[ CAS No. 502161-03-7 ] {[proInfo.proName]}

Name: 502161-03-7|3-Iodo-N-phenylcarbazole|98%
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Quality Control of [ 502161-03-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 502161-03-7 ]

SDS Specification

Alternatived Products of [ 502161-03-7 ]

Product Details of [ 502161-03-7 ]

CAS No. :	502161-03-7	MDL No. :	MFCD09261276
Formula :	C₁₈H₁₂IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PJUAIXDOXUXBDR-UHFFFAOYSA-N
M.W :	369.20	Pubchem ID :	11810740
Synonyms :

Calculated chemistry of [ 502161-03-7 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	19
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	93.5
TPSA :	4.93 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.28
Log Po/w (XLOGP3) :	5.65
Log Po/w (WLOGP) :	5.39
Log Po/w (MLOGP) :	5.12
Log Po/w (SILICOS-IT) :	5.02
Consensus Log Po/w :	4.89

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-6.33
Solubility :	0.000174 mg/ml ; 0.000000473 mol/l
Class :	Poorly soluble
Log S (Ali) :	-5.52
Solubility :	0.00112 mg/ml ; 0.00000304 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.55
Solubility :	0.0000105 mg/ml ; 0.0000000284 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.2

Safety of [ 502161-03-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 502161-03-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 502161-03-7 ]
Downstream synthetic route of [ 502161-03-7 ]

[ 502161-03-7 ] Synthesis Path-Upstream 1~8

1
[ 1150-62-5 ]
[ 57103-21-6 ]
[ 502161-03-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 933 - 941
[2] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 933 - 941
[3] Tetrahedron Letters, 2006, vol. 47, # 39, p. 6957 - 6960

2
[ 1150-62-5 ]
[ 502161-03-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With iodine; acetic acid; periodic acid In water at 80℃; for 2 h;	2.433 g (10 mmol) of the intermediate compound A was added to 100 mL of 80percent acetic acid, and then 1.357 g (5.35 mmol) of iodine (I₂) and 0.333 g (1.46 mmol) of ortho-periodinic acid (H₅IO₆) were added thereto. The resultant was stirred under nitrogen atmosphere at 80°C for 2 hrs. After the reaction was completed, the reaction mixture was three times extracted with ethyl ether (50 mL). The collected organic layer was dried on magnesium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography to obtain 3.23 g of the intermediate compound B as a white solid (yield: 87percent). ¹H NMR (CDCl₃, 300MHz) δ (ppm) 8.43 (d, 1H), 8.05 (d, 1H), 7.62 (dd, 1H), 7.61-7.75 (m, 2H), 7.51-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.27 (dd, 1H), 7.14 (d, 1H)
87%	With iodine; acetic acid; periodic acid In water at 80℃; for 2 h;	Synthesis of Intermediate F; Intermediate E (2.433 g, 10 mmol) was added to an 80percent acetic acid (100 ml), and iodine (I₂) (1.357 g, 5.35 mmol) and ortho-periodinic acid (H₅lO₆) (0.333 g, 1.46 mmol) in a solid phase were added thereto. The reaction mixture was stirred at 80° C. under a nitrogen atmosphere for two hours. After the reaction was terminated, the reaction solution was extracted three times with ethylether (50 ml). The collected organic layer was dried over magnesium sulfate to evaporate a solvent. The resultant residue was purified by silica gel column chromatography to give intermediate F as a white solid (3.23 g, yield: 87percent). The structure of intermediate F was determined by ¹H NMR. ¹H NMR (CDCl₃, 300 MHz) δ (ppm) 8.43 (d, 1H), 8.05 (d, 1H), 7.62 (dd, 1H), 7.61-7.75 (m, 2H), 7.51-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.27 (dd, 1H), 7.14 (d, 1H)
87%	at 80℃; for 2 h; Inert atmosphere	2.433 g of phenylcarbazole (10 mmol) was added into 100 ml of 80percent acetic acid, and 1.357 g of Iodine (I₂) (5.35 mmol) and 0.333 g of ortho-periodic acid (H₅IO₆) (1.46 mmol) in a solid state were added thereto to form a mixture. The mixture was stirred at 80°C for 2 hours in a nitrogen atmosphere. A reaction was allowed to take place and terminated. After the reaction was terminated, the mixture was extracted with 50 ml of ethylether three times. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified by silica gel column chromatography to obtain 3.23 g (yield 87percent) of white solid of Intermediate 1. Intermediate 1 was evaluated by NMR, and the result thereof is shown below. ¹H NMR (CDCl₃, 300MHz) δ (ppm) 8.43 (d, 1H), 8.05 (d, 1H), 7.62 (dd, 1H), 7.61-7.75 (m, 2H), 7.51-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.27 (dd, 1H), 7.14 (d, 1H)

85%	at 80℃; for 2 h;	78.9 g (0.324 mol) of the compound represented by the formula 1-a obtained in the above reaction formula 1, 44.4 g (0.175 mol) of iodine, 11.1 g (0.0486 mol) of periodic acid,Acetic acid (500 mL) was added thereto, followed by stirring at 80 ° C for 2 hours.The reaction was cooled to room temperature and extracted with diethyl ether and water. The organic layer was dehydrated with magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography using hexane as a developing solvent to obtain 88.0 g (85percent) of the compound represented by the formula (1-b).
81%	With potassium iodate; sulfuric acid; potassium iodide In ethanol at 75℃; for 2 h;	Into a mixture of 17.7 g (72.7 mmol) of 9-phenylcarbazole, 6.03 g (36.3 mmol) of potassium iodide and 7.78 g (36.4 mmol) of potassium iodate, 5.9 ml of sulfuric acid and 70 ml of ethanol were added, and the resultant mixture was stirred at 75 °C for 2 h. After cooling, the reaction production was added with water and ethyl acetate and liquid-liquid extracted. The organic layer was washed with an aqueous solution of sodium hydrogencarbonate and water and then concentrated. The obtained crude product was purified by silica gel column chromatography, to obtain 21.8 g of a white solid, which was identified as the following intermediate 1-7 by FD-MS analysis (yield: 81percent).
78%	at 80℃; for 4 h;	400 mL of 85percent acetic acid was added to a mixture including 24.3 g (100.0 mmol) of phenyl carbazole, 13.4 g (50.3 mmol) of iodine, and 2.2 g (10.0 mmol) of periodic acid, and the mixture was heated at 80° C. for 4 hours. 500 mL of cold water was added to the reaction mixture, and the reaction mixture was stirred and filtered. A solid phase obtained by the filtration was cleaned with cold water several times. Then, the solid phase was dissolved in 400 mL of ethyl ether, dried, filtered, concentrated, and then separated using column chromatography to obtain 28.7 g of compound 4 in white solid form with a yield of 78percent. The structure of compound 4 was identified using HR-MS. (calc.: 369.0014, found: 369.0001)
77%	With sulfuric acid; iodine In methanol; water for 20 h;	500 g of methanol and 65.19 g (0.2568 mol) of iodine were added to 125 g (0.5137 mol) of Intermediate G, and the mixture was cooled to 5 or lower. 10 g (0.1 mol) of sulfuric acid was added to 500 g of water and diluted. While the cooled reactor was maintained at 5 ° C or lower, the diluted sulfuric acid aqueous solution was slowly added dropwise and stirred for 20 hours while maintaining the same temperature condition. The reaction mixture was concentrated under reduced pressure to remove methanol, 450 g of toluene was added thereto, and the organic layer was separated. The toluene was removed by concentration under reduced pressure, and 400 g of methanol was added thereto, followed by refluxing, cooling, filtration and drying to obtain 146 g (yield: 77percent) of intermediate H having a purity of 98.3percent .
77%	With sulfuric acid; iodine In methanol; water at 5℃; for 20 h; Cooling	To 125 g (0.5137 mol) of Intermediate G, 500 g of methanol,65.19 g (0.2568 mol) of iodine was added and cooled to 5°C or lower.10 g (0.1 mol) of sulfuric acid was added to 500 g of water, diluted, and the cooled reactor was slowly added dropwise while keeping the temperature at 5°C or lower. After completing the drop, The reaction was completed by stirring for 20 hours while maintaining the same temperature conditions.The methanol was removed by concentration under reduced pressure, 450 g of toluene was added, the organic layer was separated, toluene was removed under reduced pressure,Methanol (400 g) was added,Cooling, filtration and drying were conducted to obtain 146 g (yield: 77percent) of Intermediate H having a purity of 98.3percent.
67%	With N-iodo-succinimide In acetic acid at 20℃;	24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodosuccinimide was slowly added thereto, and then stirring was carried out at a room temperature fro overnight. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 24.7g (yield 67percent) of 3-iodo-9-phenylcarbazole which was white powder, was obtained.1Og (lO.Ommol) of 9-phenyl carbazole, 838mg (5.0mmol) of potassium iodide, l.lg (5.0mmol) of potassium iodate, and 3OmL of glacial acetic acid were put in a three-neck flask and refluxed for 1 hour at 120 ⁰C. After the reaction, the reaction EPO <DP n="56"/>solution was cooled sufficiently and added into water, extracted with toluene, an organic layer was washed with saturated sodium chloride solution once, was dried with magnesium sulfate. This solution was filtered naturally, and the obtained filtrate was concentrated. Then, it was recrystallized with acetone and methanol. 8.0 g (the yield: 50percent) of a white solid, which was an objective substance, was obtained.
67%	With N-iodo-succinimide In acetic acid at 20℃;	4.9 g (20 mmol) of N-phenylcarbazole was dissolved in 100 ml of glacial acetic acid, 4.48 g (20 mmol) of N-iodinesuccinimide was gradually added thereto, and then stirring was carried out at a room temperature overnight. The solution became clouded at 2.5 hours from the reaction started, and was suspended by a light orange precipitate at 3.5 hours from the reaction started. This suspension was dropped to 300 ml of the saturated aqueous solution of sodium chloride to obtain a light salmon pink block object. After washing this block object three times with water, 200 ml of ethyl acetate was added to dissolve the block object, and washing was carried out with sodium hydrogen carbonate and then with water. After magnesium sulfate was added to remove moisture, magnesium sulfate was removed by filtration. Recrystallization was carried out to obtain 5 g of white powder in a yield of 68 percent by heating this solution to which hexane was added.Alternatively, 3-iodine-9-phenylcarbazole also can be synthesized by the following method. 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodinesuccinimide was gradually added thereto, and stirring was carried out at a room temperature overnight. The solution EPO <DP n="59"/>became clouded at 2.5 hours from the reaction started, and was suspended by a light orange precipitate at 3.5 hours from the reaction started. This suspension was filtered. The filtrated object was washed with sodium hydrogen carbonate, then with water. Finally, the filtrated was washed with methanol to obtain 24.7 g of white powder in a yield of 67 percent. [Step 4]
50%	With potassium iodate; potassium iodide In acetic acid at 120℃; for 1 h; Heating / reflux	24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodosuccinimide was slowly added thereto, and then stirring was carried out at a room temperature fro overnight. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 24.7g (yield 67percent) of 3-iodo-9-phenylcarbazole which was white powder, was obtained.1Og (lO.Ommol) of 9-phenyl carbazole, 838mg (5.0mmol) of potassium iodide, l.lg (5.0mmol) of potassium iodate, and 3OmL of glacial acetic acid were put in a three-neck flask and refluxed for 1 hour at 120 ⁰C. After the reaction, the reaction EPO <DP n="56"/>solution was cooled sufficiently and added into water, extracted with toluene, an organic layer was washed with saturated sodium chloride solution once, was dried with magnesium sulfate. This solution was filtered naturally, and the obtained filtrate was concentrated. Then, it was recrystallized with acetone and methanol. 8.0 g (the yield: 50percent) of a white solid, which was an objective substance, was obtained.
21.8 g	With potassium iodate; sulfuric acid; potassium iodide In ethanol at 75℃; for 2 h;	17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.90 mL of sulfuric acid and ethanol were placed and reacted at 75° C. for 2 hours.After cooling, water and ethyl acetate were added thereto to be separated into a water phase and an organic phase. The organic phase was extracted, washed with sodium bicarbonate water and water, and concentrated to obtain a crude product. The crude product was purified with silica gel chromatography (with toluene), and the resultant solids were dried under reduced pressure to obtain 21.8 g of white solids. The solids were identified as Intermediate 1 by FD-MS analysis.
21.8 g	With potassium iodate; sulfuric acid; potassium iodide In ethanol at 75℃; for 2 h;	After adding 5.90 mL of sulfuric acid and 70 mL of ethanol to 17.7 g of 9-phenylcarbazole, 6.03 g of potassiumiodide and 7.78 g of potassium iodate, the resultant mixture was allowed to react at 75 °C for 2 h. After cooling, waterand ethyl acetate were added and the resultant mixture was subjected to liquid-liquid extraction. The organic layer waswashed with an aqueous sodium hydrogen carbonate solution and water and then concentrated. The obtained crudeproduct was purified by silica gel column chromatography. The purified solid was vacuum-dried to obtain 21.8 g of whilesolid, which was identified as Intermediate 2 shown below by FD-MS analysis.

Reference： [1] Patent: EP1661888, 2006, A1, . Location in patent: Page/Page column 11
[2] Patent: US2008/174237, 2008, A1, . Location in patent: Page/Page column 13-14
[3] Patent: EP2149555, 2010, A1, . Location in patent: Page/Page column 19
[4] Patent: KR101791161, 2017, B1, . Location in patent: Paragraph 0116; 0123-0128
[5] Patent: EP2738166, 2014, A1, . Location in patent: Paragraph 0162
[6] Patent: US8865322, 2014, B2, . Location in patent: Page/Page column 25; 26; 38; 39
[7] Patent: KR2016/19744, 2016, A, . Location in patent: Paragraph 0058; 0061; 0062; 0079; 0082; 0083
[8] Patent: KR2016/19745, 2016, A, . Location in patent: Paragraph 0047; 0051-0052
[9] Patent: WO2006/70912, 2006, A1, . Location in patent: Page/Page column 54
[10] Patent: WO2006/43647, 2006, A1, . Location in patent: Page/Page column 56
[11] Patent: WO2006/70912, 2006, A1, . Location in patent: Page/Page column 54; 55
[12] Patent: US2007/31701, 2007, A1,
[13] Patent: EP2085382, 2009, A1, . Location in patent: Page/Page column 38
[14] Patent: EP2100880, 2009, A1, . Location in patent: Page/Page column 14-15
[15] Patent: EP2468725, 2012, A1, . Location in patent: Page/Page column 119
[16] Patent: EP2484665, 2012, A1, . Location in patent: Page/Page column 62
[17] Patent: EP2502908, 2012, A1, . Location in patent: Page/Page column 41
[18] Patent: US2012/273766, 2012, A1, . Location in patent: Page/Page column 70
[19] Patent: EP2527334, 2012, A1, . Location in patent: Page/Page column 89
[20] Patent: EP2617712, 2013, A1, . Location in patent: Paragraph 0157
[21] Patent: EP2690093, 2014, A1, . Location in patent: Paragraph 0130

3
[ 86-74-8 ]
[ 502161-03-7 ]

Reference： [1] Patent: KR2016/19744, 2016, A,
[2] Patent: KR2016/19745, 2016, A,
[3] Patent: KR101791161, 2017, B1,

4
[ 108-86-1 ]
[ 502161-03-7 ]

Reference： [1] Patent: KR2016/19744, 2016, A,
[2] Patent: KR2016/19745, 2016, A,
[3] Patent: KR101791161, 2017, B1,

5
[ 1150-62-5 ]
[ 57103-21-6 ]
[ 502161-03-7 ]

6
[ 502161-03-7 ]
[ 1060735-14-9 ]

Reference： [1] Patent: EP2690093, 2014, A1,

7
[ 73183-34-3 ]
[ 502161-03-7 ]
[ 1126522-69-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium <i>tert</i>-butylate In toluene at 90℃; for 6 h; Inert atmosphere	100 mL of toluene was added to a mixture including 11.1 g (30.0 mmol) of compound 4, 9.1 g (36.0 mmol) of bis(pinacolato)diboron, 1.2 g (0.05 mole percent) of Pd(dppf)Cl₂, and 3.5 g (36 mmol) of KO^tBu, and then the mixture was heated at 90° C. in a nitrogen atmosphere for 6 hours. The reaction mixture was cooled to room temperature, 50 mL of water was further added to the reaction mixture, and the reaction mixture was subjected to extraction twice with 300 mL of methylene chloride. The resultant organic layer was dried, filtered, concentrated, and then separated using column chromatography to obtain 8.74 g of compound 6 in pale yellow solid form with a yield of 79percent.
62%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 3 h; Inert atmosphere	A 1000 mL 2-neck round bottom flask was charged with 3-iodo-9-phenyl-9H-carbazole (100.0 mmol, 36.9 g),bis(pinacolato)diboron(150.0 mmol, 38.1 g),PdCl2 (dppf) (3.0 mmol, 2.45 g),Potassium acetate (300.0 mmol, 29.4 g) was added, and nitrogenRespectively. 500 ml of dimethylformamide was added as a solvent, and the mixture was stirred at 80 ° C for 3 hours. The temperature of the reaction solution was lowered to room temperature and extracted with dichloromethane. The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain crude product. The crude product was separated and purified by silica gel column chromatography to obtain 22.9 g (yield: 62percent) of intermediate 47-1 as a yellow solid.
62%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 3 h; Inert atmosphere	In a 1000 mL two-neck round bottom flask3-iodo-9-phenyl-9H-carbazole (100.0 mmol, 36.9 g)bis(pinacolato)diboron(150.0 mmol, 38.1 g),PdCl2 (dppf) (3.0 mmol, 2.45 g),Potassium acetate (300.0 mmol, 29.4 g) was charged and charged with nitrogen. 500 ml of dimethylformamide was added as a solvent, and the mixture was stirred at 80 ° C for 3 hours.The temperature of the reaction solution was lowered to room temperature and extracted with dichloromethane. The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain crude product. The crude product was separated and purified by silica gel column chromatography to obtain 22.9 g (yield: 62percent) of intermediate 47-1 as a yellow solid.

Reference： [1] Patent: US8865322, 2014, B2, . Location in patent: Paragraph 39; 40
[2] Patent: KR2017/90390, 2017, A, . Location in patent: Paragraph 0264; 0265-0268
[3] Patent: KR101763838, 2017, B1, . Location in patent: Paragraph 0223-0227

8
[ 61676-62-8 ]
[ 502161-03-7 ]
[ 1126522-69-7 ]

Reference： [1] Journal of Materials Chemistry, 2012, vol. 22, # 1, p. 123 - 129

[ 502161-03-7 ] Synthesis Path-Downstream 1~88

1
[ 1150-62-5 ]
[ 57103-21-6 ]
[ 502161-03-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 933 - 941
[2]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 933 - 941
[3]Tetrahedron Letters,2006,vol. 47,p. 6957 - 6960

2
[ 531-91-9 ]
[ 502161-03-7 ]
C₆₀H₄₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h;	912 mg (2.47 mmol) of the intermediate compound B, 336.4 mg (1 mmol) of the intermediate compound C, 300 mg (3 mmol) of t-BuONa, 40 mg (0.02 mmol) of Pd2(dba)3, and 3 mg (0.01 mmol) of P(t-Bu)3 were dissolved in 5 mL of toluene, and then stirred at 90C for 3 hrs. After the reaction was completed, the resultant was cooled to room temperature and three times extracted with distilled water and diethyl ether. The collected organic layer was dried on magnesium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography to obtain 570 mg of Compound represented by Formula 3 as a yellow solid (yield: 70%). 1H NMR (CDCl3, 300MHz) delta (ppm) 7.99 (d, 2H), 7.95 (s, 2H), 7.61-7.57 (m, 8H), 7.48-7.32 (m, 12H), 7.27-7.19 (m, 8H), 7.18-7.10 (m, 8H), 6.96 (t, 2H); 13C NMR (CDCl3, 100MHz) delta (ppm) 148.4, 147.3, 141.3, 140.4, 138.0, 137.6, 133.9, 129.9, 129.1, 127.4, 127.1, 127.0, 126.1, 125.6, 124.3, 123.0, 122.9, 122.8, 121.7, 120.5, 119.9, 118.5, 110.7, 109.9. The obtained Compound represented by Formula 3 was diluted with CHCl3 to a concentration of 0.2 mM and the UV spectrum therefor was obtained. A maximum absorption wavelength of 351 nm was observed in the UV spectrum (FIG. 2). Further, Compound represented by Formula 3 was subjected to thermal analysis using TGA (Thermo Gravimetric Analysis) and DSC (Differential Scanning Calorimetry) (N2 atmosphere, temperature range: room temperature-600C (10C/min)-TGA, room temperature-400C - DSC, Pan type: Pt pan in disposable Al pan (TGA), disposable Al pan (DSC)) to obtain Td 494C and Tg 153C (FIGS. 3 and 4). A HOMO (Highest Occupied Molecular Orbital) energy level of 5.16 eV and a LUMO (Lowest Occupied Molecular Orbital) energy level of 2.16 eV were obtained using UV absorption spectrum and a potentiometer AC-2.

Reference： [1]Patent: EP1661888,2006,A1 .Location in patent: Page/Page column 11-12

3
[ 873-74-5 ]
[ 502161-03-7 ]
[ 873793-84-1 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h;	3.69 g (10 mmol) of the intermediate compound B, 1.42 g (12 mmol) of 4-aminobenzonitrile, 1.44 g (15 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd2(dba)3, and 40 mg (0.2 mmol) of P(t-Bu)3 were dissolved in 50 mL of toluene, and then stirred at 90C for 3 hrs. After the reaction was completed, the reaction mixture was cooled to room temperature and three times extracted with distilled water and diethyl ether. The collected organic layer was dried on magnesium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography to obtain 1.8 g of the intermediate compound D (yield: 50%).

Reference： [1]Patent: EP1661888,2006,A1 .Location in patent: Page/Page column 12-13

4
[ 1150-62-5 ]
[ 502161-03-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With iodine; acetic acid; periodic acid; In water; at 80℃; for 2h;	2.433 g (10 mmol) of the intermediate compound A was added to 100 mL of 80% acetic acid, and then 1.357 g (5.35 mmol) of iodine (I2) and 0.333 g (1.46 mmol) of ortho-periodinic acid (H5IO6) were added thereto. The resultant was stirred under nitrogen atmosphere at 80C for 2 hrs. After the reaction was completed, the reaction mixture was three times extracted with ethyl ether (50 mL). The collected organic layer was dried on magnesium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography to obtain 3.23 g of the intermediate compound B as a white solid (yield: 87%). 1H NMR (CDCl3, 300MHz) delta (ppm) 8.43 (d, 1H), 8.05 (d, 1H), 7.62 (dd, 1H), 7.61-7.75 (m, 2H), 7.51-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.27 (dd, 1H), 7.14 (d, 1H)
87%	With iodine; acetic acid; periodic acid; In water; at 80℃; for 2h;	Synthesis of Intermediate F; Intermediate E (2.433 g, 10 mmol) was added to an 80% acetic acid (100 ml), and iodine (I2) (1.357 g, 5.35 mmol) and ortho-periodinic acid (H5lO6) (0.333 g, 1.46 mmol) in a solid phase were added thereto. The reaction mixture was stirred at 80 C. under a nitrogen atmosphere for two hours. After the reaction was terminated, the reaction solution was extracted three times with ethylether (50 ml). The collected organic layer was dried over magnesium sulfate to evaporate a solvent. The resultant residue was purified by silica gel column chromatography to give intermediate F as a white solid (3.23 g, yield: 87%). The structure of intermediate F was determined by 1H NMR. 1H NMR (CDCl3, 300 MHz) delta (ppm) 8.43 (d, 1H), 8.05 (d, 1H), 7.62 (dd, 1H), 7.61-7.75 (m, 2H), 7.51-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.27 (dd, 1H), 7.14 (d, 1H)
87%	With iodine; acetic acid; periodic acid; at 80℃; for 2h;Inert atmosphere;	2.433 g of phenylcarbazole (10 mmol) was added into 100 ml of 80% acetic acid, and 1.357 g of Iodine (I2) (5.35 mmol) and 0.333 g of ortho-periodic acid (H5IO6) (1.46 mmol) in a solid state were added thereto to form a mixture. The mixture was stirred at 80C for 2 hours in a nitrogen atmosphere. A reaction was allowed to take place and terminated. After the reaction was terminated, the mixture was extracted with 50 ml of ethylether three times. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified by silica gel column chromatography to obtain 3.23 g (yield 87%) of white solid of Intermediate 1. Intermediate 1 was evaluated by NMR, and the result thereof is shown below. 1H NMR (CDCl3, 300MHz) delta (ppm) 8.43 (d, 1H), 8.05 (d, 1H), 7.62 (dd, 1H), 7.61-7.75 (m, 2H), 7.51-7.43 (m, 3H), 7.41-7.35 (m, 2H), 7.27 (dd, 1H), 7.14 (d, 1H)

85%	With iodine; acetic acid; periodic acid; at 80℃; for 2h;	78.9 g (0.324 mol) of the compound represented by the formula 1-a obtained in the above reaction formula 1, 44.4 g (0.175 mol) of iodine, 11.1 g (0.0486 mol) of periodic acid,Acetic acid (500 mL) was added thereto, followed by stirring at 80 C for 2 hours.The reaction was cooled to room temperature and extracted with diethyl ether and water. The organic layer was dehydrated with magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography using hexane as a developing solvent to obtain 88.0 g (85%) of the compound represented by the formula (1-b).
81%	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	Into a mixture of 17.7 g (72.7 mmol) of 9-phenylcarbazole, 6.03 g (36.3 mmol) of potassium iodide and 7.78 g (36.4 mmol) of potassium iodate, 5.9 ml of sulfuric acid and 70 ml of ethanol were added, and the resultant mixture was stirred at 75 C for 2 h. After cooling, the reaction production was added with water and ethyl acetate and liquid-liquid extracted. The organic layer was washed with an aqueous solution of sodium hydrogencarbonate and water and then concentrated. The obtained crude product was purified by silica gel column chromatography, to obtain 21.8 g of a white solid, which was identified as the following intermediate 1-7 by FD-MS analysis (yield: 81%).
78%	With iodine; acetic acid; periodic acid; at 80℃; for 4h;	400 mL of 85% acetic acid was added to a mixture including 24.3 g (100.0 mmol) of phenyl carbazole, 13.4 g (50.3 mmol) of iodine, and 2.2 g (10.0 mmol) of periodic acid, and the mixture was heated at 80 C. for 4 hours. 500 mL of cold water was added to the reaction mixture, and the reaction mixture was stirred and filtered. A solid phase obtained by the filtration was cleaned with cold water several times. Then, the solid phase was dissolved in 400 mL of ethyl ether, dried, filtered, concentrated, and then separated using column chromatography to obtain 28.7 g of compound 4 in white solid form with a yield of 78%. The structure of compound 4 was identified using HR-MS. (calc.: 369.0014, found: 369.0001)
77%	With sulfuric acid; iodine; In methanol; water; for 20h;	500 g of methanol and 65.19 g (0.2568 mol) of iodine were added to 125 g (0.5137 mol) of Intermediate G, and the mixture was cooled to 5 or lower. 10 g (0.1 mol) of sulfuric acid was added to 500 g of water and diluted. While the cooled reactor was maintained at 5 C or lower, the diluted sulfuric acid aqueous solution was slowly added dropwise and stirred for 20 hours while maintaining the same temperature condition. The reaction mixture was concentrated under reduced pressure to remove methanol, 450 g of toluene was added thereto, and the organic layer was separated. The toluene was removed by concentration under reduced pressure, and 400 g of methanol was added thereto, followed by refluxing, cooling, filtration and drying to obtain 146 g (yield: 77%) of intermediate H having a purity of 98.3% .
77%	With sulfuric acid; iodine; In methanol; water; at 5℃; for 20h;Cooling;	To 125 g (0.5137 mol) of Intermediate G, 500 g of methanol,65.19 g (0.2568 mol) of iodine was added and cooled to 5C or lower.10 g (0.1 mol) of sulfuric acid was added to 500 g of water, diluted, and the cooled reactor was slowly added dropwise while keeping the temperature at 5C or lower. After completing the drop, The reaction was completed by stirring for 20 hours while maintaining the same temperature conditions.The methanol was removed by concentration under reduced pressure, 450 g of toluene was added, the organic layer was separated, toluene was removed under reduced pressure,Methanol (400 g) was added,Cooling, filtration and drying were conducted to obtain 146 g (yield: 77%) of Intermediate H having a purity of 98.3%.
67%	With N-iodo-succinimide; In acetic acid; at 20℃;Product distribution / selectivity;	24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodosuccinimide was slowly added thereto, and then stirring was carried out at a room temperature fro overnight. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 24.7g (yield 67%) of 3-iodo-9-phenylcarbazole which was white powder, was obtained.1Og (lO.Ommol) of 9-phenyl carbazole, 838mg (5.0mmol) of potassium iodide, l.lg (5.0mmol) of potassium iodate, and 3OmL of glacial acetic acid were put in a three-neck flask and refluxed for 1 hour at 120 0C. After the reaction, the reaction EPO <DP n="56"/>solution was cooled sufficiently and added into water, extracted with toluene, an organic layer was washed with saturated sodium chloride solution once, was dried with magnesium sulfate. This solution was filtered naturally, and the obtained filtrate was concentrated. Then, it was recrystallized with acetone and methanol. 8.0 g (the yield: 50%) of a white solid, which was an objective substance, was obtained.
67 - 68%	With N-iodo-succinimide; In acetic acid; at 20℃;Product distribution / selectivity;	4.9 g (20 mmol) of N-phenylcarbazole was dissolved in 100 ml of glacial acetic acid, 4.48 g (20 mmol) of N-iodinesuccinimide was gradually added thereto, and then stirring was carried out at a room temperature overnight. The solution became clouded at 2.5 hours from the reaction started, and was suspended by a light orange precipitate at 3.5 hours from the reaction started. This suspension was dropped to 300 ml of the saturated aqueous solution of sodium chloride to obtain a light salmon pink block object. After washing this block object three times with water, 200 ml of ethyl acetate was added to dissolve the block object, and washing was carried out with sodium hydrogen carbonate and then with water. After magnesium sulfate was added to remove moisture, magnesium sulfate was removed by filtration. Recrystallization was carried out to obtain 5 g of white powder in a yield of 68 % by heating this solution to which hexane was added.Alternatively, 3-iodine-9-phenylcarbazole also can be synthesized by the following method. 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodinesuccinimide was gradually added thereto, and stirring was carried out at a room temperature overnight. The solution EPO <DP n="59"/>became clouded at 2.5 hours from the reaction started, and was suspended by a light orange precipitate at 3.5 hours from the reaction started. This suspension was filtered. The filtrated object was washed with sodium hydrogen carbonate, then with water. Finally, the filtrated was washed with methanol to obtain 24.7 g of white powder in a yield of 67 %. [Step 4]
50%	With potassium iodate; potassium iodide; In acetic acid; at 120℃; for 1h;Heating / reflux;Product distribution / selectivity;	24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodosuccinimide was slowly added thereto, and then stirring was carried out at a room temperature fro overnight. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 24.7g (yield 67%) of 3-iodo-9-phenylcarbazole which was white powder, was obtained.1Og (lO.Ommol) of 9-phenyl carbazole, 838mg (5.0mmol) of potassium iodide, l.lg (5.0mmol) of potassium iodate, and 3OmL of glacial acetic acid were put in a three-neck flask and refluxed for 1 hour at 120 0C. After the reaction, the reaction EPO <DP n="56"/>solution was cooled sufficiently and added into water, extracted with toluene, an organic layer was washed with saturated sodium chloride solution once, was dried with magnesium sulfate. This solution was filtered naturally, and the obtained filtrate was concentrated. Then, it was recrystallized with acetone and methanol. 8.0 g (the yield: 50%) of a white solid, which was an objective substance, was obtained.
	With N-iodo-succinimide; In acetic acid;	[Step 1] A synthesis method of 3-iodo-9-phenylcarbazole will be explained. A synthesis scheme of 3-iodo-9-phenylcarbazole is shown in (j-1). 24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 mL of glacial acetic acid, 22.5g (100 mmol) of N-iodosuccinimide was slowly added thereto, and the mixture was stirred at a room temperature for about 20 hours. The generated precipitate was filtered, and the residue was washed with a saturated sodium hydrogen carbonate solution, water, and methanol, and then dried. 24.7 g (yield: 67%) of 3-iodo-9-phenylcarbazole, which was white powder, was obtained. It is to be noted that 3-iodo-9-phenylcarbazole can be synthesised by the following method. 10 g (10.0 mmol) of N-phenylcarbazole, 838 mg (5.0 mmol) of potassium iodide, 1.1 g (5.0 mmol) of potassium iodate, and 30 mL of glacial acetic acid were put in a three-neck flask and refluxed at 120 C. for 1 hour.
	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	Blending 17.7 g of 9-phenyl carbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.90 ml of sulfuric acid and ethanol, the reaction was allowed to proceed at 75 C for 2 h. The resultant solution was cooled, and adding tap water and ethyl acetate, it was separated and extracted. Subsequently, an organic layer was washed with sodium bicarbonate water and tap water and then, it was condensed. Purifying the resultant crude product by means of a silicagel chromatography (toluene), vacuum dried the resultant solid to obtain 21.8 g of white solid, which was analyzed by FD-MS (Field Desorption Mass Spectrum) and identified as Intermediate 1.
	With potassium iodate; potassium iodide; In acetic acid; at 80℃; for 2h;	The 9-phenylcarbazole was dissolved in 300mL of acetic acid, and then 7 g of potassium iodide and 18 g of potassium iodate were added to the resultant. The resulting solution was reacted at a temperature of 80C for two hours. After completion of the reaction, unreacted iodine in the resulting reaction mixture was reduced with aqueous solution of sodium thiosulfate, and then the reaction mixture was concentrated, followed by purifying the resulting concentrate by silica gel column chromatography. The resulting viscous liquid was subjected to crystallization from hexane to provide 20.5 g of 3-iodo-9-phenylcarbazole (1) as white solid.
	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;Product distribution / selectivity;	17.7 Grams of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.9 ml of sulfuric acid, and ethanol were loaded into a 200-ml three-necked flask, and then the mixture was subjected to a reaction at 75C for 2 hours. After the resultant had been cooled, water and ethyl acetate were added to perform separation and extraction. After that, the organic layer was washed with baking soda water and water, and was then concentrated. The resultant coarse product was purified by silica gel chromatography (toluene), and then the resultant solid was dried under reduced pressure. Thus, 21.8 g of a white solid were obtained. The solid was identified as the intermediate-5 by FD-MS analysis.
	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.9 mL of sulfuric acid, and ethanol were loaded, and then the mixture was subjected to a reaction at 75C for 2 hours. After the resultant had been cooled, clean water and ethyl acetate were added to perform separation and extraction. After that, the organic layer was washed with baking soda water and clean water, and was then concentrated. The resultant coarseproduct was purified by silica gel chromatography (toluene), and then the resultant solid was dried under reduced pressure. Thus, 21.8 g of a white solid were obtained. The solid was identified as the Intermediate 3 by FD-MS analysis.
	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	5.90 mL of sulfuric acid, and ethanol were added to 17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, and 7.78 g of potassium iodate, and then the mixture was subjected to a reaction at 75C for 2 hours. After the resultant had been cooled, water and ethyl acetate were added to perform separation and extraction. After that, the organic layer was washed with baking soda water and water, and was then concentrated. The resultant coarse product was purified by silica gel chromatography (developing solvent: toluene), and then the resultant solid was dried under reduced pressure. Thus, 21.8 g of a white solid were obtained. The white solid was identified as the intermediate 7 by FD-MS analysis.
	With potassium iodate; sulfuric acid; In ethanol; water; at 75℃; for 2h;	17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.90 mL of sulfuric acid and ethanol were placed and reacted at 75 C. for 2 hours.After cooling, water and ethyl acetate was added thereto. After the resulting mixture was separated and extracted, an organic phase thereof was washed with sodium bicarbonate water and water, and concentrated. The crude product obtained was purified by silica-gel chromatography (toluene), and the solids obtained were dried under reduced pressure to obtain 21.8 g of white solids. The white solids were identified as Intermediate 1 by FD-MS analysis.
	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	Synthesis Example 9 (synthesis of intermediate 9)> 5.90 mL of sulfuric acid and ethanol were added to 17.7 g of 9-phenylcarbazole, 6.03g of potassium iodide, and 7.78 g of potassium iodate, and then the mixture was reacted at 75C for 2 hours. After the resultant had been cooled, water and ethyl acetate were added and extracted the resultant. After that, the organic layer was washed with baking soda water and water, and was then concentrated. The resultant coarse product was purified by silica gel chromatography (developing solvent: toluene), and then the resultant solid was dried under reduced pressure. Thus, 21.8 g of a white solid were obtained. The white solid was identified as the intermediate 9 by FD-MS analysis.
21.8 g	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.90 mL of sulfuric acid and ethanol were placed and reacted at 75 C. for 2 hours.After cooling, water and ethyl acetate were added thereto to be separated into a water phase and an organic phase. The organic phase was extracted, washed with sodium bicarbonate water and water, and concentrated to obtain a crude product. The crude product was purified with silica gel chromatography (with toluene), and the resultant solids were dried under reduced pressure to obtain 21.8 g of white solids. The solids were identified as Intermediate 1 by FD-MS analysis.
21.8 g	With potassium iodate; sulfuric acid; potassium iodide; In ethanol; at 75℃; for 2h;	After adding 5.90 mL of sulfuric acid and 70 mL of ethanol to 17.7 g of 9-phenylcarbazole, 6.03 g of potassiumiodide and 7.78 g of potassium iodate, the resultant mixture was allowed to react at 75 C for 2 h. After cooling, waterand ethyl acetate were added and the resultant mixture was subjected to liquid-liquid extraction. The organic layer waswashed with an aqueous sodium hydrogen carbonate solution and water and then concentrated. The obtained crudeproduct was purified by silica gel column chromatography. The purified solid was vacuum-dried to obtain 21.8 g of whilesolid, which was identified as Intermediate 2 shown below by FD-MS analysis.

Reference： [1]Patent: EP1661888,2006,A1 .Location in patent: Page/Page column 11
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[12]Patent: US2007/31701,2007,A1
[13]Patent: EP2085382,2009,A1 .Location in patent: Page/Page column 38
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5
[ 134-32-7 ]
[ 502161-03-7 ]
3-[N-(1-naphtyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 18-crown-6 ether; potassium carbonate;copper(l) iodide; at 170℃; for 24h;Product distribution / selectivity;	3.69 g (0.01 mol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 716 mg (5 mmol) of1-naphtylamine, 385 mg (2 mmol) of copper iodide, 2.74g (0.02 mol) of potassium carbonate, and 771mg (0.02 mol) of 18-crown 6-ether were put in a 200-mL three-neck flask, and the atmosphere of the flask was substituted by nitrogen, 8 mL of DMPU was added thereto, and stirred at 170 0C for 24 hours. The reaction solution was cooled at EPO <DP n="71"/>a room temperature, washed with water twice and water phase was extracted with toluene twice, the extracted solution and organic phase, which had been washed in advance, were mixed and washed with saturated sodium chloride solution, and dried with magnesium sulfate. The solution was filtrated naturally, and a compound obtained by concentrating the filtrate was purified with silca gel chromatography (hexane: toluene= 7:3) to obtain an objective substance, i.e., 1.52g (the yield :48 %) of a light-yellow solid.

Reference： [1]Patent: WO2006/70912,2006,A1 .Location in patent: Page/Page column 69; 70

6
[ 134-32-7 ]
[ 502161-03-7 ]
[ 894791-44-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 90℃; for 7h;	Under nitrogen, 12 ml of dehydrated xylene was added to a mixture of 3.7g (10 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 1.6 g (5mmol) of 1-aminonaphtalene, 60 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), 0.2 mL of a hexane solution with 49 wt% of tri-tert-butylphosphine, and 3.0 g (30mmol) of sodium-rert-butoxide. This mixture was stirred while heating under nitrogen atmosphere at 900C for 7 hours. After the termination of the reaction, about 200 ml of heated toluene was added to the suspension and this suspension was filtered through florisil, alumina and Celite. The thus obtained filtrate was concentrated and the concentrated solution was purified by using silica gel column chromatography (toluene : hexane=l:l). This was concentrated and the obtained concentrated solution was recrystallized with hexane-ethyl acetate. 1.5 g (the yield: 79 %) of 3-[N-(l-naphtyl)amino]-9-phenylcarbazole which was cream-colored powder, was obtained. NuMR data are shown below. 1H-NMR (300MHz,DMSO-d): delta =7.13-7.71 (m, 15H), 7.85-7.88 (m, IH), 8.03 (s, IH), 8.15 (d, J =7.8, IH), 8.24 (s, IH), 8.36-8.39 (m, IH). FIG. 22 shows a chart of 1H-NMR, and FIG 23 shows an enlarged view of the portion of 6.50 to 8.50 ppm in FIG. 22.
79%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 90℃; for 7h;	[Embodiment 7]; "[0379]In this embodiment, a synthetic method of2-[N-(I -naphthyl)-No.-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene (abbreviation: 2PCNPA), which is the anthracene derivative of the present invention represented by Structural Formula (219), is specifically described. [0380][0381];[Step 1]; Synthesis of iV-(l-naphthyl)-JV-(9-phenylcarbazol-3-yl)amine (abbreviation: <n="165"/>PCN).; A synthetic scheme of N-(l-naphthyl)-No.-(9-phenylcarbazol-3-yl)amine (abbreviation: PCN) is shown in (C-16). [0382]9O0C[0383]3.7 g (10 mmol) of 3-iodine-9-phenylcarbazole, 1.6 g (5 mmol) of1-aminonaphthalene, 60 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium (0), 0.2 mL(0.5 mmol) of tri(t°t-butyl)phosphine (10wt% hexane solution), and 3.0 g (30 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and after nitrogen substitution was carried out in the flask, 12 mL of dehydrated xylene was added to the mixture. The reaction mixture was stirred for 7 hours at 90 0C under nitrogen. After the reaction was completed, about 200 mL of hot toluene was added to the reaction mixture, and the mixture was filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, and this concentrated solution was purified by silica gel column chromatography (eluting solvent was toluene:hexane=l:l). Recrystallization of the obtained solid with a mixed solvent of ethyl acetate and hexane gave 1.5 g ofJV-(l-naphthyl)-iV-(9-phenylcarbazol-3-yl)amine as light brown powder in 79% yield. It was confirmed by a nuclear magnetic resonance measurement (NMR) that this compound was JV~(l-naphthyl)-JV-(9-phenylcarbazol-3-yl)amine (abbreviation: PCN).[0384]1H NMR data of this compound is shown below. 1H NMR (300 MHz, DMSO-J6): delta = 7.13-7.71 (m, 15H), 7.85-7.88 (m, IH), 8.03 (s, IH), 8.15 (d,J = 7.8 Hz, IH), 8.24 (s, IH), 8.36-8.39 (m, IH).
79%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In xylene; at 90℃; for 7h;	Under nitrogen, 12 mL of dehydration xylene was added to a mixture of 3.7 g (10 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 1.6 g (5 mmol) of 1-aminonaphthalen, 60 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), 200 muL (0.5 mmol) of tri(t-butyl)phosphine (49 wt% hexane solution), 3 g (30 mmol) of t-butoxysodium (abbreviation: t-BuONa). This was stirred while heating at 90 0C under a nitrogen atmosphere for 7 hours. After the termination of the reaction, this suspension was added with about 200 mL of hot toluene and was filtered through florisil, alumina, and celite. The obtained filtrate was concentrated and this residue was separated by silica gel column chromatography (toluene: hexane = 1:1). When an obtained solid was recrystallized with a mixture of ethyl acetate and hexane, 1.5 g of 3-[N-(l-naphthyl)amino]-9-phenylcarbazole (PCN) that was a target substance and was cream-colored powder was obtained in a yield of 79 % (Synthesis Scheme (g-1)). [0208] EPO <DP n="75"/>Xylene(g-i)[0209]The 1H-NMR of the obtained PCN is shown below, and a 1H-NMR chart is shown in FIG 31A, and an enlarged chart of a portion of 6.5 to 8.5 ppm in FIG 31A is shown in FIG. 31B.1H-NMR (300 MHz, DMSO-d); delta = 7.13-7.71 (m, 15H), 7.85-7.88 (ra, IH), 8.03 (s, IH), 8.15 (d, J = 7.8, IH), 8.24 (s, IH), 8.36-8.39 (m, IH)

Reference： [1]Patent: WO2006/70912,2006,A1 .Location in patent: Page/Page column 63; 64
[2]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 162-163
[3]Patent: WO2007/29530,2007,A1 .Location in patent: Page/Page column 73-74

7
[ 62-53-3 ]
[ 502161-03-7 ]
3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With sodium t-butanolate;copper(l) iodide; tributylphosphine; In hexane; xylene; at 135℃; for 6h;Heating / reflux;Product distribution / selectivity;	1.60 mg (4.33 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 19.0 mg (0.1 mmol) of copper iodide(I), 1.10 g (10 mmol) of tert-butoxy potassium, 1.0 mL of tri-n- butylphosphine (0.2 mol/L dehydrogenated hexane solution) were put in a 200-mL three-neck flask, and the atmosphere of the flask was substituted by nitrogen, 10 mL of xylene, 0.2 mLof aniline (2.1 mmol, 195.6 mg) were added thereto, and refluxed at 135 0C for 6 hours. The reaction solution was cooled at a room temperature, and 100 mL EPO <DP n="70"/>of toluene was added thereto, then the mixture was filtered through florisil, and Celite. The obtained filtrate was washed with water twice and the water phase was extracted with toluene twice, the extracted solution and an organic phase which was washed with water were mixed and washed with saturated sodium chloride solution, and dried with magnesium sulfate. The solution was filtrated naturally, and a compound obtained by concentrating the filtrate was subjected to silica gel chromatography (a mixture solution of toluene and hexane) to obtain an objective substance. 140 mg (the yield : 21 %) of a light-yellow solid was obtained.

Reference： [1]Patent: WO2006/70912,2006,A1 .Location in patent: Page/Page column 68; 69

8
[ 894791-43-6 ]
[ 502161-03-7 ]
3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 90℃; for 6.5h;Product distribution / selectivity;	Under nitrogen, 40 ml of dehydrated xylene was added to a mixture of 3.7 g (10 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 3.4 g (10 mmol) of PCA, 57 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium (0), 0.2 mL (0.5 mmol) of tri-tert-butylphosphine 49wt%hexane solution, and 3.0 g (30 mmol) of sodium-tert-butoxide. This mixture was stirred while heating under nitrogen atmosphere at 9O0C for 6.5 hours. After the termination of the reaction, about 500 ml of heated toluene was added to the suspension and this suspension was filtered through florisil, alumina and Celite. The thus EPO <DP n="57"/>obtained filtrate was concentrated and the concentrated solution was purified by using silica gel column chromatography (toluene : hexane=l:l). This was concentrated and hexane-ethyl acetate was added thereinto to conduct recrystallization. 3.2 g (the yield: 56%) of 3-[Lambdar-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole which was cream-colored powder, was obtained. NMR data are shown below. 1H-NMR (300MHz,DMSO-d): delta = 6.85 (t, J =7.5, IH), 6.92 (d, J =7.8, 2H), 7.17-7.70 (m, 22H), 8.05 (d, J =2.1, 2H), 8.12 (d, J =7.8, 2H). FIG. 6 shows a chart of 1H-NMR, and FIG 7 shows an enlarged view of the portion of 6.75 to 8.50 ppm in FIG 6.

Reference： [1]Patent: WO2006/70912,2006,A1 .Location in patent: Page/Page column 55; 56

9
[ 894791-44-7 ]
[ 502161-03-7 ]
3-[N-(1-naphtyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 90℃; for 4.5h;Product distribution / selectivity;	Under nitrogen, 7 ml of dehydrated xylene was added to a mixture of 1.8 g (5 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 2.5 g (6.6 mmol) of PCN, 30 mg (0.05 mmol) of bis(dibenzylideneacetone)palladium(0), 0.2 mL (0.5 mmol) of a hexane solution with 49 wt% of tri-tert-butylphosphine, and 700 mg (7 mmol) of sodium-tert-butoxide. This mixture was stirred while heating under nitrogen atmosphere at 9O0C for 4.5 hours. After the termination of the reaction, about 500 ml of heated toluene was added to the suspension and this suspension was filtered through florisil, alumina and Celite. The thus obtained filtrate was concentrated and the concentrated solution was purified by using silica gel column chromatography (toluene : hexane=l:l). This was concentrated and the obtained concentrated solution was recrystallized with hexane-ethyl acetate. 2.1g (the yield: 62 %) of PCzPCNl which was yellow powder, was obtained. NMR data are shown below. 1H-NMR (300MHz,DMSO-d): delta = 7.04-7.65 (m, 24H), 7.78 (d, J =8.4, IH), 7.82 (d, J =2.1, 2H), 7.88 (d, J =7.8, 2H), 7.95 (d, J =8.4, IH), 8.10 (d, J =9.0, IH). FIG 24 shows a chart of 1H-NMR, and FIG. 25 shows an enlarged view of the portion of 6.50 to 8.50 ppm in FIG 24.

Reference： [1]Patent: WO2006/70912,2006,A1 .Location in patent: Page/Page column 64; 65

10
[ 19606-98-5 ]
[ 502161-03-7 ]
3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 0.216667h;Microwave irradiation;	627.64 mg (1.7 mmol) of 3-iodine-9-phenylcarbazol, 672.86 mg (2.0 mmol) of N-(4-diphenylaminophenyl)-N-phenylamine, 57.5 mg (0.1 mmol) of dibenzylideneacetonepalladium, and 335 mg (3.5 mmol) of sodium tert-butoxide were put into a three-necked flask, and the atmosphere in the flask was replaced by nitrogen. 3.5 ml of dehydrated toluene was added thereto and degassing was carried out for 3 minutes. After adding 0.4 ml of tri-tert-butylphosphine (10 w% hexane solution), the flask was shaked lightly up and down to stir the content. The solution was heated and stirred at 80 0C for 10 minutes with irradiating by a microwave at 200 W. After the reaction, saturated aqueous solution of sodium chloride was added, and the extraction with 100 ml of ethyl acetate was carried out. Further, magnesium sulfate was added to remove moisture, and then, magnesium sulfate was removed by filtration. Filtrate was EPO <DP n="60"/>condensed and purified by silica gel column using a solution of ethyl acetate and hexane in a ratio of 1:1. Hexane was added to the purified solution, and recrystallization was carried out to obtain 650 mg of cream powder in a yield of 65 %. The NMR data are indicated below. 1H NMR (300MHz, DMSO-d); delta=6.89-7.05 (m, 13H), 7.21-7.28 (m, 9H), 7.32-7.43 (m, 3H), 7.50-7.69 (m, 5H), 8.02(s, IH), 8.14 (d, j=7.2, 1 H). In addition, FIG. 13 shows a chart of 1H NMR, and FIG. 14 shows an enlarged view of the porition of 6.0 to 9.0 ppm in FIG. 13.

Reference： [1]Patent: WO2006/43647,2006,A1 .Location in patent: Page/Page column 57-58

11
[ 880800-17-9 ]
[ 502161-03-7 ]
3-[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 90℃; for 5.55h;	A flask was charged with 740 mg (2.0 mmoL) of 3-iodo-9-phenylcarbazol, 700 mg (1.8 mmol) of N-(4-diphenylaminophenyl)-N-(l-naphthyl)amine, 12 mg (0.02 mmol) of dibenzylideneacetonepalladium, and 6O0 mg (6.0 mmol) of sodium tert-butoxide and the atmosphere in the flask was replaced by nitrogen. 5 ml of dehydrated xylene was added thereto and degassing was carried out for 3 minutes. After 0.1ml (0.05 mmol) of tri-tert-butylphosphine (IO w% hexane solution) was added thereto, the solution was stirred for 5.5 hours at 90 0C in an atmosphere of nitrogen. Toluene of approximately 100 ml was added thereto and the solution is filtered through florisil, alumina, and celite. The obtained filtrate was washed with water and a saturated aqueous solution of sodium chloride. The organic layer was dried by magnesium sulfate. The obtained material was filtered, and condensed, then, purified by silica gel column chromatography (toluene and liexane in a ratio of 3:7). The obtained solution was condensed. Then, hexane was added thereto and the object was precipitated by using an ultra sonic washing machine. The obtained solid was filtered to obtain 500 mg of PCzTPNl as yellow powder in a yield of 44 %. The NMR data of the object are indicated below. 1H NMR (300MHz, DMSO-d); delta= 6.74 (d, j=8.7, 2H), 6.88-7.00 (m, 8H), 7.16-7.67 (m, 23H), 7.84 (d, j=8.4, IH), 7.97 (d, j=8.1, IH), 8.02 (s, EPO <DP n="74"/>IH), 8.08 (t, j=7.8, 2H). FIG. 24 shows chart of 1H NMR and FIG. 25 shows an enlarged view of the portion from 6.0 to 8.5 ppm in FIG. 24.

Reference： [1]Patent: WO2006/43647,2006,A1 .Location in patent: Page/Page column 71

12
[ 62-53-3 ]
[ 502161-03-7 ]
[ 894791-43-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris-(dibenzylideneacetone)dipalladium(0); PtBu3; potassium tert-butylate; In toluene; at 85℃; for 4h;	0.93 g (15 mmol) of aniline, 3.69 g (10 mmol) of <strong>[502161-03-7]3-iodo-9-phenyl-carbazole</strong>, 0.83 g (0.2 mmol) of Pd2(dba)3, 0.040 g (0.2 mmol) of PtBu3, and 13.9 g (20 mmol) of KOtBu were dissolved in 60 ml of toluene, and then the mixture was stirred at a temperature of 85 C. for 4 hours. The reaction solution was cooled to room temperature, and then extracted three times with 100 ml of water and 100 ml of diethylether. A collected organic layer was dried with a magnesium sulfate and the residual obtained by evaporating a solvent was separation-purified by silicagel column chromatography to obtain 2.63 g (Yield 79%) of Intermediate I-1. The formed compound was confirmed by MS/FAB. C24H18N2: calc. 334.14, found 334.21.
70%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 90℃; for 3h;	3.69 g (10.0 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 1.11 g (12.0 mmol) of aniline, 2.88 g (30.0 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd2(dba)3, and 40 mg (0.2 mmol) of P(t-Bu)3 were dissolved in 40 mL of toluene, and the reaction solution was stirred at 90 C. for 3 hours. When the reaction stopped, the solution was cooled to ambient temperature, and distilled water was added thereto, and then an organic layer was extracted three times by using 40 mL of diethyl ether. The obtained organic layer was dried by using MgSO4, and then a solvent was removed therefrom by distillation. The residue was separated and purified by silica gel column chromatography to obtain 2.34 g (yield of 70%) of Intermediate 1-1.
65%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h;	Synthesis of Intermediate B; 3.69 g (10.0 mmol) of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 1.11 g (12.0 mmol) of aniline, 2.88 g (30.0 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd2(dba)3, 40 mg (0.2 mmol) of P(t-Bu)3 were dissolved in 40 mL of toluene, and stirred at 90C for 3 hours. When the reaction was completed, the mixture was cooled to room temperature and distilled water was added thereto. The mixture was extracted three times with 40 mL of diethylether. A collected organic layer was dried over MgSO4 to evaporate the solvent. The residue was purified using silica gel column chromatography to obtain 2.17 g of white solid Intermediate B (Yield: 65 %). (1H NMR (CDCl3, 400MHz) delta (ppm) 8.01 (m, 1 H), 7.66 (m, 1 H), 7.51-7.33 (m, 7H), 7.21-6.94 (m, 5H), 6.73 (m, 1 H), 5.68 (bs, 1 H); 13C NMR (CDCl3, 100MHz) delta (ppm) 144.6, 139.8, 137.4, 135.7, 129.8, 129.3, 128.0, 127.4, 127.1, 126.5, 119.1, 119.0, 118.6, 118.4, 116.7, 113.1, 111.1, 109.4, 102.4).

With copper; potassium carbonate; In 1,3,5-trimethyl-benzene; at 165℃; for 5h;

20 g of [502161-03-7]3-iodo-9-phenylcarbazole was reacted with 10 g of aniline at a temperature of 165C in a solvent of mesitylene for five hours in the presence of 35 g of potassium carbonate and 10 g of copper powder. After completion of the reaction, the resulting reaction mixture was dissolved in toluene, the resulting solution was filtered to remove inorganic materials therefrom, and the resultant was subjected to fractionation by silica gel column chromatography using a mixed solvent composed of toluene/hexane as eluent to separate the desired compound. The obtained solid was recrystallized from hexane to provide 12.3 g of phenyl-9-phenyl-3-carbazolylamine (2) as white solid.

Reference： [1]Patent: US2013/112948,2013,A1 .Location in patent: Paragraph 0125; 0126
[2]Patent: KR2016/27561,2016,A .Location in patent: Paragraph 0329-0331
[3]Patent: EP1921082,2008,A1 .Location in patent: Page/Page column 33
[4]Patent: EP2100880,2009,A1 .Location in patent: Page/Page column 14-15

13
[ 121-43-7 ]
[ 502161-03-7 ]
[ 854952-58-2 ]

Yield	Reaction Conditions	Operation in experiment
76%		400 g of THF and 9.6 g (0.395 mol) of magnesium were placed and the internal temperature was maintained at 75 to 80 . 300 g of THF was added to 146 g (0.395 mol) of Intermediate Compound H and completely dissolved, After the internal temperature is maintained at 75 to 80 C, it is slowly added dropwise to the reactor prepared in advance.The reaction was carried out with stirring for 12 hours.After completion of the reaction,Cooled to -20 or lower,62 g (0.5966 mol) of trimethyl borate was slowly added dropwise, and the reaction was allowed to proceed at 0 for 5 hours.82.27 g (0.79 mol) of hydrochloric acid was slowly added dropwise at 0 C or lower, stirred at room temperature for 2 hours, and concentrated under reduced pressure to remove THF.300 g of toluene and 100 g of water were added. The organic layer was separated and concentrated under reduced pressure to remove toluene. 150 g of heptane was added thereto, and the mixture was refluxed, cooled and dried to obtain 86 g of intermediate I (yield: 76%) having a purity of 98.9%.
76%		9.6 g (0.395 mol) of magnesium and 400 g of THF were added and the internal temperature was maintained at 75 to 80C .300 g of THF was added to 146 g (0.395 mol) of Intermediate H and completely dissolved. Then, the mixture was slowly dropped to the previously prepared reactor while maintaining the internal temperature at 75 to 80C , and the mixture was reacted for 12 hours with stirring.After the reaction, the mixture was cooled to -20 or lower and 62 g (0.5966 mole) of trimethylborate was slowly added dropwise.After reacting for 5 hours at 0C, 82.27 g (0.79 mol) of hydrochloric acid was slowly added dropwise at 0C or lower, stirred at room temperature for 2 hours, and then concentrated under reduced pressure to remove THF.300 g of toluene and 100 g of water were added. The organic layer was separated and concentrated under reduced pressure to remove toluene. 150 g of heptane was added, and the mixture was refluxed, cooled and dried to obtain 86 g (yield: 76%) of intermediate I having a purity of 98.9%.
51%		Synthesis of Intermediate G; Intermediate F (2.71 g, 7.34 mmol) was added to THF (50 ml), and n-butyllithium (2.5M in hexane) (3.9 ml, 9.55 mmol) was dropwise added thereto at -78 C. The reaction mixture was stirred for one hour, and trimethylborate (2.5 ml, 22.0 mmol) was added thereto. The reaction solution was heated to room temperature, stirred for one hour, and hydrolyzed with a 2N HCl solution. An aqueous layer was extracted three times with ethylacetate (20 ml). The collected organic layer was dried over magnesium sulfate to evaporate a solvent. The resultant residue was purified by silica gel column chromatography to give intermediate G as a white solid (1.07 g, yield: 51%). The structure of intermediate G was determined by 1H NMR. 1H NMR (CDCl3, 300 MHz) delta (ppm) 8.11 (d, 2H), 8.09 (s, 2H), 7.67 (d, 2H), 7.52-7.47 (m, 4H), 7.38-7.31 (m, 4H); 13C NMR (CDCl3, 100 MHz) delta (ppm) 143.2, 140.3, 137.6, 131.2, 130.6, 129.8, 129.5, 128.4, 127.4, 127.1, 126.3, 124.8, 119.2, 119.0, 109.6, 99.6, 95.3, 90.5.

Reference： [1]Patent: KR2016/19744,2016,A .Location in patent: Paragraph 0058; 0063; 0064; 0079; 0084; 0085
[2]Patent: KR2016/19745,2016,A .Location in patent: Paragraph 0047; 0053-0054
[3]Patent: US2008/174237,2008,A1 .Location in patent: Page/Page column 13-14

14
[ 5467-74-3 ]
[ 502161-03-7 ]
[ 1028647-93-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 65℃; for 7h;	<strong>[502161-03-7]3-iodo-9-phenyl-9H-carbazole</strong>(5g) and (4-bromophenyl)boronic acid (2.7g), tetrahydrofuran (50ml) and water (25ml) and then dissolved in a potassium carbonate ( 5.6g), Pd (PPh3)4into the (780mg) was 7 hours at 65 degrees.After cooling the reaction mixture slowly to room temperature and then extracted with ethyl acetate and dried over anhydrous magnesium sulfate, separating the residue obtained by filtration under reduced pressure was purified by silica gel chromatography tube chromatographic purification Intermediate 100-4 (4.1g, yield: 76%) obtained.
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 65℃; for 7h;	5 g of <strong>[502161-03-7]3-iodo-9-phenyl-9H-carbazole</strong> and 2.7 g of 4-bromophenylboronic acid were dissolved in a solvent mixture comprising 50 mL of tetrahydrofuran and 25 mL of water,And 5.6 g of potassium carbonate and 780 mg of Pd (PPh3) 4 were added thereto.The reaction solution was allowed to react at a temperature of 65 C for 7 hours.The resulting reaction solution was cooled to room temperature,The organic layer was extracted therefrom by using ethyl acetate.The organic layer thus collected was dried over anhydrous magnesium sulfate,And the residue obtained after filtration under reduced pressure was separated and purified by silica gel column chromatography,To obtain 4.1 g of intermediate I-13 (yield: 76%).The compounds thus produced were determined by using LC-MS.
49%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 9.5h;	Step 1: Synthesis of 3-(4-bromophenyl)-9-phenyl-9H-carbazole][0449]A synthetic scheme of 3-(4-bromophenyl)-9-phenyl-9/-f-carbazole in Step 1 is shown in the following (J-I). [0450][0451]In a 200-mL three-neck flask, 3.7 g (9.9 mmol) of 3-iodo-9-phenyl-9i¥-carbazole, 2.0 g (9.9 mmol) of 4-bromo phenylboronic acid, and 0.61 g (2.0 mmol) of tri(°-tolyl)phosphine were put, and 50 mL of ethylene glycol <n="186"/>loodimethyl ether (abbreviation: DME) and 10 mL of a potassium carbonate solution (2 mol/L) were added to this mixture. This mixture was deaerated while being stirred under low pressure, and the atmosphere in the flask was substituted by nitrogen after the deaeration. [0452]Then, 0.11 g (0.50 mmol) of palladium(II) acetate was added to this mixture. This mixture was stirred at 80 0C for 9.5 hours. After the stirring, this mixture was cooled to room temperature and then washed twice with water. The obtained aqueous layer was extracted twice with toluene. Then, the extracted solution was combined with an organic layer, followed by washing with a saturated saline solution. The organic layer was dried with magnesium sulfate, this mixture was naturally filtrated, and then the filtrate was concentrated. [0453]The obtained oily substance was dissolved in about 20 mL of toluene, and suction filtration was performed on this solution through Celite, alumina, and then Florisil. A solid which was obtained by concentrating the obtained filtrate was purified by silica gel column chromatography (developing solvent, toluene: hexane = 1:4) to obtain 1.9 g of an objective white powder-like solid at a yield of 49 %.

49%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; water; at 80℃; for 9.5h;Inert atmosphere;	Step 4: Synthesis of 3-(4-bromophenyl)-9-phenyl-9H-carbazole To a 200-mL three-neck flask were added 3.7 g (9.9 mmol) of <strong>[502161-03-7]3-iodo-9-phenyl-9H-carbazole</strong>, 2.0 g (9.9 mmol) of 4-bromophenylboronic acid, and 0.61 g (2.0 mmol) of tri(o-tolyl)phosphine, which was followed by addition of 50 mL of 1,2-dimethoxyethane (abbreviated to DME) and 10 mL of an aqueous solution of potassium carbonate (2.0 mol/L). This mixture was degassed while being stirred under reduced pressure, and the atmosphere in the flask was substituted with nitrogen. Then, 0.11 g (0.50 mmol) of palladium(II) acetate was added to this mixture, which was then stirred at 80 C. for 9.5 hours. After the reaction, this mixture was cooled to room temperature and then washed twice with water. The organic layer was separated from the aqueous layer, and the resulting aqueous layer was extracted twice with toluene. Then, the extract was combined with the organic layer, followed by washing with brine. The combined organic layer was dried with magnesium sulfate, and subjected to the gravity filtration, and then the filtrate was concentrated. The resulting oily product was dissolved in ca. 20 mL of toluene, and the solution was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid which was obtained by concentrating the obtained filtrate was purified by silica gel column chromatography (developing solvent, toluene:hexane=1:4) to obtain 1.9 g of a white powder which was a target substance in a yield of 49%. A synthetic scheme of 3-(4-bromophenyl)-9-phenyl-9H-carbazole is shown in the following reaction scheme (A-4). Alternatively, 3-(4-bromophenyl)-9-phenyl-9H-carbazole can be synthesised in the method shown below.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux;	Blending 21.8 g of Intermediate 1, 11.8 g of 4-bromophenyl boronic acid, 1.38 g of Pd(PPh3)4, 21.9 g of sodium carbonate, tap water and dimethoxyethane, the reaction was allowed to proceed under refluxing for 8 h. The resultant solution was cooled down and the reacted solution was filtered, and a water layer prepared by separating the filtered residue through acetone was extracted with dichloromethane. The collected filtrate was separated and adding acetone and dichloromethane, the resultant solution was further separated. A water layer prepared by separating the filtered residue through acetone was extracted with dichloromethane, and a collected organic layer was washed with water and condensed. Purifying the resultant crude product by means of a silicagel chromatography (hexane : dichloromethane =9 : 1), re-crystallized the resultant solid through toluene and methanol, vacuum dried to obtain 4.18 g of white solid, which was analyzed by FD-MS and identified as Intermediate 3.
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; for 4h;	Comparative Synthesis Example B: Synthesis of Compound B; Compound B was synthesized through Reaction Scheme 8 below: [Show Image] 5 g (13.5 mmol) of 3-iodin-9-phenylcarbazole and 2.2 g (10.8 mmol) of 4-bromophenyl boronic acid were dissolved in THF, Pd(PPh3)4 (2mol%) and then an aqueous solution of K2CO3 were added thereto, and the mixture was reacted for 4 hours at 80C. After the reaction, the mixture was extracted 3 times with 150 mL of dichloromethane, and then residues obtained by drying an acquired organic layer with magnesium sulfate and evaporating a solvent was separated and purified via a silica gel tube chromatography. 4.2 g (10.6 mmol) of the compound obtained as such and 2.2 g (12.7 mmol) of diphenylamine were dissolved in toluene, and 195 mg (0.22 mmol) of tris(dibenzylideneacetone)dipalladium: Pd2(dba)3 and 44 mg (0.22 mmol) of tri(t-butyl)phosphine were added thereto under a nitrogen atmosphere. Then, 3.24 g (31.92 mmol) of NaOtBu was added to the mixture, and stirred for 4 hours at 80 C. The mixture obtained as such was cooled down at room temperature, extracted 3 times with dichloromethane, and then residues obtained by drying an acquired organic layer with magnesium sulfate and evaporating a solvent was separated and purified via a silica gel tube chromatography, thereby obtaining Compound B (4.5 g, 85% yield). 1H NMR (300MHz, DMSO) delta 8.54 (1H), 7.95 (2H), 7.84-7.78 (2H), 7.66 (2H), 7.62-7.58 (4H), 7.46-7.31 (4H), 7.28-7.21 (5H), 7.06 (2H), 6.89-6.71 (2H), 6.67 (2H)

Reference： [1]Patent: KR2015/106501,2015,A .Location in patent: Paragraph 0286-0288
[2]Patent: CN106565689,2017,A .Location in patent: Paragraph 0395; 0396; 0397; 0398
[3]Patent: WO2009/72587,2009,A1 .Location in patent: Page/Page column 184-185
[4]Patent: US2010/99890,2010,A1 .Location in patent: Page/Page column 33
[5]Patent: EP2085382,2009,A1 .Location in patent: Page/Page column 39
[6]Patent: EP2371828,2011,A1 .Location in patent: Page/Page column 41-42

15
[ 502161-03-7 ]
[ 854952-58-2 ]

Yield	Reaction Conditions	Operation in experiment
		Under an atmospheric argon gas flow, dehydrated toluene and dehydrated ether were added to 13.1 g of Intermediate 1, and the resultant solution was cooled down to -45 C. Dripping 25 ml of n-butyllithium hexane solution (1.58 M), elevated the temperature up to -5 C while stirring for 1 h. Cooling down to -45 C again, after slowly dripping 25 ml of boronic acid triisopropyl ester, the reaction was allowed to proceed for 2 h. Returning to a room temperature, a 10 % dilute hydrochloric acid solution was added and stirred, and an organic layer was extracted. After washing with a saturated sodium chloride solution, it was dried over unhydrated sulfur trioxide magnesium, separated by filtration and condensed. Purifying the resultant solid by means of a silicagel chromatography (toluene), the solid was washed with n-hexane and vacuum dried to obtain 7.10 g of solid, which was analyzed by FD-MS and identified as Intermediate 2.
		Under a flow of argon, dehydrated toluene and dehydrated ether were added to Intermediate 1 (13.1 g), and the resulting mixture was cooled to -45 C. 25 mL of a hexane solution of n-butyllithium (1.58M) was dropped thereto, and the mixture was heated to -5 C. over an hour while stirring. After cooled to -45 C. again, 25 mL of boronic acid triisopropyl ester was dropped slowly, followed by reaction for 2 hours.After the resultant was returned to room temperature, a 10% diluted hydrochloric acid solution was added and the resulting mixture was stirred to extract an organic phase. After washed with saturated saline, the organic layer was dried with anhydrous magnesium sulfate. It was separated by filtration, followed by concentration. The solids obtained were purified by silica-gel chromatography (toluene) and the solids obtained were washed with n-hexane and dried under reduced pressure to obtain 7.10 g of solids. The solids were identified as Intermediate 2 by FD-MS analysis.
7.1 g		Under a flow of argon, dehydrated toluene and dehydrated ether were added to 13.1 g of Intermediate 1 and the mixture was cooled to -45 C. 25 mL of n-butyllithium hexane solution (1.58 M) was dropped to the mixture, the temperature of which was raised over 1 hour to -5 C. under stirring. The resultant mixture was cooled again to -45 C., and was reacted for 2 hours after 25 mL of boronic acid triisopropyl ester was slowly dropped thereto.After the mixture was allowed to be at a room temperature, 10% dilute hydrochloric solution was added and stirred therewith, and the resultant organic phase was extracted. After being washed with saturated saline, the organic phase was dried with anhydrous magnesium sulfate and subjected to separation and concentration. The solids obtained were purified with silica gel chromatography (with toluene), and the resultant was washed with n-hexane and dried under reduced pressure to obtain 7.10 g of solids. The solids were identified as Intermediate 2 by FD-MS analysis.

Reference： [1]Patent: EP2085382,2009,A1 .Location in patent: Page/Page column 39
[2]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 293 - 296
[3]Patent: US2012/273766,2012,A1 .Location in patent: Page/Page column 70
[4]Patent: EP2617712,2013,A1 .Location in patent: Paragraph 0158
[5]Patent: EP2690093,2014,A1

16
[ 62-53-3 ]
[ 502161-03-7 ]
[ 1202685-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; potassium carbonate; In 1,3,5-trimethyl-benzene; at 160℃; for 3h;	3-(9-phenylcarbazolyl)-3'-(6'-diphenylamino-9'-phenyl)-carbazolylphenylamine (L) was synthesised according to the following scheme. 5.5 g of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong> and 0.7 g of aniline were reacted at 160C for 3 hours in the presence of 3 g of copper powder and 10.5 g of potassium carbonate in mesitylene. Toluene was added to the resulting reaction mixture, and the resultant mixture was heated with stirring to dissolve the reaction product. The resulting solution was filtered to remove solid components therefrom.The solution was concentrated, and the obtained concentrate was dissolved in acetic acid. To the resulting solution were added 0.4 g of potassium iodide and 0.5 g of potassium iodate to carry out an iodination reaction. The resulting reaction mixture was neutralized with an aqueous solution of sodium thiosulfate, followed by separation and purification by using an alumina column, thereby 2.1 g of 3-(9-phenylcarbazolyl)-3'-(6'-iodo-9'-phenyl)carbazolylphenylamine (13) was obtained as pale yellow solid.

Reference： [1]Patent: EP2100880,2009,A1 .Location in patent: Page/Page column 23

17
[ 86-74-8 ]
[ 502161-03-7 ]
[ 1026033-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In xylene;	3-diphenylamino-6-(9'-(3',6'-bis(diphenylamino)carbazolyl)-9-phenylamine (E) was synthesised according to the following scheme. 10 g of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong> and 5 g of carbazole were reacted in xylene in the presence of 0.006 g of palladium acetate, 0.02g of tri-t-butylphosphine and 3.5 g of sodium t-butoxide. The resulting reaction mixture was extracted with water/toluene, and the resulting organic layer was dropwise added into ethanol to provide 3-(9-carbazolyl)-9-phenylcarbazole as white solid.

Reference： [1]Patent: EP2100880,2009,A1 .Location in patent: Page/Page column 19

18
[ 1679-18-1 ]
[ 502161-03-7 ]
[ 1026033-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water;	N,N'-diphenyl-N,N'-bis(4-(9-phenylcarbazolyl)phenyl) -1,4-diaminobenzene (K) was synthesised according to the following scheme. 5 g of p-chlorophenylboric acid and 7.9 g of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong> were subjected to Suzuki coupling reaction in a mixed solvent of tetrahydrofuran/water in the presence of 0.05 g of tetrakistriphenylphosphine palladium and 8.8 g of potassium carbonate. After completion of the reaction, the resulting reaction mixture was extracted with toluene to obtain organic material. The organic material was crystallized from xylene twice, thereby providing 3-(4-chlorophenyl)-9-phenylcarbazole (12).

Reference： [1]Patent: EP2100880,2009,A1 .Location in patent: Page/Page column 23

19
[ 101-54-2 ]
[ 502161-03-7 ]
[ 1026033-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; potassium carbonate; In 1,3,5-trimethyl-benzene; for 18h;Reflux;	15.6 g of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>, 4.9 g of N-phenyl-1,4-diaminobenzene, 22.4 g of potassium carbonate and 10 g of copper powder were added to mesitylene, and were reacted for 18 hours under reflux. The resulting reaction mixture was dropwise added into ethanol to provide orange solid. The solid was adsorbed onto silica gel and charged in a column, followed by eluting with a mixed solvent of toluene/hexane, thereby a fraction containing the desired product was obtained. The fraction was concentrated and subjected to crystallization from toluene/xylene, followed by purification by sublimation to provide 2.3 g of N,N,N'-tris(9-phenyl-3-carbazolyl)-N'-phenyl-1,4-diaminobenzene (I). The molecular weight (M+ (m/e)) measured by mass analysis and the results of elemental analysis are shown in Table 1. The ionization potential, the glass transition temperature measured by differential scanning calorimetric analysis (DSC), the decomposition temperature measured by thermogravimetric measurement/differential calorimetry (TG/DTA), and the oxidation potential (vs Ag/Ag+) measured by cyclic voltammetry (CV) are shown in Table 2. The DSC chart is shown in Fig. 22, the TG/DTA chart is shown in Fig. 23, the CV chart is shown in Fig. 24, and the infrared absorption spectrum (KBr tablet method) is shown in Fig. 25.

Reference： [1]Patent: EP2100880,2009,A1 .Location in patent: Page/Page column 21-22

20
[ 1213768-48-9 ]
[ 502161-03-7 ]
[ 1186644-43-8 ]