Glass-forming organic semiconductors for optoelectronics

Medziagotyra

Volumn 17, Issue 4, 2011, Pages 335-342

  Tomkevičiene, Aušra ^a   Gražulevičius, Juozas Vidas ^a  

^a KAUNAS UNIVERSITY OF TECHNOLOGY   (Lithuania)

Author keywords

Charge transporting; Molecular glasses; Polymers

Indexed keywords

EID: 84869219753     PISSN: 13921320     EISSN: None     Source Type: Journal    
DOI: 10.5755/j01.ms.17.4.767     Document Type: Article

References (82)

1. Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Marks, R. N., Taliani, C., Bradley, D. D. C., Dos Santos, D. A., Bredas, J. L., Logdlund, M., Salaneck, W. R. Electroluminescence in Conjugated Polymers Nature 397 1999: pp. 121-128.
2. Pron, A., Gawrys, P., Zagorska, M., Djuradoa, D., Demadrillea, R. Electroactive Materials for Organic Electronics: Preparation Strategies, Structural Aspects and Characterization Techniques Chemical Society Reviews 39 2010: pp. 2577-2632.
3. Shirota, Y., Kageyama, H. Charge Carrier Transporting Molecular Materials and Their Applications in Devices Chemical Reviews 107 2007: pp. 953-1010.
4. Shirota, Y. Organic Materials for Electronic and Optoelectronic Devices Journal of Material Chemistry 14 2000: pp. 1-25.
5. Grazulevicius, J. V., Strohriegl, P., Pielichowski, J., Pielichowski, K. Carbazole-containing Polymers: Synthesis, Properties and Applications Progress in Polymer Science 28 2003: pp. 1297-1353. http://dx.doi.org/10.1016/S0079-6700(03)00036-4
6. Boudreault, P. L. T., Najari, A., Leclerc, M. Processable Low-bandgap Polymers for Photovoltaic Applications. Chemistry of Materials 23 2011: pp. 456-469.
7. Jung, B. J., Tremblay, N. J., Yeh, M. L., Katz, H. E. Molecular Design and Synthetic Approaches to Electron-transporting Organic Transistor Semiconductors. Chemistry of Materials 23 2011: pp. 568-582.
8. Facchetti, A. π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications. Chemistry of Materials 23 2011: pp. 733-758.
9. Simokaitiene, J., Sakalyte, A., Grigoriev, T. E., Makhaeva, E. E., Grazulevicius, J. V. Electrochromic Properties of 1,3-di(2-[10-{4-methoxyphenyl}phenothiazin-3-yl]vinyl)benzene Materials Science (Medziagotyra) 15 2009: pp. 236-239.
10. Ashraf, R. S., Chen, Z., Leem, D. S., Bronstein, H., Zhang, W., Schroeder, B., Geerts, Y., Smith, J., Watkins, S., Anthopoulos, T. D., Sirringhaus, H., Mello, J. C., Heeney, M., McCulloch, I. Silaindacenodithiophene Semiconducting Polymers for Efficient Solar Cells and High-mobility Ambipolar Transistors. Chemistry of Materials 23 2011: pp. 768-770.
11. Burroughes, J. H., Bradley, D. D. C, Brown, A. R., Marks, R. N., Mackay, K., Friend, R. H., Burns, P. L., Holmes, A. B. Light-emitting-diodes Based on Conjugated Polymers Nature 347 1990: pp. 539-541.
12. Tang, C. W., VanSlyke, S. A. Organic Electroluminescent Diodes. Applied Physics Letters 51 1987: pp. 913-915. http://dx.doi.org/10.1063/1.98799
13. Chen, C. H., Shi, J, Tang, C. W. Recent Developments in Molecular Organic Electroluminescent Materials Macromolecular Symposia 125 1998: pp. 1-48.
14. Strohriegl, P., Grazulevicius, J. V. Charge-transporting Molecular Glasses Advanced Materials 14 2002: pp. 1439-1452. http://dx.doi.org/10.1002/1521-4095(20021016)14:201439::AID-ADMA14393.0.CO;2-H
15. Borsenberger, P. M., Weiss, D. S. Organic Photoreceptors for Imaging Systems. New York: Marcel Dekker, 1993.
16. Oyston, S., Wang, C., Hughes, G., Batsanov, A. S., Perepichka, I. F., Bryce, M. R., Ahn, J. H., Pearson, C., Petty, M. C. New 2,5-diaryl-1,3,4-oxadiazole-fluorene Hybrids as Electron Transporting Materials for Blended-layer Organic Light Emitting Diodes Journal of Materials Chemistry 15 2005: pp. 194-203.
17. Jandke, M., Strohriegl, P., Berleb, S., Werner, E., Brutting, W. Phenylquinoxaline Polymers and Low-molar-mass Glasses as Electron-transpoting Materials in Organic Light-emitting Diodes Macromolecules 31 1998: pp. 6434-6443.
18. Brabec, C. J., Saritciftci, N. S., Recent Developments in Conjugated Polymer Based Plastic Solar Cells. Monatshefte für Chemie 132 2001: pp. 421-432.
19. Brabec, C. J., Saritciftci, N. S., Hummelen, J. C., Plastic Solar Cells Advanced Functional Materials 11 2001: pp. 15-26. http://dx.doi.org/10.1002/1616-3028(200102)11:115::AID-ADFM153.0.CO;2-A
20. Bach, U., Lupo, D., Comte, P., Moser, J. E., Weissörtel, F., Salbeck, J., Spreitzer, H., Grätzel, M., Solid-State Dye-Sensitized Mesoporous Tio2 Solar Cells With High Photon-To-Electron Conversion Efficiencies. Nature 395 1998: pp. 583-585.
21. Nazeeruddin, M. K., Kay, A., Rodicio, I., Humphry-Baker, R., Muller, E., Liska, P., Vlacopoulos, N., Gratzel, M. Conversion of Light to Electricity by cis-X2Bis(2,2'-bipyridyl-4,4'-dicarboxylate)ruthenium(II) Charge-transfer sensitizers (X=Cl, Br, CN, SCN) on Nanocrystalline TiO2 Electrodes. Journal of American Chemical Society 115 1993: pp. 6382-6390. http://dx.doi.org/10.1021/ja00067a063
22. Bach, U., Lupo, D., Comte, P., Moser, J. E., Weissortel, F., Salbeck, J., Spreitzer, H., Gratzel, M. Solid-state Dye-sensitized Mesoporous TiO2 Solar Cells with High Photon-to-electron Conversion Efficiencies. Nature 395 1998: pp. 583-585.
23. Hagen, G., Haarer, D., Schaffrath, W., Otschik, P., Fink, R., Bacher, A., Schmidt, H. W., Novel Hybrid Solar Cell Consisting of Inorganic Nanoparticles and an Organic Hole Transport Material. Synthetic Metals 89 1997: pp. 215-220.
24. Chabinyc, M. L., Salleo, A. Materials Requirements And Fabrication Of Active Matrix Arrays Of Organic Thin-Film Transistors For Displays. Chemistry of Materials 16 2004: pp. 4509-4521. http://dx.doi.org/10.1021/cm049647z
25. Tsumura, A., Koezuka, H., Ando, T. Macromolecular Electronic Device: Field-effect Transistor with a Polythiophene Thin Film. Applied Physics Letters 49 1986: pp. 1210-1213.
26. Madru, R., Guillaud, G., Al Sadoun, M., Maitrot, M., Andre, J.-J., Simon, J., Even, R. A Well-Behaved Field Effect Transistor Based On An Intrinsic Molecular Semiconductor Chemistry Physics Letters 145 1988: pp. 343-346. http://dx.doi.org/10.1016/0009-2614(88)80018-6
27. Horowitz, G., Garnier, F., Yassar, A., Hajlaoui, R., Kouki, F. Field-effect Transistor Made with a Sexithiophene Single Crystal Advanced Materials 8 1996: pp. 52-54.
28. Torsi, L., Dodabalapur, A., Rothberg, L. J., Fung, A. W. P., Katz, H. E., Intrinsic Transport Properties and Performance Limits of Organic Field-effect Transistors. Science 272 1996: pp. 1462-1464. http://dx.doi.org/10.1021/cm048532s
29. Yasuda, T., Fujita, K., Tsutsui, T., Geng, Y., Culligan, S. W., Chen, S. H., Carrier Transport Properties of Monodisperse Glassy-Nematic Oligofluorenes in Organic Field-Effect Transistors. Chemistry of Materials 17 2005: pp. 264-268.
30. Jarrett, C. P., Pichler, K., Newbould, R., Friend, R. H. Transport Studies in C-60 and C-60/C-70 Thin Films Using Metal-insulator-semiconductor Field-effect Transistors. Synthetic Metals 77 1996: pp. 35-38. http://dx.doi.org/10.1016/0379-6779(96)80052-X
31. Tapponnier, A., Biaggio, I., Gunter, P. Ultrapure C-60 Field-effect Transistors and the Effects of Oxygen Exposure. Applied Physics Letters 86 2005: pp. 112114-112117.
32. Ogawa, K., Kato, T., Ikegami, A., Tsuji, H., Aoki, N., Ochiai, Y., Bird, J. Electrical Properties of Field-effect Transistors Based on C60 Nanowhiskers. Applied Physics Letters 88 2006: pp. 112109-112112. http://dx.doi.org/10.1063/1.2186519
33. Meskinis, S., Gudaitis, R., Slapikas, K., Tamulevicius, S., Gudonyte, A., Grazulevicius, J. V., Lygaitis, R., Burbulis E., Michaleviciute, A., Getautis, V., Malinauskas, T. Electrical Characteristics of the Organic Field Effect Transistors Based on New Organic Semiconducting Compounds Materials Science (Medziagotyra) 13 2007: pp. 97-102.
34. Meskinis, S., Slapikas, K., Gudaitis, R. Tamulevicius, S., Iljinas, A., Gudonyte, A., Grazulevicius, J. V., Getautis, V., Michaleviciute, A., Malinauskas, T., Lygaitis, R. Investigation of the Electrical Characteristics of the Metal/Organic Semiconductor/Metal Structures with Top Contact Configuration Materials Science (Medziagotyra) 16 2010: pp. 195-201.
35. Strohriegl, P., Grazulevicius, J. V. Charge-transporting Molecular Glasses Advanced Materials 14 2002: pp. 1439-1452. http://dx.doi.org/10.1002/1521-4095(20021016)14:201439::AID-ADMA14393.0.CO;2-H
36. Grigalevicius, S., Getautis, V., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V., Montrimas, E. Hole-transporting Molecular Glasses Based on Carbazole and Diphenylamine Moieties Materials Chemistry and Physics 72 2001: pp. 395-400.
37. Grigalevicius, S., Buika, G., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V., Montrimas, E. 3,6-di(diphenylamino)-9-alkylcarbazoles: Novel Hole-transporting Molecular Glasses. Synthetic Metals 122 2001: pp. 311-314. http://dx.doi.org/10.1016/S0379-6779(00)00344-1
38. Matoliukstyte, A., Grazulevicius, J. V., Reina, J. A., Jankauskas, V., Montrimas, E. Synthesis and Properties of Glass-forming Condensed Aromatic Amines with Reactive Functional Groups. Materials Chemistry and Physics 98 2006: pp. 324-329.
39. Tsai, M.-H., Hong, Y.-H., Chang, C.-H., Su, H.-C., Wu, C.-C., Matoliukstyte, A., Simokaitiene, J., Grigalevicius, S., Grazulevicius, J. V., Hsu, C.-P., 3-(9-carbazolyl)carbazoles and 3,6-di(9-carbazolyl) Carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence. Advanced Materials 19 2007: pp. 862-866.
40. Grigalevicius, S., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V. Synthesis and Properties of poly(3,9-carbazole) and Low-molar-mass Glass-forming Carbazole Compounds. Polymer 43 2002: pp. 2603-2608.
41. Blazys, G., Grigalevicius, S., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V., Kampars, V. Phenothiazinyl-containing Aromatic Amines as Novel Amorphous Molecular Materials for Optoelectronics. Journal of Photochemistry and Photobiology A: Chemistry 174 2005: pp. 1-6.
42. Tomkeviciene, A., Grazulevicius, J. V., Jankauskas, V. High Hole Mobilities in the Amorphous Films of 2,7-di(9-carbazolyl)-9-(2-ethylhexyl)carbazole. Chemistry Letters 37 2008: pp. 344-345. http://dx.doi.org/10.1246/cl.2008.344
43. Tomkeviciene, A., Grazulevicius, J. V., Kazlauskas, K., Gruodis, A., Jursenas, S., Ke, T.-H., Wu, C.-C. Impact of Linking Topology on the Properties of Carbazole Trimers and Dimers Journal of Physical Chemistry C (accepted).
44. Kirkus, M., Simokaitiene, J., Grigalevicius J. V., Jankauskas, V. Phenyl-, carbazolyl-and fluorenyl-substituted Derivatives of indolo[3,2-b]carbazole as Hole-transporting Glass Forming Materials. Synthetic Metals 160 2010: pp. 750-755.
45. Lengvinaite, S., Grazulevicius, J. V., Grigalevicius, S., Gu, R., Dehaen, W., Jankauskas, V., Zhang, B., Xie, Z. Indolo[3,2-b]carbazole-based Functional Derivatives as Materials for Light Emitting Diodes. Dyes and Pigments 85 2010: pp. 183-188.
46. Vaitkeviciene, V., Grazulevicius, J. V., Peciuraite, V., Grigalevicius, S., Jankauskas, V. Triazine-based Aromatic Amines as New Glass-forming Charge Transport Materials Molecular Crystals Liquid Crystals 468 2007: pp. 141[493]-150[502].
47. Kirkus, M., Lygaitis, R., Tsai, M.-H., Grazulevicius, J. V., Wu, C.-C. Triindolylmethane-based High Triplet Energy Glass-forming Electroactive Molecular Materials. Synthetic Metals 158 2008: pp. 226-232. http://dx.doi.org/10.1016/j.synthmet.2008.01.006
48. Kirkus, M., Tsai, M.-H., Grazulevicius, J. V., Wu, C.-C., Chi, L.-C., Wong, K.-T. New indole-carbazole Hybrids as Glass-forming High-triplet-energy Materials. Synthetic Metals 159 2009: pp. 729-734.
49. Peciuraite, V., Vaitkeviciene, V., Grigalevicius, S., Grazulevicius, J. V., Jankauskas, V. Di(9-alkylcarbazol-3-yl)arylamines as Electroactive Amorphous Materials for Optoelectronics Monatshefte fur Chemie 137 2006: pp. 1053-1062.
50. Padmaperuma, A. B., Sapochak, L. S., Burrows, P. E., New Charge Transporting Host Material for Short Wavelength Organic Electrophosphorescence: 2,7-bis(diphenylphosphine oxide)-9,9-dimethylfluorene. Chemistry of Materials 18 2006: pp. 2389-2396. http://dx.doi.org/10.1021/cm0600677
51. Lygaitis, R., Getautis, V., Grazulevicius, J. V., Hole-transporting Hydrazones. Chemical Society Reviews 37 2008: pp. 770-788. http://dx.doi.org/10.1039/b702406c
52. Ostrauskaite, J., Voska, V., Antulis, J., Gaidelis, V., Jankauskas, V., Grazulevicius, J. V., High Hole Mobilities in Carbazole-based Glass-forming Hydrazones. Journal of Materials Chemistry 12 2002: pp. 3469-3474.
53. Matoliukstyte, A., Lygaitis, R., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V., Montrimas, E., Tokarski, Z., Jubran, N. 9-(4-Methoxy)carbazolyl-containing Hydrazones for Optoelectronic Applications. Molecular Crystals Liquid Crystals 427 2005: pp. 107[419]-116[428].
54. Lygaitis, R., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V., Sidaravicius, J., Tokarski, Z., Jubran, N. Hole-transporting Glass-forming 3,3'-dicarbazyl-based hydrazones. Molecular Crystals Liquid Crystals 427 2005: pp. [407]-[418].
55. Matoliukstyte, A., Grazulevicius, J. V., Jankauskas, V. Glass-forming Hole-transporting Triphenylamine-based Hydrazones with Reactive Functional Groups Molecular Crystals Liquid Crystals 466 2007: pp. 85-100.
56. Lygaitis, R., Keruckas, J., Grigoriev, T. E., Makhaeva, E. E., Grazulevicius, J. V. Electrochromic Properties of 4-ethylenedioxythiophene-2-carbaldehyde N,N-diphenylhydrazone Materials Science (Medžiagotyra) 15 2009: pp. 240-242.
57. Michaleviciute, A., Lygaitis, R., Grazulevicius, J. V., Buika, G., Jankauskas, V., Undzenas, A., Fataraite, E. Thiophene-based Hydrazones as Hole-transporting Materials. Synthetic Metals 159 2009: pp. 223-227.
58. Aich, R., Tran-Van, F., Goubard, F., Beouch, L., Michaleviciute, A., Grazulevicius, J. V., Ratier, B., Chevrot, C. Hydrazone Based Molecular Glasses for Solid-state Dye-sensitized Solar Cells Thin Solid Films 516 2008: pp. 7260-7265.
59. Michaleviciute, A., Ostrauskaite, J., Buika, G., Grazulevicius, J. V., Jankauskas, V., Tran-Van, F., Chevrot, C. Thiophene-based Glass-forming Hole-transporting Hydrazones Monatshefte fur Chemie 139 2008: pp. 1011-1017. http://dx.doi.org/10.1007/s00706-008-0897-1
60. Jung, B. J., Tremblay, N. J., Yeh, M.-L., Katz, H. E., Molecular Design and Synthetic Approaches to Electron-transporting Organic Transistor Semiconductors. Chemistry of Materials 23 2011: pp. 568-582.
61. Sivamurugan, V., Lygaitis, R., Grazulevicius, J. V., Gaidelis, V., Jankauskas, V., Valiyaveettil S., Effect of Substituents on the Electron Transport Properties of Bay Substituted Perylene Diimide Derivatives. Journal of Materials Chemistry 19 2009: pp. 4268-4275.
62. Sivamurugan, V., Kazlauskas, K., Jursenas, S., Gruodis, A., Simokaitiene, J., Grazulevicius, J.V., Valiyaveettil, S., Synthesis and Photophysical Properties of Glass-forming Bay Substituted Perylenediimide Derivatives. Journal of Physical Chemistry B 114 2010: pp. 1782-1789.
63. Grazulevicius, J. V., Kublickas, R. Polymerizaation of Carbazolyl-containing Epoxides by Activated Monomer Mechanism. European Polymer Journal 27 1991: pp. 1411-1416.
64. Grobelny, Z., Stolarzewicz, A., Morejko-Buz, B., Buika, G., Grazulevicius, J. V., Maercker, A. Study on the Initiation Step of 2-(9-carbazolyl)ethyl Glycidyl Ether Polymerization by K-, K+ (15-crown-5)(2) European Polymer Journal 38 2002: pp. 2359-2363. http://dx.doi.org/10.1016/S0014-3057(02)00142-8
65. Lengvinaite, S., Grazulevicius, J. V., Grigalevicius, S., Zhang, B., Xie, Z., Jankauskas, V. Electro-active Monomers and Polymers Containing 3-arylcarbazol-9-yl Fragments. Synthetic Metals 160 2010: pp. 1962-1967. http://dx.doi.org/10.1016/j.synthmet.2010.07.016
66. Lengvinaite, S., Grazulevicius, J. V., Grigalevicius, S., Lai, Y. M., Wang, W. B., Jou, J. H. Polyethers Containing 2-phenylindol-1-yl Moieties as Host Materials for Light Emitting Diodes. Synthetic Metals 160 2010: pp. 1793-1796.
67. Tomkeviciene, A., Bartiuk, T., Grazulevicius, J. V., Jankauskas, V. Monomers and Polymers with the Pendent Adducts of Carbazole with 5H-dibenz(b,f)azepine and Its 10,11-dihydro Derivative Reactive Functional Polymer (Submitted).
68. Getautis, V., Grazulevicius, J. V., Daskeviciene, M., Malinauskas, T., Jankunaite, D., Gaidelis, V., Jankauskas, V., Sidaravicius, J., Tokarski, Z. Novel Hydrazone Based Polymers as Holetransporting Materials Polymer 46 2005: pp. 7918-7922.
69. Getautis, V., Grazulevicius, J. V., Daskeviciene, M., Malinauskas, T., Gaidelis, V., Jankauskas, V., Tokarski, Z. Novel Hydrazone Moieties Containing Polymers for Optoelectronics. Journal of Photochemistry and Photobiology A: Chemistry 180 2006: pp. 23-27.
70. Ohmori, Y., Uchida, A., Muro, K., Yoshino, K. Blue Electroluminescent Diodes Utilizing Poly(alkylfluorene). Japanese Journal of Applied Physics 30 1991: pp. L1941-L1943. http://dx.doi.org/10.1143/JJAP.30.L1941
71. Janietz, S., Bradley, D. D. C., Grell, M., Giebeler, C., Inbasekaran, M., Woo, E. P. Electrochemical Determination of the Ionization Potential and Electron Affinity of Poly(9,9'-octylfluorene). Applied Physics Letters 73 1998: pp. 2453-2455. http://dx.doi.org/10.1063/1.122479
72. Grell, M., Bradley, D. D. C., Inbasekaran, M., Woo, E. P. A Glass-forming Conjugated Main-chain Liquid Crystal Polymer for Polarized Electroluminescence Applications. Advanced Materials 9 1997: pp. 798-802.
73. Redecker, M., Bradley, D. D. C., Inbasekaran, M., Woo E. P. Nondispersive Hole Transport in an Electroluminescent Polyfluorene. Applied Physics Letters 73 1998: pp. 1565-1567.
74. Romero, D. B., Schaer, M., Leclerc, M., Ades, D., Siove, A., Zuppiroli, L. The Role of Carbazole in Organic Light-emitting Devices. Synthetic Metals 80 1996: pp. 271-277.
75. Morin, J. F., Leclerc, M. Syntheses of Conjugated Polymers Derived from N-alkyl-2,7-carbazoles. Macromolecules 34 2001: pp. 4680-4682. http://dx.doi.org/10.1021/ma010152u
76. Morin, J. F., Beaupre, S., Leclerc, M., Levesque, I., D'Iorio, M. Blue Light-Emitting Devices From New Conjugated Poly(N-Substituted-2,7-Carbazole) Derivatives. Applied Physics Letters 80 2002: pp. 341-343.
77. Iraqi, A., Wataru, I. Preparation And Properties Of 2,7-Linked N-Alkyl-9H-Carbazole Main-Chain Polymers. Chemistry of Materials 16 2004: pp. 442-448. http://dx.doi.org/10.1021/cm031078s
78. Fichou, D. Handbook of Oligo-and Polythiophenes. Wiley-VCH: Weinheim, 1999.
79. Binh, N. T., Minh, L. Q., Bassler, H. Photoconduction in Poly(3-alkylthiophene). 2. Charge Transport. Synthetic Metals 58 1993: pp. 39-50. http://dx.doi.org/10.1016/0379-6779(93)91116-J
80. Yoshino, K., Yin, X. H., Morita, S., Kawai, T., Zakhidov, A. A. Enhaanced Photoconductivity of C-60 Doped Poly(3-alkylthiophene) Solid State Communications 85 1993: pp. 85-88. http://dx.doi.org/10.1016/0038-1098(93)90352-N
81. Zaumseil, J., Sirringhaus, H. Electron And Ambipolar Transport In Organic Field-Effect Transistors. Chemical Reviews 107 2007: pp. 1296-1323. http://dx.doi.org/10.1021/cr0501543
82. Li, G., Shrotriya, V., Huang, J., Yao, Y., Moriarty, T., Emery, K., Yang, Y. High-Efficiency Solution Processable Polymer Photovoltaic Cells by Self-Organization of Polymer Blends. Nature Materials 4 2005: pp. 864-868.