 8.05 (t, 1H)

Step 3 Synthesis of IC-42

IC-42 was obtained by the same procedure as <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, 1H), 8.03 (t, 1H), 10.56 (s, 1H)

Preparation Example 43 Synthesis of IC-43

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

Except for using 6-bromobenzo [b] selenophene instead of 5-bromobenzofuran, the same procedure as in <Step 1> of Preparation Example 36 was carried out to give 2- (benzo [b] selenophen-6-yl) -4,4 , 5,5-tetramethyl-1,3,2-dioxaborolane was obtained.

¹ H-NMR: δ 1.24 (s, 12H), 6.45 (d, 1H), 7.28 (d, 1H), 7.44 (d, 1H), 7.57 (d, 1H), 7.96 (s, 1H)

<Step 2> Synthesis of 6- (2-nitrophenyl) benzo [b] selenophene

2- (benzo [b] selenophen-6-yl) -4,4,5,5- instead of 2- (benzofuran-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane A 6- (2-nitrophenyl) benzo [b] selenophene was obtained by following the same procedure as in <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, 1H), 8.02 (d, 1H), 8.08 (t, 1H)

Step 3 Synthesis of IC-43

Except for using 6- (2-nitrophenyl) benzo [b] selenophene instead of 5- (2-nitrophenyl) benzofuran IC-43 was obtained by the same procedure as in <Step 3> of Preparation Example 36.

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, 1H), 8.09 (t, 1H), 10.55 (s, 1H)

Synthesis Example 1 Synthesis of Inv-1

IC-1 (3 g, 10.63 mmol), 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 under a nitrogen stream. 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, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent in the organic layer was removed from water and purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to give the title compound Inv-1 (2.26 g, yield 49%).

GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

Synthesis Example 2 Synthesis of Inv-2

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

GC-Mass (Theoretical value: 435.17 g / mol, Measured value: 435.17 g / mol)

Synthesis Example 3 Synthesis of Inv-3

IC-1 (3 g, 10.63 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.38 g, 12.75 mmol), Pd (OAc) ₂ (0.12) under nitrogen stream g, 5 mol%), NaO (t-bu) (2.04 g, 21.25 mmol), P (t-bu) ₃ (0.21 g, 1.06 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C. for 12 hours. Stirred.

After completion of the reaction, the mixture was extracted with ethyl acetate and then dried with MgSO ₄ , and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain Inv-3 (4.89 g, yield 78). %) Was obtained.

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 4 Synthesis of Inv-4

2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) -1,3,5-triazine instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 3 to obtain the title compound Inv-4 (4.97 g, 79%).

GC-Mass (Theoretical value: 591.22 g / mol, Measured value: 591 g / mol)

Synthesis Example 5 Synthesis of Inv-5

Inv, a target compound, was prepared in the same manner as in Synthesis Example 1, except that 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 3-bromobiphenyl. -5 (3.21 g, 50%) was obtained.

GC-Mass (Theoretical value: 603.24 g / mol, Measured value: 603 g / mol)

Synthesis Example 6 Synthesis of Inv-6

Inv, a target compound, was prepared in the same manner as in Synthesis Example 1, except that 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 3-bromobiphenyl. -6 (3.47 g, 49%) was obtained.

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 7 Synthesis of Inv-7

2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -1,3,5-triazine instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using the same process as in Synthesis Example 3 to obtain the title compound Inv-7 (5.38 g, 76%).

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 8 Synthesis of Inv-8

The same procedure as in 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. The resulting compound, Inv-8 (4.63 g, 74%) was obtained.

GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 9 Synthesis of Inv-9

Except for using 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) pyrimidine instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Inv-9 (4.83 g, 77%) was obtained by the same procedure as in Synthesis Example 3.

GC-Mass (Theoretical value: 590.22 g / mol, Measured value: 590 g / mol)

Synthesis Example 10 Synthesis of Inv-10

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

GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

Synthesis Example 11 Synthesis of Inv-11

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

GC-Mass (Theoretical value: 678.25 g / mol, Measured value: 678 g / mol)

Synthesis Example 12 Synthesis of Inv-12

Except for using (4-bromophenyl) diphenylborane instead of 3-bromobiphenyl was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Inv-12 (2.44 g, 44%).

GC-Mass (Theoretical value: 522.23 g / mol, Measured value: 522 g / mol)

Synthesis Example 13 Synthesis of Inv-13

Except for using (4-bromophenyl) diphenylphosphine instead of 3-bromobiphenyl was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Inv-13 (2.59 g, 45%).

GC-Mass (Theoretical value: 542.19 g / mol, Measured value: 542 g / mol)

Synthesis Example 14 Synthesis of Inv-14

Inv-, the target compound, was prepared in the same manner as in Synthesis Example 3, except that (4-chlorophenyl) triphenylsilane was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. 14 (4.92 g, 75%) was obtained.

GC-Mass (Theoretical value: 616.23 g / mol, Measured value: 616 g / mol)

Synthesis Example 15 Synthesis of Inv-15

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

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 16 Synthesis of Inv-16

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

GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

Synthesis Example 17 Synthesis of Inv-17

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

GC-Mass (Theoretical value: 435.17 g / mol, Measured value: 435 g / mol)

Synthesis Example 18 Synthesis of Inv-18

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

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 19 Synthesis of Inv-19

IC-3 and 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using -1,3,5-triazine was carried out in the same manner as in Synthesis Example 3 to obtain the title compound Inv-19 (4.53 g, 72%).

GC-Mass (Theoretical value: 591.22 g / mol, Measured value: 591 g / mol)

Synthesis Example 20 Synthesis of Inv-20

The same as in Synthesis Example 1 except for using IC-3 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 3-bromobiphenyl The procedure was followed to obtain Inv-20 (2.95 g, 46%) as the target compound.

GC-Mass (Theoretical value: 603.24 g / mol, Measured value: 603 g / mol)

Synthesis Example 21 Synthesis of Inv-21

The same as in Synthesis Example 1 except for using IC-3 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 3-bromobiphenyl The procedure was followed to obtain the target compound Inv-21 (3.18 g, 45%).

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 22 Synthesis of Inv-22

IC-3 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Exc-22 (6.07 g, 77%) was obtained by the same procedure as in Synthesis Example 3, except that -1,3,5-triazine was used.

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 23 Synthesis of Inv-23

Except for 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 Inv-23 (4.69 g, 75%) was obtained by the same procedure as in Synthesis Example 3.

GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 24 Synthesis of Inv-24

IC-3 and 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using pyrimidine was carried out the same procedure as in Synthesis Example 3 to obtain the target compound Inv-24 (4.46 g, 71%).

GC-Mass (Theoretical value: 590.22 g / mol, Measured value: 590 g / mol)

Synthesis Example 25 Synthesis of Inv-25

Inv, a target compound, was prepared in the same manner as in Synthesis Example 1, 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%) was obtained.

GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

Synthesis Example 26 Synthesis of Inv-26

The above synthesis 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 Inv-26 (2.96 g, 41%) was obtained by the same procedure as in Example 1.

GC-Mass (Theoretical value: 678.25 g / mol, Measured value: 678 g / mol)

Synthesis Example 27 Synthesis of Inv-27

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

GC-Mass (Theoretical value: 522.23 g / mol, Measured value: 522 g / mol)

Synthesis Example 28 Synthesis of Inv-28

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

GC-Mass (Theoretical value: 542.19 g / mol, Measured value: 542 g / mol)

Synthesis Example 29 Synthesis of Inv-29

The same procedure as in Synthesis Example 3 except for using IC-3 and (4-chlorophenyl) triphenylsilane instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine To give the target compound Inv-29 (4.65 g, 71%).

GC-Mass (Theoretical value: 616.23 g / mol, Measured value: 616 g / mol)

Synthesis Example 30 Synthesis of Inv-30

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

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 31 Synthesis of Inv-31

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

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 32 Synthesis of Inv-32

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

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 33 Synthesis of Inv-33

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

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

Using the 3,7-diphenyl-3,10-dihydropyrrolo [3,2-a] carbazole in place of IC-1, the same procedure as in Synthesis Example 3 was carried out, thereby Inv-33 (6.27 g, 68%) was the target compound. Got.

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 34 Synthesis of Inv-34

Except for using 9-phenyl-9H-carbazol-3-ylboronic acid instead of phenylboronic acid was carried out in the same manner as in Synthesis Example 33 to obtain the target compound Inv-34 (7.94 g, 69%).

GC-Mass (Theoretical value: 830.32 g / mol, Measured value: 830 g / mol)

Synthesis Example 35 Synthesis of Inv-35

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 36 Synthesis of Inv-36

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

GC-Mass (Theoretical value: 983.37 g / mol, Measured value: 983 g / mol)

Synthesis Example 37 Synthesis of Inv-37

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

GC-Mass (Theoretical value: 603.24 g / mol, Measured value: 603 g / mol)

Synthesis Example 38 Synthesis of Inv-38

The same as in Synthesis Example 1 except that IC-9 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine are used instead of IC-1 and 3-bromobiphenyl. The procedure was followed to obtain Inv-38 (3.58 g, 52%) as the target compound.

GC-Mass (Theoretical value: 679.27 g / mol, Measured value: 679 g / mol)

Synthesis Example 39 Synthesis of Inv-39

IC-9 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using -1,3,5-triazine was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Inv-39 (5.20 g, 68%).

GC-Mass (Theoretical value: 775.30 g / mol, Measured value: 775 g / mol)

Synthesis Example 40 Synthesis of Inv-40

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 41 Synthesis of Inv-41

Except for using IC-10 and 2- (4-bromophenyl) -4,6-diphenylpyrimidine instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Inv-41 (2.67 g, 48%) was obtained by the same procedure as in Synthesis Example 1.

GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

Synthesis Example 42 Synthesis of Inv-42

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

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 43 Synthesis of Inv-43

The same as in Synthesis Example 1 except for using IC-11 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 3-bromobiphenyl The procedure was followed to obtain the target compound Inv-43 (2.94 g, 52%).

GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

Synthesis Example 44 Synthesis of Inv-44

Inv, a target compound, was prepared in the same manner as in Synthesis Example 1, 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%) was obtained.

GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

Synthesis Example 45 Synthesis of Inv-45

The above synthesis except for using IC-11 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole instead of IC-1 and 3-bromobiphenyl Inv-45 (2.81 g, 49%) was obtained by the same procedure as in Example 1.

GC-Mass (Theoretical value: 830.32 g / mol, Measured value: 830 g / mol)

Synthesis Example 46 Synthesis of Inv-46

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

GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

Synthesis Example 47 Synthesis of Inv-47

IC-12 and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5- instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using triazine was carried out the same procedure as in Synthesis Example 3 to obtain the target compound Inv-47 (3.66 g, 65%).

GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

Synthesis Example 48 Synthesis of Inv-48

Inv-48 (2.64) was prepared by the same procedure as in Synthesis Example 1, except that IC-12 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl. g, 47%).

GC-Mass (Theoretical value: 656.22 g / mol, Measured value: 656 g / mol)

Synthesis Example 49 Synthesis of Inv-49

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 50 Synthesis of Inv-50

IC-13 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using -1,3,5-triazine, the same procedure as in Synthesis Example 3 was performed to obtain Inv-50 (5.00 g, 73%) as a target compound.

GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

Synthesis Example 51 Synthesis of Inv-51

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 52 Synthesis of Inv-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%) was obtained as the target compound.

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 53 Synthesis of Inv-53

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 54 Synthesis of Inv-54

Exc-54 (2.66 g, 54%).

GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 55 Synthesis of Inv-55

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

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 56 Synthesis of Inv-56

Inv-56 (1.99 g, 49%) was prepared by the same procedure as in Synthesis Example 1, except that IC-16 and 2- (4-bromophenyl) pyrimidine were used instead of IC-1 and 3-bromobiphenyl Got.

GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 57 Synthesis of Inv-57

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

GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

Synthesis Example 58 Synthesis of Inv-58

The same as in Synthesis Example 1 except for using IC-17 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 3-bromobiphenyl The procedure was followed to obtain the target compound Inv-58 (2.89 g, 46%).

GC-Mass (Theoretical value: 733.25 g / mol, Measured value: 733 g / mol)

Synthesis Example 59 Synthesis of Inv-59

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

GC-Mass (Theoretical value: 754.28 g / mol, Measured value: 754 g / mol)

Synthesis Example 60 Synthesis of Inv-60

The above synthesis except for using IC-18 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole instead of IC-1 and 3-bromobiphenyl The same procedure as in Example 1 was performed to obtain Inv-60 (2.49 g, 44%) as a target compound.

GC-Mass (Theoretical value: 843.31 g / mol, Measured value: 843 g / mol)

Synthesis Example 61 Synthesis of Inv-61

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

GC-Mass (Theoretical value: 678.25 g / mol, Measured value: 678 g / mol)

Synthesis Example 62 Synthesis of Inv-62

Inv-62 (1.94 g, 47%) was prepared in the same manner as in Synthesis Example 1, except that IC-19 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl )

GC-Mass (Theoretical value: 830.32 g / mol, Measured value: 830 g / mol)

Synthesis Example 63 Synthesis of Inv-63

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 64 Synthesis of Inv-64

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665.26 g / mol)

Synthesis Example 65 Synthesis of Inv-65

IC-21 and 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) instead of IC-1 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using -1,3,5-triazine was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Inv-65 (5.07 g, 74%).

GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

Synthesis Example 66 Synthesis of Inv-66

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 67 Synthesis of Inv-67

Inv-67 (2.84) was prepared by the same procedure as in Synthesis Example 1, except that IC-22 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine were used instead of IC-1 and 3-bromobiphenyl. g, 51%).

GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

Synthesis Example 68 Synthesis of Inv-68

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

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 69 Synthesis of Inv-69

The same as in Synthesis Example 1 except for using IC-23 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 3-bromobiphenyl The procedure was followed to obtain the target compound Inv-69 (2.71 g, 48%).

GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

Synthesis Example 70 Synthesis of Inv-70

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

GC-Mass (Theoretical value: 587.24 g / mol, Measured value: 587 g / mol)

Synthesis Example 71 Synthesis of Inv-71

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

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 72 Synthesis of Inv-72

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

GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 73 Synthesis of Inv-73

Inv-73 (2.25 g, 52%) was prepared in the same manner as in Synthesis Example 1, except that IC-25 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl. )

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 74 Synthesis of Inv-74

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 75 Synthesis of Inv-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 (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 76 Synthesis of Inv-76

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

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 77 Synthesis of Inv-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 (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

Synthesis Example 78 Synthesis of Inv-78

Exc-78 (1.87 g, 48%) was obtained in the same manner as in Synthesis Example 1, except that IC-27 was used instead of IC-1.

GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

Synthesis Example 79 Synthesis of Inv-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 (Theoretical value: 665.26 g / mol, Measured value: 665.26 g / mol)

Synthesis Example 80 Synthesis of Inv-80

Inv-80 (2.12 g, 49%) was prepared in the same manner as in Synthesis Example 1, except that IC-27 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl. )

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 81 Synthesis of Inv-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 (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 82 Synthesis of Inv-82

Inv-82 (1.99 g, 46%) was prepared in the same manner as in Synthesis Example 1, except that IC-28 and 1-bromo-3,5-diphenylbenzene were used instead of IC-1 and 3-bromobiphenyl. )

GC-Mass (Theoretical value: 740.29 g / mol, Measured value: 740 g / mol)

Synthesis Example 83 Synthesis of Inv-83

The same as in Synthesis Example 1 except for using IC-14 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of IC-1 and 3-bromobiphenyl The procedure was followed to obtain the target compound Inv-83 (3.54 g, 57%).

GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

Synthesis Example 84 Synthesis of Inv-84

Inv, a target compound, was prepared in the same manner as in Synthesis Example 1, 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%) was obtained.

GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

Synthesis Example 85 Synthesis of Inv-85

Under nitrogen streams IC-29a (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 the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Inv-85 (3.77 g, yield: 83%) as a target compound.

GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

Synthesis Example 86 Synthesis of Inv-86

IC-29a (2.23 g, 10.0 mmol), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) under nitrogen stream ) And DMF (30 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain the title compound Inv-86 (3.45 g, yield: 65%).

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 87 Synthesis of Inv-87

IC-29a (2.23 g, 10.0 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) under nitrogen stream ) And DMF (30 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain the title compound Inv-87 (3.77 g, yield: 71%).

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 88 Synthesis of Inv-88

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

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 89 Synthesis of Inv-89

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

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 90 Synthesis of Inv-90

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

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 91 Synthesis of Inv-91

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

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 92 Synthesis of Inv-92

Exv-92 (3.50 g, yield: 77%) was obtained in the same manner as Synthesis Example 85 except for using IC-32 (2.23 g, 10.0 mmol) instead of IC-29a.

GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

Synthesis Example 93 Synthesis of Inv-93

Inv-93 (3.26 g, Yield 58%) was obtained by the same procedure as in Synthesis Example 1, except that IC-33 and 1-bromo-4-phenylisoquinoline were used instead of IC-1 and 3-bromobiphenyl. Got it.

GC-Mass (Theoretical value: 436.19 g / mol, Measured value: 436 g / mol)

Synthesis Example 94 Synthesis of Inv-94

Inv-94 (3.11 g, 63% yield) was carried out in the same manner as in Synthesis Example 1, except that IC-34 and 4-bromo-2,6-diphenylpyridine were used instead of IC-1 and 3-bromobiphenyl. )

GC-Mass (Theoretical value: 586.24 g / mol, Measured value: 586 g / mol)

Synthesis Example 95 Synthesis of Inv-95

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

GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

Synthesis Example 96 Synthesis of Inv-96

IC-36 (3 g, 14.48 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (5.97 g, 17.37 mmol), Pd (OAc) ₂ (0.16) under nitrogen stream g, 5 mol%), NaO (t-bu) (2.78 g, 28.95 mmol), P (t-bu) ₃ (0.29 g, 1.45 mmol) and Toluene (100 ml) were mixed and 12 h at 110 ° C. Stirred.

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

GC-Mass (Theoretical value: 514.18 g / mol, Measured value: 514 g / mol)

Synthesis Example 97 Synthesis of Inv-97

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

GC-Mass (Theoretical value: 514.18 g / mol, Measured value: 514 g / mol)

Synthesis Example 98 Synthesis of Inv-98

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

GC-Mass (Theoretical value: 514.18 g / mol, Measured value: 514 g / mol)

Synthesis Example 99 Synthesis of Inv-99

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

GC-Mass (Theoretical value: 556.21 g / mol, Measured value: 556 g / mol)

Synthesis Example 100 Synthesis of Inv-100

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

GC-Mass (Theoretical value: 680.24 g / mol, Measured value: 680 g / mol)

Synthesis Example 101 Synthesis of Inv-101

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

GC-Mass (Theoretical value: 578.10 g / mol, Measured value: 578 g / mol)

Synthesis Example 102 Synthesis of Inv-102

Exc-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 (Theoretical value: 578.10 g / mol, Measured value: 578 g / mol)

Synthesis Example 103 Synthesis of Inv-103

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

GC-Mass (Theoretical value: 578.10 g / mol, Measured value: 578 g / mol)

Synthesis Example 104 Synthesis of Inv-104

IC-1 (10 g, 35.44 mmol), 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) under a nitrogen stream, 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, 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 to which water was removed, and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain Inv-104 (8.6 g, yield 50%).

GC-Mass (Theoretical value: 486.18 g / mol, Measured value: 486 g / mol)

Synthesis Example 105 Synthesis of Inv-105

Inv-105 was obtained by the same procedure as in Synthesis Example 104 except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline instead of 2-chloro-4-phenylquinazoline.

GC-Mass (Theoretical value: 612.23 g / mol, Measured value: 612 g / mol)

Synthesis Example 106 Synthesis of Inv-106

Inv-106 was obtained by the same procedure as in Synthesis Example 104 except for using IC-2 instead of IC-1.

GC-Mass (Theoretical value: 486.18 g / mol, Measured value: 486 g / mol)

Synthesis Example 107 Synthesis of Inv-107

Inv-107 was obtained by the same procedure as Synthesis Example 104 except for using IC-4 instead of IC-1.

GC-Mass (Theoretical value: 486.18 g / mol, Measured value: 486 g / mol)

Synthesis Example 108 Synthesis of Inv-108

Inv-108 was obtained by the same procedure as Synthesis Example 104 except for using IC-3 instead of IC-1.

GC-Mass (Theoretical value: 486.18 g / mol, Measured value: 486 g / mol)

Synthesis Example 109 Synthesis of Compound 1

<Step 1> Synthesis of 2,5-Diphenylpyridine (L1)

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 under nitrogen stream Was added and stirred. 5.78 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removal of the solvent of the filtered organic layer, 19.20 g (yield: 83%) of 2,5-Diphenylpyridine (L1) was obtained using column chromatography.

<Step 2> Synthesis of 2,5-Diphenylpyridinato iridium dimer (D1)

Under a nitrogen stream, 5.0 g (13.8 mmol) of IrCl ₃ xH ₂ O and the L 1 (9.6 g, 41.4 mmol) were added to 120 ml of 2-methoxyethanol and 40 ml of a mixed solvent and refluxed for 20 hours. After cooling the reaction mixture to room temperature, the resulting precipitate was filtered and the product was purified with acetone and ethanol 1: 1 solvent to give D1 (9.31 g, yield 98%).

Step 3 Synthesis of Solvent Coordination Cationic Intermediate (I1)

D1 above (8.0 g, 5.81 mmol) and AgPF₆ (3.67 g, 14.53 mmol) was added to a mixed solvent of 300 ml of methylene chloride and 100 ml of methanol and stirred at room temperature for 6 hours under a stream of nitrogen. The reaction mixture was passed through celite to remove AgCl, the filtrate was distilled under reduced pressure to remove about 90% of solvent, and then ethyl ether and hexane were added thereto to separate target 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 added to 300 ml of ethanol and refluxed under nitrogen atmosphere for 20 hours. After completion of the reaction, the precipitate obtained by filtration was purified by column chromatography to obtain compound 1 (8.12 g, yield 92%) as a target compound.

GC-Mass (Theoretical value: 883.07 g / mol, Measured value: 883 g / mol)

Synthesis Example 110 Synthesis of Compound 9

<Step 1> Synthesis of 2-phenylpyridine (L2)

L2 (13.2 g, yield 85%) was obtained by the same method as <Step 1> of Synthesis Example 109, except that 2-bromopyridine was used instead of 2,5-dibromopyridine.

<Step 2> Synthesis of 2-phenylpyridinato iridium dimer (D2)

D2 (7.59 g, Yield 92%) was obtained in the same manner as in <Step 2> of Synthesis Example 109 except for using L2 instead of L1.

Step 3 Synthesis of Solvent Coordination Cationic Intermediate (I2)

Intermediate compound I2 (6.28 g, Yield 85%) was obtained by the same method as <Step 3> of Synthesis Example 109, except that D2 was used instead of D1.

Step 4 Synthesis of Compound 9

Compound 9 (6.07 g, 83% yield) was obtained by the same method as <Step 4> of Synthesis Example 109, except that I2 was used instead of I1.

GC-Mass (Theoretical value: 730.88 g / mol, Measured value: 731 g / mol)

Synthesis Example 111 Preparation of Compound 149

<Step 1> Synthesis of 2-biphenyl-3-yl-pyridine (L3)

L3 (20.59 g, yield 89%) was obtained by the same method as <step 1> of Synthesis Example 110, except that 3-biphenylboronic acid was used instead of phenylboronic acid.

Step 2 Synthesis of Compound 149

5.0 g (10.0 mmol) Ir (acac) under nitrogen stream₃And L3 (6.94 g, 30.0 mmol) were added to 30 ml of glycerol and refluxed for 24 hours. After the reaction was completed, the precipitate obtained by filtration was purified by column chromatography to obtain compound 149 as a target compound. (2.47 g, yield 28%) was obtained.

GC-Mass (Theoretical value: 883.07 g / mol, Measured value: 883 g / mol)

Synthesis Example 112 Synthesis of Compound 164

Step 1 Synthesis of 2-phenylquinoline (L4)

Add 20.8 g (0.1 mol) of 2-bromoquinoline, 14.63 g (0.12 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 under a nitrogen stream. Stirred. 5.78 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removal of the solvent of the filtered organic layer, 16.40 g (yield: 80%) of 2-phenylquinoline (L4) was obtained using column chromatography.

<Step 2> Synthesis of 2-phenylquinolinato iridium dimer (D4)

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

Step 3 Synthesis of Compound 164

D4 above (5.01 g, 5.81 mmol) and 2,4-pentanedione (1.74 g, 17.4 mmol), anhydrous Na₂CO₃(4.82 g, 34.86 mol) was refluxed in 120 ml of 2-ethoxyethanol. After cooling the reaction mixture to room temperature, the resulting precipitate was filtered, separated by column chromatography, and recrystallized to obtain the desired compound 164 (2.64 g, yield 92%).

GC-Mass (Theoretical value: 496.09 g / mol, Measured value: 496 g / mol)

[Examples 1 to 103]

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

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

M-MTDATA (60 nm) / TCTA (80 nm) / Inv-1 to Inv-103 compound (90%) + compound 1 (10%) of Synthesis Example 109 (300 nm) on the thus prepared ITO transparent substrate (electrode) ) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare an organic EL device.

[Examples 104 to 114]

Compound Inv-3, Inv-5, Inv-6, Inv-7, Inv-8, Inv-18, Inv-21, Inv-23, Inv-30, Inv-31, Inv- 87, a green organic electroluminescent device was manufactured in the same manner as in Example 1 except that Compound 9 of Synthesis Example 110 was used as a light emitting dopant material.

[Examples 115 to 125]

Compound Inv-3, Inv-5, Inv-6, Inv-7, Inv-8, Inv-18, Inv-21, Inv-23, Inv-30, Inv-31, Inv- 87, a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that compound 149 of Synthesis Example 111 was used as the light emitting dopant material.

[Examples 126 to 131]

Except for using compound Inv-18, Inv-104, Inv-105, Inv-106, Inv-107, Inv-108 as a light emitting host material and compound 164 of Synthesis Example 112 as a light emitting dopant material. In the same manner as in Example 1, a green organic EL device was manufactured.

Comparative Example 1

A green organic electroluminescent device in the same manner as in Example 1, except that CBP instead of Compound Inv-1 and Ir (ppy) ₃ instead of Compound 1 of Synthesis Example 109 are used as a light emitting dopant material when forming the emission layer. Was prepared.

Comparative Example 2

Green organic light-emitting process was carried out in the same manner as in Example 126, except that CBP was used instead of Compound Inv-18 as a light emitting host material and Ir (piq) ₂ (acac) was used instead of Compound 164 of Synthesis Example 112 as a light emitting dopant material. An electroluminescent device was manufactured.

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

[Evaluation Example 1]

For each organic electroluminescent device of Examples 1 to 125 and Comparative Example 1, the driving voltage, the light emission peak, and the current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

Table 1

Sample	Host	Dopant	Drive 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	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

Referring to Table 1, the organic compound of the present invention is applied to the compound (Inv-1 to Inv-103) according to the invention as a host of the light emitting layer, and the compound (compounds 1, 9 and 149) according to the present invention as a dopant of the light emitting layer The electroluminescent device exhibits better performance in terms of efficiency and driving voltage than the conventional organic electroluminescent device (Comparative Example 1) and has various emission wavelengths depending on the dopant.

[Evaluation Example 2]

For each organic electroluminescent device of Examples 126 to 131 and Comparative Example 2, the driving voltage, the light emission peak, and the current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

TABLE 2

Sample	Host	Dopant	Drive 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

Referring to Table 2, the organic compound of the present invention is applied to the compound (Inv-18, Inv-104 to Inv-108) according to the invention as a host of the light emitting layer, the compound (compound 164) according to the present invention as a dopant of the light emitting layer It can be seen that the electroluminescent device exhibits better performance in terms of efficiency and driving voltage than the conventional organic electroluminescent device (Comparative Example 2).

The organic electroluminescent device of the present invention efficiently transfers energy between a host and a dopant by using the indole compound represented by Chemical Formula 1 as a phosphorescent host of the light emitting layer and the iridium compound represented by Chemical Formula 3 as a phosphorescent dopant of the light emitting layer. This makes it excellent in characteristics such as light emission performance, driving voltage and lifespan.

Claims (8)

1. anode; cathode; And one or more organic material layers interposed between the anode and the cathode,

   At least one of the at least one organic material layer is an organic electroluminescent device comprising a compound represented by the following formula (1) and a compound represented by the following formula (3):

   [Formula 1]

   

   In Chemical Formula 1,

   Y ₁ to Y ₄ are each independently N or CR ₃ ,

   _One of Y ₁ and Y ₂ , Y ₂ and Y ₃ , or Y ₃ and Y ₄ forms a condensed ring represented by the following Chemical Formula 2,

   [Formula 2]

   

   In Chemical Formula 2,

   The dashed line means a site where condensation occurs with the compound of Formula 1,

   Y ₅ to Y ₈ are each independently 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 ), wherein At least one of X ₁ and X ₂ is N (Ar ₁ ),

   R ₁ to R ₄ and Ar ₁ to Ar ₅ are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C Alkynyl group of ₂ to C ₄₀ , cycloalkyl group of C ₃ to C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ 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 ~ arylboronic group of C _60, C ₆ ~ C ₆₀ aryl phosphine group, and selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of,

   R ₁ to R ₄ may be bonded to an adjacent group 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, arylsilyl group of R ₁ to R ₄ and Ar ₁ to Ar ₅ , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 Heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, 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 May be substituted with one or more selected

   [Formula 3]

   

   In Chemical Formula 3,

   XY is an organic ligand, X is a hetero-aryl group of from 3 to 40 nuclear atoms, Y is a C ₆ ~ C ₄₀ heteroaryl group of the aryl group or nuclear atoms of 3 to 40,

   R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, and nuclear atom 3 to 40 heterocyclo Alkyl group, C ₆ -C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, 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 It is selected from the group consisting of a pin oxide group and an arylamine group of C ₆ ~ C ₆₀ , can be combined with adjacent groups to form a condensed ring,

   n is an integer of 1-3.
2. The method of claim 1,

   The compound represented by Chemical Formula 1 is selected from the group consisting of compounds represented by the following Chemical Formulas 1a to 1f:

   [Formula 1a]

   

   [Formula 1b]

   

   [Formula 1c]

   [Formula 1d]

   

   [Formula 1e]

   

   [Formula 1f]

   

   In Formulas 1a to 1f, X ₁ , X ₂ and R ₁ to R ₄ are the same as defined in claim 1.
3. The method of claim 1,

   The compound represented by the formula (3) is an organic electroluminescent device, characterized in that selected from the group consisting of compounds represented by the formula (3a to 3d):

   [Formula 3a]

   

   [Formula 3b]

   

   [Formula 3c]

   

   [Formula 3d]

   

   In Chemical Formulas 3a to 3d, X, Y, n, and R ₁₁ to R ₁₈ are the same as defined in claim 1,

   Ra and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 Heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ Is selected from the group consisting of an aryl phosphine oxide group and an arylamine group of C ₆ ~ C ₆₀ , may be combined with adjacent groups to form a condensed ring,

   M is an integer of 0-3.
4. The method of claim 1,

   X ₁ and X ₂ of Formula 1 are each independently S or N (Ar ₁ ), characterized in that the organic electroluminescent device.
5. The method of claim 1,

   Ar ₁ to Ar ₅ of Formula 1 is characterized in that each independently selected from the group consisting of C ₆ ~ C ₆₀ aryl group, a nuclear atoms aryl of from 5 to 60 heteroaryl group, and a C ₆ ~ with an aryl amine of the C ₆₀ Organic electroluminescent device.
6. The method of claim 1,

   X-Y of Formula 3 is an organic electroluminescent device, characterized in that selected from the group consisting of the structures represented by A1 to A24:

   

   R ₃₁ to R ₄₂ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, or a hetero atom having 3 to 40 nuclear atoms. Cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₅ ~ C ₆₀ heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyl Silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl It is selected from the group consisting of a phosphine oxide group and an arylamine group of C ₆ ~ C ₆₀ , may be combined with adjacent groups to form a condensed ring.
7. The method of claim 1,

   The organic material layer including the compound represented by Formula 1 and the compound represented by Formula 3 is selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer.
8. The method of claim 1,

   The organic material layer including the compound represented by Formula 1 and the compound represented by Formula 3 is a light emitting layer,

   The compound represented by Chemical Formula 1 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.