Acetylene linkage를 도입한 Carbazole 및 Naphthalimide계 Blue & Green 유기형광염료 합성 = Synthesis and properties of efficient Blue and Green fluorescent dyes introducing acetylene linkage groups in carbazole and naphthalimide derivatives

다국어 초록 (Multilingual Abstract)

Extended π-conjugated system have received continuous attention in the filed of organic light-emitting materials due to obtaing high efficienct, stable, pure blue light emitting materials. In this study, a series of fluorescent dyes based on carbazole and 1,8-naphthalimide derivatives introducing acetylene linkage have been synthesized by Sonogashira coupling reaction. The structures of synthesized fluorescent dyes were characterized by 1H NMR spectroscopy and MALDI-TOF Mass Spectrometer. The optical, electrochemical and thermal properties of synthesized fluorescent dyes were systematically characterized by time dependent density functional theory(TD-DFT) using Gaussian 09 program with the hybrid B3LYP exchange correlation function and the 6-31G basis set. Fluorescent dyes introducing acetylene linkage in carbazole exhibits good hole transporting ability in diphenylamine and benzophenone core. Fluorescent dyes 1-3, 7, 8 with higher energy levels would be more readily to donate electrons due to π-π conjugation effect which leads to a rise in HOMO energy. In the case of Fluorescent dyes introducing acetylene lingkage in 1,8-naphthalimide, good electron transporting ability is exhibited in core group. Energy band gap electrochemically estimated was modulated from 3.02 to 3.97 eV. Synthesized fluorescent dyes has thermostability at 280℃.

목차 (Table of Contents)

• Ⅰ. 서론 1
• 1.1. OLED . 3
• 1.1.1. OLED의 구조 및 원리 3
• 1.1.2. OLED의 재료 5
• 1.1.3. OLED의 형광재료 6
• 1.2. 주요 형광염료의 특성 9
• 1.2.1. Carbazole derivatives. 9
• 1.2.2. Naphthalimide derivatives 10
• 1.2.3. diphenylamine derivatives 12
• 1.2.4. Benzophenone derivatives. 13
• 1.2.5. 선행연구. 14
• 1.3. 연구목표. 16
• Ⅱ 실험 19
• 2.1. 시약 19
• 2.2. 합성 형광염료의 구조분석 20
• 2.3. 실험방법 21
• 2.3.1. Diphenylamine계 형광염료의 중간체 합성 21
• 2.3.2. Benzophenone계 형광염료의 중간체 합성 23
• 2.3.3. Carbazole계 형광염료의 중간체 합성 25
• 2.3.4. Naphthalimide계 형광염료의 중간체 합성 32
• 2.3.5. 형광염료 합성 40
• 2.4. TD-DFT calculation 54
• 2.5. Photochemical properties 54
• 2.6. Thermogravimetric analysis 54
• Ⅲ 결과 및 고찰 55
• 3.1. Diphenylamine계 형광염료 56
• 3.1.1. Diphenylamine계 형광염료 합성 56
• 3.1.2. Structural properties calculation 60
• 3.1.3. TD-DFT and Frontier Molecular orbital calculation 65
• 3.1.4. Absorption spectroscopy 71
• 3.1.5. Fluorescence Spectroscopy 74
• 3.1.6. Thermal properties 77
• 3.2. Benzophenone계 형광염료 79
• 3.2.1. Benzophenone계 형광염료의 합성 79
• 3.2.2. Structural properties calculation 81
• 3.2.3. TD-DFT and Frontier Molecular orbital calculation 85
• 3.2.4. Absorption spectroscopy 90
• 3.2.5. Fluorescence Spectroscopy 92
• 3.2.6. Thermal properties 93
• Ⅳ. 결론 95
• 참고문헌 98
• (Abstract) 103