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OLED용 청색발광 재료의 합성 및 분광 특성

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Alternative Title: Synthesis and Spectral characterization of Blue emitting materials for Organic Light-Emitting Diodes(OLEDs)

Abstract: These days, organic light-emitting diode(OLED) technology has captured tremendous interest and has rapidly developed since the discovery of organic electroluminescence roughly 20 years ago. Much of the attention given to OLEDs is due to the performance advantages that it has over other types of flat panel display(FPD) technologies, including the industry dominant liquid crystal displays(LCDs). Recognized advantages include nearly Lamberian emission, which provides wider viewing angles than LCD; fast response times, which facilitate grayscale and video capabilities in active matrix applications; and low-voltage operation, which leads to low-cost components and low-profile packaging.
This study was based on organic light-emitting diode(OLED). Especially, blue host and blue dopant for the emitting materials were synthesized by Ullmann Reaction, Buchwald-Hartwing Reaction and Suzuki-Miyaura Coupling. The structural property of reaction products were analyzed by 1H NMR(proton nuclear magnetic resonance), GC-Mass(gas chromatograph/ma
ss spectrophotometry), FAB-Mass spectrometry, ion chromatography(IC) and thermal stability, absorption and emission characterization were analyzed by DSC(differential scanning calorimetry), UV/VIS/NIR spectrophotometer, fluorescence spectrophotometer(PL), respectively. Finally electrical property were analyzed by cyclic voltammetry. In this study, it was known that blue emitting materials had a different characterization according to functional group.

Author(s): 박인섭

Issued Date: 2012

Awarded Date: 2012. 8

Type: Dissertation

Publisher: 부경대학교

URI: https://repository.pknu.ac.kr:8443/handle/2021.oak/25089
http://pknu.dcollection.net/jsp/common/DcLoOrgPer.jsp?sItemId=000001964974

Alternative Author(s): park, in seob

Affiliation: 부경대학교 대학원

Department: 대학원 인쇄공학과

Advisor: 손세모

Table Of Contents: 목 차 ⅰ
List of figures ⅵ
List of tables ⅷ
List of schemes ⅸ
List of appendix ⅸ

Abstract ⅹ

1. 서 론 1

2. 이 론 3
2-1. 유기발광다이오드(Organic Light Emitting Diode)의 구조 및 발광원리 3
2-2. 단 분자 OLED재료 5
2-2-1. 정공주입 및 정공수송재료 5
2-2-2. 전자주입 및 전자수송재료 8
2-2-3. 발광재료 9
2-2-3-1. 녹색(Green)발광재료 10
2-2-3-2. 청색(Blue)발광재료 11
2-2-3-3. 적색(Red)발광재료 12
2-3. 에너지 이동을 이용한 OLED소자의 고성능화: Host/dopant system 14
3. 실 험 17
3-1. 합성 시약 17
3-2. Heteroacene(HA) 합성 18
3-2-1. Heteroacene 1 18
3-2-1-1. 9,9-dimethyl-9H-fluorene의 합성(1) 18
3-2-1-2. 2,7-diiodo-9,9-dimethyl-9H-fluorene(HA1)의 합성(2) 19
3-2-2. Heteroacene 2의 합성 19
3-2-2-1. 9,9-diphenyl-9H-fluorene의 합성(3) 20
3-2-2-2. 2,7-dibromo-9,9-diphenyl-9H-fluorene(HA2)의 합성(4) 20
3-2-3. Heteroacene 3의 합성 21
3-2-3-1. 4,4'-dibromo-2-nitrobiphenyl의 합성(5) 22
3-2-3-2. 2,7-dibromo-9H-carbazole의 합성(6) 22
3-2-3-3. 2,7-dibromo-9-phenyl-9H-carbazole(HA3)의 합성(7) 23
3-3. Secondary amine(SA) 유도체 합성 24
3-3-1. Diphenylamine(SA1)의 합성(1) 24
3-3-2. N-phenylnaphthalen-1-amine(SA2)의 합성(2) 25
3-3-3. 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine(SA3)의 합성(3) 26
3-4. Blue dopant(BD)의 합성 27
3-4-1. Blue dopant(BD)1, 2, 3 의 합성 27
3-4-1-1. 9,9-dimethyl-N2,N2,N7,N7-tetraphenyl-9H-fluorene-2,7-
diamine(BD1)의 합성(1) 27
3-4-1-2. N2,N2,N7,N7,9,9-hexaphenyl-9H-fluorene-2,7-diamine
(BD2)의 합성(2) 28
3-4-1-3. N2,N2,N7,N7,9-pentaphenyl-9H-carbazole-2,7-diamine
(BD3)의 합성(3) 29
3-4-2. Blue dopant(BD)4, 5, 6 의 합성 30
3-4-2-1. 9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H
-fluorene-2,7-diamine(BD4)의 합성(4) 30
3-4-2-2. N2,N7-di(naphthalen-1-yl)-N2,N7,9,9-tetraphenyl-9H-fluorene
-2,7-diamine(BD5)의 합성(5) 31
3-4-2-3. N2,N7-di(naphthalen-1-yl)-N2,N7,9-triphenyl-9H-carbazole
-2,7-diamine(BD6)의 합성(6) 32
3-4-3. Blue dopant(BD)7, 8, 9 의 합성 33
3-4-3-1. N2,N7-Bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-N2,N7
-diphenyl-9H-fluorene-2,7-diamine(BD7)의 합성(7) 33
3-4-3-2. N2,N7-bis(9,9-dimethyl-9H-fluoren-2-yl)-N2,N7,9,9-tetraphenyl
-9H-fluorene-2,7-diamine(BD8)의 합성(8) 34
3-4-3-3. N2,N7-bis(9,9-dimethyl-9H-fluoren-2-yl)-N2,N7,9-triphenyl-
9H-carbazole-2,7-diamine(BD9)의 합성(9) 35
3-5. Naphthyl anthracene(NA) 유도체의 합성 36
3-5-1. 9-(naphthalen-1-yl)anthracene의 합성(1) 36
3-5-2. 9-bromo-10-(naphthalen-1-yl)anthracene의 합성(2) 37
3-5-3. 4,4,5,5-tetramethyl-2-(10-(naphthalen-1-yl)anthracen-9-yl)-1,3,2-
dioxaborolane(NA)의 합성(3) 38
3-6. Blue host(BH)의 합성 39
3-6-1. 9,10-di(naphthalen-1-yl)anthracene(BH1)의 합성(1) 40
3-6-2. 9-(naphthalen-1-yl)-10-(naphthalen-2-yl)anthracene(BH2)의
합성(2) 40
3-6-3. 9-(biphenyl-4-yl)-10-(naphthalen-1-yl)anthracen(BH3)의 합성(3) 41
3-6-4. 9-(9,9-dimethyl-9H-fluoren-2-yl)-10-(naphthalen-1-yl)anthracene
(BH4)의 합성(4) 42
3-6-5. 9,10-dibromoanthracene의 합성(5) 42
3-6-6. 9,10-diphenylanthracene(BH5)의 합성(6) 43
3-7. 합성물의 분석 및 측정 44
3-7-1. 1H NMR 스펙트럼 44
3-7-2. DSC(differential scanning calorimetry) 44
3-7-3. 광학적 특성평가 44
3-7-4. 순환 전압 전류(cyclic voltammetry) 측정 44

4. 결과 및 고찰 46
4-1. 유기 발광재료의 합성 46
4-2. 유기 발광재료의 분광특성 47
4-2-1. 9,9-dimethyl-N2,N2,N7,N7-tetraphenyl-9H-fluorene-2,7-diamie
(BD1)의 분광특성 48
4-2-2. N2,N2,N7,N7,9,9-hexaphenyl-9H-fluorene-2,7-diamine(BD2)의
분광특성 49
4-2-3. N2,N2,N7,N7,9-pentaphenyl-9H-carbazole-2,7-diamine(BD3)의
분광특성 50
4-2-4. 9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H
-fluorene-2,7-diamine(BD4)의 분광특성 51
4-2-5. N2,N7-di(naphthalen-1-yl)-N2,N7,9,9-tetraphenyl-9H-fluorene-2,7-
diamine(BD5)의 분광특성 52
4-2-6. N2,N7-di(naphthalen-1-yl)-N2,N7,9-triphenyl-9H-carbazole-2,7-
diamine(BD6)의 분광특성 53
4-2-7. N2,N7-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-N2,N7-
diphenyl-9H-fluorene-2,7-diamine(BD7)의 분광특성 54
4-2-8. N2,N7-bis(9,9-dimethyl-9H-fluoren-2-yl)-N2,N7,9,9-tetraphenyl-
9H-fluorene-2,7-diamine(BD8)의 분광특성 55
4-2-9. N2,N7-bis(9,9-dimethyl-9H-fluoren-2-yl)-N2,N7,9-triphenyl-9H-
carbazole-2,7-diamine(BD9)의 분광특성 56
4-2-10. 9,10-di(naphthalen-1-yl)anthracene(BH1)의 분광특성 57
4-2-11. 9-(naphthalen-1-yl)-10-(naphthalen-2-yl)anthracene(BH2)의
분광특성 58

4-2-12. 9-(biphenyl-4-yl)-10-(naphthalen-1-yl)anthracen(BH3)의 분광
특성 59
4-2-13. 9-(9,9-dimethyl-9H-fluoren-2-yl)-10-(naphthalen-1-yl)anthracene
(BH4)의 분광특성 60
4-2-14. 9,10-diphenylanthracene(BH5)의 분광특성 61
4-3. Host에 dopant를 도핑(doping)시에 분광특성 62
4-4. 유기 발광재료의 열적 안정성 64
4-5. 유기 발광재료의 전기적 특성 66
4-5-1. 순환 전압 전류(cyclic voltammetry, CV) 66

5. 결 론 70
6. References 72
7. Appendix 75

Degree: Master

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