58473-78-2

Basic information

• Product Name: Benzenamine,4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)-
• Synonyms: 1,1-Bis(4-di-p-tolylaminophenyl)cyclohexane;1,1-Bis(di-4-tolylaminophenyl)cyclohexane;1,1-Bis[4-(di-4-tolylamino)phenyl]cyclohexane;4,4'-Cyclohexylidenebis[N,N-di-p-tolylaniline];ST 755;TAPC
• CAS NO: 58473-78-2
• Molecular Formula: C₄₆H₄₆N₂
• Molecular Weight: 626.87
• EINECS: 261-274-7
• Product Categories: electronic;Electroluminescence;Functional Materials;oled materials
• Mol File: 58473-78-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 186 °C
• Boiling Point: 755 °C at 760 mmHg
• Flash Point: 328.8 °C
• Appearance: /
• Density: 1.118 g/cm³
• Storage Temp.: 2-8°C
• Solubility: soluble in Dimethylformamide,Tetrahydrofuran
• PKA: -1.57±0.60(Predicted)
• CAS DataBase Reference: Benzenamine,4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine,4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)-(58473-78-2)
• EPA Substance Registry System: Benzenamine,4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)-(58473-78-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 58473-78-2(Hazardous Substances Data)

Usage

Applications

1,1-Bis[(di-4-tolylamino)phenyl]cyclohexane, known as TAPC, has been widely used as a hole transport material in organic light-emitting diodes (OLEDs) due to its high hole mobility. Having a higher ET (2.87 eV) than the typical blue phosphorescent guest material, TAPC can be used as both hole-transport layer material and as host for blue phosphorescent (such as FIrpic) guest molecules, resulting in a reduction of the number of organic layers and simplified OLED structures.

Description

1,1-Bis[(di-4-tolylamino)phenyl]cyclohexane, known as TAPC, has been?widely used as a hole transport material in organic light-emitting diodes (OLEDs) due to its?high hole mobility.

Chemical Properties

Light yellow solid

Uses

This material is a popular Hole Transport Layer material for OLED devices.

Synthetic route

4-tolyl iodide (624-31-7) + 1,1-bis-(4-aminophenyl)cyclohexane (3282-99-3) → 1,1-bis[4-(di-p-tolylamino)phenyl]cyclohexane (58473-78-2)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In 1,2-dichloro-benzene at 150℃; for 48h; Inert atmosphere; Schlenk technique;	54%

Upstream product

• 624-31-7 4-tolyl iodide 
• 3282-99-3 1,1-bis-(4-aminophenyl)cyclohexane 

Relevant articles and documents

Tuning the energy level of tapc: Crystal structure and photophysical and electrochemical properties of 4,400-(cyclohexane-1,1-diyl)bis[n,n-bis(4-methoxyphenyl) aniline]

The energy level of a hole-transporting material (HTM) in organic electronics, such as organic light-emitting diodes (OLEDs) and perovskite solar cells (PSCs), is important for device efficiency. In this regard, we prepared 4,40-(cyclohexane-1,1-diyl)bis[N,N-bis(4-methoxyphenyl)aniline] (TAPC-OMe), C46H46N204, to tune the energy level of 4,40-(cyclohexane-1,1-diyl)bis[N,Nbis( 4-methylphenyl)aniline] (TAPC), which is a well-known HTM commonly used in OLED applications. A systematic characterization of TAPC-OMe, including 1H and 13C NMR, elemental analysis, UV-Vis absorption, fluorescence emission, density functional theory (DFT) calculations and single-crystal X-ray diffraction, was performed. TAPC-OMe crystallized in the triclinic space group P1, with two molecules in the asymmetric unit. The dihedral angles between the central amine triangular planes and those of the phenyl groups varied from 26.56 (9) to 60.34 (8) due to the steric hindrance of the central cyclohexyl ring. This arrangement might be induced by weak hydrogen bonds and C-Hπ (Ph) interactions in the extended structure. The emission maxima of TAPC-OMe showed a significant bathochomic shift compared to that of TAPC. A strong dependency of the oxidation potentials on the nature of the electron-donating ability of substituents was confirmed by comparing oxidation potentials with known Hammett parameters (o).