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N4,N4'-Diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine
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[ CAS No. 887402-92-8 ]

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Chemical Structure| 887402-92-8
Chemical Structure| 887402-92-8
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Product Details of [ 887402-92-8 ]

CAS No. :887402-92-8 MDL No. :MFCD16036285
Formula : C60H42N4 Boiling Point : -
Linear Structure Formula :- InChI Key :MESMXXUBQDBBSR-UHFFFAOYSA-N
M.W :819.00 Pubchem ID :57355319
Synonyms :

Safety of [ 887402-92-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 887402-92-8 ]

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

  • Downstream synthetic route of [ 887402-92-8 ]

[ 887402-92-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 531-91-9 ]
  • [ 502161-03-7 ]
  • C60H42N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h; 912 mg (2.47 mmol) of the intermediate compound B, 336.4 mg (1 mmol) of the intermediate compound C, 300 mg (3 mmol) of t-BuONa, 40 mg (0.02 mmol) of Pd2(dba)3, and 3 mg (0.01 mmol) of P(t-Bu)3 were dissolved in 5 mL of toluene, and then stirred at 90C for 3 hrs. After the reaction was completed, the resultant was cooled to room temperature and three times extracted with distilled water and diethyl ether. The collected organic layer was dried on magnesium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography to obtain 570 mg of Compound represented by Formula 3 as a yellow solid (yield: 70%). 1H NMR (CDCl3, 300MHz) delta (ppm) 7.99 (d, 2H), 7.95 (s, 2H), 7.61-7.57 (m, 8H), 7.48-7.32 (m, 12H), 7.27-7.19 (m, 8H), 7.18-7.10 (m, 8H), 6.96 (t, 2H); 13C NMR (CDCl3, 100MHz) delta (ppm) 148.4, 147.3, 141.3, 140.4, 138.0, 137.6, 133.9, 129.9, 129.1, 127.4, 127.1, 127.0, 126.1, 125.6, 124.3, 123.0, 122.9, 122.8, 121.7, 120.5, 119.9, 118.5, 110.7, 109.9. The obtained Compound represented by Formula 3 was diluted with CHCl3 to a concentration of 0.2 mM and the UV spectrum therefor was obtained. A maximum absorption wavelength of 351 nm was observed in the UV spectrum (FIG. 2). Further, Compound represented by Formula 3 was subjected to thermal analysis using TGA (Thermo Gravimetric Analysis) and DSC (Differential Scanning Calorimetry) (N2 atmosphere, temperature range: room temperature-600C (10C/min)-TGA, room temperature-400C - DSC, Pan type: Pt pan in disposable Al pan (TGA), disposable Al pan (DSC)) to obtain Td 494C and Tg 153C (FIGS. 3 and 4). A HOMO (Highest Occupied Molecular Orbital) energy level of 5.16 eV and a LUMO (Lowest Occupied Molecular Orbital) energy level of 2.16 eV were obtained using UV absorption spectrum and a potentiometer AC-2.
Reference： [1]Patent: EP1661888,2006,A1 .Location in patent: Page/Page column 11-12
  • 2
  • [ 887402-92-8 ]
  • [ 2099702-37-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.17 h 1.2: 4 h / 60 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C 2.2: 2 h / -78 - 20 °C
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2017/63363, 2017, A
  • 3
  • [ 887402-92-8 ]
  • [ 672939-20-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.17 h 1.2: 4 h / 60 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; water
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2017/63363, 2017, A
  • 4
  • [ 887402-92-8 ]
  • [ 2099702-48-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 0.17 h 1.2: 4 h / 60 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; water 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 3.2: 6 h / 70 °C
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2017/63363, 2017, A
  • 5
  • [ 887402-92-8 ]
  • [ 68-12-2 ]
  • [ 2099702-65-3 ]
YieldReaction ConditionsOperation in experiment
6.82g Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.166667h; Stage #2: C60H42N4 In 1,2-dichloro-ethane at 60℃; for 4h; 7.1 Preparation of the compound of the formula E-6 In a 250 mL reaction flask, 16 mL of DMF was added and stirred for 10 minutes, POCl3 (3.4 mL, 36.6 mmol) was added,The mixture was stirred for 10 minutes to prepare a vilsmeier reagent.Compound (E-5) (10 g, 12.2 mmol) was dissolved in 120 ml of 1,2-dichloroethane,The resulting vilsmeier reagent was added and stirred at 60 ° C for 4 hours.Water was added to the reaction vessel, stirred for another 1 hour, and then extracted with DCM.The organic solution was dried over MgSO4, filtered and then removed with a vacuum rotary evaporator. Purification by column chromatography (developing solvent DCM / Hexane = 1: 2 to 1: 1) yielded 6.82 g of the compound of formula E-6.
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2017/63363, 2017, A Location in patent: Paragraph 0396-0399
  • 6
  • [ CAS Unavailable ]
  • [ 887402-92-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane at 20℃; for 20h; Inert atmosphere; 1-1 Production Example 1-1. Preparation of 3-31 500 mL of dichloromethane was added to the compound of formula (A) (5.00 g, 6.10 mmol) under nitrogen atmosphere, and the mixture was stirred. Silver hexafluoroantimonate (2.05 g, 6.00 mmol) was added thereto and stirred at room temperature for 20 hours. After passing through a celite pad, dichloromethane was removed from the evaporator, and the residue was dissolved in dichloromethane (200 mL) and ethyl acetate (300 mL). Water (400 mL) was added thereto and washed with water. The organic layer was separated and concentrated using an evaporator. After vacuum drying, black powder (5.29 g, yield 82%) was obtained.
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2018/44720, 2018, A Location in patent: Paragraph 0302-0304
YieldReaction ConditionsOperation in experiment
67% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium tertiary butoxide In toluene Reflux; 5 Synthesis Example 1: Synthesis of Compound 37 General procedure: In a round-bottom flask, 5.0g of 3-bromo-9-phenyl-9H-carbazole (3-bromo-9-phenyl-9H-carbazole), 4.0g of N1, N4-diphenylbenzene-1,4-diamine (N1, N4-diphenylbenzene-1,4-diamine), 2.3g of t-BuONa, 0.6g of Pd2 (dba)3 After 0.7 ml (t-Bu) 3P was dissolved into 150 ml of toluene, reflux stirring was carried out. The reaction was confirmed using Thin Layer Chromatography (TLC) and ended after the addition of water. The organic layer is extracted by MC (dichloromethane (Methylene chloride) and recrystallized after filtering under reduced pressure to obtain 7.8g of compound 37. (Yield 68%)
... had a five-layered organic thin layer, and specifically the following structure.ITO/Compound A (700 Å)/Compound B (50 Å)/Compound C (1,020 Å)/EML[Compound 1B-4-4:Compound 68:PhGD (10 wt %)] (400 Å)/Compound D:Liq (300 Å)/Liq (15 Å)/Al (1,200 Å).Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamineCompound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amineCompound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline
  • 8
  • [ 591-50-4 ]
  • [ 887402-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 18-crown-6 ether; potassium carbonate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide / 8 h / 170 °C 2: periodic acid; acetic acid; iodine / 2 h / 80 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 90 °C
Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2020/266354, 2020, A1
  • 9
  • [ 1150-62-5 ]
  • [ 887402-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: periodic acid; acetic acid; iodine / 2 h / 80 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 90 °C
Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2020/266354, 2020, A1
  • 10
  • [ 86-74-8 ]
  • [ 887402-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 18-crown-6 ether; potassium carbonate; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide / 8 h / 170 °C 2: periodic acid; acetic acid; iodine / 2 h / 80 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 90 °C
Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2020/266354, 2020, A1

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