Supplementary Material
Material degradation of liquid organic semiconductors analyzed
by nuclear magnetic resonance spectroscopy
Tatsuya Fukushima,1 Junichi Yamamoto,1 Masashi Fukuchi,1 Shuzo Hirata,2 Heo Hyo Jung,2
Osamu Hirata,3 Yuki Shibano,3 Chihaya Adachi,2 and Hironori Kaji1 a)
1
Institute for Chemical Research, Kyoto University
Uji, Kyoto 611-0011, Japan
2
Center for Organic Photonics and Electronics Research (OPERA), Kyusyu University
744 Motooka, Nishi, Fukuoka 819-0395, Japan
3
Nissan Chemical Industries, LTD
722-1 Tsuboi, Funabashi 274-8507, Japan
a)
Electronic mail: kaji@scl.kyoto-u.ac.jp
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FIG. S1.
1
H NMR spectrum of TEGCz with 0.25 wt% TMP-TFSI in CD2Cl2 solution at
278.2 K. Chemical structure and assignments of TEGCz are also shown.
2
FIG. S2. COSY spectrum of TEGCz in CD2Cl2 solution at 278.2 K. The red square region is
expanded in Figure S3 and S4.
3
FIG. S3.
Expanded COSY spectrum of TEGCz in CD2Cl2 solution at 278.2 K. The
distinction of M1 and M2 is based on effects of an electronegative atom (nitrogen) on the
carbazole moiety. The distinction of M1/M2 and M3/M4 is based on J-coupling (doublet vs
triplet).
4
FIG. S4. Expanded COSY spectrum of TEGCz in CD2Cl2 solution at 278.2 K.
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FIG. S5. 1H NMR spectrum of (TEGCz)2 with 0.25 wt% TMP-TFSI in CDCl3 solution at
298.2 K. Chemical structure and assignments of (TEGCz)2 are also shown.
6
FIG. S6.
COSY spectrum of (TEGCz)2 in CDCl3 solution at 298.2 K. The red square region
is expanded in Figure S7 and S8.
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FIG. S7. Expanded COSY spectrum of (TEGCz)2 in CDCl3 solution at 298.2 K.
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FIG. S8. Expanded COSY spectrum of (TEGCz)2 in CDCl3 solution at 298.2 K.
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FIG. S9. 1H NMR spectra of TEGCz with 0.25 wt% TMP-TFSI; a) before, after driving for
b) 11 s, c) 30 s, and d) 50 s. 1H NMR spectrum of (TEGCz)2 with 0.25 wt% TMP-TFSI before
driving is also shown in e) for comparison.
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FIG. S10. 1H NMR expanded spectra of TEGCz with 0.25 wt% TMP-TFSI; a) before, after
driving for b) 11 s, c) 30 s, and d) 50 s. 1H NMR spectrum of (TEGCz)2 with 0.25 wt% TMPTFSI before driving is also shown in e) for comparison. * marks in the figure represent carbon
satellites for the peaks of TEGCz at 4.51 and 3.85 ppm. The resonance lines at 4.56 and 3.90
ppm, which were not observed in Figure S10a (before driving), were clearly found in all of
Figure S10b–d (after driving). The newly appeared peaks in the device after driving in Figure
S10b–d at 4.56 and 3.90 ppm agree well with the resonance lines of (TEGCz)2 in Figure 10e.
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FIG. S11. 1H NMR expanded spectra of TEGCz with 0.25 wt% TMP-TFSI; a) before, after
driving for b) 11 s, c) 30 s, and d) 50 s. 1H NMR spectrum of (TEGCz)2 with 0.25 wt% TMPTFSI before driving is also shown in e) for comparison.
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