An S-shaped double helicene showing both multi-resonance thermally activated delayed fluorescence and circularly polarized luminescence

Santos, John Marques dos; Sun, Dianming; Moreno-Naranjo, Juan Manuel; Hall, David; Zinna, Francesco; J., Ryan Sean T.; Shi, Wei; Matulaitis, Tomas; Cordes, David B.; Slawin, Alexandra M. Z.; Beljonne, David; L., Warriner Stuart; Olivier, Yoann; J., Fuchter Matthew; Zysman‐Colman, Eli

doi:10.1039/d2tc00198e

Cited by 27 publications

(28 citation statements)

References 112 publications

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“…Furthermore, the high molecular rigidity contrib- In 2022, Zysman-Colman et al reported the ketone derivatives named Hel-DiDiKTa with an S-shaped helicene structure. [30] The extended π conjugations also obey the donor and acceptor distribution rule for MR-TADF, which lead to the slight redshifted with sky-blue narrow-band emission (λ PL = 473/478 nm, FWHM = 44/52 nm in toluene/doped film, respectively) compared with the core QAO (λ PL = 466 nm, FWHM = 32 nm in toluene). Although Hel-DiDiKTa exhibited high molecular rigidity, it does exhibit low PLQY (< 10 %) in doped 1,3-bis(Ncarbazolyl)benzene (mCP) films with various doping ratios.…”

Section: Fusing Modification By Mr Groupmentioning

confidence: 94%

“…In 2022, Zysman‐Colman et al. reported the ketone derivatives named Hel‐DiDiKTa with an S‐shaped helicene structure [30] . The extended π conjugations also obey the donor and acceptor distribution rule for MR‐TADF, which lead to the slight red‐shifted with sky‐blue narrow‐band emission ( λ PL =473/478 nm, FWHM=44/52 nm in toluene/doped film, respectively) compared with the core QAO ( λ PL =466 nm, FWHM=32 nm in toluene).…”

Section: Mr‐type Derivativesmentioning

confidence: 99%

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Carbonyl‐Containing Thermally Activated Delayed Fluorescence Emitters for Narrow‐Band Electroluminescence

Liu

Meng

et al. 2022

Chemistry A European J

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Carbonyl‐containing derivatives show enduring vitality in the field of thermally activated delayed fluorescence (TADF) materials; they can realize high device efficiency by using both singlet and triplet excitons for electroluminescence. Recently, a system based on fused ketone/amine exhibited huge potential for constructing multi‐resonance TADF (MR‐TADF) emitters, which exhibit higher narrow‐band emission than conventional TADF emitters with twisted donor‐acceptor (D‐A) structure. Herein, we summarize current research progress in both traditional and MR‐type ketone derivatives with TADF characteristics for introducing the molecular design strategy of maintaining high device efficiency while keeping narrow‐band emission profile. We hope this review can inspire the emergence of more high‐performance narrow‐band materials.

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Section: Fusing Modification By Mr Groupmentioning

confidence: 94%

Section: Mr‐type Derivativesmentioning

confidence: 99%

Carbonyl‐Containing Thermally Activated Delayed Fluorescence Emitters for Narrow‐Band Electroluminescence

Liu

Meng

et al. 2022

Chemistry A European J

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“…Zysman‐Colman and co‐workers reported an S‐shaped double helicene, Hel‐DiDiKTa , with a CPL activity based on the helical chirality. [ 120 ] Hel‐DiDiKTa exhibited a blue‐emission peak at 473 nm with moderate FWHM PL of 44 nm in toluene. TADF behavior was observed owing to its small Δ E ST of 0.15 eV; however, the Φ PL values were extremely small both in toluene solution (Φ PL = 1.34%) and as a doped film (Φ PL = 4.1%, 1 wt% doped in mCP).…”

Section: Carbonyl/nitrogen (Co/n)‐based Mr‐tadf Materialsmentioning

confidence: 99%

Narrowband Emissive Thermally Activated Delayed Fluorescence Materials

Kim

Yasuda

2022

Advanced Optical Materials

165

113

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Organic thermally activated delayed fluorescence (TADF) materials have attracted significant research interest in the field of organic electronics because of their inherent advantage of 100% exciton utilization capability in organic light‐emitting diodes (OLEDs) without the use of noble metals. However, despite their high internal electroluminescence quantum efficiencies approaching unity, broad emission spectra with sizable full width at half maxima (FWHM; 60–100 nm) present a critical issue that must be solved for their application in ultrahigh‐definition OLED displays. Recently, a new paradigm of TADF materials featuring the multiple resonance (MR) effect based on heteroatom‐doped polycyclic aromatic frameworks, referred to as MR‐TADF materials, has emerged and garnered considerable research interest owing to their remarkable features of efficient narrowband emissions with extremely small FWHMs (≤30 nm). Currently, MR‐TADF materials occupy a prominent position in the cutting‐edge research on organic light‐emitting materials from both chemical and physical perspectives. This review article focuses on recent progress in narrowband emissive MR‐TADF systems from the perspective of molecular design, photophysical properties, and electroluminescence performance in OLEDs. The current status and future prospects of this advanced material technology are discussed comprehensively.

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“…Nevertheless, the multiple-resonance (MR) induced TADF (MR-TADF) effect with the B/N doped polycyclic fused aromatic structure provides the possibility of constructing helicene-Page 2 of 16 CCS Chemistry 3 based purely organic TADF emitters. [17][18][19][20][21][22][23][24][25] On the one hand, the complementary resonance effects of the electron-deficient B and electron-rich N/O atoms can effectively separate the frontier molecular orbitals (FMOs), which induces the short-range charge transfer to achieve a small ΔE ST for efficient TADF. [26][27][28] On the other hand, from the perspective of chemical structure, the inherent fused aromatic structures of MR-TADF effect represent a perfect platform for constructing heterohelicenes, which excludes the use of D/A units.…”

Section: Introductionmentioning

confidence: 99%

Simple Double Hetero[5]helicenes Realize Highly Efficient and Narrowband Circularly Polarized Organic Light-Emitting Diodes

Yang

Miao

et al. 2022

CCS Chem

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Helicene-based emitters with unique inherent circularly polarized luminescence (CPL) are promising yet remain a formidable challenge for highly efficient circularly polarized organic light emitting diodes (CP-OLEDs), ascribed to their tough synthesis, low emission efficiency, and easy racemization in thermal deposition process. Herein, a pair of helicene-based enantiomers, namely (P)-helicene-BN and (M)-helicene-BN, were developed, which merge helical chirality and the B/N/S inserted polycyclic aromatic framework to concurrently feature CPL and narrow thermally activated delayed fluorescence (TADF) characteristics. Benefiting from the excellent thermal/photophysical/chiroptical properties, the narrowband green CP-OLEDs based on the enantiomers achieved maximum external quantum efficiencies (EQE max ) of up to 31.5%, and dissymmetry factor (|g EL |) of 2.2 × 10 -3 . This work reveals the great potential of helicene-based emitters in CP-OLEDs.

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An S-shaped double helicene showing both multi-resonance thermally activated delayed fluorescence and circularly polarized luminescence

Abstract: We present the first example of a multi-resonant thermally activated delayed fluorescent (MR-TADF) extended helicene, Hel-DiDiKTa. This S-shaped double helicene exhibits sky-blue emission, a singlet-triplet energy gap, EST, of 0.15...

Cited by 27 publications

References 112 publications

Carbonyl‐Containing Thermally Activated Delayed Fluorescence Emitters for Narrow‐Band Electroluminescence

Carbonyl‐Containing Thermally Activated Delayed Fluorescence Emitters for Narrow‐Band Electroluminescence

Narrowband Emissive Thermally Activated Delayed Fluorescence Materials

Simple Double Hetero[5]helicenes Realize Highly Efficient and Narrowband Circularly Polarized Organic Light-Emitting Diodes

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