142137-17-5Relevant articles and documents
New sulfone-based electron-transport materials with high triplet energy for highly efficient blue phosphorescent organic light-emitting diodes
Jeon, Soon Ok,Earmme, Taeshik,Jenekhe, Samson A.
, p. 10129 - 10137 (2014)
A series of new electron transport materials, which combines a diphenylsulfone core with different electron withdrawing end groups, has been synthesized, characterized, and found to exhibit high triplet energy (ET > 2.8 eV) for use in phosphorescent organic light emitting diodes (PhOLEDs). The new materials, including 3,3′-(4,4′-sulfonylbis(4,1-phenylene))dipyridine (SPDP), 5,5′-(4,4′-sulfonylbis(4,1-phenylene)) bis(3-phenylpyridine) (SPPP), and 3,3′-(4,4′-sulfonylbis(4,1-phenylene))diquinoline (SPDQ) had wide band gaps (3.6-3.8 eV) and LUMO levels of -2.4 to -2.7 eV. The triplet energy measured from phosphorescence spectra at 77 K varied from 2.53 eV for SPDQ and 2.81 eV for SPPP to 2.90 eV for SPDP, which are in good agreement with density functional theory calculated values. High performance blue PhOLEDs using the sulfone-based materials are exemplified by devices containing a poly(N-vinylcarbazole) host and SPDP electron transport layer, which had a high quantum efficiency (19.6%) and a high current efficiency (33.6 cd A-1) even at very high luminances (4500 cd m-2). These results demonstrate that sulfone-based molecules are promising electron transport materials for application in developing highly efficient phosphorescent OLEDs.
METHOD OF PRODUCING HALOGEN COMPOUND
-
Paragraph 0052-0060; 0085-0087, (2021/05/07)
PROBLEM TO BE SOLVED: To provide a method of efficiently producing an aromatic compound including a halogen group of interest. SOLUTION: A method of producing a halogen compound represented by the specified general formula (1) comprises reacting a compound represented by the specified general formula (2) with a compound represented by the specified general formula (3) in the presence of a transition metal compound, a phosphine compound being 1,1'-bis(diphenylphosphino)ferrocene or 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, and a base. (In the formula, Ar1 and Ar2 represent organic groups; X represents a halogen group; Z represents a halogen group different than X; m represents an integer greater than or equal to 0; p represents an integer greater than or equal to 1; and each R represents a hydrogen atom, alkyl group or phenyl group, where the two R's may be linked together to form a ring.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
C2-Alkenylation of N-heteroaromatic compounds: Via Br?nsted acid catalysis
Crisenza, Giacomo E. M.,Dauncey, Elizabeth M.,Bower, John F.
supporting information, p. 5820 - 5825 (2016/07/06)
Substituted heteroaromatic compounds, especially those based on pyridine, hold a privileged position within drug discovery and medicinal chemistry. However, functionalisation of the C2 position of 6-membered heteroarenes is challenging because of (a) the difficulties of installing a halogen at this site and (b) the instability of C2 heteroaryl-metal reagents. Here we show that C2-alkenylated heteroaromatics can be accessed by simple Br?nsted acid catalysed union of diverse heteroarene N-oxides with alkenes. The approach is notable because (a) it is operationally simple, (b) the Br?nsted acid catalyst is cheap, non-toxic and sustainable, (c) the N-oxide activator disappears during the reaction, and (d) water is the sole stoichiometric byproduct of the process. The new protocol offers orthogonal functional group tolerance to metal-catalysed methods and can be integrated easily into synthetic sequences to provide polyfunctionalised targets. In broader terms, this study demonstrates how classical organic reactivity can still be used to provide solutions to contemporary synthetic challenges that might otherwise be approached using transition metal catalysis.
