Supporting Information for:
Benzobisthiazole-Fluorene Based Emissive Materials for
Host-Guest Organic Light Emitting Diodes
Jeremy J. Intemann,† Jared F. Mike,† Min Cai, ‡ Charles A. Barnes,† Teng Xiao,‡ Robert A.
Roggers,† Joseph Shinar,‡ Ruth Shinar§ and Malika Jeffries-EL*†
†
Department of Chemistry, Iowa State University, Ames Iowa 50011, United States
‡
Ames Laboratory-USDOE and Department of Physics and Astronomy, Iowa State University,
Ames, Iowa 50011, United States
§
Microelectronics Research Center and Department of Electrical and Computer Engineering,
Iowa State University, Ames Iowa 50011, United States
* malikaj@iastate.edu
Table of Contents
I.
II.
III.
IV.
V.
VI.
VII.
VIII.
IX.
X.
XI.
XII.
XIII.
XIV.
XV.
Figure S1, Differential scanning calorimetry plots………………………...………………….……..…….S2
Figure S2, X-ray defraction plots of polymer films……………………………….....……..…………..….S3
Figure S3, Photoluminescence decay lifetimes plots of polymers…………………………...…...……......S3
Table S1, Photoluminescence decay lifetime data for polymers………………………………….….……S4
Figure S4, 1H NMR spectrum of 2,7-dibromo-9,9-bis(2-(2-ethoxy)ethoxyethylfluorene.…..….…...……S5
Figure S5, 13C NMR spectrum of 2,7-dibromo-9,9-bis(2-(2-ethoxy)ethoxyethylfluorene……….….....…S6
Figure S6, 1H NMR spectrum of 2,7-bis(hydroxymethyl)-9,9-bis(2-(2-ethoxy)ethoxyethyl)fluorene…...S7
Figure S7, 13C NMR spectrum of 2,7-bis(hydroxymethyl)-9,9-bis(2-(2-ethoxy)ethoxyethyl)fluorene......S8
Figure S8, 1H NMR spectrum of 2c……………………………………..…………………..………….….S9
Figure S9, 13C NMR spectrum of 2c………………………………………………………………….......S10
Figure S10, 1H NMR spectrum of P1………………………………………………………………..…....S11
Figure S11, 1H NMR spectrum of P2…………………………………………………………..……...….S12
Figure S12, 1H NMR spectrum of P3…………………………………………………………..…………S13
Figure S13, Cyclic voltammograms of polymer films…………………………………………….……...S14
Figure S14. Current-voltage curves for OLEDs. ……………………………………………………...S14
S1
Figure S1. Differential scanning calorimetry plots of polymers P1, P2, and P3.
S2
Figure S2. X-ray defraction plots for P1 (top), P2 (bottom left), and P3 (bottom right).
Figure S3. Photoluminescence decay lifetime plots for polymers in solution (left) and film
(right).
S3
Table S1. Photoluminescence decay lifetime data for polymers in solution and film.
Solution
Polymer
τ1 (ps), [A1]a
τ1 (ps), [A1]a
τ1 (ps), [A1]a
τ (ps)b
P1
100 [12%]
486 [80%]
967 [8%]
470
P2
110 [13%]
470 [69%]
680 [18%]
460
P3
170 [27%]
700 [67%]
1300 [6%]
600
Thin Film
P1
37 [77%]
220 [18%]
1100 [5%]
120
P2
46 [75%]
280 [19%]
1100 [6%]
150
P3
27 [90%]
280 [7%]
960 [3%]
70
a
A1, A2, and A3 represent the % applitude of the lifetime. bAverage PL decay lifetime
determined by full width at half max.
S4
Figure S4. 1H NMR Spectrum of 2,7-dibromo-9,9-bis(2-(2-ethoxy)ethoxyethyl)fluorene
S5
Figure S5. 13C NMR spectrum of 2,7-dibromo-9,9-bis(2-(2-ethoxy)ethoxyethyl)fluorene.
S6
Figure S6. 1H NMR spectrum of 2,7-bis(hydroxymethyl)-9,9-bis(2-(2ethoxy)ethoxyethyl)fluorene.
S7
13
Figure
S7.
C
NMR
ethoxy)ethoxyethyl)fluorene.
spectrum
S8
of
2,7-bis(hydroxymethyl)-9,9-bis(2-(2-
Figure S8. 1H NMR spectrum of 2c.
S9
Figure S9. 13C NMR spectrum of 2c.
S10
Figure S10. 1H NMR spectrum of P1.
S11
Figure S11. 1H NMR spectrum of P2.
S12
Figure S12. 1H NMR spectrum of P3.
Figure S13. Cyclic voltammograms of P1, P2, and P3 films cast on platinum electrodes using a
Ag/Ag+ reference electrode, platinum counter electrode, and 0.1M Bu4NPF6 electrolyte in
S13
acetonitrile under an argon atmosphere. Readings taken with a 100 mV/s scan rate and
referenced to Fc/Fc+.
Figure S14. The Current-voltage (I/V) curves for OLEDs.
S14