Three-Dimensional Structures Based on the Fusion of Chrysene and Spirobifluorene Chromophores for the Development of Blue OLEDs

Lee, Hayoon; Jung, Hyocheol; Kang, Seokwoo; Heo, Jin Hyuck; Im, Sang Hyuk; Park, Jong‐Wook

doi:10.1021/acs.joc.7b03008

Cited by 21 publications

(10 citation statements)

References 33 publications

(34 reference statements)

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“…It can be seen that the introduction of PAEF can improve current density of the devices even at 30 wt% after optimization, and the reasons are ascribed to the follows: 1) Deserved to be mentioned, the diarylfluorene structure in PAEF backbone is widely used as a star unit for building blue light‐emitting diode. [ 42–46,50,51 ] As shown in Figure S26 in the Supporting Information, it is apparent that PAEF has a broad and strong photoluminescence (PL) manner around 530 nm, while PM6 film exhibits weak PL emission around 670 nm. The spectral overlap between PL spectrum of PAEF and absorption spectrum of PM6 can well support the Dexter or Förster resonance energy transfer between PAEF and PM6, which is responsible for the increased J SC ’s.…”

Section: Resultsmentioning

confidence: 99%

A Universal Method to Enhance Flexibility and Stability of Organic Solar Cells by Constructing Insulating Matrices in Active Layers

Han

Bao

Huang

et al. 2020

Adv Funct Materials

113

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With the rapid development of power conversion efficiency (PCE), flexibility–stability of organic solar cells (OSCs) are becoming one of the primary barriers for commercialization. This work shows that insulating poly(aryl ether) (PAE) resins have highly twisted‐stiff backbones without any side chains, which possess excellent mechanical stability, thermal stability, and good compatibility with organic photovoltaic materials. After introducing 5 wt% PAE resin as supporting matrices into the bulk heterojunction (BHJ) layer, the device yields a high PCE of 16.13%. Importantly, the devices show impressive flexibility and improved stability with passivated morphology, such as PM6/Y6‐based devices with 30 wt% PAE retains the PCE of 15.17% and exhibits enhanced 4.4‐fold elongation at break (25.07%). This is the recorded stretchability of the BHJ layer for OSCs with PCE > 8%, and morphological changes during tensile deformation are first investigated by in situ wide‐angle X‐ray scattering measurements. The PAE matrices strategy exhibits good universality in the other four photovoltaic systems. These results demonstrate that heat‐resistant PAE resins serve as supporting matrices with a tunneling effect into OSCs without sacrificing photovoltaic performance and simultaneously improve the flexibility and stability of devices, which can play an important role in promoting the development of stable and wearable electronics.

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Section: Resultsmentioning

confidence: 99%

A Universal Method to Enhance Flexibility and Stability of Organic Solar Cells by Constructing Insulating Matrices in Active Layers

Han

Bao

Huang

et al. 2020

Adv Funct Materials

113

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“…Further spiro-fused rigid molecules were synthesized, such as compounds 25, [29] 26 [30] 27, [30] and 28 [31] (Scheme 10), which are exceptional blue emitters that can serve both as structure modulation cores and host materials, in order to achieve the desired emitting properties. For instance, the PLQY of compound 28 reached up to 61 %.…”

Section: Other Extensions Of Condensed Spirobifluorenesmentioning

confidence: 99%

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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“…This substitution pattern drives the electronic properties of SBF compounds. The position C2 forms a para-substituted biphenyl and has significantly contributed to the development of highly efficient SBF-based materials for OE (chart 1b), mainly as emitters in blue Organic Light-Emitting Diodes (OLEDs) 3,5,[7][8][9][10][11][12] but also as electron 13 or hole 14 transporters in OLEDs and even more recently as very efficient threedimensional non-fullerene acceptors in organic solar cells. [15][16][17][18][19] The three other positions of the SBF fragment have been far less described to date but appear nevertheless highly promising to build new OSCs.…”

Section: Introductionmentioning

confidence: 99%

1-Carbazolyl Spirobifluorene: Synthesis, Structural, Electrochemical, and Photophysical Properties

et al. 2019

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The present work reports one of the rare examples of a new emerging family of spirobifluorene derivatives, namely 1-substituted spirobifluorenes. We report the synthesis and the structural, electrochemical and photophysical properties of 9-(9,9'-spirobi[fluorene]-1-yl)-9H-carbazole 1-Cbz-SBF, constructed from the connection of the widely known electron-rich carbazole fragment at the C1 position of spirobifluorene. We show with 1-Cbz-SBF that the substitution at C1 induces two important characteristics which drive the electronic properties. First, there is a complete conjugation breaking between the pending substituent, herein carbazole, and the substituted fluorene. Second, there is a through space interaction between the carbazole and its cofacial fluorene. Thanks to a structure-property relationship approach with its constituting building blocks 9,9'-spirobifluorene SBF and carbazole Cbz, we show how some electronic properties are driven by the carbazole unit such as the HOMO energy level whereas others are driven by the fluorene such as the triplet state energy level. As 1-substituted spirobifluorenyl represents a new and promising molecular scaffold for PhOLED applications and more generally for organic electronics, such study provides fundamental knowledge to design future organic materials for specific applications.

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Three-Dimensional Structures Based on the Fusion of Chrysene and Spirobifluorene Chromophores for the Development of Blue OLEDs

Cited by 21 publications

References 33 publications

A Universal Method to Enhance Flexibility and Stability of Organic Solar Cells by Constructing Insulating Matrices in Active Layers

A Universal Method to Enhance Flexibility and Stability of Organic Solar Cells by Constructing Insulating Matrices in Active Layers

Rigidly Fused Spiro‐Conjugated π‐Systems

1-Carbazolyl Spirobifluorene: Synthesis, Structural, Electrochemical, and Photophysical Properties

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