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研究生：	李至程 Lee, Chih-Cheng
論文名稱：	側鏈含三苯胺與咔唑基團之主體高分子的合成及其在電激磷光元件的應用 The Synthesis and Optoelectronic Properties of Electrophosphorescent Host Polymers Containing Triphenylamine and Carbazole
指導教授：	陳雲 Chen, Yun
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2008
畢業學年度：	96
語文別：	英文
論文頁數：	150
外文關鍵詞：	Luminescence, Copolymerization, Light-emitting diode (LEDs)
相關次數：	點閱：51 下載：0
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Phosphorescent organic light-emitting devices (PHOLEDs) based on polymeric materials have attracted great attention currently, and been extensively investigated owing to their potential uses. In this essay, a series of side-chain polymers containing pendant carbazole, styryltriphenylamine and/or triphenylamine chromophores were designed and synthesized. All new synthesized monomers and polymers were identified by 1H NMR, FT-IR, and elemental analysis (EA). Thermal properties of these polymers were determined using TGA and DSC. The optical, electrochemical, and electroluminescent properties of these polymers were investigated.
A series of vinyl copolymers poly(9-vinylcarbazole-co-N-(4-(4-(4-vinylbenzyloxy)styryl)phenyl)-N-phenylbenzenamine) (PVKST) and homopolymer poly(N-(4-(4-(4-vinylbenzyloxy)styryl)phenyl)-N-phenylbenzenamine) (PVST) containing pendant carbazole and styryltriphenylamine chromophores from their corresponding precursor copolymers poly(9-vinylcarbazole-co-1-(chloromethyl)-4-vinylbenzene) (PCB) and poly(1-(chloromethyl)-4-vinylbenzene) (PSV) have been successfully synthesized by using the free radical polymerization and Williamson condensation. Vinyl copolymers poly(9-vinylcarbazole-co-4-vinyltriphenylaimne) (PVKT) series containing pendant carbazole and triphenylamine, and vinyl homopolymer poly(4-vinyltriphenylaimne) (PTPA) containing pendant triphenylamine chromophores have been successfully synthesized by using the free radical polymerization. In chapter 4 and 5, PTPA containing pendant hole-transporting triphenylamine chromophores was first used as a host material in green phosphorescent light-emitting diodes. The PL spectrum of PTPA showed an intrinsic peak (375 nm) attributed to triphenylamine groups and an excimer emission (440 nm). The PL and EL spectra of the blends [PTPA:Ir(ppy)3] showed dominant green emission attributed to Ir(ppy)3 due to efficient energy transfer from PTPA to Ir(ppy)3. The HOMO levels of PVST and PTPA, estimated from onset oxidation potentials in cyclic voltammograms, were -5.14 and -5.36 eV, which are much higher than -5.8 eV of conventional poly(9-vinylcarbazole) (PVK) host owing to high hole-affinity of the triphenylamine groups. The best performance was obtained with the EL device (ITO/PEDOT:PSS/PTPA:Ir(ppy)3(1 wt%):PBD(40 wt%)/Ca/Al), the maximal luminance and the maximal luminance efficiency were 8358 cd/m2 and 4.5 cd/A, respectively. The optoelectronic performances of phosphorescent EL devices, using PVST and PTPA as hosts and Ir(ppy)3 as dopant (ITO/PEDOT:PSS/PVST or PTPA:Ir(ppy)3(4 wt%):PBD(40 wt%)/BCP/Ca/Al) show the best performance device (PTPA as host), in which the maximal luminance and luminance efficiency were 9219 cd/m2 and 6.1 cd/A, respectively. Moveover, the EL performance of PTPA was greatly improved relative to that of PVK. In chapter 6, the emission spectra (both PL and EL) of the blends [PVKT1~PVKT88 with 4 wt% Ir(ppy)3] showed dominant green emission (517 nm) attributed to Ir(ppy)3 due to efficient energy transfer from PVKT11~PVKT88 to Ir(ppy)3. The HOMO levels of PVKT11~PVKT88, estimated from onset oxidation potentials in cyclic voltammetric, were -5.42 ~ -5.18 eV, which are much higher than -5.8 eV of conventional poly(9-vinylcarbazole) (PVK) host owing to high hole-affinity of the triphenylamine groups. The optoelectronic performances of phosphorescent EL devices, using PVKT11~PVKT88 as hosts and Ir(ppy)3 as dopant (ITO/PEDOT:PSS/PVKT11~PVKT88:Ir(ppy)3(4 wt%):PBD(40 wt%)/BCP/Ca/Al), were greatly improved relative to that of PVK. The best performance was obtained with PVKT45 device, in which the maximal luminance and luminance efficiency were 11501 cd/m2 and 10.6 cd/A, respectively. In chapter 7, the blend films of hole-transporting type host (PVKST) and phosphorescent green system [Ir(ppy)3] were prepared to tune color emission. The EL spectra of the blend films [PVKST:Ir(ppy)3] show a major emission at 515 nm and a minor peak at 435 nm, which are attributed to Ir(ppy)3 and PVST, respectively. The C.I.E. 1931 coordinates of the blend LED devices shift from (0.29, 0.61) for PVK to (0.33, 0.40) for PVST with the increase of PVST content.

Abstract----------------------------------------------I
Acknowledgements------------------------------------III
List of Schemes------------------------------------VIII
List of Tables---------------------------------------IX
List of Figures---------------------------------------X
Chapter 1 General Introduction------------------------1
Chapter 2 Literature Review and Theoretical Background--3
2-1 Historical Development of Electroluminescence-------3
2-2 Type of Electroluminescent Materials----------------6
2-3 Device Structure------------------------------------8
2-3-1 Single-layer devices------------------------------11
2-3-2 multi-layer PLED devices--------------------------12
2-4 Principle of Photoluminescence----------------------14
2-5 Fluorescence and Phosphorescence	-------------------16
2-6 Model of Exciton Formation--------------------------18
2-7 Inter-chain Excitons--------------------------------21
2-8 Förster and Dexter Energy Transfer------------------23
2-9 Triplet Harvesting----------------------------------26
2-10 Exciton Trapping at a Matrix Site and Energy Transfer---------------------------------------------------------28
2-11 Phosphorescent Emitters----------------------------30
2-12 Host Materials for phosphorescent Emitters---------32
2-12-1 General Requirements-----------------------------32
2-12-2 Carbazole-Based Host Materials-------------------33
2-12-3 Tuning the Properties of Carbazole Derivatives---35
2-13 Eye Sensitivity Function, Color Matching Function and Chromaticity Diagram------------------------------------40
2-14 Research Motivation--------------------------------43
2-15 References-----------------------------------------45
Chapter 3 Experimental Section--------------------------51
3-1 Instruments of Chemical Synthesis-------------------51
3-2 Measurements----------------------------------------51
3-3 Materials-------------------------------------------56
3-4 Schemes of Monomers and Polymers--------------------58
3-5 Synthesized Procedures------------------------------61
Chapter 4	Poly(4-vinyltriphenylamine): Optical, Electrochemical Properties and its New Application as a Host Material of Green Phosphorsecent Ir(ppy)3 Dopant--------------------------------------------------------------83
4-1 Introduction----------------------------------------84
4-2 Experimental----------------------------------------85
4-3 Result and Discussion-------------------------------85
4-3-1 Synthesis and Characterization--------------------85
4-3-2 Optical Properties--------------------------------86
4-3-3 Electrochemical Properties------------------------90
4-3-4 Electroluminescent Properties---------------------92
4-4 Summary---------------------------------------------96
4-5 References------------------------------------------97
Chapter 5	New Host Homopolymers Containing Pendant Triphenylamine Deriatives Chromophores: Synthesis, Optical, Electrochemical Properties and its Blend with Ir(ppy)3 for Green Phosphorescent OLEDs-------------------99
5-1 Introduction---------------------------------------100
5-2 Experimental---------------------------------------101
5-3 Result and Discussion------------------------------102
5-3-1 Synthesis and Characterization-------------------102
5-3-2 Optical Properties-------------------------------104
5-3-3 Electrochemical Properties-----------------------107
5-3-4 Electroluminescent Properties--------------------109
5-4 Summary--------------------------------------------112
Chapter 6 New Host Copolymers Containing Pendant Triphenyamine and Carbazole for Efficient Green Phosphorescent OLEDs-----------------------------------115
6-1 Introduction---------------------------------------116
6-2 Experimental---------------------------------------117
6-3 Result and Discussion------------------------------118
6-3-1 Synthesis and Characterization-------------------118
6-3-2 Optical Properties-------------------------------120
6-3-3 Electrochemical Properties-----------------------123
6-3-4 Electroluminescent Properties--------------------126
6-3-4-1 Green Phosphor [Ir(ppy)3]----------------------126
6-3-4-1 Red Phosphor [Ir(piq)2acac]--------------------128
6-4 Summary--------------------------------------------130
6-5 References-----------------------------------------131
Chapter 7 Copolymers Containing Pendant Styryltriphenylamine and Carbazole: Synthesis, Optical, Electrochemical Properties and its Blend with Ir(ppy)3------------------------------------------------------------133
7-1 Introduction---------------------------------------134
7-2 Experimental---------------------------------------135
7-3 Result and Discussion------------------------------135
7-3-1 Synthesis and Characterization-------------------135
7-3-2 Optical Properties-------------------------------138
7-3-3 Electrochemical Properties-----------------------140
7-3-4 Electroluminescent Properties--------------------142
7-4 Summary--------------------------------------------144
7-5 References-----------------------------------------145
Chapter 8	Conclusions ----------------------------------147
Appendix-----------------------------------------------149
Curriculum Vitae---------------------------------------149
List of Publication------------------------------------150
                                    

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Chapter 5
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[2] M. A. Baldo, D. F. O’Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151.
[3] M. A. Baldo, M. E. Thompson, S. R. Forrest, Nature 2000, 403, 750.
[4] S. Tokito, T. Iijima, Y. Suzuki, H. Kita, T. Tsutsui, F. Sato, Appl. Phys. Lett. 2003, 83, 569.
[5] M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett. 1999, 75, 4.
[6] Y. Kawamura, K. Goushi, J. Brooks, J. J. Brown, H. Sasabe, C. Adachi, Appl. Phys. Lett. 2005, 86, 071104.
[7] C. -L. Lee, K. B. Lee, J. -J. Kim, Appl. Phys. Lett. 2000, 77, 2280.
[8] M.-J. Yang, T. Tsutsui, Jpn. J. Appl. Phys. 2000, 39, 828.
[9] K. M. Vaeth, C. W. Tang, J. Appl. Phys. 2002, 92, 3447.
[10] X. Yang, D. Neher, D. Hertel, T. K. Däubler, Adv. Mater. 2004, 16, 161.
[11] X. Gong, J. C. Ostrowski, G. C. Bazan, D. Moses, A. J. Heeger, M. S. Liu, A. K.-Y. Jen, Adv. Mater. 2003, 15, 45.
[12] X. Gong, S.-H. Lim, J. C. Ostrowski, D. Moses, C. J. Bardeen, G. C. Bazan, J. Appl. Phys. 2004, 95, 948.
[13] C. Jiang, W. Yang, J. Peng, S. Xiao, Y. Cao, Adv. Mater. 2004, 16, 537.
[14] J. Kavitha, S. -Y. Chang, Y. Chi, J. -K. Yu, Y. -H. Hu, P. -T. Chou, S. -M. Peng, G. -H. Lee, Y. -T. Tao, C. -H. Chien, A. J. Carty, Adv. Funct. Mater. 2005, 15, 223.
[15] Y. -L. Tung, S. -W Lee, Y. Chi, L. -S. Chen, C. -F. Shu, F. -I. Wu, A. J. Carty, P. -T. Chou, S. -M. Peng, G. -H. Lee, Adv. Mater. 2005, 17, 1059.
[16] M. Klessinger, J. Michl, “Excited States and Photochemistry of Organic Molecules”; Wiley-VCH: New York, 1995.
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[20] J. Jiang, C. Jiang, W. Yang, H. Zhen, F. Huang, Y. Cao, Macromolecules 2005, 38, 4072.
[21] Y. You, S. H. Kim, H. K. Jung, S. Y. Park, Macromolecules 2006, 39, 349.
[22] G. L. Schulz, X. Chen, S.-A. Chen, S. Holdcroft, Macromolecules 2006, 39, 9157.
[23] A. J. Sandee, C. K. Willianms, N. R. Evans, J. E. Davies, C. E. Boothby, A. Köhler, R. H. Friend, A. B. Holmes, J. Am. Chem. Soc. 2004, 126, 7041.
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[25] Y. -Y. Noh, C. -L. Lee, J. -J. Kim, K. Yase, J. Chem. Phys. 2003, 118, 2853.
[26] Y. Shirota, Y. Kuwabara, H. Inada, T. Wakimoto, H. Nakada, Y. Yonemoto, S. Kawami, K. Imai, Appl. Phys. Lett. 1994, 65, 807.
[27] Y. Shirota, T. Kobata, N. Noma, Chem. Lett.1989, 1145.
[28] M. Ikai, S. Tokito, Y. Sakamoto, T. Suzuki, Y. Taga, Appl. Phys. Lett. 2001, 79, 156.
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[32] C. Jiang, W. Yang, J. Peng, S. Xiao, Y. Cao, Adv. Mater. 2004, 16, 537.
[33] B. W. D’Andrade, M. E. Thompson, S. R. Forrest, Adv. Mater. 2002, 14,147.
[34] Y. Qiu, J. Qiao, Thin Solid Films 2000, 372, 265.
[35] S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H. -E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304.
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[37] Y. Kawamura, S. Yanagida, S. R. Forrest, J. Appl. Phys. 2002, 92, 87.
[38] C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, J. Appl. Phys. 2001, 90, 5048.
[39] T. Tsuboi, N. Aljaroudi, Opt. Mater. 2007 (in press).
Chpater 6
[1] J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Macay, R. H. Friend, P. L. Burns, A. B. Holmes, Nature 1990, 347, 539.
[2] M. A. Baldo, D. F. O’Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest. Nature 1998, 395, 151.
[3] M. A. Baldo, M. E. Thompson, S. R. Forrest. Nature 2000, 403, 750.
[4] S. Tokito, T. Iijima, Y. Suzuki, H. Kita, T. Tsutsui, F. Sato, Appl. Phys. Lett. 2003, 83, 569.
[5] M. A. Baldo, S. Lamansky, P. E. Burrows, M. E. Thompson, S. R. Forrest. Appl. Phys. Lett. 1999, 75, 4.
[6] Y. Kawamura, K. Goushi, J. Brooks, J. J. Brown, H. Sasabe, C. Adachi, Appl. Phys. Lett. 2005, 86, 071104.
[7] C. L. Lee, K. B. Lee, J. J. Kim, Appl. Phys. Lett. 2000, 77, 2280.
[8] M. J. Yang, T. Tsutsui, Jpn. J. Appl. Phys. 2000, 39, 828.
[9] K. M. Vaeth, C. W. Tang, J. Appl. Phys. 2002, 92, 3447.
[10] X. Yang, D. Neher, D. Hertel, T. K. Däubler, Adv. Mater. 2004, 16, 161.
[11] X. Gong, J. C. Ostrowski, G. C. Bazan, D. Moses, A. J. Heeger, M. S. Liu, A. K.Y. Jen, Adv. Mater. 2003, 15, 45.
[12] X. Gong, S. H. Lim, J. C. Ostrowski, D. Moses, C. J. Bardeen, G. C. Bazan, J. Appl. Phys. 2004, 95, 948.
[13] C. Jiang, W. Yang, J. Peng, S. Xiao, Y. Cao, Adv. Mater. 2004, 16, 537.
[14] J. Kavitha, S. Y. Chang, Y. Chi, J. K. Yu, Y. H. Hu, P. T. Chou, S. M. Peng, G. H. Lee, Y. T. Tao, C. H. Chien, A. J. Carty, Adv. Funct. Mater. 2005, 15, 223.
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[16] M. Klessinger, J. Michl, “Excited States and Photochemistry of Organic Molecules”; Wiley-VCH: New York, 1995.
[17] C. Adachi, R. C. Kwong, P. Djurovich, V. Adamovich, M. A. Baldo, M. E. Thompson, S. R. Forrest, Appl. Phys. Lett. 2001, 79, 2082.
[18] X. H. Yang, F. Jaiser, S. Klinger, D. Neher, Appl. Phys. Lett. 2006, 88, 21107.
[19] X. W. Chen, J. L. Liao, Y. M. Liang, M. O. Ahmed, H. E. Tseng, S. A. Chen, J. Am. Chem. Soc. 2003, 125, 636.
[20] J. Jiang, C. Jiang, W. Yang, H. Zhen, F. Huang, Y. Cao, Macromolecules 2005, 38, 4072.
[21] Y. You, S. H. Kim, H. K. Jung, S. Y. Park, Macromolecules 2006, 39, 349.
[22] G. L. Schulz, X. Chen, S. A. Chen, S. Holdcroft, Macromolecules 2006, 39, 9157.
[23] A. J. Sandee, C. K. Willianms, N. R. Evans, J. E. Davies, C. E. Boothby, A. Köhler, R. H. Friend, A. B. Holmes, J. Am. Chem. Soc. 2004, 126, 7041.
[24] H. Zhen, C. Jiang, W. Yang, J. Jiang, F. Huang, Y. Cao, Chem. Eur. J. 2005, 11, 5007.
[25] Y. Y. Noh, C. L. Lee, J. J. Kim, K. Yase, J. Chem. Phys. 2003, 118, 2853.
[26] Y. Shirota, Y. Kuwabara, H. Inada, T. Wakimoto, H. Nakada, Y. Yonemoto, S. Kawami, K. Imai, Appl. Phys. Lett. 1994, 65, 807.
[27] Y. Shirota, T. Kobata, N. Noma, Chem. Lett. 1989, 1145.
[28] M. Ikai, S. Tokito, Y. Sakamoto, T. Suzuki, Y. Taga, Appl. Phys. Lett. 2001, 79, 156.
[29] Y. Kuwabara, H. Ogawa, Y. Shirota, Adv. Mater. 1994, 6, 677.
[30] K. M. Yeh, C. C. Lee, Y. Chen, Synth Met, 2008 (In press).
[31] Y. Liu, M. S. Liu, A. K. Y. Jen, Acta. Polym. 1999, 50, 105.
[32] C. Jiang, W. Yang, J. Peng, S. Xiao, Y. Cao, Adv. Mater. 2004, 16, 537.
[33] B. W. D’Andrade, M. E. Thompson, S. R. Forrest, Adv. Mater. 2002, 14, 147.
[34] Y. Qiu, J. Qiao, Thin Solid Films 2000, 372, 265.
[35] S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H. E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2001, 123, 4304.
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[37] Y. Kawamura, S. Yanagida, S. R. Forrest, J. Appl. Phys. 2002, 92, 87.
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Chapter 7
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