The synthesis and characterization of novel dipolar fluorescent materials based on a quinoxaline core

Dyes and Pigments

Volumn 83, Issue 3, 2009, Pages 269-275

  Wang, Haiying ^a   Chen, Gang ^a   Liu, Yu ^a   Hu, Lihua ^a   Xu, Xiaoping ^a   Ji, Shunjun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Bipolar character; Carbazole; Fluorescent; Pendants; Quinoxaline core; Triphenylamine

Indexed keywords

BIPOLAR CHARACTER; CARBAZOLE; FLUORESCENT; PENDANTS; QUINOXALINE CORE; TRIPHENYLAMINE;

LIGHT EMITTING DIODES; ORGANIC LIGHT EMITTING DIODES (OLED); SYNTHESIS (CHEMICAL);

FLUORESCENCE;

CHEMICAL COMPOUND; FLUORESCENCE; INORGANIC COMPOUND; SYNTHESIS;

EID: 67650663150     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.03.007     Document Type: Article

References (42)

1. Mullen K. Organic light emitting devices: synthesis, properties and applications (2006), Wiley-VCH, Weinheim, Germany
2. Tang C.W., and Vanslyke S.A. Organic electroluminescent diodes. Applied Physics Letters 51 12 (1987) 913-915
3. Berresheim A.J., Muller M., and Mullen K. Polyphenylene nanostructures. Chemical Reviews 99 7 (1999) 1747-1785
4. Hide F., Diaz-Garcia M.A., Schartz B.J., and Heeger A.J. New developments in the photonic applications of conjugated polymers. Accounts of Chemical Research 30 (1997) 430-436
5. Kraft A., Grimsdale A.C., and Holms A.B. EL conjugated polymers - seeing polymers in a new light. Angewandte Chemie International Edition 37 4 (1998) 402-428
6. Thomas K.R.J., Lin J.T., Tao Y.T., and Ko C.K. Light-emitting carbazol derivatives: potential electroluminescent materials. Journal of the American Chemical Society 123 38 (2001) 9404-9411
7. Brunner K., Dijken A.V., Börner H., Bastiaansen J.J.A.M., Kiggen N.M.M., and Langeveld B.M.W. Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes: tuning the HOMO level without influencing the triplet energy in small molecules. Journal of the American Chemical Society 126 19 (2004) 6035-6042
8. Zhang Y., Wada T., Wang L., and Sasabe H. Amorphous conjugated carbazole trimers for photorefractive materials. Chemistry of Materials 9 12 (1997) 2798-2804
9. Sonntag M., Kreger K., Hanft D., and Strohriegl P. Novel star-shaped triphenylamine-based molecular glasses and their use in OFETs. Chemistry of Materials 17 11 (2005) 3031-3039
10. Zhang Q., Chen J., and Wang L. Novel hole-transporting materials based on 1,4-bis(carbazolyl)benzene for organic light-emitting devices. Journal of Materials Chemistry 14 (2004) 895-900
11. Ishikawa W., Noguchi K., Kuwabara Y., and Shirota Y. Novel amorphous molecular materials: the starburst molecule 1,3,5-tris[N-(4-diphenyl-aminophenyl)phenylamino]benzene. Advanced Materials 5 7 (1993) 559-561
12. Koene B.E., Loy D.E., and Thompson M.E. Asymmetric triaryldiamines as thermally stable hole transporting layers for organic light-emitting. Chemistry of Materials 10 8 (1998) 2235-2250
13. Loiseau L., Campagna S., Hameurlaine A., and Dehaen W. Dendrimers made of porphyrin cores and carbazole chromophores as peripheral units: absorption spectra, luminescence properties, and oxidation behavior. Journal of the American Chemical Society 127 32 (2005) 11352-11363
14. Roquet S., Cravino A., Leriche P., Alévêque O., Frêre P., and Roncali J. Triphenylamine-thienylenevinylene hybrid systems with internal charge transfer as donor materials for heterojunction solar cells. Journal of the American Chemical Society 128 10 (2006) 3459-3466
15. Leriche P., Frêre P., Cravino A., Alévêque O., and Roncali J. Molecular engineering of the internal charge transfer in thiophene-triphenylamine hybrid π-conjugated systems. The Journal of Organic Chemistry 72 22 (2007) 8332-8336
16. Wei P., Bi X., Wu Z., and Xu Z. Synthesis of triphenylamine-cored dendritic two-photon absorbing chromophores. Organic Letters 7 15 (2005) 3199-3202
17. Yoon K.R., Ko S.O., Lee S.M., and Lee H. Synthesis and characterization of carbazole derived nonlinear optical dyes. Dyes and Pigments 75 (2007) 567-573
18. Bing Y.J., Leung L.M., and Menglian G. Synthesis of efficient blue and red light emitting phenanthroline derivatives containing both hole and electron transporting properties. Tetrahedron Letters 45 (2004) 6361-6363
19. Bacher E., Bayerl M., Rudati P., Reckefuss N., Muller C.D., Meerholz K., et al. Synthesis and characterization of photo-cross-linkable hole-conducting polymers. Macromolecules 38 5 (2005) 1640-1647
20. Wang S., Yu C., Choi M.S., and Kim S.H. A switching fluorescent photochromic carbazole-spironaphthoxazine copolymer. Dyes and Pigments 77 (2008) 245-248
21. Chen L., Cui Y., Mei X., Qian G., and Wang M. Synthesis and characterization of triphenylamino-substituted chromophores for nonlinear optical applications. Dyes and Pigments 72 (2007) 293-298
22. Zhang Q., Ning Z., and Tian H. 'Click' synthesis of starburst triphenylamine as potential emitting material. Dyes and Pigments 81 (2009) 80-84
23. Schmitz C., Pösch P., Thelkkat M., Schmidt H.W., Montali A., Feldman K., et al. Polymeric light-emitting diodes based on poly(p-phenylene ethynylene), poly(triphenyldiamine), and spiroquinoxaline. Advanced Functional Materials 11 1 (2001) 41-46
24. Tomas K.R.T., Lin J.T., Tao Y.T., and Chuen C.H. Quinoxalines incorporating triarylamines: potential electroluminescent materials with tunable emission characteristics. Chemistry of Materials 14 6 (2002) 2796-2802
25. Karastatiris P., Mikroyannidis J.A., and Spiliopoulos L.K. Synthesis, photophysics, and electroluminescence of new quinoxaline-containing poly(p-phenylenevinylene)s. Macromolecules 37 21 (2004) 7867-7878
26. Kulkarni A.P., Zhu Y., and Jenekhe S.A. Quinoxaline-containing polyfluorenes: synthesis, photophysics, and stable blue electroluminescence. Macromolecules 38 5 (2005) 1553-1563
27. Huang T.H., Whang W.T., Shen J.Y., Wen Y.S., Lin J.T., Ke T.H., et al. Dibenzothiophene/oxide and quinoxaline/pyrazine derivatives serving as electron-transport materials. Advanced Functional Materials 16 11 (2006) 1449-1456
28. Feng G.L., Ji S.J., Lai W.Y., and Huang W. Synthesis and optical properties of starburst carbazoles based on 9-phenylcarbazole core. Synlett (2006) 2841-2845
29. Feng G.L., Lai W.Y., Ji S.J., and Huang W. Synthesis of novel star-shaped carbazole-functionalized triazatruxenes. Tetrahedron Letters 47 (2006) 7089-7092
30. Miyaura N., and Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chemical Reviews 95 7 (1995) 2457-2483
31. g hole-transport molecules based on indolo[3,2-b]carbazoles for organic light-emitting devices. Synthetic Metals 111 (2000) 421-424
32. Thomas K.R.J., Lin J.T., Tao Y.T., and Ko C.K. New star-shaped luminescent triarylamines: synthesis, thermal, photophysical, and electroluminescent characteristics. Chemistry of Materials 14 3 (2002) 1354-1361
33. Li Y., Ding J., Day M., Tao Y., Lu J., and D'iorio M. Synthesis and properties of random and alternating fluorene/carbazole copolymers for use in blue light-emitting devices. Chemistry of Materials 16 11 (2004) 2165-2173
34. Zhao Z., Xu X., Jiang Z., Lu P., Yu G., and Liu Y. Oligo(2,7-fluorene ethynylene)s with pyrene moieties: synthesis, characterization, photoluminescene, and electroluminescene. Journal of Organic Chemistry 72 22 (2007) 8345-8353
35. Janietz S., Bradley D.D.C., Grell M., Giebeler C., Inbaselatan M., and Woo E.P. Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene). Applied Physics Letters 73 17 (1998) 2453-2455
36. Pommerehne J., Vestweber H., Guss W., Mahrt R.F., Bässler H., Porsch M., et al. Efficient two layer LEDs on a polymer blend basis. Advanced Materials 7 6 (1995) 551-554
37. Yu G., Yin S., Liu Y., Shuai Z., and Zhu D. Structures, electronic states, and electroluminescent properties of a zinc(II) 2-(2-hydroxyphenyl)benzothiazolate complex. Journal of the American Chemical Society 125 48 (2003) 14816-14824
38. Cui Y., Zhang X., and Jenekhe S.A. Thiophene-linked polyphenylquinoxaline: a new electron transport conjugated polymer for electroluminescent devices. Macromolecules 32 11 (1999) 3824-3826
39. Thelakkat M., and Schmidt H.W. Synthesis and properties of novel derivatives of 1,3,5-tris(diarylamino) benzenes for electroluminescent devices. Advanced Materials 10 3 (1998) 219-223
40. Zhang X.H., Lai W.Y., Gao Z.Q., Wong T.C., Lee C.S., Kwong H.L., et al. Photoluminescence and electroluminescence of pyrazoline monomers and dimmers. Chemical Physics Letters 320 2 (2000) 77-80
41. Tao Y.T., Balasubramaniam E., Danel A., and Tomasik P. Dipyrazolopyridine derivatives as bright blue electroluminescent materials. Applied Physics Letters 77 7 (2000) 933-935
42. Kwong R.C., Lamansky S., and Thompson M.E. Organic light-emitting devices based on phosphorescent hosts and dyes. Advanced Materials 12 15 (2000) 1134-1138