Silole derivatives as efficient electron transporting materials

Journal of the American Chemical Society

Volumn 118, Issue 47, 1996, Pages 11974-11975

  Tamao, Kohei ^a   Uchida, Manabu ^b   Izumizawa, Takenori ^b   Furukawa, Kenji ^b   Yamaguchi, Shigehiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b CHISSO CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; MOLECULAR DYNAMICS; THERMODYNAMICS;

EID: 0029903406     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962829c     Document Type: Article

References (34)

1. Tang. C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913. Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610.
2. Tang. C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913. Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610.
3. Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 57, 531.
4. (a) Strukelj, M.; Papadimitrakopoulos, F.; Miller, T. M.; Rothberg. L. J. Science 1995, 267, 1969.
5. (b) Strukelj, M.; Miller, T. M.: Papadimitrakopoulos, F.; Son, S. J. Am. Chem. Soc. 1995, 117, 11976.
6. It has recently been pointed out, however, that there seems to be no direct correlations between the reduction potentials of the ET materials and the performance of the devices. See ref 3.
7. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
8. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
9. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
10. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
11. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
12. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
13. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
14. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
15. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
16. Representative efficient ET materials reported so far and their pertinent references: 1,3,4-Oxadiazole: (a) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1989, 55, 1489. (b) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56, 799. (c) Hamada, Y.; Adachi. C.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys. 1992, 31, 1812. (d) Pei, Q.; Yang, Y. Adv. Mater. 1995, 7, 559. (e) Li; X.-C; Cacialli, F.; Giles, M.; Grüner, J.; Friend, R. H.; Holmes. A. B.; Moratti, S. C.; Yong, T. M. Adv. Mater. 1995, 7, 898. (f) Li, X.-C.; Holmes, A. B.; Kraft, A.; Moratti, S. C.; Spencer, B. C. W.; Cacialli, F.; Grüner, J.; Friend, R. H. J. Chem. Soc., Chem. Commun. 1995, 2211. (g) Berggren, M.; Granström, M.; Inganäs, O.; Andersson, M. Adv. Mater. 1995, 7, 900. (h) Kido, J.; Harada, G.; Nagai, K. Chem. Lett. 1996, 161. See also refs 2 and 3. 1,2,4-Triazole: (i) Kido, J. Ohtani, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J. Appl. Phys. 1993, 32, L917. (j) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267, 1332.
17. Tris(8-quinolinolato)aluminum(III) Alq and its derivatives: Hamada, Y. Sano, T.; Fujita, M.; Fujii, T.; Nishio, Y.; Shibata, K. Chem. Lett. 1993, 905. See also ref 1.
18. Cyano-substituted poly(p-phenylenevinylene): a) Greenham, N. C. Moratti, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628. b) Moratti, S. C.; Cervini, R.; Holmes, A. B.; Baigent, D. R.; Friend, R. H.; Greenham, H. C.; Grüner, J.; Hamer. P. J. Synth. Metal 1995, 71, 2117.
19. Cyano-substituted poly(p-phenylenevinylene): a) Greenham, N. C. Moratti, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628. b) Moratti, S. C.; Cervini, R.; Holmes, A. B.; Baigent, D. R.; Friend, R. H.; Greenham, H. C.; Grüner, J.; Hamer. P. J. Synth. Metal 1995, 71, 2117.
20. Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215.
21. Silole-containing π-conjugated compounds: (a) Tamao, K.; Yamaguchi, S.; Shiozaki, M.; Nakagawa, Y.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 5867. (b) Tamao, K.; Yamaguchi, S.; Ito, Y.; Matsuzaki, Y.; Yamabe, T.; Fukushima, M.; Mon, S. Macromolecules 1995, 28, 8668. (c) Tamao, K.; Ohno. S.; Yamaguchi, S. J. Chem. Soc., Chem. Commun. 1996, 1873.
22. Silole-containing π-conjugated compounds: (a) Tamao, K.; Yamaguchi, S.; Shiozaki, M.; Nakagawa, Y.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 5867. (b) Tamao, K.; Yamaguchi, S.; Ito, Y.; Matsuzaki, Y.; Yamabe, T.; Fukushima, M.; Mon, S. Macromolecules 1995, 28, 8668. (c) Tamao, K.; Ohno. S.; Yamaguchi, S. J. Chem. Soc., Chem. Commun. 1996, 1873.
23. Silole-containing π-conjugated compounds: (a) Tamao, K.; Yamaguchi, S.; Shiozaki, M.; Nakagawa, Y.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 5867. (b) Tamao, K.; Yamaguchi, S.; Ito, Y.; Matsuzaki, Y.; Yamabe, T.; Fukushima, M.; Mon, S. Macromolecules 1995, 28, 8668. (c) Tamao, K.; Ohno. S.; Yamaguchi, S. J. Chem. Soc., Chem. Commun. 1996, 1873.
24. (a) Janzen, E. G.; Pickett, J. B.; Atwell, W. H. J. Organomet. Chem. 1967, 10, 6.
25. (b) O'Brien, D. H.; Breeden, D. L. J. Am. Chem. Soc. 1981, 103, 3237.
26. Khabashesku, V. N.; Balaji, V.; Boganov, S. E.; Nefedov, O. M.; Michl, J. J. Am. Chem. Soc. 1994, 116, 320.
27. (a) Tamao, K.; Yamaguchi, S. Pure Appl. Chem. 1996, 68, 139.
28. (b) Yamaguchi, S.; Tamao, K. Bull. Chem. Soc. Jpn. 1996, 69, 2327.
29. Ab initio calculations were carried out by using the Gaussian 92 program at the RHF/6-31G* level of theory, in which geometries of those compounds were fully optimized.
30. Strukelj, M.; Jordan, R. H.; Dodabalapur, A. J. Am. Chem. Soc. 1996, 118, 1213.
31. The sily1 groups are introduced to improve the quality of the TST thin film. For the preparation of SiTSTSi, see the supporting information.
32. Tamao, K.; Yamaguchi, S.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 11715.
33. Negishi, E.; Luo, F. T.; Frisbee, R.; Matsushita, H. Heterocyles 1982, 18, 117. Minato, A.; Suzuki, K.; Tamao, K. Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511.
34. Negishi, E.; Luo, F. T.; Frisbee, R.; Matsushita, H. Heterocyles 1982, 18, 117. Minato, A.; Suzuki, K.; Tamao, K. Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 511.