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研究生:何凱翔
研究生(外文):Kai-Hsiang-Ho
論文名稱:新穎電致螢光材料之合成及光物理性質探討
論文名稱(外文):Synthesis and Photophysical Studies of Novel PLED Materials
指導教授:歐陽文忠歐陽文忠引用關係
指導教授(外文):Wen-Chung Ou-Yang
學位類別:碩士
校院名稱:國立高雄應用科技大學
系所名稱:化學工程與材料工程系
學門:工程學門
學類:化學工程學類
論文種類:學術論文
畢業學年度:100
語文別:中文
論文頁數:157
中文關鍵詞:高分子材料固態膜
外文關鍵詞:polymer materialsSolid flim
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本研究成功合成出5種新穎的共軛高分子材料 ,其分別為PPzTpa-PPV、PThTpa-PPV、PThPz-PPV、PTh-PPV、及PThPh-PPV .首先, 利用 Suzuki Cross Coupling 方法和Vilsmeier-Haack reaction方法這兩種方法合成具有雙醛基的單體,再將PPV的單體改質成鹽類,最後使用Witting Polymerization reaction 做聚合反應,把這些具有雙醛基的單體搭配ppv鹽類改質成螢光共聚物材料 。
利用傅利葉轉換紅外線光譜儀(FT-IR)、核磁共振光譜儀(1H-NMR)及元素分析儀(EA),鑑定所合成出來螢光材料的化學結構,證明出利用Witting Polymerization reaction成功合成五種高分子出來,然後利用凝膠滲透層析儀(Gel permeation chromatography , GPC)、熱重分析儀(Thermal Gravimetric Analysis ,TGA)、偏光顯微鏡(Polarizing Microscopy, POM ) ,由GPC實驗結果顯示材料之重量平均分子量皆在3900~16000之間,TGA測出螢光才料皆在300 ℃才有明顯的裂解,故皆具有良好之熱穩定性。由POM圖像分析結果,固體膜有呈現結晶型的不均勻薄膜。利用紫外光-可見光吸收光譜分析(UltraViolet and visible Light absorption Spectroscopy, UV) 和光激螢光光譜儀(Photoluminescence spectrometer, PL)探討其光物理性質, 由實驗結果顯UV-vis 可以觀察出各材料的最大吸收峰波長落在. 440 nm左右 。由PL 圖譜可知螢光材料隨著濃度得的增加,特徵峰有紅位移(red-shift)的現象,在不同溶劑也會造成能量傳遞的差異,放射峰ca.550~580nm之間。 利用循環伏安法(Cyclic Voltammetry, CV),在電化學性質發項有導入4,4'-(thiophene-2,5-diyl)dibenzaldehyde單體的高分子 LUMO能階明顯下降。
This study has successfully synthesized five kinds of new conjugated polymer material, respectively for PPzTpa-PPV、 PThTpa-PPV、 PThPz-PPV、 PTH-PPV and PThPh-PPV.First, the synthesis of these two methods of the Suzuki Cross Coupling methods and Vilsmeier-Haack reaction method with dual aldehyde monomer, and then PPV monomer modified form salts, the Witting Polymerization reaction for the polymerization of monomer with these pairs of aldehyde the ppv modified monomers fluorescent copolymers.
Fourier leaves transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (1H-NMR) and elemental analyzer (EA), identification of the synthesized chemical structure of the fluorescent material to prove that the use of the the Witting Polymerization reaction was successfully synthesized five kinds of polymerout.Followed by gel permeation chromatography (Gel permeation chromatography, GPC), thermal gravimetric analysis (Thermal Gravimetric Analysis, TGA ), polarized light microscopy ( Polarizing Microscopy, POM) crops resistance analysis and observation of surface structure.GPC experimental results showed that weight average molecular weight of the materials are in 3900 to ~ 16000.TGA measured the fluorescent material are only 300 ℃ pyrolysis, it all has a good thermal stability..POM image analysis results, the solid film showing crystalline uneven film.UV-visible absorption spectroscopy (Ultra Violet and the visible Light, absorption Spectroscopy,UV)and photoluminescence spectrometer. (Photoluminescence spectrometer, PL) to investigate the photophysical properties Uv-vis maximum absorption peak wavelength of the material falls to about 440 nm Fluorescent material to increase as the concentration of peaks red shift (red-shift) of the phenomenon known by the PL spectra In different solvents can also cause differences in energy transfer, the emission peak between ca.550 ~ 580nm. By cyclic voltammetry (Cyclic Voltammetry ,CV) we ound that import 4,4'- (thiophene-2,5-diyl)-dibenzaldehyde monomer in the polymer LUMO energy levels decreased.
目錄
中文摘要.............................................................I
英文摘要...........................................................III
誌謝.................................................................V
目錄................................................................VI
表目錄...............................................................X
圖目錄..............................................................XI
第一章 緒論...........................................................1

1.1、前言............................................................1

1.2、理論背景.........................................................3

1.3、共軛高分子發光機制................................................4

1.4、文獻回顧.........................................................6

1.4.1、有機發光二極體材料..............................................6

1.4.2、小分子系統(OLED)元件要件介紹....................................7

1.4.3、雙層與多層結構之元件介紹........................................12

1.4.4、高分子發光二極體材料簡介........................................14

1.4.5、PLED 的製作與特性.............................................16

1.4.6、共軛高分子在溶液中的聚集效應....................................17

1.5、研究動機........................................................20

第二章 實驗實驗內容...................................................20

2.1、實驗內容簡易流程圖...............................................20

2.2、實驗藥品........................................................21

2.3、實驗儀器設備....................................................24

2.4、材料合成........................................................27

2.4.1、1,4-bis(hexyloxy)benzene(1)..................................28

2.4.2、1,4-bis(bromomethyl)-2,5-bis(hexyloxy)benzene(2).............28

2.4.3、(2,5-bis(hexyloxy)-1,4-phenylene)bis(methylene)bhosphonium)
is(triphe-nylpbromide(PPV) .......................................28

2.4.4、4,4'-(phenylazanediyl)dibenzaldehyde (4).....................29

2.4.5、10-hexyl-10H-phenothiazine-3,7-dicarbaldehyde (5)............30
2.4.6、4,4'-(thiophene-2,5-diyl)dibenzaldehyde (6)..................31

2.4.7、合成PPzTpa-PPV (P1)..........................................33

2.4.8、合成PThTpa-PPV(P2)...........................................35

2.4.9、合成PThPz-PPV (P3)...........................................37

2.4.10、合成PTh-PPV (P4)............................................39

2.4.11、合成PThPh-PPV (P5)..........................................41

第三章 材料化學結構定.................................................42

3.1、實驗方法........................................................42

3.2、傅利葉轉換紅外線光譜儀(FTIR)....................................42

3.3、核磁共振光譜儀..................................................50

3.4、元素分析儀......................................................58

第四章 材料物理性質探討...............................................60

4.1、熱穩定分析......................................................60

4.2、凝膠滲透儀分析(GPC)分子量分析.....................................65

4.3、 偏光顯微鏡.....................................................69

五章 材料光物理性質探討...............................................80

5.1、紫外光-可見光吸收光譜............................................80

5.2、螢光光譜儀(PL)THF溶液螢光光譜分析...............................84

5.3、螢光光譜儀(PL)Toluene溶液螢光光譜分析...........................95

5.4、固態膜系統螢光光譜分析..........................................106

5.4、CIE 色座標....................................................115

第六章 電化學與元件特性..............................................109

6.1、循環伏安實驗...................................................117

6.1.1 材料電化學特性................................................120

第七章 結論.........................................................125

參考文獻...........................................................127

自述...............................................................131
參考文獻
1. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, R. H.Friend, P. L. Burn and A. B. Holems, “Light-emitting diodes based on conjugated polymer”, Nature, 539 (1990).
2. H. G. Kiess, Conjugated conducting polymer,Springer-Verlag,
Heidelberg (1992).

3. T. Q. Nguyen, V. Doan, B. J. Schwartz, J. Chem.Phys., 110, 4068
(1999).

4. Shi, Y, Liu, J., Yang, Y. J. Appl. Phys., 87, 4254 (2000).

5. Liu J., Shi Y., Ma L. and Yang Y., J. Appl. Phys., 88, 605 (2000).

6.T. W. Lee, and O. O. Park, Adv. Mater., 12, 801, (2000).

7. R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N.
Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Bredas, M.
Logdlund & W. R. Salaneck “Electroluminescence in conjugated
polymers” Nature 397, 121-128 (1999).

8. M. Rohlfing and S. G. Louie “Optical Excitations in Conjugated
Polymers” Phys. Rev. Lett. 82 ,1959-1962 (1999).

9. M. Dietrich, J. Heinze, G. Heywang and F. Jonas, J. Electroanal. Chem.,
369, 87 (1994)
10. 香山科學會議第226次學術討論會。

11.J. L. Segura, Acta. Polym, 49, 319., 1998.

12.C. L. Lee, N. G. Kang, Y. S. Cho, J. S. Lee, J. J. Kim, Opt. Mater, 21, 119., 2002.
13.J. X. Jiang, C. Y. Jiang, W. Yang, H. Y. Zhen, F. Huang, Y. Cao, Macromulecule, 38, 4072 s, 2005.

14. Helfrich, W.; Schneider, W. G. J. Chem. Phys. 1966, 44, 2902.

15. Roberts, G. G.; McGinnity, M. M.; Barlow, W. A.; Vincett, P. S.
Solid State Commun, 32, 683. 1979.

16.Vincett, P. S.; Barlow, W. A.; Hann, R. A.; Roberts, G. G. Thin
Solid Film, 94, 171, 1982.

17. Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett, 51, 913. 1987.

18.Adachi, C.; Tokito, S.; Tsutsui, T.; Saito, S. Appl. Phys. Lett,
55, 1489. 1988.

19. Adachi, C.; Tokito, S.; Tsutsui, T.; Saito, S. Jpn. J. Appl. Phys.
, 27, L269,1988.

20. Adachi, C.; Tsutsui, T.; Saito, S. Jpn, J. Appl. Phys, 27,
L713. 1988.
21.Kido, J. Bull. Electrochem, 10, 1. 1994.

22. Kido, J.; Kimura, M.; Nagi, K. Science 1995, 267, 1332.

23.Cao, G. Y.; Treacy G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J.
Nature 1993, 357, 111.

24. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. Int. Ed.
1998, 37, 402.
25. Hwang, D. H.; Kim, S. T.; Li, X. C.; Chuah, B. S.; DeMello, J. C.;
Friend, R. H.; Moratti, S. C.; Holmes, A. B. Abstr. Pap. Am. Chem. S.
, 213, 319,1997.
26. Koch, F.; Heitz, W. Macromol. Chem. Phys, 198, 1531. 1997.

27.Pfeiffer, S.; Horhold, H. H. Macromol. Chem. Phys, 200,
1870. 1997.
28. Sarnecki, G. J.; Brun, P. L.; Kraft, A.; Reiend, R. H.; Holmes, A. B.Synth. Met., 55, 91,1993.
29.Hoger, F. W. S.; Zhang, C.; Pakbz, K.; Heeger, A. J. Polym. Prepr.
, 34, 197,1993.
30. Gurge, R. M.; Sarker, A.; Lathti, P. M.; Hu, B.; Karasz, F. E.
Macromolecules, 29, 4287,1996.

31. Gowri, R.; Mandal, D.; Shivkumar, B.; RamaKrishnan, S.
Macromolecules, 31, 1819 ,1998.

32. M. Hwang, H. Y. Chen, P. S. Chen, A. S. Liu, Y. Chi, C.F. Shu, F. I. Wu,P. T. Chou, S. M. Peng, G. H. Lee, Inorg. Chem, 44, 1344 (2005).

33. W. Tang, S. A. Vanslyke, Appl. Phys. Lett, 55, 913 (1987).

34. H. Burroughes, D. D. C. Bradley, A. R. Brown,R. N. Marks, K.
Mackay,R. H. Friend, P. L. Burns, A.B. Holmes, Nature, 347, 539 (1990).

35. S. H. Chen, C. H. Su, A. C. Su, S. A. Chen, J. Phys. Chem. B., 108,
8855 (2004).
36. C. Y. Yang, F. Hide, M. A. Diaz-garcia, A. J. Heeger, Y. Cao, Polymer, 39, 2299 (1998).

37. B. J. Schwartz. Annu, Rev. Phys. Chem., 54, 141 (2003).

38. S. Tretiak, A. Saxena, R. L. Martin, A. R. Bishop, J. Phys. Chem. B., 104, 7029 (2000).

39. S. Siddiqui, F. C. Spano., Chem. Phys. Lett., 308, 99 (1999).

40. L. Ding, D. A. M. Egbe, F. E. Karasz., Macromolecules, 37, 6124
(2004).

41. R. Jakubiak, C. J. Collison, W. C. Wan, L. J. Rothberg, B. R. Hsieh, J.Phys Chem. A., 103, 2394 (1999).
42. A. Menon, M. Galvin, K. A. Walz, L. Rothberg. Synth. Met., 141, 197
(2004).
43. C. J. Collison, L. J. Rothberg, V. Treemaneekarn, Y. Li,
Macromolecules, 34, 2346 (2001).

44. J. H. Hsu, W. Fann, P. H. Taso, K. R. Chuang, S. A. Chen, J. Phys.Chem. A, 103, 2375 (1999).

45. H. Zhang, X. Lu, Y. Li, X. Zhang, G. Yang, J. Photochem. Photobiol.A. 147, 15 (2002).

46. Y. Yang, Y. Shi, J. Liu and T. F. Guo, Electronic and Optical Properties of Conjugated Molecular Systems in Condensed Phases, 307-354 (2003).

47. Kristof Colladet, Macromolecules, 40, 65-72 (2004).

48. G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science,
270, 1789. 1995.
49. C.H. Lee, G. Yu, N.S. Sariciftci, D. Moses, K. Pakbaz, C. Zhang, A. J. Heeger, F. Wudl, Phys. Rev. B, 48, 15425 (1993).

50. Jin Young Kim,1,2 Kwanghee Lee,1,2* Nelson E. Coates,1 Daniel
Moses,1 Thuc-Quyen Nguyen,1 Mark Dante,1 Alan J. Heeger Science
317, 222 (2007).
51.歐陽文忠,國立清華大學化學工程研究所博士倫文(2006)
52. H. Zhen, C. Luo, W. Yang, W. Song, B. Du, J. Jiang, C. Jiang, Y.
Zhang, and Y. Cao, Macromolecules, 39, 1693 (2006).
53. A. Menon, H. P. Dong, Z. I. Niazimbetova, L. J. Rothberg, M. E.
Galvin,Chem. Mater, 14, 3668 (2002).
54. J. F. Rusling, S. L. Suib, Adv. Mater, 6, 922 (1994).
55. Y. Liu, M. S. Liu, A. K. Y. Jen, Acta. Polym , 50, 105 (1999).
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