9,9′-Spirobifluorene and 4-phenyl-9,9′-spirobifluorene: pure hydrocarbon small molecules as hosts for efficient green and blue PhOLEDs

Thiery, Sébastien; Tondelier, Denis; Declairieux, Céline; Seo, Gijun; Geffroy, Bernard; Jeannin, Olivier; Rault‐Berthelot, Joëlle; Métivier, Rémi; Poriel, Cyril

doi:10.1039/c4tc00171k

Cited by 76 publications

(171 citation statements)

References 51 publications

(56 reference statements)

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“…The unsubstituted SBF exhibits two characteristic bands at 297 and 308 nm corresponding to π−π * transitions (See TD-DFT calculations in SI). [22] The four phenylsubstituted SBF isomers all display these two thin bands ( Figure 2) at a similar wavelength. In addition to these bands, 2 displays an extra and large band centred at 319 nm.…”

Section: Scheme 1 Synthetic Routes To 1 Andmentioning

confidence: 94%

“…The synthesis of 2 and 4 has been previously described in literature, [21,22] that of 1 and 3 is described in Scheme 1. The synthesis of 1 (Scheme 1, Top) starts with the synthesis of the key fluorenone c1, substituted in position 1 with an iodine atom.…”

Section: Resultsmentioning

confidence: 99%

“…[21] This structural feature, assigned to the steric interaction between the hydrogen atoms in ortho position of the pendant phenyl ring and that of the fluorenyl core is at the origin of the partial π-conjugation breaking of 4-substituted SBFs. [22] In 1, this dihedral angle appears to be impressively larger reaching 75.4° ( Figure 1, top left) for one molecule and 66.7° for the other (2 molecules are indeed present in the asymmetric unit, see SI). This structural particularity is the consequence of the substitution in ortho position of the spiro carbon, which leads to a sterically hindered environment due to the presence of the cofacial fluorene.…”

Section: Scheme 1 Synthetic Routes To 1 Andmentioning

confidence: 99%

“…This result, although in full accordance with that exposed above in absorption appears again very surprising as the meta linkage of 3 should strongly restrict the π-conjugation compared to the para linkage of 2. 22,25 This is again the consequence of the spiro bridge in para position of the phenyl ring. Both fluorophores 2 and 3 also display a high quantum yield (87 and 74 % resp.…”

Section: Scheme 1 Synthetic Routes To 1 Andmentioning

confidence: 99%

“…This work reports hence the first structure-properties relationship study of the four SBF positional isomers (substituted with a phenyl ring) namely 2-phenyl-SBF 2 possessing a para 3 linkage, [21] 1-phenyl-SBF 1 and 3-phenyl-SBF 3 both possessing a meta linkage and 4-phenyl-SBF 4 possessing an ortho linkage, [22] Chart 1. Thanks to a comparison with the structurally fluorene analogues, this work provides a foundation on the impact of SBF regioisomerism on the electronic properties.…”

Section: Chart 1 Sbf and The Four Positional Isomers Of Phenyl Substmentioning

confidence: 99%

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Spirobifluorene Regioisomerism: A Structure–Property Relationship Study

Sicard

Quinton

Peltier

et al. 2017

Chemistry A European J

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Abstract:The present works report the first structure-properties relationship study of a key class of organics semiconductors, ie the four spirobifluorene positional isomers possessing a para, meta or ortho linkage. The remarkable and surprising impact of the ring bridging and of the linkages on the electronic properties of the regioisomers has been particularly highlighted and rationalized. The impact of the ring bridging on the photophysical properties has been stressed with notably the different influence of the linkages and the bridge on the singlet and triplet excited states. The first member of a new family of spirobifluorenes substituted in position 1, which presents better performances in blue Phosphorescent OLEDs than those of its regioisomers is reported. These features highlight not only the great potential of 1-substituted spirobifluorenes but also the remarkable impact of regioisomerism on electronic properties.

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Section: Scheme 1 Synthetic Routes To 1 Andmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Scheme 1 Synthetic Routes To 1 Andmentioning

confidence: 99%

Section: Scheme 1 Synthetic Routes To 1 Andmentioning

confidence: 99%

Section: Chart 1 Sbf and The Four Positional Isomers Of Phenyl Substmentioning

confidence: 99%

See 3 more Smart Citations

Spirobifluorene Regioisomerism: A Structure–Property Relationship Study

Sicard

Quinton

Peltier

et al. 2017

Chemistry A European J

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154

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Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting Panel

Liu

Dong

Jiang

et al. 2014

Adv Funct Materials

145

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1wileyonlinelibrary.com power effi ciency (PE) >50 lm W −1 and low effi ciency roll-off at 5000 cd m −2 are still rare. [ 5 ] Considering the pursuit of various blue emitters is still ongoing, [ 6 ] it is also necessary to develop new host materials to test different kinds of emitting phosphors. Furthermore, another main application for blue hosts is for the high-effi ciency white light emission; their performances on large-size lighting panels are fascinating but still a blank in recent literature reports. [ 6 ] Therefore, constant efforts should be devoted to developing good host materials that can achieve high efficiency and fl at effi ciency roll-off simultaneously in blue/white PHOLEDs.The compounds with spiro-core are good candidates in constructing bipolar materials for the inherent orthogonal structure of two molecular halves. In addition, this approach can also effi ciently suppress intermolecular interaction by their adamant backbone, resulting in better solubility and cause entanglement in the amorphous state, then hinder recrystallization. [ 7 ] The development of spiro host material, however, is relatively slower as compared with other series of host materials. In 2005, the fi rst example of spiro host materials named SSS based on 9,9′-spirobifl uorene core is reported, which obtained EQE of ≈10% for red phosphorescence. [ 8 ] In 2008, the fi rst spiro bipolar molecule D2ACN integrated with electron-rich diphenylamine and electron-defi cient nitrile is prepared, but the EQE is just slightly improved to 10.8% with PE of 13 lm W −1 as red host material. [ 9 ] To date, there are just several attempts on blue hosts based on spiro-structure and the device performances are moderate. [ 10 ] Recently, we reported a blue host material SSTF based on new STF core, which could achieved a PE of 41.5 lm W −1 and an EQE of 18.7%. [ 11 ] In the STF molecular structure, a triphenylamine moiety is placed in vertical confi guration to fl uorene. This confi guration endows good hole-transporting ability to STF and makes it unnecessary to introduce any other arylamine groups on spiro backbone that always reduces the triplet energy (such as D2ACN). On the other hand, the fl uorene moiety can be further modifi ed by appending electron-deficient groups to enhance bipolar property. Herein, we design and prepare a new spiro host material POSTF by appending phosphine oxide group on the fl uorene moiety. It demonstrates very high EQE and extremely low effi ciency roll-offs for sky-blue (small size) and white (large size) phosphorescent devices. Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting PanelLei Ding , Shou-Cheng Dong , Zuo-Quan Jiang , * Hua Chen , and Liang-Sheng Liao * High-effi ciency blue phosphorescence devices with external quantum effi ciencies above 25% are developed using a new bipolar host material, diphenyl(10-phenyl-10 H -spiro[acridine-9,9′-fl uoren]-2′-yl)phosphine oxide (POSTF), which is constructed in orthogonal molecular structure with a ...

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Long‐Lived and Highly Efficient TADF‐PhOLED with “(A)_n–D–(A)_n” Structured Terpyridine Electron‐Transporting Material

Bian

Zhang

Wang³

et al. 2018

Adv Funct Materials

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The electron-transporting material (ETM) is one of the key factors to determine the efficiency and stability of organic light-emitting diodes (OLEDs). A novel ETM with a "(Acceptor) n -Donor-(Acceptor) n " ("(A) n -D-(A) n ") structure, 2,7-di([2,2′:6′,2″-terpyridin]-4′-yl)-9,9′-spirobifluorene (27-TPSF), is synthesized by combining electron-withdrawing terpyridine (TPY) moieties and rigid twisted spirobifluorene, in which the TPY moieties facilitate electron transport and injection while the spirobifluorene moiety ensures high triplet energy (T 1 = 2.5 eV) as well as enhances glass transition temperature (T g = 195 °C) for better stability. By using tris[2-(p-tolyl)pyridine]iridium(III) (Ir(mppy) 3 ) as the emitter, the 27-TPSF-based device exhibits a maximum external quantum efficiency (η ext, max ) of 24.5%, and a half-life (T 50 ) of 121, 6804, and 382 636 h at an initial luminance of 10 000, 1000, and 100 cd m −2 , respectively, which are much better than the commercialized ETM of 9,10-bis(6-phenylpyridin-3-yl)anthracene (DPPyA). Furthermore, a higher efficiency, a η ext, max of 28.2% and a maximum power efficiency (η PE , max ) of 129.3 lm W −1 , can be achieved by adopting bis(2-phenylpyridine)iridium(III) (2,2,6,6-tetramethylheptane-3,5-diketonate) (Ir(ppy) 2 tmd) as the emitter and 27-TPSF as the ETM. These results indicate that the derivative of TPY to form "(A) n -D-(A) n " structure is a promising way to design an ETM with good comprehensive properties for OLEDs.

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9,9′-Spirobifluorene and 4-phenyl-9,9′-spirobifluorene: pure hydrocarbon small molecules as hosts for efficient green and blue PhOLEDs

Abstract: This work reports the use of 9,9′-spirobifluorene and 4-phenyl-9,9′-spirobifluorene, pure hydrocarbon small molecules, as hosts for efficient green and blue phosphorescent OLEDs.

Cited by 76 publications

References 51 publications

Spirobifluorene Regioisomerism: A Structure–Property Relationship Study

Spirobifluorene Regioisomerism: A Structure–Property Relationship Study

Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting Panel

Long‐Lived and Highly Efficient TADF‐PhOLED with “(A)_n–D–(A)_n” Structured Terpyridine Electron‐Transporting Material

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9,9′-Spirobifluorene and 4-phenyl-9,9′-spirobifluorene: pure hydrocarbon small molecules as hosts for efficient green and blue PhOLEDs

Abstract: This work reports the use of 9,9′-spirobifluorene and 4-phenyl-9,9′-spirobifluorene, pure hydrocarbon small molecules, as hosts for efficient green and blue phosphorescent OLEDs.

Cited by 76 publications

References 51 publications

Spirobifluorene Regioisomerism: A Structure–Property Relationship Study

Spirobifluorene Regioisomerism: A Structure–Property Relationship Study

Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting Panel

Long‐Lived and Highly Efficient TADF‐PhOLED with “(A)n–D–(A)n” Structured Terpyridine Electron‐Transporting Material

Contact Info

Product

Resources

About

Long‐Lived and Highly Efficient TADF‐PhOLED with “(A)_n–D–(A)_n” Structured Terpyridine Electron‐Transporting Material