Doubly Ortho-Linked Quinoxaline/Diphenylfluorene Hybrids as Bipolar, Fluorescent Chameleons for Optoelectronic Applications

Chen, Chien‐Tien; Wei, Yi; Lin, Jun; Moturu, Murthy V. R. K.; Chao, Wei-San; Tao, Yu‐Tai; Chien, Chia-Hung

doi:10.1021/ja062660v

Cited by 130 publications

(61 citation statements)

References 30 publications

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“…Furthermore, isolation of the pi electron conjugated system, high solubility, and suppression of excimer formation as used solid-state fluorescent dye. Spiro-type derivatives containing fluorene and benzofluorene as OLED fluorescent materials have received a great deal of attention because asymmetrical spiro compounds with a naphthalene group not only can preserve the inherent characteristics of a spiro compound such as morphological stability, high glass transition temperature, and amorphous properties but also provide a variety of substituents on the aromatic ring of spiro molecule resulting in the formation of conjugation controlled OLED host and dopant materials, [14][15][16][17][18][19][20][21][22][23][24] In this study, we report the synthesis of novel spiro[benzo-[c]fluorene-7,9'-fluorene] (SBFF)-type OLED materials using the Suzuki reaction. Various properties such as UV-Vis absorption, photoluminescence (PL), photoelectron spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) were evaluated.…”

Section: -13mentioning

confidence: 99%

Synthesis of New Spiro[benzo[c]fluorene-7,9'-fluorene] Dimers and Their Optical Properties

Lee¹,

Gong²

2013

Bulletin of the Korean Chemical Society

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) were successfully prepared from the corresponding halogen and boronic acid derivatives through the Suzuki coupling reaction, respectively. Chemical structures were confirmed by 1 H nuclear magnetic resonance (NMR), 13C NMR, Fourier transforminfrared spectrscopy, mass spectroscopy, and elemental analysis. The thermal properties were determined by differential scanning calorimetry and thermal gravimetric analysis. The relationships between the optical and electrochemical properties and the combined positions between these dimers were systematically investigated using UV-vis, photoluminescence (PL), and photoelectron spectroscopy. These five dimers exhibited high fluorescent quantum yields and good morphological stability with high glass transition states > 174°C. Dimer 7 showed a UV absorbance peak at 353 nm, emission PL peak at 424 nm, and quantum efficiency of 0.62 in a cyclohexane solution.

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Section: -13mentioning

confidence: 99%

Synthesis of New Spiro[benzo[c]fluorene-7,9'-fluorene] Dimers and Their Optical Properties

Lee¹,

Gong²

2013

Bulletin of the Korean Chemical Society

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“…Nevertheless, both the 7 and 8 can function as ambipolar EL materials with more balanced charge transporting (CT) properties in view of the satisfactory OLED performances. [17] Molecules with ambipolar CT and high solid-state PL quantum yields are especially attractive as efficient emitters for high-performance OLEDs. [18] The electroluminescence from ambipolar molecules can originate from intramolecular charge transfer excited states formed by the annihilation reaction between the D radical cations and the A radical anions.…”

Section: Organic Ambipolar Conjugated Molecules For Fluorescent Emittersmentioning

confidence: 99%

Organic Ambipolar Conjugated Molecules for Electronics: Synthesis and Structure–Property Relationships

Jiang

2010

Macromol. Rapid Commun.

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The field of organic electronics has been developed vastly in the past two decades, and the performance and lifetime of these devices are critically dependent on the materials development, device design, deposition processes, and modeling, among which the active materials of organic semiconductor play a crucial role. The unique properties of organic semiconductor are largely based on the versatility to synthesize multifunctional organic conjugated materials by judicious molecular design. To effectively adjust the optoelectronic properties, especially energy levels, of organic semiconductor, the scientists have presented a synthesis methodology of organic ambipolar conjugated molecules, in which typical p-dope type and n-dope type segments are incorporated into one molecule. The present review summarizes the progress on organic ambipolar conjugated molecules for electronics in the past few years. Some issues to be addressed are also highlighted and discussed.

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“…19 Various successful procedures have been developed in the last few years to frustrate the ACQ process. These include (a) distorted/twisted luminophores; [20][21][22] (b) long aliphatic chain substitution of the core luminophore; [23][24][25] (c) spiro compounds; [26][27][28] (d) insertion of bulky substituents to the core luminophore [29][30][31] and (e) a dipole stacking model. 32 All these approaches make the luminophore highly emissive in the solid state because of prevention of aggregation quenching at a molecular level.…”

Section: Introductionmentioning

confidence: 99%

Packing directed beneficial role of 3-D rigid alicyclic arms on the templated molecular aggregation problem

et al. 2015

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Subtle changes in molecular structure have been used to alter the molecular packing and optical properties of organic luminophores. Thus it is important to study simple and advantageous structural modification to overcome limitations of aggregation quenching of fluorescence. Planar conjugated organic compounds are unlikely to be used in OLED devices as they suffer with luminescence weakening due to p-p cofacial stacking and excimer formation in the solid state. To avoid such critical issues, doped device architecture for OLED devices has widely been adopted which actually complicates the device fabrication process. Thus an approach for delimiting these drawbacks using simple methodologies is highly desirable for cost effective OLED device fabrication. In this context, two 3-dimensional rigid arms have been introduced into a planar benzo[h]chromen-2-one core, which suffers from aggregation caused quenching, as peripheral substituents to tune the molecular packing and subsequently their optical properties. The resultant compounds 1 and 2 have been tested for non-doped and doped OLED device application. Compound 1 was found to be highly thermally stable with a decomposition temperature of 344 C. Single crystal XRD studies helped to elucidate that voluminous ring substituents are capable of eradicating co-facial p-p stacking by increasing the intermolecular distance and hence the luminescence in the solid state could be regenerated. This tuning of intermolecular distance between molecules helped to mitigate the close packed arrangement at a molecular level and also provided the bulk with the enhanced emission property. Electroluminescence from a pristine layer of compound 1 was possible. Thus an approach enabling planar luminophores to be used in OLED applications utilizing thin films of structurally engineered luminophores has been presented.

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Doubly Ortho-Linked Quinoxaline/Diphenylfluorene Hybrids as Bipolar, Fluorescent Chameleons for Optoelectronic Applications

Cited by 130 publications

References 30 publications

Synthesis of New Spiro[benzo[c]fluorene-7,9'-fluorene] Dimers and Their Optical Properties

Synthesis of New Spiro[benzo[c]fluorene-7,9'-fluorene] Dimers and Their Optical Properties

Organic Ambipolar Conjugated Molecules for Electronics: Synthesis and Structure–Property Relationships

Packing directed beneficial role of 3-D rigid alicyclic arms on the templated molecular aggregation problem

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