Oligofluorene with multiple spiro-connections: its and their use in blue and white OLEDs

Xia, Debin; Duan, Chunbo; Ding, Dongxue; Baumgarten, Martin; Wagner, Manfred; Schollmeyer, Dieter; Xu, Hui; Müllen, Kläus

doi:10.1039/c8nj06135a

Cited by 11 publications

(12 citation statements)

References 40 publications

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“…In 2019, 3D spiro‐fused rigid compound 15 (Scheme 5) was prepared by Xia et al. with an overall yield of 88 % [21] . Its tert ‐Butyl groups and 3D geometry enhanced its solubility in common organic solvents.…”

Section: All Carbon Spiro‐bifluorene and Indeno Spiro‐bifluorene‐fusementioning

confidence: 99%

“…Finally, apart from serving as an active component of blue OLEDs, compound 15 could be applied as a host for white OLEDs. In combination with the yellow emitter 3,4,5,6‐tetrakis(3,6‐diphenyl‐carbazol‐9‐yl)‐1,2‐dicyanobenzene (4CzPNPh), white OLEDs are capable of offering a turn‐on voltage of 3.5 V and a current efficiency (CE) of 3.6 Cd A −1 , along with CIE coordinates of (0.29, 0.33) [21] …”

Section: All Carbon Spiro‐bifluorene and Indeno Spiro‐bifluorene‐fusementioning

confidence: 99%

“…In 2019, 3D spiro-fused rigid compound 15 (Scheme 5) was prepared by Xia et al with an overall yield of 88 %. [21] Its tert-Butyl groups and 3D geometry enhanced its solubility in common organic solvents. The two diindeno-fused fluorene backbones spread over 15 Å in length and were perpendicular to each other ( Figure 3), despite the annulated rigid and strained five-membered rings preventing the backbones from being completely flat.…”

Section: All Carbon Spiro-bifluorene and Indeno Spiro-bifluorene-fusementioning

confidence: 99%

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Rigidly Fused Spiro‐Conjugated π‐Systems

Xia

Baumgarten

2020

ChemPlusChem

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Spiro‐fused π‐systems have gained considerable attention for their application as semiconductors in molecular electronics. Here, a synopsis regarding recent breakthroughs in ladderized spirobifluorenes and indeno‐spirobifluorenes, along with further spiro‐condensed heteroatomic hydrocarbons with donor‐acceptor moieties, is provided. Additionally, an extended range of rigid spirobifluorene polymers and specific doubly linked spiro‐systems with partial chiral character is discussed. The diverse applications of the aforementioned structures are thoroughly evaluated.

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Section: All Carbon Spiro‐bifluorene and Indeno Spiro‐bifluorene‐fusementioning

confidence: 99%

Section: All Carbon Spiro‐bifluorene and Indeno Spiro‐bifluorene‐fusementioning

confidence: 99%

Section: All Carbon Spiro-bifluorene and Indeno Spiro-bifluorene-fusementioning

confidence: 99%

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Rigidly Fused Spiro‐Conjugated π‐Systems

Xia

Baumgarten

2020

ChemPlusChem

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“…In 5 , four fluorene units and two ladder tetraphenylene units are linked thanks to five spirobridges (Figure 1). [ 14 ] Due to the orthogonal configuration of the six π‐conjugated systems, intermolecular aggregation in solid state is prevented. The symmetric mirror images of the absorption and emission spectra, as well as the very small Stokes shift (4 nm in p‐ xylene) coincide with the superrigid molecular structure of 5 possessing a high Φ sol (76%) in cyclohexane.…”

Section: Blue Single‐layer Oleds Using Pure Hydrocarbon Oscsmentioning

confidence: 99%

Blue Single‐Layer Organic Light‐Emitting Diodes Using Fluorescent Materials: A Molecular Design View Point

Poriel

Rault‐Berthelot

2020

Adv Funct Materials

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technology is mastered, it suffers from a real complexity, a high cost, and is time-consuming. Simplifying the multilayer structure with the so-called single-layer OLEDs (SL-OLEDs), the simplest device only made of the electrodes and the EML has hence rapidly appeared as a promising and appealing solution in this technology (Scheme 2, left).However, removing the functional organic layers of an OLED stack often leads to a dramatic decrease of the performance and reaching high efficiency blue SL-OLEDs has required intense researches and especially in term of materials design. Indeed, if one removes all the organic layers surrounding the EML, the efficient injection, transport, and recombination of charges within the device, should be insured by the EML itself and therefore the fluorophore. However, this appears to be a real obstacle to cross for blue emitting materials. Indeed, blue fluorophores usually possess a high HOMO and a low LUMO energy rendering the injection of charges in such materials very difficult. This has been one of the main issue to address in this field. Common properties required for high-performance blue emitting materials can be summarized as follows: 1) blue light emission between 380 and 500 nm with maximum wavelength around 450 nm; 2) a narrow full width at half maximum less than 60 nm; which produces low Commission Internationale de l'Eclairage (CIE) y-coordinate of less than 0.10 for TVs and cell phones; 3) thermal and morphological stability for stable device operation and a long device lifetime; 4) balance charge transport between electrons and holes flow and 5) adequate HOMO/LUMO energy levels for charge recombination and injection.Gathering all these properties in a single molecule is far from being an easy task and requires very precise designs. Indeed, as soon as one tries to adjust the HOMO/ LUMO energy levels of an organic semiconductor (OSC) with the Fermi levels of OLED electrodes, its gap is contracted and the emission wavelength is bathochromically shifted. This design strategy can hence lead to a material in which the charges can be more easily injected (the gap is contracted) but with an emission wavelength no more in the blue region. Trying to find the best compromise between adequate HOMO/LUMO energy and a blue emission has been the main challenge to address in the molecular design of efficient fluorophores for blue SL-OLEDs. This particularity has strongly restrained the development of such materials. However, for the last 30 years, research groups have developed many different molecular design strategies, which have led in some cases to high performance blue SL-OLEDs. Reaching high performance SL-OLEDs by molecular engineering of the fluorophore and Cyril Poriel is

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“…32 DSF-IF is also found as building block in fused extended -conjugated systems. [33][34][35][36] From an organic chemistry point of view, the formation of the two spiro bridges of substituted DSF-IF compounds has been the purpose of several synthetic studies, which have led to a new generation of DSF-IF positional isomers. 15,37,38 However, this scaffold is not restricted to organic electronic applications since its appealing 3D geometry has allowed to design predictably ordered materials, 39 liquid crystals, 40 electroactive polymers, 24,28 showing its interesting versatility.…”

Section: Introductionmentioning

confidence: 99%

A–π–A, D–π–D and D–π–A blue emitting fluorophores based on dispiro[fluorene-9,6′-indeno[1,2-b]fluorene-12′,9′′-fluorene]

et al. 2021

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Oligofluorene with multiple spiro-connections: its and their use in blue and white OLEDs

Abstract: This work reports the synthesis and characterization of super rigid oligofluorenes. We also demonstrate their applications in blue and white OLEDs.

Cited by 11 publications

References 40 publications

Rigidly Fused Spiro‐Conjugated π‐Systems

Rigidly Fused Spiro‐Conjugated π‐Systems

Blue Single‐Layer Organic Light‐Emitting Diodes Using Fluorescent Materials: A Molecular Design View Point

A–π–A, D–π–D and D–π–A blue emitting fluorophores based on dispiro[fluorene-9,6′-indeno[1,2-b]fluorene-12′,9′′-fluorene]

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