550378-78-4

Basic information

• Product Name: 9,9'-(1,3-Phenylene)bis-9H-carbazole
• Synonyms: 1,3-Di(9H-carbazol-9-yl);9H-carbazole-9,9’-(1,3-phenylene)- bis-(9C1);1,3-Bis(carbazol-9-yl)benzene;1,3-Bis(N-carbazolyl)benzene;9,9'-(1,3-Phenylene)bis-9H-carbazole;N,N'-Dicarbazolyl-3,5-benzene;1,3-di(9H-carbazol-9-yl)benzene;9,9'-(1,3-Phenylene)
• CAS NO: 550378-78-4
• Molecular Formula: C30H20N2
• Molecular Weight: 408.49
• Product Categories: oled materials;Hole Injection Layer (HIL) Materials;Hole Transport (HT) &Hole Transport Materials;Host Materials;Phosphorescent Host Materials;Building Blocks;Carbazoles;Chemical Synthesis;Heterocyclic Building Blocks;Materials Science;OLED and PLED Materials;Organic and Printed Electronics
• Mol File: 550378-78-4.mol

Chemical Properties

• Melting Point: 176-178°C
• Boiling Point: 644.203 °C at 760 mmHg
• Flash Point: 343.402 °C
• Appearance: /
• Density: 1.21
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 9,9'-(1,3-Phenylene)bis-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9'-(1,3-Phenylene)bis-9H-carbazole(550378-78-4)
• EPA Substance Registry System: 9,9'-(1,3-Phenylene)bis-9H-carbazole(550378-78-4)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36/37/39-41-37/38
• WGK Germany: 3
• Hazardous Substances Data: 550378-78-4(Hazardous Substances Data)

Usage

Uses

1. Used in Phosphorescent Host Material:
9,9'-(1,3-Phenylene)bis-9H-carbazole is used as a phosphorescent host material for its high triplet energy and deep HOMO level, which contribute to efficient blue phosphorescent light-emitting diodes (OLEDs). Kawamura et al. demonstrated that the photoluminescence internal quantum yield of the blue emitter FIrpic could approach nearly 100% when doped into the wide energy gap host of mCP.
2. Used in Electronics Industry:
In the electronics industry, 9,9'-(1,3-Phenylene)bis-9H-carbazole is used as a key component in the development and manufacturing of OLEDs. Its properties make it suitable for enhancing the performance and efficiency of these devices, leading to better display technology and energy-saving lighting solutions.
3. Used in Research and Development:
9,9'-(1,3-Phenylene)bis-9H-carbazole is also utilized in research and development for the exploration of new materials and technologies related to phosphorescent applications. Its unique properties make it an interesting subject for scientists and engineers working on innovative solutions in the field of optoelectronics.

Upstream product

• 626-00-6 1,3-Diiodobenzene 
• 86-74-8 9H-carbazole 
• 541-73-1 1,3-Dichlorobenzene 
• 108-36-1 1,3-dibromobenzene 
• 13029-09-9 2,2'-dibromobiphenyl 
• 108-45-2 m-phenylenediamine 
• 583-53-9 2,3-dibromobenzene 
• 2113-51-1 2-iodobiphenyl 

Relevant articles and documents

Palladium-catalyzed C-H bond activation for the assembly of: N -aryl carbazoles with aromatic amines as nitrogen sources

A convenient and efficient palladium-catalyzed C-H bond activation for the assembly of N-aryl carbazole is reported, in which two C-N bonds were formed under one set of conditions. The desired carbazoles were achieved in decent yields with a wide substrate scope by utilizing readily available 2-iodo biphenyls and aromatic amines as starting materials.

Preparation method of 1,3-dicarbazolyl benzene

The invention provides a preparation method of 1,3-dicarbazolyl benzene, which is characterized in that 1,3-dichlorobenzene and carbazole are effectively coupled to generate 1,3-dicarbazolyl benzene (mCP) under the action of a tri(aryl phosphine) coordinated palladium catalyst and an organic magnesium reagent. The method is characterized in that a tri(aryl phosphine) having the general formula Ia,Ib or mixtures thereof is used as a supporting ligand for the palladium catalyst.

1,3-biscarbazolyl benzene type phosphorescent host material, and synthesis method and application thereof

The invention discloses a 1,3-biscarbazolyl benzene type phosphorescent host material, and a synthesis method and application thereof, and belongs to the technical field of optoelectronic material application. The blue phosphorescent host material adoptin

Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions

A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.

Solution-processable highly efficient deep-red and orange organic light-emitting diodes based on multi-functional Ir(III) complexes

A heteroleptic deep-red iridium(iii) complex, TPQIr-HT, based on thiophene-phenylquinoline (TPQ), and orange Ir(iii) complexes, m-CF3DPQIr-HT and m-CF3DPQIr-ET based on diphenylquinoline (DPQ), are designed by attaching a carbazole-based hole transporting (HT) group and an oxadiazole (OXD)-based electron transporting (ET) group to the parent Ir(iii) complexes, TPQIr and m-CF3DPQIr. The Ir(iii) complexes TPQIr-HT show a deep-red emission peak at 612 nm, similar to that of TPQIr, whereas m-CF3DPQIr-HT and m-CF3DPQIr-ET show an orange emission peak at 567 ± 1 nm, which is similar to that of m-CF3DPQIr. The newly functionalized Ir(iii) complexes show improved device performance compared to the Ir(iii) complexes, TPQIr and m-CF3DPQIr, without the additional functional groups. The phosphorescent organic light-emitting diodes (PhOLEDs) fabricated using a deep-red Ir(iii) complex, TPQIr-ET, achieved a maximum external quantum efficiency (EQE) of 17.47% using GraHIL as the hole injection layer (HIL). Similarly, the orange Ir(iii) complex, m-CF3DPQIr-HT, achieved a maximum EQE of 21.61%.

Novel organic semiconductors based on phenyl and phenylthienyl derivatives for organic thin-film transistors

New phenyl and phenylthienyl derivatives end-functionalized with carbazole and α-carboline, 9-(4- (9H-carbazol-9-yl)phenyl)-9H-carbazole, 9-(4-(9H-carbazol-9-yl)phenyl)-9H-pyrido[2,3-b]indole, 9- (3-(9H-carbazol-9-yl)phenyl)-9H-carbazole, 9-(3-(9H-carbazol-9-yl)phenyl)-9H-pyrido[2,3-b]indole, 9-(4-(5-(9H-carbazol-9-yl)thiophen-2-yl)phenyl)-9H-carbazole, and 9-(3-(5-(9H-carbazol-9-yl) thiophen-2-yl)phenyl)-9H-carbazole were synthesized and characterized as organic semiconductors for organic thin-film transistors (OTFTs). Most compounds exhibited p-channel characteristics with carrier mobility as high as 1.7 × 10-5 cm2/Vs and a current on/off ratio of 102-104 for top-contact/bottom-gate OTFT devices.

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.

Carbazole-based hole transport and/or electron blocking materials and/or host polymer materials

This invention relates generally to norbornene-monomer, poly(norbornene)homopolymer, and poly(norbornene)copolymer compounds containing a functionalized carbazole side chain, having desirable solution processability and host characteristics. It also relates to hole transport and/or electron blocking materials, and to organic host materials for an organic luminescence layer, an OLED device, and compositions of matter which include these compounds.

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.