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Journal of Fluorescence

, Volume 24, Issue 4, pp 1215–1224 | Cite as

New spiro[benzotetraphene-fluorene] Derivatives: Synthesis and Application in Sky-Blue Fluorescent Host Materials

  • Jae-Ryung Cha
  • Chil-Won Lee
  • Myoung-Seon Gong
ORIGINAL PAPER

Abstract

Blue light-emitting spiro[benzotetraphene-fluorene] (SBTF)-based host materials, 3-(1-naphthyl)-10-naphthylspiro[benzo[ij]tetraphene-7,9′-fluorene] (1), 3-(2-naphthyl)-10-naphthylspiro[benzo[ij]tetraphene-7,9′-fluorene] (2), and 3-[2-(6-phenyl)naphthyl]-10-naphthylspiro[benzo[ij]tetraphene-7,9′-fluorene] (3) were designed and prepared via multi-step Suzuki coupling reactions. Introducing various aromatic groups into SBTF core lead to a reduction in band gap and a determination of the color purity and luminescence efficiency. Typical sky-blue fluorescent organic light emitting diodes with the configuration of ITO/N,N′-di(1-naphthyl)-N,N′-bis[(4-diphenylamino)phenyl]-biphenyl-4,4′-diamie (60 nm)/N,N,N′,N′-tetra(1-biphenyl)-biphenyl-4,4′-diamine (30 nm)/host: dopant (30 nm, 5 %)/LG201 (electron transporting layer, 20 nm)/LiF/Al were developed using SBTF derivatives as a host material and p-bis(p-N,N-diphenyl-aminostyryl)benzene (DSA-Ph) as a sky-blue dopant material. A device obtained from three materials doped with DSA-Ph showed color purity of 0.148 and 0.239, a luminance efficiency of 7.91 cd/A, and an external quantum efficiency >4.75 % at 5 V.

Keywords

Fluorescence blue OLED Sky blue Spiro[benzotetraphene-fluorene] Color purity 

References

  1. 1.
    Gao ZQ, Mi BX, Chen CH, Cheah KW, Cheng YK, Wen WS (2007) High-efficiency deep blue host for organic light-emitting devices. Appl Phys Lett 90:123506–123508CrossRefGoogle Scholar
  2. 2.
    Lee MT, Chen HH, Lian CH, Tsai CH, Chen CH (2007) Stable styrylamine-doped blue organic electroluminescent device based on 2-methyl-9,10-di(2-naphthyl)anthracene. Appl Phys Lett 85:3301–3303CrossRefGoogle Scholar
  3. 3.
    Tao S, Hong Z, Peng Z, Ju W, Zhang X, Wang P, Wu S, Lee S (2004) Anthracene derivative for a non-doped blue-emitting organic electroluminescence device with both excellent color purity and high efficiency. Chem Phys Lett 397:1–4CrossRefGoogle Scholar
  4. 4.
    Wen SW, Lee MT, Chen CH (2005) Recent development of blue fluorescent OLED materials and devices. J Disp Technol 1:90–99CrossRefGoogle Scholar
  5. 5.
    Huang J, Su JH, Tian H (2012) The development of anthracene derivatives for organic light-emitting diodes. J Mater Chem 22:10977–10989CrossRefGoogle Scholar
  6. 6.
    Xia ZY, Zhang ZY, Su JH, Zhang Q, Fung KM, Lam MK, Li KF, Wong WY, Cheah KW, Tian H, Chen CH (2010) Robust and highly efficient blue light-emitting hosts based on indene-substituted anthracene. J Mater Chem 20:3768–3774CrossRefGoogle Scholar
  7. 7.
    Huang J, Su JH, Li X, Lam MK, Fung KM, Fan HH, Cheah KW, Chen CH, Tian H (2011) Bipolar anthracene derivatives containing hole- and electron-transporting moieties for highly efficient blue electroluminescence devices. J Mater Chem 21:2957–2964CrossRefGoogle Scholar
  8. 8.
    Xia ZY, Su JH, Wong WY, Wang L, Cheah KW, Tian H, Chen CH (2011) High performance organic light-emitting diodes based on tetra(methoxy)-containing anthracene derivatives as a hole transport and electron-blocking layer. J Mater Chem 21:8382–8388Google Scholar
  9. 9.
    Shi J, Tang CW (2002) Anthracene derivatives for stable blue-emitting organic electroluminescence devices. Appl Phys Lett 80:3201–8203CrossRefGoogle Scholar
  10. 10.
    Salbeck J, Yu N, Bauer J, Weissörtel F, Bestgen H (1997) Low molecular organic glasses for blue electroluminescence. Synth Met 91:209–215CrossRefGoogle Scholar
  11. 11.
    O’Brien DF, Burrows PE, Forrest SR, Konne BE, Loy DE, Thompson ME (1998) Hole transporting materials with high glass transition temperatures for use in organic light-emitting devices. Adv Mater 10:1108–1112CrossRefGoogle Scholar
  12. 12.
    Salbeck J, Bauer J, Weissörtel F (1997) Spiro linked compounds for use as active materials in organic light emitting diodes. Macromol Symp 125:121–132CrossRefGoogle Scholar
  13. 13.
    Katsuma K, Shirota Y (1998) A novel class of π-electron dendrimers for thermally and morphologically stable amorphous molecular materials. Adv Mater 10:23–26CrossRefGoogle Scholar
  14. 14.
    Bach U, Cloedt KD, Spreitzer H, Gratzel M (2000) Characterization of hole transport in a new class of spiro-linked oligotriphenylamine compounds. Adv Mater 12:1060–1063CrossRefGoogle Scholar
  15. 15.
    Ko CW, Tao YT (2002) 9,9-Bis[4-[di-(p-biphenyl)aminophenyl]]fluorene: a high Tg and efficient hole transporting material for electroluminescent devices. Synth Met 126:37–41CrossRefGoogle Scholar
  16. 16.
    Kim KS, Jeon YM, Kim JW, Lee CW, Gong MS (2008) Blue light-emitting OLED using new spiro[fluorene-7, 9′-benzofluorene] host and dopant materials. Org Electron 9:797–804CrossRefGoogle Scholar
  17. 17.
    Jeon SO, Jeon YM, Kim JW, Lee CW, Gong MS (2008) Blue organic light-emitting diode with improved color purity using 5-naphthyl-spiro[fluorene-7,9′-benzofluorene]. Org Electron 9:522–532CrossRefGoogle Scholar
  18. 18.
    Kim KS, Jeon YM, Lee HS, Kim JW, Lee CW, Jang JG et al (2008) (2008) Blue organic electroluminescent devices based on the spiro[fluorene-7, 9′-benzofluorene] derivatives as host and dopant materials. Synth Met 158:870–875CrossRefGoogle Scholar
  19. 19.
    Jeon YM, Kim JW, Lee CW, Gong MS (2009) Blue organic light-emitting diodes using novel spiro[fluorene-benzofluorene]-type host materials. Dyes Pigments 83:66–71CrossRefGoogle Scholar
  20. 20.
    Jeon SO, Jeon YM, Kim JW, Lee CW, Gong MS (2009) Spiro[fluorene-7,9′-benzofluorene] host and dopant materials for blue light-emitting electroluminescence device. Synth Met 159:1147–1152CrossRefGoogle Scholar
  21. 21.
    Kim KS, Lee HS, Jeon YM, Kim JW, Lee CW, Gong MS (2009) Blue light-emitting diodes from 2-(10-naphthylanthracene)-spiro[fluorene-7,9′-benzofluorene] host material. Dyes Pigments 81:174–179CrossRefGoogle Scholar
  22. 22.
    Kim JY, Lee CW, Jang JG, Gong MS (2012) Orange phosphorescent organic light-emitting diodes using new spiro[benzoanthracene-fluorene]-type host materials. Dyes Pigments 94:304–313CrossRefGoogle Scholar
  23. 23.
    Kim MJ, Lee CW, Gong MS (2014) New spirobenzoanthracene derivatives with dinaphthylanthracene core: synthesis and application in sky-blue fluorescent host materials. Dyes Pigments 105:202–207CrossRefGoogle Scholar
  24. 24.
    Gong MS, Lee HS, Jeon YM (2010) Highly efficient blue OLED based on 9-anthracene spirobenzofluorene derivatives as host materials. J Mater Chem 20:10735–10746CrossRefGoogle Scholar
  25. 25.
    Danel K, Huang TH, Lin JT, Tao YT, Chuen CH (2002) Blue-emitting anthracenes with end-capping diarylamines. Chem Mater 14:3860–3865CrossRefGoogle Scholar
  26. 26.
    Aziz H, Popovic ZD (2004) Degradation phenomena in small-molecule organic light emitting devices. Chem Mater 16:4522–4532CrossRefGoogle Scholar
  27. 27.
    Kim SK, Yang B, Ma Y, Lee JH, Park JW (2008) Exceedingly efficient deep-blue electroluminescence from new anthracenes obtained using rational molecular design. J Mater Chem 18:3376–3384Google Scholar
  28. 28.
    Cheon JW, Lee CW, Gong MS, Geum N (2004) Chemiluminescent properties of blue fluorophores containing naphthalene unit. Dyes Pigments 61:23–30CrossRefGoogle Scholar
  29. 29.
    Jang SE, Joo CW, Yook KS, Kim JW, Lee CW, Lee JY (2010) Thermally stable fluorescent blue organic light-emitting diodes using spirobifluorene based anthracene host materials with different substitution Position. Synth Met 160:1184–1188CrossRefGoogle Scholar
  30. 30.
    Lin HP, Zhou F, Zhang XW, Yu DB, Li J, Zhang L, Jiang XY, Zhang ZL (2011) Enhanced color stability and improved performance in white organic light-emitting devices by utilizing a double-graded structure. Synth Met 161:1133–1136CrossRefGoogle Scholar
  31. 31.
    Park JK, Lee KH, Kang S, Lee JY, Park JS, Seo JH, Kim YK, Yoon SS (2010) Highly efficient blue-emitting materials based on 10-naphthylanthracene derivatives for OLEDs. Org Electron 11:905–915CrossRefGoogle Scholar
  32. 32.
    Adachi C, Baldo MA, Thopmson ME, Forrest SR (2001) Nearly 100 % internal phosphorescence efficiency in an organic light-emitting device. J Appl Phys 90:5048–5051CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Department of Nanobiomedical Science and BK21 PLUS NBM Global Research CenterDankook UniversityChungnamRepublic of Korea
  2. 2.Department of Polymer Science and EngineeringDankook UniversityYonginRepublic of Korea

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