Name: 201731-79-5|2-Bromo-9,10-diphenylanthracene|98%
Brand: Ambeed
SKU: A464076
Price: 11.0 USD
Availability: InStock
Rating: 99 (25 reviews)

1
[ 860530-98-9 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hypophosphite; potassium iodide In acetic acid for 3h; Heating / reflux;
85%	With sodium hypophosphite hydrate; potassium iodide In acetic acid for 3h; Heating / reflux;	1.1-c; 4.4-c In an argon atmosphere, 4.5 g (10 mmol) of 2-bromo-9,10-diphenyl-9,9,10,10-tetrahydroanthracene-9,10-diol were dissolved into acetic acid, and 17 g (102 mmol) of potassium iodide and 18 g (167 mmol) of NaH2PO2 were added. The mixture was refluxed under heating while being vigorously stirred for 3 hours. The temperature of the mixture was cooled to room temperature, and then the mixture was filtered. The resultant solid was washed with water and methanol, and was then dried under reduced pressure to obtain 3.5 g of 2-bromo-9,10-diphenylanthracene (85% yield).
80%	With sodium hypophosphite; acetic acid; potassium iodide at 80 - 90℃; for 2h; Inert atmosphere;	1 synthesis of intermediate 2 2 opening having composite multi function cap 500 ml(1)(9.2g, 0.02mol), KI (12.4g, 0.07mol) NaH2PO2(12.4g, 0.14mol), AcOH (300 ml) together in a under nitrogen into the 80-90oC in the reflux time 2. After filtering solid after my phosphorus temperature is washing water. Solid is dibutyl phthalate or dimethyl MC Methylene Chloride and a distilled water by extracting with him. Extracted Methylene Chloride layer MgSO4after for holding a order to form an exterior, of methanol removing the solvent by the yellow solid obtained. The solid Column Chromatography method using a yellow solid(2) separated the. (6.8g, 80%)

80%	With NaH₂PO₂; acetic acid; potassium iodide at 80 - 90℃; for 2h; Reflux; Inert atmosphere;	1 Synthesis of intermediate (2) 2-necked 500ml flask was charged with compound (1) (9.2g, 0.02mol), KI (12.4g, 0.07mol) NaH2PO2 (12.4g, 0.14mol), 2 hr reflux insert as the AcOH (300ml) at 80 ~ 90oC under a nitrogen It was. Lower the temperature of the solid was washed with water and then filtered. Dissolve the solid in MC was extracted with distilled water and Methylene Chloride. After the extraction of the water japahjun Methylene Chloride layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a yellow solid. This solid was isolated using the Column Chromatography how the yellow solid (2). (6.8g, 80%)
80%	With sodium hypophosphite; acetic acid; potassium iodide at 80 - 90℃; for 2h; Inert atmosphere;	1 Synthesis of intermediate 2 2-necked 500ml flask was charged with compound (1) (9.2g, 0.02mol), KI (12.4g, 0.07mol) NaH2PO2 (12.4g, 0.14mol), 2 hr reflux insert as the AcOH (300ml) at 80-90°C under a nitrogen It was. Lower the temperature of the solid was washed with water and then filtered. Dissolve the solid in MC was extracted with distilled water and Methylene Chloride. After the extraction of the water japahjun Methylene Chloride layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a yellow solid. Using the method ColumnChromatography This solid was isolated yellow solid (2). (6.8g, 80%)
74%	Stage #1: 2-bromo-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol With sodium hypophosphite; acetic acid; potassium iodide at 120℃; for 2h; Stage #2: With hypophosphorous acid In water at 120℃; for 1h;	1.1.iii A synthetic scheme of 2-bromo-9,10-diphenylanthracene is shown in (C-3).; [0280][0281] 7.55 g (16.95 mmol) of the obtained2-bromo-9,10-diphenyl-9,10rdihydroanthracene-9,10-diol, 5.06 g (30.51 mmol) of potassium iodide, 9.70 g (91.52 mmol) of sodium phosphinate monohydrate, and 50 niL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was heated at 120 °C for 2 hours. Thereafter, 30 mL of 50% phosp'hinic acid was added to the mixture, and the mixture was stirred for 1 hour at 120 0C. After the reaction, the mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in toluene, and the solution was filtered through celite, Florisil, and then alumina. The filtrate was concentrated, and the residue was recrystallized with chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene as a light yellow solid in 74% yield.
	With acetic acid; potassium iodide
	Stage #1: 2-bromo-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol With sodium hypophosphite monohydrate; acetic acid; potassium iodide at 120℃; for 2h; Stage #2: With hypophosphorous acid at 120℃; for 1h;	1.2 All of the obtained 2-bromo-9,10-diphenylanthracene-9,10-diol, 5.06 g (30.5 mmol) of potassium iodide, 9.70 g (91.5 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was stirred at 120° C. for 2 hours. After the stirring, 30 mL of 50% phosphinic acid was added to the mixture, and the mixture was further stirred for 1 hour at 120° C. After the stirring, the solution was washed with water, and an aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate, subjected by gravity filtration, and then the obtained filtrate was concentrated to obtain a light-yellow solid substance. The solid substance was dissolved in toluene, and the solution was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina. The obtained filtrate was concentrated to obtain a solid substance and the solid substance was then recrystallized with chloroform/hexane; thus, 5.1 g of 2-bromo-9,10-diphenylanthracene as a light-yellow powdered solid substance, which was the object of the synthesis, was obtained in 74% yield. The synthesis scheme of Step 2 is shown in (a-2). In this manner, 2-bromo-9,10-diphenylanthracene, which is the material, was obtained. Next, the synthesis method for forming 9-(9,10-diphenyl-2-anthryl)-9H-carbazole (abbreviation: 2CzPA), which is the anthracene derivative of Embodiment 1, is described.
	Stage #1: 2-bromo-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol With sodium hypophosphite monohydrate; potassium iodide In acetic acid at 120℃; for 2h; Stage #2: With hypophosphorous acid In acetic acid at 120℃; for 1h;	1.1.iii; C.3 A synthesis scheme of 2-bromo-9,10-diphenylanthracene is illustrated in (C-3). [0351] [0352]In a 500 mL three-neck flask were put 7.55 g (17.0 mmol) of 2-bromo-9,10-dihydroanthracene-9,10-diol, which was obtained, 5.06 g (30.5 mmol) of potassium iodide, 9.70 g (91.5 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid, and this mixture was stirred at 120 °C for 2 hours. Then, to this mixture was added 30 mL of 50 % phosphinic acid, and this mixture was further stirred at 120 0C for 1 hour. Then, this solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract solution and the organic layer were combined and dried with magnesium sulfate. This mixture was gravity filtered. The obtained filtrate was concentrated to give a light yellow solid. The obtained solid was dissolved in toluene, and this solution was suction filtered through Celite (a product of Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (a product of Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina. The obtained filtrate was concentrated to give a solid. The solid was recrystallized with chloroform/hexane to give the object of the synthesis as 5.1 g of a light yellow powdered solid in a yield of 74 % (which is the yield of the schemes (C-2) and (C-3)).
	With acetic acid; potassium iodide for 18h; Reflux;	1 Preparation of Compound (113)A reaction vessel was charged with Compound (112) (5.7 g, 12.9 mmol), potassium iodide (8.5 g, 51.4 mmol) and sodium hydrophosphate hydrate (NaHPO2H2O) (8.2 g, 77.2 mmol). Glacial acetic acid (50 mL) was added thereto in order to dissolve the content of the vessel, and the solution was stirred under reflux. After 18 hours of stirring, the reaction mixture was cooled to 25° C., and distilled water (400 mL) was added thereto. The solid produced was filtered and washed with excess amount of water. Washing with aqueous sodium hydroxide solution (100 mL) and recrystallization from n-hexane (300 mL) gave Compound (113) (4.2 g, 10.3 mmol).
	With sodium hypophosphite; acetic acid; potassium iodide for 3h; Reflux;	1.1-2 1-2) Synthesis of 2-bromo-9,10-diphenylanthracene 164 g (1.045 mol) of bromobenzene was loaded into a 2 L reactor, and then 700 ml of THF was added thereto. The temperature of the reactor was lowered to - 78°C, and then 653.06 ml (1.045 mol) of 1.6M n-BuLi was slowly added dropwise thereto. Then, the mixture was stirred for about one hour at low temperature and then, 100 g (0.348 mol) of 2-bromoanthraquinone obtained from 1-1) was added thereto. The resultant mixture was reacted at room temperature for 6 hours and then 200 ml of 2N HCl was added thereto. The reaction mixture was subjected to layer isolation and an organic solvent included in an organic layer was removed under reduced pressure, thereby obtaining intermediate A. Intermediate A, 173.45 g (1.045 mol) of KI, 221.50 g (2.090 mol) of sodium hyphophousfite, and 1000 ml of AcOH were added to a 2 L reactor and refluxed for 3 hours. The resultant product was cooled to room temperature, thereby producing a solid. The solid was filtered and washed with methanol and water, and then, re-crystallized with toluene, thereby producing a brown solid (105 g, 73%).
	Stage #1: 2-bromo-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol With sodium hypophosphite monohydrate; acetic acid; potassium iodide at 120℃; for 2h; Stage #2: With hypophosphorous acid at 120℃; for 1h;	1.1.iii About 7.6 g (17 mmol) of the obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 5.1 g (31 mmol) of potassium iodide, 9.7 g (92 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was refluxed at 120° C. for two hours. Thereafter, 30 mL of 50% phosphinic acid was added to the reactive mixture, and the mixture was stirred for one hour at 120° C. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate, filtered by suction filtration and the obtained filtrate was concentrated to obtain a solid substance. The solid substance was dissolved in toluene, and the solution was filtered through Celite (manufactured by Celite Co., Ltd.), Florisil (manufactured by Floridin Company), and alumina. The obtained filtrate was concentrated to obtain a solid substance, and the solid substance was recrystallized with a mixed solvent of chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene as a light yellow powdered solid substance. The yield of the two stages (ii) and (iii) was 74%.
40 g	With sodium hypophosphite monohydrate; acetic acid; potassium iodide for 3h; Reflux;	4.4-1 Synthesis Example 4-(1): Synthesis of 2-bromo-9,10-diphenylanthracene While stirring the 2L round bottom flask, 164.1 g (1.045 mol) and 700 ml (THF) of bromobenzene were added.After the temperature was dropped to -78 ° C, 227.5 ml (1.045 mol) of n-BuLi was slowly added dropwise. After the dropwise addition, stir for 1 hour and 30 minutes,100 g (0.348 mol) of 2-bromoanthraquinone was dissolved in 300 ml of THF and rapidly added.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day.When the reaction was completed, 200 ml of 2N hydrochloric acid was added to make it acidic, and concentrated. The concentrated reactant was placed in a 2 L round bottom flask, KI 173.45 g (1.045 mol), NaH2PO2H2O 221.50 g (2.090 mol),It was refluxed with 1000 ml of acetic acid for 3 hours. When the reaction is finished, it is lowered to room temperature,The resulting solid is filtered and washed with methanol,Recrystallized from toluene. As a result, 40.0 g (0.097 mol, yield 27.94%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - WO2006/67931, 2006, A1 Location in patent: Page/Page column 54
[2]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1734038, 2006, A1 Location in patent: Page/Page column 42; 46
[3]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0088; 0089; 0090; 0093; 0094
[4]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0088-0089; 0093-0094
[5]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0090; 0093-0094
[6]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 131-132
[7]Velluz; Velluz [Bulletin de la Societe Chimique de France, 1938, vol. <5> 5, p. 192,194]
[8]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/253916, 2009, A1 Location in patent: Page/Page column 27
[9]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2009/131199, 2009, A1 Location in patent: Page/Page column 131-132
[10]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 6
[11]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292604, 2011, A2 Location in patent: Page/Page column 22
[12]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2 Location in patent: Page/Page column 151
[13]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0185-0189

2
[ 19606-98-5 ]
[ 201731-79-5 ]
9,10-diphenyl-2-[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 80℃; for 6h;	[Step 2] Synthetic method of 2DPAPA.A synthetic scheme of 2DPAPAiS shown in (C-4). [0283] <n="135"/>(C-4) [0284] . . ;1.8 g (4.40 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 ofEmbodiment 1, 1.78 g (5.28 mmol) of iVJiV^Vri-triphenyl-i,4-pheϖylenediamiiie (DPA), 0.126 g (0.220 mmol) of bis(dibenzylideneacetone)palladium (0), and 2.11 g (21.99 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere in the flask was substituted with nitrogen. Further, 30 mL of toluene and0.44 g (0.220 mmol) of tri(fert-butyl)phosphine (a 10% hexane solution) were added to the flask, and the solution was heated at 80 0C for 6 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate.The organic layer was dried over magnesium sulfate, filtered and concentrated, and the residue was dissolved in toluene, which was followed by filtration through celite, Florisil, and then alumina. The filtrate was concentrated, and then the residue was recrystallized with chloroform, methanol, and hexane, resulting in 2.24 g of the target compound as a yellow solid in 77% yield. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was9,10-diphenyl-2-[iV-(4-diphenylaminophenyl)-iV-phenylamino]anthracene (abbreviation:2DPAPA). [0285]1H NMR data of 2DPAPA is shown below. 1H NMR (DMSO-J6, 300 MHz): δ = 6.90-7.14 (m, 15H), 7.25-7.37 (m, 10H), 7.44-7.52 (m, 8H), 7.57-7.66 (m, 3H). The 1H NMR chart is shown in FIGS. HA and HB. Note that the range of 6.5 ppm to 8.0 <n="136"/>ppm in FIG. 11 A is expanded and shown in FIG. HB. [

Reference： [1]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 132-134

3
[ 894791-43-6 ]
[ 201731-79-5 ]
9,10-diphenyl-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium t-butanolate In hexane; toluene at 80℃; for 6h;	2.2 A synthetic scheme of 2PCAPA is shown in (C-7); [0300](C-7)[0301]1.8 g (4.40 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Embodiment 1, 1.76 g (5.28 mmol) of -V-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA), 0.126 g (0.220 mmol) of bis(dibenzylideneacetone)palladium (0), and 2.11 g (21.99 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere in the flask was substituted with nitrogen. 30 mL of toluene and 0.44 g (0.220 mmol) of tri(tert-butyl)phosphine (10% hexane solution) were added to the flask, and the mixture was heated at 80 0C with stirring for 6 hours. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. After filtration and concentration of the organic layer, the residue was dissolved in toluene, and the solution was filtered through celite, Florisil, and then alumina. The filtrate was concentrated, and the. residue was recrystallized with chloroform, methanol, and hexane, obtaining 2.33 g of the target compound as a yellow solid in 80% yield. By the nuclear magnetic resonance analysis (NMR), it was confirmed that this compound was 9,10-diphenyl-2-[iST-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene (abbreviation: 2PCAPA). [0302]1H NMR data of this compound is shown below. 1H NMR (CDCl3, 300 MHz): δ = 6.92-6.97 (m, IH), 7.11-7.32 (m, 16H), 7.39-7.66 (m, 15H), 7.88-7.97 (m, 2H). Also, the 1H NMR chart is shown in FIGS. 17A and 17B. Note that the range of 6.5 ppm to 8.0 ppm in FIG. 17A is expanded and shown in FIG. 17B. [0303]The decomposition temperature (Td) of 2PCAPA, measured with a thermogravimetric/differential thermal analyzer (type TG/DTA 320, manufactured by Seiko Instruments Inc.), was found to be 410.1 0C, meaning high thermal stability of this compound.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 137-139

4
[ 894791-44-7 ]
[ 201731-79-5 ]
2-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium t-butanolate In hexane; toluene at 80℃; for 5h;	7.2 [Step 2] Synthesis of 2PCNPA.; A synthetic scheme of 2PCNPAis shown in (C-17). [0386](°-17)[0387]3.5 g (8.6 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Embodiment 1, 3.2 g (9.4 mmol) of iV-(l-naphthyl)-iV-(9-phenylcarbazol-3-yl)amine (abbreviation: PCN), 0.25 g (0.43 mmol) of bis(benzylideneacetone)palladium (0), and 2.1 g (21 mmol) of sodium fert-butoxide were put in a 200 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Thereafter, 50 mL of toluene and 0.86 g (0.43 mmol) of tri(teτt-butyi)phosphine (10% hexane solution) were added to the mixture, and this reaction mixture was stirred for 5 hours at 80 0C. After the reaction was completed, the reaction solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted solution was combined with the organic layer, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent : toluene). The obtained solid was recrystallized with a mixed solvent of chloroform and hexane, giving 2.6 g of 2-[N-(l-naphthyl)-iV-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene(abbreviation: 2PCNPA) as yellow powder in 42% yield. It was confirmed by a nuclear magnetic resonance measurement (NMR) that this compound was 2-[JV-(l-naphthyl)-iV-(9-phenylcarbazol-3-yl)-amino]-9,10-diphenylanthracene (abbreviation: 2PCNPA). [0388] 1H NMR data of this compound is shown below. 1H NMR (CDCl3, 300 MHz): δ = 6.67-6.68 (m, IH), 7.02-7.38 (m, 15H), 7.44-7.70 (m, 16H), 7.88-8.01 (m, 4H). The 1H NMR chart is shown in each of FIGS. 9OA and 9OB. Note that the range of 6.5 ppm to 8.5 ppm in FIG. 9OA was expanded and shown in FIG. 9OB.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 164-165

5
[ 955123-57-6 ]
[ 201731-79-5 ]
2-{N-(1-naphthyl)-N-[9-(1-naphthyl)carbazol-3-yl]amino}-9,10-diphenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium t-butanolate In hexane; xylene at 110℃; for 4h;	8.2 A synthetic scheme of 2NCNPAiS shown in (C-21). [0410](C-21)[0411]2.1 g (5.0 mmol) of 2-bromo-9,10-diphenylanthracene, 2.2 g (5.1 mmol) of NCN, 29 g (50 μmol) of bis(dibenzylideneacetone)palladium (0), 300 μL (0.2 mmol) of tri(ter/-butyl)phosphine (10% hexane solution), and 1.0 g (10 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and nitrogen substitution was carried out in the flask. Thereafter, 20 mL of dehydrated xylene was added to this mixture. Then, this reaction mixture was heated and stirred for 4 hours at 110 °C under nitrogen. After the reaction was completed, about 300 mL of toluene was added to this reaction mixture, and this mixture was filtered through Florisil, alumina, and then celite. After the obtained filtrate was washed with water, the organic layer was dried with magnesium sulfate. This suspension was filtered through Florisil, alumina, and then celite, and the resulting filtrate was concentrated. The obtained solid was purified by silica gel column chromatography (toluene:hexane=l:l). To the oily residue obtained was added hexane, and the mixture was then irradiated with ultrasound to precipitate a solid. This solid was collected by suction filtration, giving 1.1 g of the target compound as yellow-green powder (29% yield). It was confirmed by a nuclear magnetic resonance measurement (NMR) that this yellow-green powder ' was 2-{N-(l-naphthyl)-iV-[9-(l-naphthyl)carbazol-3-yl]amino}-9,10-diphenylanthracene (abbreviation: 2NCNPA). [0412]1H NMR data of this compound is shown below. 1H NMR (300 MHz, CDCl3): 6 = 6.73 (d, J = 2.4 Hz, IH), 6.84 (d, J = 8.7 Hz, IH), 6.96 (d, J = 8.1 Hz, IH), 7.04-7.70 (m, 29H), 7.89 (d, J = 7.8 Hz, IH), 7.99-8.06 (m, 5H). The 1H NMR chart is shown in each of FIGS. 97A and 97B. Note that the range of 6.5 ppm to 8.5 ppm in FIG. 97A is expanded and shown in FIG. 97B. [0413] The absorption spectrum of a toluene solution of 2NCNPA is shown in FIG. 98.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 170-172

6
[ 858641-06-2 ]
[ 201731-79-5 ]
2-{N-[4-(carbazol-9-yl)phenyl]-N-phenylamino}-9,10-diphenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium t-butanolate In hexane; toluene at 80℃; for 5h;	11.1 [Embodiment 11] [0442] In this embodiment, a synthetic method ' of2-{iV-[4-(carbazol-9-yl)phenyl]-JV-phenylamino}-9,10-diphenylanthracene (abbreviation: 2YGAPA), which is the anthracene derivative of the present invention represented by Structural Formula (301), is specifically described. [0443][0444][Step 1] Synthetic method of 2YGAPA. A synthetic method of 2YGAPAis shown in (C-22). [0445](C-22)[0446]2.0 g (4.1 mmol) of 2-bromo-9,10-diphenylanthracene synthesized in Step 1 of Embodiment 1, 1.0 g (10 mmol) of sodium ter-butoxide, 1.4 g (4.1 mmol) of 4-(carbazol-9-yl)diphenylamine and 0.1 g (0.2 mmol) of bis(dibenzylideneacetone)palladium (0) were put into a 100 mL three-neck flask, and the inside of the flask was substituted with nitrogen. 30 mL of toluene and 0.1 mL of 10wt% hexane solution of tri(tert-butyl)phosphine were added to this mixture. Then, this mixture was heated and stirred for 5 hours at 80 0C. After the reaction, toluene was added to a reaction mixture, and this suspension was washed with a saturated sodium carbonate aqueous solution and then with brine. The aqueous layer and organic layer were separated, and the organic layer was subjected to suction filtration through Florisil, celite, and alumina, and the filtrate was obtained. The obtained filtrate was concentrated to give a solid. The obtained solid was recrystallized with a mixed solvent of chloroform and hexane, which provided 2.2 g of the target compound as a yellow solid in 81% yield. By the nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was2-{N-[4-(carbazol-9-yI)phenyl]-iv"-phenylamino}-9,10-diphenylanthracene (abbreviation: 2YGAPA). [0447]1H NMR data of 2YGAPA is shown below. 1H NMR (300 MHz, CDCl3): δ = 7.05-7.12 (m, IH), 7.13-7.74 (m, 31H), 8.16 (d, J = 6.8 Hz, 2H). The 1R NMR chart is shown in each of FIGS. 112A and 112B. Note that the range of 6.5 ppm to 8.5 ppm in FIG. 112A is expanded and shown in FIG. 112B.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 178-180

7
[ 167218-30-6 ]
[ 201731-79-5 ]
9,10-diphenyl-2-[N-(4'-diphenylamino-1,1'-biphenyl-4-yl)-N-phenylamino]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; toluene; at 100℃; for 3.0h;	[Step 3] Synthesis of 2DPBAPAA synthetic scheme of 2DPBAPAis shown in (C-34). [0495] <n="197"/>toluene 2DPBAPA(C-34) ; [0496]1.5 g (3.6 mmol) of 2-bromo-9,10-diphenylanthracene, 1.5 g (3.6 mmol) of N^V'^'-triphenylbenzidine (abbreviation: DPAB), and 1.5 g (16 mmol) of sodium terf-butoxide were put into a 100 mL three-neck flask, and the inside of the flask was substituted with nitrogen. 20 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (10wt% hexane solution) were added to this mixture. After this mixture was degassed under reduced pressure while being stirred, 41 mg (0.072 mmol) of bis(dibenzylideneacetone)palladium (0) was added. Then, the mixture was stirred for 3 hours at 100 0C. After about 50 mL of toluene was added to the reaction mixture, this mixture was subjected to suction filtration through celite, Florisil, and alumina. The obtained filtrate was concentrated, yielding oily compound. About 10 mL of toluene was added to this oily compound, which was left for about 2 hours to afford a yellow solid as a precipitate. Suction filtration of this precipitate gave 2.5 g of the target compound as yellow powder in 91% yield. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was <n="198"/>9,10-diphenyl-2- [JV(4'-diphenylamino- 1,1' -biphenyl-4-yl)-N-phenylamino] anthracene(abbreviation: 2DPBAPA).[0497]1H NMR data of this compound is shown below. 1H NMR (300 MHz, DMSO-J6): delta = 7.01-7.08 (m, HH)5 7.13-7.17 (m, 5H), 7.22-7.89 (m, 12H), 7.42-7.66 (m, 12H). The 1H NMR chart is shown in each of FIGS. 120A and 120B. Note that the range of 6.5 ppm to 8.5 ppm in FIG. 120A is expanded and shown in FIG. 120B

Reference： [1]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 194-196

8
[ 331980-55-3 ]
[ 201731-79-5 ]
2-{N-[4'-(9H-carbazol-9-yl)-1,1'-biphenyl-4-yl]-N-phenylamino}-9,10-diphenylanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With sodium t-butanolate In hexane; toluene at 100℃; for 3h;	15.3 [Step 3] Synthesis of 2YGBAPA.A synthetic scheme of 2YGBAPAis shown in (C-37).; [0508]toluene (C-37) [0509]1.2 g (3.0 mmol) of 2-bromo-9,10-diphenylanthracene, 1.2 g (3.0 mmol) of YGBA, and 1.5 g (16 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the inside of the flask was charged with nitrogen. 15 mL of toluene and 0.20 mL of tri(tert-butyl)phosphine (10wt% hexane solution) were added to this mixture. This mixture was degassed under reduced pressure while being stirred, and 86 mg (0.15 mmol) of bis(dibenzylideneacetone)palladium (0) was added. Thereafter, this mixture was stirred for 3 hours at 100 0C. This mixture was subjected to suction filtration through celite, alumina, and Florisil. An oily compound obtained by concentrating the obtained filtrate was purified by silica gel column chromatography (eluent was hexane:toluene=7:3), and the resulting yellow solid was recrystallized with chloroform/methanol, giving 462 g of the target compound as a, yellow solid in 21% yield. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was2-{iV-[4'-(9H-carbazol-9-yl)-l,l'-biphenyl-4-yl]-iV-phenylam.ino}-9,10-diphenylanthrac ene (abbreviation: 2YGBAPA). [0510]1H NMR data of this compound is shown below. 1H NMR (300 MHz, DMSOd6): δ = 7.08-7.14 (m, 5H), 7.20 (dd, J =2.4, 9.5 Hz, IH), 7;28-7.61 (m, 22H), 7.64 (d, J = 7.2 Hz, 2H), 7.70 (dd, J =2.4, 7.7 Hz, 4H), 7.91 (d, J = 8.4 Hz, 2H), 8.26 (d, J = 7.8 Hz, 2H). The 1H NMR chart is shown in each of FIGS. 123A and 123B. Note that the range of 6.5 ppm to 9.0 ppm in FIG. 123Ais expanded and shown in FIG. 123B.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 199-200

9
[ 474687-82-6 ]
[ 201731-79-5 ]
C₆₄H₄₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium phosphate In DMF (N,N-dimethyl-formamide) at 90℃; for 60.5h;	15 To a suspension of 2-bromo-9,10-diphenylanthracene (0.41 g, 1.00 mmol), Chemical Compound 8 (0.79 g, 1.50 mmol), and potassium phosphate (0.64 g, 3.00 mmol)) in DMF (15 ml) was added tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) under nitrogen. The mixture was degassed with nitrogen for 30 minutes. After the reaction mixture had been stirred at 90° C. for 60 hours, it was cooled to room temperature and ethanol (60 ml) was added. After addition, the reaction mixture was stirred at room temperature for 30 minutes. The precipitate was filtered off with suction, washed with water and ethanol, and dried under vacuum. Purification by sublimation afforded Chemical Compound 116 (0.32 g, 40%) as white solid: mp 399.06° C.; 1H NMR (500 MHz, CDCl3) δ 7.90 (dd, J=7.0, 13.0 Hz, 4H), 7.62-7.37 (m, 19H), 7.31-7.22 (m, 9H), 7.05 (dd, J=2.0, 8.0 Hz, 1H), 6.96 (dd, J=2.0, 8.0 Hz, 1H), 6.79-6.75 (m, 2H), 6.56 (d, J=2.0 Hz, 1H), 6.41-6.36 (m, 3H); MS (M+) Calculated for C64H40 808. found 808. analysis calculated for C64H40: C, 95.02; H, 4.98. Found: C, 95.10; H, 4.90.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US6998487, 2006, B2 Location in patent: Page/Page column 51

10
[ 1679-18-1 ]
[ 201731-79-5 ]
[ 867044-31-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium carbonate In 1,2-dimethoxyethane; water for 8h; Heating / reflux;	9.9-d 5.0 g (8.5 mmol) of 2-bromo-9,10-diphenylanthracene, 2.9 g (18.7 mmol) of 4-chlorophenylboronic acid, and 0.20 g (0.17 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 50 mL of 1,2-dimethoxyethane. Then, 25 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. The resultant was stood to cool. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 4.8 g of 2,6-bis(4-chlorophenyl)-9,10-di(2-naphthyl)anthracene (86% yield).

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1734038, 2006, A1 Location in patent: Page/Page column 48

11
[ 201731-79-5 ]
[ 597553-98-5 ]

Yield	Reaction Conditions	Operation in experiment
80%		In an argon atmosphere, 50 mL of dehydrated THF were added to 3.5 g (8.6 mmol) of 2-bromo-9,10-diphenylanthracene, and the temperature of the mixture was cooled to -78 C. Then, 6.0 mL of n-butyllithium (in hexane, 1.6 mol/L) were dropped. After the mixture had been stirred at -78 C for 1 hour, the temperature of the mixture was increased to 0C. The temperature of the mixture was cooled to -78 C again, and 2. 9 mL (26 mmol) of trimethoxyborane were dropped. The mixture was stirred at -78 C for 1 hour, and was then stirred at room temperature for 2 hours. 50 mL of 10-mass% hydrochloric acid were added, and the whole was stirred for 1 hour, followed by filtration. The resultant solid was washed with toluene to obtain 2.6 g of 9,10-diphenylanthracene-2-boronic acid (80% yield).

Reference： [1]Patent: EP1734038,2006,A1 .Location in patent: Page/Page column 43; 46

12
[ 29786-93-4 ]
[ 108-86-1 ]
2H₂O [ No CAS ]
[ 124-38-9 ]
[ 572-83-8 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	With stannous chloride In tetrahydrofuran; acetic acid; acetone	1 Synthesis of 2-Bromo-9,10-diphenylanthracene Synthesis of 2-Bromo-9,10-diphenylanthracene 25 g (159 mmole) of bromobenzene was placed in an 500 ml round bottom flask, and was dissolved in dry THF. The solution was cooled down to -70° C. by dry ice/acetone, then 1.6M n-Butyl lithium 67 ml was added slowly over 30 minutes. The reaction was stirred for 2 hours while the reaction temperature was maintained at -70° C., 10 g (34.8 mmole) of 2-bromoanthraquinone (manufactured by Tokyo Chemical Industry Co., LTD.,) was added to the cooled reaction mixture, the reaction was stirred for overnight at room temperature. Then, 120 ml of 10% HCl(aq) was added to the resulting solution, and stirred for 30 minutes, the organic layer was separated, and was evaporated to dryness, the brown color residue was dissolved in 60 ml of acetic acid, and 29 g of SnCl2. 2H2O were added to the brown solution. The reaction mixture was heated to reflux for 6 hours, and then, cool down to room temperature. Thus, The brown product was collect be filtration, (6 g, 42.6%)

Reference： [1]Current Patent Assignee: Yen, Feng Wen - US2008/299294, 2008, A1

13
[ 201731-79-5 ]
[ 497-19-8 ]
[ 164461-18-1 ]
[ 1042668-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran	1 Synthesis of 2-pyrenyl-9,10-diphenylanthracene Synthesis of 2-pyrenyl-9,10-diphenylanthracene 2-bromo-9,10-diphenylanthracene (5 g 12 mmole) was placed into a 250 ml round bottom flask along with pyrene-1-boronic acid (4.5 g 18 mmole), THF 100 ml, and 2.0M aqueous sodium carbonate (18 ml). The reaction mixture was purged with nitrogen for 30 minutes and then Pd(PPh3)4(0.42 g) was added. The reaction was heated at reflux for 18 hours and then cooled down to room temperature. A yellow-green product was collected by filtration. The solid was wash with MeOH/H2O and dry in vacuum to get crude product. Further purification was achieved by sublimation (4.4 g, 67.7%). The product was identified through EI-MS measurement, m/s=530

Reference： [1]Current Patent Assignee: Yen, Feng Wen - US2008/299294, 2008, A1

14
[ 201731-79-5 ]
[ 1123921-69-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With n-butyllithium; nitrogen; sodium thiosulfate In tetrahydrofuran; methanol; iodine; ethyl acetate	1.i (i) (i) Synthesis of 2-iodo-9,10-diphenylanthracene Synthesis scheme of 2-iodo-9,10-diphenylanthracene is shown in (C-4) 10 g (24 mmol) of 2-bromo-9,10-diphenylanthracene was put in a 500 mL three neck flask, the atmosphere in the flask was substituted by nitrogen, and then 150 mL of tetrahydrofuran (THF) was added thereto and dissolved well. This solution was stirred at -78° C. Then, 19 mL of n-butyllithium solution (1.6 mmol/L) was dropped into this solution, with a syringe and stirred for one hour at -78° C., so that a white solid substance was precipitated. After reaction, a solution in which 12 g (49 mmol) of iodine was dissolved into 80 mL of tetrahydrofuran was dropped into this reacted mixture using a funnel for dropping. After dropping, the mixture was stirred for one hour at -78° C. and for 12 hours at room temperature. After reaction, a sodium thiosulfate solution was added into the reaction solution, and was stirred for one hour at room temperature. Ethyl acetate was added into this mixture for extraction. An aqueous layer and an organic layer were separated, and the organic layer was washed with sodium thiosulfate and saturated brine in this order. The aqueous layer and the organic layer were separated and the organic layer was dried with magnesium sulfate. This mixture was subjected to suction filtration so that the magnesium sulfate was removed. The obtained filtrate was concentrated, so that a solid substance was obtained. Methanol was added into this solid substance and washed by ultrasonic wave irradiation, so that a solid substance was precipitated. This solid substance was collected by suction filtration, so that 9.9 g of a light yellow powdered solid substance was obtained in a yield of 90%.
90%	Stage #1: 2-bromo-9,10-diphenylanthracene With n-butyllithium; sodium thiosulfate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78 - 20℃; for 13h; Stage #3: With sodium thiosulfate In tetrahydrofuran at 20℃; for 1h;	1.2.i 10 g (24 mmol) of 2-bromo-9,10-diphenylanthracene was put in a 500 mL three neck flask, the atmosphere in the flask was substituted by nitrogen, and then 150 mL of tetrahydrofuran (THF) was added thereto and dissolved well. This solution was stirred at -78° C. Then, 19 mL of n-butyllithium solution (1.6 mmol/L) was dropped into this solution, with a syringe and stirred for one hour at -78° C., so that a white solid substance was precipitated. After reaction, a solution in which 12 g (49 mmol) of iodine was dissolved into 80 mL of tetrahydrofuran was dropped into this reacted mixture using a funnel for dropping. After dropping, the mixture was stirred for one hour at -78° C. and for 12 hours at room temperature. After reaction, a sodium thiosulfate solution was added into the reaction solution, and was stirred for one hour at room temperature. Ethyl acetate was added into this mixture for extraction. An aqueous layer and an organic layer were separated, and the organic layer was washed with sodium thiosulfate and saturated brine in this order. The aqueous layer and the organic layer were separated and the organic layer was dried with magnesium sulfate. This mixture was subjected to suction filtration so that the magnesium sulfate was removed. The obtained filtrate was concentrated, so that a solid substance was obtained. Methanol was added into this solid substance and washed by ultrasonic wave irradiation, so that a solid substance was precipitated. This solid substance was collected by suction filtration, so that 9.9 g of a light yellow powdered solid substance was obtained in a yield of 90%.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/4506, 2009, A1
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2 Location in patent: Page/Page column 151-152

15
[ 201731-79-5 ]
[ 86-74-8 ]
[ 1190079-62-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium t-butanolate In hexane; toluene at 110℃; for 5h; Inert atmosphere;	1.3 Step 3: Synthesis of 9-(9,10-diphenyl-2-anthryl)-9H-carbazole (abbreviation: 2CzPA) First, 1.5 g (3.7 mmol) of 2-bromo-9,10-diphenylanthracene, which was obtained in Step 2, 610 mg (3.7 mmol) of 9H-carbazole, and 1.5 g (16 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere in the flask was substituted by nitrogen. Then, 20 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to this mixture. This mixture was deaerated while being stirred under reduced pressure, and after the deaeration, 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added. This mixture was refluxed at 110° C. for 5 hours. After the reflux, this mixture was cooled down to room temperature and approximately 20 mL of toluene was added to this mixture. The mixture was then filtered through alumina, Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). The obtained filtrate was concentrated, so that a light-brown oily substance was obtained. This oily substance was purified by a silica gel column chromatography (a developing solvent was a mixed solvent of hexane:toluene=6:4) to obtain a light-yellow solid substance. The obtained light-yellow solid substance was recrystallized with ethanol, so that 1.7 g of a light-yellow powdered solid substance was obtained in 93% yield. At a pressure of 8.7 Pa and with an argon gas flowing with a flow rate of 3.0 mL/min, 1.6 g of the obtained light-yellow powdered solid substance was heated at 230° C. so as to be sublimated and purified (a train sublimation method).
60%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; XPhos In toluene at 120℃; for 4h; Reflux;	9-(,9,10-diphenylanthracen-6-yl)-9H-carbazole (1) 2-bromo-9,10-diphenylanthracene (1.0 mmol), 9H-carbazole (1.5 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.05 mmol), dicyclohexylphosphino-2,4,6-triisopropylbiphenyl(0.08 mmol), sodium tert-butoxide (3.0 mmol) and anhydrous toluene (14 ml) were mixedin a flask. The mixture was refluxed at 120°C for 4 h. After the reaction finished, the reactionmixture was extracted with toluene and washed with water. The organic layerwas driedwithanhydrous MgSO4 and filtered with silica gel. The solution was then evaporated. The crudeproduct was purified recrystallization from CH2Cl2/EtOH. Yield: 60%. 1H NMR (CDCl3,500 MHz, δ); 8.11 (d, J = 8.0 Hz, 2 H), 7.91 (d, J = 9.0 Hz, 1 H), 7.88 (s, 1 H), 7.77-7.73(m, 2 H), 7.67-7.64 (m, 2 H), 7.60 (d, J = 7.0 Hz, 1 H), 7.58-7.55 (m, 4 H), 7.54-7.51 (m,4 H), 7.46 (d, J = 7.0 Hz, 1 H), 7.43 (d, J = 8.5 Hz, 2 H), 7.40-7.38 (m, 3 H) 7.37 (d, J =8.5 Hz, 2 H); 13C NMR (CDCl3, 500 MHz, δ); 140.7, 138.7, 138.5, 137.5, 137.2, 134.2, 131.3,131.2, 131.1, 130.5, 130.2, 130.2, 129.2, 128.7, 128.6, 127.8, 127.8, 127.1, 127.0, 125.9, 125.6,125.4, 124.4, 123.8, 123.4, 120.3, 120.0, 109.8; FT-IR [ATR]: ν (cm-1) 3026, 2378, 2351, 2312,1740, 1368, 1270, 1216; APCI-MS (m/z): 495 [M+].

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/253916, 2009, A1 Location in patent: Page/Page column 28
[2]Kim, Dong Young; Kim, Young Seok; Lee, Song Eun; Kim, Young Kwan; Yoon, Seung Soo [Molecular Crystals and Liquid Crystals, 2017, vol. 644, # 1, p. 197 - 204]

16
[ 419536-33-7 ]
[ 201731-79-5 ]
[ 1202059-35-5 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 100℃; for 20h;Inert atmosphere;	[Step 1] Synthesis of 9-[4-(9,10-Diphenyl-2-anthryl)phenyl]-9H-carbazole(abbreviation: 2CzPPA)A synthesis scheme of 2CzPPA is illustrated in (D-I). [0371] [0372] <n="139"/>In a 100 niL three neck flask were put 2.0 g (4.9 mmol) of 2-bromo-9,10-diphenylanthracene, 1.4 g (4.9 mmol) of4-(9H-carbazol-9-yl)phenylboronic acid, and 0.15 g (0.50 mmol) of tri(ortho-tolyl)phosphine, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 15 mL of toluene, 15 mL of ethanol, and 10 mL of an aqueous potassium carbonate solution (2.0 mol/L). This mixture was deaerated while being stirred under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. To this mixture was added 23 mg (0.10 mmol) of palladium(II) acetate. This mixture was refluxed at 100 0C for 20 hours. Then, after this mixture was cooled to room temperature, about 50 mL of toluene was added thereto, and the mixture was filtered through a filter paper. The obtained mixture was washed with water, and the aqueous layer was extracted with toluene. The extract solution and the organic layer were combined and washed with a saturated saline solution, and the organic layer was dried with magnesium sulfate. This mixture was gravity filtered. The obtained filtrate was concentrated to give a light yellow solid. This solid was washed with toluene to give the object of the synthesis as 1.5 g of a light yellow powdered solid in a yield of 54 %. [0373]Then, 1.5 g of the obtained light-yellow powdered solid was sublimated and purified by train sublimation. For sublimation purification conditions, 2CzPPA was heated at 260 C with argon gas at a flow rate of 3.0 mL/min. After the sublimation purification, 2CzPPA was recovered as 1.4 g of a light yellow solid in a yield of 94 %. [0374]By nuclear magnetic resonance (NMR) measurement, it was confirmed that this compound was 9-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole (abbreviation: 2CzPPA). [0375]The 1H NMR data of 2CzPPA are shown as follows: 1H NMR (CDCl3, 300 MHz):delta = 7.30 (d, J = 6.3 Hz, 2H), 7.33-7.75 (m, 21H), 7.77 (d, J = 8.1 Hz, 2H)5 7.85 (d, J = 9.0 Hz, IH), 8.01 (d, J = 2.1 Hz, IH), 8.15 (d, J = 7.8 Hz, 2H). Further, FIGS. 2OA and 2OB show 1H NMR charts. Note that FIG. 2OB is a chart in which the range of 7.0 <n="140"/>to 8.5 ppm in FIG. 2OA is enlarged. [0376]

Reference： [1]Patent: WO2009/131199,2009,A1 .Location in patent: Page/Page column 137-138

17
[ 854952-58-2 ]
[ 201731-79-5 ]
[ 1192650-81-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate In ethanol; water; toluene at 110℃; for 12h; Inert atmosphere;	1.2; C.4 [Step 2] Synthesis of 2PCzPAA synthesis scheme of 2PCzPAiS illustrated in (C-4). [0354] [0355]In a 100 mL three neck flask were put 1.5 g (3.7 mmol) of 2-bromo-9,10-diphenylanthracene, 1.1 g (3.7 mmol) of4-(9H-carbazol-9-yl)phenylboronic acid, and 0.16 g (0.50 mmol) of tri(ortho-tolyl)phosphine, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 20 mL of toluene, 10 mL of ethanol, and 13 mL of an aqueous potassium carbonate solution (2.0 mol/L). This mixture was deaerated while being stirred under reduced pressure. Then, the atmosphere in the flask was replaced with nitrogen. To this mixture was added 28 mg (0.10 mmol) of palladium(II) acetate.This mixture was refluxed at 110 0C for 12 hours. Then, after this mixture was cooled to room temperature, about 20 mL of toluene was added thereto, and the mixture was filtered through Celite (a product of Wako Pure Chemical Industries, Ltd., Catalog No.531-16855). The organic layer of the obtained mixture was washed with water and a saturated saline solution, and dried with magnesium sulfate. This mixture was gravity filtered. The obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was a mixture of hexane and toluene in a ratio of 7:3). The obtained light yellow solid was recrystallized with ethanol to give 1.2 g of a light yellow powdered solid in a yield of 58 %.[0356]Then, 1.2 g of the obtained light-yellow powdered solid was sublimated and purified by train sublimation. For sublimation purification conditions, 2PCzPA was heated at 280 0C under a pressure of 8.7 Pa with argon gas at a flow rate of 3.0 mL/min.After the sublimation purification, 2PCzPA was recovered as 0.83 g of a light yellow solid in a yield of 74 %.[0357] By nuclear magnetic resonance (NMR) measurement, it was confirmed that this compound was 3-(9,10-diphenyl-2-anthryl)-9-phenyl-9H-carbazole (abbreviation:2PCzPA).[0358]The 1H NMR data of 2PCzPA are shown as follows: 1H NMR (CDCl3, 300 MHz):δ = 7.30-7.34 (m, 3H), 7.41-7.49 (m, 4H), 7.53-7.65 (m, 15H), 7.70-7.74 (m, 2H),7.79-7.84 (m, 2H), 7.98 (s, IH), 8.15 (d, J = 7.8 Hz, IH), 8.31 (d, J = 2.1 Hz, IH).Further, FIGS. 13 A and 13B show 1H NMR charts. Note that FIG. 13B is a chart in which the range of 7.0 to 8.5 ppm in FIG. 13A is enlarged.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2009/131199, 2009, A1 Location in patent: Page/Page column 132-133

18
[ 5467-74-3 ]
[ 201731-79-5 ]
[ 1123921-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In water; toluene at 120℃; for 3h;	3 Preparation of Compound (122)Compound (113) (4.9 g, 12 mmol), 4-bromophenylboronic acid (2.7 g, 13.2 mmol) and trans-dichlorobistriphenylphosphine palladium (II) (Pd(PPh3)2Cl2 (0.9 g, 1.2 mmol) were dissolved in toluene (120 mL). After adding aqueous 2 M sodium carbonate solution (60 mL) with stirring, the mixture was heated at 120° C. under reflux and reacted for 3 hours. The reaction mixture was then extracted with dichloromethane (200 mL), washed with aqueous sodium chloride solution (200 mL), and dried over anhydrous magnesium sulfate. After evaporating the organic layer under reduced pressure, the solid obtained was recrystallized from tetrahydrofuran (100 mL) to obtain Compound (122) (5.0 g, 10.3 mmol).

Reference： [1]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 9

19
[ 5467-74-3 ]
[ 201731-79-5 ]
[ 1158227-62-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate / trans-bis(triphenylphosphine)palladium dichloride / toluene; water / 3 h / 120 °C 2: Aliquat 336; calcium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 6 h / 120 °C

Reference： [1]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1

20
[ 929103-40-2 ]
[ 201731-79-5 ]
[ 1158227-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With Aliquat 336; calcium carbonate In water; toluene at 130℃; for 4h;	4 Preparation of Compound (129)A reaction vessel was charged with Compound (113) (12.8 g, 33.0 mmol) and the ester compound (Compound 128) (5 g, 11 mmol), and tetrakistriphenylphosphinepalladium (Pd(PPh3)4) (1.2 g, 1.1 mmol) was added thereto. The mixture was dissolved in toluene (100 mL). To the solution, added were Aliquat 336 (0.5 g, 1.1 mmol) and aqueous 2M calcium carbonate solution (30 mL). The resultant mixture was stirred at 130° C. under reflux for 4 hours. To the precipitate formed, excess amount of methanol was poured to form solid, which was then dissolved in chloroform (300 mL). After filtration, the organic solvent was removed. Recrystallization from tetrahydrofuran (200 mL) gave the target compound (129) (BATPN-1) (3.3 g, overall yield: 36%).1H NMR (200 MHz, CDCl3) δ=7.22-7.32 (m, 16H), 7.48-7.54 (m. 10H), 7.67-7.73 (m, 6H), 7.85-7.88 (m, 4H), 8.04-8.09 (t, 2H), 8.52-8.88 (m, 4H), 8.74 (s, 2H)MS/FAB: 884.34 (found), 885.10 (calculated)

Reference： [1]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 11

21
[ 890042-13-4 ]
[ 201731-79-5 ]
[ 1042669-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	With Aliquat 336;tetrakis(triphenylphosphine) palladium(0); calcium carbonate; In water; toluene; at 130℃; for 4h;	Preparation of Compound (116)A reaction vessel was charged with Compound (113) (4.2 g, 30.0 mmol) and the ester compound (Compound 115) (4.7 g, 10.0 mmol), and tetrakispalladiumtriphenylphosphine (Pd(PPh3)4) (1.2 g, 1.0 mmol) was added thereto. The mixture was dissolved in toluene (80 mL). To the solution, added were Aliquat 336 (0.5 g, 1.0 mmol) and aqueous 2M calcium carbonate solution (24 mL). The resultant mixture was stirred at 130 C. under reflux for 4 hours. To the precipitate formed, methanol (200 mL) was poured to form solid, which was then dissolved in chloroform (300 mL). After filtration, the organic layer was evaporated under reduced pressure. Recrystallization from tetrahydrofuran (30 mL) gave the target compound (116) (TPN-1) (2.2 g, overall yield: 38%).1H NMR (200 MHz, CDCl3) δ=7.22-7.32 (m, 8H), 7.48-7.54 (m. 5H), 7.67-7.89 (t, 8H), 8.10-8.12 (m, 3H), 8.34 (d, 1H), 8.93-8.99 (m, 3H)MS/FAB: 556.22 (found), 556.69 (calculated)

Reference： [1]Patent: US2011/54228,2011,A1 .Location in patent: Page/Page column 6

22
[ 1158227-50-9 ]
[ 201731-79-5 ]
[ 1158227-53-2 ]

Yield	Reaction Conditions	Operation in experiment
	With Aliquat 336; calcium carbonate In water; toluene at 130℃; for 4h;	2 Preparation of Compound (121)A reaction vessel was charged with Compound (113) (5.0 g, 12.2 mmol) and the ester compound (120) (7.6 g, 15.9 mmol), and tetrakispalladiumtriphenylphosphine (Pd(PPh3)4) (1.4 g, 1.2 mmol) was added thereto. After dissolving the mixture in toluene, added were Aliquat 336 (0.6 g, 1.2 mmol) and then aqueous 2 M calcium carbonate solution (30 mL). The reaction mixture was stirred at 130° C. under reflux for 4 hours. To the precipitate produced, poured was excess amount of methanol to form solid. The solid was dissolved in chloroform (300 mL), filtered, and the solvent was removed under reduced pressure. Recrystallization from tetrahydrofuran (300 mL) gave the target compound (121) (NTPN) (3.5 g, overall yield: 42%).1H NMR (200 MHz, CDCl3) δ=7.22-7.32 (m, 10H), 7.48-7.67 (m. 12H), 8.10-8.12 (m, 3H), 8.34 (dd, 1H), 8.93-8.99 (m, 3H)MS/FAB: 682.27 (found), 682.85 (calculated)

Reference： [1]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 8

23
[ 121-43-7 ]
[ 201731-79-5 ]
[ 597553-98-5 ]

Yield	Reaction Conditions	Operation in experiment
66%		1-3) Synthesis of 9,10-diphenylanthracene-2-boronic acid 10 g (0.024 mol) of 2-bromo-9,10-diphenylanthracene obtained from 1-2) and 100 ml of THF were loaded into a 500 ml reactor. Then, the temperature of the reactor was lowered to -78C and 16.80 ml (0.027 mol) of 1.6M n-BuLi was slowly added dropwise thereto. Then, the mixture was stirred for about one hour at low temperature and then 3.84 g (0.037 mol) of trimethylborate was added dropwise thereto. Then, the resultant mixture was stirred at room temperature for 4 hours and then 10 ml of 2N HCl was added thereto. Then, 100 ml of EA was added to the obtained mixture and extracted twice with EA/H2O, and an organic solvent was removed under reduced pressure. The obtained product was re-crystallized with EA/Hx (hexane), thereby producing a yellowish white crystal (6 g, 66%).
		Under nitrogen protection,50 ml of anhydrous tetrahydrofuran and 3.5 g of compound 1 were mixed,Cooling to -78 ,6 ml of n-butyllithium was added dropwise, and the reaction was stirred for 1 hour.3 ml of trimethoxyborane was added dropwise,After stirring for 1 hour, the reaction was allowed to proceed to room temperature for 2 hours.Hydrochloric acid was added and filtered to give compound 2.

Reference： [1]Patent: EP2292604,2011,A2 .Location in patent: Page/Page column 22
[2]Patent: CN106220571,2016,A .Location in patent: Paragraph 0045

24
[ 201731-79-5 ]
[ 1245526-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 4 h / 20 °C 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water; tetrahydrofuran / 12 h / Reflux

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292604, 2011, A2

25
[ 201731-79-5 ]
[ 1245526-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 4 h / 20 °C 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water; tetrahydrofuran / 12 h / Reflux 3.1: triphenylphosphine / 1,2-dichloro-benzene / 10 h / Reflux

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292604, 2011, A2

26
[ 201731-79-5 ]
[ 1245525-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 4 h / 20 °C 2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water; tetrahydrofuran / 12 h / Reflux 3.1: triphenylphosphine / 1,2-dichloro-benzene / 10 h / Reflux 4.1: sodium t-butanolate / tetrahydrofuran / 20 °C

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292604, 2011, A2

27
[ 1271726-52-3 ]
[ 201731-79-5 ]
[ 1307859-65-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 4h; Inert atmosphere;	6 Reference Example 6 To a 100 mL three-necked flask was added 1.2 g (3.0 mmol) of 2-bromo-9,10-diphenylanthracene, 0.87 g (3.0 mmol)3- (dibenzofuran-4-yl) phenylboronic acid and 0.23 g (0.75 mmol) of tris (o-tolyl) phosphine. The air in the flask was replaced with nitrogen. To the mixture was added 15 mL of toluene, 5.0 mL of ethanol and 3.0 mL of a 2.0 mol / L aqueous solution of potassium carbonate. The mixture was stirred and degassed while reducing the pressure.To the mixture was added 34 mg (0.15 mmol) of palladium (II) acetate, and the mixture was stirred at 80 ° C for 4 hours in a nitrogen stream. Then, the aqueous layer of the mixture was extracted with ethyl acetate, and the ethyl acetate solution and the organic layer were combined and washed with saturated brine. The organic layer was dried over magnesium sulfate. The mixture was then subjected to gravity filtration. The resulting solid obtained by concentrating the filtrate was purified by silica gel column chromatography. Using a 5: 1 mixture of hexane and toluene as a rinse solvent for chromatography to obtain a solid. The solid was recrystallized from a mixed solvent of toluene and hexane to give 1.4 g of a yellow powder in a yield of 79% as a synthetic substance.1.4 g of the obtained yellow powder solid was purified by a train sublimation method. In the purification, the yellow powder solid was heated at 270 ° C under a pressure of 3.0 Pa and an argon flow rate of 4.0 mL / min. After purification, 1.1 g of a yellow solid was obtained in 81% yield as a synthetic substanc
79%	With potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 4h; Inert atmosphere;	1 In a 100 mL three-neck flask were put 1.2 g (3.0 mmol) of 2-bromo-9,10-diphenylanthracene, 0.87 g (3.0 mmol) of 3-(dibenzofuran-4-yl)phenylboronic acid, and 0.23 g (0.75 mmol) of tri(ortho-tolyl)phosphine. The air in the flask was replaced with nitrogen. To this mixture were added 15 mL of toluene, 5.0 mL of ethanol, and 3.0 mL of a 2.0 mol/L aqueous solution of potassium carbonate. While the pressure was reduced, this mixture was stirred to be degassed. Then, 34 mg (0.15 mmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred under a nitrogen stream at 80 °C for 4 hours. Then, the aqueous layer of this mixture was extracted with ethyl acetate, and the extracted solution and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The resulting filtrate was concentrated to give a solid, and the solid was purified by silica gel column chromatography. The chromatography was carried out using a mixed solvent having a 5:1 ratio of hexane to toluene as a developing solvent, whereby a solid was obtained. Recrystallization of the solid from a mixed solvent of toluene and hexane gave 1.4 g of a yellow powder in 79 % yield, which was the substance to be produced. By a train sublimation method, 1.4 g of the obtained yellow powdered solid was purified. In the purification, the yellow powdered solid was heated at 270 °C under a pressure of 3.0 Pa with a flow rate of argon gas of 4.0 mL/min. After the purification, 1.1 g of a yellow solid was obtained in a yield of 81 %, which was the substance to be produced. A nuclear magnetic resonance (NMR) method identified this compound as 4-[3-(9,10-diphenyl-2-anthryl)phenyl]dibenzofuran (abbreviation: 2mDBFPPA-II), which was the substance to be produced. 1H NMR data of the obtained compound are: 1H NMR (CDCl3, 300 MHz): δ = 7.31-7.67 (m, 19H), 7.69-7.73 (m, 3H), 7.80-7.86 (m, 2H), 7.95 (dd, J1 = 0.90 Hz, J2= 1.8 Hz, 1H), 7.98-8.01 (m, 2H), 8.07 (s, 1H).

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - TWI565701, 2017, B Location in patent: Page/Page column 109; 110; 111
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - EP2330102, 2011, A1 Location in patent: Page/Page column 57-58

28
[ 1307859-67-1 ]
[ 201731-79-5 ]
[ 1307859-69-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 5h; Inert atmosphere;	5 Reference Example 5 In a 100 mL three-necked flask was added 1.6 g (4.0 mmol)2-bromo-9,10-diphenylanthracene, 1.2 g (4.0 mmol)3- (dibenzothiophen-4-yl) phenylboronic acid and 0.30 g (1.0 mmol)Tris (o-tolyl) phosphine. The air in the flask was replaced with nitrogen. To the mixture was added 25 mL of toluene, 5.0 mL of ethanol and 5.0 mL of a 2.0 mol / L aqueous solution of potassium carbonate. The mixture was stirred and degassed while reducing the pressure.To the mixture was added 45 mg (0.20 mmol) of palladium (II) acetate, and the mixture was stirred at 80 ° C for 5 hours in a stream of nitrogen. Then, the aqueous layer of the mixture was extracted with toluene, and the toluene solution and the organic layer were combined and washed with saturated brine. The organic layer was dried over magnesium sulfate. The mixture was then subjected to gravity filtration. The resulting filtrate was concentrated to give an oil. The resulting oil was purified by silica gel column chromatography. Using a 5: 1 mixture of hexane and toluene as a rinse solvent for chromatography to obtain a solid. The solid was recrystallized from a mixed solvent of toluene and hexane to give 1.6 g of a yellow powder in a yield of 70% as a synthetic substance.1.6 g of the obtained yellow powder solid was purified by a train sublimation method. In the purification, the yellow powder solid was heated at 290 ° C at a pressure of 3.0 Pa and an argon flow rate of 4.0 mL / min. After purification, 1.4 g of a yellow solid was obtained in 87% yield as a synthetic substance.
70%	With potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 80℃; for 5h; Inert atmosphere;	2 In a 100 mL three-neck flask were put 1.6 g (4.0 mmol) of 2-bromo-9,10-diphenylanthracene, 1.2 g (4.0 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, and 0.30 g (1.0 mmol) of tri(ortho-tolyl)phosphine. The air in the flask was replaced with nitrogen. To this mixture were added 25 mL of toluene, 5.0 mL of ethanol, and 5.0 mL of a 2.0 mol/L aqueous solution of potassium carbonate. While the pressure was reduced, this mixture was stirred to be degassed. Then, 45 mg (0.20 mmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred under a nitrogen stream at 80 °C for 5 hours. Then, the aqueous layer of this mixture was extracted with toluene, and the toluene solution and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The resulting filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. The chromatography was carried out using a mixed solvent having a 5:1 ratio of hexane to toluene as a developing solvent, whereby a solid was obtained. Recrystallization of the solid from a mixed solvent of toluene and hexane gave 1.6 g of a yellow powder in 70 % yield, which was the substance to be produced. By a train sublimation method, 1.6 g of the obtained yellow powdered solid was purified. In the purification, the yellow powdered solid was heated at 290 °C under a pressure of 3.0 Pa with a flow rate of argon gas of 4.0 mL/min. After the purification, 1.4 g of a yellow solid was obtained in a yield of 87 %, which was the substance to be produced. A nuclear magnetic resonance (NMR) method identified this compound as 4-[3-(9,10-diphenyl-2-anthryl)phenyl]dibenzothiophene (abbreviation: 2mDBTPPA-II), which was the substance to be produced. 1H NMR data of the obtained compound are: 1H NMR (CDCl3, 300 MHz): δ = 7.33 (q, J1 = 3.3 Hz, 2H), 7.46-7.73 (m, 20H), 7.80-7.87 (m, 2H), 7.99 (st, J1 = 1.8 Hz, 1H), 8.03 (sd, J1 = 1.5 Hz, 1H), 8.14-8.20 (m, 2H).

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - TWI565701, 2017, B Location in patent: Page/Page column 107; 108; 109
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - EP2330102, 2011, A1 Location in patent: Page/Page column 59-60

29
[ 1335379-13-9 ]
[ 201731-79-5 ]
[ 1335379-07-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In toluene for 4h; Reflux; Inert atmosphere;

Reference： [1]Location in patent: experimental part Lee, Kum Hee; Park, Jeong Keun; Seo, Ji Hoon; Park, Se Won; Kim, Young Sik; Kim, Young Kwan; Yoon, Seung Soo [Journal of Materials Chemistry, 2011, vol. 21, # 35, p. 13640 - 13648]

30
[ 76-86-8 ]
[ 201731-79-5 ]
[ 1335379-11-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With n-butyllithium In tetrahydrofuran Inert atmosphere;
44%	Stage #1: 2-bromo-9,10-diphenylanthracene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.75h; Inert atmosphere; Schlenk technique; Stage #2: Triphenylsilyl chloride In diethyl ether; hexane at -78 - 20℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Location in patent: scheme or table Lee, Kum Hee; Park, Jeong Keun; Seo, Ji Hoon; Park, Se Won; Kim, Young Sik; Kim, Young Kwan; Yoon, Seung Soo [Journal of Materials Chemistry, 2011, vol. 21, # 35, p. 13640 - 13648]
[2]Wu, Cheng-Lung; Chang, Che-Hong; Chang, Yung-Ting; Chen, Chin-Ti; Chen, Chao-Tsen; Su, Chi-Jung [Journal of Materials Chemistry C, 2014, vol. 2, # 35, p. 7188 - 7200]

31
[ 591-51-5 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene; diethyl ether; dibutyl ether / 6 h / -20 °C 2: potassium iodide; acetic acid; sodium hypophosphite monohydrate / 6 h / Reflux

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1

32
[ 201731-79-5 ]
[ 1123921-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -80 °C 1.2: 2 h 1.3: 12 h 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 12 h / 90 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 8 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

33
[ 201731-79-5 ]
[ 1350928-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -80 °C 1.2: 2 h 1.3: 12 h 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 12 h / 90 °C

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1

34
[ 201731-79-5 ]
[ 1350928-50-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -80 °C 1.2: 2 h 1.3: 12 h 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 12 h / 90 °C 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 12 h / 90 °C

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1

35
[ 201731-79-5 ]
[ 1350928-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -80 °C 1.2: 2 h 1.3: 12 h 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 12 h / 90 °C

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1

36
[ 150-46-9 ]
[ 201731-79-5 ]
[ 597553-98-5 ]

Yield	Reaction Conditions	Operation in experiment
72%		Exemplary Synthesis 1; Synthesis of Compound 1; Synthesis of 9,10-Diphenylanthracene-2-Boronic Acid; An amount of 6.8 g (23.7 mmol) of 2-bromoanthraquinone was suspended in a mixed solvent of 50 ml of dehydrated toluene and 50 ml of dehydrated ether and cooled to -20 C. An amount of 26.3 ml (50 mmol) of a solution of phenyllithium (1.9 mmol/ml) in butylether was added and allowed to react for six hours. Then, distilled water was added to stop the reaction. Then, the separated organic layer was applied to column chromatography to obtain a diol form. Then, the obtained diol form, 39 g (237 mmol) of potassium iodide, and 41 g (390 mmol) of sodium hypophosphite monohydrate were dissolved in acetic acid and refluxed for six hours. After cooling, the deposit was filtered and purified by column chromatography to obtain 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene. The yield was 48.3%.An amount of 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene was dissolved in dehydrated THF and cooled to -80 C. An amount of 7.9 ml (12 mmol) of a solution of n butyllithium in n hexane was added dropwise and, 40 minutes later, 3.33 g (22.8 mmol) of triethyl borate was further added. After two-hour reaction, a dilute hydrochloric acid solution was added and the mixture was allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 3.07 g (8.2 mmol) of 9,10-diphenylanthracene-2-boronic acid. The yield was 72%.

Reference： [1]Patent: US2011/295017,2011,A1 .Location in patent: Page/Page column 21

37
[ 1299493-18-7 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hypophosphite monohydrate; acetic acid; potassium iodide for 6h; Reflux;	1 Exemplary Synthesis 1; Synthesis of Compound 1; Synthesis of 9,10-Diphenylanthracene-2-Boronic Acid; An amount of 6.8 g (23.7 mmol) of 2-bromoanthraquinone was suspended in a mixed solvent of 50 ml of dehydrated toluene and 50 ml of dehydrated ether and cooled to -20° C. An amount of 26.3 ml (50 mmol) of a solution of phenyllithium (1.9 mmol/ml) in butylether was added and allowed to react for six hours. Then, distilled water was added to stop the reaction. Then, the separated organic layer was applied to column chromatography to obtain a diol form. Then, the obtained diol form, 39 g (237 mmol) of potassium iodide, and 41 g (390 mmol) of sodium hypophosphite monohydrate were dissolved in acetic acid and refluxed for six hours. After cooling, the deposit was filtered and purified by column chromatography to obtain 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene. The yield was 48.3%.An amount of 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene was dissolved in dehydrated THF and cooled to -80° C. An amount of 7.9 ml (12 mmol) of a solution of n butyllithium in n hexane was added dropwise and, 40 minutes later, 3.33 g (22.8 mmol) of triethyl borate was further added. After two-hour reaction, a dilute hydrochloric acid solution was added and the mixture was allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 3.07 g (8.2 mmol) of 9,10-diphenylanthracene-2-boronic acid. The yield was 72%.

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1 Location in patent: Page/Page column 21

38
[ 201731-79-5 ]
[ 25015-63-8 ]
[ 1133796-55-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In toluene at 100℃; for 5h;	3 Next, 4.1 g (10 mmol) of E10 and 1.08 g (2 mmol) of Ni (dppp) 2CI2 were put in 100 mL of toluene, 3.03 g (30 mmol) of triethylamine and 3.83 g (30 mmol) of Ell were put in the solution, and it was stirred at 100°C for five hours. After cooling, the solution was filtered and. was washed twice with 100 mL of water. The organic layer was washed withsaturated saline and was dried over magnesium sulfate. The solution was then filtered, and the filtrate wasconcentrated to yield a dark brown liquid. This waspurified by column chromatography (toluene/heptane, 5:1) and was recrystallized from toluene/heptane to yield 3.19 g of E12 (yield: 70%) .

Reference： [1]Current Patent Assignee: CANON INC. - WO2011/152477, 2011, A1 Location in patent: Page/Page column 37-38

39
[ 201731-79-5 ]
[ 845712-39-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / toluene / 5 h / 100 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 150 °C

Reference： [1]Current Patent Assignee: CANON INC. - WO2011/152477, 2011, A1

40
[ 201731-79-5 ]
[ 605656-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / toluene / 5 h / 100 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 150 °C 3: N-Bromosuccinimide / chloroform / 8 h / 60 °C

Reference： [1]Current Patent Assignee: CANON INC. - WO2011/152477, 2011, A1

41
[ 201731-79-5 ]
[ 1351162-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / toluene / 5 h / 100 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 150 °C 3: N-Bromosuccinimide / chloroform / 8 h / 60 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 4 h / 150 °C

Reference： [1]Current Patent Assignee: CANON INC. - WO2011/152477, 2011, A1

42
[ 5471-63-6 ]
[ 20776-50-5 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With isopentyl nitrite; In toluene; at 80 - 100℃; for 3h;	EXAMPLE 3; Synthesis of Exemplary Compound A3; Put in 100 mL of toluene were 5.41 g (20 mmol) of E8 and 5.18 g (24 mmol) of E9. After the solution was heated to 80C, 2.81 g (24 mmol) of isoamyl nitrite was gradually added dropwise, and the solution was gradually heated from 80C and was stirred at 100C for three hours. After cooling, the solution was washed twice with 100 mL of water. The organic layer was washed with saturated saline and was dried over magnesium sulfate. The solution was then filtered, and the filtrate was concentrated to yield a dark brown liquid. This was purified by column chromatography (toluene/heptane, 2:3) and was recrystallized fromtoluene/ethanol to yield 3.77 g of E10 (yield: 46%).

Reference： [1]Patent: WO2011/152477,2011,A1 .Location in patent: Page/Page column 36-37

43
[ 1346669-46-2 ]
[ 201731-79-5 ]
[ 1365891-52-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium t-butanolate In hexane; toluene at 110℃; for 10h; Inert atmosphere;	5.5.2 To a 100-mL three-neck flask were added 1.00 g (3.00 mmol) of 2-bromo-9,10-diphenylanthracene, 1.23 g (3.00 mmol) of 3-(dibenzofuran-4-yl)-9H-carbazole, and 0.86 g (9.00 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, to this mixture were added 20 mL of toluene and 0.2 mL of tri-(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed by being stirred while the pressure was reduced. After the degassing, 86 mg (0.15 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. This mixture was stirred at 110° C. for 10 hours under a nitrogen stream. After the reflux, the mixture was cooled to room temperature, and then the obtained solid was collected by suction filtration. The collected solid was dissolved in 100 mL of toluene, and this solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina. The obtained filtrate was concentrated to give an orange solid. The obtained solid was purified by silica gel column chromatography. In the column chromatography, a solution of toluene:hexane=1:5 was used as a developing solvent. The obtained fraction was concentrated to give a pale yellow solid. The obtained solid was recrystallized from toluene/hexane, so that 1.27 g of a pale yellow solid was obtained in 64% yield. The synthesis scheme of Step 2 is illustrated in (b-5). This compound was identified as 3-(dibenzofuran-4-yl)-N-(9,10-diphenylanthracen-2-yl)-9H-carbazole (abbreviation: 2 DBFCz-II) by nuclear magnetic resonance (NMR) spectroscopy. 1H NMR. data of the obtained compound is shown below. In addition, 1H NMR charts are shown in FIGS. 19A and 19B.1H NMR (CDCl3, 300 MHz): δ=7.26-7.49 (m, 9H), 7.54-7.72 (m, 13H), 7.75-7.79 (m, 2H), 7.92-7.97 (m, 4H), 8.01 (d, J=8.1 Hz, 1H), 8.21 (d, J=7.5 Hz, 1H), 8.63 (d, J=0.9 Hz, 1H)

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2012/71668, 2012, A1 Location in patent: Page/Page column 240-241

44
[ 1256544-27-0 ]
[ 201731-79-5 ]
[ 1256545-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; water for 8h; Inert atmosphere; Reflux;	61 Example 61; [Show Image] In the atmosphere of argon, 4.08g of 2-bromo-9,10-diphenylanthracene, 3.14g of a boronic acid derivative of intermediate (H), 0.231g of tetrakis(triphenylphosphine)palladium (0), 40 mL of 1,2-dimethoxyethane and 20 mL of a 2M aqueous sodium carbonate solution were placed in a flask. The resulting mixture was stirred under reflux for 8 hours. After cooling to room temperature, deposited solids were filtered. The resulting solids were washed with water and methanol, recrystallized from toluene, whereby 4.48g of yellow solids of compound 61 was obtained. As a result of mass spectroscopy, it was confirmed that this compound was an intended product having an m/e of 546 relative to the molecular weight of 546.20.

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2436679, 2012, A1 Location in patent: Page/Page column 78-79

45
[ 201731-79-5 ]
[ 1123921-74-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; water / 8 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

46
[ 117-79-3 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 6 h / 65 °C 1.2: 3 h 2.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 3.1: potassium iodide; acetic acid; sodium hypophosphite monohydrate / 2 h / 120 °C 3.2: 1 h / 120 °C
	Multi-step reaction with 2 steps 1: copper(I) bromide; tert.-butylnitrite / acetonitrile / 60 °C 2: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2
[2]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN106220571, 2016, A

47
[ 572-83-8 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2.1: potassium iodide; acetic acid; sodium hypophosphite monohydrate / 2 h / 120 °C 2.2: 1 h / 120 °C

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

48
[ 201731-79-5 ]
[ 1123921-70-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 8 h / 100 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 5 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

49
[ 201731-79-5 ]
[ 1123921-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 8 h / 100 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 5 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

50
[ 201731-79-5 ]
[ 1136225-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 8 h / 100 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 3 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

51
[ 201731-79-5 ]
[ 1123921-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; water / 8 h / 110 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 5 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

52
[ 201731-79-5 ]
[ 1123921-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; water / 8 h / 110 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 5 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

53
[ 201731-79-5 ]
[ 1404222-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 8 h / 100 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 3 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

54
[ 201731-79-5 ]
[ 1404222-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium; sodium thiosulfate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 13 h / -78 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 8 h / 100 °C / Inert atmosphere 3.1: sodium t-butanolate; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / toluene; hexane / 3 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US8288012, 2012, B2

55
[ 201731-79-5 ]
[ 1079-66-9 ]
C₃₈H₂₇OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 2-bromo-9,10-diphenylanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Schlenk technique; Stage #2: chloro-diphenylphosphine In tetrahydrofuran; hexane at -78 - 20℃; for 6h; Inert atmosphere; Schlenk technique; Stage #3: With dihydrogen peroxide In dichloromethane; water for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Wu, Cheng-Lung; Chang, Che-Hong; Chang, Yung-Ting; Chen, Chin-Ti; Chen, Chao-Tsen; Su, Chi-Jung [Journal of Materials Chemistry C, 2014, vol. 2, # 35, p. 7188 - 7200]

56
[ 436-59-9 ]
[ 201731-79-5 ]
C₄₄H₃₉B [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	Stage #1: 2-bromo-9,10-diphenylanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Schlenk technique; Stage #2: dimesitylfluoroborane In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Wu, Cheng-Lung; Chang, Che-Hong; Chang, Yung-Ting; Chen, Chin-Ti; Chen, Chao-Tsen; Su, Chi-Jung [Journal of Materials Chemistry C, 2014, vol. 2, # 35, p. 7188 - 7200]

57
[ 90-30-2 ]
[ 201731-79-5 ]
C₄₂H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 16h; Inert atmosphere; Schlenk technique;

Reference： [1]Wu, Cheng-Lung; Chang, Che-Hong; Chang, Yung-Ting; Chen, Chin-Ti; Chen, Chao-Tsen; Su, Chi-Jung [Journal of Materials Chemistry C, 2014, vol. 2, # 35, p. 7188 - 7200]

58
[ 201731-79-5 ]
[ 62-53-3 ]
N-9,10-triphenyl-N-(9,10-diphenylanthracen-3-yl)anthracen-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With palladium diacetate; johnphos; sodium t-butanolate In toluene at 120℃; Inert atmosphere;	2.1.3. N-9,10-triphenyl-N-(9,10-diphenylanthracen-3-yl)anthracen-2-amine (3) Yield: 46%. 2-bromo-9,10-diphenylanthracene(1.61 mmol), Pd(OAc)2 (0.13 mmol), 2-Biphenyl)di-tertbutylphosphine(0.26 mmol), and NaO-t-Bu (1.93 mmol)were mixed in a flask. Aniline (0.64 mmol) and toluene were added under a flow of nitrogen. The reaction mixture was refluxed from 120 C for overnight while stirring under nitrogen. After the reaction finished, the reaction mixture was cooled to room temperature. The product was purified through column chromatography (hexane:ethyl acetate). Recrystallization from tetrahydrofuran and methanol.1H NMR (CDCl3, 500 MHz, ); 7.66-7.64 (m, 4 H),7.62-7.59 (m, 5 H), 7.56 (d, J = 8.5 Hz, 2 H), 7.51-7.49(m, 6 H), 7.32-7.25 (m, 15 H), 7.19-7.14 (m, 4 H), 7.08(s, 2 H), 7.06 (d, J = 7.5 Hz, 2 H), 7.00 (t, J = 7.5 Hz,1 H); APCI-MS (m/z): 749 [M+].

Reference： [1]Lee, Seul Bee; Song, Ji Young; Yang, Hyung Jin; Kim, Young Kwan; Yoon, Seung Soo [Journal of Nanoscience and Nanotechnology, 2015, vol. 15, # 7, p. 5238 - 5241]

59
[ 201731-79-5 ]
[ 73183-34-3 ]
[ 1133796-55-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; tricyclohexylphosphine In 1,4-dioxane for 8h; Reflux;	2-7 <Preparation Example 2-7> Preparation of the following Compound B-14 Preparation of the following Compound B-14 Compound B-13 (16.7 g, 40.8 mmol), bis(pinacolato)diboron (11.4 g, 44.9 mmol), and potassium acetate (KOAc) (12.0 g, 122 mmol) were suspended in 1,4-dioxane (250 mL). Pd(dba)2 (0.70 g, 3 mol%) and PCy3 (0.69 g, 6 mol%) were added to the suspension. The mixture was stirred under reflux for about 8 hours, and cooled to normal temperature. The mixture was diluted with water (250 mL) and extracted with chloroform (3 x 150 mL). The organic extract was dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and recrystallized with ethyl ether and hexane to prepare Compound B-14 (14.9 g, 80%). MS: [M+H] + = 457

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - EP2876104, 2015, A1 Location in patent: Paragraph 0137-0138

60
[ 201731-79-5 ]
C₄₂H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine / 1,4-dioxane / 8 h / Reflux 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 5 h / Reflux

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - EP2876104, 2015, A1

61
[ 201731-79-5 ]
[ 245-08-9 ]
5-(9,10-diphenylanthracen-7-yl)-5H-pyrido[3,2-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 80℃; for 1h;Inert atmosphere;	2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), delta-carboline (0.27g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.47g (3-1, AnT-dC3)(yield: 65%)is obtained.
65%		2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), delta-carboline (0.27g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-1, AnT-dC3) 0.47g (yield: 65%) was obtained.
65%		2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), delta-carboline (0.27g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 C and reacted for 1 hour. To the resulting solution was added Pd (dba)2 (0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) and the reaction was performed at 80C for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-1, AnT-dC3) 0.47g (yield: 65%)

60%

With johnphos; sodium t-butanolate; In toluene; at 120℃; for 4h;

2-bromo-9,10-diphenylanthracene (0.73 mmol), <strong>[245-08-9]5H-pyrido[3,2-b]indole</strong> (0.59 mmol), Tris(dibenzylideneacetone)dipalladium (0.04 mmol), [1,1-biphenyl]-2-ylbis(1,1-dimethylethyl)phosphine (0.007 mmol), and anhydrous toluene were mixed in a flask. The mixture was refluxed for 4 hours at 120 C. After the reaction had finished, the reaction mixture was extracted with toluene and washed with water. The organic layer was dried with anhydrous MgSO4 and filtered with silica gel. The solution was then evaporated. The crude product was purified recrystallizationfrom CH2Cl2/EtOH. Yield: 60%. 1H NMR (CDCl3,500 MHz, ; 8.59 (d, J = 5.0 Hz, 1H), 8.41 (d, J =8.0 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 7.85 (s, 1H),7.78-7.74 (m, 2H), 7.71 (d, J = 8.0 Hz, 1H), 7.68-7.65(m, 2H), 7.61 (d, J = 7.5 Hz, 1H), 7.56-7.55 (m, 4H),7.54-7.51 (m, 3H), 7.50-7.43 (m, 3H), 7.43-7.39 (m, 2H),7.36 (t, J = 8.0 Hz, 1H), 7.29 (d, J = 8.0 Hz, 1H); APCIMS(m/z: 496 [M+].

Reference： [1]Patent: KR101528769,2015,B1 .Location in patent: Paragraph 0088; 0089; 0090; 0095; 0096; 0097; 0098
[2]Patent: KR101528767,2015,B1 .Location in patent: Paragraph 0088-0089; 0095-0096
[3]Patent: KR101528768,2015,B1 .Location in patent: Paragraph 0090;0095-0096
[4]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 7804 - 7807

62
[ 785051-54-9 ]
[ 201731-79-5 ]
[ 1202059-35-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 120℃; for 2h;	<strong>[785051-54-9]9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole</strong> (2.1 mmol) and 2-bromo-9,10-diphenylanthracene (1.95 mmol), Pd(PPh3)4(0.08 mmol), aqueous 2.0 M K2CO3 (0.02 mol), Aliquat 336 (0.2 mmol), and toluene were mixed in a flask and refluxed for 2 h at 120 C. After being cooled,the purification was carried out by recrystallization with CH2Cl2/EtOH.1H NMR (CDCl3, 500 MHz, ); 8.14 (d, J = 8.0 Hz,2H), 8.01 (s, 1H), 7.84 (d, J = 9.0 Hz, 2H), 7.76-7.71(m, 4H), 7.68 (d, J = 7.5 Hz, 1H), 7.64 (t, J = 7.5 Hz,3H), 7.60-7.57 (m, 5H), 7.54 (t, J = 7.5 Hz, 3H), 7.45(d, J = 8.5 Hz, 2H), 7.40 (t, J = 7.0 Hz, 2H), 7.36-7.34(m, 2H), 7.28 (t, J = 7.0 Hz, 2H); 13C NMR (CDCl3,500 MHz, ); 140.7. 140.0, 138.9, 138.9, 137.6, 137.1,136.9, 136.3, 131.4, 131.3, 130.4, 130.1, 130.0, 129.1,128.6, 128.6, 128.5, 127.9, 127.7, 127.6, 127.3, 127.0,127.0, 125.9, 125.3, 125.2, 124.7, 124.6, 123.4, 120.3,120.0 109.8; FT-IR [ATR]: (cm-1 3054, 2334, 1517,1451, 1228, 948, 820, 748, 723, 700; APCI-MS (m/z:571 [M+]

Reference： [1]Journal of Nanoscience and Nanotechnology,2016,vol. 16,p. 8465 - 8469

63
[ 267221-88-5 ]
[ 201731-79-5 ]
N-phenyl-N-(4-(9,10-diphenylanthracen-7-yl)phenyl)benzenamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 120℃; for 2h;	General procedure: 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (2.1 mmol) and 2-bromo-9,10-diphenylanthracene (1.95 mmol), Pd(PPh3)4(0.08 mmol), aqueous 2.0 M K2CO3 (0.02 mol), Aliquat 336 (0.2 mmol), and toluene were mixed in a flask and refluxed for 2 h at 120° C. After being cooled,the purification was carried out by recrystallization with CH2Cl2/EtOH

Reference： [1]Kim, Young Seok; Kim, Dong Young; Lee, Song Eun; Kim, Young Kwan; Yoon, Seung Soo [Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 8, p. 8465 - 8469]

64
[ 244-76-8 ]
[ 201731-79-5 ]
[ 1219907-25-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	2 synthesis of compound 3-2 (aC3 - AnT) 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), alpha-carboline (0.27g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) adding an 1-2 reacted in 80 °C days. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.47g (3-2, AnT-aC3)(yield: 65%)is obtained.
65%	Stage #1: α-carboline; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	2 Synthesis of Compound 3-2, aC3-AnT 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), alpha-carboline (0.27g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 1-2 days. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-2, aC3-AnT) 0.47g: (yield: 65%).
65%	Stage #1: α-carboline; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	2 Synthesis of AnT-aC3 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), alpha-carboline (0.27g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 1-2 days. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound 3-2(AnT-aC3) 0.47g: (yield: 65%)

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0099; 0100; 0101; 0102; 0103; 0104
[2]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0099-0103
[3]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0101-0103

65
[ 1195517-26-0 ]
[ 201731-79-5 ]
7-(9,10-diphenylanthracen-3-yl)-7H-benzo[e]pyrido[3,2-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 7H-benzo[e]pyrido[3,2-b]indole; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	3 Synthesis of Compound 3-3, AnT-dC2 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), benzo delta-carboline (0.35g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-3, AnT-dC2) 0.48g (yield: 60%) was obtained.
60%	Stage #1: 7H-benzo[e]pyrido[3,2-b]indole; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	3 Synthesis of Compound 3-3 (AnT-dC2) 2-necked 250ml flask was charged with compound (2) (0.6g, 1.47mmol), benzo delta-carboline (0.35g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) and toluene (100ml) under nitrogen into the stirred, and the reaction temperature was raised to 80°C and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80°C for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-3, AnT-dC2) 0.48g (yield: 60%)
	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	3 synthesis of (dC2 - AnT)3-compound 3 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), benzo delta-carboline (0.35g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 °C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.48g (3-3, AnT-dC2)(yield: 60%)is obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0105-0109
[2]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0105-0109
[3]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0105; 0106; 0107; 0108; 0109; 0110

66
C₂₃H₁₅N₃ [ No CAS ]
[ 201731-79-5 ]
C₄₉H₃₁N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	4 synthesis of (BeAdC3 - AnT)3-4 compound 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), n-phenyl indolo carboline (0.54g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 °C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.63g (3-4, BeAdC3-AnT)(yield: 65%)is obtained.
65%	Stage #1: C₂₃H₁₅N₃; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	4 Synthesis of Compound 3-4, AnT-BeAdC3 2-necked 250ml flask was charged with compound (2) (0.6g, 1.47mmol), n-phenyl indolo carboline (0.54g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) and toluene (100ml) under nitrogen into the stirred, raising the reaction temperature to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-4, AnT-BeAdC3) 0.63g (yield: 65%) was obtained.
65%	Stage #1: C₂₃H₁₅N₃; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	4 Synthesis of Compound 3-4 (AnT-BeAdC3) 2-necked 250ml flask into the compound (2) (0.6g, 1.47mmol), n-phenyl indolo carboline (0.54g, 1.62mmol), and NaOtBu (0.42g, 4.41mmol) in toluene (100ml) and stirred under nitrogen, raising the reaction temperature to 80 °Cand reacted for 1 hour. To the resulting solution was added Pd(dba) 2 (0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) and the reaction was performed at 80°C for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-4, AnT-BeAdC3) 0.63g (yield: 65%) was obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0111; 0112; 0113; 0114; 0115; 0116
[2]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0111-0115
[3]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0111-0115

67
C₁₃H₈N₂O [ No CAS ]
[ 201731-79-5 ]
C₃₉H₂₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	5 3-5 compound (BeFuP - AnT)synthesis of 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), benzofuro pyrrolopyridine (0.34g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 °C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.5g (3-5, AnT-BeFuP)(yield: 63%)is obtained.
63%	Stage #1: C₁₃H₈N₂O; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	5 Synthesis of Compound 3-5 (AnT-BeFuP) 2-necked 250ml flask was charged with compound (2) (0.6g, 1.47mmol), benzofuro pyrrolopyridine (0.34g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) and toluene (100ml) under stirring in nitrogen put, and the reaction temperature to raising the temperature to 80 °C and reacted for 1 hour. Here Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) was added and 80°C for 4 to 5 hours It was reacted. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-5, AnT-BeFuP) 0.5g (yield: 63%)

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0117; 0118; 0119; 0120; 0121; 0122
[2]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0117-0121

68
5H-benzofuro[2,3-e]pyrido[3,2-b]indole(5H-benzofuro[2,3-e]pyrido[3,2-b]indole) [ No CAS ]
[ 201731-79-5 ]
C₄₃H₂₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 5H-benzofuro[2,3-e]pyrido[3,2-b]indole(5H-benzofuro[2,3-e]pyrido[3,2-b]indole); 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	6 Synthesis of Compound 3-6, AnT-BeFudC3 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), benzofuro delta-carboline (0.42g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-6, AnT-BeFudC3) 0.52g (yield: 60%) was obtained.
60%	Stage #1: 5H-benzofuro[2,3-e]pyrido[3,2-b]indole(5H-benzofuro[2,3-e]pyrido[3,2-b]indole); 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	6 Synthesis of Compound 3-6 (AnT-BeFudC3) 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), benzofuro delta-carboline (0.42g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature was raised to 80°C and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) and the reaction was performed at 80 °C for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-6, AnT-BeFudC3) 0.52g (yield: 60%) was obtained.
	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	6 3-6 compound (BeFudC3 - AnT)synthesis of 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), benzofuro delta-carboline (0.42g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 °C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.52g (3-6, BeFudC3-AnT)(yield: 60%)is obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0123-0127
[2]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0123-0127
[3]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0123; 0124; 0125; 0126; 0127; 0128

69
C₁₃H₈N₂S [ No CAS ]
[ 201731-79-5 ]
C₃₉H₂₄N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	7 3-7 compound (BeTpP - AnT)synthesis of 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), benzothiophene pyrrolopyridine (0.36g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) toluene (100 ml) of paste has better mouth feeling and it is under, stirring under nitrogen, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 °C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.49g (3-7, AnT-BeTpP)(yield: 61%)is obtained.
61%	Stage #1: C₁₃H₈N₂S; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	7 Synthesis of Compound 3-7, AnT-BeTpP 2-necked 250ml flask into the compound (2) (0.6g, 1.47mmol), benzothiophene pyrrolopyridine (0.36g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) in a toluene (100ml) was stirred under nitrogen, the reaction temperature raising the temperature to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Filtering the solution to remove the toluene by distillation, and separating the concentrated liquid into the column to obtain a compound (3-7, AnT-BeTpP) 0.49g (yield: 61%) was obtained.
61%	Stage #1: C₁₃H₈N₂S; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	7 Synthesis of Compound 3-7 (AnT-BeTpP) 2-necked 250ml flask was charged with compound (2) (0.6g, 1.47mmol), benzothiophene pyrrolopyridine (0.36g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) and toluene (100ml) was stirred under nitrogen into a reaction temperature of raising the temperature to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove and separate the concentrated liquid into the column to obtain a compound (3-7, AnT-BeTpP) 0.49g (yield: 61%) was obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0129; 0130; 0131; 0132; 0133; 0134
[2]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0129-0133
[3]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0129-0133

70
5H-benzo[4,5]thieno[2,3-e]pyrido[3,2-b]indole [ No CAS ]
[ 201731-79-5 ]
C₄₃H₂₆N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere;	8 3-8 compound (BeTpdC3 - AnT)synthesis of 2 opening having composite multi function cap 250 ml(2)(0.6g, 1.47mmol), benzothiophene delta-carboline (0.44g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 °C reacted time at elevated temperatures. Herein Pd (dba)2(0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) 80 °C time in adding an 4-5 reacted. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.55g (3-8, BeTpdC3-AnT)(yield: 62%)is obtained.
62%	Stage #1: 5H-benzo[4,5]thieno[2,3-e]pyrido[3,2-b]indole; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	8 Synthesis of Compound 3-8, AnT-BeTpdC3 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), benzothiophene delta-carboline (0.44g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-8, AnT-BeTpdC3) 0.55g (yield: 62%) was obtained.
62%	Stage #1: 5H-benzo[4,5]thieno[2,3-e]pyrido[3,2-b]indole; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	8 Synthesis of Compound 3-8 (AnT-BeTpdC3) 2-necked 250ml flask, the compound (2) (0.6g, 1.47mmol), benzothiophene delta-carboline (0.44g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature was raised to 80°C and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu)3P (0.01g, 0.06mmol) and the reaction was performed at 80°C for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-8, AnT-BeTpdC3) 0.55g (yield: 62%) was obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0135; 0136; 0137; 0138; 0139; 0140
[2]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0135-0139
[3]Current Patent Assignee: WS CO., LTD. - KR101528768, 2015, B1 Location in patent: Paragraph 0135-0139

71
[ 108-86-1 ]
2-bromo-4a,9a-dihydro-anthraquinone [ No CAS ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-bromo-4a,9a-dihydro-anthraquinone In tetrahydrofuran; hexane at 20℃; for 12h;	1 synthesis of intermediates 7-1 General procedure: Bromobenzene, 5.42 g (34.5 mmol) was dissolved in 60 mL THFnBuLi 13.8 mL (34.5 mmol, 2.5M in hexane) to Then slowly added dropwise at -78 ,It was stirred for 1 hour.To the reaction solution 2-bromo--4a, 9a--dihydro-anthraquinone 4.33g (15.0 mmol)After the dropwise slowly and stirred at room temperature for 12 hours.In 60 mL of water was added to the reaction solutionExtracted three times with 50 mL ethyl acetate and then dried to obtained organic layer with magnesium sulfate. Obtained after evaporation of the solvent the residue 22.4 g KI (135 mmol) and 21.3 g Na2H2PO2 o H2O (165 mmol)And then dissolved in 50 mL acetic acid was stirred for 1 hour at 120 .After cooling the reaction solution to room temperature,Water was added and the resulting residue was filtered through 60 mLWater is separated by silica jelgwan chromatographic purification to give the intermediate I-11 5.05 g (82% yield).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - KR2015/27897, 2015, A Location in patent: Paragraph 0371; 0385; 0386

72
C₃₁H₂₇BN₂O₂ [ No CAS ]
[ 201731-79-5 ]
C₅₁H₃₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 12h;	1 Synthesis of compound 7 General procedure: Intermediate I-4 5.81 g (16.7 mmol), 4 - bromo phenylboronic acid 3.53 g (17.6 mmol), Pd (PPh 3) 4 0.68 g (0.59 mmol)and K2CO34.85 g (35.1 mmol) in THF and 60 mL H2O 30 mLdissolved in the mixture was stirred at 80 for 12 hours.After cooling the reaction solution to room temperature and extracted three times with 30 mL water and 30 mL ethyl acetate.Dry the organic layer obtained therefrom by magnesium sulfate, and purified solvent is evaporated to give a residue was subjected to silica gel column chromatography gave Compound I-6 5.30 g (75% yield).Using intermediate 7-1 instead of Intermediate I-4 except for using the intermediate I-6 in place of 4-bromo phenylboronic acid and is, by using the same method as the synthesis of the intermediate I-5, compound 7 to give the 6.97 g (62% yield).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - KR2015/27897, 2015, A Location in patent: Paragraph 0372; 0387; 0388

73
C₁₃H₁₀N₂O [ No CAS ]
[ 201731-79-5 ]
C₃₉H₂₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: C₁₃H₁₀N₂O; 2-bromo-9,10-diphenylanthracene With sodium t-butanolate In toluene at 80℃; for 1h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 80℃;	5 Synthesis of Compound 3-5, AnT-BeFuP Into a 2-necked 250ml flask was charged with compound (2) (0.6g, 1.47mmol), benzofuro pyrrolopyridine (0.34g, 1.62mmol), NaOtBu (0.42g, 4.41mmol) and toluene (100ml) was stirred under nitrogen and the reaction temperature raising the temperature to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.03g, 0.04mmol), (tert-Bu) 3P (0.01g, 0.06mmol) and the reaction was performed at 80 for 4 to 5 hours. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain a compound (3-5, AnT-BeFuP) 0.5g (yield: 63%) was obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0117-0121

74
C₃₃H₂₇BN₂O₂ [ No CAS ]
[ 201731-79-5 ]
C₅₃H₃₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 12h;	1 Synthesis of Compound 7 3.71 g (7.5 mmol) of Intermediate I-8, 3.07 g (7.5 mmol) of Intermediate 7-1, 0.43 g (0.37 mmol) of Pd(PPh3)4, and 3.11 g (22.5 mmol) of K2CO3were dissolved in a 60 mL of THF/H2O (at a volumetric ratio of 2/1) mixed solution, and then, the mixture was stirred at a temperature of 80° C. for 12 hours. The reaction solution was cooled to room temperature, and then, the resultant solution was extracted three times by using 50 mL of water and 50 mL of acetate. A collected organic layer was dried by using magnesium sulfate, and then, the residual obtained by evaporating the solvent therefrom was separation-purified by silica gel column chromatography to obtain 3.71 g (yield 71%) of Compound 7.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - KR2015/35331, 2015, A Location in patent: Paragraph 0213; 0214; 0233; 0234

75
[ 108-86-1 ]
[ 572-83-8 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 1h;	1.1 500 ml three-neck bottle with magnetic stirringAfter Ar gas replacement, 3.9 g of bromobenzene (molecular weight 156, Ar, 0.025 mol) and 110 ml of THF were added in the above amounts in that order. Add BuLi15ml at -78 °C(2.5 M, 0.0375 mol), after completion, stirring for 15 minutes, keeping -78 ° C or less, and adding 2.25 g of 2-bromoindole (molecular weight 286, 99%, 0.0117 mol). After the addition, vigorously stir, naturally warm to room temperature, and stir at room temperature for 1 hrs.Add 200ml of water to hydrolyze, extract with ethyl acetate, evaporate the solvent, add 200ml of acetic acid, KI20g and sodium hypophosphite 20g, reflux, reaction for 1-2 hours, cool down, room temperature, precipitate, and filter to obtain pale yellow crude product The mixture was washed repeatedly with a mixture of THF and water to HPLC over 97% to give a pale-yellow product 4.44 g, molecular weight 408, yield 93%.
82%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at 20℃; for 12h; Stage #3: With acetic acid at 120℃; for 1h;	1.9 Synthesis of Intermediate 7-1 2.71 g (17.2 mmol) of bromobenzene was dissolved in 50 mL of THF, 6.9 mL (17.2 mmol, 2.5M in hexane) of nBuLi was slowly added thereto at a temperature of -78° C., and then, the resultant mixture was stirred for 1 hour. 2.16 g (7.5 mmol) of 2-bromo-4a,9a-dihydro-anthraquinone was slowly dropped to the reaction solution and then, the resultant reaction solution was stirred at room temperature for 12 hours. 50 mL of water was added to the reaction solution, the resultant solution was extracted there times by using 50 mL of ethylacetate, and then, the obtained organic layer was dried by using magnesium sulfate. 11.2 g (67.5 mmol) of KI and 10.6 g (82.5 mmol) of Na2H2PO2.H2O, which had been prepared by dissolving in 40 mL of an acetic acid, were added to the residual obtained by evaporating the solvent therefrom, and then, the resultant solution was stirred at a temperature of 120° C. for 1 hour. The reaction solution was cooled at room temperature, and then, 50 mL of water was added thereto, and filtered. The obtained residual was separation-purified by using silica gel column chromatography to obtain 5.77 g (yield: 82%) of Intermediate 7-1.
	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran	1.2 Synthesis of Compound 1: Under nitrogen, 5.5 ml of bromobenzene was dissolved in 100 ml of anhydrous tetrahydrofuran,After cooling to -78 ° C, 45 ml of t-butyllithium was added dropwise. After the mixture was stirred for 1 hour, 2-bromoanthraquinone was added.An aqueous ammonium chloride solution was added, extracted with methylene chloride, dried, and the solvent was evaporated under reduced pressure. The product was dissolved in acetic acid, 19 g of potassium iodide and 20 g of NaH2PO2 were added and the mixture was refluxed for 3 hours. Filtration products,The product was washed with water and methanol to give compound 1.

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN104649955, 2018, B Location in patent: Paragraph 0041; 0044; 0045
[2]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - KR2015/35331, 2015, A Location in patent: Paragraph 0213; 0214; 0231; 0232
[3]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN106220571, 2016, A Location in patent: Paragraph 0044

76
9-(naphthalen-1-yl)-7H-benzo[c]carbazole [ No CAS ]
[ 201731-79-5 ]
C₅₂H₃₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate for 12h; Reflux; Inert atmosphere;	4 Synthesis of Compound 42 About 1.5 g (3.6 mmol) of Intermediate F, about 2.5 g (about 7.2 mmole) of Intermediate G, about 40 mg (about 0.18 mol) of Pd(OAc)2, about 108 mg (about 0.54 mmol) of P(t-Bu)3, and about 1.4 g (about 10 mmol) of potassium carbonate (K2CO3) solution were refluxed 14 ml of toluene in a nitrogen atmosphere for about 12 hours. When the reaction was terminated, the solvent was evaporated and removed. The resultant was washed respectively with about 500 ml of ethylacetate and about 500 ml of water. Then an organic layer was collected and dried using anhydrous magnesium sulfate. Then the resultant was isolated by silica chromatography to obtain about 1.3 g of Compound 42 (yield: about 60%).
60%	With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In o-xylene; toluene at 120℃; for 12h; Inert atmosphere;	5 Under nitrogen atmosphere, intermediate F (1.5 g, 3.6 mmol), intermediate G (2.5 g, 7.2 mmole)10 mg of Pd (OAc) 2 (40 mg, 0.18 mol), P (t-Bu) 3 (108 mg, 0.54 mmol) and potassium carbonate K2CO3 (1.4 g, 10 mmol) were refluxed in toluene . After completion of the reaction, the solvent was removed by evaporation, and then 500 ml of ethyl acetate and 500 ml of water were added and washed. The organic layer was collected and dried over anhydrous magnesium sulfate. Subsequently, the resultant was separated by silica chromatography to obtain 1.3 g (yield: 60%) of Compound 42.

Reference： [1]Current Patent Assignee: Samsung Display Co., Ltd.; Sin, Dong Woo; Kim, Myung Sook; Choe, Byung Ki; Kwon, Oh Hyun; Kim, Yoo Jin; Noh, Tae Yong; Lee, Tae Woo - KR2015/20644, 2015, A Location in patent: Paragraph 0285-0287
[2]Current Patent Assignee: SAMSUNG DISPLAY CO., LTD; SIN, DONG WOO; KIM, MYUNG SOOK; CHOE, BYUNG GI; KWON, OH HYUN; KIM, YU JIN; NOH, TAE YONG; LEE, TAE WOO - KR2015/20645, 2015, A Location in patent: Paragraph 0285-0287

77
[ 201731-79-5 ]
1,2-diphenyl-5-[4-(9,10-diphenylanthracen-2-yl)phenyl]-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; triphenylphosphine / tetrahydrofuran; toluene / 10 h

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN106220571, 2016, A

78
[ 120-72-9 ]
[ 201731-79-5 ]
1-(9,10-diphenylanthracen-6-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; XPhos In toluene at 120℃; for 4h; Reflux;	2-bromo-9,10-diphenylanthracene (1.0 mmol), 9H-carbazole (1.5 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.05 mmol), dicyclohexylphosphino-2,4,6-triisopropylbiphenyl(0.08 mmol), sodium tert-butoxide (3.0 mmol) and anhydrous toluene (14 ml) were mixedin a flask. The mixture was refluxed at 120°C for 4 h. After the reaction finished, the reactionmixture was extracted with toluene and washed with water. The organic layerwas driedwithanhydrous MgSO4 and filtered with silica gel. The solution was then evaporated. The crudeproduct was purified recrystallization from CH2Cl2/EtOH

Reference： [1]Kim, Dong Young; Kim, Young Seok; Lee, Song Eun; Kim, Young Kwan; Yoon, Seung Soo [Molecular Crystals and Liquid Crystals, 2017, vol. 644, # 1, p. 197 - 204]

79
C₂₄H₂₁BN₂O₂ [ No CAS ]
[ 201731-79-5 ]
C₄₄H₂₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.6 g	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 1h;	2 Synthesis of Compound 1-93 Compound C (15.3 g, 37.4 mmol) andCompound 1-93a (1.1 eq, 15.7 g) was added to a solution ofDissolved in THF, and potassium carbonate (3 eq, 15.5 g) Dissolved in water and heated and stirred.The catalyst was bis(tri-tert-butylphosphine)palladium (0.005 eq., 100 mg) The reaction was carried out.After about 1 hour, the reaction was completed. After cooling to room temperature, the organic layer was separated using a separating funnelI will separate them. The water was removed using anhydrous magnesium sulfate,After evaporation of the solvent, compound 1-93 (19.6 g, 33.7 mmol) was obtained through column purification

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2017/65974, 2017, A Location in patent: Paragraph 0241; 0242; 0245; 0246

80
2-(dinaphtho[2,1-b: 1’,2’-d]furan-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
[ 201731-79-5 ]
C₄₆H₂₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 12h;	8 Synthesis of Compound 2 General procedure: A solution of 4.97 g (12.6 mmol) of intermediate I-2,3.37 g (12.6 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine,0.73 g (0.63 mmol) of Pd (PPh3) 4 and5.22 g (37.8 mmol) of K2CO3 was dissolved in 80 mL of a THF / H2O solvent mixture (in a volume ratio of 2/1)The reaction solution was stirred at a temperature of 80 ° C for 12 hours.The thus obtained product was cooled to room temperature,The organic layer was extracted three times by using 30 mL of water and 30 mL of ethyl acetate.The organic layer thus collected was dried with magnesium sulfate,The residue obtained after the solvent was evaporated from the silica gel column chromatography was used to separate and purify the residue,To obtain 5.03 g of compound 2 (yield: 80%).The compounds thus produced were determined by using LC-MS and 1H NMR.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - CN106565689, 2017, A Location in patent: Paragraph 0306; 0307; 0314-0316; 0377-0381

81
[ 34907-53-4 ]
[ 201731-79-5 ]
C₃₆H₃₁BO [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3851 - 3854

82
[ 201731-79-5 ]
C₄₆H₃₆BN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 20 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 18 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Mellerup, Soren K.; Häfele, Lisa; Lorbach, Andreas; Wang, Xiang; Wang, Suning [Organic Letters, 2017, vol. 19, # 14, p. 3851 - 3854]

83
[ 201731-79-5 ]
C₄₆H₃₆BN [ No CAS ]
C₄₆H₃₆BN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 20 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 18 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 3.1: benzene-d6 / 300 h / UV-irradiation; Inert atmosphere; Sealed tube

Reference： [1]Mellerup, Soren K.; Häfele, Lisa; Lorbach, Andreas; Wang, Xiang; Wang, Suning [Organic Letters, 2017, vol. 19, # 14, p. 3851 - 3854]

84
[ 952514-79-3 ]
[ 201731-79-5 ]
[ 1073618-22-0 ]

Yield	Reaction Conditions	Operation in experiment
62.33%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 80℃; for 16h;	2-Bromo-9,10-diphenylanthracene (32.76 g, 80 mmol),4- (1-phenyl-1H-benzimidazol-2-yl) benzene acid (4- (. 1-Phenyl-IH-benzimidazol-2-yL)phenylboronic acid) (26.48 g, 88mmol), potassium carbonate (27.64g, 200mmol) and Pd (PPh3. 3). 4(4.64 g) putinto the reaction The flask was further charged with 597 ml of toluene, 97 ml of ethanol and 194 ml of deionized water, stirred and refluxed at 80 C for16 hours.After the reaction was cooled to room temperature, the water layer was removed and concentrated to sticky after adding silica gel 80g, then add tetrahydrofuran,through a silica gel column, rinse the product with toluene, the filtrate was concentrated to a viscous After pouring into a beaker static analysis, filtrationCompound A4 (30 g, 62.33% yield) was obtained asa solid which wasdried in 30 g of a gray solid

Reference： [1]Patent: CN107400116,2017,A .Location in patent: Paragraph 0109-0113

85
[ 201731-79-5 ]
C₅₆H₃₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: n-butyllithium / tetrahydrofuran / 0.25 h 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / Inert atmosphere; Reflux 3: triphenylphosphine / 1,2-dichloro-benzene / 15 h 4: copper(l) iodide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium carbonate; 18-crown-6 ether / 8 h / 175 °C 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / 3 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN104649955, 2018, B

86
[ 201731-79-5 ]
C₃₂H₂₀BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 0.25 h 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN104649955, 2018, B

87
[ 201731-79-5 ]
C₃₂H₂₀BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 0.25 h 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / Inert atmosphere; Reflux 3: triphenylphosphine / 1,2-dichloro-benzene / 15 h

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN104649955, 2018, B

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	201731-79-5	MDL No. :	MFCD14708167
Formula :	C₂₆H₁₇Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OZNXPZBQVNNJCS-UHFFFAOYSA-N
M.W :	409.32	Pubchem ID :	22247163
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 201731-79-5 ] {[proInfo.proName]}

Quality Control of [ 201731-79-5 ]

Related Doc. of [ 201731-79-5 ]

Product Details of [ 201731-79-5 ]

Safety of [ 201731-79-5 ]

Application In Synthesis of [ 201731-79-5 ]

[ 201731-79-5 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry