Triptycene derivatives as high-T<sub>g</sub>host materials for various electrophosphorescent devices

Chou, Ho‐Hsiu; Shih, Hung-Hsin; Cheng, Chien‐Hong

doi:10.1039/b918188a

Cited by 57 publications

(37 citation statements)

References 28 publications

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“…Although the aggregation issue in thin films compromises the device performance, there are well established strategies to modify the molecular structure of both pentacene and anthracene through, for example, the incorporation of sterically demanding groups . Indeed, several groups have recently focused on modifying different families of acenes with iptycene units to avoid the photoluminescence self‐quenching produced in thin‐films, showing a significant enhanced performance in OLEDs . As such, this might be considered as a future strategy to enhance the overall efficiency even more.…”

Section: Resultsmentioning

confidence: 99%

“…Finally, the sharp red emission at around 650 nm and the moderate photoluminescence quantum yields (PLQYs) when dispersed in a thin film with the electron‐transporting host tris(quinoline‐8‐olato)‐aluminum(III) (Alq 3 ) prompted Kafafi and Anthony groups to fabricate the first OLEDs based on trialkylsilylethynyl‐substitute pentacenes . As the most remarkable result, the authors demonstrated that through a proper design of the molecular structure a near quantitative internal quantum efficiency based on the PLQYs of the active layer is realized . Encouraged by this excellent result, we decided to probe the performance of the archetypal TIPS‐pentacene as an emitter in small molecule light‐emitting electrochemical cells (SM‐LECs).…”

Section: Introductionmentioning

confidence: 99%

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Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Weber

Adam

Tykwinski

et al. 2015

Adv Funct Materials

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5066 wileyonlinelibrary.com the most intriguing archetypal compounds. For instance, remarkable charge mobilities of up to 4.6 cm 2 V −1 s −1 for its solution-sheared thin fi lms applied in OFETs have been achieved. [ 8 ] Recently, the same authors have demonstrated that the control of the structural arrangement in fi lms boosts the fi eld-effect mobility to remarkable values of 11 cm 2 V −1 s −1 . [ 9 ] In addition, this molecule has recently emerged as a paradigm to study singlet fi ssion process in both solution and thin fi lms, owing to its triplet quantum yield formation exceeding values of 100%. [ 5,6,[10][11][12][13] Finally, the sharp red emission at around 650 nm and the moderate photoluminescence quantum yields (PLQYs) when dispersed in a thin fi lm with the electrontransporting host tris(quinoline-8-olato)-aluminum(III) (Alq 3 ) prompted Kafafi and Anthony groups to fabricate the fi rst OLEDs based on trialkylsilylethynyl-substitute pentacenes. [ 14,15 ] As the most remarkable result, the authors demonstrated that through a proper design of the molecular structure a near quantitative internal quantum effi ciency based on the PLQYs of the active layer is realized. [ 16 ] Encouraged by this excellent result, we decided to probe the performance of the archetypal TIPS-pentacene as an emitter in small molecule light-emitting electrochemical cells (SM-LECs).LECs have emerged as an interesting alternative to OLEDs due to the single-layer device architecture based on air-stable electrodes, the high power effi ciencies at very low operation voltages, and the low-cost manufacturing process on any 3D-shaped substrate. [17][18][19][20][21][22] These assets are possible due to the unique mechanism as the active layer comprises a blend of mobile ions and mostly one electroactive compound. [23][24][25][26][27] Up to date, the most representative materials for LECs have been mixtures of a light-emitting polymer, an ion conducting polymer, and an inorganic salt, as well as mixtures of ionic transition-metal complexes (iTMCs) and ionic liquids. [19][20][21] However, Edman and co-workers have recently demonstrated that the LEC concept can be easily expanded to small molecule (SM) materials. [ 28 ] This result represents a landmark toward future breakthroughs in the fi eld, especially if we take into account the very recent achievements in SM-based OLEDs that are considered as the new momentum heading into the third generation of this technology, [29][30][31][32][33] as well as SMs are considered as the third generation of materials for LECs, which is now in its early infancy. [ 28,34 ] Controlling the Chromaticity of Small-Molecule LightEmitting Electrochemical Cells Based on TIPS-Pentacene

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Weber

Adam

Tykwinski

et al. 2015

Adv Funct Materials

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“…[26] The rigid triptycene core also has applications in coordination chemistry, catalysis for stabilizing highly reactive intermediates [27] and sterically bent complexes, [28] and electrophosphorescence. [29] Furthermore, electron and energy transfer in rigid triptycene-bipyridine metal complexes [30] and in porphyrin-based dyads and triads for charge separation [31] has also been investigated. Studies on triptycene-bridged donors/acceptors have demonstrated that electronic interactions occur through the s-bridged system, [32] and that no homoconjugation effect is present in the p-conjugated oligomers.…”

Section: Introductionmentioning

confidence: 99%

Ultrafast Energy Transfer in Triptycene‐Grafted Bodipy Scaffoldings

Bura¹,

Nastasi²,

Puntoriero³

et al. 2013

Chemistry A European J

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A series of new compounds in which various Bodipy dyes are grafted logically on triptycene rigid structures are synthesized and characterized, and their absorption spectra and photophysical properties are studied, also by pump-probe transient absorption spectroscopy. The studied compounds are: the mono-Bodipy species TA, TB, and TC (where A, B, and C identify different Bodipy subunits absorbing and emitting at different wavelengths), the multichromophore species TA3 , which bears three identical A subunits, and the three multichromophoric species TAB, TBC, and TABC, all of them containing at least two different types of Bodipy subunits. The triptycene moiety plays the role of a rigid scaffold, keeping the various dyes at predetermined distances and allowing for a three-dimensional structural arrangement of the multichromophoric species. The absorption spectra of the multichromophoric Bodipy species are essentially additive, indicating that negligible inter-chromophoric interaction takes place at the ground state. Luminescence properties and transient absorption spectroscopy indicate that a very fast (on the picosecond time scale) and efficient photoinduced energy transfer occurs in all the multi-Bodipy species, with the lower-energy Bodipy subunits of each multi-Bodipy compounds playing the role of an electronic energy collector. In TAB, an energy transfer from the A-type Bodipy subunit to the B-type one takes place with a rate constant of 1.6×10(10) s(-1), whereas in TBC an energy transfer from the B-type Bodipy subunit to the C-type subunit is bi-exponential, exhibiting rate constants of 1.7×10(11) and 1.9×10(10) s(-1); the possible presence of different conformers with different donor-acceptor distances in this bichromophoric species is proposed to cause the bi-exponential energy-transfer process. Interpretation of the intricate energy-transfer pathways occurring in TABC is made with the help of the processes identified in the bichromophoric compounds. In all cases, the measured energy-transfer rate constants agree with a Förster mechanism for the energy-transfer processes.

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“…Compared with G1MP, an enhancement of about 115–120 °C is obtained in the higher‐generation dendrimers, which arises from the high molecular weight and bulky carbazole dendrons. As can be clearly seen in Figure b, distinct endothermic peaks related to the glass transition appear at 297 °C and 368 °C for G2MP and G3MP, respectively, which are among the highest ever reported for host materials . This result implies that the films of G2MP and G3MP would have excellent morphological stability, a favorable feature for the realization of long‐term PhOLEDs.…”

Section: Resultsmentioning

confidence: 73%

Solution‐Processible 2,2′‐Dimethyl‐biphenyl Cored Carbazole Dendrimers as Universal Hosts for Efficient Blue, Green, and Red Phosphorescent OLEDs

Wang

et al. 2014

Adv Funct Materials

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A series of solution‐processible 2,2′‐dimethyl‐biphenyl cored dendrimers, namely G1MP, G2MP, and G3MP, is designed and synthesized by tuning the generation of periphery carbazole dendron. The resulting dendrimers all show excellent solubility in common organic solvents, and their high‐quality thin films can be formed via spin‐coating with a root‐mean‐square roughness in the range of 0.38–0.54 nm. G3MP, which contains the third‐generation carbazole dendron, has the greatest potential among those made here as an ideal universal host for multicolored triplet emitters. G3MP exhibits good thermal stability, with a glass transition temperature of 368 °C, a triplet energy as high as 2.85 eV enough to prevent the loss of triplet excitons, and suitable HOMO/LUMO levels of –5.30/–2.11 eV to facilitate both hole and electron injection and transport. When using G3MP as the host, highly efficient deep‐blue, blue, green, and red phosphorescent organic light‐emitting diodes (PhOLEDs) are successfully demonstrated, revealing a maximum luminous efficiency up to 18.2, 28.2, 54.0, and 12.7 cd A–1 with the corresponding Commission Internationale de L'Eclairage (CIE) coordinates of (0.15, 0.23), (0.15, 0.35), (0.38, 0.59), and (0.64, 0.34), respectively. The state‐of‐art performance indicates that dendritic hosts have a favorable prospect of applications in solution‐processed white PhOLEDs and full‐color displays.

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Triptycene derivatives as high-T_ghost materials for various electrophosphorescent devices

Cited by 57 publications

References 28 publications

Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Ultrafast Energy Transfer in Triptycene‐Grafted Bodipy Scaffoldings

Solution‐Processible 2,2′‐Dimethyl‐biphenyl Cored Carbazole Dendrimers as Universal Hosts for Efficient Blue, Green, and Red Phosphorescent OLEDs

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Triptycene derivatives as high-Tghost materials for various electrophosphorescent devices

Cited by 57 publications

References 28 publications

Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Ultrafast Energy Transfer in Triptycene‐Grafted Bodipy Scaffoldings

Solution‐Processible 2,2′‐Dimethyl‐biphenyl Cored Carbazole Dendrimers as Universal Hosts for Efficient Blue, Green, and Red Phosphorescent OLEDs

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Triptycene derivatives as high-T_ghost materials for various electrophosphorescent devices