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Chrysene 유도체의 합성 및 분광특성

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Abstract: From 1960 to today , By studying the display continuously , we can expect that the dream has come true in the display field which can be flexible and play a video clip. Especially OLED(organic light emitting diode) technology becomes the nucleus of the display field due to several reasons such as large size and mass production with low cost. There are some reasons why FPD(flat panel display) and OLED technology are sportlighted in Oraganic EL display. Firstly, it can provide more vivid color and free viewing angle than old technology LCD. Secondly, its fast response since it can emit different light in an instance When a flow of electricity is changed .
Lastly, OLED has a high energy efficiency than LED. Because it spends electric power for only emitted area instead of the whole of backlight. Additionally , OLED can perform theoretically outstanding capecity including thin film , light weight and high precision. Lately, a lot of studies are in progress to make a flexible display instead of flat one by using organic materials.
This study was based on organic light-emitting diode. It was focused in blue host and blue dopant for the emitting material and synthesized by Buchwald-Hartwing Reaction and Suzuki-Miyaura Coupling. The structural property of reaction products were analyzed by 1HNMR(proton nuclear magnetic resonance), GC-Mass(gas chromatography), FAB-Mass spectrometry, ion chromatography(IC) and thermal stability, absorption and emission characterization were anaylzed 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): 유지웅

Issued Date: 2015

Awarded Date: 2015. 2

Type: Dissertation

Publisher: 부경대학교

URI: https://repository.pknu.ac.kr:8443/handle/2021.oak/11814
http://pknu.dcollection.net/jsp/common/DcLoOrgPer.jsp?sItemId=000001967433

Affiliation: 부경대학교대학원

Department: 대학원 인쇄공학과

Advisor: 손세모

Table Of Contents: 목 차 ⅰ
List of Figures ⅴ
List of Table ⅶ
List of schemes ⅷ
List of appendix ⅸ

Abstract ⅹ

1. 서 론 1

2. 이 론 3
2-1. 유기발광다이오드(Organic Light Emitting Diode)의 기본구조 및
발광원리 3
2-2. 저분자 OLED 재료 6
2-2-1. 정공주입재료 6
2-2-2. 정공수송재료 7
2-2-3. 전자주입재료 9
2-2-4. 전자수송재료 10
2-2-5. 발광재료(형광) 11
2-2-5-1. 녹색발광재료 12
2-2-5-2. 적색발광재료 13
2-2-5-3. 청색발광재료 15
2-2-5-4. 노란색 및 주황색발광재료 16
2-2-6. Host/Dopant 간 에너지 전이를 이용한 고 효율화 17
3. 실 험 20
3-1. 합성 시약 20
3-2. 합성 방법 21
3-2. Blue dopant Chrysene 유도체(BC) 합성 21
3-2-1. 6,12-dibromochrysene 합성 22
3-2-2. N6,N6,N12,N12-tetraphenylchrysene-6,12-diamine(BC1)의 합성 22
3-2-3. N6,N6,N12,N12-tetrap-tolylchrysene-6,12-diamine(BC2)의 합성 23
3-2-4. N6,N12-di(naphthalen-2-yl)-N6,N12-diphenylchrysene-6,12-dia
mine(BC3)의 합성 24
3-2-5. N6,N12-di(naphthalen-1-yl)-N6,N12-diphenylchrysene-6,12-di
amine(BC4) 합성 24
3-2-6. N6,N12-di(biphenyl-4-yl)-N6,N12-diphenylchrysene-6,12-diami
ne(BC5) 합성 25
3-2-7. N6,N12-di(phenanthren-2-yl)-N6,N12-diphenylchrysene-6,12-d
iamine(BC6) 합성 26
3-2-8. N6,N12-bis(9,9-dimethyl-9H-fluoren-3-yl)-N6,N12-diphenylchr
ysene-6,12-diamine(BC7) 합성 27
3-2-9. N6,N12-bis(9,9-dimethyl-9H-fluoren-3-yl)-N6,N12-di(naphthal
en-1-yl)chrysene-6,12-diamine(BC8) 합성 28
3-3. Blue host 재료 (NP, naphtyl pyrene 유도체) 합성 30
3-3-1. 1,9-dibromopyrene 합성 30
3-3-2. 1-bromo-6-(naphthalen-1-yl)pyrene 합성 31
3-3-3. 1,6-di(naphthalen-1-yl)pyrene(NP1) 합성 32
3-3-4. 1-(naphthalen-1-yl)-6-phenylpyrene(NP2) 합성 33
3-3-5. 1-(naphthalen-1-yl)-6-(naphthalen-2-yl)pyrene(NP3) 합성 34
3-3-6. 1-(naphthalen-1-yl)-6-phenylpyrene(NP4) 합성 35
3-3-7. 1-(9H-fluoren-2-yl)-6-(naphthalen-1-yl)pyrene(NP5) 합성 36
3-4. 합성 물질의 분석 및 측정 38
3-4-1. 1H NMR 스펙트럼 38
3-4-2. DSC(differential scanning calorimetry) 38
3-4-3. UV/Vis absorption 스펙트럼 38
3-4-4. FL 스펙트럼 38
3-4-5. 순환 전압 전류 (Cyclic Voltammetry) 38

4. 결과 및 고찰 40
4-1. 유기 발광재료의 합성 40
4-2. 유기 발광재료의 분광특성 41
4-2-1. N6,N6,N12,N12-tetraphenylchrysene-6,12-diamine(BC1)의 분광특 성 42
4-2-2. N6,N6,N12,N12-tetrap-tolylchrysene-6,12-diamine(BC2)의 분광특 성 43
4-2-3. N6,N12-di(naphthalen-2-yl)-N6,N12-diphenylchrysene-6,12-diami
ne(BC3)의 분광특성 44
4-2-4. N6,N12-di(naphthalen-1-yl)-N6,N12-diphenylchrysene-6,12-diami
ne(BC4)의 분광특성 45
4-2-5. N6,N12-di(biphenyl-4-yl)-N6,N12-diphenylchrysene-6,12-diamine
(BC5)의 분광특성 46
4-2-6. N6,N12-di(phenanthren-2-yl)-N6,N12-diphenylchrysene-6,12-dia
mine(BC6)의 분광특성 47
4-2-7. N6,N12-bis(9,9-dimethyl-9H-fluoren-3-yl)-N6,N12-diphenylchry
sene-6,12-diamine(BC7)의 분광특성 48
4-2-8. N6,N12-bis(9,9-dimethyl-9H-fluoren-3-yl)-N6,N12-diphenylchry
sene-6,12-diamine(BC8)의 분광특성 49
4-2-9. 1,6-di(naphthalen-1-yl)pyrene(NP1)의 분광특성 50
4-2-10. 1-(naphthalen-1-yl)-6-phenylpyrene(NP2)의 분광특성 51
4-2-11. 1-(naphthalen-1-yl)-6-(naphthalen-2-yl)pyrene(NP3)의 분광
특성 52
4-2-12. 1-(naphthalen-1-yl)-6-phenylpyrene(NP4)의 분광특성 53
4-2-13. 1-(9H-fluoren-2-yl)-6-(naphthalen-1-yl)pyrene(NP5)의
분광특성 54
4-3. Host에 dopant 도핑 시 분광특성 55

4-4. 유기 화합물의 열적 안정성 58
4-5. 유기발광재료의 전기적 특성 60
4-5-1. 순환 전압 전류(Cyclic Voltammetry, CV) 60

5. 결 론 64
Reference 65

List of Figures

Figure 1. Structure of Organic Light Emitting Diode and emission process of the organic Light Emitting Diode 5
Figure 2. Chemical structure of hole injection materials 7
Figure 3. Chemical structure of hole transfer materials 8
Figure 4. Chemical structure of electron injection materials 10
Figure 5. Chemical structure of electron transfer materials 11
Figure 6. Chemical structure of emitting materials 12
Figure 7. Chemical structure of green emitting materials 13
Figure 8. Chemical structure of red emitting materials 14
Figure 9. Chemical structure of blue emitting materials 16
Figure 10. Chemical structure of yellow and orange emitting materials 17
Figure 11. Diagram for Förster and Dexter energy transfer 18
Figure 12. The most ideal host/dopant system 19
Figure 13. UV/Vis. absorption and photoluminescence spectra of BC1 in
the MC solution 42
Figure 14. UV/Vis. absorption and photoluminescence spectra of BC2 in
the MC solution 43
Figure 15. UV/Vis. absorption and photoluminescence spectra of BC3 in
the MC solution 44
Figure 16. UV/Vis. absorption and photoluminescence spectra of BC4 in
the MC solution 45
Figure 17. UV/Vis. absorption and photoluminescence spectra of BC5 in
the MC solution 46
Figure 18. UV/Vis. absorption and photoluminescence spectra of BC6 in
the MC solution 47
Figure 19. UV/Vis. absorption and photoluminescence spectra of BC7 in
the MC solution 48
Figure 20. UV/Vis. absorption and photoluminescence spectra of BC8 in
the MC solution 49
Figure 21. UV/Vis. absorption and photoluminescence spectra of NP1 in
the MC solution 50
Figure 22. UV/Vis. absorption and photoluminescence spectra of NP2 in
the MC solution 51
Figure 23. UV/Vis. absorption and photoluminescence spectra of NP3 in
the MC solution 52
Figure 24. UV/Vis. absorption and photoluminescence spectra of NP4 in
the MC solution 53
Figure 25. UV/Vis. absorption and photoluminescence spectra of NP5 in
the MC solution 54
Figure 26. Photoluminescence spectra of NP1 MC solution with
BC1, BC5 concentration(10wt%) 55
Figure 27. Photoluminescence spectra of NP1 MC solution with
BC7, BC8 concentration(10wt%) 55
Figure 28. Photoluminescence spectra of NP3 MC solution with
BC1, BC5 concentration(10wt%) 56
Figure 29. Photoluminescence spectra of NP3 MC solution with
BC7, BC8 concentration(10wt%) 56
Figure 30. Photoluminescence spectra of NP5 MC solution with
BC1, BC5 concentration(10wt%) 57
Figure 31. Photoluminescence spectra of NP5 MC solution with
BC7, BC8 concentration(10wt%) 57
Figure 32. DSC Curves of BC(1, 2, 3, 4) 58
Figure 33. DSC Curves of BC(5, 6, 7, 8) 58
Figure 34. DSC Curves of NP(1, 2, 3, 4, 5) 59
Figure 35. Comparison of blue emitting compounds by melting point
59
Figure 36. Cyclic voltammogram and UV/Vis absorption spectra BC1
61
Figure 37. Cyclic voltammogram of blue dopants 62
Figure 38. Eletrochemical potentials and energy level blue dopants 62
Figure 39. Cyclic voltammogram of blue hosts 63
Figure 40. Eletrochemical potentials and energy level blue hosts 63

List of Tables

Table 1. Spectral characteristics of BC1 in the MC solution 42
Table 2. Spectral characteristics of BC2 in the MC solution 43
Table 3. Spectral characteristics of BC3 in the MC solution 44
Table 4. Spectral characteristics of BC4 in the MC solution 45
Table 5. Spectral characteristics of BC5 in the MC solution 46
Table 6. Spectral characteristics of BC6 in the MC solution 47
Table 7. Spectral characteristics of BC7 in the MC solution 48
Table 8. Spectral characteristics of BC8 in the MC solution 49
Table 9. Spectral characteristics of NP1 in the MC solution 50
Table 10. Spectral characteristics of NP2 in the MC solution 51
Table 11. Spectral characteristics of NP3 in the MC solution 52
Table 12. Spectral characteristics of NP4 in the MC solution 53
Table 13. Spectral characteristics of NP5 in the MC solution 54

List of Schemes

Scheme 1. Synthesis of blue dopants(chrysene 유도체) 21
Scheme 2. Synthesis of blue dopant(6,12-dibromochrysene) 22
Scheme 3. Synthesis of blue dopant(BC1) 23
Scheme 4. Synthesis of blue dopant(BC2) 23
Scheme 5. Synthesis of blue dopant(BC3) 24
Scheme 6. Synthesis of blue dopant(BC4) 25
Scheme 7. Synthesis of blue dopant(BC5) 26
Scheme 8. Synthesis of blue dopant(BC6) 27
Scheme 9. Synthesis of blue dopant(BC7) 28
Scheme 10. Synthesis of blue dopant(BC8) 29
Scheme 11. Synthesis of blue hosts(naphtyl pyrene 유도체) 30
Scheme 12. Synthesis of 1,9-dibromopyrene 31
Scheme 13. Synthesis of naphtyl pyrene 1step 32
Scheme 14. Synthesis of naphtyl pyrene(NP1) 33
Scheme 15. Synthesis of naphtyl pyrene(NP2) 34
Scheme 16. Synthesis of naphtyl pyrene(NP3) 35
Scheme 17. Synthesis of naphtyl pyrene(NP4) 36
Scheme 18. Synthesis of naphtyl pyrene(NP5) 37

List of Appendix

Appendix 1. 1H NMR spectrum of 6,12-dibromochrysene 67
Appendix 2. 1H NMR spectrum of BC1 67
Appendix 3. 1H NMR spectrum of BC2 68
Appendix 4. 1H NMR spectrum of BC3 68
Appendix 5. 1H NMR spectrum of BC4 69
Appendix 6. 1H NMR spectrum of BC5 69
Appendix 7. 1H NMR spectrum of BC6 70
Appendix 8. 1H NMR spectrum of BC7 70
Appendix 9. 1H NMR spectrum of BC8 71
Appendix 10. 1H NMR spectrum of Naphtylpyrene 71
Appendix 11. 1H NMR spectrum of NP1 72
Appendix 12. 1H NMR spectrum of NP2 72
Appendix 13. 1H NMR spectrum of NP3 73
Appendix 14. 1H NMR spectrum of NP4 73
Appendix 15. 1H NMR spectrum of NP5 74

Degree: Master

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