KR20130007951A - Organic electroluminescence device using the triphenylene derivative - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic light emitting compound and an organic electroluminescent device including the same. More specifically, the present invention relates to a novel organic light emitting compound used as a hole or electron injection and transportation, .

Description

TECHNICAL FIELD [0001] The present invention relates to a triphenylene compound and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a triphenylene-based organic electroluminescent device having a specific structure and an organic electroluminescent device having improved characteristics such as luminous efficiency, luminance, thermal stability, driving voltage and lifetime by incorporating the above material into one or more organic layers .

The study of organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to the blue electroluminescence using anthracene single crystals in 1965, based on Bernanose's observation of organic thin film emission. By (Tang), an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The phosphorescent dopant as well as phosphorescent host materials have been studied extensively.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials are metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , And CBP is a phosphorescent host material. However, existing materials have advantages in terms of light emitting properties, but they are not satisfactory in terms of lifetime in OLED devices because of low glass transition temperature and poor thermal stability. Therefore, development of materials with higher performance is required.

Republic of Korea Patent Publication 2010-0108924

SUMMARY OF THE INVENTION The present invention has been conceived to solve the above-mentioned problems, and an object thereof is to provide a novel organic compound having an improved glass transition temperature and excellent thermal stability.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound and having improved various characteristics such as luminous efficiency, luminance, power efficiency, thermal stability, driving voltage, and device lifetime.

The present invention provides a compound represented by the following formula (1) or (2), preferably a triphenylene-based organic electroluminescent device material.

In the above formulas,

X and Y are NR ₁₅ or a directly linked single bond, where one of X and Y is NR ₁₅ (one of m and n is 1), and the other is a single bond (one of m and n is 0) ,

R ₁ to R ₁₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group each other, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkylamino group, C ₅ to C ₄₀ arylamino group, C ₅ to C ₄₀ diarylamino group, C ₅ to C ₄₀ heteroarylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ aryl An alkyl group, a C ₆ to C ₄₀ heteroarylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₁ to C ₄₀ halogenalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₃ to C ₄₀ alkylsilyl group, C ₃ ~ C ₄₀ aryl silyl group, and a C ₃ ~ is selected from the heteroaryl group consisting of a silyl group of C _40,

Wherein R ₁ to R ₁₅ may each be fused to an adjacent substituent or form a ring;

m and n are 0 or 1, respectively.

In addition, the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, a compound represented by the formula (1) And it provides an organic electroluminescent device comprising at least one compound selected from the group consisting of a compound represented by the formula (2).

Herein, the organic material layer including the compound represented by Chemical Formula 1 and / or Chemical Formula 2 may be at least one selected from the group consisting of a light emitting layer, a hole injection layer, and a hole transport layer, and particularly, a phosphorescent or fluorescent host material of the light emitting layer. desirable.

The compound represented by the general formula (1) of the present invention is excellent in luminance, power efficiency, heat resistance, hole or electron transporting and injection performance, and can exhibit increased color purity and luminous efficiency as a light emitting layer. Layer, a transport layer, and a phosphorescent and fluorescent host or dopant of the light emitting layer.

Therefore, when using the novel compounds of the present invention, it is possible to produce a very good organic electroluminescent device (OLED) exhibiting low driving voltage, high current efficiency and long life.

1 is a schematic cross-sectional view of an organic EL device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

In the present invention, a material for a conventional organic light emitting device [for example, N4, N4'-di (naphthalene-1-yl) -N4, N4'- diphenylbiphenyl-4,4'- dicarbazolybiphenyl (hereinafter abbreviated as CBP)], and has a wide energy bandgap and a triphenylene-based compound having a specific structure.

The compound represented by Chemical Formula 1 or Chemical Formula 2 is a fused heterocyclic moiety connected to a triphenylene-based basic skeleton, thereby stably forming triplet energy levels through orbital mixing. At the same time, the energy level is controlled by a variety of substituents to have a wide bandgap (sky blue to red). As a result, the phosphorescence characteristics of the device can be improved and the electron and / or hole transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like can be improved. Therefore, it can be applied not only as a light emitting layer but also as a hole transporting layer, an electron transporting layer and a host by introducing various substituents. In particular, due to the wide band gap derived from the triphenylene-based skeleton, it can exhibit excellent properties as a host material, and due to the introduction of substituents such as tertiary amines, it can exhibit excellent properties as a hole transport layer (HTL) material. have.

In addition, the molecular weight of the compound is significantly increased due to various aromatic ring substituents introduced into the triphenylene-based skeleton, whereby the glass transition temperature is improved and thus the polymer has higher thermal stability than the conventional NPB or CBP have. Therefore, the device including the triphenylene compound of the present invention can exhibit improvement in durability and lifetime.

In addition, when the compound is used as a hole transporting layer and a blue, green and / or red phosphorescent host material or a fluorescent host material of an organic light emitting device, it is possible to exert an excellent effect in terms of efficiency and life as compared to NPB and CBP. Therefore, the compound represented by Formula 1 or Formula 2 according to the present invention can greatly contribute to improving the performance and lifespan of the organic light emitting device, and in particular, the device life improvement has a great effect on maximizing the performance in the full color organic light emitting panel. .

Compounds represented by the formula (1) of the present invention, can be more specifically expressed by any one of the following formula (3) to formula (5). In addition, the compounds represented by the formula (2) of the present invention may be represented in more detail by any one of the following formulas (6) to (8).

In Chemical Formulas 3 to 8,

L is a direct link; C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ Alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkylamino group, C ₅ ~ C ₄₀ arylamino group, C ₅ ~ C ₄₀ diarylamino group, C ₅ ~ C ₄₀ heteroaryl An amino group, a C ₂ -C ₄₀ diheteroarylamino group, a C ₆ -C ₄₀ arylalkyl group, a C ₆ -C ₄₀ heteroarylalkyl group, a C ₃ -C ₄₀ cycloalkyl group, a C ₁ -C ₄₀ halogenalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₃ to C ₄₀ alkylsilyl group, C ₃ to C ₄₀ arylsilyl group, and C ₃ to C ₄₀ heteroarylsilyl group, they are selected from the group Can form a ring,

R ₁₆ and R ₁₇ are the same or different and are each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ of the aryl group , C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkylamino group, C ₅ ~ C ₄₀ arylamino group, C ₅ - a heteroaryl group of C ₄₀ of the diarylamino group, C ₅ ~ C ₄₀ heteroaryl group, C ₂ ~ C ₄₀ of the de-heteroaryl group, C ₆ ~ C ₄₀ aryl group, C ₆ ~ C ₄₀ of, C ₃ C ₄₀ -cycloalkyl group, C ₁ -C ₄₀ halogenalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, C ₃ -C ₄₀ alkylsilyl group, C ₃ -C ₄₀ arylsilyl group, and C ₃ ~ Selected from the group consisting of C ₄₀ heteroarylsilyl groups, which may form a ring with an adjacent group,

Ar _1, R ₁₈ to R ₂₁ are the same or different and are each independently hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ Alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkylamino group, C ₅ ~ C ₄₀ arylamino group, C ₅ ~ C ₄₀ diarylamino group, C ₅ ~ C ₄₀ heteroarylamino group, C ₂ ~ C ₄₀ diheteroarylamino group, C ₆ ~ C ₄₀ arylalkyl group, C ₆ to C ₄₀ heteroarylalkyl group, C ₃ to C ₄₀ cycloalkyl group, C ₁ to C ₄₀ halogenalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₃ to C ₄₀ alkyl a silyl group, a C ₃ ~ C ₄₀ aryl silyl group, and C ₃ ~ is selected from heteroaryl, silyl group the group consisting of C ₄₀ of, and except for Ar ₁ is not hydrogen, they may form a contiguous group ring,

R ₁ to R ₁₅ are the same as defined in Formula 1 or Formula 2.

In the triphenylene-based compound according to the present invention, the compound of formula (I) containing N as X may be more specified by the formulas illustrated below. However, the compounds represented by formula (1) of the present invention are not limited to those illustrated below.

In addition, in the triphenylene-based compound according to the present invention, the compound of formula (2) containing N as X may be more specified by the formulas illustrated below. However, the compound represented by the formula (2) of the present invention is not limited to those illustrated below.

The compound represented by Formula 1 or Formula 2 of the present invention may be synthesized according to a general synthesis method. (Chem Rev, 60:.. .. 313 (1960); J. Chem SOC 4482 (1955); Chem Rev 95:.. Reference 2457 (1995)) Detailed synthesis procedures for the compounds of the invention are synthesized which will be described later for example, This will be described in detail.

Another aspect of the present invention relates to an organic electroluminescent device comprising the compound represented by Chemical Formula 1 or Chemical Formula 2, preferably Chemical Formulas 3 to 8.

Specifically, the present invention provides a fuel cell comprising: an anode; A cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer is represented by Chemical Formula 1 or Chemical Formula 2, preferably Chemical Formulas 3 to 8. It is characterized by including a compound represented by. At this time, the compound of Formula 1 to Formula 8 may be included alone or in plurality.

The organic layer including the compound represented by Chemical Formula 1 or Chemical Formula 2, preferably Chemical Formulas 3 to 8 may be any one or more of a hole injection layer, a hole transport layer, and a light emitting layer. And may be included in the organic EL device as the hole injection layer and the hole transport layer material. In this case, the organic EL device can maximize the hole injection / transport capability. And can be used as a light emitting layer material of an organic EL device, thereby providing an improved efficiency and a service life.

In the present invention, the light emitting layer may include a phosphorescent guest material or a fluorescent guest material. Preferably, the compound represented by Formula 1 to Formula 8 may be included in the organic light emitting device as a blue, green and / or red phosphorescent host, a fluorescent host, a hole transport material and / or a hole transport material.

In particular, in the triphenylene-based compound according to the present invention, a host material including a compound of Formula 1 or Formula 2 wherein X is N is preferable, and may be a compound represented by any one of Formulas 3 to 8. Also preferred are hole transport layer (HTL) materials comprising compounds in which substituents such as tertiary amines have been introduced, for example compounds of formulas 4-7. In addition, among the compounds exemplified above, for example, compounds of the Inv1 and Inv5 groups may be used as phosphorescent host materials, and compounds of the Inv2 and Inv6 groups may be used as host materials having side substituents. Inv3 to Inv4 and Inv7 to Inv8 compounds may be used as the hole transport layer material. However, the present invention is not limited thereto.

In addition, the compound represented by Formula 1 or Formula 2, preferably Formula 3 to Formula 8 according to the present invention has a high glass transition temperature of 150 ℃ or more. Therefore, when the compound is used as the organic material layer of the organic light emitting device, the crystallization in the organic light emitting device is minimized, so that the driving voltage of the device can be lowered and the light emitting efficiency, thermal stability and lifetime characteristics can be improved.

Non-limiting examples of the structure of the organic EL device according to the present invention may include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode sequentially laminated. In this case, at least one of the emission layer, the hole injection layer, and the hole transport layer may include a compound represented by Formula 1 or Formula 2. An electron injection layer may be positioned on the electron transport layer.

In addition, as described above, the organic light emitting device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic layer.

In the organic light emitting device of the present invention, the organic layer including the compound of Formula 1 to Formula 8 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.

The organic electroluminescent device according to the present invention is an organic material layer and an electrode using conventional materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1 above. It can be prepared by forming.

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

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of oxides with metals 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, but are not limited thereto.

Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, and the electron injecting layer are not particularly limited, and conventional materials known in the art can be used.

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

[ Synthesis Example 1  : 10- (6- 페닐 피딘 -2- yl ) -10H- phenanthro [9,10-b] carbazole Synthesis of

18.57 g (91.87 mmol) of 1-bromo-2-nitorobenzene, 30 g (110.24 mmol) of Triphenylen-2-boronic acid, 3.18 g (2.75 mmol) of Pd (PPh ₃ ) ₄ and 11.04 g (275.62 mmol) of NaOH After suspended in 300 ml of THF and 150 ml of distilled water and stirred under reflux for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane and dried over MgSO ₄ . After silica gel filtering and column with Hexane: Mc = 4: 1 (v / v) to obtain 31.22g (yield 91.3%) of the target compound 2- (2-Nitrophenyl) triphenylene.

¹ H NMR: 7.36 (t, 1H), 7.52 (t, 1H), 7.71 (m, 4H), 7.83 (t, 1H), 8.20 (d, 2H), 8.35 (d, 1H), 8.59 (d, 1H), 8.68 (d, 1H), 8.77 (t, 2H), 8.99 (d, 1H).

[ Synthesis Example 2 ]

[ Synthesis Example 2 -1: 10H- phenanthro [Synthesis of 9,10-b] carbazole]

[ Synthesis Example 2 -1: 15H- phenanthro [Synthesis of 9,10-a] carbazole]

Under nitrogen, 30 g (85.86 mmol) of 2- (2-Nitrophenyl) triphenylene, 45 g (171.73 mmol) of triphenylphosphine, and 80 ml of 1,2-dichlorobenzene were added thereto, and the mixture was stirred under reflux for 12 hours. After completion of the reaction, the solvent was removed, extracted with dichloromethane and the organic layer was dried over MgSO ₄ . Silica gel filtered and then columned with Hexane: Mc = 2: 1 (v / v) to obtain 10.08 g (yield 37%) of 10H-phenanthro [9,10-b] carbazole as a target compound and 15H-phenanthro [9,10-a ] 13 g of carbazole (48% yield) were obtained, respectively.

Synthesis Example 2-1 (10H-phenanthro [9,10-b] carbazole): ¹ H NMR: (THF) 7.20 (t, 1H), 7.41 (t, 1H), 7.50 (d, 1H), 7.59 (t , 4H), 8.31 (d, 1H), 8.65 (s, 1H), 8.69 (m, 2H), 8.75 (d, 1H), 8.90 (d, 1H), 9.47 (s, 1H), 10.42 (s, 1H). GC-Mass (Theoretical value: 317.12 g / mol, Measured value: 317 g / mol)

Synthesis Example 2-2 (15H-phenanthro [9,10-a] carbazole): ¹ H NMR: (THF) 7.23 (t, 1H), 7.40 (t, 1H), 7.64 (m, 4H), 7.75 (t , 1H), 8.17 (d, 1H), 8.37 (d, 1H), 8.60 (d, 1H), 8.75 (d, 1H), 8.81 (t, 2H), 9.17 (d, 1H), 11.99 (s, 1H). GC-Mass (Theoretical value: 317.12g / mol, Measured value: 317g / mol)

[ Synthesis Example 3  : Compound Inv1 Synthesis of -1 Example 1

7.57g (23.85mmol) of 10H-phenanthro [9,10-b] carbazole and 6.7g (28.62mmol) of 2-bromo-6-phenyl pyridine, Pd ₂ (dba) ₃ 0.655g (0.71mmol), P ( _{t-bu) 3 1.15ml (2.38mmol} ), put NaO (t-bu) 5.73g ( 59.62mmol) and stirred under reflux after addition of 100 ml Toluene 24 hours. After completion of the reaction, the mixture was extracted with dichloromethane and dried over MgSO ₄ . After silica gel filtering, the product was purified by columning with Hexane: Mc 4: 1 (v / v) to obtain 4.2 g (yield 37%) of the title compound, Inv1.

GC-Mass (Theoretical value: 417.18 g / mol, Measured value: 417 g / mol), Elemental Analysis: C, 89.33; H, 4.71; N, 5.95

Synthesis Example 4: Compound Inv1 - Synthesis of 21 - Example 2

1.89 g (78.76 mmol) of NaH under nitrogen was added to 100 ml DMF and stirred. 10 g (31.5 mmol) of 10H-phenanthro [9,10-b] carbazole dissolved in 150 ml of DMF was slowly added thereto, followed by stirring for about 1 hour. Subsequently, 16.9 g (63 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine dissolved in 250 ml of DMF was added slowly and stirred for 12 hours. After completion of the reaction, the mixture was filtered through silica, washed with water and methanol, and the solvent was removed to obtain 8.32 g (yield 48%) of the title compound, Inv1-21.

GC-Mass (Theoretical value: 548.2 g / mol, Measured value: 548 g / mol), Elemental Analysis: C, 85.38; H, 4.41; N, 10.21

[ Synthesis Example 5  : Compound Inv1 - 5 of  synthesis]- Example 3

NaH 0.79 g (32.79 mmol), 10H-phenanthro [9,10-b] carbazole, 4.16 g (13.11 mmol), 5 g (26.23 mmol) of 2-chloro-4-phenylpyrimidine and 130 ml of DMF were used to obtain the same composition as in Synthesis Example 4 3.22 g (yield 52%) of the target compound Inv1-5 were obtained by the method.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

Synthesis Example 6: Compound Inv1 - Synthesis of 9 - - Example 4

Synthesis using 0.79 g (32.79 mmol) NaH, 4.16 g (13.11 mmol) 10H-phenanthro [9,10-b] carbazole, 5 g (26.23 mmol) 6'-chloro-2,3'-bipyridine and 130 ml DMF In the same manner as in Example 4, 3.09 g (yield 50%) of the title compound Inv1-9 was obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthesis Example 7  : Compound Inv1 - Ten  synthesis]- Example 5

10H-phenanthro [9,10-b] carbazole 5.63 g (17.72 mmol), 5-bromo-2,2'-bipyridine 5 g (21.27 mmol), Pd ₂ (dba) ₃ 0.81 g (5 mol%), P (t-bu) ₃ 0.36 g (1.77 mmol), NaO (t-bu) 4.26 g (44.31 mmol), and 80 ml of Toluene were added and 3.43 g of the target compound Inv1-10 (yield) was obtained in the same manner as in Synthesis Example 3. 41%) was obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthesis Example 8  : Compound Inv1 - Fifteen  synthesis]- Example 6

10H-phenanthro [9,10-b] carbazole 4.25 g (13.39 mmol), 2- (4-bromophenyl) -4-phenylpyrimidine 5 g (16.07 mmol), Pd ₂ (dba) ₃ 0.61 g (5 mol%), 0.27 g (1.34 mmol) of P (t-bu) ₃ , 3.22 g (34.47 mmol) of NaO (t-bu), and 80 ml of Toluene were added and 2.9 g of Inv1-15 as a target compound was prepared in the same manner as in Synthesis Example 3. Yield 40%) was obtained.

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

[ Synthesis Example 9  : Compound Inv1 - 16  synthesis]- Example 7

10H-phenanthro [9,10-b] carbazole 11.53 g (36.32 mmol), 2- (4-bromophenyl) -4,6-diphenylpyrimidine 16.88 g (43.6 mmol), Pd ₂ (dba) ₃ 0.99 g (1.09 mmol) Inv1-16 8.62 of the target compound in the same manner as in Synthesis Example 3, using 1.76 ml (3.63 mmol) of P (t-bu) _3, 8.72 g (90.82 mmol) of NaO (t-bu), and 150 ml of Toluene. g (yield 38%) was obtained.

GC-Mass (Theoretical value: 623.24 g / mol, Measured value: 623 g / mol), Elemental Analysis: C, 88.58; H, 4.69; N, 6.74

[ Synthesis Example 10  : Compound Inv1 - 20 of  synthesis]- Example 8

Synthesis Example using 0.78 g (32.68 mmol) of NaH, 4.15 g (13.07 mmol) of 10H-phenanthro [9,10-b] carbazole, 7 g (26.15 mmol) of 4-chloro-2,6-diphenylpyrimidine, and 150 ml of DMF In the same manner as in 4, 3.51 g of a target compound Inv1-20 (yield 49%) was obtained.

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

[ Synthesis Example 11  : Compound Inv1 - 22 of  synthesis]- Example 9

NaH 0.94g (39.2mmol), 10H-phenanthro [9,10-b] carbazole 4.98g (15.7mmol) 50ml, 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 200 4.17 g (yield 42%) of the title compound Inv1-22 was obtained in the same manner as in Synthesis Example 4 using ml of DMF. GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol), Elemental Analysis: C, 86.51; H, 4.52; N, 8.97

[ Synthesis Example 12  : Compound Inv1 - 24 of  synthesis]- Example 10

9 g (28.36 mmol) 10 H-phenanthro [9,10-b] carbazole, 8 g (34.03 mmol), 6-bromo-2,2'-bipyridine, Pd ₂ (dba) ₃ 1.3 g (5 mol%), P 6.02 g of the target compound Inv1-24 (t-bu) ₃ 0.57 g (2.84 mmol), NaO (t-bu) 6.81 g (70.9 mmol), and 200 ml of Toluene in the same manner as in Synthesis Example 3 Yield 45%) was obtained. GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthesis Example 13  : Compound Inv1 - 25 of  synthesis]- Example 11

6.78 g (21.36 mmol) of 10H-phenanthro [9,10-b] carbazole, 7 g (25.63 mmol) of 2-bromo-1-phenyl-1H-benzo [d] imidazole, 0.98 g (5) of Pd ₂ (dba) ₃ mol%), P (t-bu) ₃ 0.43 g (2.14 mmol), NaO (t-bu) 5.13 g (53.39 mmol), and 200 ml of Toluene in the same manner as in Synthesis Example 3 using Inv1 as the target compound 4.25 g (42% yield) of -25 were obtained.

GC-Mass (Theoretical value: 509.19 g / mol, Measured value: 509 g / mol)

[ Synthesis Example 14  : Compound Inv1 - Of 34  synthesis]- Example 12

1) Synthesis of Compound A

2,4,6-trichloropyridine8g (44.4mmol), phenylboronic acid10.8g (88.8mmol), Pd (PPh ₃ ) ₄ 1.54g (1.33mmol), NaOH 5.3g (133.3mmol) under nitrogen, 100ml THF and distilled water It was suspended in 50ml and stirred at reflux for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane and dried over MgSO ₄ . After silica gel filtering and column with Hexane: Mc = 4: 1 (v / v) to give a compound A 7g (31%).

2) Synthesis of Inv1-34

NaH 0.78 g (32.68 mmol), 10H-phenanthro [9,10-b] carbazole, 4.15 g (13.07 mmol), Compound A 7 g (26.15 mmol), and 150 ml of DMF were used in the same manner as in Synthesis Example 4 3.51 g (49% yield) of Inv1-20 was obtained. GC-Mass (Theoretical value: 548.20 g / mol, Measured value: 548 g / mol)

[ Synthesis Example 15  : Compound Inv1 - Of 39  synthesis]- Example 13

0.79 g (32.81 mmol) NaH, 4.16 g (13.12 mmol) 10H-phenanthro [9,10-b] carbazole, 7 g (26.24 mmol) 6-chloro-4-phenyl-2,2'-bipyridine, and 150 ml DMF Inv1-39 2.66 g (yield 37%) of the target compound were obtained using the same method as in Synthesis Example 4. GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

[ Synthesis Example 16  : Compound Inv1 - 48 of  synthesis]- Example 14

Synthesis Example 4 was prepared using 1.1 g (45.9 mmol) of NaH, 5.83 g (18.36 mmol) of 10H-phenanthro [9,10-b] carbazole, 7 g (36.72 mmol) of 5-chloro-2-phenylpyrimidine, and 150 ml of DMF. In the same manner, 3.38 g (39% yield) of the title compound Inv1-48 were obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthesis Example 17  : Compound Inv1 - 52 of  synthesis]- Example 15

10H-phenanthro [9,10-b] carbazole 3.51 g (11.07 mmol), 4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole 5 g (13.29 mmol), Pd ₂ (dba) ₃ Synthesis Example 3 using 0.51 g (5 mol%), P (t-bu) ₃ 0.22 g (1.11 mmol), NaO (t-bu) 2.66 g (27.69 mmol), and 150 ml of Toluene 3.12 g (yield 46%) of the title compound Inv1-52 were obtained in the same manner as the same method.

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

[ Synthesis Example 18  : Compound Inv1 - Of 54  synthesis]- Example 16

NaH 1.1 g (45.66 mmol), 10H-phenanthro [9,10-b] carbazole, 5.8 g (18.27 mmol), 2-chloro-4-phenyl-1,3,5-triazine 7 g (36.53 mmol), and DMF 150 ml was used to obtain 3.71 g (yield 43%) of the title compound Inv1-54 in the same manner as in Synthesis example 4. GC-Mass (Theoretical value: 472.17 g / mol, Measured value: 472 g / mol)

[ Synthesis Example 19  : Compound Inv1 - 56 of  synthesis]- Example 17

Synthesis Example 4 was prepared using 0.94 g (39.34 mmol) of NaH, 5 g (15.74 mmol) of 10H-phenanthro [9,10-b] carbazole, 6 g (31.47 mmol) of 2-chloro-5-phenylpyrazine, and 150 ml of DMF. In the same manner, 2.75 g (37% yield) of the title compound Inv1-56 were obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

Synthesis Example 20: Compound Inv1 - 57 Synthesis of - Example 18

10H-phenanthro [9,10-b] carbazole 3.51 g (11.07 mmol), 3- (4-bromophenyl) -4,5-diphenyl-4H-1,2,4-triazole 5 g (13.29 mmol), Pd ₂ (dba) ₃ Synthesis Example 3 using 0.51 g (5 mol%), P (t-bu) ₃ 0.22 g (1.11 mmol), NaO (t-bu) 2.66 g (27.69 mmol), and 150 ml of Toluene In the same manner as in the title compound Inv1-57 2.85 g (yield 42%) was obtained.

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

[ Synthesis Example 21  : Compound Inv1 - Of 62  synthesis]- Example 19

Synthesis Example 4 was prepared using 0.95 g (39.55 mmol) of NaH, 5.02 g (15.82 mmol) of 10H-phenanthro [9,10-b] carbazole, 6 g (31.64 mmol) of 2-chloro-5-phenylpyridine, and 150 ml of DMF. In the same manner, 2.29 g (39% yield) of the title compound Inv1-62 were obtained.

GC-Mass (Theoretical value: 470.56 g / mol, Measured value: 470 g / mol)

Synthesis Example 22: Compound Inv1 - Synthesis of 63 - Example 20

10H-phenanthro [9,10-b] carbazole 7.91 g (24.91 mmol), 5-bromo-2-phenylpyridine 7 g (29.90 mmol), Pd ₂ (dba) ₃ 1.14 g (5 mol%), P (t- bu) ₃ 0.5 g (2.49 mmol), 5.99 g (62.3 mmol) NaO (t-bu), and 200 ml of Toluene in the same manner as in Synthesis Example 3 5.51 g of the target compound Inv1-63 (yield 47%) ) Was obtained.

GC-Mass (Theoretical value: 470.56 g / mol, Measured value: 470 g / mol)

Synthesis Example 23: Compound Inv1 - Synthesis of 66 - Example 21

10H-phenanthro [9,10-b] carbazole 3.79 g (11.93 mmol), 2-bromo-5,6-diphenyl-2H-benzo [d] imidazole 5 g (14.32 mmol), Pd ₂ (dba) ₃ 0.55 g (5 mol%), P (t-bu) ₃ 0.24 g (1.19 mmol), NaO (t-bu) 2.87 g (29.83 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 3.14 g (45% yield) of Inv1-66 was obtained.

GC-Mass (Theoretical value: 585.22 g / mol, Measured value: 585 g / mol)

[ Synthesis Example 24  : Compound Inv1 - 81 of  synthesis]- Example 22

10H-phenanthro [9,10-b] carbazole 3.79 g (11.93 mmol), 2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole 5 g (14.32 mmol), Pd ₂ (dba) ₃ 0.55 g (5 mol%), P (t-bu) ₃ 0.24 g (1.19 mmol), NaO (t-bu) 2.87 g (29.83 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 2.93 g (yield 42%) of Inv1-81 was obtained as a target compound.

GC-Mass (Theoretical value: 585.22 g / mol, Measured value: 585 g / mol)

[ Synthesis Example 25  : Compound Inv1 - 86 of  synthesis]- Example 23

10H-phenanthro [9,10-b] carbazole 3.79 g (11.93 mmol), 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole 5 g (14.32 mmol), Pd ₂ (dba) ₃ 0.55 g (5 mol%), P (t-bu) ₃ 0.24 g (1.19 mmol), NaO (t-bu) 2.87 g (29.83 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 2.87 g (yield 41%) of the desired compound, Inv1-86, were obtained.

GC-Mass (Theoretical value: 585.22 g / mol, Measured value: 585 g / mol)

[ Synthesis Example 26  : Compound Inv1 - Of 87  synthesis]- Example 24

10H-phenanthro [9,10-b] carbazole 3.79 g (11.93 mmol), 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole 5 g (14.32 mmol), Pd ₂ (dba) ₃ 0.55 g (5 mol%), P (t-bu) ₃ 0.24 g (1.19 mmol), NaO (t-bu) 2.87 g (29.83 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 3 g (yield 43%) of Inv1-87 was obtained as a target compound.

GC-Mass (Theoretical value: 585.22 g / mol, Measured value: 585 g / mol)

[ Synthesis Example 27  : Compound Inv1 - 88 of  synthesis]- Example 25

10 H-phenanthro [9,10-b] carbazole 3.79 g (11.93 mmol), 1- (3-bromophenyl) -2- (pyridin-2-yl) -1H-benzo [d] imidazole 5.02 g (14.32 mmol), Synthesis using 0.55 g (5 mol%) of Pd ₂ (dba) ₃ , 0.24 g (1.19 mmol) of P (t-bu) ₃ , 2.87 g (29.83 mmol) of NaO (t-bu), and 150 ml of Toluene In the same manner as in Example 3, 3.15 g (yield 45%) of the title compound Inv1-88 was obtained. GC-Mass (Theoretical value: 586.22 g / mol, Measured value: 586 g / mol)

Synthesis Example 28: Compound Inv1 - Synthesis of 89 - Example 26

10 H-phenanthro [9,10-b] carbazole 3.51 g (11.07 mmol), 3,3 '-(1- (4-bromophenyl) -1H-pyrrole-2,5-diyl) dipyridine 5 g (13.29 mmol), Synthesis using 0.51 g (5 mol%) of Pd ₂ (dba) ₃ , 0.22 g (1.11 mmol) of P (t-bu) ₃ , 2.66 g (27.69 mmol) of NaO (t-bu), and 150 ml of Toluene In the same manner as in Example 3, 2.99 g (yield 44%) of the title compound Inv1-89 was obtained.

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

Synthesis Example 29: Compound Inv1 - Synthesis of 91 - Example 27

Synthesis Example 4 was prepared using 1.77 g (73.69 mmol) of NaH, 9.36 g (15.82 mmol) of 10H-phenanthro [9,10-b] carbazole, 10 g (58.95 mmol) of 2-chlorobenzo [d] thiazole, and 250 ml of DMF. In the same manner, 5.44 g (41% yield) of the title compound Inv1-91 were obtained.

GC-Mass (Theoretical value: 450.12 g / mol, Measured value: 450 g / mol)

Synthesis Example 30: Compound Inv1 - Synthesis of 92 - Example 28

Synthesis Example 4 was prepared using 1.56 g (65.12 mmol) of NaH, 8.27 g (26.05 mmol) of 10H-phenanthro [9,10-b] carbazole, 8 g (52.09 mmol) of 2-chlorobenzo [d] oxazole, and 200 ml of DMF. In the same manner, 4.87 g (yield 43%) of the title compound Inv1-92 was obtained.

GC-Mass (Theoretical value: 434.14 g / mol, Measured value: 434 g / mol)

Synthesis Example 31: Compound Inv1 - Synthesis of 94 - Example 29

10 g-phenanthro [9,10-b] carbazole 4.84 g (15.26 mmol), 2-bromo-3-phenylimidazo [1,2-a] pyridine 5 g (18.31 mmol), Pd ₂ (dba) ₃ 0.7 g (5 mol%), P (t-bu) ₃ 0.31 g (1.53 mmol), NaO (t-bu) 3.67 g (38.14 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 using the target compound Inv1 3.94 g (43% yield) of -94 were obtained.

GC-Mass (Theoretical value: 509.19 g / mol, Measured value: 509 g / mol)

[ Synthesis Example 32  : Compound Inv1 - 95 of  synthesis]- Example 30

*

10 g-phenanthro [9,10-b] carbazole 4.82 g (15.2 mmol), 2- (3-bromophenyl) imidazo [1,2-a] pyrimidine 5 g (18.24 mmol), Pd ₂ (dba) ₃ 0.7 g ( 5 mol%), P (t-bu) ₃ 0.31 g (1.52 mmol), NaO (t-bu) 3.65 g (38.00 mmol) and 150 ml of Toluene in the same manner as in Synthesis Example 3 using the target compound Inv1 3.1 g (40% yield) of -95 were obtained. GC-Mass (Theoretical value: 510.18 g / mol, Measured value: 510 g / mol)

[ Synthesis Example 33  : Compound Inv1 - 97 of  synthesis]- Example 31

10 g-phenanthro [9,10-b] carbazole 4.82 g (15.2 mmol), 2- (4-bromophenyl) imidazo [1,2-a] pyrimidine 5 g (18.24 mmol), Pd ₂ (dba) ₃ 0.7 g ( 5 mol%), P (t-bu) ₃ 0.31 g (1.52 mmol), NaO (t-bu) 3.65 g (38.00 mmol), and 150 ml of Toluene were prepared in the same manner as in Synthesis Example 3 3.03 g (39% yield) of Inv1-95 were obtained. GC-Mass (Theoretical value: 510.18 g / mol, Measured value: 510 g / mol)

Synthesis Example 34: Compound Inv1 - 98 Synthesis of - Example 32

10H-phenanthro [9,10-b] carbazole 4.56 g (14.36 mmol), 2- (4-bromophenyl) benzo [d] thiazole 5 g (17.23 mmol), Pd ₂ (dba) ₃ 0.66 g (5 mol%) , Inv1-98 2.95 as a target compound in the same manner as in Synthesis Example 3, using 0.29 g (1.44 mmol) of P (t-bu) ₃ , 3.45 g (35.9 mmol) of NaO (t-bu), and 150 ml of Toluene. g (yield 39%) was obtained.

GC-Mass (Theoretical value: 526.15 g / mol, Measured value: 526 g / mol)

[ Synthesis Example 35  : Compound Inv1 - 100 of  synthesis]- Example 33

5.83 g (18.37 mmol), 2- (4-bromophenyl) imidazo [1,2-a] pyridine 6 g (22.05 mmol), Pd ₂ (dba) ₃ 0.84 g (10H-phenanthro [9,10-b] carbazole 5 mol%), P (t-bu) ₃ 0.37 g (1.84 mmol), NaO (t-bu) 4.41 g (45.93 mmol), and 150 ml of Toluene were used in the same manner as in Synthesis Example 3 3.84 g (41% yield) of Inv1-100 were obtained.

GC-Mass (Theoretical value: 509.19 g / mol, Measured value: 509 g / mol)

[ Synthesis Example 36  : Compound Inv1 - 131 of  synthesis]- Example 34

Synthesis Example 4 was prepared using 0.95 g (39.55 mmol) of NaH, 5.02 g (15.82 mmol) of 10H-phenanthro [9,10-b] carbazole, 6 g (31.64 mmol) of 2-chloro-3-phenylpyridine, and 200 ml of DMF. In the same manner, 3.28 g (yield 44%) of the title compound Inv1-131 was obtained.

GC-Mass (Theoretical value: 470.18 g / mol, Measured value: 470 g / mol)

Synthesis Example 37 Synthesis of Compound Inv1-132 Example 35

9 g (28.36 mmol) of 10H-phenanthro [9,10-b] carbazole, 8 g (134.3 mmol) of 5-bromo-2,3'-bipyridine, Pd ₂ (dba) ₃ 1.29 g (5 mol%), P (t-bu) ₃ 0.57 g (2.84 mmol), NaO (t-bu) 6.81 g (70.9 mmol), and 200 ml of Toluene in the same manner as in Synthesis Example 3 4.95 g (Inv1-132) Yield 37%) was obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthesis Example 38  : Compound Inv1 - 133 of  synthesis]- Example 36

10 h-phenanthro [9,10-b] carbazole 4.56 g (14.36 mmol), 5-bromo-2,4'-bipyridine 5 g (17.23 mmol), Pd ₂ (dba) ₃ 0.66 g (5 mol%), P 2.64 g of the target compound Inv1-133 (t-bu) ₃ 0.29 g (1.44 mmol), NaO (t-bu) 3.45 g (35.90 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 Yield 39%) was obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

Synthesis Example 39: Compound Inv1 - Synthesis of 134 - Example 37

6.38 g (20.10 mmol), 10-bromo-2,3'-bipyridine 7 g (24.12 mmol), Pd ₂ (dba) ₃ 0.92 g (5 mol%), P 10 H-phenanthro [9,10-b] carbazole (t-bu) ₃ 0.41 g (2.01 mmol), NaO (t-bu) 4.83 g (50.26 mmol), and 200 ml of Toluene were prepared in the same manner as in Synthesis Example 3. Yield 40%) was obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthesis Example 40  : Compound Inv1 - 135 of  synthesis]- Example 38

6.38 g (20.10 mmol), 10-bromo-2,4'-bipyridine 7 g (24.12 mmol), Pd ₂ (dba) ₃ 0.92 g (5 mol%), P 10H-phenanthro [9,10-b] carbazole (t-bu) ₃ 0.41 g (2.01 mmol), NaO (t-bu) 4.83 g (50.26 mmol), and 200 ml of Toluene were prepared in the same manner as in Synthesis Example 3. Yield 42%).

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

Synthesis Example 41: Compound Inv1 - Synthesis of 136 - Example 39

NaH 0.78 g (32.44 mmol), 10H-phenanthro [9,10-b] carbazole 4.12 g (12.98 mmol), 2-chloro-4,6-di (pyridin-3-yl) -1,3,5-triazine 7 g (25.96 mmol) and 150 ml of DMF were used to obtain 3.01 g (yield 43%) of Inv1-136 as a target compound in the same manner as in Synthesis example 4. GC-Mass (Theoretical value: 550.19 g / mol, Measured value: 550 g / mol)

Synthesis Example 42: Compound Inv1 - Synthesis of 137 - Example 40

NaH 0.67 g (27.81 mmol), 10H-phenanthro [9,10-b] carbazole 3.53 g (11.12 mmol), 2-chloro-4,6-di (pyridin-4-yl) -1,3,5-triazine 6 g (22.25 mmol) and 150 ml of DMF were used to obtain 2.82 g (yield 63%) of Inv1-137 as a target compound in the same manner as in Synthesis example 4. GC-Mass (Theoretical value: 550.19 g / mol, Measured value: 550 g / mol)

[ Synthesis Example 43  : Compound Inv1 - Of 138  synthesis]- Example 41

10 H-phenanthro [9,10-b] carbazole 4.53 g (14.28 mmol), 1- (6-bromopyridin-2-yl) -2-phenyl-1H-benzo [d] imidazole 6 g (17.13 mmol), Pd ₂ (dba) ₃ 0.65 g (5 mol%), P (t-bu) ₃ 0.29 g (1.43 mmol), NaO (t-bu) 3.43 g (35.69 mmol), and 150 ml of Toluene 3.27 g (yield 39%) of the title compound Inv1-138 was obtained by the same method as described above.

GC-Mass (Theoretical value: 586.22 g / mol, Measured value: 586 g / mol)

Synthesis Example 44: Compound Inv1 - Synthesis of 139 - Example 42

4.54 g (14.31 mmol) of 10H-phenanthro [9,10-b] carbazole, 5 g (17.17 mmol) of 2- (5-bromopyridin-2-yl) benzo [d] thiazole, 0.66 g of Pd ₂ (dba) ₃ 5 mol%), P (t-bu) ₃ 0.29 g (1.43 mmol), NaO (t-bu) 3.44 g (35.78 mmol), and 150 ml of Toluene were used in the same manner as in Synthesis Example 3 2.94 g (39% yield) of Inv1-139 were obtained.

GC-Mass (Theoretical value: 527.15 g / mol, Measured value: 527 g / mol)

Synthesis Example 45: Compound Inv1 - Synthesis of 141 - Example 43

Synthesis Example using 0.56 g (23.12 mmol) of NaH, 2.99 g (9.41 mmol) of 10H-phenanthro [9,10-b] carbazole, 5 g (18.81 mmol) of 4-chloro-2,6-diphenylpyridine, and 150 ml of DMF 2.16 g (yield 42%) of the title compound Inv1-141 were obtained by the same method as the method described above.

GC-Mass (Theoretical value: 546.21 g / mol, Measured value: 546 g / mol)

Synthesis Example 46: Compound Inv1 - Synthesis of 142 - Example 44

Synthesis Example using 0.79 g (32.93 mmol) of NaH, 4.18 g (13.17 mmol) of 10H-phenanthro [9,10-b] carbazole, 7 g (26.34 mmol) of 2-chloro-4,6-diphenylpyridine, and 150 ml of DMF In the same manner as in 4, 3.1 g (yield 43%) of Inv1-142 as a target compound was obtained.

GC-Mass (Theoretical value: 546.21 g / mol, Measured value: 546 g / mol)

[ Synthesis Example 47  : Compound Inv1 - 143 of  synthesis]- Example 45

10 g-phenanthro [9,10-b] carbazole 3.4 g (10.71 mmol), 2,2 '-(5-bromo-1,3-phenylene) dipyridine 4 g (12.85 mmol), Pd ₂ (dba) ₃ 0.49 g (5 mol%), P (t-bu) ₃ 0.22 g (1.07 mmol), NaO (t-bu) 2.57 g (26.78 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 2.52 g (43% yield) of Inv1-143 was obtained.

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

Synthesis Example 48: Compound Inv1 - Synthesis of 144 - Example 46

6.38 g (20.10 mmol), 2- (benzo [b] thiophen-2-yl) -5-bromopyridine 7 g (24.12 mmol), Pd ₂ (dba) ₃ 0.92 g 10H-phenanthro [9,10-b] carbazole (5 mol%), P (t-bu) ₃ 0.41 g (2.01 mmol), NaO (t-bu) 4.83 g (50.26 mmol), and 200 ml of Toluene in the same manner as in Synthesis Example 3 4.34 g (41% yield) of Phosphorus Inv1-144 was obtained.

GC-Mass (Theoretical value: 526.15 g / mol, Measured value: 526 g / mol)

Synthesis Example 49: Compound Inv1 - Synthesis of 145 - Example 47

Synthesis Example 4 was prepared using 0.94 g (39.34 mmol) of NaH, 5 g (15.74 mmol) of 10H-phenanthro [9,10-b] carbazole, 6 g (31.47 mmol) of 4-chloro-2-phenylpyrimidine, and 200 ml of DMF. In the same manner, 3.27 g (yield 44%) of the title compound Inv1-145 was obtained. GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

Synthesis Example 50: Compound Inv1 - 146: Synthesis of - Example 48

Synthesis Example 4 was prepared using 0.94 g (39.34 mmol) of NaH, 5 g (15.74 mmol) of 10H-phenanthro [9,10-b] carbazole, 6 g (31.47 mmol) of 2-chloro-5-phenylpyrimidine, and 200 ml of DMF. In the same manner, 3.34 g (yield 45%) of the desired compound, Inv1-146, was obtained. GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

Synthesis Example 51: Compound Inv1 - Synthesis of 147 - Example 49

10H-phenanthro [9,10-b] carbazole 3.41 g (10.76 mmol), 4- (4-bromophenyl) -2,6-diphenylpyrimidine 5 g (12.91 mmol), Pd ₂ (dba) ₃ 0.49 g (5 mol% ), P (t-bu) ₃ 0.22 g (1.08 mmol), NaO (t-bu) 2.58 g (26.90 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 using the target compound Inv1-147 2.55 g (yield 38%) were obtained.

GC-Mass (Theoretical value: 623.24 g / mol, Measured value: 623 g / mol)

Synthesis Example 52: Compound Inv1 - Synthesis of 148 - Example 50

10 g-phenanthro [9,10-b] carbazole 5.81 g (18.31 mmol), 2- (2-bromophenyl) imidazo [1,2-a] pyridine 6 g (21.97 mmol), Pd ₂ (dba) ₃ 0.83 g ( 5 mol%), P (t-bu) ₃ 0.37 g (1.83 mmol), NaO (t-bu) 4.4 g (45.77 mmol), and 150 ml of Toluene were used in the same manner as in Synthesis Example 3 3.64 g (39% yield) of Inv1-148 were obtained. GC-Mass (Theoretical value: 509.19 g / mol, Measured value: 509 g / mol)

Synthesis Example 53: Compound Inv1 - Synthesis of 149 - Example 51

* 10H-phenanthro [9,10-b ] carbazole 4.56 g (14.36 mmol), 3-bromoquinoline 5 g (17.23 mmol), Pd 2 (dba) 3 0.66 g (5 mol%), P (t-bu) 3 3.02 g (yield 40%) of the target compound was obtained in the same manner as in Synthesis Example 3 using 0.29 g (1.44 mmol), 3.45 g (35.90 mmol) of NaO (t-bu), and 150 ml of Toluene. It was.

GC-Mass (Theoretical value: 526.15 g / mol, Measured value: 526 g / mol)

[ Synthesis Example 54  Compound 2- (4- bromo -2- nitrophenyl ) triphenylene Synthesis of

1,4-dibromo-2-nitrobenzene 25.81 g (91.87 mmol), triphenylen-2-ylboronic acid 30 g (110.25 mmol), Pd (PPh ₃ ) ₄ 5.31 g (5 mol%), NaOH 11.02 g (275.62 mmol), And THF / distilled water (300ml / 150ml) was tested in the same manner as in Synthesis Example 1 to obtain 35 g (yield 89%) of the target compound 2- (4-bromo-2-nitrophenyl) triphenylene.

¹ H NMR: 7.35 (t, 1H), 7.52 (t, 1H), 7.71 (m, 4H), 8.20 (d, 1H), 8.35 (d, 1H), 8.59 (d, 1H), 8.68 (d, 1H), 8.77 (d, 2H), 8.99 (d, 1H), 9.04 (s, 1H)

[ Synthesis Example 55  Compound 2- (5- bromo -2- nitrophenyl ) triphenylene Synthesis of

2,4-dibromo-1-nitrobenzene 25.81 g (91.87 mmol), triphenylen-2-ylboronic acid 30 g (110.25 mmol), Pd (PPh ₃ ) ₄ 5.31 g (5 mol%), NaOH 11.02 g (275.62 mmol), And THF / distilled water (300ml / 150ml) was tested in the same manner as in Synthesis Example 1 to obtain 34.23g (yield 87%) of the target compound 2- (5-bromo-2-nitrophenyl) triphenylene.

¹ H NMR: 7.36 (t, 1H), 7.52 (t, 1H), 7.71 (m, 4H), 8.11 (d, 1H), 8.24 (d, 1H), 8.56 (d, 1H), 8.65 (d, 1H), 8.74 (d, 2H), 8.93 (d, 1H), 9.02 (s, 1H)

[ Synthesis Example 56  Compound 2- bromo -7- (2- nitrophenyl ) triphenylene Synthesis of

2,7-dibromotriphenylene 30 g (77.7 mmol), 2-nitrophenylboronic acid 15.57 g (93.24 mmol), Pd (PPh ₃ ) ₄ 4.49 g (5 mol%), NaOH 32.22 g (233.11 mmol), and THF / distilled water ( 300ml / 150ml) was used in the same manner as in Synthesis Example 1 to obtain 20.3 g (yield 61%) of the target compound, 2-bromo-7- (2-nitrophenyl) triphenylene.

¹ H NMR: 7.41 (t, 1H), 7.66 (t, 1H), 7.75 (m, 4H), 8.13 (d, 1H), 8.25 (d, 1H), 8.55 (d, 1H), 8.63 (d, 1H), 8.72 (d, 2H), 8.95 (m, 2H).

[ Synthetic example  57]

[ Synthetic example  57-1: Compound 12- bromo -10H- phenanthro [Synthesis of 9,10-b] carbazole]

[ Synthetic example  57-2: Compound 13- bromo -15H- phenanthro [Synthesis of 9,10-a] carbazole]

30-g (81.72mmol) of 2- (4-bromo-2-nitrophenyl) triphenylene, 53.59g (204.31mmol) of triphenyl phosphine, and 100 ml of 1,2-dichlorobenzene were used in the same manner as in Synthesis Example 2 to obtain 12- 9.66 g (yield 32%) of bromo-10H-phenanthro [9,10-b] carbazole and 11.66 g (yield 42%) of 13-bromo-15H-phenanthro [9,10-a] carbazole were obtained, respectively.

Synthesis Example 57-1 (12-bromo-10H-phenanthro [9,10-b] carbazole): ¹ H NMR: 7.32 (t, 1H), 7.50 (t, 1H), 7.73 (m, 4H), 8.19 ( s, 1H), 8.37 (d, 1H), 8.59 (d, 1H), 8.70 (s, 1H), 8.79 (d, 2H), 8.97 (s, 1H), 9.15 (s, 1H).

Synthesis Example 57-2 (13-bromo-15H-phenanthro [9,10-a] carbazole): ¹ H NMR: 7.36 (t, 1H), 7.51 (t, 1H), 7.72 (m, 4H), 8.20 ( d, 1H), 8.37 (d, 1H), 8.59 (d, 1H), 8.70 (d, 1H), 8.79 (d, 1H), 8.97 (d, 2H), 9.15 (s, 1H).

[ Synthetic example  58]

[ Synthetic example  58-1: Compound 13- bromo -10H- phenanthro [Synthesis of 9,10-b] carbazole]

[ Synthetic example  58-2: Compound 12- bromo -15H- phenanthro [Synthesis of 9,10-a] carbazole]

2- (5-bromo-2-nitrophenyl) triphenylene 30g (81.72mmol), triphenyl phosphine 53.59g (204.31mmol), 1,2-dichlorobenzene 100ml in the same manner as in Synthesis Example 2 13-bromo 10.56 g (yield 35%) of -10H-phenanthro [9,10-b] carbazole and 12.21 g (44% yield) of 12-bromo-10H-phenanthro [9,10-b] carbazole were obtained, respectively.

Synthesis Example 58-1 (13-bromo-10H-phenanthro [9,10-b] carbazole): ¹ H NMR: 7.36 (t, 1H), 7.54 (t, 1H), 7.77 (m, 4H), 8.20 ( s, 1H), 8.39 (d, 1H), 8.61 (d, 1H), 8.71 (s, 1H), 8.82 (d, 2H), 8.95 (s, 1H), 9.11 (s, 1H).

Synthesis Example 58-2 (12-bromo-15H-phenanthro [9,10-a] carbazole): ¹ H NMR: 7.34 (t, 1H), 7.53 (t, 1H), 7.73 (m, 4H), 8.19 ( d, 1H), 8.35 (d, 1H), 8.60 (d, 1H), 8.71 (d, 1H), 8.77 (d, 1H), 8.96 (d, 2H), 9.13 (s, 1H).

[ Synthetic example  59]

[ Synthetic example  59-1: Compound 6- bromo -10H- phenanthro [Synthesis of 9,10-b] carbazole]

[ Synthetic example  59-2: Compound 6- bromo -15H- phenanthro [Synthesis of 9,10-a] carbazole]

6-bromo, the target substance, in the same manner as in Synthesis Example 2, using 20 g (46.70 mmol) of 2-bromo-7- (2-nitrophenyl) triphenylene, 30.62 g (116.75 mmol) of triphenyl phosphine, and 80 ml of 1,2-dichlorobenzene 6.66 g of -10H-phenanthro [9,10-b] carbazole (36% yield) and 8.11 g of 6-bromo-15H-phenanthro [9,10-a] carbazole (47% yield) were obtained, respectively.

Synthesis Example 59-1 (6-bromo-10H-phenanthro [9,10-b] carbazole): ¹ H NMR: 7.36 (t, 1H), 7.51 (t, 1H), 7.70 (d, 2H), 8.22 ( s, 1H), 8.37 (d, 2H), 8.64 (d, 2H), 8.75 (s, 1H), 8.80 (d, 2H), 8.93 (d, 1H), 9.16 (s, 1H).

Synthesis Example 59-2 (6-bromo-15H-phenanthro [9,10-a] carbazole): ¹ H NMR: 7.34 (t, 1H), 7.53 (t, 1H), 7.73 (d, 2H), 8.19 ( d, 1H), 8.35 (d, 2H), 8.60 (d, 2H), 8.71 (d, 1H), 8.77 (d, 2H), 8.96 (d, 1H), 9.12 (s, 1H).

[ Synthetic example  60: compound 12- ( pyridine -2- yl ) -10H- phenanthro [9,10-b] carbazole Synthesis of

5 g (12.62 mmol) of 12-bromo-10H-phenanthro [9,10-b] carbazole, 1.86 g (15.14 mmol) of pyridin-2-ylboronic acid, Pd (PPh ₃ ) ₄ 0.79 g (5 mol%), NaOH Experiment with 1.51 g (37.85 mmol) and THF / distilled water (80ml / 40ml) in the same manner as in Synthesis example 1 to obtain the target compound 12- (pyridin-2-yl) -10H-phenanthro [9,10-b ] 3.93 g (yield 79%) of carbazole were obtained. GC-Mass (Theoretical value: 394.15 g / mol, Measured value: 394 g / mol)

Synthesis Example 61: Compound 13- (pyridin -2- yl) -10H- phenanthro [9,10-b] carbazole in the synthesis]

13-bromo-10H-phenanthro [9,10-b] carbazole 5 g (12.62 mmol), pyridin-2-ylboronic acid 1.86 g (15.14 mmol), Pd (pph ₃ ) ₄ 0.79 g (5 mol%), NaOH Experiment with 1.51 g (37.85 mmol) and THF / distilled water (80ml / 40ml) in the same manner as in Synthesis example 1 to obtain the target compound 13- (pyridin-2-yl) -10H-phenanthro [9,10-b ] 3.88 g (yield 78%) of carbazole were obtained. GC-Mass (Theoretical value: 394.15 g / mol, Measured value: 394 g / mol)

Synthesis Example 62: A mixture of 6- (pyridin -2- yl) -10H- phenanthro [9,10-b] carbazole in the synthesis]

6-bromo-10H-phenanthro [9,10-b] carbazole 5 g (12.62 mmol), pyridin-2-ylboronic acid 1.86 g (15.14 mmol), Pd (pph ₃ ) ₄ 0.79 g (5 mol%), NaOH Experiment with 1.51 g (37.85 mmol) and THF / distilled water (80ml / 40ml) in the same manner as in Synthesis example 1 to obtain the target compound 6- (pyridin-2-yl) -10H-phenanthro [9,10-b ] Carbazole 4.03 g (yield 81%) was obtained. GC-Mass (Theoretical value: 394.15 g / mol, Measured value: 394 g / mol)

[ Synthesis Example 63  : Compound Inv2 Synthesis of -12 Example 52

NaH 0.53 g (22.18 mmol), 13- (pyridin-2-yl) -10H-phenanthro [9,10-b] carbazole 3.5 g (8.87 mmol), 2-chloro-4,6-diphenyl-1,3, 4.75 g (17.75 mmol) of 5-triazine and 150 ml of DMF were used to obtain 2.28 g (yield 41%) of the title compound Inv2-12 in the same manner as in Synthesis example 4. GC-Mass (Theoretical value: 625.23 g / mol, Measured value: 625 g / mol)

[ Synthesis Example 64  : Compound Inv2 Synthesis of -62]- Example 53

NaH 0.76 g (31.69 mmol), 6- (pyridin-2-yl) -10H-phenanthro [9,10-b] carbazole 5 g (12.68 mmol), 2-chloro-4,6-diphenyl-1,3, 6.79 g (25.35 mmol) of 5-triazine and 200 ml of DMF were used to obtain 3.41 g (yield 43%) of the title compound Inv2-62 in the same manner as in Synthesis example 4. GC-Mass (Theoretical value: 625.23 g / mol, Measured value: 625 g / mol)

[ Synthesis Example 65  : Compound Inv2 Synthesis of -106]- Example 54

12- (pyridin-2-yl) -10H-phenanthro [9,10-b] carbazole 4.91 g (12.46 mmol), 2-bromo-6-phenylpyridine 3.5 g (14.95 mmol), Pd ₂ (dba) ₃ 0.57 g (5 mol%), P (t-bu) ₃ 0.25 g (1.25 mmol), NaO (t-bu) 2.99 g (31.15 mmol), and 150 ml of Toluene in the same manner as in Synthesis Example 3 2.8 g (41% yield) of Inv2-106 was obtained.

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

Synthesis Example 66: Compound 13- (4,6- diphenyl -1,3,5- triazin -2- yl ) -10H- phenan Synthesis of thro [9,10-b] carbazole]

13-bromo-10H-phenanthro [9,10-b] carbazole 5 g (13.54 mmol), 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid 4.5 g (16.25 mmol), Pd (PPh ₃ ) ₄ 0.78 g (5 mol%), NaOH 1.62 g (40.62 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 to the target compound 13- (4,6- 5.57 g (yield 75%) of diphenyl-1,3,5-triazin-2-yl) -10H-phenan thro [9,10-b] carbazole were obtained.

GC-Mass (Theoretical value: 548.20 g / mol, Measured value: 548 g / mol)

Synthesis Example 67: Compound 12- (4,6- diphenyl -1,3,5- triazin -2- yl ) -10H- phenan Synthesis of thro [9,10-b] carbazole]

5 g (13.54 mmol) of 12-bromo-10H-phenanthro [9,10-b] carbazole, 4.5 g (16.25 mmol) of 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid, Pd (PPh ₃ ) ₄ 0.78 g (5 mol%), NaOH 1.62 g (40.62 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 to obtain the target compound 12- (4,6- 5.72 g (yield 77%) of diphenyl-1,3,5-triazin-2-yl) -10H-phenan thro [9,10-b] carbazole were obtained.

GC-Mass (Theoretical value: 548.20 g / mol, Measured value: 548 g / mol)

Synthesis Example 68: A mixture of 6- (4,6- diphenyl -1,3,5- triazin -2- yl ) -10H- phenan Synthesis of thro [9,10-b] carbazole]

5 g (13.54 mmol) of 6-bromo-10H-phenanthro [9,10-b] carbazole, 4.5 g (16.25 mmol) of 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid, Pd (PPh ₃ ) ₄ 0.78 g (5 mol%), NaOH 1.62 g (40.62 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 to the target compound 6- (4,6- 5.5 g (74% yield) of diphenyl-1,3,5-triazin-2-yl) -10H-phenan thro [9,10-b] carbazole were obtained.

GC-Mass (Theoretical value: 548.20 g / mol, Measured value: 548 g / mol)

[ Synthetic example  69: compound Inv2 Synthesis of -159]- Example 55

13- (4,6-diphenyl-1,3,5-triazin-2-yl) -10H-phenanthro [9,10-b] carbaz ole 5.88 g (10.73 mmol), 3-bromobiphenyl 3 g (12.87 mmol) Using 0.49 g (5 mol%) of Pd ₂ (dba) ₃ , 0.22 g (1.07 mmol) of P (t-bu) ₃ , 2.58 g (26.81 mmol) of NaO (t-bu), and 150 ml of Toluene. In the same manner as in Synthesis Example 3, 2.68 g (yield 40%) of the title compound Inv2-159 was obtained.

GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol)

[ Synthesis Example 70  : Compound Inv2 -196 Synthesis]- Example 56

12- (4,6-diphenyl-1,3,5-triazin-2-yl) -10H-phenanthro [9,10-b] carbaz ole 4.26 g (7.76 mmol), 3-bromo-9-phenyl-9H -carbazole 3 g (9.31 mmol), Pd ₂ (dba) ₃ 0.36 g (5 mol%), P (t-bu) ₃ 0.16 g (0.78 mmol), NaO (t-bu) 1.86 g (19.4 mmol), Then, using 150 ml of Toluene, 1.99 g (yield 41%) of the title compound Inv2-196 was obtained in the same manner as in Synthesis example 3. GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol)

[ Synthesis Example 71  : Compound Inv2 Synthesis of -215] Example 57

6- (4,6-diphenyl-1,3,5-triazin-2-yl) -10H-phenanthro [9,10-b] carbaz ole 6.72 g (12.25 mmol), iodobenzene 3 g (14.71 mmol), Pd ₂ (dba) ₃ 0.56 g (5 mol%), P (t-bu) ₃ 0.25 g (1.23 mmol), NaO (t-bu) 2.94 g (30.64 mmol), and 200 ml of Toluene 2.99 g (yield 39%) of the title compound Inv2-215 was obtained in the same manner as in 3.

GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol)

Synthesis Example 72: Compound 13- bromo -10- (naphthalen -1- yl) -10H- phenanthro [9,10- b] carbazole in the synthesis]

13-bromo-10H-phenanthro [9,10-b] carbazole 7.97 g (20.12 mmol), 1-bromonaphthalene 5 g (24.15 mmol), Pd ₂ (dba) ₃ 0.92 g (5 mol%), P (t- bu) ₃ 0.41 g (2.01 mmol), NaO (t-bu) 4.83 g (50.31 mmol), and 200 ml of Toluene were used in the same manner as in Synthesis Example 3 to obtain 13-bromo-10- (naphthalen- 6.52 g (yield 62%) of 1-yl) -10H-phenanthro [9,10-b] carbazole was obtained.

GC-Mass (Theoretical value: 521.08 g / mol, Measured value: 521 g / mol)

Synthesis Example 73: Compound 10- (biphenyl -4- yl) -13- bromo -10H- phenanthro [9,10- b] carbazole in the synthesis]

13-bromo-10H-phenanthro [9,10-b] carbazole 5.89 g (14.88 mmol), 4-iodobiphenyl 5 g (17.85 mmol), Pd ₂ (dba) ₃ 0.68 g (5 mol%), P (t- bu) ₃ 0.3 g (1.49 mmol), NaO (t-bu) 3.57 g (37.19 mmol), and 200 ml of Toluene were used as the target compound 10- (biphenyl-4-yl) in the same manner as in Synthesis Example 3. 4.9 g (60% yield) of -13-bromo-10H-phenanthro [9,10-b] carbazole was obtained.

GC-Mass (Theoretical value: 548.09 g / mol, Measured value: 548 g / mol)

Synthesis Example 74: Compound 12- bromo -10- phenyl -10H- phenanthro [9,10 -b] Synthesis of carba zole]

12-bromo-10H-phenanthro [9,10-b] carbazole 8.1 g (20.42 mmol), iodobenzene 5 g (24.51 mmol), Pd ₂ (dba) ₃ 0.94 g (5 mol%), P (t-bu) ₃ 0.41 g (2.04 mmol), 4.91 g (51.06 mmol) NaO (t-bu), and 200 ml of Toluene were used in the same manner as in Synthesis Example 3 to obtain 12-bromo-10-phenyl-10H-phenanthro 5.06 g (63% yield) of [9,10-b] carbazole were obtained. GC-Mass (Theoretical value: 393.15 g / mol, Measured value: 393 g / mol)

Synthesis Example 75: Compound 13- bromo -10- (naphthalen -2- yl) -10H- phenanthro [9,10- b] carbazole in the synthesis]

13-bromo-10H-phenanthro [9,10-b] carbazole 7.97 g (20.12 mmol), 2-bromonaphthalene 5 g (24.15 mmol), Pd ₂ (dba) ₃ 0.92 g (5 mol%), P (t- bu) ₃ 0.41 g (2.01 mmol), NaO (t-bu) 4.83 g (50.31 mmol), and 200 ml of Toluene were used in the same manner as in Synthesis Example 3 to obtain 13-bromo-10- (naphthalen- 5.89 g (56% yield) of 2-yl) -10H-phenanthro [9,10-b] carbazole was obtained.

GC-Mass (Theoretical value: 521.08 g / mol, Measured value: 521 g / mol)

Synthesis Example 76: Compound 12- bromo -10- (naphthalen -2- yl) -10H- phenanthro [9,10- b] carbazole in the synthesis]

12-bromo-10H-phenanthro [9,10-b] carbazole 7.97 g (20.12 mmol), 2-bromonaphthalene 5 g (24.15 mmol), Pd ₂ (dba) ₃ 0.92 g (5 mol%), P (t- bu) ₃ 0.41 g (2.01 mmol), NaO (t-bu) 4.83 g (50.31 mmol), and 200 ml of Toluene were used in the same manner as in Synthesis Example 3 to obtain 12-bromo-10- (naphthalen- 6.41 g (61% yield) of 2-yl) -10H-phenanthro [9,10-b] carbazole were obtained.

GC-Mass (Theoretical value: 521.08 g / mol, Measured value: 521 g / mol)

[ Synthetic example  77: compound Inv3 Synthesis of -8 Example  58

6.02 g (11.53 mmol) of 13-bromo-10- (naphthalen-1-yl) -10H-phenanthro [9,10-b] carbazole, N- (biphenyl-4-yl) -9,9-dimethyl-9H- fluoren-2-amine 5 g (13.83 mmol), Pd ₂ (dba) ₃ 0.53 g (5 mol%), P (t-bu) ₃ 0.23 g (1.15 mmol), NaO (t-bu) 2.77 g (28.82 mmol), and 6.01 g (yield 65%) of the target compound Inv3-8 were obtained in the same manner as in Synthesis Example 3 using 200 ml of Toluene. GC-Mass (Theoretical value: 802.33 g / mol, Measured value: 802 g / mol)

[ Synthetic example  78: compound Inv3 Synthesis of -16 Example  59

10- (biphenyl-4-yl) -13-bromo-10H-phenanthro [9,10-b] carbazole 6.32 g (11.53 mmol), N- (biphenyl-4-yl) -9,9-dimethyl-9H- fluoren-2-amine 5 g (13.83 mmol), Pd ₂ (dba) ₃ 0.53 g (5 mol%), P (t-bu) ₃ 0.23 g (1.15 mmol), NaO (t-bu) 2.77 g (28.82 mmol), and 6.4 g (yield 67%) of the target compound Inv3-16 were obtained in the same manner as in Synthesis Example 3 using 200 ml of Toluene. GC-Mass (Theoretical value: 829.35 g / mol, Measured value: 829 g / mol)

[ Synthetic example  79: compound Inv3 Synthesis of -31 Example  60

12-bromo-10-phenyl-10H-phenanthro [9,10-b] carbazole 8.98 g (19.00 mmol), N-phenylnaphthalen-1-amine 5 g (22.80 mmol), Pd ₂ (dba) ₃ 0.87 g (5 mol%), P (t-bu) ₃ 0.38 g (1.90 mmol), NaO (t-bu) 4.57 g (47.50 mmol), and 200 ml of Toluene in the same manner as in Synthesis Example 3 using Inv3 7.31 g (63% yield) were obtained.

GC-Mass (Theoretical value: 610.24 g / mol, Measured value: 610 g / mol)

[ Synthetic example  80: compound Inv3 Synthesis of -50 Example  61

12-bromo-10-phenyl-10H-phenanthro [9,10-b] carbazole 5.44 g (11.52 mmol), N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine 5 g (13.83 mmol), Pd ₂ (dba) ₃ 0.53 g (5 mol%), P (t-bu) ₃ 0.23 g (1.15 mmol), NaO (t-bu) 2.77 g (28.82 mmol), and 200 ml 5.81 g (yield 67%) of the target compound Inv3-50 was obtained in the same manner as in Synthesis Example 3 using Toluene. GC-Mass (Theoretical value: 752.32 g / mol, Measured value: 752 g / mol)

[ Synthetic example  81: Compound Inv4 Synthesis of -6 Example  62

10- (biphenyl-4-yl) -13-bromo-10H-phenanthro [9,10-b] carbazole 5 g (9.12 mmol), 4- (naphthalen-1-yl (phenyl) amino) phenylboronic acid 3.71 g ( 10.94 mmol), Pd (PPh ₃ ) ₄ 0.53 g (5 mol%), NaOH 1.09 g (27.35 mmol), and THF / distilled water (100 ml / 50 ml) were tested in the same manner as in Synthesis Example 1 to obtain the target compound. 5 g (72% yield) of Inv4-6 were obtained. GC-Mass (Theoretical value: 762.30 g / mol, Measured value: 762 g / mol)

[ Synthetic example  82: compound Inv4 -11 Synthesis]- Example  63

13-bromo-10- (naphthalen-2-yl) -10H-phenanthro [9,10-b] carbazole 5 g (9.57 mmol), 4- (naphthalen-2-yl (phenyl) amino) phenylboronic acid 3.9 g ( 11.48 mmol), Pd (PPh ₃ ) ₄ 0.55 g (5 mol%), NaOH 1.15 g (28.71 mmol), and THF / distilled water (100 ml / 50 ml) were tested in the same manner as in Synthesis Example 1 to obtain the target compound. 5.29 g (75% yield) of Inv4-11 were obtained. GC-Mass (Theoretical value: 736.29 g / mol, Measured value: 736 g / mol)

[ Synthetic example  83: Compound Inv4 Synthesis of -28 Example  64

13-bromo-10-phenyl-10H-phenanthro [9,10-b] carbazole 5 g (10.58 mmol), 4- (naphthalen-1-yl (phenyl) amino) phenylboronic acid 4.31 g (12.70 mmol), Pd ( PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 5.38 g ( Yield 74%). GC-Mass (Theoretical value: 686.27 g / mol, Measured value: 686 g / mol)

[ Synthetic example  84: Compound Inv4 Synthesis of -48 Example  65

12-bromo-10- (naphthalen-2-yl) -10H-phenanthro [9,10-b] carbazole 5 g (9.57 mmol), 4- (biphenyl-4-yl (9,9-dimethyl-9H-fluoren -2-yl) amino) phenylboronic acid using 5.53 g (11.48 mmol), Pd (PPh ₃ ) ₄ 0.55 g (5 mol%), NaOH 1.15 g (28.71 mmol), and THF / distilled water (100ml / 50ml) Experiment in the same manner as in Synthesis Example 1 to obtain 6.48 g (yield 77%) of the title compound Inv4-48.

GC-Mass (Theoretical value: 878.37 g / mol, Measured value: 878 g / mol)

[ Synthetic example  85: compound 15- (6- bromopyridin -2- yl ) -15H- phenanthro [9,10-a] Synthesis of carbazole]

30 g (94.56 mmol) of 15H-phenanthro [9,10-a] carbazole, 33.6 g (141.84 mmol) of 2,6-dibromopyridine, 0.6 g (9.46 mmol) of Cu powder, 13.07 g (94.56 K ₂ CO ₃ ) under nitrogen stream mmol), 13.43 g (94.56 mmol) of Na ₂ SO ₄ , and 300 ml of nitrobenzene were added and stirred at 190 ° C. for 24 hours. After completion of the reaction, nitrobenzene was removed, extracted with dichloromethane, and the organic layer was dried over MgSO ₄ . The solvent removed was reacted with Hexane: MC = 3: 1 (v / v) to give 15.23 g (15- (6-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole as the target compound. Yield 34%) was obtained.

¹ H NMR: 6.42 (d, 1H), 6.94 (t, 1H), 7.11 (t, 1H), 7.23 (d, 1H), 7.44 (m, 2H), 7.54 (t, 1H), 7.69 (m, 2H), 8.21 (d, 1H), 8.35 (m, 3H), 8.51 (d, 1H), 8.64 (m, 2H), 8.71 (d, 1H).

[ Synthetic example  86: compound 15- (5- bromopyridin -2- yl ) -15H- phenanthro [9,10-a] Synthesis of carbazole]

15H-phenanthro [9,10-a] carbazole 17.86 g (56.28 mmol), 2,5-dibromopyridine 20 g (84.43 mmol), Cu powder 0.36 g (5.63 mmol), K ₂ CO ₃ 7.78 g (56.28 mmol), 7.99 g (56.28 mmol) of Na ₂ SO ₄ and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10] as a target compound. -a] carbazole was obtained 18.38 g (69% yield).

¹ H NMR: 6.43 (d, 1H), 7.07 (t, 1H), 7.23 (m, 1H), 7.44 (m, 2H), 7.51 (t, 1H), 7.68 (m, 2H), 8.22 (t, 2H), 8.32 (d, 1H), 8.36 (d, 1H), 8.50 (d, 1H), 8.63 (m, 2H), 8.69 (d, 1H), 8.75 (s, 1H).

[ Synthetic example  87: compound 15- (3- bromophenyl ) -15H- phenanthro [Synthesis of 9,10-a] carbazole]

15H-phenanthro [9,10-a] carbazole 26.91 g (84.78 mmol), 1,3-dibromobenzene 30 g (127.17 mmol), Cu powder 0.54 g (8.48 mmol), K ₂ CO ₃ 11.72 g (84.78 mmol), 12.04 g (84.78 mmol) of Na ₂ SO ₄ and 300 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (3-bromophenyl) -15H-phenanthro [9,10-a] carbazole as a target compound. 14.02 g (35% yield) were obtained.

¹ H NMR: 6.43 (d, 1H), 6.96 (t, 1H), 7.13 (t, 1H), 7.25 (d, 1H), 7.46 (m, 2H), 7.58 (t, 1H), 7.71 (m, 2H), 8.24 (d, 1H), 8.37 (m, 3H), 8.44 (s, 1H), 8.53 (d, 1H), 8.65 (m, 2H), 8.75 (d, 1H).

[ Synthetic example  88: compound 15- (4- bromophenyl ) -15H- phenanthro [Synthesis of 9,10-a] carbazole]

15H-phenanthro [9,10-a] carbazole 26.91 g (84.78 mmol), 1,4-dibromobenzene 30 g (127.17 mmol), Cu powder 0.54 g (8.48 mmol), K ₂ CO ₃ 11.72 g (84.78 mmol), 12.04 g (84.78 mmol) of Na ₂ SO ₄ and 300 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (4-bromophenyl) -15H-phenanthro [9,10-a] carbazole as a target compound. 12.82 g (yield 32%) were obtained.

¹ H NMR: 6.40 (d, 1H), 7.05 (t, 1H), 7.24 (m, 1H), 7.43 (m, 2H), 7.55 (t, 1H), 7.69 (m, 2H), 8.21 (t, 2H), 8.30 (d, 1H), 8.37 (d, 1H), 8.42 (d, 1H), 8.53 (d, 1H), 8.66 (m, 2H), 8.68 (d, 1H), 8.70 (d, 1H ).

[ Synthetic example  89: compound 15- (3,5- dibromophenyl ) -15H- phenanthro [9,10-a] Synthesis of carbazole]

15H-phenanthro [9,10-a] carbazole 26.16 g (63.53 mmol), 1,3,5-tribromo benzene 30 g (95.31 mmol), Cu powder 0.4 g (6.35 mmol), K ₂ CO ₃ 8.78 g (63.53 mmol), 9.02 g (63.53 mmol) of Na ₂ SO ₄ , and 300 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (3,5-dibromophenyl) -15H-phenanthro [9, 16.11 g (yield 46%) of 10-a] carbazole was obtained.

¹ H NMR: 6.53 (d, 1H), 6.72 (t, 1H), 7.15 (t, 1H), 7.26 (d, 1H), 7.45 (m, 2H), 7.59 (t, 1H), 7.73 (m, 2H), 8.25 (d, 1H), 8.33 (m, 3H), 8.41 (s, 1H), 8.55 (d, 1H), 8.64 (s, 1H), 8.80 (d, 1H).

[ Synthetic example  90: compound 15- (2- chloropyrimidin -5- yl ) -15H- phenanthro [9,10-a] Synthesis of carbazole]

21.88 g (68.93 mmol) of 15H-phenanthro [9,10-a] carbazole, 20 g (103.40 mmol) of 5-bromo-2-chloropyrimidine, 0.4 g (6.89 mmol) of Cu powder, 8.78 g (68.93 mmol) of K ₂ CO ₃ ), Na ₂ SO ₄ 9.02 g (68.93 mmol), and 250 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (2-chloropyrimidin-5-yl) -15H-phenanthro [9. , 10-a] carbazole 10.08 g (yield 34%) was obtained.

¹ H NMR: 6.44 (d, 1H), 7.07 (t, 1H), 7.21 (m, 1H), 7.40 (m, 2H), 7.52 (t, 1H), 7.66 (m, 2H), 8.23 (t, 2H), 8.29 (d, 1H), 8.35 (d, 1H), 8.47 (d, 1H), 8.63 (s, 1H), 8.67 (s, 1H), 8.72 (d, 1H).

[ Synthetic example  91: compound 15- (4,6- dichloropyridin -2- yl ) -15H- phenanthro [9,10-a] carbazole Synthesis of

Synthesis Example 4 was prepared using 0.98 g (41.11 mmol) of NaH, 5.22 g (16.44 mmol) of 15H-phenanthro [9,10-a] carbazole, 6 g (32.89 mmol) of 2,4,6-trichloropyridine, and 200 ml of DMF. In the same manner, 2.36 g (yield 31%) of 15- (4,6-dichloropyridin-2-yl) -15H-phenanthro [9,10-a] carbazole was obtained as a target compound.

¹ H NMR: 6.52 (d, 1H), 6.71 (t, 1H), 7.13 (t, 1H), 7.29 (d, 1H), 7.46 (m, 2H), 7.60 (t, 1H), 7.75 (m, 2H), 8.27 (d, 1H), 8.38 (m, 3H), 8.43 (s, 1H), 8.59 (d, 1H), 8.77 (d, 1H).

[ Synthetic example  92 compound 15- (4- chloropyrimidin -2- yl ) -15H- phenanthro [9,10-a] Synthesis of carbazole]

Same method as Synthesis Example 4 using 4.03 g (167.81 mmol) of NaH, 21.30 g (67.12 mmol) of 15H-phenanthro [9,10-a] carbazole, 20 g (134.25 mmol) of 2,4-dichloropyrimidine, and 300 ml of DMF As a target compound, 2.36 g (yield 31%) of 15- (4-chloropyrimidin-2-yl) -15H-phenanthro [9,10-a] carbazole was obtained.

¹ H NMR: 6.43 (d, 1H), 6.95 (t, 1H), 7.12 (t, 1H), 7.26 (d, 1H), 7.48 (m, 2H), 7.58 (t, 1H), 7.79 (m, 2H), 8.27 (d, 1H), 8.40 (m, 2H), 8.53 (d, 1H), 8.69 (d, 1H), 8.76 (d, 1H).

[ Synthetic example  93: Compound Inv5 Synthesis of -1 Example  66

15- (6-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), phenylboronic acid 1.55 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol %), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis example 1 to obtain 3.88 g (yield 78%) of the target compound Inv5-1.

GC-Mass (Theoretical value: 470.18 g / mol, Measured value: 470 g / mol)

[ Synthetic example  94: Compound Inv5 Synthesis of -2 Example  67

15- (4,6-dichloropyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.79 mmol), phenylboronic acid 1.58 g (12.95 mmol), Pd (PPh ₃ ) ₄ 0.62 g ( 5 mol%), NaOH 1.29 g (34.89 mmol), and THF / distilled water (100ml / 50ml) were used in the same manner as in Synthesis Example 1 to obtain 3.83 g (yield 65%) of the title compound Inv5-2. .

GC-Mass (Theoretical value: 546.21 g / mol, Measured value: 546 g / mol)

[ Synthetic example  95: Compound Inv5 Synthesis of -4 Example  68

Synthesis Example using 0.79 g (32.93 mmol) of NaH, 4.18 g (13.17 mmol) of 15H-phenanthro [9,10-a] carbazole, 7 g (26.34 mmol) of 4-chloro-2,6-diphenylpyridine, and 100 ml of DMF In the same manner as in 4, 3.02 g (yield 42%) of the title compound Inv5-4 was obtained.

GC-Mass (Theoretical value: 546.21 g / mol, Measured value: 546 g / mol)

[ Synthetic example  96: Compound Inv5 Synthesis of -5 Example  69

15- (4-chloropyrimidin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (11.63 mmol), phenylboronic acid 1.70 g (13.96 mmol), Pd (PPh ₃ ) ₄ 0.67 g (5 mol %), NaOH 1.40 g (34.89 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis example 1 to obtain 3.89 g (yield 71%) of Inv5-5 as a target compound.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthetic example  97: compound Inv5 Synthesis of -6 Example  70

Synthesis Example using 0.79 g (32.81 mmol) of NaH, 4.16 g (13.12 mmol) of 15H-phenanthro [9,10-a] carbazole, 7 g (26.25 mmol) of 2-chloro-4,6-diphenylpyrimidine, and 100 ml of DMF 2.80 g (yield 39%) of the target compound, Inv5-6, was obtained in the same manner as in Example 4.

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

[ Synthetic example  98: compound Inv5 Synthesis of -16 Example  71

15- (4-bromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), 4,6-diphenylpyrimidin-2-ylboronic acid 3.51 g (12.70 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 4.56 g (yield 69%) of the title compound Inv5-16. Obtained.

GC-Mass (Theoretical value: 623.24 g / mol, Measured value: 623 g / mol)

[ Synthetic example  99: compound Inv5 Synthesis of -21 Example  72

NaH 0.79 g (32.69 mmol), 15H-phenanthro [9,10-a] carbazole 4.15 g (13.07 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 7 g (26.15 mmol), And using 100 ml of DMF to obtain 2.87 g (yield 40%) of the target compound Inv5-21 in the same manner as in Synthesis example 4.

GC-Mass (Theoretical value: 548.21 g / mol, Measured value: 548 g / mol)

[ Synthetic example  100: compound Inv5 Synthesis of -22 Example  73

15- (4-bromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid 3.52 g (12.70 mmol) , Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100 ml / 50 ml) were tested in the same manner as in Synthesis Example 1 to obtain the target compound Inv5-22. 3.90 g (59% yield) were obtained.

GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol)

[ Synthetic example  101: compound Inv5 Synthesis of -24 Example  74

15- (6-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), pyridin-3-ylboronic acid 1.56 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 In the same manner as in Synthesis Example 1 using g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100ml / 50ml) to obtain the title compound Inv 3.54 g (71% yield). .

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthetic example  102: Compound Inv5 Synthesis of -29 Example  75

NaH 0.78 g (32.45 mmol), 15H-phenanthro [9,10-a] carbazole 4.12 g (12.98 mmol), 2-chloro-4,6-di (pyridin-3-yl) -1,3,5-triazine 7 g (25.96 mmol) and 100 ml of DMF were used to obtain 2.64 g (yield 37%) of the title compound Inv5-29 (yield 37%) in the same manner as in Synthesis example 4.

GC-Mass (Theoretical value: 550.19 g / mol, Measured value: 550 g / mol)

[ Synthetic example  103: Compound Inv5 Synthesis of -48 Example  76

15- (2-chloropyrimidin-5-yl) -15H-phenanthro [9,10-a] carbazole 5 g (11.63 mmol), pyridin-3-ylboronic acid 1.72 g (13.96 mmol), Pd (PPh ₃ ) ₄ 0.67 g (5 mol%), NaOH 1.40 g (34.89 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 3.96 g (72% yield) of the target compound, Inv5-48. Obtained.

GC-Mass (Theoretical value: 472.17 g / mol, Measured value: 472 g / mol)

[ Synthetic example  104: Compound Inv5 Synthesis of -52] Example  77

15H-phenanthro [9,10-a] carbazole 2.81 g (8.86 mmol), 4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole 5 g (13.29 mmol), Cu powder 0.06 g (0.89 mmol), 1.22 g (8.86 mmol) of K ₂ CO ₃ , 1.26 g (8.86 mmol) of Na ₂ SO ₄ , and 100 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain Inv5 as a target compound. 2.5 g (46% yield) of -52 were obtained.

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

[ Synthetic example  105: compound Inv5 Synthesis of -63]- Example  78

15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), phenylboronic acid 1.55 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol %), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis example 1 to obtain 3.68 g (yield 74%) of the title compound Inv5-63.

GC-Mass (Theoretical value: 470.18 g / mol, Measured value: 470 g / mol)

[ Synthetic example  106: Compound Inv5 Synthesis of -131 Example  79

15- (6-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), pyridin-4-ylboronic acid 1.56 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 3.34 g (yield 67%) of the Inv compound. .

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthetic example  107: Compound Inv5 Synthesis of -135] Example  80

15- (3-bromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), pyridin-3-ylboronic acid 1.56 g (12.70 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol %), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis example 1 to obtain 3.84 g (yield 77%) of the title compound Inv5-135.

GC-Mass (Theoretical value: 470.18 g / mol, Measured value: 470 g / mol)

[ Synthetic example  108: compound Inv5 Synthesis of -144 Example  81

15- (4,6-dichloropyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.79 mmol), pyridin-3-ylboronic acid 1.59 g (12.695 mmol), Pd (PPh ₃ ) ₄ 0.62 g (5 mol%), NaOH 1.29 g (32.37 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 3.85 g of the target compound, Inv5-144 (yield 65%). ) Was obtained.

GC-Mass (Theoretical value: 548.20 g / mol, Measured value: 548 g / mol)

[ Synthetic example  109: compound Inv5 Synthesis of -145]- Example  82

NaH 0.78 g (32.69 mmol), 15H-phenanthro [9,10-a] carbazole 4.15 g (13.07 mmol), 2-chloro-4,6-di (pyridin-3-yl) -1,3,5-triazine 7 g (26.15 mmol) and 100 mL of DMF were used to obtain 2.8 g (yield 39%) of the title compound Inv5-145 (yield 39%) in the same manner as in Synthesis example 4.

GC-Mass (Theoretical value: 548.20 g / mol, Measured value: 548 g / mol)

[ Synthetic example  110: compound Inv5 Synthesis of -147]- Example  83

15- (3-bromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), imidazo [1,2-a] pyridin-2-ylboronic acid 2.06 g (12.70 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 3.29 g (yield of the target compound) 61%) was obtained.

GC-Mass (Theoretical value: 509.19 g / mol, Measured value: 509 g / mol)

[ Synthetic example  111: Compound Inv5 Synthesis of -150 Example  84

15- (4-chloropyrimidin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (11.63 mmol), pyridin-3-ylboronic acid 1.72 g (13.96 mmol), Pd (PPh ₃ ) ₄ 0.67 g (5 mol%), NaOH 1.40 g (34.89 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 2.96 g (54% yield) of the target compound, Inv5-150. Obtained.

GC-Mass (Theoretical value: 472.17 g / mol, Measured value: 472 g / mol)

[ Synthetic example  112: compound Inv5 Synthesis of -151]- Example  85

15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), pyridin-4-ylboronic acid 1.55 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 3.34 g (yield 67%) of the target compound, Inv5-151. Obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthetic example  113: Compound Inv5 Synthesis of -152] Example  86

15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), pyridin-3-ylboronic acid 1.56 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100ml / 50ml) were used in the same manner as in Synthesis Example 1 to obtain 3.39 g (yield 68%) of the target compound, Inv5-152. Obtained.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthetic example  114: Compound Inv5 Synthesis of -153 Example  87

15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid 3.51 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100 ml / 50 ml) were tested in the same manner as in Synthesis Example 1 3.64 g (yield 55%) of Phosphorus Inv5-153 was obtained.

GC-Mass (Theoretical value: 625.23 g / mol, Measured value: 625 g / mol)

[ Synthetic example  115: Compound Inv5 Synthesis of -154]- Example  88

15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), 4,6-di (pyridin-3-yl) -1,3,5-triazin -2-ylboronic acid 3.54 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100ml / 50ml) The experiment was carried out in the same manner to obtain 3.38 g (yield 51%) of the title compound, Inv5-154.

GC-Mass (Theoretical value: 627.22 g / mol, Measured value: 627 g / mol)

[ Synthetic example  116: Compound Inv5 Synthesis of -155]- Example  89

15- (5-bromopyridin-2-yl) -15H-phenanthro [9,10-a] carbazole 5 g (10.56 mmol), 4,6-diphenylpyrimidin-2-ylboronic acid 3.50 g (12.68 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.69 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 3.50 g (yield of the target compound) 53%) was obtained.

GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol)

[ Synthetic example  117: Compound Inv5 Synthesis of -156] Example  90

15- (2-chloropyrimidin-5-yl) -15H-phenanthro [9,10-a] carbazole 5 g (11.63 mmol), pyridin-4-ylboronic acid 1.72 g (13.96 mmol), Pd (PPh ₃ ) ₄ 0.67 g (5 mol%), NaOH 1.40 g (34.89 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 3.74 g (yield 68%) of the target compound, Inv5-156. Obtained.

GC-Mass (Theoretical value: 472.17 g / mol, Measured value: 472 g / mol)

[ Synthetic example  118: Compound Inv5 Synthesis of -157 Example  91

15- (2-chloropyrimidin-5-yl) -15H-phenanthro [9,10-a] carbazole 5 g (11.63 mmol), phenylboronic acid 1.70 g (13.96 mmol), Pd (PPh ₃ ) ₄ 0.67 g (5 mol %), NaOH 1.40 g (34.89 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis example 1 to obtain 2.91 g (yield 53%) of the title compound Inv5-157.

GC-Mass (Theoretical value: 471.17 g / mol, Measured value: 471 g / mol)

[ Synthetic example  119: Compound Inv5 Synthesis of -158] Example  92

15- (3,5-dibromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (9.07 mmol), pyridin-3-ylboronic acid 1.34 g (10.88 mmol), Pd (PPh ₃ ) ₄ 0.52 g ( 5 mol%), NaOH 1.09 g (27.21 mmol), and THF / distilled water (100ml / 50ml) were used in the same manner as in Synthesis Example 1 to obtain 3.63 g (yield 73%) of the title compound Inv5-158. .

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

[ Synthetic example  120: compound Inv5 Synthesis of -159]- Example  93

8.11 g (17.16 mmol) of 15- (3-bromophenyl) -15H-phenanthro [9,10-a] carbazole, 5 g (25.74 mmol) of 2-phenyl-1H-benzo [d] imidazole, 0.11 g of Cu powder mmol), 2.37 g (17.16 mmol) of K ₂ CO ₃ , 2.44 g (17.16 mmol) of Na ₂ SO ₄ , and 100 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85, and 4.12 g of the target compound, Inv5-159. (Yield 41%) was obtained.

GC-Mass (Theoretical value: 585.17 g / mol, Measured value: 585 g / mol)

[ Synthetic example  121: Compound Inv5 Synthesis of -160]- Example  94

15- (3-bromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), dibenzo [b, d] thiophen-4-ylboronic acid 2.90 g (12.70 mmol), Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain 4.69 g of the target compound, Inv5-160 (yield 77%). ) Was obtained.

GC-Mass (calculated: 575.17 g / mol, measured: 575 g / mol)

[ Synthetic example  122: compound Inv5 Synthesis of -161]- Example  95

15 H-phenanthro [9,10-a] carbazole 3.08 g (16.02 mmol), 3-bromoquinoline 5 g (24.03 mmol), Cu powder 0.10 g (1.60 mmol), K ₂ CO ₃ 2.21 g (16.02 mmol), Na ₂ Experiment with the same method as in Synthesis Example 85 using 2.28 g (16.02 mmol) of SO ₄ and 100 ml of nitrobenzene to obtain 3.7 g (yield 52%) of the title compound Inv5-161.

GC-Mass (Theoretical value: 444.16 g / mol, Measured value: 444 g / mol)

[ Synthetic example  123: compound Inv5 Synthesis of -162]- Example  96

15H-phenanthro [9,10-a] carbazole 3.54 g (11.14 mmol), 2- (4-bromophenyl) -5-phenylfuran 5 g (16.71 mmol), Cu powder 0.07 g (1.60 mmol), K ₂ CO ₃ 1.54 g (11.14 mmol), 1.58 g (11.14 mmol) of Na ₂ SO ₄ , and 100 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 2.75 g (yield 46%) of the title compound Inv5-162. .

GC-Mass (Theoretical value: 535.19 g / mol, Measured value: 535 g / mol)

[ Synthetic example  124: Compound Inv5 Synthesis of -163 Example  97

15- (3-bromophenyl) -15H-phenanthro [9,10-a] carbazole 9.42 g (19.94 mmol), 9H-carbazole 5 g (29.90 mmol), Cu powder 0.13 g (1.99 mmol), K ₂ CO ₃ 2.76 In the same manner as in Synthesis Example 85 using g (19.94 mmol), 2.83 g (19.94 mmol) of Na ₂ SO ₄ , and 100 ml of nitrobenzene, 4.79 g (yield 43%) of Inv5-163 was obtained. .

GC-Mass (Theoretical value: 558.21 g / mol, Measured value: 558 g / mol)

[ Synthetic example  125: compound 13- bromo -15- phenyl -15H- phenanthro [Synthesis of 9,10-a] carbazole]

13-bromo-15H-phenanthro [9,10-a] carbazole 12.95 g (32.68 mmol), iodobenzene 10 g (49.02 mmol), Cu powder 0.21 g (3.27 mmol), K ₂ CO ₃ 4.52 g (32.68 mmol), 4.64 g (32.68 mmol) of Na ₂ SO ₄ and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 13-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole as a target compound. 10.03 g (65% yield) were obtained.

GC-Mass (Theoretical value: 471.06 g / mol, Measured value: 471 g / mol)

[ Synthetic example  126 compound 12- bromo -15- phenyl -15H- phenanthro [Synthesis of 9,10-a] carbazole]

12.bromo-15H-phenanthro [9,10-a] carbazole 12.95 g (32.68 mmol), iodobenzene 10 g (49.02 mmol), Cu powder 0.21 g (3.27 mmol), K ₂ CO ₃ 4.52 g (32.68 mmol), 4.64 g (32.68 mmol) of Na ₂ SO ₄ and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 13-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole as a target compound. 9.42 g (61% yield) were obtained.

GC-Mass (Theoretical value: 471.06 g / mol, Measured value: 471 g / mol)

[ Synthetic example  127 compound 6- bromo -15- phenyl -15H- phenanthro [Synthesis of 9,10-a] carbazole]

6-bromo-15H-phenanthro [9,10-a] carbazole 12.95 g (32.68 mmol), iodobenzene 10 g (49.02 mmol), Cu powder 0.21 g (3.27 mmol), K ₂ CO ₃ 4.52 g (32.68 mmol), 4.64 g (32.68 mmol) of Na ₂ SO ₄ and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 13-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole as a target compound. 9.11 g (yield 59%) were obtained.

GC-Mass (Theoretical value: 471.06 g / mol, Measured value: 471 g / mol)

[ Synthetic example  128: compound 15- ( biphenyl -4- yl ) -13- bromo -15H- phenanthro [9,10-a] Synthesis of carbazole]

13-bromo-15H-phenanthro [9,10-a] carbazole 9.43 g (23.80 mmol), 4-iodobiphenyl 10 g (35.70 mmol), Cu powder 0.15 g (2.38 mmol), K ₂ CO ₃ 3.29 g (23.80 mmol ), Na ₂ SO ₄ 3.38 g (23.80 mmol), and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (biphenyl-4-yl) -13-bromo-15H-phenanthro as a target compound. 7.18 g (yield 55%) of [9,10-a] carbazole were obtained.

GC-Mass (Theoretical value: 547.09 g / mol, Measured value: 547 g / mol)

[ Synthetic example  129: compound 15- ( biphenyl -4- yl ) -6- bromo -15H- phenanthro [Synthesis of 9,10-a] carbazole]

9.43 g (23.80 mmol) of 6-bromo-15H-phenanthro [9,10-a] carbazole, 10 g (35.70 mmol) of 4-iodobiphenyl, 0.15 g (2.38 mmol) of Cu powder, 3.29 g (23.80 mmol) of K ₂ CO ₃ ), Na ₂ SO ₄ 3.38 g (23.80 mmol), and 200 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 15- (biphenyl-4-yl) -6-bromo-15H-phenanthro as a target compound. 6.66 g (51% yield) of [9,10-a] carbazole were obtained.

GC-Mass (Theoretical value: 547.09 g / mol, Measured value: 547 g / mol)

[ Synthetic example  130: Compound Inv6 Synthesis of -271]- Example  98

12-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), 2,3'-bipyridin-6-ylboronic acid 2.54 g (12.70 mmol), Pd (PPh ₃ ) ₄ In the same manner as in Synthesis Example 1 using 0.61 g (5 mol%), 1.27 g (31.75 mmol) of NaOH, and THF / distilled water (100 ml / 50 ml), 4.11 g of the target compound, Inv6-271 (yield 71%) Obtained.

GC-Mass (Theoretical value: 547.20 g / mol, Measured value: 547 g / mol)

[ Synthetic example  131: Compound Inv6 Synthesis of -272] Example  99

13-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), 4,6-diphenyl-1,3,5-triazin-2-ylboronic acid 3.52 g (12.70 mmol) , Pd (PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100 ml / 50 ml) were tested in the same manner as in Synthesis Example 1 to obtain the target compound Inv6-272. 3.77 g (yield 57%) were obtained.

GC-Mass (Theoretical value: 624.23 g / mol, Measured value: 624 g / mol)

[ Synthetic example  132: Compound Inv6 Synthesis of -273 Example  100

6-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), 5-phenylpyridin-2-ylboronic acid 2.53 g (12.70 mmol), Pd (PPh ₃ ) ₄ 0.61 g ( 5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100ml / 50ml) were used in the same manner as in Synthesis Example 1 to obtain 3.82 g (yield 66%) of the title compound Inv6-273. .

GC-Mass (Theoretical value: 546.21 g / mol, Measured value: 546 g / mol)

[ Synthetic example  133: Compound Inv6 Synthesis of -274] Example  101

15- (biphenyl-4-yl) -6-bromo-15H-phenanthro [9,10-a] carbazole 5 g (9.12 mmol), 4-phenylpyrimidin-2-ylboronic acid 2.19 g (10.94 mmol), Pd (PPh ₃ ) ₄ 0.53 g (5 mol%), NaOH 1.09 g (27.35 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 3.13 g (yield of the target compound) 55%).

GC-Mass (Theoretical value: 623.23 g / mol, Measured value: 623 g / mol)

[ Synthetic example  134: Compound Inv7 Synthesis of -3 Example  102

12-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 5.03 g (10.64 mmol), N-phenylnaphthalen-1-amine 3.5 g (15.96 mmol), Cu powder 0.07 g (1.06 mmol), K _{In the} same manner as in Synthesis Example 85 using 1.47 g (10.64 mmol) of ₂ CO ₃ , 1.51 g (10.64 mmol) of Na ₂ SO ₄ , and 100 ml of nitrobenzene, the desired compound Inv7-3 4.42 g (yield 68%) ) Was obtained.

GC-Mass (Theoretical value: 610.24 g / mol, Measured value: 610 g / mol)

[ Synthetic example  135: Compound Inv7 Synthesis of -80]- Example  103

6-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 4.90 g (10.37 mmol), dibiphenyl-4-ylamine 5 g (15.56 mmol), Cu powder 0.07 g (1.04 mmol), K ₂ CO ₃ 1.43 g (10.37 mmol), 1.47 g (10.37 mmol) of Na ₂ SO ₄ , and 100 ml of nitrobenzene were used in the same manner as in Synthesis Example 85 to obtain 4.07 g (yield 55%) of the target compound Inv7-80. Obtained.

GC-Mass (Theoretical value: 712.29 g / mol, Measured value: 712 g / mol)

[ Synthetic example  136: Compound Inv7 Synthesis of -85]- Example  104

15- (4-bromophenyl) -15H-phenanthro [9,10-a] carbazole 5 g (10.58 mmol), 4- (naphthalen-1-yl (phenyl) amino) phenylboronic acid 4.31 g (12.70 mmol), Pd ( PPh ₃ ) ₄ 0.61 g (5 mol%), NaOH 1.27 g (31.75 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 5.60 g ( Yield 77%).

GC-Mass (Theoretical value: 686.27 g / mol, Measured value: 686 g / mol)

[ Synthetic example  137: compound Inv7 Synthesis of -86]- Example  105

15- (4-bromophenyl) -15H-phenanthro [9,10-a] carbazole 4.90 g (10.37 mmol), dibiphenyl-4-ylamine 5 g (15.56 mmol), Cu powder 0.07 g (1.04 mmol), K ₂ CO ₃ 1.43 g (10.37 mmol), Na ₂ SO ₄ 1.47 g (10.37 mmol), and 100 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85 to obtain 3.62 g (yield 49%) of the target compound Inv7-86. Obtained.

GC-Mass (Theoretical value: 712.29 g / mol, Measured value: 712 g / mol)

[ Synthetic example  138: Compound Inv7 Synthesis of -87 Example  106

15- (biphenyl-4-yl) -13-bromo-15H-phenanthro [9,10-a] carbazole 3 g (5.47 mmol), 4- (dibiphenyl-4-ylamino) phenylboronic acid 2.90 g (6.56 mmol), 0.35 g (5 mol%) of Pd (PPh ₃ ) ₄ , 0.66 g (16.41 mmol) of NaOH, and THF / distilled water (100 ml / 50 ml) were used in the same manner as in Synthesis Example 1 to obtain Inv7-87 3.55. g (yield 75%) was obtained.

GC-Mass (Theoretical value: 864.35 g / mol, Measured value: 864 g / mol)

[ Synthetic example  139: Compound Inv7 Synthesis of -88 Example  107

15- (biphenyl-4-yl) -6-bromo-15H-phenanthro [9,10-a] carbazole 5 g (9.12 mmol), N-phenylnaphthalen-1-amine 3 g (13.68 mmol), Cu powder 0.06 g (0.91 mmol), K ₂ CO ₃ 1.26 g (9.12 mmol), Na ₂ SO ₄ 1.30 g (9.12 mmol), and 100 ml of nitrobenzene were tested in the same manner as in Synthesis Example 85, and the target compound Inv7-88 was obtained. 2.69 g (yield 43%) were obtained.

GC-Mass (Theoretical value: 686.27 g / mol, Measured value: 686 g / mol)

[ Synthetic example  140: compound Inv8 Synthesis of -19 Example  108

12-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 3 g (6.35 mmol), 4- (biphenyl-4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino ) phenylboronic acid 3.67 g (7.62 mmol), Pd (PPh ₃ ) ₄ 0.37 g (5 mol%), NaOH 0.76 g (19.05 mmol), and THF / distilled water (100ml / 50ml) the same method as in Synthesis Example 1 In order to obtain 3.63 g (yield 69%) of the title compound Inv8-19.

GC-Mass (Theoretical value: 828.35 g / mol, Measured value: 828 g / mol)

[ Synthetic example  141: Compound Inv8 Synthesis of -100 Example  109

6-bromo-15-phenyl-15H-phenanthro [9,10-a] carbazole 3 g (6.35 mmol), 4- (naphthalen-1-yl (phenyl) amino) phenylboronic acid 2.59 g (7.62 mmol), Pd ( PPh ₃ ) ₄ 0.37 g (5 mol%), NaOH 0.76 g (19.05 mmol), and THF / distilled water (100ml / 50ml) was tested in the same manner as in Synthesis Example 1 3.18 g ( Yield 73%) was obtained.

GC-Mass (Theoretical value: 686.27 g / mol, Measured value: 686 g / mol)

[ Example  1-57 and 66-101] organic EL  Device Fabrication and Evaluation

An organic EL device was prepared in the following manner.

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the washing of distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

(40 nm) / Inv compound + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (10 nm) using the compounds of the present invention as a host on the ITO 1 nm) / Al, and then their luminescent characteristics were evaluated. The results are shown in Table 1 below. Here, the compounds to be applied to the host are shown in Table 1 below.

[ Comparative example  One]

On the electrode prepared in the same manner as in the above embodiment, the light emitting device was NPB (40 nm) / CBP + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (1 nm) / Al. After the configuration, the light emission characteristics were evaluated in the same manner as in Examples 1 to 57.

For reference, the structures of NPB, CBP and Ir (ppy) ₃ and BCP are as follows.

NPB

CBP

Ir ( ppy 3

BCP

As a result, the organic light emitting devices of Examples 1 to 57 and 66 to 101 using the triphenylene-based compound of the present invention exhibited better performance in terms of voltage and efficiency than the organic EL device of Comparative Example 1 using the conventional CBP. I could confirm that.

[ Example  58 ~ 65 & 102 ~ 109] Organic EL  Device Fabrication and Evaluation

An organic EL device was prepared in the following manner.

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the washing of distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

(Invol) / CBP + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (1 nm) using the compounds of the present invention as the hole transport layer on the ITO / Al, and their luminescent properties were evaluated. The results are shown in Table 2 below. Here, the compound to be used as the hole transporting layer is shown in Table 2 below.

[ Comparative example  2]

(40 nm) / CBP + 10% Ir (ppy) ₃ (20 nm) / BCP (10 nm) / Alq ₃ (40 nm) / LiF (1 nm) / Al on the electrode prepared in the same manner as in the above- , And then the luminescent characteristics were evaluated in the same manner as in Example 1. [

As a result of the experiment, the organic light emitting diodes of Examples 58 to 65 and 102 to 109 using the triphenylene-based compound according to the present invention had superior performance in terms of voltage and efficiency in comparison with the organic EL device of the Comparative Example using conventional NPB. It was confirmed that it was shown. Therefore, it was found that the triphenylene-based compounds of the present application including the tertiary amine group exhibit excellent performance in the hole transport material.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.

Claims (10)

A material for an organic electroluminescent device represented by Formula 1 or Formula 2 below:
[Formula 1]

(2)

In the above formulas,
X and Y are NR ₁₅ or a single bond, where one of X and Y is NR ₁₅ , and the other is a single bond (m or n is 0),
R ₁ to R ₁₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group each other, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkylamino group, C ₅ to C ₄₀ arylamino group, C ₅ to C ₄₀ diarylamino group, C ₅ to C ₄₀ heteroarylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ aryl An alkyl group, a C ₆ to C ₄₀ heteroarylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₁ to C ₄₀ halogenalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₃ to C ₄₀ alkylsilyl group, C ₃ ~ C ₄₀ aryl silyl group, and a C ₃ ~ is selected from the heteroaryl group consisting of a silyl group of C _40,
Wherein R ₁ to R ₁₅ may each be fused to an adjacent substituent or form a ring;
m and n are 0 or 1, respectively. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3:
(3)

In the above formula, R ₁ to R ₁₅ are the same as defined in claim 1. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by Chemical Formula 4.
[Chemical Formula 4]

In the above formulas,
L is a direct link; Or C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₅ to C ₄₀ aryl group, C ₁ to C ₄₀ heteroaryl group, C ₁ to C ₄₀ alkoxy groups, C ₅ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkylamino groups, C ₅ to C ₄₀ arylamino groups, C ₅ to C ₄₀ diarylamino groups, C ₅ to C ₄₀ heteros Arylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ arylalkyl group, C ₆ to C ₄₀ heteroarylalkyl group, C ₃ to C ₄₀ cycloalkyl group, C ₁ to C ₄₀ halogenalkyl group , C ₃ ~ C ₄₀ heterocycloalkyl group, is selected from the group consisting of C ₃ ~ C ₄₀ alkyl silyl group, C ₃ ~ C ₄₀ aryl silyl group, C ₃ ~ group heteroaryl silyl of the C ₄₀ of the adjacent group and ring Can form
R ₁₆ and R ₁₇ are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group each other, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkylamino group, C ₅ to C ₄₀ arylamino group, C ₅ to C ₄₀ diarylamino group, C ₅ to C ₄₀ heteroarylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ aryl An alkyl group, a C ₆ to C ₄₀ heteroarylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₁ to C ₄₀ halogenalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₃ to C ₄₀ alkylsilyl group, An arylsilyl group of C ₃ to C ₄₀ , and a heteroarylsilyl group of C ₃ to C ₄₀ , which may form a ring with an adjacent group,
R ₁ to R ₁₀ , R ₁₅ are the same as defined in claim 1. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by Chemical Formula 5.
[Chemical Formula 5]

In the above formulas,
Ar ₁ , R ₁₈ to R ₂₁ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alky group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ alkoxy group of C _40, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyl group, C ₅ to C ₄₀ arylamino group, C ₅ to C ₄₀ diarylamino group, C ₅ to C ₄₀ heteroarylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ arylalkyl group, C ₆ ~ C ₄₀ heteroaryl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₁ ~ C ₄₀ halogen group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₃ ~ C of the _An arylsilyl group of ₄₀ , a heteroarylsilyl group of C ₃ to C ₄₀ , except that Ar ₁ is hydrogen, which may form a ring with an adjacent group;
R ₁ to R ₁₀ , R ₁₅ are the same as defined in claim 1. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 2 is represented by Chemical Formula 6.
[Chemical Formula 6]

In the above formula, R ₁ to R ₁₅ are the same as defined in claim 1. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 2 is represented by Chemical Formula 7.
(7)

In the above formulas,
L is a direct link; Or C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₅ to C ₄₀ aryl group, C ₁ to C ₄₀ heteroaryl group, C ₁ to C ₄₀ alkoxy groups, C ₅ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkylamino groups, C ₅ to C ₄₀ arylamino groups, C ₅ to C ₄₀ diarylamino groups, C ₅ to C ₄₀ heteros Arylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ arylalkyl group, C ₆ to C ₄₀ heteroarylalkyl group, C ₃ to C ₄₀ cycloalkyl group, C ₁ to C ₄₀ halogenalkyl group , C ₃ ~ C ₄₀ heterocycloalkyl group, is selected from the group consisting of C ₃ ~ C ₄₀ alkyl silyl group, C ₃ ~ C ₄₀ aryl silyl group, C ₃ ~ group heteroaryl silyl of the C ₄₀ of the adjacent group and ring Can form
R ₁₆ and R ₁₇ are the same or different, each independently represent hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group each other, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ C ₄₀ alkoxy group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkylamino group, C ₅ to C ₄₀ arylamino group, C ₅ to C ₄₀ diarylamino group, C ₅ to C ₄₀ heteroarylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ aryl An alkyl group, a C ₆ to C ₄₀ heteroarylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₁ to C ₄₀ halogenalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₃ to C ₄₀ alkylsilyl group, An arylsilyl group of C ₃ to C ₄₀ , and a heteroarylsilyl group of C ₃ to C ₄₀ , which may form a ring with an adjacent group,
R ₁ to R ₁₀ , R ₁₅ are the same as defined in claim 1. The organic electroluminescent device material according to claim 1, wherein the compound represented by Chemical Formula 2 is represented by the following Chemical Formula 8.
[Chemical Formula 8]

In the above formulas,
Ar ₁ , R ₁₈ to R ₂₁ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alky group, C ₅ ~ C ₄₀ aryl group, C ₁ ~ C ₄₀ heteroaryl group, C ₁ ~ alkoxy group of C _40, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyl group, C ₅ to C ₄₀ arylamino group, C ₅ to C ₄₀ diarylamino group, C ₅ to C ₄₀ heteroarylamino group, C ₂ to C ₄₀ diheteroarylamino group, C ₆ to C ₄₀ arylalkyl group, C ₆ ~ C ₄₀ heteroaryl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₁ ~ C ₄₀ halogen group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₃ ~ C of the _An arylsilyl group of ₄₀ , a heteroarylsilyl group of C ₃ to C ₄₀ , except that Ar ₁ is hydrogen, which may form a ring with an adjacent group;
R ₁ to R ₁₀ , R ₁₅ are the same as defined in claim 1. An organic electroluminescent device comprising: (i) a cathode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 7, characterized in that the organic electroluminescent device. The organic light emitting device of claim 8, wherein the organic material layer is selected from a group consisting of a light emitting layer, a hole injection layer, and a hole transport layer. The organic electroluminescent device according to claim 8, wherein the organic layer including the compound is a phosphorescent host or a fluorescent host material of the light emitting layer.

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