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研究生：	陳巧佩 Chen, Chiao-Pei
論文名稱：	含氮冠醚基團共聚苯的合成、鑑定與其在化學感測器及電子注入層之應用 Synthesis, Characterization, Chemosensory and Electron Injection Layer Application of Copoly(p-phenylene) Containing Azacrown Ether Groups
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：	2012
畢業學年度：	100
語文別：	中文
論文頁數：	112
中文關鍵詞：	螢光感測器、含氮冠醚、高分子發光二極體、電子注入層
外文關鍵詞：	Chemosensor, Azacrown ether, PLED, EIL
相關次數：	點閱：76 下載：2
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本研究利用Suzuki聚合反應合成出側鏈帶有含氮冠醚基團和烷氧鏈的共聚苯高分子P0和P1，並探討P1對金屬離子的辨識能力與這些高分子作為PLED元件電子注入層時的應用。當加入鋅離子後，吸收光譜呈現藍位移，可推測為鋅離子與含氮冠醚有作用力，引發光誘導電荷轉移效應(PCT)，而螢光光譜強度的下降，推測是被激發後的發光團將能量轉移給鋅離子所引起的螢光焠熄，在其它離子的干擾之下，P1對鋅離子仍顯示高度的選擇性，溶液顏色變化可直接以肉眼辨識，靈敏度與其他文獻相比也有顯著提升，再加上可溶於一般有機溶劑及高極性溶劑，因此應用面大幅增加。在元件應用方面，以合成出來的高分子以及含碳酸鹽類的高分子作為電子注入層，取代傳統低功函數金屬，並以溼式製程製備高效率的PLED元件，其中以『P1 + 碳酸銫(Cs2CO3)』作為電子注入層時有最佳表現，最大電流效率由無電子注入層的0.44 cd/A提升至13.25 cd/A，提升了30倍，最大功率效率則由0.16 lm/W提升至9.16 lm/W，提升了57倍，而整體元件的效率、亮度、起始電壓也均有改善，達到提高PLED良率和效率的目的，原因推測為電子注入能力的提升，本研究並以原子力顯微鏡和光伏打量測來證明元件效率提升的假設。

A copoly(p-phenylene) chemical sensor (P1) containing pendant azacrown ether and ethylene glycol ether was synthesized by the Suzuki coupling reaction. The polymers were satisfactorily characterized by 1H NMR, FT-IR, elemental analysis, DSC, TGA, GPC, optical spectroscopy and cyclic voltametry. The absorption spectra showed blue-shift in the presence of Zn2+, which has been attributed to the photoinduced charge transfer (PCT) process. Also the fluorescence quenching was observed, which is resulted from energy transfer from fluorophore to Zn2+ directly. With increasing Zn2+ concentration the collision and complex formed between fluorophore and Zn2+ are raised, leading to significant reduction in fluorescence intensity. Upon the addition of Zn2+ the fluorescence quenching led to color changes which were detectable by naked eye. The static and dynamic quenching constants (Ksv) were 1.07×105 and 3.66×106 M-1, respectively, when measured in a mixture of THF and water (v/v = 9/1). Accordingly, it is a promising chemical sensor for Zn2+.
Interestingly, the P1 are also highly efficient electron-injection layer (EIL) for the fabrication of multi-layer polymer light-emitting diodes (PLEDs) by wet processes, particularly after chelating with metal carbonate (M2CO3: M is Na, K or Cs). The PLED with P1 plus Cs2CO3 as EIL revealed the best device performance. The maximum luminance, maximum current efficiency and maximum luminous power efficiency of PF-Green-B based device were 17049 cd/m2, 13.25 cd/A and 9.16 lm/W, respectively, which were superior to those without the EIL (891 cd/m2, 0.44 cd/A, 0.16 lm/W). In addition, the turn-on voltage was reduced greatly; for instance, it was reduced from 5.7 V to 3.5 V when P1 plus Cs2CO3 was employed as the EILs. The performance has been attributed to enhanced electron injection through cathode modification. The EIL decreases work function of the aluminum cathode, which was confirmed by the significant raise of open-circuit voltage (Voc) obtained in photovoltaic measurements. These results show that P1 is a promising lelectron-injection material for optoelectronic applications.

目錄
中文摘要	I
Abstract	II
致謝	IV
目錄	V
流程目錄	VIII
表目錄	VIII
圖目錄	IX

第一章  緒論	1
1-1  前言	1
1-2  金屬離子感測器的介紹	2
1-3  冠醚(Crown Ether)的介紹	3
1-4  共軛高分子的發展	4
    1-4-1 共軛高分子在化學感測器上的應用	4
    1-4-2 共軛高分子在有機發光二極體上的應用	5
1-5  螢光感測器的訊號變化與作用機制	6
    1-5-1 激發雙體(excimer)的形成	6
    1-5-2 光誘導的電子轉移(photoinduced electron transfer, PET)	7
    1-5-3 光誘導的電荷轉移(photoinduced charge transfer, PCT) 	8
    1-5-4 光誘導的能量傳遞(photoinduced energy transfer) 	10
1-6  元件發光原理及結構	11
    1-6-1 發光原理	11
    1-6-2 單層元件	12
    1-6-3 多層元件	13
1-7  研究目的與動機	14
第二章  文獻回顧	16
2-1  螢光理論	16
2-2  溶劑效應對光譜變化的影響	19
2-3  螢光焠熄效應(Fluorescence Quenching)	21
    2-3-1 動態焠熄模式(Dynamic Quenching)	21
    2-3-2 靜態焠熄模式(Static Quenching)	22
    2-3-3 綜合動態和靜態的焠熄模式(Sphere of Action Model)	24
2-4  能量轉移效應(Energy Transfer)	25
    2-4-1 輻射型態(trivial radiative)的能量轉移	25
    2-4-2 非輻射型態(non-trivial radiative)的能量轉移	26
2-5  有機電激發光二極體	28
    2-5-1 共軛高分子發光材料	29
    2-5-2 有機發光二極體效率的探討	29
2-6  反應機制 (Reaction Mechanism)	32
第三章  實驗內容	35
3-1  實驗裝置與設備	35
3-2  鑑定測量儀器	36
3-3  物性及光電性質測量儀器	37
3-4  待測溶液的配製與感測器的量測	43
3-5  實驗藥品材料	43
3-6  反應流程	46
3-7  單體以及高分子P0, P1的合成	47
3-8  元件製作	52
第四章  結果與討論	56
4-1  單體與高分子的合成與鑑定	56
    4-1-1 核磁共振光譜(NMR)	57
    4-1-2 元素分析儀(EA)	58
4-2  高分子性質的測量與分析	66
    4-2-1 高分子分子量分析	66
    4-2-2 高分子熱性質的分析	67
4-3  光學性質	70
    4-3-1 高分子在溶液中及薄膜態的光學性質	70
    4-3-2 相對量子效率	72
    4-3-3 高分子P1的溶劑效應	73
    4-3-4 螢光感測器對不同金屬陽離子的感測能力	75
    4-3-5 光譜變化的機制探討	79
    4-3-6 化學感測器對Zn2+靈敏度的探討	81
    4-3-7 化學感測器對Zn2+選擇性的探討	85
4-4  電化學性質	88
    4-4-1 高分子電化學性質探討	89
    4-4-2 高分子發光二極體(PLED)的元件特性	91
    4-4-3 元件效率提升的探討	99
第五章  結論	106
參考文獻	108
 
 流程目錄
Scheme 3-1. The synthetic procedures of P0 and P1	47

表目錄
Table 2-1. 取代基對物質螢光波長及效率的影響	18
Table 2-5-1. The work functions of various metals	31
Table 4-1. The Synthetic Result of Compounds	59
Table 4-2. The Synthetic Result of Polymers	60
Table 4-3. Characterization and Thermal Properties of the Polymers	68
Table 4-4. Optical properties of Polymers	71
Table 4-5. Absorption and fluorescence maximum wavelength of P1 in various solvents.	75
Table 4-6. Stern-Volmer constants of ethanol and THF systems	84
Table 4-7. Electrochemical potentials of Polymers	89
Table 4-8. Optoelectronic Properties of the Light-emitting Diodes	99
Table 4-9. Photovoltaic properties of the Light-emitting Diodes.	102
 
圖目錄
Figure 1-3-1. Cyclo-oligomers of ethylene oxide, from dioxane to 18-crown-6.	4
Figure 1-4-1. Enhancing the sensitivity of chemosensors by wiring chemosensory molecules in series.	5
Figure 1-5-1. Bisanthraceno-crown form an excimer with Na+ ion.	6
Figure 1-5-2. Principle of cation recognition by fluorescent PET sensors.	7
Figure 1-5-3. Crown-containing PET sensors	8
Figure 1-5-4. Spectral displacements of PCT sensors resulting from interaction of a bound cation with an electron-donating or electron-withdrawing group	9
Figure 1-5-5. Crown-containing PCT sensors in which the bound cation interacts with the donor group	10
Figure 1-5-6. Photoinduced energy transfer diagram.	11
Figure 1-6-1. Optical excitation diagram.	12
Figure 1-6-2. Electric excitation diagram	12
Figure 1-6-3. Single-layer device structure	13
Figure 1-6-4. Multi-layer device structure.	14
Figure 2-1-1. The electron spins of the ground state and excited states	16
Figure 2-1-2. The energy-level diagram for a typical photoluminescent molecule	17
Figure 2-2-1. Effects of the electronic and orientation reaction fields on the energy of a dipole in a dielectric medium, μE > μG. The smaller circles represent the solvent molecules and their dipole moments.	20
Figure 2-2-2. Jablonski diagram for fluorescence with solvent relaxation.	21
Figure 2-3-1. The mechanism of dynamic quenching	22
Figure 2-3-2. The mechanism of static quenching.	23
Figure 2-3-3. Comparison of (a) dynamic and (b) static quenching.	24
Figure 2-3-4. The mechanism of combination of dynamic and static quenching of the same population of fluorophores	24
Figure 2-3-5. Dynamic and static quenching of the same population of fluorophores	25
Figure 2-4-1. The reabsorption processes	25
Figure 2-4-2. Schematic diagram for Förster and Dexter energy transfer.	27
Figure 2-4-3. The Förster type energy transfer	26
Figure 2-4-4. The Dexter type energy transfer	27
Figure 2-5-1. The classification of light-emitting structures	28
Figure 2-5-2. The structure of conjugated polymer light-emitting materials	29
Figure 2-6-1. Mechanism of Wittig reaction	33
Figure 2-6-2. Mechanism of Vilsmeier-Haack reaction	33
Figure 2-6-3. Mechanism of Suzuki coupling Reaction	34
Figure 3-3-1. The three electrode cell of the cyclic voltammetry	41
Figure 3-8-1. Diagram illustration of the evaporation system	54
Figure 3-8-2. PLED devices	54
Figure 4-1-1. 1H NMR spectrum of compound 1	60
Figure 4-1-2. 1H NMR spectrum of compound 2	61
Figure 4-1-3. 1H NMR spectrum of compound 3	61
Figure 4-1-4. 1H NMR spectrum of compound 4	62
Figure 4-1-5. 1H NMR spectrum of compound 5	62
Figure 4-1-6. 1H NMR spectrum of compound 6	63
Figure 4-1-7. 1H NMR spectrum of compound 7	63
Figure 4-1-8. 1H NMR spectrum of compound 8	64
Figure 4-1-9. 1H NMR spectrum of compound 9	64
Figure 4-1-10. 1H NMR spectrum of compound DC	65
Figure 4-1-11. 1H NMR spectrum of P0	65
Figure 4-1-12. 1H NMR spectrum of P1	66
Figure 4-2-1. Thermo-gravimetric curves of P0 and P1 at a heating rate of 10 oC/min under nitrogen.	69
Figure 4-2-2. Differential scanning calorimetric curves of P0 and P1 obtained from second scan at a heating rate of 10 oC/min.	69
Figure 4-3-1. Normalized absorption spectra and photoluminescence emission spectra of P0 (a) in CHCl3 solution (b) in the film state	71
Figure 4-3-2. Normalized absorption spectra and photoluminescence emission spectra of P1 (a) in CHCl3 solution (b) in the film state.	72
Figure 4-3-3. Normalized photoluminescence emission spectra of P0、P1 and DC in CHCl3 solution (1.0×10-5 M).	72
Figure 4-3-4. Absorption spectrum of P1 in various solvent. The concentration of P1 was fixed at 10-5 M	74
Figure 4-3-5. Fluoresence spectrum of P1 in various solvent. The concentration of P1 was fixed at 10-5 M	74
Figure 4-3-6. Absorption spectra of P1 with various metal ions in solution (THF/H2O = 9/1, v/v).The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively	76
Figure 4-3-7. Fluorescence spectra of P1 with various metal ions in solution (THF/H2O= 9/1, v/v).The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively. Excitation wavelength was 411 nm	77
Figure 4-3-8. Fluorescence emission response profile of P1 upon addition of various metal ions in solution (THF/H2O = 9/1, v/v). The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively. Excitation wavelength was 411 nm	77
Figure 4-3-9. Absorption spectra of P1 with various metal ions in solution (Ethanol/H2O = 9/1, v/v). The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively	78
Figure 4-3-10. Fluorescence spectra of P1 with various metal ions in solution (Ethanol/H2O = 9/1, v/v).The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively. Excitation wavelength was 407 nm	78
Figure 4-3-11. Fluorescence emission response profile of P1 upon addition of various metal ions in solution (Ethanol/H2O = 9/1, v/v). The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively. Excitationength was 407 nm	79
Figure 4-3-12. Mechanism of the interaction between P1 with Zn2+	79
Figure 4-3-13. Absorption spectrum of various metal ions and fluorescence spectrum of P1 in solution (THF/H2O = 9/1, v/v). Excitation wavelength was 411 nm	80
Figure 4-3-14. Absorption spectrum of various metal ions and fluorescence spectrum of P1 in solution (Ethanol/H2O = 9/1, v/v). Excitation wavelength was 407 nm	81
Figure 4-3-15. Fluorescence spectra of P1 with varying concentration of Zn2+ in solution (THF/H2O = 9/1, v/v). The concentration of P1 was fixed at 10-5 M. Excitation wavelength was 411 nm	82
Figure 4-3-16. The Stern-Volmer plot of P1 with varying concentration of Zn2+ in solution (THF/H2O = 9/1, v/v). The concentration of P1 was fixed at 10-5 M. Excitation wavelength was 411 nm	82
Figure 4-3-17. Fluorescence spectra of P1 with varying concentration of Zn2+ in solution (Ethanol/H2O = 9/1, v/v). The concentration of P1 was fixed at 10-5 M. Excitation wavelength was 407 nm	83
Figure 4-3-18. The Stern-Volmer plot of P1 with varying concentration of Zn2+ in solution (Ethanol/H2O = 9/1, v/v). The concentration of P1 was fixed at 10-5 M. Excitation wavelength was 407 nm	83
Figure 4-3-19. Fluorescence spectra of P1 in solution (THF/H2O = 9/1, v/v). Quench by other metal ions (Li++ Na++ K++Ag++ Ca2++ Ba2++ Cu2++ Cd2++ Ni2++ Pb2++ Co2++ Fe2++ Fe3++ Al3++ Ru3+) with and without Zn2+.The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M,respectively. Excitation wavelength was 411 nm	85
Figure 4-3-20. Fluorescence spectra of P1 in solution (Ethanol/H2O = 9/1, v/v). Quench by other caions (Li++ Na++ K++Ag++ Ca2++ Ba2++ Cu2++ Cd2++Ni2++ Pb2++ Co2++ Fe2++ Fe3++ Al3++ Ru3+) with and without Zn2+.The concentration of P1 and metal ions were fixed at 10-5 M and 10-4 M, respectively. Excitation wavelength was 407 nm	86
Figure 4-3-21. Pictures of P1 in the presence of various metal ions and the target metal ions Zn2+. (Left image: only P1, middle image: P1+other caions, right image: P1+other cations+Zn2+)(a) THF/H2O = 9/1, v/v and (b) ethanol/H2O = 9/1, v/v	86
Figure 4-3-22. Fluorescence spectra of P1, P0 and DC with and without Zn2+ insolution (THF/H2O = 9/1, v/v)	87
Figure 4-3-23. Fluorescence spectra of P1 and DC with and without Zn2+ in solution (THF/H2O = 9/1, v/v)	88
Figure 4-4-1. Cyclic voltammogram of Ferrocene/Ferrocenium in 0.1 M n-Bu4NClO4, using glassy carbon as working electrode, scan rate: 100 mV/s.	90
Figure 4-4-2. Cyclic voltammogram of P0 and P1 in 0.1 M n-Bu4NClO4; scan rate: 100 mV/s	90
Figure 4-4-3 The energy level diagram of PF-Green-B and P1.	92
Figure 4-4-4. Brightness versus voltage characteristics of PLEDs with and without EIL. Device structure: ITO/PEDOT:PSS/PF-green-B/[ with/without EIL(P1)]/Al	94
Figure 4-4-5. Current density versus voltage characteristics of PLEDs with and without EIL. Device structure: ITO/PEDOT:PSS/PF-green-B/[ with/without EIL(P1) ]/Al	94
Figure 4-4-6. Current efficiency versus current density characteristics of PLEDs with and without EIL. Device structure: ITO/PEDOT:PSS /PF-green-B/[ with/without EIL(P1) ]/Al	95
Figure 4-4-7. Power efficiency versus current density characteristics with and without EIL. Device structure: ITO/PEDOT:PSS /PF-green-B/[ with/without EIL(P1) ]/Al	95
Figure 4-4-8. Brightness versus voltage characteristics of PLEDs with and without EIL. Device structure: ITO/PEDOT:PSS/PF-green-B/[ with/without EIL(P0) ]/Al	97
Figure 4-4-9. Current density versus voltage characteristics of PLEDs with and without EIL. Device structure: ITO/PEDOT:PSS/PF-green-B/[ with/without EIL(P0) ]/Al	97
Figure 4-4-10. Current efficiency versus current density characteristics of PLEDs with and without EIL. Device structure: ITO/PEDOT:PSS /PF-green-B/[ with/without EIL(P0) ]/Al	98
Figure 4-4-11. Power efficiency versus current density characteristics with and without EIL. Device structure: ITO/PEDOT:PSS /PF-green-B/[ with/without EIL(P0) ]/Al	98
Figure 4-4-12. Photovoltaic measurements of PLEDs with and without EIL (I-V Curve). Device structure:            ITO/PEDOT:PSS/PF-Green-B/[ with/without EIL(P1) ]/Al(80 nm)	101
Figure 4-4-13. Photovoltaic measurements of PLEDs with and without EIL (I-V Curve). Device structure:            ITO/PEDOT:PSS/PF-Green-B/[ with/without EIL(P0) ]/Al(80 nm) .	101
Figure 4-4-14. (a) AFM images of PF-Green-B film on top of PEDOT:PSS layer. (b) AFM images of P1 film on top of PF-Green-B layer.	103
Figure 4-4-15. Illustration of proposed link between P1 with Cs+	105


                                    

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