Synthesis and electro-optical properties of spiro-bifluorenylvinylene-based polymers for light-emitting diodes applications

Shin, Won Suk; Joo, Moon-Kyu; Kim, Sung Chul; Park, Sung Min; Jin, Sung‐Ho; Shim, Joongpyo; Lee, Jin Kook; Lee, Jae Woo; Gal, Yeong‐Soon; Jenekhe, Samson A.

doi:10.1039/b607944j

Cited by 8 publications

(2 citation statements)

References 45 publications

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“…Figure 4 a shows the experimental spectra of the pseudoextinction coefficient, <k>, of the various samples. Spectra of H1 , H3 , H4 and H6 show six main peaks, at 2.6 eV (477 nm) due to the NB-CT transitions, at 3.14 eV (395 nm) related to the π–π* transitions of the conjugated molecule backbones, at 3.99 eV (311 nm),which is characteristic of triphenylamine-derivates [ 21 ], at 4.25 eV (292 nm) due to the vinyl-thiophene-derivates, and at 5.24 eV (234 nm) and at 5.91 eV (210 nm), due to thiophene- and benzene-derivates, respectively [ 22 , 23 ]. Spectra of H2 and H5 , on the contrary, show that the CT transition is shifted to lower energies, at 2.35 eV (528 nm), while the π–π* transitions of the conjugated molecule backbones is blue-shifted and damped.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

et al. 2022

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We have synthetized two classes of dibenzofulvene-arylamino derivatives with an H-shape design, for a total of six different molecules. The molecular structures consist of two D-A-D units connected by a thiophene or bitiophene bridge, using diarylamino substituents as donor groups anchored to the 2,7- (Group A) and 3,6- (Group B) positions of the dibenzofulvene backbone. The donor units and the thiophene or bithiophene bridges were used as chemico-structural tools to modulate electro-optical and morphological-electrical properties. A combination of experiments, such as absorption measurements (UV-Vis spectroscopy), cyclic voltammetry, ellipsometry, Raman, atomic force microscopy, TD-DFT calculation and hole-mobility measurements, were carried out on the synthesized small organic molecules to investigate the differences between the two classes and therefore understand the relevance of the molecular design of the various properties. We found that the anchoring position on dibenzofulvene plays a crucial key for fine-tuning the optical, structural, and morphological properties of molecules. In particular, molecules with substituents in 2,7 positions (Group A) showed a lower structural disorder, a larger molecular planarity, and a lower roughness.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

et al. 2022

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“…The obtainment of PFVs is commonly pursued by three major synthetic strategies: the Wittig condensation, the Heck reaction, and the widely preferred Gilch route . Concerning the preparation of random fluorenylenevinylene copolymers, the properties of which have stimulated the interest of various research groups, as confirmed by a very recent work of Jin et al., the Gilch approach is the most versatile, because the Wittig condensation and the Heck reaction are mostly employed for synthesis of alternating PFVs copolymers. In this framework, we have recently proposed a versatile method for the obtainment of random PFVs by a one-pot Suzuki−Heck cascade reaction using potassium vinyltrifluoroborate as ethylene equivalent, and the suitable aryl dibromides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Stability, and Electroluminescent Properties of Random Poly(2,7-fluorenylenevinylene-co-3,6-carbazolylenevinylene) Obtained by a Suzuki−Heck Cascade Reaction

et al. 2007

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The synthesis of a series of new random poly(9,9-dioctyl-2,7-fluorenylenevinylene-co-N-octyl-3,6-carbazolylenevinylene) copolymers at 20-80% mol/mol of carbazole (P2-P6) was achieved by a versatile Suzuki-Heck reaction cascade between the suitable dibromoaryl derivatives at different monomer ratios and potassium vinyltrifluoroborate. Their properties have been investigated by 1 H NMR, IR, TGA, DSC, cyclic voltammetry, UV-vis, and photoluminescence and compared to those of poly(9,9-dioctyl-2,7-fluorenylenevinylene) (P1) obtained by the same method. The control of the π-conjugation extension and the inductive effects, determined by the amount of carbazolyl-3,6-ene moieties, permitted the modulation of the HOMO and LUMO energy levels of these materials without remarkably modifying their emission properties. Furthermore, different from poly-(9,9-dioctylfluorene), a good spectral stability in the solid state was proven for P1 after a thermal annealing under air at 130 °C. The electroluminescence properties of the materials were tested by constructing OLED devices of ITO/PEDOT-PSS/P1-P6/Ca/Al configuration. The improvement of the device performances for P2-P4 (20-50 mol/mol of carbazole) with respect to P1 was attributed to the better hole transport in the material because of the presence of carbazole units. The better performances of P5 (450 cd/m 2 at 22 V, 0.0225 cd/A at 22 V) were ascribed to the easier injection of electrons in the device with respect to the other copolymers, as a consequence of its higher electron affinity. These figures of merit could be improved by inserting a suitable electron injecting layer (Alq 3 ) between the cathode and P5 (890 cd/m 2 at 18 V, 0.0435 cd/A at 10 V).

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Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Poriel¹,

Liang²,

Rault‐Berthelot³

et al. 2007

Chemistry A European J

131

229

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A series of new dispiro[fluorene-9',6,9'',12-indeno[1,2b]fluorenes] (DSF-IFs) has been synthesised. These new building blocks for blue-light-emitting devices and electroactive polymers combine indenofluorene (IF) and spirobifluorene (SBF) properties. We report here our synthetic investigations towards these new structures and their thermal, structural, photophysical and electrochemical properties. These properties have been compared to those of IF and SBF. We also report the anodic oxidation of DSF-IFs that leads to the formation of non-soluble transparent three-dimensional polymers. The structural and electrochemical behaviour of these polymers has been studied. The first application of these building blocks as new blue-light-emitting materials in organic light-emitting diodes (OLED) is also reported.

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Synthesis and electro-optical properties of spiro-bifluorenylvinylene-based polymers for light-emitting diodes applications

Cited by 8 publications

References 45 publications

Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

Synthesis and Investigation of Electro-Optical Properties of H-Shape Dibenzofulvene Derivatives

Synthesis, Spectral Stability, and Electroluminescent Properties of Random Poly(2,7-fluorenylenevinylene-co-3,6-carbazolylenevinylene) Obtained by a Suzuki−Heck Cascade Reaction

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

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