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Synthesis and characterization of novel red-emitting copolymers containing fluorene, diketopyrrolopyrrole, and phenothiazine units

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Abstract

A novel three-component copolymer (PFDP), derived from 9,9-dihexylfluorene, diketopyrrolopyrrole( DPP), and 10-octylphenothiazine, was synthesized through palladium-catalyzed Suzuki polycondensation in good yields. PFDP possessed moderate molecular weight and polydispersity, well-defined structure, and excellent thermal properties with an onset decomposition temperature at 357°C. PFDP in thin film exhibited red photoluminescence from DPP chromophore exclusively, with a peak at 602 nm. Electron-rich phenothiazine units sighificantly improved the injection and transport of holes by incorporating into polymer backbone. Light-emitting device was fabricated in the ITO/PEDOT: PSS/PVK/ polymer/Ba/Al configuration using PFDP as the emitting layer. The device based on PFDP showed red emission [CIE coordinate value (0.62, 0.38)] that was close to the standard red (0.66, 0.34). The results on electroluminescent performance revealed that PFDP may be a promising candidate for the red emitter with a maximum brightness of 259 cd/m2 and a maximum external quantum efficiency of 0.25%.

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References

  1. Burroughes J H, Bradley D D C, Brown A R, Marks R N, Friend R H, Burns P L, Holmes A B. Light-emitting diodes based on conjugated polymers. Nature, 1990, 347(6393): 539–541

    Article  CAS  Google Scholar 

  2. Peng Q, Kang E T, Neoh K G, Neoh K G, Xiao D, Zou D C. Conjugated alternating copolymers of fluorene and 2-pyridine-4-ylidenemalononitrile: Synthesis, characterization and electroluminescent properties. J Mater Chem, 2006, 16: 376–383

    Article  CAS  Google Scholar 

  3. Hou Q, Xu Y, Yang W, Yuan M, Peng J, Cao Y. Novel red-emitting fluorene-based copolymers. J Mater Chem, 2002, 12: 2887–2892

    Article  CAS  Google Scholar 

  4. Peng Q, Lu Z Y, Huang Y, Xie M G, Han S H., Peng J B, Cao Y, Huang W. Synthesis and characterization of new red-emitting polyfluorene derivatives containing electron-deficient 2-pyran-4-ylidenemalononitrile moieties. Macromolecules, 2004, 37: 260–266

    Article  CAS  Google Scholar 

  5. Wu F I, Shin P I, Shu C F. Highly efficient light-emitting diodes based on fluorene copolymer consisting of triarylamine units in the main chain and oxadiazole pendent groups. Macromolecules, 2005, 38: 9028–9036

    Article  CAS  Google Scholar 

  6. Kim J H, You N H, Le H. Electroluminescent copolymers based on dihexylfluorene and 2-{2,6-bis[2-(4-diphenylaminophenyl)vinyl] pyran-4-ylidene} malononitrile units. J Polym Sci Part A: Polym Chem, 2006, 44: 3729–3737

    Article  CAS  Google Scholar 

  7. Chou N S, Hwang D H, Jung B J, Cho, Lim E, Lee J, Shim H K. Synthesis, characterization, and electroluminescence of new conjugated polyfluorene derivatives containing various dyes as comonomers. Macromolecules, 2004, 37: 5265–5273

    Article  CAS  Google Scholar 

  8. Cao D R, Liu Q L, Zeng W J, Han S, Peng J, Liu S. Diketopyrrolopyrrole-containing polyfluorenes: Facile method to tune emission color and improve electron affinity. Macromolecules, 2006, 39(24): 8347–8355

    Article  CAS  Google Scholar 

  9. Cao D R, Liu Q L, Zeng W J, Han S, Peng J, Liu S. Synthesis and characterization of novel red-emitting alternating copolymers based on fluorene and diketopyrrolopyrrole derivatives. J Polym Sci Part A: Polym Chem, 2006, 44: 2395–2405

    Article  CAS  Google Scholar 

  10. Rabindranath A R, Zhu Y, Heim I, Tieke B. Red emitting N-functionalized poly(1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole) (poly-DPP): A deeply colored polymer with unusually large stokes shift. Macromolecules, 2006, 39: 8250–8256

    Article  CAS  Google Scholar 

  11. Cho N S, Park J H, Lee S K, Lee J, Shim H K, Park M J, Hwang D H, Jung B J. Saturated and efficient red light-emitting fluorene-based aternating polymers containing phenothiazine derivatives. Macromolecules, 2006, 39: 177–183

    Article  CAS  Google Scholar 

  12. Kong X X, Kulkarni A P, Jeneke S A. Phenothiazine-based conjugated polymers: Synthesis, electrochemistry, and light-emitting properties. Macromolecules, 2003, 36: 8992–8999

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China

    Zhi Qiao, DeRong Cao & JieNa Weng

  2. Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, 510650, China

    QiLin Liu

  3. Institute of Polymer Optoelectronic Materials and Devices, South China University of Technology, Guangzhou, 510640, China

    ZhiCai He, ShaoHu Han & JunBiao Peng

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  1. Zhi Qiao
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  2. DeRong Cao
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  3. QiLin Liu
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  4. JieNa Weng
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  5. ZhiCai He
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  6. ShaoHu Han
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  7. JunBiao Peng
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Correspondence to DeRong Cao.

Additional information

Supported by the National Natural Science Foundation of China (Grant No. 20872038), Science and Technology Planning Project of Guangdong Province, China (Grant No. 2007A010500011), and Research Fund for the Doctoral Program of Higher Education of China (Grant No. 20060561024)

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Qiao, Z., Cao, D., Liu, Q. et al. Synthesis and characterization of novel red-emitting copolymers containing fluorene, diketopyrrolopyrrole, and phenothiazine units. Sci. China Ser. B-Chem. 52, 2038–2042 (2009). https://doi.org/10.1007/s11426-009-0188-7

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  • DOI: https://doi.org/10.1007/s11426-009-0188-7

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