Thermally Activated Delayed Fluorescence from Azasiline Based Intramolecular
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1 Supporting information for : Thermally Activated Delayed Fluorescence from Azasiline Based Intramolecular Charge-Transfer Emitter (DTPDDA) and a Highly Efficient Blue Light Emitting Diode Jin Won Sun, Jang-Yeol Baek, Kwon-Hyeon Kim, Chang-Ki Moon, Jeong-Hwan Lee, Soon- Ki Kwon, Yun-Hi Kim*, and Jang-Joo Kim* J. W. Sun, K.-H. Kim, C.-K. Moon, Dr. J.-H. Lee, Prof. J.-J. Kim Department of Materials Science and Engineering, Seoul National University, Seoul , South Korea jjkim@snu.ac.kr J. Y. Baek, Prof. S.-K. Kwon School of Materials Science and Engineering, Gyeongsang National University, Jinju, , South Korea Prof. Y.-H. Kim Department of Chemistry and Research Institute of Natural Sciences (RINS), Gyeongsang National University, Jinju, , South Korea. ykim@gnu.ac.kr
2 1. The angle-dependent PL intensities Figure S1. Angle-dependent PL intensities of the p-polarized light from 30-nm-thick films composed of mcp:tspo1:16 wt% DTPDDA at 465nm. Solid lines represent theoretical fits to the experimental data.
3 2. Material and methods All starting materials were purchased from Aldrich, TCI and Alfa Aesar. Pd catalyst was purchased from Umicore. Solvents were purified by distillation using Na or CaH 2. n-buli was used without further purification. 1 H and 13 C-NMR spectra were recorded using a Bruker Avance 300 MHz and Bruker 500 FT-NMR spectrometer; chemical shifts (ppm) were reported with tetramethylsilane as an internal standard. Thermal analysis was performed using a TA TGA 2100 thermogravimetric analyzer under a nitrogen atmosphere at a heating rate of 10 C/min. Differential scanning calorimeter (DSC) was conducted under nitrogen using a TA instrument 2100 DSC. The sample was heated at 10 C /min from 50 C to 350 C. UV vis absorption spectra were measured using a Perkin-Elmer LAMBDA-900 UV spectrophotometer. 3. Synthesis Synthesis of bis(2-bromophenylamine) : A mixture of 1-bromo-2-iodobenzene (29.6 g, mmol), 2-bromoaniline (15 g, mmol), NaOtBu (16.76 g, mmol), Pd 2 (dba) 3 (7.98 g, 8.72 mmol), Pd(dppf)Cl 2 (12.76 g, mmol), and toluene (174 ml) was refluxed for 12 hours. After evaporation of the solvent, the residue was diluted with H 2 O and extracted with diethyl ether. The diethyl ether layer was dried over MgSO 4 and diethyl ether was removed under reduced pressure. The crude product was purified by column chromatography using n-hexane as an eluent to give product as colorless oil. Yield: 64% (18. 3 g). ). 1 H NMR (300 MHz, CDCl 3, δ): (d, 2H), (d, 2H), (t, 2H), (t, 2H), 6.50 (s, 1H). Synthesis of N,N-bis(2-bromophenyl)-N-(4-methoxybenzyl)amine :
4 Bis(2-bromophenyl)amine (39 g, m)mol was added to the mixture of NaH (3.43 g, mmol) and 250 ml of dimethylformamide (DMF). After the solution was stirred for 1hour, 1-(chloromethyl)-4-methoxybenzene was added in the solution and stirred for 14 hours. Then, the water was added to solution, and the crude solid was precipitated. The crude solid was dissolved by dichloromethane, and extracted using water and dichloromethane. The dichloromethane layer was dried by using MgSO 4 and solvent was evaporated. The crude product was purified by column chromatography using mc/hexane (3:1) Yield: 87% (46. 8 g). ). 1 H NMR (300 MHz, CDCl 3, δ): (d, 2H), 7.5 (d, 2H), 7.3 (t, 2H), 7.0 (m, 4H), 6.80 (d, 2H), 4.7 (s, 2H), 3.7 (s, 3H) Synthesis of 5-(4-methoxybenzyl)-10,10-diphenyl-5,10-hydrodibenzo[b,e][1,4]azasiline : 2.5 M n-buli/hexane (17.7 ml, 44.2 mmol) was added to the mixture of 2-bromo-N-(2- bromophenyl)-n-(4-methoxybenzyl)aniline 9 g (20.1 mmol) and 60 ml of ether at 0 C. After the mixture was stirred for 30 min at 0 C, the solution of dichlorodiphenylsilane (5.6 g, 22.1 mmol) and 20 ml of ether was added to the mixture. The solution was stirred for 4 hours at room temperature. The solution was extracted by using water and ether. The ether layer was dried by MgSO4, and ether was evaporated. The crude product was purified by recrystallization using methylene dichloride/hexane (3/1) Yield: 75% (7. 8 g). 1 H NMR (300 MHz, CDCl 3, δ): (m, 12H), (t, 2H), (m, 6H), (d, 2H), 5.19 (s, 2H), 3.71 (s, 3H) Synthesis of 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline : 5-(4-Methoxybenzyl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline (37 g, 78.8 mmol), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (19.67 g, 86.6 mol), toluene (370 ml) and H2O (37 ml) were mixed, and refluxed at 80 C for 14 h. After reaction, the
5 solution was extracted by using ethyl acetate. The crude product was purified by column chromatography using hexane/ethyl acetate (7/1). Yield: 27% (7. 5 g). 1 H NMR (300 MHz, CDCl 3, δ): 9.43 (s, 1H), (m, 14H), (m, 2H), (m, 2H) Synthesis of 5-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-10,10-diphenyl-5,10- dihydrodibenzo[b,e][1,4]azasiline (DTPDDA) : A mixture of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (0.5 g, 1.29 mmol), 10,10- diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline (0.41 g, 1.16 mmol), sodium-t-butoxide (0.19 g, 1.93 mmol), tris(t-butyl)phosphine (0.03 g, 0.13 mmol), Pd 2 (dba) 3 (0.06 g, 8.1 mmol), and anhydrous toluene(5 ml) was stirred at 110 C for 12 hours under nitrogen atmosphere. After cooling to room temperature, the mixture was poured into water and then extracted with chloroform. The combined organic phase was washed with brine and dried over MgSO 4. The crude product was purified by column chromatography (methylene dichloride/n-hexane = 2/1). Yield: 63 % (0.54 g). Tm=352 C. 1 H NMR (300 MHz, CDCl 3, δ): (d, 2H), (d, 4H), (m, 12H), (d, 2H), (m, 6H), (t, 2H), (t, 2H), (d, 2H); 13 C NMR (500 MHz, CDCl 3, δ):171.88, , , , , , , , , , , , , , , , , , Mass: C 45 H 32 N 4 Si calcd , found The chemical structure of DTPDDA was confirmed by various spectroscopies such as 1 H-NMR, 13 C-NMR, and Mass as shown in Figure S2, Figure S3 and Figure S4, respectively. Figure S5 and Figure S6 shows the characterization of thermal stability of DTPDDA through thermogravimetry (TGA) and differential scanning calorimetry (DSC) in a nitrogen
6 atmosphere, respectively. The decomposition temperature was 400 C and the melting temperature was 325 C. This proves that DTPDDA has high thermal stability.
7 Figure S2. 1 H-NMR of DTPDDA Figure S3. 13 C-NMR of DTPDDA
8 Figure S4. Mass Spectroscopy of DTPDDA Figure S5. TGA data of DTPDDA.
9 Figure S6.DSC data of DTPDDA.
10 4. Comparison of LUMO and HOMO levels of DTPDDA and PXZ-TRZ Table S1. Comparison of LUMO and HOMO levels of DTPDDA and PXZ-TRZ through DFT calculations. Emitter Acceptor Unit LUMO (ev) Donor Unit HOMO (ev) DTPDDA Triazine 1.98 Azasiline 5.15 PXZ-TRZ Triazine 2.05 Phenoxazine 4.65
11 5. Cyclic Voltammetry(CV) measurement Figure S7.cyclic voltammetry data. Table S2. Achieved values from CV. Oxidation Onset (Volts) Reduction Onset (Volts) HOMO (ev) LUMO (ev) CV UV Edge Bandgap (Electrochemical) (ev) CV UV Edge DTPDDA
12 6. Information of TD-DFT calculations Table S3. X, Y, Z-Coordinates of DTPDDA with DFT calculation. Si N N N N C C C C C C C C C C C C C C C C C C C C C C C C C C
13 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H
14 H H H H H H H H H H H H H H H H
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