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Y.-W. Zhong, J. M. Moran-Mirabal, H. G. Graighead,
~
H. D. Abruna, J. A. Marohn and G. G. Malliaras, Nat. Mater.,
2007, 6, 894.
6 P. Matyba, K. Maturova, M. Kemerink, N. D. Robinson and
L. Edman, Nat. Mater., 2009, 8, 672.
7 T. K. Hatwar, M. E. Kondakova, D. J. Giesen and J. P. Spindler,
OLED Materials and Device Architectures for Full-Color Displays
and Solid-State Lighting in Organic Electronics: Materials,
Processing, Devices and Applications, ed. F. So, CRC Press, Boca
Raton, FL, USA, 2009, pp. 433–509.
0.73 mmol) in CH2Cl2–CH3OH (40/5 mL) gave 504 mg (0.48
mmol, 65%) of the product after chromatography (silica, 20 g),
anion exchange (CH3OH, 10 mL; KPF6, 3.7 g, 20 mmol, in 50
mL of water), and re-crystallization (15 mL of CH2Cl2–200 mL
of ether). It is important not to use an excess of ligand imp in the
reaction, because imp co-elutes with 1 during chromatography,
and it can be removed only by repeated re-crystallization from
CH2Cl2–ether.
Electroluminescence devices
ꢀ
8 D. Tordera, S. Meier, M. Lenes, R. D. Costa, E. Ortı, W. Sarfert and
H. J. Bolink, Adv. Mater., 2012, 24, 897.
The solvents were supplied by Aldrich. The thickness of films was
determined with an Ambios XP-1 profilometer. Indium tin oxide
ITO-coated glass plates (15 Uꢀ1) were patterned by conventional
photolithography (Naranjo Substrates). The substrates were
cleaned by sonication in water–soap, water, and 2-propanol
baths, in that order. After drying, the substrates were placed in a
UV-ozone cleaner (Jelight 42-220) for 20 min.
9 H.-C. Su, H.-F. Chen, F.-C. Fang, C.-C. Liu, C.-C. Wu, K.-T. Wong,
Y.-H. Liu and S.-M. Peng, J. Am. Chem. Soc., 2008, 130, 3413.
10 A. B. Tamayo, S. Garon, T. Sajoto, P. I. Djurovich, I. M. Tsyba,
R. Bau and M. E. Thompson, Inorg. Chem., 2005, 44, 8723.
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Lett., 2006, 89, 261118; (b) H. J. Bolink, E. Coronado, R. D. Costa,
ꢀ
ꢀ
N. Lardies and E. Ortı, Inorg. Chem., 2008, 47, 9149.
12 (a) H.-C. Su, F.-C. Fang, T.-Y. Hwu, H.-H. Hsieh, H.-F. Chen,
G.-H. Lee, S.-M. Peng, K.-T. Wong and C.-C. Wu, Adv. Funct.
Mater., 2007, 17, 1019; (b) C. Rothe, C.-J. Chiang, V. Jankus,
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A. P. Monkman, Adv. Funct. Mater., 2009, 19, 2038; (c)
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The electroluminescence devices were made as follows. First, a
90 nm layer of PEDOT:PSS (CLEVIOSꢀ P VP AI 4083,
aqueous dispersion, 1.3–1.7% solid content, Heraeus) was spin-
coated on the ITO glass substrate to improve the reproducibility
of the devices and to prevent the formation of pinholes. Then, a
100/150/190 nm transparent film of 1 and the ionic liquid 1-butyl-
3-methylimidazolium hexafluorophosphate (>98.5%, Sigma-
Aldrich) in a 4 to 1 molar ratio were spin-coated from 20 mg
mLꢀ1 (1) acetonitrile solution at 1000 rpm for 20 s. The device
was transferred into an inert atmosphere glovebox (<0.1 ppm O2
and H2O, M. Braun) and dried on a hot plate at 100 ꢁC for 1 h.
The Al electrode (70 nm) was thermally vapor-deposited using a
shadow mask under a vacuum (<1 ꢂ 10ꢀ6 mbar) with an
Edwards Auto500 evaporator integrated in the glovebox. The
area of the device was 6.5 mm2. The devices were not encapsu-
lated and were characterized inside the glovebox at room
temperature. The device lifetime was measured by applying
pulsed currents and monitoring the voltage and luminance by a
True Colour Sensor MAZeT (MTCSiCT Sensor) with a Botest
OLT OLED Lifetime-Test System.
ꢀ
13 H. J. Bolink, E. Coronado, R. D. Costa, E. Ortı, M. Sessolo,
S. Graber, K. Doyle, M. Neuburger, C. E. Housecroft and
E. C. Constable, Adv. Mater., 2008, 20, 3910.
ꢀ
14 R. D. Costa, E. Ortı, H. J. Bolink, S. Graber, C. E. Housecroft and
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15 L. He, L. Duan, J. Qiao, D. Zhang, L. Wang and Y. Qiu, Chem.
Commun., 2011, 47, 6467.
16 J. D. Slinker, J. Rivnay, J. A. DeFranco, D. A. Bernards,
A. A. Gorodetsky, S. T. Parker, M. P. Cox, R. Rohl,
~
G. G. Malliaras, S. Flores-Torres and H. D. Abruna, J. Appl.
Phys., 2006, 99, 074502.
17 S. Bernhard, J. A. Barron, P. L. Houston, H. D. Abruna,
~
J. L. Ruglovksy, X. Gao and G. G. Malliaras, J. Am. Chem. Soc.,
2002, 124, 13624.
18 (a) Y. Tao, C. Yang and J. Qin, Chem. Soc. Rev., 2011, 40, 2943; (b)
L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong and J. Kido, Adv.
Mater., 2011, 23, 926; (c) A. Chaskar, H.-F. Chen and K.-T. Wong,
Adv. Mater., 2011, 23, 3876.
19 E. A. Steck and A. R. Day, J. Am. Chem. Soc., 1943, 65, 452.
20 (a) S. Rosepriya, A. Thiruvalluvar, J. Jayabharathi, M. Venkatesh
Perumal, R. J. Butcher, J. P. Jasinski and J. A. Golen, Acta
Crystallogr., 2011, E67, o989; (b) S. Rosepriya, M. Venkatesh
Perumal, A. Thiruvalluvar, J. Jayabharathi, R. J. Butcher,
J. P. Jasinski and J. A. Golen, Acta Crystallogr., 2011, E67, o1965.
21 N. M. Shavaleev, H. Adams and J. A. Weinstein, Inorg. Chim. Acta,
2007, 360, 700.
Acknowledgements
This work is supported by the European Union (CELLO, STRP
of Economy and Competitiveness (MINECO) (MAT2011-
24594, CSD2007-00010 and CTQ2009-08790). D.T. and A.P.
acknowledge MECD (Spanish Ministry of Education, Culture
and Sport) and MINECO for FPU and FPI grants, respectively.
22 Q. Zhao, S. Liu, M. Shi, F. Li, H. Jing, T. Yi and C. Huang,
Organometallics, 2007, 26, 5922.
ꢀ
23 (a) F. Zapata, A. Caballero, A. Espinosa, A. Tarraga and P. Molina,
Dalton Trans., 2009, 3900; (b) S. Ramachandra, F. Polo, F. Edafe,
K. C. Schuermann, C. A. Nijhuis, P. Belser, W. F. Reus,
G. M. Whitesides and L. De Cola, Pure Appl. Chem., 2011, 83, 779;
(c) J. Sun, W. Wu, H. Guo and J. Zhao, Eur. J. Inorg. Chem., 2011,
3165; (d) G. Nasr, A. Guerlin, F. Dumur, L. Beouch, E. Dumas,
G. Clavier, F. Miomandre, F. Goubard, D. Gigmes, D. Bertin,
G. Wantz and C. R. Mayer, Chem. Commun., 2011, 47, 10698.
24 (a) S. T. Parker, J. D. Slinker, M. S. Lowry, M. P. Cox, S. Bernhard
and G. G. Malliaras, Chem. Mater., 2005, 17, 3187; (b) R. D. Costa,
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19268 | J. Mater. Chem., 2012, 22, 19264–19268
This journal is ª The Royal Society of Chemistry 2012