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1.
Chemistry ; 30(37): e202401250, 2024 Jul 02.
Artículo en Inglés | MEDLINE | ID: mdl-38705864

RESUMEN

9,9-Dimethyl-9,10-dihydroacridine (DMAC) is one of the most widely used electron donor for constructing high-performance thermally activated delayed fluorescence (TADF) emitters. However, DMAC-based emitters often suffer from the imperfect color purity, particularly in blue emitters, due to its strong electron-donating capability. To modulate donor strength, 2,7-F-Ph-DMAC and 2,7-CF3-Ph-DMAC were designed by introducing the electron-withdrawing 2-fluorophenyl and 2-(trifluoromethyl)phenyl at the 2,7-positions of DMAC. These donors were used, in combination with 2,4,6-triphenyl-1,3,5-triazine (TRZ) acceptor, to develop novel TADF emitters 2,7-F-Ph-DMAC-TRZ and 2,7-CF3-Ph-DMAC-TRZ. Compared to the F- or CF3-free reference emitter, both two emitters showed hypsochromic effect in fluorescence and comparable photoluminescence quantum yields without sacrificing the reverse intersystem crossing rate constants. In particular, 2,7-CF3-Ph-DMAC-TRZ based OLED exhibited a blue shift by up to 39 nm and significantly improved Commission International de l'Éclairage (CIE) coordinates from (0.36, 0.55) to (0.22, 0.41), while the external quantum efficiency kept stable at about 22.5 %. This donor engineering strategy should be valid for improving the color purity of large amount of acridine based TADF emitters. It can be predicted that pure blue TADF emitters should be feasible if these F- or CF3-modifed acridine donors are combined with other weaker electron acceptors.

2.
Chemistry ; 30(4): e202303169, 2024 Jan 16.
Artículo en Inglés | MEDLINE | ID: mdl-37965803

RESUMEN

In general, a large donor-acceptor dihedral angle is required to guarantee sufficient frontier molecular orbitals separation for thermally activated delayed fluorescence (TADF) emitters, which is intrinsically unfavorable for the radiative transition. We present a molecular design method favoring both reverse intersystem crossing (RISC) and radiative transitions even at a moderate D-A angle. A blue TADF emitter TrzBuCz-CN was designed with triazine/tert-butylcarbazole as donor/acceptor and cyano (CN) incorporated on the phenylene bridge. In comparison with the methyl decoration in similar way (TrzBuCz-Me), CN decoration reduced the D-A dihedral angle from 70° to 60°, which is intrinsically not favorable for sufficient FMO separation, but unexpectedly reduced the singlet and triplet energy gap (ΔEST ) and thus facilitated TADF feature by pulling down the lowest singlet state energy. While the reduced distorsion instead improved the HOMO-LUMO overlap and boosted the fluorescence quantum yield from 41 % to 94 %. The blue organic light-emitting diode of TrzBuCz-CN exhibited an external quantum efficiency of 13.7 % with emission peak at 466 nm, greatly superior to 6.0 % of TrzBuCz-Me. The result provides a feasible design strategy to facilitate both RISC and radiation processes by CN decoration of the linking bridge of TADF emitters.

3.
ACS Appl Mater Interfaces ; 5(11): 4937-44, 2013 Jun 12.
Artículo en Inglés | MEDLINE | ID: mdl-23688112

RESUMEN

Four heteroleptic bis-cyclometalated iridium(III) complexes containing 2-aryl-benzothiazole ligands, in which the aryl is dibenzofuran-2-yl [Ir(O-bt)2(acac)], dibenzothiophene-2-yl [Ir(S-bt)2(acac)], dibenzothiophene-S,S-dioxide-2-yl [Ir(SO2-bt)2(acac)] and 4-(diphenylphosphoryl)phenyl [Ir(PO-bt)2(acac)], have been synthesized and characterized for use in organic light-emitting diodes (OLEDs). These complexes emit bright yellow (551 nm) to orange-red (598 nm) phosphorescence at room temperature, the peak wavelengths of which can be finely tuned depending upon the electronic properties of the aryl group in the 2-position of benzothiazole. The strong electron-withdrawing aryls such as dibenzothiophene-S,S-dioxide2-yl and 4-(diphenylphosphoryl)phenyl caused bathochromatic shift of the iridium complex phosphorescence. These iridium complexes were used as doped emitters to fabricate yellow to orange-red OLEDs and good performance was obtained. In particular, a maximum luminance efficiency of 58.4 cd A(-1) (corresponding to 30.6 lm W(-1) and 19%) with CIE coordinates of (0.45, 0.52) was achieved for Ir(O-bt)2(acac)-based yellow device. Furthermore, the yellow emitting Ir(S-bt)2(acac) was used to fabricate two-element white OLED that exhibited a high efficiency of 32.4 cd A(-1) with CIE coordinates of (0.28, 0.44).

5.
Macromol Rapid Commun ; 32(9-10): 736-43, 2011 May 18.
Artículo en Inglés | MEDLINE | ID: mdl-21448911

RESUMEN

A group of novel thieno-[3,4-b]-pyrazine-cored molecules containing polyphenyl dendrons with or without arylamino or carbazolyl surface groups (DTP, N-DTP and C-DTP) are synthesized and investigated. They are characterized by extra large Stokes shifts of over 250 nm. In addition, to provide the site-isolation effect on the planar emissive core, the bulky dendrons enable these molecules to be solution processible. The peripheral carbazolyl or arylamino units facilitate the hole transporting ability in the neat films of these molecules. These dendritic materials are used as a non-doped emitting layer to fabricate organic light-emitting diodes (OLEDs) using a spin coating technique and saturated red emission is obtained. The dendritic molecules with arylamino or carbazolyl surface groups (N-DTP and C-DTP) exhibit a brightness of 1020 cd m(-2) and a luminous efficiency of 0.6 cd A(-1) , both higher than the dendritic analog without the surface functional groups (DTP), even superior to the small molecular reference compound which fails to transmit pure red emission under identical conditions. This performance is also comparable with that from vacuum deposited thieno-[3,4-b]-pyrazine-based counterparts and that for some other solution processible red fluorescent dendrimers. This is the first example of solution processible thieno-[3,4-b]-pyrazine derivatives for OLED applications.


Asunto(s)
Polímeros/síntesis química , Pirazinas/química , Electroquímica , Fluorescencia , Polímeros/química
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