192198-85-9

Basic information

• Product Name: 1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene
• Synonyms: 1,3,5-TRIS(1-PHENYL-2-BENZIMIDAZOLYL)BENZENE;TBPI;1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene;1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzene;2,2',2''-(1,3,5-Benzenetriyl)tris[1-phenyl-1H-benzimidazole];TPBi;2,2',2" -(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole);1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl
• CAS NO: 192198-85-9
• Molecular Formula: C45H30N6
• Molecular Weight: 654.76
• EINECS: 1312995-182-4
• Product Categories: oled materials;OLED
• Mol File: 192198-85-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 272-277°C
• Appearance: /
• Density: 1.26
• Refractive Index: 1.727
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.25±0.10(Predicted)
• CAS DataBase Reference: 1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene(192198-85-9)
• EPA Substance Registry System: 1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene(192198-85-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 192198-85-9(Hazardous Substances Data)

Usage

Applications

2,2',2"-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), TPBi, being electron deficient, is normally used as electron transport layer material in optoelectronic devices. Having a low LUMO energy level (2.7 eV), TPBi is also used as host material for both fluorescent and phosphorescent light emitting systems. In some cases, TPBI is used to replace CBP (HBL)/Alq3 (ETL) to simplify the device structure for its excellent electron transporting and also its hole blocking abilities with very deep HOMO energy level (HOMO = 6.2/6.7 eV). It has also been reported that TPBi could be used as electron injection layer material between Alq3 (ETL) and Cs2O3/Al (electrode). It suggested that TPBI thin layer at the Alq3/Cs2O3 interface facilitates the electron injection and is also involved with hole-blocking and exciton confinement.

Description

2,2',2''-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), TPBi, being electron deficient, is normally used as electron transport layer material in optoelectronic devices.?Having a low LUMO energy level (2.7 eV), TPBi is also used as host material for both fluorescent and phosphorescent light emitting systems.

Uses

Used in OLED′s devices as electron transport and exciton blocking materials.

InChI:InChI=1/C45H30N6/c1-4-16-34(17-5-1)49-40-25-13-10-22-37(40)46-43(49)31-28-32(44-47-38-23-11-14-26-41(38)50(44)35-18-6-2-7-19-35)30-33(29-31)45-48-39-24-12-15-27-42(39)51(45)36-20-8-3-9-21-36/h1-30H

Upstream product

• 4422-95-1 1,3,5-benzene tris(carbonyl chloride) 
• 534-85-0 N-phenyl-1,2-benzenediamine 
• 950766-71-9 N¹,N³,N⁵-tris(2-(phenylamino)phenyl)benzene-1,3,5-tricarboxamide 

Relevant articles and documents

A low-cost phenylbenzoimidazole containing electron transport material for efficient green phosphorescent and thermally activated delayed fluorescent OLEDs

A new phenylbenzoimidazole-based electron-transport material (ETM), 2,4,6-tris(2-phenyl-1H-benzo[d]imidazol-1-yl)benzonitrile (iTPBI-CN), is designed and synthesized through a simple low-cost one-step C-N coupling reaction by using 2,4,6,-trifluorobenzonitrile and 2-phenyl-1H-benzo[d]imidazole as the starting materials. In comparison with the four step synthesis of commercial ETM of 2,2,2-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TBPI), the introduction of a cyano moiety into iTPBI-CN greatly simplifies the synthetic procedure and allows for an isomerized linkage of phenylbenzoimidazole. The glass transition temperature increases from 124 °C of TPBI to 139 °C of iTPBI-CN. Both compounds show similar HOMO levels of ～5.9 eV and a triplet energy of ～2.6 eV. The deeper LUMO level of iTPBI-CN (2.79 eV) than TPBI (2.38 eV) allows for more efficient electron-injection and a much higher device efficiency. Solution-processed green phosphorescent OLEDs with the structure of ITO/PEDOT:PSS/host:Ir(mppy)3/iTPBI-CN versus TPBI/LiF/Al show maximum current and power efficiencies of 37.7 cd A-1 and 29.0 lm W-1versus 26.1 cd A-1, 12.2 lm W-1 in the CBP host and 31.3 cd A-1 and 23.9 lm W-1versus 20.6 cd A-1, 7.4 lm W-1 in the mCP host. Furthermore, the superior device performance of iTPBI-CN over TPBI is also found in both CBP and mCP hosted green thermally activated delayed fluorescence (TADF) devices by using 2,3,5,6-tetracarbazole-4-cyano-pyridine (4CzCNPy) as a dopant.

Method for Synthesizing 1,3,5-Tri-(N-Phenylbenzimidazolyl) Benzene

The present invention relates to efficient synthetic method of 1,3,5-tris (N-Phenylbenzimidazole) Benzene and pertains to the field of synthesis of organic light-emitting materials. The method and process of the patent are as following: 1,3,5-tris (N-Phen

Methods of making tris(N-aryl benzimidazoles)benzenes and their use in electronic devices

Provided are methods for preparing a compound of Formula I: where the method comprises the steps of: contacting a compound of Formula II: with 1,3,5-benzene-tricarbonyl chloride in the presence of a polar aprotic solvent to form an amide adduct; and subse