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4.2.3.1. 9,9-Bis[4-(3,6-di-tert-butyl-9-carbazolyl)phe-
References and notes
nyl]fluorene (TBCPF). This compound was synthesized ac-
cording to the general procedure using compound 1 (1.1 g,
2 mmol) and 3,6-di-tert-butylcarbazole (1.4 g, 5 mmol).
1. (a) Baldo, M. A.; O’Brien, D. F.; You, Y.; Shoustikov, A.;
Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395,
151; (b) Baldo, M. A.; Lamansky, S.; Burrows, P. E.;
Thompson, M. E.; Forrest, S. R. Appl. Phys. Lett. 1999, 75, 4.
2. (a) Adachi, C.; Kwong, R. C.; Djurovich, P.; Adamovich, V.;
Baldo, M. A.; Thompson, M. E.; Forrest, S. R. Appl. Phys.
Lett. 2001, 79, 2082; (b) Holmes, R. J.; Forrest, S. R.; Tung,
Y.-J.; Kwong, R. C.; Brown, J. J.; Garon, S.; Thompson,
M. E. Appl. Phys. Lett. 2003, 82, 2422; (c) Baldo, M. A.;
Forrest, S. R. Phys. Rev. B 2000, 62, 10958.
3. (a) Adachi, C.; Baldo, M. A.; Forrest, S. R.; Thompson, M. E.
J. Appl. Phys. 2001, 90, 5048; (b) Ikai, M.; Tokito, S.;
Sakamoto, Y.; Suzuki, T.; Taga, Y. Appl. Phys. Lett. 2001, 79,
156; (c) Duan, J.-P.; Sun, P.-P.; Cheng, C.-H. Adv. Mater.
2002, 15, 224; (d) Tung, Y.-L.; Lee, S.-W.; Chi, Y.; Tao,
Y.-T.; Chien, C.-H.; Cheng, Y.-M.; Chou, P.-T.; Peng, S.-M.;
Liu, C.-S. J. Mater. Chem. 2005, 15, 460.
1
Yield: 65%. H NMR (CDCl3): d 8.12 (d, J¼1.4 Hz, 4H),
7.86 (d, J¼7.2 Hz, 2H), 7.60 (d, J¼7.60 Hz, 2H), 7.48–
7.35 (m, 20H), 1.45 (s, 36H). MALDI-TOF MS: m/z 872.9
(M+). Anal. Calcd for C65C64N2: C, 89.87; H, 6.49; N,
3.50. Found: C, 89.96; H, 6.36; N, 3.68.
4.2.3.2.
9,9-Bis[4-(9-carbazolyl)phenyl]-2,7-di-tert-
butylfluorene (CPTBF). This compound was synthesized
according to the general procedure using compound 2
(1.4 g, 2 mmol) and carbazole (0.8 g, 5 mmol). Yield:
1
80%. H NMR (CDCl3): d 8.13 (d, J¼7.5 Hz, 4H), 7.74
(d, J¼7.9 Hz, 2H), 7.60 (d, J¼1.4 Hz, 2H), 7.55–7.36
(m, 18H), 7.30–7.24 (m, 4H), 1.37 (s, 18H). MALDI-TOF
MS: m/z 760.6 (M+). Anal. Calcd for C57C48N2: C, 89.40;
H, 7.39; N, 3.21. Found: C, 89.35; H, 7.37; N, 3.12.
4. (a) Adamovich, V.; Brooks, J.; Tamayo, A.; Alexander, A. M.;
Djurovich, P.; D’Andrade, B. W.; Adachi, C.; Forrest, S. R.;
Thompson, M. E. New J. Chem. 2002, 25, 1171; (b) Tokito,
S.; Iijima, T.; Suzuri, Y.; Kita, H.; Tsuzuki, T.; Sato, F. Appl.
Phys. Lett. 2003, 83, 569; (c) Lei, G. T.; Wang, L. D.; Duan,
L.; Wang, J. H.; Qiu, Y. Synth. Met. 2004, 144, 249.
5. (a) Holmes, R. J.; D’Andrade, B. W.; Forrest, S. R.; Ren, X.; Li,
J.; Thompson, M. E. Appl. Phys. Lett. 2003, 83, 3818; (b) Ren,
X. F.; Li, J.; Holmes, R. J.; Djurovich, P. I.; Forrest, S. R.;
Thompson, M. E. Chem. Mater. 2004, 16, 4743.
6. Qiao, J.; Wang, L. D.; Qiu, Y. Proc. SPIE 2006, 6192, 61920T.
7. (a) Yeh, S.-J.; Wu, M.-F.; Chen, C.-T.; Song, Y.-H.; Chi, Y.;
Ho, M.-H.; Hsu, S.-F.; Chen, C. H. Adv. Mater. 2005, 17,
285; (b) Tsai, M.-H.; Lin, H.-W.; Su, H.-C.; Ke, T.-H.; Wu,
C.-C.; Fang, F.-C.; Liao, Y.-L.; Wong, K.-T.; Wu, C.-I. Adv.
Mater. 2006, 18, 1216; (c) Shih, P.-I.; Chiang, C.-L.; Dixit,
A. K.; Chen, C.-K.; Yuan, M.-C.; Lee, R.-Y.; Chen, C.-T.;
Diau, E. W.-G.; Shu, C.-F. Org. Lett. 2006, 8, 2799; (d)
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. Adv. Mater. 2007, 19, 862;
(e) Shih, P.-I.; Chien, C.-H.; Chuang, C.-Y.; Shu, C.-F.;
Yang, C.-H.; Chen, J.-H.; Chi, Y. J. Mater. Chem. 2007, 17,
1692.
8. (a) Xie, H. Z.; Liu, M. W.; Wang, O. Y.; Zhang, X. H.; Lee,
C. S.; Hung, L. S.; Lee, S. T.; Teng, P. F.; Kwong, H. L.;
Zheng, H.; Che, C. M. Adv. Mater. 2001, 13, 1245; (b) Chew,
S.; Lee, C. S.; Lee, S.-T.; He, J.; Li, W.; Pan, J.; Zhang, X.;
Kwong, H. Appl. Phys. Lett. 2006, 88, 093510.
9. (a) Chen, Y.-C.; Huang, G.-S.; Hsiao, C.-C.; Chen, S.-A.
J. Am. Chem. Soc. 2006, 128, 8549; (b) Chen, X.; Tseng,
H.-E.; Liao, J.-L.; Chen, S.-A. J. Phys. Chem. B 2005, 109,
17496; (c) Li, J. Y.; Ziegler, A.; Wegner, G. Chem.—Eur. J.
2005, 11, 4450.
4.3. X-ray crystallography
Single crystal samples of CPF and TBCPF suitable for X-ray
crystallography were obtained via gradient-temperature sub-
limation. The room temperature (294ꢃ1 K) single-crystal
X-ray experiments were performed on a Bruker SMART
APEX CCD diffractometer equipped with graphite mono-
chromatized Mo Ka radiation. Direct phase determination
yielded the positions of all non-hydrogen atoms. Hydrogen
atoms were generated theoretically and rode on their parent
atoms in the final refinement. All non-hydrogen atoms were
subjected to anisotropic refinement. Crystallographic data
(excluding structure factors) for the structures in this paper
have been deposited with the Cambridge Crystallographic
Data Centre as supplementary publication nos. CCDC-
291117 and CCDC-647969. Copies of the data can be
obtained, free of charge, on application to CCDC, 12 Union
Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033
4.4. Fabrication and characterization of OLEDs
The OLED devices were fabricated on sufficiently cleaned
glass substrates precoated with indium tin oxide (ITO).
Organic layers were sequentially deposited by thermal
evaporation from quartz boats in a high vacuum chamber un-
der the base pressure of around 5ꢁ10ꢂ4 Pa. Then a Mg/Ag
(atomic ratio 10:1) layer followed by a Ag cap was evapo-
rated to form the cathode. The luminance–current–voltage
(J–V–B) characteristics were determined with a Keithley
4200 semiconductor characterization system. The EL
spectra were collected on a Photo Research PR650 spectro-
photometer. All the measurements were carried out in air at
room temperature without further encapsulation.
10. Sapochak, L. S.; Padmaperuma, A.; Washton, N.; Endrino, F.;
Schmett, G. T.; Marshall, J.; Fogarty, D.; Burrows, P. E.;
Forrest, S. R. J. Am. Chem. Soc. 2001, 123, 6300.
Acknowledgements
11. Shen, W.-J.; Dodda, R.; Wu, C.-C.; Wu, F.-I.; Liu, T.-H.;
Chen, H.-H.;Chen,C.H.;Shu, C.-F. Chem. Mater. 2004, 16, 930.
12. Kalonowski, J.; Giro, G.; Cocci, M.; Fattori, V.; Marco, P. D.
Appl. Phys. Lett. 2000, 76, 2352.
13. Gange, R. R.; Koval, C. A.; Lisensky, G. C. Inorg. Chem. 1980,
19, 2854.
This work was supported by the National Natural Science
Foundation of China (Nos. 50325310 and 50403001) and
the National Basic Research Program of China (Grant no.
2006CB806200).