3-Bromo-9H-carbazole

CAS Number 1592-95-6

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

A popular building block for the synthesis of dopant or host materials

Used in the application of highly efficient phosphorescent and TADF OLEDs.

Specifications | MSDS | Literature and Reviews

3-Bromo-9H-carbazole, CAS number 1592-95-6, is an isomer to 2-Bromo-9H-carbazole with the only difference being that 9H-carbazole is mono-brominated at 3-position. Blocked at 3-position, 3-Bromo-9H-carbazole derivatives reduce the chance of being oxidised to form excimers or oligomers.

Bipolar host material (PBCz-PO) with an electron donating bi-carbazole core joined at 3,3'-postions and an electron accepting phosphine oxide amide unit, possesses a relatively high triplet energy (2.76 eV) which makes it suitable to be blue host in phosphorescent organic light-emitting diodes. The device with PBCz-PO as a host and FIrpic as a dopant achieved a maximum current efficiency (η_c) of 31.5 cd/A, a maximum power efficiency (η_p) of 31.0 lm/W and a maximum external quantum efficiency (EQE) of 13.4% as well as low driving voltage [1]. Device based on 9'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9,9''-diphenyl-9H,9'H,9''H-3,3':6',3''-tercarbazole (TCzTrz) as the dopant and DPEPO as the host has also gained high device efficiencies with η_c f 39.4 cd/A, η_p of 61.5 lm/W and a maximum external quantum efficiency (EQE) of 31.8%. The device has the following configuration: ITO (50 nm)/PEDOT:PSS (60 nm)/TAPC (20 nm)/mCP (10 nm)/TCzTrz:DPEPO (10 w%) (25 nm)/TSPO1 (5 nm)/TBPi (20 nm)/LiF (1.5 nm)/Al (200 nm).

3-Bromo-9H-carbazole can be prepared by reacting 9H-carbzole with N-bromosuccinimide (NBS) In tetrahydrofuran at room temperature.

General Information

CAS Number	1592-95-6
Chemical Formula	C₁₂H₈BrN
Full Name	3-Bromo-9H-carbazole
Molecular Weight	246.1 g/mol
Synonyms	3-Bromocarbazole
Classification / Family	Carbazoles, semiconductor synthesis intermediates, Electron donor unit, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	198 °C
Appearance	White to off-white powder/crystals

MSDS Documentation

3-Bromo-9H-carbazole MSDS Sheet

Literature and Reviews

A host material consisting of phosphinic amide for efficient sky-blue phosphorescent organic light-emitting diodes, F, Wu et al., Synth. Met., 205, 11-17 (2015); DOI: 10.1016/j.synthmet.2015.03.023.
Carbazole or carbazole-3-carbonitrile /pyridine host materials for efficient solution-processable blue phosphorescent and green TADF OLEDs, C. Tang et al., Opt. Mater., 132, 112573 (2022); DOI: 10.1016/j.optmat.2022.112573.
Carbazole-Based Hole-Transport Materials for High-Efficiency and Stable Perovskite Solar Cells, L. Gao et al., ACS Appl. Energy Mater., 3, 5, 4492–4498 (2020); DOI: 10.1021/acsaem.0c00179.

Engineering of Interconnect Position of Bicarbazole for High External Quantum Efficiency in Green and Blue Phosphorescent Organic Light-Emitting Diodes, M. Kim et al., ACS Appl. Mater. Interfaces, 6, 17, 14874–14880 (2014); 10.1021/am502848c.
Synthesis and Characterization of Telmisartan-Derived Cell Death Modulators to Circumvent Imatinib Resistance in Chronic Myeloid Leukemia, A. Schoepf et al., ChemMedChem, 15, 1067– 1077 (2020); DOI: 10.1002/cmdc.202000092.
Nearly 100% horizontal dipole orientation and up-conversion efficiency in blue thermally activated delayed fluorescent emitters, A. Byeon et al., Adv. Opt. Mater., 6 (15), 1701340 (2018); DOI: 10.1002/adom.201701340.
Cyanopyridine Based Bipolar Host Materials for Green Electrophosphorescence with Extremely Low Turn-On Voltages and High Power Efficiencies, W. Li et al., ACS Appl. Mater. Interfaces, 8, 33, 21497–21504 (2016); DOI: 10.1021/acsami.6b04395..