Title Page
Contents
ABSTRACT 11
INTRODUCTION 13
EXPERIMENTAL SECTION 18
General Information 18
Synthesis 19
Absorption and Fluorescence Measurements 25
Thermal properties 25
DFT Calculations 25
Cyclic Voltammetry Measurements 26
Fluorescence quantum yields in solution and film 26
OLEDs device fabrications 26
Transient electroluminescence and magneto-electroluminescence measurements 27
RESULTS AND DISCUSSION 36
Synthesis 36
Theoretical calculations 38
Photophysical properties 45
Thermal properties 57
Electrochemical properties 60
OLEDs characterization 62
CONCLUSIONS 72
REFERENCES 73
국문요약 78
Table 1. Photophysical properties of AnBP_H, AnBP_OMe and AnBP_F. 68
Table 2. Calculated rate constant of AnBP_H, AnBP_OMe and AnBP_F. 69
Table 3. Thermal properties of AnBP_H, AnBP_OMe and AnBP_F. 69
Table 4. Electrochemical properties and experimental HOMO/LUMO energy level of AnBP_H, AnBP_OMe and AnBP_F. 70
Table 5. Emitting performance of OLEDs base on AnBP_H, AnBP_OMe and AnBP_F. 71
Figure 1. Device structure of OLEDs. 14
Figure 2. Photophysical mechanism of hot exciton materials. 14
Figure 3. ¹H NMR spectrum of compound 1 in CDCl₃. 29
Figure 4. ¹H NMR spectrum of compound 2 in CDCl₃ 29
Figure 5. ¹H NMR spectrum of compound 3 in CDCl₃. 30
Figure 6. (a) ¹H and (b) ¹³C NMR spectra of compound 4 in CDCl₃. 31
Figure 7. (a) ¹H and (b) ¹³C NMR spectra of compound 5 in CDCl₃ 32
Figure 8. (a) ¹H and (b) ¹³C NMR spectra of compound AnBP_H in CDCl₃. 33
Figure 9. (a) ¹H and (b) ¹³C NMR spectra of compound AnBP_OMe in CDCl₃ 34
Figure 10. (a) ¹H and (b) ¹³C NMR spectra of compound AnBP_F in CDCl₃ 35
Figure 11. Optimized molecular geometries with HOMO and LUMO levels and energies of AnBP_H, AnBP_OMe, and AnBP_F 39
Figure 12. Calculated low-lying excited states energy level diagram for AnBP_F, AnBP_H, and AnBP_OMe. 41
Figure 13. The natural transition orbitals (NTO) characteristics of the selected singlet and triplet states for AnBP_F, AnBP_H, and AnBP_OMe. 44
Figure 14. The absorption (a) and emission (b) spectra for AnBP_F, AnBP_H, and AnBP_OMe in 10 μM chloroform solution at 298 K. The excitation wavelength for... 47
Figure 15. (a) Solvent polarity dependence PL spectra for AnBP_F, and (b) Lippert–Mataga plots of the Stokes shift of emitters against the solvent polarity parameters... 50
Figure 16. (a) Solvent polarity dependence PL spectra for AnBP_H, and (b) Lippert–Mataga plots of the Stokes shift of emitters against the solvent polarity parameters... 51
Figure 17. (a) Solvent polarity dependence PL spectra for AnBP_OMe, and (b)Lippert–Mataga plots of the Stokes shift of emitters against the solvent polarity... 52
Figure 18. Transient photoluminescence (PL) decay spectra of the (a) AnBP_H, (b) AnBP_OMe, (c) and AnBP_F in film states and in toluene. 56
Figure 19. TGA diagrams for (a) AnBP_H, (b) AnBP_OMe, (c) and AnBP_F. 59
Figure 20. DSC diagrams for AnBP_H, AnBP_OMe, and AnBP_F. 59
Figure 21. Cyclic voltammogram of AnBP_H, AnBP_OMe, and AnBP_F in dichloromethane solution containing 0.1 M n-Bu₄NPF₆ as an electrolyte, at a scan... 61
Figure 22. Device architecture of non-doped device AnBP_H, AnBP_OMe, and AnBP_F. 63
Figure 23. Non-doped device performance of AnBP_H, AnBP_OMe, and AnBP_F. (a) External quantum efficiency (%)-Luminance (cd·m⁻²), (b) Current density (J)-... 65
Figure 24. (a) Time-resolved electroluminescence (TrEL) response and (b) magneto-electroluminescence (MEL) response of the non-doped AnBP_OMe device.... 67
Scheme 1. Synthetic scheme of AnBP_H, AnBP_OMe and AnBP_F. 37