Synthesis and electroluminescence properties of carbazole-containing 2,6-naphthalene-based conjugated polymers

European Polymer Journal

Volumn 45, Issue 4, 2009, Pages 1149-1157

  Mori, Takeshi ^a   Kijima, Masashi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Carbazole; Conjugated polymer; Electroluminescence; Polynaphthalene

Indexed keywords

COPOLYMERIZATION; COPOLYMERS; ELECTROLUMINESCENCE; LIGHT EMISSION; NAPHTHALENE; ORGANIC POLYMERS; PALLADIUM; POLYCONDENSATION; POLYDISPERSITY; POLYMERS; SYNTHESIS (CHEMICAL);

ALTERNATING COPOLYMERS; BASED CONJUGATED POLYMERS; BLUE PHOTOLUMINESCENCES; CARBAZOLE; CARBAZOLYL; ELECTROLUMINESCENCE PROPERTIES; FILM STATE; FLUORESCENCE QUANTUM EFFICIENCIES; HOMOPOLYMER; MAXIMUM EFFICIENCIES; NUMBER AVERAGES; PLED DEVICES; POLYDISPERSITY INDEXES; POLYNAPHTHALENE; RANDOM COPOLYMERS; SIDE CHAINS; SUZUKI COUPLING REACTIONS; YAMAMOTO POLYCONDENSATION;

CONJUGATED POLYMERS;

EID: 61349193209     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2008.12.042     Document Type: Article

References (36)

1. Gningue-Sall D., Kone A., Aaron J.-J., Aeiyach S., Hedayatullah M., and Lacaze P.-C. Poly [(1-methylene-2-methylnaphthalene)-N-pyrrole]: a new fluorophore-containing electroactive conducting polymer 1. Synthetic Met 82 (1996) 119-127
2. Pina F., Lima J.C., Lodeiro C., Seixas de Melo J., Díaz J., Albelda M.T., et al. Long range electron transfer quenching in polyamine chains bearing a terminal naphthalene unit. J Phys Chem A 106 (2002) 8207-8212
3. Montalti M., Dolci L.S., Prodi L., Zaccheroni N., Stuart M.C.A., van Bommel K.J.C., et al. Energy transfer from a fluorescent hydrogel to a hosted fluorophore. Langmuir 22 (2006) 2299-2303
4. Tomasulo M., Kaanumal S.L., Sortino S., and Raymo F.M. Synthesis and properties of benzophenone-spiropyran and naphthalene-spiropyran conjugates. J Org Chem 72 (2007) 595-605
5. Yang H., Yi T., Zhou Z., Zhou Y., Wu J., Xu M., et al. Switchable fluorescent organogels and mesomorphic superstructure based on naphthalene derivatives. Langmuir 23 (2007) 8224-8230
6. Warta W., Stehle R., and Karl N. Ultrapure, high mobility organic photoconductors. Appl Phys A 36 (1985) 163-170
7. Laquindanum J.G., Katz H.E., Dodabalapur A., and Lovinger A.J. N-Channel organic transistor materials based on naphthalene frameworks. J Am Chem Soc 118 (1996) 11331-11332
8. Funahashi M., and Hanna J. Fast ambipolar carrier transport in smectic phases of phenylnaphthalene liquid crystal. Appl Phys Lett 71 (1997) 602-604
9. Oikawa K., Monobe H., Nakayama K., Kimoto T., Tsuchiya K., Heinrich B., et al. High carrier mobility of organic field-effect transistors with a thiophene-naphthalene mesomorphic semiconductor. Adv Mater 19 (2007) 1864-1868
10. Yasuda T., Kashiwagi K., Morizawa Y., and Tsutsui T. Diethynyl naphthalene derivatives with high ionization potentials for p-channel and n-channel organic field-effect transistors. J Phys D Appl Phys 40 (2007) 4471-4475
11. Lee Y.-L., Hsu H.-L., Chen S.-Y., and Yew T.-R. Solution-processed naphthalene diimide derivatives as n-type semiconductor materials. J Phys Chem C 112 (2008) 1694-1699
12. Svoboda J., Novotná V., Kozmík V., Glogarová M., Weissflog W., Diele S., et al. A novel type of banana liquid crystals based on 1-substituted naphthalene-2,7-diol cores. J Mater Chem 13 (2003) 2104-2110
13. Reddy R.A., Baumeister U., Keith C., and Tschierske C. Influence of the core structure on the development of polar order and superstructural chirality in liquid crystalline phases formed by silylated bent-core molecules: naphthalene derivatives. J Mater Chem 17 (2007) 62-75
14. Mori T., and Kijima M. Blue luminescent naphthalene-based liquid crystals. Chem Lett 36 (2007) 710-711
15. Sato M., and Kaeriyama K. Preparation and properties of poly(p-phenylene) and polynaphthylene. Makromol Chem 184 (1983) 2241-2249
16. Habaue S., Seko T., and Okamoto Y. Asymmetric oxidative coupling polymerization of optically active tetrahydroxybinaphthalene derivative. Macromolecules 35 (2002) 2437-2439
17. Habaue S., Seko T., and Okamoto Y. Copper(I)-catalyzed asymmetric oxidative coupling polymerization of 2,3-dihydroxynaphthalene using bisoxazoline ligands. Macromolecules 36 (2003) 2604-2608
18. Hohloch M., Segura J.L., Dötinger S.E., Hohnholz D., Steinhuber E., Spreitzer H., et al. Design, synthesis and study of photoluminescence and electroluminescence of new poly(2,6-naphthylenevinylene) derivatives. Synthetic Met 84 (1997) 319-322
19. Segura J.L., Martin N., and Hanack M. Oligo-2,6-naphthylenevinylenes - new building blocks for the preparation of photoluminescent polymeric materials. Eur J Org Chem 3 (1999) 643-651
20. Martinez-Ruiz P., Behnisch B., Schweikart K.-H., Hanack M., Lüer L., and Oelkrug D. Tuning of photo- and electroluminescence of new soluble, PPV-analogous short-chain compounds with naphthalene moieties. Chem Eur J 6 (2000) 1294-1301
21. Behnisch B., Martinez-Ruiz P., Schweikart K.-H., and Hanack M. Luminescence of new 2,6- and 1,5-naphthalene-based PPV-type trimers and polymers. Eur J Org Chem 14 (2000) 2541-2549
22. Pina J., Seixas de Melo J., Burrows H.D., Galbrecht F., Nehls B.S., Farrell T., et al. Spectral and photophysical studies of poly[2,6-(1,5-dioctylnaphthalene)]thiophenes. J Phys Chem C 111 (2007) 7185-7191
23. Mori T., and Kijima M. Synthesis and optical properties of polynaphthalene derivatives. Opt Mater 30 (2007) 545-552
24. Brown T.M., Kim J.S., Friend R.H., Cacialli F., Daik R., and Feast W.J. Built-in field electroabsorption spectroscopy of polymer light-emitting diodes incorporating a doped poly(3,4-ethylene dioxythiophene) hole injection layer. Appl Phys Lett 75 (1999) 1679-1681
25. Koguchi R., Kobayashi N., Shinnai T., Oikawa K., Tsuchiya K., and Kijima M. Synthesis of poly(N-aryl-2,7-carbazole)s for efficient blue electroluminescence materials. Macromol Chem Phys 209 (2008) 439-449
26. Tyutnev A.P., Saenko V.S., Pozhidaev E.D., and Kolesnikov V.A. Charge carrier transport in polyvinylcarbazole. J Phys Condens Mat 18 (2006) 6365-6377
27. Wheeler A.S., and Ergle D.R. Naphthol studies. I. The bromination of 1,5-dihydroxynaphthalene. J Am Chem Soc 52 (1930) 4872-4880
28. Li X., Wang J., Mason R., Bu X.R., and Harrison J. Combined phase transfer catalysis and ultrasound to enhance tandem alkylation of azo dyes. Tetrahedron 58 (2002) 3747-3753
29. Kijima M., Koguchi R., and Abe S. Blue light emitting poly(N-arylcarbazol-2,7-ylene)s. Chem Lett 34 (2005) 900-901
30. Pommerehne J., Vestweber H., Guss W., Mahrt R.F., Bässler H., Porsch M., et al. Efficient two layer leds on a polymer blend basis. Adv Mater 7 (1995) 551-554
31. Agrawal A.K., and Jenekhe S.A. Electrochemical properties and electronic structures of conjugated polyquinolines and polyanthrazolines. Chem Mater 8 (1996) 579-589
32. Yamamoto T, Ito T, Kubota K. A soluble poly(arylene) with large degree of depolarization. Poly(2,5-pyridinediyl) prepared by dehalogenation polycondensation of 2,5-dibromopyridine with Ni(0)-complexes. Chem Lett 1988;17:153-4.
33. Yamamoto T., Morita A., Maruyama T., Zhou Z.H., Kanbara T., and Sanechika K. New method for the preparation of poly(2,5-thienylene), poly(p-phenylene), and related polymers. Polym J 22 (1990) 187-190
34. Miyaura N., and Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95 (1995) 2457-2483
35. Fu Y., Li Y., Li J., Yan S., and Bo Z. High molecular weight dendronized poly(fluorene)s with peripheral carbazole groups: synthesis, characterization, and properties. Macromolecules 37 (2004) 6395-6400
36. Mori T., and Kijima M. Synthesis and optical properties of blue luminescent poly(2,6-naphthalene)s. J Polym Sci Polym Chem 46 (2008) 4258-4263