10.1002/chem.202003571
Chemistry - A European Journal
FULL PAPER
Lee, R. Zaen, K.-M. Park, K. H. Lee, J. Y. Lee, Y. Kang, Organometallics
2018, 37, 4639-4647.
CE of 46.6 cd.A-1, PE of 32.6 lm.W-1 and ext of 14%. Promising
results
could
also
be
obtained
with
and
(bis-
(bis-
[9]
a) H. Rudmann, S. Shimada, M. F. Rubner, J. Am. Chem. Soc. 2002,
124, 4918-4921; b) S. Welter, K. Brunner, J. W. Hofstraat, L. De Cola,
Nature 2003, 421, 54-57; c) Y.-L. Tung, P.-C. Wu, C.-S. Liu, Y. Chi, J.-K.
Yu, Y.-H. Hu, P.-T. Chou, S.-M. Peng, G.-H. Lee, Y. Tao, A. J. Carty, C.-
F. Shu, F.-L. Wu, Organometallics 2004, 23, 3745-3748; d) P.-T. Chou,
Y. Chi, Chem. Soc. Rev. 2007, 36, 1421-1431; e) B.-S. Du, J.-J. Liao,
M.-H. Huang, C.-H. Lin, H.-W. Lin, Y. Chi, H.-A. Pan, G.-L Fan, K.-T.
Wong, G.-H. Lee, P.-T. Chou, Adv. Funct. Mater. 2012, 22, 3491-3499.
f) W.-K. Chu, S.-M. Yiu, C.-C. Ko, Organometallics 2014, 33, 6771-6777.
carbazole)aminophenylalkynyl
(5)
carbazole)aminopyridinealkynyl (7) as ancillary ligands, with ext
of 9.82 and 9.51% respectively. Moreover, we also presented the
first example of an efficient green device based on a binuclear
gold(III) complex. The described performances confirm the
promising potential of the 3-(N^C^C) template to develop a new
class of efficient light emitting materials.
[10] J. K. Borchardt, Mater. Today 2004, 7, 42-46.
[11] Y. Cao, I. D. Parker, G. Yu, C. Zhang, A. J. Heeger, Nature 1999, 397,
414-417.
Experimental Section
[12] A. Vogler, H. Kunkely, Coord. Chem. Rev. 2001, 219-221, 489-507; b) V.
W.-W. Yam, E. C.-C. Cheng, Chem. Soc. Rev. 2008, 37, 1806-1813; c)
R. Kumar, C. Nevado, Angew. Chem. Int. Ed. 2017, 56, 1994-2015; d)
C.-H. Lee, M.-C. Tang, Y.-C. Wong, M.-Y. Chan, V. W. W. Yam, J. Am.
Chem. Soc. 2017,139, 10539-10550; e) M.-C. Tang, C.-H. Lee, M. Ng,
Y.-C. Wong, V. W.-W. Yam, Angew. Chem. Int. Ed. 2018, 57, 5463-5466.
[13] a) P.-K. Chow, C. Ma, W.-P. To, G. S. Ming Tong, S.-L. Lai, S. C. F. Kui,
W.-M. Kwok, C.-M. Che, Angew. Chem. Int. Ed. 2013, 52, 11775-11779.
b) P.-K. Chow, G. Cheng, G.G. S. Ming Tong, C. Ma, W.-M. Kwok, W.-
H. Ang, C. Y.-S. Chung, C. Yang, F. Wang, C.-M. Che, Chem. Sci. 2016,
7, 6083-6098.
The following information can be found in the Supporting
Information of this manuscript: synthetic routes and
characterization of complexes 1-16. Photophysical properties.
Cyclic voltammetry. Materials used in the preparation of OLED.
OLED device fabrication and characterization. DFT calculations.
Acknowledgements
[14] (a) M. Hashimoto, S. Igawa, M. Yashima, I. Kawata, M. Hoshino, M.
Osawa, J. Am. Chem. Soc. 2011, 133, 10348-10351. b) R. Hamze, L. L.
Peltier, D. Sylvinson, M. Jung, J. Cardenas, R. Haiges, M. Soleilhavoup,
R. Jazzar, P. I. Djurovich, G. Bertrand, M. E. Thompson, Science 2019,
363, 601-606.
CN thank the European Research Council (ERC Starting grant
agreement no. 307948) and the Swiss National Science
Foundation (SNF) (200020-146853), for financial support. CJS is
grateful for the financial support from SNF (200021-178944) and
ETH Zurich.
[15]
a) W. J. Wolf, M.S. Winston, F. D. Toste, Nature Chem. 2014, 6, 159-
164. b) J. Gil-Rubio, J. Vicente, Dalton Trans. 2015, 44, 19432-19442. c)
H. Kawai, W. J. Wolf, A. G. DiPasquale, M. S. Winston, F. D. Toste, J.
Am. Chem. Soc. 2016, 138, 587-593
Keywords: gold(III) • 3-(N^C^C) • OLED • emitter •
phosphorescent
[16] a) V. W.-W. Yam, K. M.-C. Wong, L.-L. Hung, N. Zhu, Angew. Chem. Int.
Ed. 2005, 44, 3107-3110; b) W.-P. To, G. S.-M. Tong, W. Lu, C. Ma, J.
Liu, A. L.-F. Chow, C.-M. Che, Angew. Chem. Int. Ed. 2012, 51, 2654-
2657; c) W.-P. To, D. Zhou, G. S. M. Tong, G. Cheng, C. Yang, C.-M.
Che, Angew. Chem. Int. Ed. 2017, 56, 14036-14041.
[1]
[2]
[3]
M. Pope, H. P. Kallmann, J. Chem. Phys. 1963, 38, 2042-2043.
C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913.
P. K. Bhatnagar, Khan Z. (eds) Nanomaterials and Their Applications.
Advanced Structured Materials 2018, 84, 261-287.
[17] a) V. K.-M. Au, K. M.-C. Wong, D. P.-K. Tsang, M.-Y. Chang, N. Zhu, V.
W.-W. Yam, J. Am. Chem. Soc. 2010, 132, 14273-14278; b) M.-C. Tang,
D. P.-K. Tsang, M. M.-Y. Chen, K. M.-C. Wong, V. W.-W. Yam, Angew.
Chem. Int. Ed. 2013, 52, 446-449; c) W.-P. To, K. T. Chan, G. S. M. Tong,
C. Ma, W.-M. Kwok, X. Guan, K.-H. Low, C.-M. Che, Angew. Chem. Int.
Ed. 2013, 52, 6648-6652; d) M.-C. Tang, C. K.-M. Chan, D. P.-K. Tsang,
Y.-C. Wong, M. M.-Y. Chan, K. M.-C. Wong, V. W.-W. Yam, Chem. Eur.
J. 2014, 20, 15233-15241; e) M.-C. Tang, D. P.-K. Tsang, Y.-C. Wong,
M.-Y. Chan, K. M.-C. Wong, V. W.-W. Yam, J. Am. Chem. Soc. 2014,
136, 17861-17868; f) G. Cheng, K. T. Chan, W.-P. To, C.-M. Che, Adv.
Mater. 2014, 26, 2540-2546; g) M.-C. Tang, C.-H. Lee, S.-L. Lai, M. Ng,
M.-Y. Chan, V. W.-W Yam, J. Am. Chem. Soc. 2017, 139, 9341-9349; h)
C.-H. Lee, M.-C. Tang, W.-L. Cheung, S.-L. Lai, M.-Y. Chan, V. W.-W.
Yam, Chem. Sci. 2018, 9, 6228-6232.
[4]
[5]
M. A. Baldo, M. E. Thompson, S. R. Forrest, Nature 2000, 403, 750-753.
M. Kleinschmidt, C. van Wüllen, C. M. Marian, J. Chem. Phys. 2015, 142,
094301.
[6]
[7]
a) M. A. Baldo, D. F. O’Brien, M. E. Thompson, S. R. Forrest, Phys. Rev.
B. 1999, 60, 14422-14428; b) H. Yersin, A. F. Rausch, R. Czerwieniec,
T. Hofbeck, T. Fischer, Coord. Chem. Rev. 2011, 255, 2622-2652
a) C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, J. Appl. Phys.
2001, 90, 5048-5051; b) S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-
Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E.
Thompson, J. Am. Chem. Soc. 2001, 123, 4304-4312; c) B. W.
D’Andrade, M. E. Thompson, S. R. Forrest, Adv. Mater. 2002, 14, 147-
151; d) X. Ren, J. Li, R. J. Holmes, P. I. Djurovich, S. R. Forrest, M. E.
Thompson, Chem. Mater. 2004, 16, 4743-4747; d) Y. Kawamura, K.
Goushi, J. Brooks, J. J. Brown, H. Sasabe, C. Adachi, Appl. Phys. Lett.
2005, 86, 071104; f) H. J. Bolink, E. Coronado, S. G. Santamaria, M.
Sessolo, N. Evans, C. Klein, E. Baranoff, K. Kalyanasundaram, M.
Graetzel, M. K. Nazeeruddin, Chem. Commun. 2007, 3276-3278; g) H.
Fu, Y.-M. Cheng, P.-T. Chou, Y. Chi, Mater. Today 2011, 14, 472-479;
h) P.-N. Lai, C. H. Brysacz, M. K. Alam, N. A. Ayoub, T. G. Gray, J. Bao,
T. S. Teets, J. Am. Chem. Soc. 2018, 140, 10198-10207.
[18] a) R. Kumar, A. Linden, C. Nevado, Angew. Chem. Int. Ed. 2015, 54,
14287-14290; b) R. Kumar, A. Linden, C. Nevado J. Am. Chem. Soc.
2016, 138, 13790; c) R. Kumar, J.-P. Krieger, E. Gómez-Bengoa, T. Fox,
A. Linden, C. Nevado, Angew. Chem. Int. Ed. 2017, 56, 12862-12865; d)
H. Beucher, E. Merino, A. Genoux, T. Fox, C. Nevado, Angew. Chem.
Int. Ed. 2019, 58, 9064-9067.
[19] L.-K. Li, M.-C. Tang, S.-L. Lai, M. Ng, W.-K. Kwok, M.-Y. Chan, V. W.-W.
Yam, Nature Photon. 2019, 13, 185-191.
[8]
a) M. A. Baldo, D. F. O’Brien, Y. You, A. Shoustikov, S. Sibley, M. E.
Thompson, S. R. Forrest, Nature 1998, 395, 151-154; b) M. Hissler, J. E.
McGarrah, W. B. Connick, D. K. Geiger, S. D. Cummings, R. Eisenberg,
Coord. Chem. Rev. 2000, 208, 115-137; c) D. R. McMillin, J. J. Moore,
Coord. Chem. Rev. 2002, 229, 113-121; d) W. Lu, B.-X. Mi, M. C. Chan,
Z. Hui, C.-M. Che, N. Zhu, S.-T. Lee, J. Am. Chem. Soc. 2004, 126, 4958-
4971; e) F. N. Castellano, I. E. Pomestchenko, E. Shikhova, F. Hua, M.
L. Muro, N. Rajapakse, Coord. Chem. Rev. 2006, 250, 1819-1828; f) C.
[20] W.-K. Kwok, M.-C. Tang, S.-L. Lai, W.-L. Cheung, L.-K. Li, M. Ng, M.-Y.
Chan, V. W.-W. Yam, Angew. Chem. Int. Ed. 2020, 59,
10.1002/anie.202001972.
[21] H. Beucher, S. Kumar, E. Merino, W.-H. Hu, G. Stemmler, S. Cuesta-
Galisteo, J. A. González, J. Jagielski, C.-J. Shih, C. Nevado, Chem.
Mater. 2020, 32, 1605-1611.
[22] W.-Y. Wong, C.-L. Ho, Coord. Chem. Rev. 2009, 253, 1709-1758.
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