Am. Chem. Soc. 1977, 99, 5304. [8] Crystal data for DBA(TCNQ) 2 : C 32 H 28 N 9 , M r = 538.63, triclinic, space group P1 (no. 2), a = 6.6650(13) , b = 14.259(3) , c = 15.962(3) ; a = 83.25(3), b = 79.37(3), c = 89.97(3);F(000) = 566, R1 (wR2) = 0.0585 (0.1597) (I > 2r(I)), R1 (wR2) = 0.1233 (0.1788) (all data), GOF = 1.016. Data was collected on a Rigaku RAXIS RAPID IP diffractometer in the range 2.62 < 2B < 27.48 at 293(2) K with graphite-monochromatized Mo Ka radiation (k = 0.71073 ). 6435 reflections measured, 2879 observed with I > 2r(I). The structure was solved by direct methods and successive difference maps (SHELXS-98) and refined by full-matrix least squares on F 2 using all unique data (SHELXL 98). The non-hydrogen atoms were refined anisotropically, while the hydrogen atoms were included in their calculated positions with geometrical constants and refined in the riding model. The highest peaks and holes in the final difference map were 0.242 and ±0.202 e ± ±3 , respectively.CCDC-221 730 contains the supplementary crystallographic data for this paper. This data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ (UK).
A series of copolymers, poly [(9,9-dioctylfluorene-2,7-diyl)-co-(4-dicyanomethylene-2-methyl-6-[4-(diphenylamino)styryl]-4H-pyran-4′,4′′-diyl)], were synthesized by polymerizing 2,7-bis(4,4,5,5tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene with mixtures of 2,7-dibromo-9,9-dioctylfluorene and 4-dicyanomethylene-2-methyl-6-[bis(4′-bromophenyl)amino]styryl]-4H-pyran (a DCM derivative) by the palladium-catalyzed Suzuki coupling reaction. The copolymers were characterized by molecular weight determination, elemental analysis, 1 H NMR, FT-IR spectroscopy, DSC, TGA, UV-vis spectroscopy, and photoluminescence (PL) and electroluminescence (EL) spectroscopy. The copolymers showed two absorption peaks at 380 and 485 nm, and the long-wavelength absorption increased with increasing the fraction of the DCM comonomer. The PL spectra of copolymers in chloroform solution displayed emission from both the main chain (420 nm) and DCM units (620 nm). In the solid state, however, PL spectra of copolymers showed only the long wavelength red emission at 620 nm with no trace of emission from the main chain, which implies a facile exciton migration or energy transfer to the lower energy sites from the fluorene part to the DCM part. This results in emission of only the red light originating from the latter segments. A study on time-resolved PL rise and decay of the polymers clearly supports the energy transfer mechanism. Light-emitting diode (LED) devices were fabricated to have the configuration of ITO (indiumtin oxide)/PEDOT/polymer/Li:Al alloy. EL spectra of the devices showed only red emissions as observed in the PL spectra of the polymers' thin films. EL efficiency decreased with increasing DCM contents. When a tris(8-hydroxyquinolinato)aluminum (Alq 3) layer was inserted between the emitting polymer layer and the cathode to make the ITO/PEDOT/polymer/Alq3/Li:Al alloy configuration, the device efficiencies became much higher (∼10 -2 %) than those (5 × 10 -5 -5 × 10 -3 %) of single-layer devices.
High quantum efficiency blue phosphorescent organic light-emitting diodes were developed using 6- position modified benzofuro[2,3-b]pyridine derivatives as host materials. Two high triplet energy host materials derived from benzofuro[2,3-b]pyridine modified with carbazole or 9-phenylcarbazole were synthesized and the device performances of the host materials were investigated. A high quantum efficiency of 24.3% was achieved using the benzofuro[2,3-b]pyridine host materials due to good charge balance and energy transfer.
A series of poly(oligothienylene vinylenes) (PTmVs, m = 2–4) with a varying number of consecutively bound thienylene rings are successfully prepared in thin films by chemical vapor deposition polymerization (CVDP) using the corresponding bis(halomethyl)thiophenes as starting materials. The chemical and electronic structures are studied spectroscopically and also by cyclic voltammetry. Top‐gate field‐effect transistors are fabricated by two consecutive CVDP cycles of PTmV and poly(p‐xylylene) followed by the deposition of a Au gate electrode. In the case of a PT3V active layer, a field‐effect mobility value of 0.5 × 10–4 cm2 V–1 s–1 is obtained.
A hole‐injection/transport bilayer structure on an indium tin oxide (ITO) layer was fabricated using two photocrosslinkable polymers with different molecular energy levels. Two photoreactive polymers were synthesized using 2,7‐(or 3,6‐)‐dibromo‐9‐(6‐((3‐methyloxetan‐3‐yl)methoxy)hexyl)‐9H‐carbazole) and 2,4‐dimethyl‐N,N‐bis(4‐ (4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)aniline via a Suzuki coupling reaction. When the oxetane groups were photopolymerized in the presence of a cationic photoinitiator, the photocured film showed good solvent resistance and compatibility with a poly(N‐vinylcarbazole) (PVK)‐based emitting layer. Without the use of a conventional hole injection layer (HIL) of poly(3,4‐ethylenedioxythiophene)/(polystyrenesulfonate) (PEDOT:PSS), the resulting green light‐emitting device bearing PVK: 5‐4‐tert‐butylphenyl‐1,3,4‐oxadiazole (PBD):Ir(Cz‐ppy)3 exhibited a maximum external quantum efficiency of 9.69%; this corresponds to a luminous efficiency of 29.57 cd/A for the device K‐4 configuration ITO/POx‐I/POx‐II/PVK:PBD:Ir(Cz‐ppy)3/triazole/Alq3/LiF/Al. These values are much higher than those of PLEDs using conventional PEDOT:PSS as a single HIL. The significant improvement in device efficiency is the result of suppression of the hole injection/transport properties through double‐layered photocrosslinked‐conjugated polymers. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
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