Fluorinated 9,9′-spirobifluorene derivatives as host materials for highly efficient blue organic light-emitting devices

Li, Zhanfeng; Jiao, Bo; Wu, Zhaoxin; Liu, Peng; Ma, Lin; Lei, Xiaoli; Wang, Dongdong; Zhou, Guijiang; Hu, Huai‐Ming; Hou, Xun

doi:10.1039/c3tc00466j

Cited by 53 publications

(20 citation statements)

References 43 publications

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“…23 This leads to a preoccupation 55 that ternary D-A systems with effective intramolecular electronic coupling can hardly realize high triplet energy approaching to 3.0 eV. [24][25][26][27][28][29][30][31][32][33][34] Nevertheless, owing to their superior electrical properties, efficient phosphorescent D-A hosts are emerged in recent years, 32,[35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] even though their intramolecualr electronic coupling is 60 commonly suppressed by meta-, insulating or twisted linkages; while, only few D-A hosts are reported for blue TADF devices. 50 Nevertheless, there are very few reports about high-energy-gap ternary D-A type hosts without any spacers or linkers involved.…”

Section: Introductionmentioning

confidence: 99%

Ternary donor–acceptor phosphine oxide hosts with peculiar high energy gap for efficient blue electroluminescence

et al. 2015

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Ternary donor (D)-acceptor (A)-acceptor (A) molecules are commonly considered as low triplet (T 1 ) energy systems for specific applications. In this work, this preoccupation was redressed by a triangleshaped D-A-A molecule PCImbPO with peculiarly high triplet energy of 3.0 eV. Profiting from the enhanced D-A electronic coupling, electron injecting and transporting ability of PCImbPO was 10 dramatically improved with negligible influences on its highest occupied molecular orbital (HOMO) characteristic. Its particular T 1 configuration adjustment further gives rise to the separated frontier MO and T 1 locations, beneficial to suppress quenching effects. By utilizing PCImbPO as host in blue phosphorescent organic light-emitting diodes (PHOLEDs) and thermally activated delayed fluorescence devices, the impressively high external quantum efficiency beyond 22 and 12% were achieved, 15 respectively. This work established a new understanding of high-energy-gap complicated D-A systems. 65 III), ternary D-A system is almost ideal as host materials with the independent highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) and T 1 locations, which is conducive to suppressing polarization-induced exciton decomposition (PIED) 51 and triplet-polaron quenching (TPQ) 70 effects. 52-53 Recently, we reported a D-A-D host with a structure of two carbazole donors linked by a phenylphosphine oxide acceptor, which endowed its FIrpic-based blue PHOLEDs with favorable performance owing to its unique dynamically adaptive electrical characteristic. 54 Nevertheless, a more in-depth 75 This journal is © The Royal Society of Chemistry [year]90 CDCl 3 , 400 MHz): δ = 8.19-8.22 (d, J = 7.6 Hz, 2H), 7.77-7.79 (d, J = 8.8 Hz, 2H), 7.41-7.51 (m, 6H), 7.35-7.38 ppm (t, J = 6.8 Hz, 2H); LDI-TOF: m/z (%): 321 (100) [M + ]; elemental analysis (%) for C 18 H

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Section: Introductionmentioning

confidence: 99%

Ternary donor–acceptor phosphine oxide hosts with peculiar high energy gap for efficient blue electroluminescence

et al. 2015

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“…In particular, the device based on the Spiro‐(3)‐F host (Figure ) showed low turn‐on voltage of 3.4 V, and very high luminance of over 10000 cd m –2 , high current efficiency of 6.66 cd A –1 and external quantum efficiency of 4.92 % …”

Section: Organic Fluorinated Materials For Oledsmentioning

confidence: 99%

Organic and Organometallic Fluorinated Materials for Electronics and Optoelectronics: A Survey on Recent Research

et al. 2018

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Conjugated organic polymers, small molecules, and transition metal organometallic complexes are used as active semiconducting materials in electronic and optoelectronic devices including organic solar cells (OSCs), organic field effect transistors (OFETS), organic light emitting diodes (OLEDs). While some of these technologies are mature and already available on the market, research is still very active in academic and industrial laboratories to gain better performances. Major drawbacks which still limit large industrial production of some of these devices are not only the non‐optimized performances, but also stability issues and cost. In fact, wide applicability of organic electronic technology largely relies on the development of efficient, durable and cost‐effective materials. Properties of molecular and polymeric semiconductors can be properly engineered and finely tuned by the design of the conjugated molecular structure and the selective introduction of various functional groups as substituents. Selective functionalization of the conjugated backbone with fluorine atoms and fluorinated substituents has been largely demonstrated to be an effective structural modification not only for tuning optoelectronic properties, but also to affect solid state organization and to improve stability. This review covers the most important classes of materials (conjugated polymers, small molecules, and organometallic complexes) reporting for each of these classes the applications in OSCs, OFETs, and OLEDs and highlighting the role of fluorine functionalization on the properties. The literature shows intriguing results that can be achieved by fluorine functionalization, and it also points out that this research field is still promising for future progress.

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“…The 9,9'-spirobifluorene moiety has been widely used as am olecular scaffold for designing unprecedented optoelectronic materials [1] in the field of organic light-emitting diodes (OLEDs) [2][3][4][5] and photovoltaic cells [6,7] because of its outstanding opticalp roperties and high thermal stability.I np articular,v arious ortho-o rpara-linked spirobifluorenes have attracted much research interest in the field as outstanding molecular platforms. [1,[8][9][10] The synergistic combination of prominento rganic/ organometallicl uminophores in conjunction with closo-ortho-carborane( 1,2-C 2 B 10 H 12 ), which is aw ell-known boron-cluster component of three-dimensional (3D) icosahedral analogues, resultsi nu nique photophysical properties due to the nature of the o-carborane moiety,s uch as its electron-withdrawing properties through C-substitution and high polarizabilityo ft he saromaticity.…”

Section: Introductionmentioning

confidence: 99%

Spirobifluorene‐Based o‐Carboranyl Compounds: Insights into the Rotational Effect of Carborane Cages on Photoluminescence

Kim

Lee

et al. 2019

Chemistry A European J

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9,9′‐Spirobifluorene‐based closo‐o‐carboranyl (SFC1 and SFC2) compounds and their nido‐derivatives (nido‐SFC1 and nido‐SFC2) were prepared and characterized. The two closo‐compounds displayed major absorption bands assignable to π–π* transitions involving the spirobifluorene group, as well as weak intramolecular charge‐transfer (ICT) transitions between the o‐carboranes and their spirobifluorene moieties. The nido‐compounds exhibited slightly blueshifted absorption bands resulting from the absence of the ICT transitions corresponding to the o‐carborane moieties due to the anionic character of the nido‐o‐carboranes. While SFC1 exhibited only high‐energy emissions in THF at 298 K (only from locally excited (LE) states assignable to π–π* transitions on the spirobifluorene group), remarkable emissions in the low‐energy region were observed in the rigid state such as in THF at 77 K and in the film state. SFC2 displayed intense emissions in the low‐energy region in all states. The fact that neither of the nido‐derivatives of SFC1 and SFC2 exhibited low‐energy emissions and the TD‐DFT calculation results of each closo‐compound clearly verified that the low‐energy emission was based on ICT‐based radiative decay. The conformational barriers from each relative energy calculation upon changing the dihedral angles around the o‐carborane cages for both compounds confirmed that the rotation of the o‐carborane cages and terminal phenyl rings for SFC1 is freer than that for SFC2.

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Fluorinated 9,9′-spirobifluorene derivatives as host materials for highly efficient blue organic light-emitting devices

Cited by 53 publications

References 43 publications

Ternary donor–acceptor phosphine oxide hosts with peculiar high energy gap for efficient blue electroluminescence

Ternary donor–acceptor phosphine oxide hosts with peculiar high energy gap for efficient blue electroluminescence

Organic and Organometallic Fluorinated Materials for Electronics and Optoelectronics: A Survey on Recent Research

Spirobifluorene‐Based o‐Carboranyl Compounds: Insights into the Rotational Effect of Carborane Cages on Photoluminescence

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