本文選題：酞菁 + 亞酞菁��； 參考：《天津理工大學(xué)》2017年碩士論文

【摘要】：有機(jī)場(chǎng)效應(yīng)晶體管(Organic field-effect transistor,OFET)由于其質(zhì)輕、低成本、制備工藝簡(jiǎn)單和大規(guī)模集成等優(yōu)勢(shì),逐漸成為有機(jī)光電領(lǐng)域的研究熱點(diǎn)。有機(jī)半導(dǎo)體材料是OFETs的重要組成部分,它直接影響OFETs載流子遷移率。到現(xiàn)今為止,研究較多的有機(jī)半導(dǎo)體材料其材型總體上都是p型,而n型則只占一小部分,另外n型材料又是制備雙極性場(chǎng)效應(yīng)晶體管、p-n結(jié)以及互補(bǔ)邏輯電路的不可或缺的組成成分,因此,開(kāi)發(fā)n型材料對(duì)于OFETs器件的研究具有非常重要的價(jià)值。酞菁以及亞酞菁類(lèi)化合物擁有多π電子共軛體系、很好的熱穩(wěn)定性能以及真空蒸鍍成膜等特點(diǎn),是制造OFETs器件的良好有機(jī)半導(dǎo)體材料。本文通過(guò)將氟原子取代基引入到化合物分子中,將p型材料轉(zhuǎn)變成n型材料,并將它們應(yīng)用到OFETs中。本文首先是用四氟鄰苯二甲酸酐作原料,依次經(jīng)過(guò)亞胺化、酰胺化和脫水反應(yīng)得到原料3,4,5,6-四氟鄰苯二甲腈,然后用3,4,5,6-四氟鄰苯二腈作原料制得了3種全氟金屬酞菁MPcF16(M=Cu,Zn,VO),其收率分別為52.46%,48.00%,14.90%;又用3,4,5,6-四氟鄰苯二甲腈作原料制得了3種全氟硼亞酞菁X-BsubPcF12(X=Br,Cl,F),其收率分別為30.01%,33.98%,28.57%;再用鄰苯二甲腈作原料制得了3種硼亞酞菁X-Bsubpc(X=Br,Cl,F),其產(chǎn)率分別是42.01%,38.97%,10.43%。利用紅外光譜、核磁共振以及質(zhì)譜等手段對(duì)合成的物質(zhì)進(jìn)行結(jié)構(gòu)表征。利用紫外-可見(jiàn)光譜、熒光光譜手段測(cè)定它們的光學(xué)性質(zhì);通過(guò)熱重分析來(lái)判定它們的熱穩(wěn)定性能;利用循環(huán)伏安(CV)曲線對(duì)它們進(jìn)行電化學(xué)性能分析�；衔锏墓馕锢硇阅軠y(cè)定結(jié)果顯示:全氟金屬酞菁化合物MPcF16(M=Cu,Zn,VO)在溶劑鄰二氯苯(DCB)、N,N-二甲基甲酰胺(DMF)、四氫呋喃(THF)中的紫外最大吸收波長(zhǎng)均在665~720 nm之間;全氟硼亞酞菁化合物X-BsubPcF12(X=Br,Cl,F)在甲苯(Toluene),氯仿(TCM),二氯甲烷(DCM)以及鄰二氯苯等溶劑中的紫外最大吸收波長(zhǎng)均位于570~580 nm之間;硼亞酞菁X-Bsubpc(X=Br,Cl,F)在Toluene,TCM,DCM等溶劑中的紫外最大吸收波長(zhǎng)均位于560~570 nm之間。合成物質(zhì)的電化學(xué)性能測(cè)定結(jié)果表明:全氟金屬酞菁化合物MPcF16(M=Cu,Zn,VO)的LUMO能級(jí)值介于-4.57~-4.50 eV之間;全氟硼亞酞菁化合物X-BsubPcF12(X=Br,Cl,F)的LUMO能級(jí)值介于-4.08~-4.05eV之間;硼亞酞菁化合物X-BsubPc(X=Br,Cl,F)的LUMO能級(jí)值介于-4.03~-4.00 eV之間。所合成物質(zhì)的熱穩(wěn)定性能測(cè)定結(jié)果顯示:全氟金屬酞菁化合物MPcF16(M=Cu,Zn,VO)其熱分解溫度(Td)均在380℃以上;全氟硼亞酞菁化合物X-BsubPcF12(X=Br,Cl,F)的Td都在360℃以上;硼亞酞菁X-BsubPc(X=Br,Cl,F)的Td均在280℃以上,說(shuō)明它們也具有良好的熱穩(wěn)定性能。選取全氟酞菁鋅ZnPcF16作為有源層應(yīng)用于OFETs,器件顯示出了n-溝道特性,其器件遷移率是1.3×10-2 cm2/V s。
[Abstract]:Due to its advantages of light weight, low cost, simple preparation process and large scale integration, organic field-effect transistors have gradually become the research hotspot in the field of organic photoelectricity. Organic semiconductor material is an important part of OFETs, which directly affects the carrier mobility of OFETs. Up to now, most of the organic semiconductor materials studied are p-type in general, and n-type in a small part. In addition, n-type material is an indispensable component in the fabrication of bipolar field-effect transistors and complementary logic circuits. Therefore, the development of n-type materials is of great value for the research of OFETs devices. Phthalocyanines and phthalocyanines have many 蟺 electron conjugation systems, good thermal stability and vacuum evaporation film, etc. They are good organic semiconductor materials for manufacturing OFETs devices. In this paper, fluorine atom substituents are introduced into compound molecules, p-type materials are transformed into n-type materials, and they are applied to OFETs. In this paper, first of all, using Tetrafluoro phthalic anhydride as raw material, the raw material was synthesized by imidization, amidation and dehydration. Then three kinds of perfluorinated metal phthalocyanine MPcF16 MCuCuZN were prepared from 3H 4N 4N 5N 6- tetrafluoro phthalonitrile in 52.46m 48.00 and 14.900.Three kinds of perfluoroborophthalocyanine X-BsubPcF12X BrClFN were prepared by using 3O4O4O4O4F5F6 tetrafluoro phthalonitrile as raw material, and the yields of them were 30.01n 33.9828.577.The yield of the three perfluorobenzocyanine phthalocyanines MPcF16 / MCuCuO4 was 30.01or 33.9828.570.Three perfluorobenzene phthalocyanines were used as raw materials. Three kinds of boron phthalocyanine X-BsubpcCX (BrC1-Cl-FN) were prepared from nitrile, and their yields were 42.01 and 38.97 and 10.43, respectively. The synthesized materials were characterized by IR, NMR and MS. Their optical properties were determined by UV-Vis and fluorescence spectra, their thermal stability was determined by thermogravimetric analysis, and their electrochemical properties were analyzed by cyclic voltammetry (CV) curves. The photophysical properties of perfluorinated metal phthalocyanine compounds (MPcF16 / MCuCuOZnVOO) were determined. The UV maximum absorption wavelengths of perfluorinated metal phthalocyanine compounds (MPcF16 / MCuCuOZnVOO) in the solvent of o-dichlorobenzene (DCB), N-dimethylformamide (DMF), tetrahydrofuran (THF), are between 665nm and 720nm. The UV maximum absorption wavelengths of perfluorinated boron phthalocyanine compound X-BsubPcF12XHBrCClF in toluene, chloroform, dichloromethane, dichloromethane (DCM) and o-dichlorobenzene are between 570nm and 580nm, and the maximum UV absorption wavelengths of boron phthalocyanine X-BsubpcXBrClClCF in solvents such as Tolueneine TCM-DCM are between 560nm and 570nm. The electrochemical properties of the synthesized compounds showed that the LUMO energy level of perfluorinated metal phthalocyanine compound MPcF16MCuCuZN was between -4.57 and 4.50 EV, and the LUMO energy level of perfluorinated boron phthalocyanine compound X-BsubPcF12XOBHBr-Cl-F) was between -4.08 and 4.05 EV, and the LUMO energy level of perfluorinated metal phthalocyanine compound (MPcF16) was between -4.08 and 4.05 EV. The LUMO energy level of boron phthalocyanine compound X-BsubPcC (X-BsubPcC) is between -4.03 and 4.00 EV, and the LUMO energy level is between -4.03 and 4.00 EV. The results of thermal stability test showed that the thermal decomposition temperature of the perfluorinated metal phthalocyanine compound MPcF16MCuCuCuZnVOO was above 380 鈩，

本文編號(hào)：1981710