37500-95-1

Basic information

• Product Name: 3,6-BIS(TERT-BUTYL)CARBAZOLE
• Synonyms: 3,6-BIS(TERT-BUTYL)CARBAZOLE;3,6-Di-tert-butyl-9H-carbazole;3,6-Ditert-butyl-9H-carbazole;3,6-Di-tert-butylcarbazole;9H-Carbazole, 3,6-bis(1,1-diMethylethyl)-;3,6-Di-tert-butylcarbazole≥ 99% (GC)
• CAS NO: 37500-95-1
• Molecular Formula: C₂₀H₂₅N
• Molecular Weight: 279.42
• Mol File: 37500-95-1.mol

Chemical Properties

• Melting Point: 233-235℃
• Boiling Point: 424.2±14.0 °C(Predicted)
• Appearance: /
• Density: 1.037
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 17.70±0.30(Predicted)
• CAS DataBase Reference: 3,6-BIS(TERT-BUTYL)CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-BIS(TERT-BUTYL)CARBAZOLE(37500-95-1)
• EPA Substance Registry System: 3,6-BIS(TERT-BUTYL)CARBAZOLE(37500-95-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 37500-95-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Light Emitting Diodes (OLEDs):
3,6-BIS(TERT-BUTYL)CARBAZOLE is used as a monomeric precursor for synthesizing new carbazole-based materials, such as 9-(4-bromophenyl)-3,6-di-tert-butylcarbazol and 2-(4-(2-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)ethynyl)benzylidene)malononitrile (PBM). These materials are specifically designed for use in organic light-emitting diodes (OLEDs), where they contribute to enhanced device performance and efficiency.
Used in Optical Switching Devices:
In addition to OLEDs, 3,6-BIS(TERT-BUTYL)CARBAZOLE and its derived materials are also utilized in the development of optical switching devices. These devices benefit from the compound's hole transporting characteristics, which enable efficient control of light transmission and modulation in various applications.
Used in the Synthesis of Novel Electroluminescent Materials:
3,6-BIS(TERT-BUTYL)CARBAZOLE can be combined with other carbazole materials to create innovative electroluminescent materials. These materials have potential applications in advanced display technologies and other optoelectronic devices, where their unique properties can be harnessed to improve performance and functionality.

Upstream product

• 91801-97-7 N-(2-bromo-4-tert-butylphenyl)acetamide 
• 103273-01-4 2-bromo-4-tert-butylaniline 
• 507-19-7 t-butyl bromide 
• 86-74-8 9H-carbazole 
• 507-20-0 tertiary butyl chloride 
• 7646-85-7 zinc(II) chloride 
• 34601-54-2 1,3,6,8-tetra-tert-butyl-9H-carbazole 

Downstream Products

• 1430420-21-5 9,9'-(9-phenyl-9-(9-phenyl-9H-carbazol-3-yl)-9H-fluorene-3,6-diyl)bis(3,6-di-tert-butyl-9H-carbazole) 
• 1394038-61-9 3,6-di-tert-butyl-9-(p-tolyl)-9H-carbazole 
• 1134188-18-3 [9-(3-bromophenyl)]-3,6-di-tert-butyl-9H-carbazole 
• 1263359-87-0 3,6-di-tert-butyl-1,8-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 
• 1510810-80-6 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 

Relevant articles and documents

Preorganized anion traps for exploiting anion-π interactions: An experimental and computational study

1,3-Bis(pentafluorophenyl-imino)isoindoline (AF) and 3,6-di-tert-butyl-1,8-bis(pentafluorophenyl)-9H-carbazole (BF) have been designed as preorganized anion receptors that exploit anion-π interactions, and their ability to bind chlor

Creation of cationic iridium(iii) complexes with aggregation-induced phosphorescent emission (AIPE) properties by increasing rotation groups on carbazole peripheries

Three cationic iridium complexes containing 4,7-bis(3,6-di-tert-butyl-9H- carbazol-9-yl)-1,10-phenanthroline (L1) and 4,7-bis(3′, 6′-di-tert-butyl-6-(3,6-di-tert-butyl-9H-carbazol-9-yl)-3, 9′-bi(9H-carbazol)-9-yl)-1,10-phenanthroline (L2/

Carbazole based polymers as hosts for blue iridium emitters: Synthesis, photophysics and high efficiency PLEDs

This article reports the synthesis of new carbazole based polymers and their application as hosts in sky-blue polymer light emitting devices (PLEDs) with a solution-processed emitting layer doped with a cyclometalated Ir(iii) complex. We systematically investigate their effect on the PLED performance. A current efficiency of 19.7 cd A-1 and a brightness of 1850 cd m -2 were achieved with these polymers. The roll-off in electrophosphorescent quantum efficiency in PLEDs was shown to arise mainly from triplet-triplet annihilation between dopants in the hosts with tert-butyl groups. It has been shown that in the devices with hosts without tert-butyl groups the efficiency roll-off is additionally affected by electric field quenching. In these carbazole based polymers, triplet dimers are formed and tert-butyl groups do not limit the intermolecular interactions to prevent triplet dimer formation, nevertheless tert-butyl groups reduce charge transport.

A route to a cyclobutane-linked double-looped system: Via a helical macrocycle

Macrocycles built of carbazole and pyridine fragments with alkene/alkane linkers constitute a helical structure as documented structurally and spectroscopically. The 'solid-state' prearrangement observed for two CC bonds leads to unprecedented transformation to a cyclobutane in a head-to-tail (rtct) geometry with two macrocyclic loops in a perpendicular orientation.

Methoxy- and tert-butyl-substituted meta-bis(N-carbazolyl)phenylenes as hosts for organic light-emitting diodes

Two new analogues of a popular host material, meta-bis(N-carbazolyl)phenylene (mCP), bearing either methoxy- (mCP-OMe) or tert-butyl (mCP-t-Bu) substituents at C-3 and C-6 positions of carbazole moieties were synthesized and characterized. These materials exhibit higher glass-transition temperatures (79 and 145 °C) than mCP (67 °C). They show reversibility upon electrochemical oxidation while preserving high enough triplet energy levels (2.86 and 2.97 eV). The vacuum-deposited layer of mCP-t-Bu showed hole mobility of 8 × 10?3 cm2V?1s?1 at the electric field of 1.2 × 105 Vcm?1. This value is more than by one order of magnitude higher than that of mCP. The new compounds were tested as hosts for commercial emitters: blue phosphor, bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic), green and blue thermally-activated delayed fluorescence (TADF) emitters 1,2,3,5-tetrakis(9-carbazolyl)-4,6-dicyanobenzene (4CzIPN) and bis[4-(9,9-dimethyl-9,10-dihydroacridin-10-yl)phenyl]sulfone (DMAC-DPS). Blue phosphorescent OLED based on mCP-t-Bu as the host showed up to 22.0% external quantum efficiency. When doping 4CzIPN into mCP-OMe host, a broad emission with peaks at 388, 514, and 572 nm was observed.

Synthesis and characterization of starburst 9-phenylcarbazole/triazatruxene hybrids

Novel starburst triazatruxenes functionalized with six N-phenylated carbazole units have been synthesized and characterized. Good yields and high purity were readily obtained via an optimized microwave-enhanced six-fold Suzuki coupling methodology. High thermal stability and good amorphous properties as well as deep blue emissions (423-434 nm) were demonstrated. The introduction of six-substituted triazatruxene scaffolds could provide a new guideline for exploring novel solution-processable amorphous materials with dual functions for light-emitting and/or hole-transporting applications. Copyright

Thermally activated delayed fluorescence enantiomers for solution-processed circularly polarized electroluminescence

Circularly polarized organic light-emitting diodes (CP-OLEDs) with thermally activated delayed fluorescence (TADF) characteristics are receiving increasing interest, as they have shown improving efficiencies of circularly polarized electroluminescence (CPEL). Here, we developed a series of TADF enantiomers based on chiral binaphthalene, an acceptor (A) of cyanopyridine, and donors (D) of carbazoles in a chiral-A-D architecture. Good solubility, high luminescence yields, and excellent chiral stability with a photoluminescence dissymmetry factor (gPL) up to 5.8 × 10-4 were achieved. Efficient CP-OLEDs using these chiral TADF molecules as dopants were successfully fabricated, exhibiting high external quantum efficiencies (EQEs) up to 12.4% and opposite CPEL signals with gEL of 6 × 10-4/-8.6 × 10-4 in vacuum-deposited devices. More impressively, the solution-processed TADF CP-OLEDs result in much larger gEL values (3.5 × 10-3/-3.9 × 10-3) with EQEs up to 10.6%. This discovery is encouraging and instructive, which could stimulate the development of high-performance CP-OLEDs using chiral TADF molecules through solution-processing approaches.

Ideal bipolar host materials with bis-benzimidazole unit for highly efficient solution-processed green electrophosphorescent devices

An ideal host material with high triplet energy, suitable HOMO energy level, excellent thermal and electrochemical stability, and bipolar charge carrier transport ability was synthesized. A high external quantum efficiency of 13.7% and a luminance e ffici

Solution-processible carbazole dendrimers as host materials for highly efficient phosphorescent organic light-emitting diodes

A group of dendrimers with oligo-carbazole dendrons appended at 4,4′- positions of biphenyl core are synthesized for use as host materials for solution-processible phosphorescent organic light-emitting diodes (PHOLEDs). In comparison with the traditional

Carbazole-containing porphyrinoid and its oligomers

A novel carbazole-containing porphyrinoid 4H and its oligomers 6H and 7H were synthesized for the first time via the Suzuki-Miyaura cross-coupling reaction. The structures of 4H, 4Pd, 6H, and 6Zn were finally confirmed by X-ray analysis. The exciton coupl