The facile synthesis and high efficiency of the red electroluminescent dopant DCINB: A promising alternative to DCJTB

Dyes and Pigments

Volumn 82, Issue 3, 2009, Pages 316-321

  Zhao, Ping ^a   Tang, Hao ^b   Zhang, Qiong ^a   Pi, Yajuan ^a   Xu, Min ^a   Sun, Runguang ^b   Zhu, Weihong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI UNIVERSITY   (China)

Author keywords

Dopant; Electroluminescence; Indoline; Optical properties; Red emitter; Synthesis

Indexed keywords

COST-OF-MANUFACTURING; DICYANOMETHYLENE; DOPANT; ELECTROLUMINESCENCE EFFICIENCIES; ELECTRON DONORS; FACILE SYNTHESIS; FLUORESCENCE QUANTUM YIELDS; HIGH EFFICIENCIES; HIGH YIELDS; INDOLINE; LOW YIELDS; RED DOPANTS; RED EMITTER; SYNTHESIS;

DOPING (ADDITIVES); ELECTROLUMINESCENCE; LIGHT EMISSION; OPTICAL PROPERTIES;

SYNTHESIS (CHEMICAL);

ABSORPTION; INORGANIC COMPOUND; MANUFACTURING; SYNTHESIS;

EID: 64849093160     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.01.016     Document Type: Article

References (38)

1. VanSlyke S.A., Chen C.H., and Tang C.W. Organic electroluminescent devices with improved stability. Appl Phys Lett 69 (1996) 2160-2162
2. Young R.H., Tang C.W., and Marchetti A.P. Current-induced fluorescence quenching in organic light-emitting diodes. Appl Phys Lett 80 (2002) 874-876
3. Kwon T.W., Alam M.M., and Jenekhe S.A. n-Type conjugated dendrimers: convergent synthesis, photophysics, electroluminescence, and use as electron-transport materials for light-emitting diodes. Chem Mater 16 (2004) 4657-4666
4. Tao Y.T., Wang Q., Yang C.L., Zhang K., Wang Q., Zou T.T., et al. Solution-processable highly efficient yellow- and red-emitting phosphorescent organic light emitting devices from a small molecule bipolar host and iridium complexes. J Mater Chem 18 (2008) 4091-4096
5. Meng H., and Herron N. Organic small molecule materials for organic light-emitting diodes. Opt Sci Eng 111 (2007) 295-412
6. D'Andrade B. White phosphorescent LEDs offer efficient answer. Nat Photonics 1 (2007) 33-34
7. Su Y.J., Huang H.L., Li C.L., Chien C.H., Tao Y.T., Chou P.T., et al. Highly efficient red electrophosphorescent devices based on iridium isoquinoline complexes: remarkable external quantum efficiency over a wide range of current. Adv Mater 15 (2003) 884-888
8. Wen S.W., Lee M.T., and Chen C.H. Recent development of blue fluorescent OLED materials and devices. J Disp Technol 1 (2005) 90-99
9. Park J.H., Seo J.H., Lim S.H., Ryu G.Y., Shin D.M., and Kim K. The effect of the molecular structure of organic material on the properties of solid-state fluorescence and electroluminescence. J Phys Chem Solids 69 (2008) 1314-1319
10. Chen C.T. Evolution of red organic light-emitting diodes: materials and devices. Chem Mater 16 (2004) 4389-4400
11. Lee Y.G., Kang S.K., Oh T.S., Lee H.N., Lee S., and Koh K.H. Comparison of two cohost systems for doped red organic light-emitting devices in an effort to improve the efficiency and the lifetime. Org Electron 9 (2008) 339-346
12. Zhao Y.X., Peng P., Zhou Y.H., Wu W.C., and Tian W.J. Energy transfer and luminescent properties in PVK and novel donor-acceptor molecular materials blend system. Chem J Chin Univ 28 (2007) 1345-1349
13. Wang B.C., Liao H.R., Chen W.H., Chou Y.M., Yeh J.T., and Chang J.C. Theoretical investigation of electro-luminescent properties in red emission DCM, DCJ, RED and DAD derivatives. J Mol Struct Theochem 716 (2005) 19-25
14. Zhang X.H., Chen B.J., Lin X.Q., Wong O.Y., Lee C.S., Kwong H.L., et al. A new family of red dopants based on chromene-containing compounds for organic electroluminescent devices. Chem Mater 13 (2001) 1565-1569
15. Li J.Y., Liu D., Hong Z.R., Tong S.W., Wang P.F., Ma C.W., et al. A new family of isophorone-based dopants for red organic electroluminescent devices. Chem Mater 15 (2003) 1486-1490
16. Yang L., Guan M., Nie D., Lou B., Liu Z., Bian Z., et al. Efficient, saturated red electroluminescent devices with modified pyran-containing emitters. Opt Mater 29 (2007) 1672-1679
17. Xin H., Li F.Y., Shi M., Bian Z.Q., and Huang C.H. Efficient, saturated red electroluminescent devices with modified pyran-containing emitters. J Am Chem Soc 125 (2003) 7166-7167
18. Kido J., and Okamoto Y. Organo lanthanide metal complexes for electroluminescent materials. Chem Rev 102 (2002) 2357-2368
19. Li S.F., Zhong G.Y., Zhu W.H., Li F.Y., Pan J.F., Huang W., et al. White light electroluminescence from a dendritic europimn complex. Chem Lett 34 (2005) 688-689
20. O'Brien D.F., Baldo M.A., Thompson M.E., and Forrest S.R. Improved energy transfer in electrophosphorescent devices. Appl Phys Lett 74 (1999) 442-444
21. Baldo M.A., O'Brien D.F., You Y., Shoustikov A., Sibley S., Thompson M.E., et al. Highly efficient phosphorescent emission from organic electroluminescent devices. Nature 395 (1998) 151-154
22. Kim D.U., Paik S.H., Kim S.H., Tak Y.H., Kim S.D., Han Y.S., et al. Electroluminescent characteristics of novel platinum-porphyrin complex. Colloids Surf A 313 (2008) 444-447
23. Yao Y.S., Zhou Q.X., Wang X.S., Wang Y., and Zhang B.W. A DCM-type red-fluorescent dopant for high-performance organic electroluminescent devices. Adv Funct Mater 17 (2007) 93-100
24. Liu T.H., Iou C.Y., and Chen C.H. Doped red organic electroluminescent devices based on a cohost emitter system. Appl Phys Lett 83 (2003) 5241-5243
25. Chen C.H., Tang C.W., Shi J., and Klubek K.P. Recent developments in the synthesis of red dopants for Alq(3) hosted electroluminescence. Thin Solid Films 363 (2000) 327-331
26. Balaganesan B., Wen S.W., and Chen C.H. Synthetic study of tetramethyljulolidine-a key intermediate toward the synthesis of the red dopant DCJTB for OLED applications. Tetrahedron Lett 44 (2003) 145-147
27. Chen CH, Klubek KP, Shi JM. Red organic electroluminescent materials. U.S. Patent. No. 5908581; 1999.
28. Miles M.L., Harris T.M., and Hauser C.R. Aroylations at the methyl group of benzoylacetone and related β-Diketones with esters to form 1,3,5-triketones by sodium hydride. Other terminal condensations. J Org Chem 30 (1965) 1007-1011
29. Horiuchi T., Miura H., and Uchida S. Highly-efficient metal-free organic dyes for dye-sensitized solar cells. Chem Commun 24 (2003) 3036-3037
30. Horiuchi T., Miura H., and Uchida S. J Photochem Photobiol A 164 1-3 (2004) 29-32
31. Liu Y.L., Di C.A., Xin Y.R., Yu G., Liu Y.Q., He Q.G., et al. Organic light-emitting diode based on a carbazole compound. Synth Met 156 (2006) 824-827
32. Cervini R., Li X.C., Spencer G.W.C., Holmes A.B., Moratti S.C., and Friend R.H. Electrochemical and optical studies of PPV derivatives and poly(aromatic oxadiazoles). Synth Met 84 (1997) 359-360
33. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 03, revision D.01 (2004), Gaussian, Inc., Wallingford, CT
34. Becke A.D. Density-functional thermochemistry.III. The role of exact exchange. J Chem Phys 98 (1993) 5648-5652
35. Ditchfield R., Hehre W.J., and Pople J.A. Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules. J Chem Phys 54 (1971) 724-728
36. Dreuw A., and Head-Gordon M. Failure of time-dependent density functional theory for long-range charge-transfer excited states: the zincbacteriochlorin-bacterlochlorin and bacteriochlorophyll-spheroidene complexes. J Am Chem Soc 126 (2004) 4007-4016
37. Tang C.W., VanSlyke S.A., and Chen C.H. Electroluminescence of doped organic thin-films. J Appl Phys 65 (1989) 3610-3616
38. Hamada Y., Kanno H., Tsujioka T., Takahashi H., and Usuki T. Red organic light-emitting diodes using an emitting assist dopant. Appl Phys Lett 75 (1999) 1682-1684