Asymmetric Pentacene Derivatives for Organic Light-Emitting Diodes

Jang, Bo‐Bin; Lee, Sang Ho; Kafafi, Zakya H.

doi:10.1021/cm052069h

Cited by 60 publications

(40 citation statements)

References 50 publications

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“…All materials were purified via consecutive vacuumtrain sublimation prior to use [26]. The oxidation and reduction potentials of TP-5 were measured as previously reported [27].…”

Section: Methodsmentioning

confidence: 99%

“…The highest occupied molecular orbital (HOMO) energy level of TP-5 estimated from the CV data (E HOMO = -5.02 eV) is half a volt higher than that of the Alq 3 host (E HOMO = -5.53 eV), [27,37] clearly illustrating that dioxolane-substituted pentacenes may act as hole traps in these guest-host systems. Furthermore, the CV-estimated lowest unoccupied molecular orbital (LUMO) position of TP-5 is E LUMO = -3.1 eV, which lies much lower than that of Alq 3 (E LUMO = -2.5 eV) estimated by CV.…”

Section: Full Papermentioning

confidence: 99%

“…30 %) when dispersed in thin films of tris(quinolin-8-olato) aluminum(III) (Alq 3 ). [23][24][25][26][27] OLEDs based on these molecularly doped thin films display stable external EL quantum efficiencies on the order of 1.3 to 1.6 % when operated at current densities of 100 A m -2 and higher. These values closely approach the predicted theoretical limit, which is directly proportional to the photoluminescence (PL) quantum yield of the emitting material used in a device.…”

Section: Introductionmentioning

confidence: 99%

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High-Performance Organic Light-Emitting Diodes Based on Dioxolane-Substituted Pentacene Derivatives

et al. 2006

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Organic light‐emitting diodes (OLEDs) containing red‐light‐emitting dioxolane‐substituted pentacene derivatives are fabricated and characterized. The OLEDs feature guest–host emitting layers consisting of either 6,14‐bis(triisopropylsilylethynyl)‐1,3,9,11‐tetraoxa‐dicyclopenta[b,m]pentacene (TP‐5) or 2,2,10,10‐tetraethyl‐6,14‐bis(triisopropylsilylethynyl)‐1,3,9,11‐tetraoxa‐dicyclopenta[b,m]pentacene (EtTP‐5) dispersed in tris(quinolin‐8‐olato) aluminum(III) (Alq3). High external electroluminescence (EL) quantum efficiency (ηEL = 3.3 %), not far from the theoretical limit, is observed for an OLED device based on a dilute EtTP‐5:Alq3 emitting layer (0.25 mol % EtTP‐5). The proposed EL mechanism is a combination of Förster energy transfer and direct electron–hole recombination on the guest pentacene molecules, as inferred by changes in the EL versus photoluminescence spectra and the positions of the highest occupied molecular orbital and lowest unoccupied molecular orbital gap of the guest within that of the host (estimated via cyclic voltammetry). Further evidence of charge trapping is provided by increased operational voltages at increased guest‐molecule concentration.

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“…All materials were purified via consecutive vacuumtrain sublimation prior to use [26]. The oxidation and reduction potentials of TP-5 were measured as previously reported [27].…”

Section: Methodsmentioning

confidence: 99%

Section: Full Papermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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High-Performance Organic Light-Emitting Diodes Based on Dioxolane-Substituted Pentacene Derivatives

et al. 2006

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“…The smallest acenes, benzene (n = 1) and naphthalene (n = 2), are well known aromatic compounds, while the intermediate ones, tetracene (n = 4) and pentacene (n = 5), are semiconductor materials in their solid phase. These are commonly used in organic field effect transistors [5,25], organic light emitting diodes [26,27] and organic photovoltaic cells [28], because of their high charge carrier mobility. For pentacene single crystals a value of 35 cm 2 V −1 s −1 was reported [17], which is among the highest mobility of all organic semiconductors.…”

Section: Introductionmentioning

confidence: 99%

Spin transport in highern-acene molecules

et al. 2011

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Abstract. We investigate the spin transport properties of molecules belonging to the acenes series by using density functional theory combined with the non-equilibrium Green's function approach to electronic transport. While short acenes are found to be non-magnetic, molecules comprising more than nine acene rings have a spin-polarized ground state. In their gas phase these have a singlet total spin configuration, since the two unpaired electrons occupying the doubly degenerate highest molecular orbital are antiferromagnetically coupled to each other. Such an orbital degeneracy is however lifted once the molecule is attached asymmetrically to Au electrodes via thiol linkers, leading to a fractional magnetic moment. In this situation the system Au/n-acene/Au can act as an efficient spin-filter with interesting applications in the emerging field of organic spintronics.

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“…The larger tetracene (4) and pentacene (5) are promising organic semiconductors and have been applied as OFETs (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) thanks to a low vibrational reorganization energy and therefore a high hole mobility (18). Many of the derivatives of 4 and 5 are good candidates for OLEDs (19)(20)(21)(22). Recently, with a growing interest in solar energy and solar cells, 4 and 5 have also been made into OPV devices (23)(24)(25)(26)(27).…”

mentioning

confidence: 99%

Nature of ground and electronic excited states of higher acenes

Yang

Davidson

Yang

2016

Proc. Natl. Acad. Sci. U.S.A.

174

208

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Higher acenes have drawn much attention as promising organic semiconductors with versatile electronic properties. However, the nature of their ground state and electronic excited states is still not fully clear. Their unusual chemical reactivity and instability are the main obstacles for experimental studies, and the potentially prominent diradical character, which might require a multireference description in such large systems, hinders theoretical investigations. Here, we provide a detailed answer with the particleparticle random-phase approximation calculation. The 1 A g ground states of acenes up to decacene are on the closed-shell side of the diradical continuum, whereas the ground state of undecacene and dodecacene tilts more to the open-shell side with a growing polyradical character. The ground state of all acenes has covalent nature with respect to both short and long axes. The lowest triplet state 3 B 2u is always above the singlet ground state even though the energy gap could be vanishingly small in the polyacene limit. The bright singlet excited state 1 B 2u is a zwitterionic state to the short axis. The excited 1 A g state gradually switches from a doubleexcitation state to another zwitterionic state to the short axis, but always keeps its covalent nature to the long axis. An energy crossing between the 1 B 2u and excited 1 A g states happens between hexacene and heptacene. Further energetic consideration suggests that higher acenes are likely to undergo singlet fission with a low photovoltaic efficiency; however, the efficiency might be improved if a singlet fission into multiple triplets could be achieved.higher acenes | diradical | double excitation | particle-particle random-phase approximation | charge-transfer excitation

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Asymmetric Pentacene Derivatives for Organic Light-Emitting Diodes

Cited by 60 publications

References 50 publications

High-Performance Organic Light-Emitting Diodes Based on Dioxolane-Substituted Pentacene Derivatives

High-Performance Organic Light-Emitting Diodes Based on Dioxolane-Substituted Pentacene Derivatives

Spin transport in highern-acene molecules

Nature of ground and electronic excited states of higher acenes

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