J. L. Bredas, M. Logdlund and W. R. Salaneck, Nature, 1999, 397,
121–128.
4 U. Mitschke and P. Bauerle, J. Mater. Chem., 2000, 10, 1471–1507.
5 M.-C. Choi, Y. Kim and C.-S. Ha, Prog. Polym. Sci., 2008, 33, 581–
630.
requires: C, 80.5; H, 8.0; N, 4.5%.) GPC assay in THF vs. narrow
polystyrene standards revealed Mw ¼ 4700, Mn ¼ 4000, PDI ¼
1.19; Mw ¼ 1800, Mn ¼ 1700, PDI ¼ 1.04; Mw ¼ 700, Mn ¼ 600,
MP ¼ 1100, PDI ¼ 1.22; lmax/nm (CHCl3 solution) 320; dH (400
MHz, CDCl3) 0.75–0.81 (m, CH2 and CH3), 0.81–1.37 (br m,
CH2), 1.37 (s, CH3), 1.37–1.49 (br m, CH2), 1.62 (br s, CH2),
7.30–7.54 (m, ArH), 7.60–7.72 (br m, ArH), 7.72–8.02 (br m,
ArH), 8.06–8.21 (br m, ArH), 8.31 (br s, ArH), 8.38–8.52 (br m,
ArH); dC (100 MHz, CDCl3) 12.3, 14.1, 22.6, 24.0, 24.9, 29.1,
29.2. 31.8, 33.4, 121.4, 121.6, 124.2, 124.5, 125.6, 125.6, 127.1,
127.3, 129.3, 129.6, 129.8, 130.5, 130.6, 132.0.
6 A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz and
A. B. Holmes, Chem. Rev., 2009, 109, 897–1091.
€
7 K. Mullen and U. Scherf, Organic Light-Emitting Devices: Synthesis,
Properties and Applications, Wiley-VCH, Weinheim, 2006.
8 J. Chen and Y. Cao, Macromol. Rapid Commun., 2007, 28, 1714–1742.
9 W. W. H. Wong, J. F. Hooper and A. B. Holmes, Aust. J. Chem.,
2009, 62, 393–401.
10 P.-L. T. Boudreault, S. Beaupre and M. Leclerc, Polym. Chem., 2010,
1, 127–136.
11 Q. Zhao, S.-J. Liu and W. Huang, Macromol. Chem. Phys., 2009, 210,
1580–1590.
12 A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay and A. Salleo,
Chem. Rev., 2010, 110, 3–24.
13 Y. Yoshiro, Sci. Technol. Adv. Mater., 2009, 10, 024313.
14 I. McCulloch, M. Heeney, M. L. Chabinyc, D. DeLongchamp,
a,u-Diphenylpoly(4-(4-(octyloxy)phenyl)-3,5-bis(m-phenylene)-4H-
1,2,4-triazole-9,9-dioctyl-9H-dibenzosilole-2,7-diyl) (P7). 4-(4-(Octy-
loxy)phenyl)-3,5-bis(3-bromophenyl)-4H-1,2,4-triazole (886 mg,
1.5 mmol) was used as the co-monomer, following general
polymerisation method B, to afford the title compound (1.14 g,
91%) as a light yellow fibrous solid. (Found: C, 80.9; H, 8.5; N,
4.9. A repeat unit composition of C56H69N3OSi requires: C, 81.0;
H, 8.6; N, 5.1%.) GPC assay in THF vs. narrow polystyrene
€
R. J. Kline, M. Colle, W. Duffy, D. Fischer, D. Gundlach,
B. Hamadani, R. Hamilton, L. Richter, A. Salleo, M. Shkunov,
D. Sparrowe, S. Tierney and W. Zhang, Adv. Mater., 2009, 21,
1091–1109.
ꢀ
15 S. Beaupre, P.-L. T. Boudreault and M. Leclerc, Adv. Mater., 2010,
22, E6–E27.
standards revealed Mw ¼ 12 200, Mn ¼ 6700, PDI ¼ 1.82; lmax
/
16 J. C. Sanchez and W. C. Trogler, J. Mater. Chem., 2008, 18, 3143–
3156.
nm (CHCl3 solution) 326; dH (400 MHz, CDCl3) 0.73–0.89 (m,
CH2 and CH3), 1.10–1.39 (br m, CH2), 1.41–1.52 (br m, CH2),
1.79–1.84 (br m, CH2), 3.96–4.09 (br m, CH2), 6.95–7.04 (br m,
ArH), 7.32–7.53 (br m, ArH), 7.64–7.90 (br m, ArH), 7.92 (br s,
ArH); dC (100 MHz, CDCl3) 12.5, 14.3, 22.8, 24.1, 26.3, 29.3,
29.4, 29.6, 32.0, 33.6, 116.0, 121.5, 127.5, 127.6, 128.0, 129.1,
129.2, 131.9, 138.9, 139.2, 141.7, 147.7, 155.0, 160.3.
17 M. Sims, D. D. C. Bradley, M. Ariu, M. Koeberg, A. Asimakis,
M. Grell and D. G. Lidzey, Adv. Funct. Mater., 2004, 14, 765–781.
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19 V. N. Bliznyuk, S. A. Carter, J. C. Scott, G. Klarner, R. D. Miller and
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20 K. L. Chan, M. Sims, S. I. Pascu, M. Ariu, A. B. Holmes and
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21 J. Chen and Y. Cao, Acc. Chem. Res., 2009, 42, 1709–1718.
22 S. Yamaguchi and K. Tamao, J. Chem. Soc., Dalton Trans., 1998,
3693–3702.
a,u-Diphenylpoly(bis(p-phenylene)-4-sec-butylphenylamine-9,9-
dioctyl-9H-dibenzosilole-2,7-diyl) (P8). Bis(4-bromophenyl)-4-
sec-butylphenylamine (697 mg, 1.5 mmol) was used as the
co-monomer, following general polymerisation method B, to
afford the title compound (0.98 g, 92%) as a bright yellow fibrous
solid. GPC assay in THF vs. narrow polystyrene standards
revealed Mw ¼ 11 700, Mn ¼ 5700, PDI ¼ 2.05; lmax/nm (CHCl3
solution) 390; dH (400 MHz, CDCl3) 0.78–0.90 (m, CH2 and
CH3), 0.93–1.03 (br m, CH2), 1.13–1.47 (br m, CH2), 1.54–1.64
(m, CH2), 2.52–2.63 (m, CH), 6.95–7.26 (m, ArH), 7.51–7.68 (m,
ArH), 7.78–7.92 (m, ArH), 8.04 (s, ArH); dC (100 MHz, CDCl3)
1.2, 12.6, 14.3, 22.0, 22.9, 24.2, 25.1, 29.3, 29.5, 31.5, 32.1, 33.6,
41.3, 121.4, 124.0, 125.1, 127.8, 127.9, 128.1, 128.2, 128.7, 131.6,
132.3, 135.3, 138.9, 139.4, 147.1, 147.3.
ꢀ
23 M. Hissler, P. W. Dyer and R. Reau, Coord. Chem. Rev., 2003, 244, 1–
44.
24 K. L. Chan, M. J. McKiernan, C. R. Towns and A. B. Holmes, J. Am.
Chem. Soc., 2005, 127, 7662–7663.
25 P.-L. T. Boudreault, A. Michaud and M. Leclerc, Macromol. Rapid
Commun., 2007, 28, 2176–2179.
26 E. Wang, L. Wang, L. Lan, C. Luo, W. Zhuang, J. Peng and Y. Cao,
Appl. Phys. Lett., 2008, 92, 033303–033307.
27 H. Usta, G. Lu, A. Facchetti and T. J. Marks, J. Am. Chem. Soc.,
2006, 128, 9034–9035.
28 G. Lu, H. Usta, C. Risko, L. Wang, A. Facchetti, M. A. Ratner and
T. J. Marks, J. Am. Chem. Soc., 2008, 130, 7670–7685.
29 J. C. Sanchez, A. G. DiPasquale, A. L. Rheingold and W. C. Trogler,
Chem. Mater., 2007, 19, 6459–6470.
30 J. C. Sanchez, S. A. Urbas, S. J. Toal, A. G. DiPasquale,
A. L. Rheingold and W. C. Trogler, Macromolecules, 2008, 41,
1237–1245.
31 K. L. Chan, S. E. Watkins, C. S. K. Mak, M. J. McKiernan,
C. R. Towns, S. I. Pascu and A. B. Holmes, Chem. Commun., 2005,
5766–5768.
32 Y. Q. Mo, R. Y. Tian, W. Shi and Y. Cao, Chem. Commun., 2005,
4925–4926.
33 E. G. Wang, C. Li, Y. Q. Mo, Y. Zhang, G. Ma, W. Shi, J. B. Peng,
W. Yang and Y. Cao, J. Mater. Chem., 2006, 16, 4133–4140.
34 Y.-Q. Mo, X.-Y. Deng, X. Jiang and Q.-H. Cui, J. Polym. Sci., Part
A: Polym. Chem., 2009, 47, 3286–3295.
Acknowledgements
The authors would like to thank Imperial College London for
provision of a student bursary and a doctoral training award,
Cambridge Display Technology Ltd. for financial support via
a CASE award, Ann Wilson for assistance with material char-
acterisation, and CSIRO for access to their AC-II spectrometer.
35 L. Li, C. Xu and S. Li, Tetrahedron Lett., 2010, 51, 622–
624.
36 C. Duan, W. Cai, F. Huang, J. Zhang, M. Wang, T. Yang, C. Zhong,
X. Gong and Y. Cao, Macromolecules, 2010, 43, 5262–5268.
37 L. Huo, H.-Y. Chen, J. Hou, T. L. Chen and Y. Yang, Chem.
Commun., 2009, 5570–5572.
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