148044-07-9

Basic information

• Product Name: 1,3,5-Tri(9-carbazolyl)benzene
• Synonyms: 1,3,5-TRI(9H-CARBAZOL-9-YL)BENZENE;1,3,5-Tri-(9-carbazolyl)benzene;1,3,5-Tri(9H-carbazol-9-yl)benzene (purified by sublimation);1,3,5-Tri(9-carbazol;TCP , 1,3,5-Tri(9-carbazolyl)benzene;1,3,5-Tri(9H-carbazol-9-yl)benzene, subliMed grade;9H-Carbazole, 9,9',9''-(1,3,5-benzenetriyl)tris-;1,3,5-Tris(N-carbazolyl)benzene
• CAS NO: 148044-07-9
• Molecular Formula: C42H27N3
• Molecular Weight: 573.68
• Product Categories: Electronic Chemicals;Carbazoles;Carbazoles (for Conduting Polymer Research);Electroluminescence;Functional Materials;Highly Purified Reagents;Other Categories;Reagents for Conducting Polymer Research;Refined Products by Sublimation;oled materials
• Mol File: 148044-07-9.mol

Chemical Properties

• Melting Point: 325-330°C
• Appearance: /
• Density: 1.26
• Refractive Index: 1.735
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Tetrahydrofuran
• CAS DataBase Reference: 1,3,5-Tri(9-carbazolyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tri(9-carbazolyl)benzene(148044-07-9)
• EPA Substance Registry System: 1,3,5-Tri(9-carbazolyl)benzene(148044-07-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 148044-07-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Light Emitting Diode (OLED) Industry:
1,3,5-Tri(9-carbazolyl)benzene is used as an advanced host material for phosphorescent guest-host systems in OLED devices. Its electron-rich nature and excellent hole-transporting capabilities contribute to the efficient and bright light emission in these devices, enhancing their performance and energy efficiency.

InChI:InChI=1/C42H27N3/c1-7-19-37-31(13-1)32-14-2-8-20-38(32)43(37)28-25-29(44-39-21-9-3-15-33(39)34-16-4-10-22-40(34)44)27-30(26-28)45-41-23-11-5-17-35(41)36-18-6-12-24-42(36)45/h1-27H

Upstream product

• 108-70-3 1,3,5-trichlorobenzene 
• 86-74-8 9H-carbazole 
• 626-39-1 1,3,5-trisbromobenzene 
• 108-72-5 1,3,5-triaminobenzene 
• 13029-08-8 2,2'-Dichlorobiphenyl 

Relevant articles and documents

Microporous polycarbazole with high specific surface area for gas storage and separation

Microporous polycarbazole via straightforward carbazole-based oxidative coupling polymerization is reported. The synthesis route exhibits cost-effective advantages, which are essential for scale-up preparation. The Brunauer-Emmett-Teller specific surface area for obtained polymer is up to 2220 m2 g-1. Gas (H2 and CO2) adsorption isotherms show that its hydrogen storage can reach to 2.80 wt % (1.0 bar and 77 K) and the uptake capacity for carbon dioxide is up to 21.2 wt % (1.0 bar and 273 K), which show a promising potential for clean energy application and environmental field. Furthermore, the high selectivity toward CO2 over N2 and CH4 makes the obtained polymer possess potential application in gas separation.

Carbazole-triazine based donor-acceptor porous organic frameworks for efficient visible-light photocatalytic aerobic oxidation reactions

We report the synthesis of a series of carbazole-triazine based donor-acceptor (D-A) POFs and their photocatalytic activities for aerobic oxidation reactions. The simultaneous introduction of a carbazole-based electron donor and a triazine-based electron acceptor in D-A POFs stabilizes the charge transfer state and enables an efficient triplet-triplet energy transfer to generate 1O2. Meanwhile, systematic variation of the D-A distance results in the tunable photoredox properties and consequently the efficiency for generation of reactive oxygen species (ROSs). Upon visible light excitation, all three D-A POFs exhibit excellent capability to promote three aerobic oxidations: sulfide oxidation, oxidative amine coupling, and Mannich reactions. This systematic study validates the design principle of D-A POFs as high-performance photo-oxidation catalysts with wide substrate scope and excellent stability and recyclability.

A tuned bicyclic proazaphosphatrane for catalytically enhanced n-arylation reactions with aryl chlorides

The N-arylation of various amines with aryl chlorides proceeded in good-to-excellent yields in the presence of P[N{(p-NMe2)C6H4CH2}CH2CH2]3N (1e, a new electron-rich proazaphosphatrane ligand) and small amounts of Pd2(dba)3 (dba = dibenzylideneacetone). This catalytic system was also very effective for the synthesis of carbazoles. An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.

An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride

An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.

PROCESS FOR PRODUCING N-(HETERO)ARYLAZOLES

The present invention provides a process for effectively producing an N-(hetero)arylazole with high yield, which is useful as a medical or agrochemical product, an organic photoconductor material, an organic electroluminescent element material, or the like. The present invention relates to a process for producing an N-(hetero)arylazole, which includes reacting a (hetero)aryl (pseudo)halide with an NH-azole in the presence of: a catalyst including a palladium compound and a coordination compound; and a basic magnesium compound.

OLED DEVICE WITH CYCLOBUTENE ELECTRON INJECTION MATERIALS

An OLED device including a cathode, an anode, and having therebetween a light-emitting layer and further comprising a first layer between the light-emitting layer and the cathode containing a cyclobutene compound comprising a cyclobutene nucleus substituted in the 1-position with a five- or six-membered heteroaromatic ring group containing at least one trivalent nitrogen atom; substituted in the 2-position with an aromatic ring group; and substituted with a first methylene group in the 3-position and a second methylene group in the 4-position, provided said first and second methylene groups are further disubstituted in the 1′,1′-positions and the 1″,1″-positions with independently selected aromatic groups.

OLED DEVICE EMPLOYING ALKALI METAL CLUSTER COMPOUNDS

The invention provides an OLED device containing certain alkali metal cluster compounds with mixed ligands, such compounds, and methods of making them. In particular, the cluster compound is a neutrally charged mixed cluster compound comprising first and second subunits with the first subunit comprising an alkali metal salt of a nitrogen containing a heterocyclic ligand bearing a anionic hydroxy group and the second subunit consisting of an organic alkali metal salt different than the first subunit.

A new hybrid phosphine ligand for palladium-catalyzed amination of aryl halides

A new hybrid phosphine was designed. The phosphine combines two common structural characteristics found among the effective phosphine ligands reported recently, namely, three tert-alkyl substituents binding to the phosphorus and an aryl group at an appropriate position. A hybrid phospine/palladium system is versatile and effective for the coupling reaction of various aryl halides with primary and secondary amines including carbazole.