Polymer Bulletin

, Volume 69, Issue 3, pp 273–289 | Cite as

Synthesis and characterization of new polyfluorene derivatives: using phenanthro[9,10-d]imidazole group as a building block for deep blue light-emitting polymer

  • Zhiming Wang
  • Zhao Gao
  • Shanfeng Xue
  • Yulong Liu
  • Wensi Zhang
  • Cheng Gu
  • Fangzhong Shen
  • Ping Lu
  • Yuguang Ma
Original Paper

Abstract

A series of novel polyfluorene derivatives P1/4, P2/4, and P3/4, containing phenanthro[9,10-d]imidazole group on backbone are designed, synthesized, and well characterized. They all show high-molecular weights, good solubilities, and excellent thermal stabilities. The CV results of all three compounds show the lower LUMO levels and higher HOMO levels than PF. Among them, P3/4 exhibits deep blue emission both in solution and in solid state. The PLED based on P3/4 shows higher device performance and locates in the deep blue region with a CIE coordinate of (0.17, 0.08).

Keywords

Deep blue emission Phenanthrenequinone Imidazole Multifunctional Polymer 

References

  1. 1.
    Burroughes JH, Bradley DDC, Brown AR (1990) Light-emitting diodes based on conjugated polymers. Nature 347:539CrossRefGoogle Scholar
  2. 2.
    Braun D, Heeger AJ (1991) Visible light emission from semiconducting polymer diodes. Appl Phys Lett 58:1982CrossRefGoogle Scholar
  3. 3.
    Hebner TR, Wu CC, Marcy D, Lu MH, Sturm JC (1998) Ink-jet printing of doped polymers for organic light emitting devices. Appl Phys Lett 72:519CrossRefGoogle Scholar
  4. 4.
    Chang SC, Liu J, Bharathan J, Yang Y, Onohara J, Kido J (1999) Multicolour organic light-emitting diodes processed by hybrid inkjet printing. Adv Mater 11:734CrossRefGoogle Scholar
  5. 5.
    Fu YQ, Li Y, Li J, Yan SK, Bo ZS (2004) High molecular weight dendronized poly(fluorene)s with peripheral carbazole groups: synthesis, characterization, and properties. Macromolecules 37:6395CrossRefGoogle Scholar
  6. 6.
    Luo J, Peng J, Cao Y, Hou Q (2005) High-efficiency red light-emitting diodes based on polyfluorene copolymers with extremely low content of 4,7-di-2-thienyl-2,1,3-benzothiadiazole-comparative studies of intrachain and interchain interaction. Appl Phys Lett 87:261103CrossRefGoogle Scholar
  7. 7.
    Pu YJ, Higashidate M, Nakayama KI, Kido J (2008) Solution-processable organic fluorescent dyes for multicolor emission in organic light emitting diodes. J Mater Chem 18:4183CrossRefGoogle Scholar
  8. 8.
    Zhang Y, Boer BD, Blom PWM (2009) Controllable molecular doping and charge transport in solution-processed polymer semiconducting layers. Adv Funct Mater 19:1901CrossRefGoogle Scholar
  9. 9.
    Lu P, Zhang HQ, Shen FZ, Yang B, Li D, Ma YG (2003) A wide-bandgap semiconducting polymer for ultraviolet and blue light emitting diodes. Macromol Chem Phys 204:2274CrossRefGoogle Scholar
  10. 10.
    Levermore PA, Jin R, Wang XH, Mello JC, Bradley DDC (2009) Organic light-emitting diodes based on poly(9,9-dioctylfluorene-co-bithiophene) (F8T2). Adv Funct Mater 19:950CrossRefGoogle Scholar
  11. 11.
    Yang RQ, Tian RY, Yan JG, Zhang Y, Yang J, Hou Q (2005) Deep-red electroluminescent polymers: synthesis and characterization of new low-band-gap conjugated copolymers for light-emitting diodes and photovoltaic devices. Macromolecules 38:244CrossRefGoogle Scholar
  12. 12.
    Yu CY, Chen CP, Chan SH, Hwang GW, Ting C (2009) Thiophene/phenylene/thiophene-based low-bandgap conjugated polymers for efficient near-infrared photovoltaic applications. Chem Mater 21:3262CrossRefGoogle Scholar
  13. 13.
    Jin Y, Kim Y, Kim SH, Song S, Woo HY, Lee K, Suh H (2008) Novel green-light-emitting polymers based on cyclopenta[def]phenanthrene. Macromolecules 41:5548CrossRefGoogle Scholar
  14. 14.
    Zhen CG, Chen ZK, Liu QD, Dai YF, Shin RYC, Chang SY, Kieffer J (2009) Fluorene-based oligomers for highly efficient and stable organic blue-light-emitting diodes. Adv Mater 21:2425CrossRefGoogle Scholar
  15. 15.
    Jeon SO, Jang SE, Son HS, Lee JY (2011) External quantum efficiency above 20% in deep blue phosphorescent organic light-emitting diodes. Adv Mater 23:1436CrossRefGoogle Scholar
  16. 16.
    Huang CW, Peng KY, Liu CY, Jen TH, Yang NJ, Chen SA (2008) Creating a molecular-scale graded electronic profile in a single polymer to facilitate hole injection for efficient blue electroluminescence. Adv Mater 20:3709CrossRefGoogle Scholar
  17. 17.
    Tseng SR, Li SY, Meng HF (2007) High-efficiency blue multilayer polymer light-emitting diode based on poly9,9-dioctylfluorene. J Appl Phys 101:084510CrossRefGoogle Scholar
  18. 18.
    Lee TW, Kim MG, Kim SY, Park SH, Kwon O, Noh T, Oh TS (2006) Hole-transporting interlayers for improving the device lifetime in the polymer light-emitting diodes. Appl Phys Lett 89:123505CrossRefGoogle Scholar
  19. 19.
    Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA (2004) Electron transport materials for organic light-emitting diodes. Chem Mater 16:4556CrossRefGoogle Scholar
  20. 20.
    Strohriegl P, Grazulevicius JV (2002) Charge-transporting molecular glasses. Adv Mater 14:1439CrossRefGoogle Scholar
  21. 21.
    Shirota Y, Kageyama H (2007) Charge carrier transporting molecular materials and their applications in devices. Chem Rev 107:953CrossRefGoogle Scholar
  22. 22.
    Miteva T, Meisel A, Knoll W, Nothofer HG, Scherf U, Muller DC, Meerholz K, Yasuda A, Neher D (2001) Improving the performance of polyfluorene-based organic light-emitting diodes via end-capping. Adv Mater 13:565CrossRefGoogle Scholar
  23. 23.
    Hung MC, Chen SA, Chen SH, Su AC (2005) Blue-emitting poly(2,7-pyrenylene)s: synthesis and optical properties. J Am Chem Soc 127:14576CrossRefGoogle Scholar
  24. 24.
    Kawano S, Yang C, Ribas M, Baluschev S, Baumgarten M, Mullen K (2008) Blue-emitting poly(2,7-pyrenylene)s: synthesis and optical properties. Macromolecules 41:7933CrossRefGoogle Scholar
  25. 25.
    Saleh M, Park Y, Baumgarten M, Kim J, Mullen K (2009) Conjugated triphenylene polymers for blue OLED devices. Macromol Rapid Commun 30:1279CrossRefGoogle Scholar
  26. 26.
    Morin JF, Leclerc M, Ades D, Siove A (2005) Polycarbazoles: 25 years of progress. Macromol Rapid Commun 26:761CrossRefGoogle Scholar
  27. 27.
    Lu JP, Tao Y, Diorio M, Li YN, Ding JF, Day M (2004) Pure deep blue light-emitting diodes from alternating fluorene/carbazole copolymers by using suitable hole-blocking materials. Macromolecules 37:2442CrossRefGoogle Scholar
  28. 28.
    Wu FI, Shih PI, Shu CF, Tung YL, Chi Y (2005) Highly efficient light-emitting diodes based on fluorene copolymer consisting of triarylamine units in the main chain and oxadiazole pendent groups. Macromolecules 38:9028CrossRefGoogle Scholar
  29. 29.
    Chien CH, Shih P, Wu FI, Shu CF, Yun C (2007) Polyfluorene presenting dipolar pendent groups and its application to electroluminescent devices. J Polym Sci A 45:2073CrossRefGoogle Scholar
  30. 30.
    Zhu Y, Gibbons KM, Kulkarni AP, Jenekhe SA (2007) Polyfluorenes containing dibenzo[a,c]phenazine segments: synthesis and efficient blue electroluminescence from intramolecular charge transfer states. Macromolecules 40:804CrossRefGoogle Scholar
  31. 31.
    Jenekhe SA, Lu L, Alam MM (2001) New conjugated polymers with donor-acceptor architectures: synthesis and photophysics of carbazole–quinoline and phenothiazine–quinoline copolymers and oligomers exhibiting large intramolecular charge transfer. Macromolecules 34:7315CrossRefGoogle Scholar
  32. 32.
    Chen CH, Huang WS, Lai MY, Tsao WC, Lin JT, Wu YH, Ke TH, Chen LY, Wu CC (2009) Versatile, benzimidazole/amine-based ambipolar compounds for electroluminescent applications: single-layer, blue, fluorescent OLEDs, hosts for single-layer. Phosphorescent OLEDs. Adv Funct Mater 19:2661CrossRefGoogle Scholar
  33. 33.
    Shi J, Tang CW, Chen CH (1997) US Patent No. 5,646,948Google Scholar
  34. 34.
    Lo SC, Male NAH, Markham JPJ, Magennis SW, Burn PL, Salata OV, Samuel IDW (2002) Green phosphorescent dendrimer for light-emitting diodes. Adv Mater 14:975Google Scholar
  35. 35.
    Wang ZM, Lu P, Chen SM, Gao Z, Shen FZ, Zhang WS, Xu YX, Kwok HS, Ma YG (2011) Phenanthro[9,10-d]imidazole as a new building block for blue light emitting materials. J Mater Chem 21:5415Google Scholar
  36. 36.
    Lu P, Zhang HQ, Shen FZ, Yang B, Li D, Ma YG, Chen XF, Li JH, Tamai N (2003) A wide-bandgap semiconducting polymer for ultraviolet and blue light emitting diodes. Macromol Chem Phys 204:2274CrossRefGoogle Scholar
  37. 37.
    Wang HP, Lu P, Wang BL, Qiu S, Liu MR, Hanif M, Cheng G, Liu SY, Ma YG (2007) A water-soluble π-conjugated polymer with up to 100 mg/mL solubility. Macromol Rapid Commun 28:1645CrossRefGoogle Scholar
  38. 38.
    Muddasir H, Lu P, Li M, Zheng Y, Xie ZQ, Ma YG, Li D, Li JH (2007) Synthesis, characterization, electrochemistry and optical properties of a novel phenanthrenequinone-alt-dialkylfluorene conjugated copolymer. Polym Int 56:1507CrossRefGoogle Scholar
  39. 39.
    Wang ZM, Lu P, Zhang WS, Shen FZ, Hanif M, Ma YG (2009) Dual tuning of emission color and electron injection properties through in situ chemical reaction in a conjugated polymer containing 9,10-phenanthrenequinone. Macromol Chem Phys 23:2029CrossRefGoogle Scholar
  40. 40.
    Grisorio R, Suranna GP, Mastrorilli P, Nobile CF (2007) A versatile synthesis for new 9,10-bis(4-alkoxyphenyl)-2,7-diiodophenanthrenes: useful precursors for conjugated polymers. Org Lett 9:3149CrossRefGoogle Scholar
  41. 41.
    Chang YT, Hsu SL, Su MH, Wei KH (2007) Soluble phenanthrenyl-imidazole-presenting regioregular poly(3-octylthiophene) copolymers having tunable bandgaps for solar cell applications. Adv Funct Mater 17:3326CrossRefGoogle Scholar
  42. 42.
    Chang YT, Hsu SL, Chen GY (2008) Intramolecular donor–acceptor regioregular poly(3-hexylthiophene)s presenting octylphenanthrenyl-imidazole moieties exhibit enhanced charge transfer for heterojunction solar cell applications. Adv Funct Mater 18:1CrossRefGoogle Scholar
  43. 43.
    Chang YT, Hsu SL, Su MH, Wei KH (2009) Intramolecular donor–acceptor regioregular poly(hexylphenanthrenyl-imidazole thiophene) exhibits enhanced hole mobility for heterojunction solar cell applications. Adv Mater 21:2093CrossRefGoogle Scholar
  44. 44.
    Miyaura M, Suzuki A (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95:2457CrossRefGoogle Scholar
  45. 45.
    Remmers M, Schulze M, Wegner G (1996) Characterisation and properties of poly(2,5-dialkoxy-oligophenylen-vinylene)s, poly(2,5-dialkoxy-oligophenylen-acetylene)s and related light-emitting polymers. Macromol Rapid Commun 17:239CrossRefGoogle Scholar
  46. 46.
    Wu YG, Li J, Fu YQ, Bo ZS (2004) Synthesis of extremely stable blue light emitting poly(spirobifluorene)s with Suzuki polycondensation. Org Lett 6:3485CrossRefGoogle Scholar
  47. 47.
    Li ZA, Ye SH, Liu YQ, Yu G, Wu WB, Qin JG, Li Z (2010) New hyperbranched conjugated polymers containing hexaphenylbenzene and oxadiazole units: convenient synthesis and efficient deep blue emitters for PLEDs application. J Phys Chem B 114:9101CrossRefGoogle Scholar
  48. 48.
    Tang S, Liu MR, Lu P, Xia H, Li M, Xie ZQ, Shen FZ, Gu C, Wang H, Yang B, Ma YG (2007) A molecular glass for deep-blue organic light-emitting diodes comprising a 9,9′-spirobifluorene core and peripheral carbazole groups. Adv Funct Mater 17:2869CrossRefGoogle Scholar
  49. 49.
    Wang ZM, Lu P, Xue SF, Gu C, Lv Y, Zhu Q, Wang H, Ma YG (2011) A solution-processable deep red molecular emitter for non-doped organic red-light-emitting diodes. Dyes Pigments 91:356CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Zhiming Wang
    • 1
    • 2
  • Zhao Gao
    • 1
  • Shanfeng Xue
    • 1
  • Yulong Liu
    • 1
  • Wensi Zhang
    • 1
  • Cheng Gu
    • 1
  • Fangzhong Shen
    • 1
  • Ping Lu
    • 1
  • Yuguang Ma
    • 1
  1. 1.State Key Laboratory of Supramolecular Structure and MaterialsJilin UniversityChangchunPeople’s Republic of China
  2. 2.School of Petrochemical EngineeringShenyang University of TechnologyLiaoyangPeople’s Republic of China

Personalised recommendations