• Title/Summary/Keyword: Suzuki coupling

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Progress In Commercialization Of Light Emitting Polymers: Dow Polyfluorenes

  • Wu, W.;Inbasekaran, M.;Hudack, M.;Welsh, D.;Yu, W.;Chen, Y.;Wang, C.;Kram, S.;Tacey, M.;Bernius, M.;Fletcher, R.;Kiszka, K.;Munger, S.;O'Brien, J.;Hills, M.
    • 한국정보디스플레이학회:학술대회논문집
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    • 2002.08a
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    • pp.340-343
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    • 2002
  • We report here our recent progress in the development and commercialization of polyfluorenes emitting red, green and blue (ROB) colors as materials for light emitting diodes (LEDs). Our patented version of the Suzuki coupling process has been used to synthesize a variety of fluorenebased homopolymers and copolymers emitting colors across the entire visible spectrum. The optical and electronic properties of the polymers are tailored through selective incorporation of different aromatic units into the polyfluorene backbone. Our latest green emitter, reported herein, provides very efficient devices with a low turn-on voltage of 2.25 V, a peak efficiency of 10.5 Cd/A at 6,600 Cd/$m^2$ at 4.85 V. These devices maintain an efficiency of greater than 10 Cd/A up to 50,000 Cd/$m^2$ and demonstrate very good stability as exemplified by a device half-life of greater than 1,500 hours starting from 1,100 Cd/$m^2$. Considerable progress has also been made with red and blue emitters and will be the subject of this presentation.

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Novel Water-Soluble Polyfluorenes as an Interfacial layer leading to Cathodes-Independent High Performance of Organic Solar Cells

  • Oh, Seung-Hwan;Shim, Hee-Sang;Park, Dong-Won;Jeong, Yon-Kil;Lee, Jae-Kwang;Moon, Seung-Hyeon;Kim, Dong-Yu
    • 한국신재생에너지학회:학술대회논문집
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    • 2009.11a
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    • pp.394-394
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    • 2009
  • Water solubility of conjugated polymers may offer many applications. Potential applications of water-soluble conjugated polymers include the polymer light-emitting diode and new materials for nano and micro hollow-capsules, and bio- or chemo-sensors. We synthesized neutral polyfluorenes containing bromo-alkyl groups by the palladium catalyzed Suzuki coupling reaction. Bromo-alkyl side groups in neutral polyfluorenes were quaternized by tri-methyl amine solution. The electrochemical and optical properties of water-soluble conjugated polymers are discussed. This novel synthesized water-soluble conjugated polymers were used as a interfacial dipole layer between active layer and metal cathode in polymer solar cell for enhancement of open-circuit voltage (Voc), which is one of the most critical factors in determining device characteristics. We also investigated the device performance of polymer solar cell with different metal cathode such as Al, Ag, Au and Cu. In polymer solar cell, novel cationic water-soluble conjugated polymers were inserted between active layer and high-work function cathode (Al, Ag, Au and Cu).

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Solution-Processable Field-Effect Transistors Fabricated Using Aryl Phenoxazine Based Polymers as the Active Layer

  • Yoon, Hye-Seon;Lee, Woo-Hyung;Lee, Ji-Hoon;Lim, Dong-Gun;Hwang, Do-Hoon;Kang, In-Nam
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2371-2376
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    • 2009
  • Three phenoxazine-based conjugated polymers, namely, the aryl substituted phenoxazine homopolymer (P1) as well as the dimeric phenoxazine-fluorene (P2) and phenoxazine-bithiophene (P3) copolymers, were synthesized via the Ni(0) mediated Yamamoto reaction and the palladium-catalyzed Suzuki coupling reaction. The weight-averaged molecular weights ($M_w$) of P1, P2, and P3 were found to be 27,000, 22,000, and 15,000, respectively, and their polydispersity indices were 3.6, 1.8, and 2.1. All the polymers were soluble in common organic solvents such as chloroform, toluene, and so on. The UV-visible absorption maxima for P1, P2, and P3 in the film state were located at 421, 415 and 426 nm, respectively, and the ionization potentials of the polymers ranged between 4.90 and 5.12 eV. All the studied phenoxazine-based polymers exhibited amorphous behavior, as confirmed by X-ray diffraction (XRD) and atomic force microscopy (AFM) studies. Thin film transistors were fabricated using the top-contact geometry. P1 showed much better thin-film-transistor performance than P2 or P3: A thin film of P1 gave a saturation mobility of 0.81 ${\times}\;10^{-3}\;cm^2V^{-1}s^{-1}$ and an on/off ratio of about $10^2$.

Effect of the Length of Side Group Substitution on Optical and Electroluminescene Properties

  • Shin, Hwangyu;Kang, Hyeonmi;Kim, Beomjin;Park, Youngil;Yu, Young-Jun;Park, Jongwook
    • Bulletin of the Korean Chemical Society
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    • v.35 no.10
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    • pp.3041-3046
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    • 2014
  • Blue emitting materials, 9,10-bis-biphenyl-4-yl-anthracene (AC-P), 9,10-bis-[1,1';4',1"]terphenyl-4-yl-anthracene (AC-DP), and 9,10-bis[3",5"-deiphenyltriphenyl-4'-yl]anthracene (AC-TP) were synthesized through boration and Suzuki aryl-aryl coupling reaction. EL performance of blue light-emitters was optimized and improved by varying the chemical structures of the side groups. In the thin film state, the three materials exhibit $PL_{max}$ values in the range of 442-456 nm. EL device with the synthesized compounds in the following configuration was fabricated: ITO/4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA) 60nm/N,N'-bis (naphthalene-1-yl)-N,N'-bis(phenyl)benzidine (NPB) 15nm/synthesized blue emitting materials (30nm)/1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi) 20nm/LiF 1nm/Al 200nm. The current efficiency and C.I.E. value of AC-TP were 3.87 cd/A and (0.15, 0.12). A bulky and non-planar side group helps to prevent ${\pi}-{\pi}^*$ stacking interaction, which should lead to the formation of more reliable amorphous film. This is expected to have a positive effect on the high efficiency of the operating OLED device.

Analysis of the Strain Rate Effect in Electro-Magnetic Forming (전자기 성형에서의 변형률 속도 효과 해석)

  • 곽신웅;신효철;이종수
    • Transactions of the Korean Society of Mechanical Engineers
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    • v.14 no.5
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    • pp.1043-1058
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    • 1990
  • The Strain rate effect in electro-magnetic forming, which is one of the high velocity forming methods, is studied by the finite element method in this paper. The forming process is simplified by neglecting the coupling between magnetic field and work-piece deformation, and the impulsive magnetic pressure is regarded as inner pressure load. A rate-dependent elasto-plastic material model, of which tangential modulus depends of effective strain rate, is proposed. The model is shown to well describe the transient increase of yield stresses, the decreases of the final displacement and yield stress, the decrease of the difference in the distribution of deformation along the axial direction, and the change of deformation mechanism due to strain rate effect. As a result, displacement, final deformed shape, radial velocity, deformation energy, and the changes of effective stress, effective strain and effective strain rate through plastic working are given. Based on the results, the effectiveness of this model and the strain rate effect of the deformation process of the work-piece are discussed.

Fluorene-Based Conjugated Copolymers Containing Hexyl-Thiophene Derivatives for Organic Thin Film Transistors

  • Kong, Ho-Youl;Chung, Dae-Sung;Kang, In-Nam;Lim, Eun-Hee;Jung, Young-Kwan;Park, Jong-Hwa;Park, Chan-Eon;Shim, Hong-Ku
    • Bulletin of the Korean Chemical Society
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    • v.28 no.11
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    • pp.1945-1950
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    • 2007
  • Two fluorene-based conjugated copolymers containing hexyl-thiophene derivatives, PF-1T and PF-4T, were synthesized via the palladium-catalyzed Suzuki coupling reaction. The number-average molecular weights (Mn) of PF-1T and PF-4T were found to be 19,100 and 13,200, respectively. These polymers were soluble in common organic solvents such as chloroform, chlorobenzene, toluene, etc. The UV-vis absorption maximum peaks of PF-1T and PF-4T in the film state were found to be 410 nm and 431 nm, respectively. Electrochemical characterization revealed that these polymers have low highest occupied molecular orbital (HOMO) levels, indicating good resistance against oxidative doping. Thin film transistor devices were fabricated using the top contact geometry. PF-1T showed much better thin-film transistor performance than PF-4T. A thin film of PF- 1T gave a saturation mobility of 0.001-0.003 cm2 V?1 s?1, an on/off ratio of 1.0 × 105, and a small threshold voltage of ?8.3 V. To support TFT performance, we carried out DSC, AFM, and XRD measurements.

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

  • Seo, Jeong-A;Lee, Chil-Won;Gong, Myoung-Seon
    • Bulletin of the Korean Chemical Society
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    • v.34 no.5
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    • pp.1414-1420
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    • 2013
  • Five novel spiro[benzo[c]fluorene-7,9'-fluorene] based dyes, including 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-5-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (7), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (8), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (9), 9-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (10), and 2'-[spiro[benzo[c]-fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (11) were successfully prepared from the corresponding halogen and boronic acid derivatives through the Suzuki coupling reaction, respectively. Chemical structures were confirmed by $^1H$ nuclear magnetic resonance (NMR), $^{13}C$ 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 > $174^{\circ}C$. 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.