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1 advances.sciencemag.org/cgi/content/full/4/10/eaau1956/dc1 Supplementary Materials for Poly(amide-imide) materials for transparent and flexible displays Sun Dal Kim, Byungyong Lee, Taejoon Byun, Im Sik Chung, Jongmin Park, Isaac Shin, Nam Young Ahn, Myungeun Seo, Yunho Lee, Yeonjoon Kim, Woo Youn Kim, Hyukyun Kwon, Hanul Moon, Seunghyup Yoo, Sang Youl Kim* This PDF file includes: *Corresponding author. Published 26 October 2018, Sci. Adv. 4, eaau1956 (2018) DOI: /sciadv.aau1956 Fig. S1. Synthetic route to uda. Fig. S2. 1 H NMR spectra of the nitro intermediate 2 and uda. Fig. S3. 13 C NMR spectra of the nitro intermediate 2 and uda. Fig. S4. FTIR spectra of the nitro intermediate 2 and uda. Fig. S5. Synthetic route to diacids. Fig. S6. 1 H NMR spectra of the diacids udac and sdac. Fig. S7. 13 C NMR spectra of the diacids udac and sdac. Fig. S8. FTIR spectrum of udac. Fig. S9. 1 H-NMR spectra of PAIs. Fig. S10. Photos of PAI films. Fig. S11. UV-vis spectra of PAIs. Fig. S12. TGA data of PAIs. Fig. S13. DSC data of representative PAIs. Fig. S14. DMA data of PAIs. Fig. S15. TMA data of PAIs. Fig. S16. 2D GIWAXS data of PAIs. Fig. S17. 1D deconvoluted plot of the GIWAXS data in out-of-plane direction. Fig. S18. 1D deconvoluted plot of the GIWAXS data in in-plane direction. Fig. S19. A plot of CTE and π-π stacking distance versus β-relaxation temperature determined by the DMA. Fig. S20. Synthetic route to model compound amide-uda and imide-uda. Fig. S21. 1 H NMR spectra of model compounds amide-uda and imide-uda. Fig. S C NMR spectra of model compound amide-uda and imide-uda. Fig. S23. FTIR spectra of model compound amide-uda and imide-uda. Fig. S24. Chemical and crystal structures of model compound amide-uda and imide-uda. Fig. S25. Ten most stable structures of PAI(s-s). Fig. S26. Ten most stable structures of PAI(s-u).
2 Fig. S27. Ten most stable structures of PAI(u-s). Fig. S28. Ten most stable structures of PAI(u-u). Fig. S29. Transfer characteristics of the IGZO TFTs under study. Table S1. Solubility of PAIs. Table S2. Birefringence of PAIs. Table S3. Transition temperatures of PAIs identified by the DMA. Table S4. Summary of the GIWAXS peak positions. Tables S5. Crystal data and structure refinement for amide-uda. Tables S6. Crystal data and structure refinement for imide-uda. Table S7. Bonding energies and geometric features of the 10 most stable dimeric structures for each of PAI(s-s), PAI(s-u), PAI(u-s), and PAI(u-u).
3 Fig. S1. Synthetic route to uda. Fig. S2. 1 H NMR spectra of (A) the nitro intermediate 2 and (B) uda.
4 Fig. S3. 13 C NMR spectra of (A) the nitro intermediate 2 and (B) uda.
5 Fig. S4. FTIR spectra of (A) the nitro intermediate 2 and (B) uda.
6 Fig. S5. Synthetic route to diacids.
7 Fig. S6. 1 H NMR spectra of the diacids (A: udac, B: sdac).
8 Fig. S7. 13 C NMR spectra of the diacids (A: udac, B: sdac).
9 Fig. S8. FTIR spectrum of udac.
10
11 Fig. S9. 1 H-NMR spectra of PAIs.
12 Table S1. Solubility of PAIs. Solvents PAI PAI PAI PAI PAI PAI PAI PAI (u-u) (s-s) (s-u) (u-s) (s-su) (su-s) (su-u) (su-su) THF DMF DMSO NMP DMAc m-cresol Ethyl acetate Acetone Anisole Chloroform ODCB Acetonitrile Toluene Diethyl ether n-hexane methanol a Solubility: ++, soluble at room temperature; -, insoluble. Abbreviations: THF, tetrahydrofuran; DMF, N,N-dimethylformamide; DMSO, dimethyl sulfoxide; NMP, N- methylpyrrolidone; DMAc, N,N-dimethylacetamide; ODCB, 1,2-dichlorobenzene.
13 Fig. S10. Photos of PAIs films. (A) PAI(u-u), (B) PAI(s-s), (C) PAI(s-u), (D) PAI(u-s), (E) PAI(s-su), (F) PAI(su-s), (G) PAI(su-u), (H) PAI(su-su).
14 Fig. S11. UV-Visible spectra of PAIs.
15 Table S2. Birefringence of PAIs. λ (nm) Polymer code nte a ntm b nav c Δn d ε e d(μm) f PAI(u-u) PAI(s-s) PAI(s-u) PAI(u-s) PAI(s-su) PAI(su-s) PAI(su-u) PAI(su-su) PAI(u-u) PAI(s-s) PAI(s-u) PAI(u-s) PAI(s-su) PAI(su-s) PAI(su-u) PAI(su-su) a nte: the in-plane refractive index. b ntm: the out-of-plane refractive index. c nav: the average refractive index (nav = (2nTE + ntm)/3). d Δn: birefringence (nte ntm). e Dielectric constant estimated from the refractive index: ε 1.10nav 2 f Film thickness for the refractive index measured.
16 Fig. S12. TGA data of PAIs.
17 Fig. S13. DSC data of representative PAIs.
18 Fig. S14. DMA data of PAIs. Table S3. Transition temperatures of PAIs identified by the DMA. Entry Tα ( o C) Tβ ( o C) Tγ ( o C) PAI (s-s) PAI (s-su) PAI (su-s) PAI (s-u) PAI (u-s) PAI (su-su) PAI (su-u) PAI (u-u)
19 Fig. S15. TMA data of PAIs. (A) Second scans. (B) Third scans.
20 Fig. S16. 2D GIWAXS data of PAIs.
21 Fig. S17. 1D deconvoluted plot of the GIWAXS data in out-of-plane direction.
22 Fig. S18. 1D deconvoluted plot of the GIWAXS data in in-plane direction.
23 Table S4. Summary of the GIWAXS peak positions. Peak position (Å -1 ) Characteristi c distance (Å) Peak position (Å -1 ) Characteristi c distance (Å) Inplane Assignment Outofplane Assignment π -π stack b PAI PAI ch-pack (s-s) a ch-pack (s-s) π -π stack PAI PAI ch-pack ch-pack (s-su) (s-su) π -π stack PAI PAI ch-pack ch-pack (su-s) (su-s) π -π stack PAI PAI ch-pack ch-pack (s-u) (s-u) π -π stack PAI PAI ch-pack ch-pack (u-s) (u-s) PAI PAI π -π stack (susu) su) ch-pack (su ch-pack π -π stack PAI PAI ch-pack ch-pack (su-u) (su-u) π -π stack PAI PAI ch-pack ch-pack (u-u) (u-u) a ch-pack: the interchain packing distance of polymer chains. b π -π stack: face-to-face π- stacking distance of polymer chains.
24 Fig. S19. A plot of CTE and π-π stacking distance versus β-relaxation temperature determined by the DMA.
25 Fig. S20. Synthetic route to model compound (A) amide-uda and (B) imide-uda.
26 Fig. S21. 1 H NMR spectra of model compound (A) amide-uda and (B) imide-uda.
27 Fig. S C NMR spectra of model compound (A) amide-uda and (B) imide-uda.
28 Fig. S23. FTIR spectra of model compound (A) amide-uda and (B) imide-uda.
29 Fig. S24. (A, B) Chemical structure of amide-uda (A) and imide-uda (B) model compounds. (C, E, G) Crystal structure of amide-uda in (100), (010), and (001) directions. (D, F, H) Crystal structure of imide-uda in (100), (010), and (001) directions. Full crystallographic details can be obtained free of charge from the Cambridge Crystallographic Data Center via (CCDC and ).
30 Tables S5. Crystal data and structure refinement for amide-uda. Empirical formula Formula weight Temperature Wavelength Crystal system Space group Unit cell dimensions b = (5) Å C28 H16 F6 N2 O2 120(2) K Å Monoclinic C c a = (18) Å c = (16) Å Volume (7) Å 3 Z 4 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) Crystal size x x mm 3 Theta range for data collection to Index ranges Reflections collected <=h<=12, -34<=k<=34, -11<=l<=11 Independent reflections 4724 [R(int) = ] Completeness to theta = % Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4724 / 2 / 343 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient Largest diff. peak and hole and e.å -3 n/a
31 Tables S6. Crystal data and structure refinement for imide-uda. Empirical formula Formula weight Temperature Wavelength Crystal system C30 H14 F6 N2 O4 120(2) K Å Space group C 2/c Unit cell dimensions Monoclinic a = (10) Å b = (2) Å c = (10) Å Volume (7) Å 3 Z 8 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 2352 Crystal size x x mm 3 Theta range for data collection to Index ranges Reflections collected <=h<=18, -35<=k<=35, -16<=l<=17 Independent reflections 5824 [R(int) = ] Completeness to theta = % Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 5824 / 0 / 379 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient n/a Largest diff. peak and hole and e.å -3
32 Fig. S25. Ten most stable structures of PAI(s-s).
33 Fig. S26. Ten most stable structures of PAI(s-u).
34 Fig. S27. Ten most stable structures of PAI(u-s).
35 Fig. S28. Ten most stable structures of PAI(u-u).
36 Table S7. Bonding energies and geometric features of the 10 most stable dimeric structures for each of PAI(s-s), PAI(s-u), PAI(u-s), and PAI(u-u). Name Bonding Parallel(P)/ Bonding Parallel(P)/ Intertwinedtwined? Inter- Energy Anti- Name Energy Antiparallel(A) (kcal/mol) parallel(a) (kcal/mol) PAI(s-s) A Yes PAI(u-s) A Yes PAI(s-s) A Yes PAI(u-s) A No PAI(s-s) A Yes PAI(u-s) A Yes PAI(s-s) A Yes PAI(u-s) A Yes PAI(s-s) P No PAI(u-s) A Yes PAI(s-s) A Yes PAI(u-s) A Yes PAI(s-s) A No PAI(u-s) A No PAI(s-s) P No PAI(u-s) A Yes PAI(s-s) A No PAI(u-s) A No PAI(s-s) A No PAI(u-s) A No PAI(s-u) A No PAI(u-u) A Yes PAI(s-u) A No PAI(u-u) A No PAI(s-u) A No PAI(u-u) A Yes PAI(s-u) A Yes PAI(u-u) A No PAI(s-u) A Yes PAI(u-u) A No PAI(s-u) A No PAI(u-u) A No PAI(s-u) A Yes PAI(u-u) A Yes PAI(s-u) A Yes PAI(u-u) A No PAI(s-u) A Yes PAI(u-u) A No PAI(s-u) P No PAI(u-u) A No
37 Fig. S29. Transfer characteristics of the IGZO TFTs under study. Black curve refers to the characteristics measured before bending; red one refers to the characteristics measured flat after being bent 10 times at a bending radius of 1.9mm; blue one indicates the characteristics measured flat one hour after the first run of the bending experiment.
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