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1 Copyright WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, Supporting Information for Advanced Optical Materials, DOI: /adom Staggered Face-to-Face Molecular Stacking as a Strategy for Designing Deep-Blue Electroluminescent Materials with High Carrier Mobility Wen-Cheng Chen, Yi Yuan, Guang-Fu Wu, Huai-Xin Wei, Li Tang, Qing-Xiao Tong,* Fu-Lung Wong, and Chun-Sing Lee*
2 Copyright WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, Supporting Information Staggered Face-to-Face Molecular Stacking as A Strategy for Designing Deep-Blue Electroluminescent Materials with High Carrier Mobility Wen-Cheng Chen, Yi Yuan, Guang-Fu Wu, Huai-Xin Wei, Li Tang, Qing-Xiao Tong*, Fu- Lung Wong, and Chun-Sing Lee* General Information: 1 H NMR was recorded with a Varian Gemin-400 spectrometer. Mass spectra were recorded on a PE SCIEX API-MS spectrometer. Elemental analysis (C, H, N) was performed using a Vario EL III CHNS elemental analyzer. UV-vis absorption and PL spectra were measured on a Perkin-Elmer Lambda 950 UV/vis Spectrometer and a Perkin- Elmer LS50 fluorescence spectrometer, respectively. Ionization potentials (IP) of the materials were detected on ITO substrates in a thin-film state via ultraviolet photoelectron spectroscopy (UPS) in a VG ESCALAB 220i-XL surface analysis system, while electron affinitys (EA) were estimated by subtracting from IP with optical band gaps. Thermogravimetric analysis (TGA) and differential scanning calorimetric (DSC) were respectively performed on a TA Instrument TGAQ50 and a TA Instrument DSC2910. Crystallographic data collections of BBTPI and XBTPI were performed on an Oxford Diffraction Gemini E (Cu X-ray source, Kα, λ = Å for BBTPI and Mo X-ray source, Kα, λ = Å for XBTPI) equipped with a graphite monochromator and ATLAS CCD detector (CrysAlis CCD, Oxford Diffraction Ltd) at room temperature. The structures were solved by direct methods (SHELXTL-97), all non-hydrogen atoms were refined with anisotropic thermal parameters. BBTPI: 9,10-phenanthrenequinone (2.50 g, 12 mmol), [1,1':4',1''-terphenyl]-4,4''- dicarbaldehyde (BBCHO) (1.43 g, 5 mmol), 4-tert-butylbenzenamine (1.92 ml, 12 mmol), and ammonium acetate (7.71 g, 100 mmol) were added into glacial acetic acid (80 ml) and 1
3 the mixture refluxed for 24 h under an argon atmosphere. After cooling to room temperature, an orange-yellow mixture was obtained and poured into methanol under stirring. The crude product was separated by filtration, washed with methanol, and dried under vacuum. The product was purified by column chromatography (silica gel) using CH 2 Cl 2 as eluent to give a pale yellow solid, with an 81.8 % yield (3.79 g). 1 H NMR (400 MHz, CD 2 Cl 2, δ): 8.85 (s, 1H), 8.82 (d, J = 4.3 Hz, 2H), 8.80 (s, 1H), 8.76 (d, J = 8.2 Hz, 2H), (m, 3H), 7.73 (t, J = 4.1 Hz, 8H), 7.70 (d, J = 8.5 Hz, 5H), 7.63 (d, J = 8.5 Hz, 4H), 7.54 (dd, J = 12.8, 7.7 Hz, 6H), 7.31 (t, J = 7.6 Hz, 2H), 7.25 (d, J = 7.3 Hz, 2H), 1.49 (s, 18H); MS (ESI) m/z: [M + H] + calcd for C 68 H 55 N 4, 927.4; found, Anal. calcd for C 68 H 54 N 4 : C, 88.09; H, 5.87; N, 6.04; found: C, 88.02; H, 5.91; N, XBTPI: The synthetic procedures were similar with BBTPI. Yield: 91.4 %. 1 H NMR (400 MHz, CD 2 Cl 2, δ): 8.87 (s, 2H), 8.81 (d, J = 8.4 Hz, 2H), 8.76 (d, J = 8.3 Hz, 2H), 7.78 (t, J = 7.4 Hz, 2H), 7.69 (d, J = 8.4 Hz, 10H), (m, 6H), (m, 8H), 7.16 (d, J = 2.5 Hz, 2H), 2.27 (d, J = 2.6 Hz, 6H), 1.47 (d, J = 2.8 Hz, 18H). MS (ESI) m/z: [M + H] + calcd for C 70 H 59 N 4, 955.5; found, Anal. calcd for C 70 H 58 N 4 : C, 88.01; H, 6.12; N, 5.87; found: C, 88.09; H, 6.08; N, Scheme S1. Synthetic procedures for BBTPI and XBTPI (a: Pd(PPh 3 ) 4, 4- formylphenylboronic acid, 2 M Na 2 CO 3, toluene, reflux; b: 9,10-Phenanthrenedione, 4-(tertbutyl)aniline, ammonium acetate, acetic acid, reflux) 2
4 Figure S1. The twisting molecular structures of a) BBTPI and b) XBTPI. Figure S2. The overlapped sections in the crystal of a) BBTPI and b) XBTPI. 3
5 Figure S3. Photoluminescent photos of BBTPI and XBTPI in a) dilute dichloromethane solution (10-6 mol L -1 ) and b) in solid state. Figure S4. Electric field dependent hole and electron mobility of the new compounds estimated by SCLC method. 4
6 Table S1. Crystallographic data and structure refinement for BBTPI and XBTPI. BBTPI XBTPI Empirical formula C 68 H 54 N 4 C 70 H 58 N 4 Formula weight Temperature 293(2) K 293(2) K Wavelength Crystal system, space group triclinic, P-1 triclinic, P-1 a = (3) Å α= (3) a = (7) Å α= (7) Unit cell dimensions b = (6) Å b = (11) Å β= (4) β= (7) c = (8) Å γ = (3) c = (13) Å γ = (7) Volume (11) Å (2) Å 3 Z, Calculated density 1, Mg/m 3 1, 1107 Mg/m 3 Absorption coefficient mm mm -1 F(000) Crystal size mm mm Theta range for data collection 3.34 to to Reflections collected / unique 9708 / 5334 [R(int) = ] / 5038 [R(int) = ] Completeness to theta = % 99.9 % Max. and min. transmission and and Data / restraints / parameters 5334 / 37 / / 0 / 334 Goodness-of-fit on F Final R indices [I > 2sigma(I)] R1 = , wr2 = R1 = , wr2 = R indices (all data) R1 = , wr2 = R1 = , wr2 = Largest diff. peak and hole and e. Å and e. Å -3 Table S2. Fitting parameters in SCLC measurements for BBTPI and XBTPI. Emitter Hole Electron µ 0 [10-4 cm 2 V -1 s -1 ] β [10-3 (V cm -1 ) -1/2 ] µ 0 [10-7 cm 2 V -1 s -1 ] β [10-3 (V cm -1 ) -1/2 ] BBTPI 25.6 ± ± ± ± 0.92 XBTPI 4.2 ± ± ± ± 0.74 Table S3. Key performance data for XBTPI- and BBTPI-based devices and other high efficiency nondoped blue light-emitting devices. Emitter V on [V] λ EL [nm] CE a) [cd A -1 ] PE b) [lm W -1 ] EQE c) [%] XBTPI , 2.01, , 1.32, , 4.80, , 0.05 This work TTP-TPI , -, , -, , -, , a TCPC , -, - -, -, , -, , b CzS , 1.88, , 1.10, , 4.20, , CzS , 0.82, , 0.59, , 2.69, , M , -, , -, , -, , b M , -, , -, , -, , b POAn , 3.0, - 3.3, 2.3, - 4.7, 4.5, , b DPT-TPI , -, , -, , -, , a Be(PPI) , 2.18, , 1.60, , 2.55, , d Zn(PPI) , 1.31, , 0.75, , 1.32, , d CzPhB , -, - 1.3, -, - 4.3, -, , c TPA-BPI , -, , -, , -, , a BBTPI , 5.35, , 4.41, , 5.60, , 0.10 This work DMPPP , -, - 1.9, -, - 5.2, -, , b TPA-PPI , 4.25, , 2.7, , 3.76, , c TPVAn , 4.2, - 2.8, -, - 5.3, 4.2, , a BD , 6.1, , 4.9, , 5.0, , d B2PPQ , -, , -, , -, , c BPPI , -, , -, , -, , a) Current efficiency, b) power efficiency, c) external quantum efficiency corresponding to the value at the maximum, 100 cd m -2 and 1000 cd m -2, respectively. d) Parallel to main text. CIE [x, y] Ref. d) 5
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