電活性聚酰亞胺的制備及其電雙穩(wěn)態(tài)信息存儲(chǔ)行為的表征和機(jī)理研究
發(fā)布時(shí)間：2018-07-16 20:56
【摘要】：信息時(shí)代數(shù)據(jù)總量的爆炸式增長,要求新型的存儲(chǔ)材料及元件具有超高的存儲(chǔ)密度、超快的讀寫和響應(yīng)速度、低的啟動(dòng)電壓以及低成本易加工等優(yōu)點(diǎn)。傳統(tǒng)的半導(dǎo)體存儲(chǔ)技術(shù)以硅和鍺為主要原料,但是在器件的線寬和存儲(chǔ)點(diǎn)的大小上已經(jīng)接近上限,難以滿足新時(shí)代的要求。而新開發(fā)的聚合物基信息存儲(chǔ)材料,由于其柔性、低成本、易加工,超大容量,超低能耗及可通過分子剪裁實(shí)現(xiàn)性能調(diào)控等優(yōu)點(diǎn)而成為研究的熱點(diǎn)�？紤]到存儲(chǔ)器件在使用中的發(fā)熱問題和對(duì)機(jī)械性能的要求,具有優(yōu)異的熱穩(wěn)定性、化學(xué)穩(wěn)定性和尺寸穩(wěn)定性的聚酰亞胺成為重點(diǎn)研究的對(duì)象。對(duì)于聚酰亞胺基信息存儲(chǔ)材料,近年的研究熱點(diǎn)主要在于設(shè)計(jì)合成分子鏈中同時(shí)具有電子給體和電子受體的新型聚酰亞胺,以利于施加電壓后發(fā)生微觀上的電子給受體間的電荷轉(zhuǎn)移和宏觀上的電雙穩(wěn)態(tài)現(xiàn)象。到目前為止,學(xué)者們已經(jīng)合成出多種具有不同化學(xué)結(jié)構(gòu)的聚酰亞胺并獲得了不同的存儲(chǔ)性能,如易失的動(dòng)態(tài)隨機(jī)存儲(chǔ)(DRAM)和靜態(tài)隨機(jī)存儲(chǔ)(SRAM),以及非易失的一次寫入多次讀取(WORM)和閃存型(Flash)存儲(chǔ)性能。但是,多種影響因素的存在,如分子軌道能級(jí)、前線軌道能級(jí)差、分子空間構(gòu)型、電子給受體的給電子和吸電子能力、電荷捕捉位點(diǎn)的空間分布及捕獲電荷的能力、活性層厚度、材料表面形貌以及電極種類等,導(dǎo)致聚酰亞胺基存儲(chǔ)器件內(nèi)部的存儲(chǔ)機(jī)理十分復(fù)雜。因此,雖然該領(lǐng)域已經(jīng)出現(xiàn)較多的研究成果,但是仍然需要更加深入的研究和詳盡的分析。其中尤其重要的是,如何探索聚酰亞胺分子結(jié)構(gòu)和存儲(chǔ)性能的關(guān)系以實(shí)現(xiàn)對(duì)存儲(chǔ)行為的調(diào)控,并分析材料內(nèi)部的存儲(chǔ)機(jī)理。在本文中,我們?cè)O(shè)計(jì)合成了三個(gè)系列的新型電活性聚酰亞胺,研究了其信息存儲(chǔ)性能,并結(jié)合其光物理性能、電化學(xué)性能和分子模擬的結(jié)果,分別研究了電子給體的給電子能力、分子鏈中給受體的空間結(jié)構(gòu)、電荷捕捉位點(diǎn)的深度以及給受體空間分布對(duì)存儲(chǔ)性能和存儲(chǔ)機(jī)理的影響。本論文的主要研究?jī)?nèi)容和成果如下:(1)合成了含有給電子基團(tuán)-芘-的新型二胺DAPAP (N,N-二(4-氨基)苯基-1-芘胺),并將之與BAPF(9,9'-對(duì)(4-氨基)苯基芴)和DSDA(3,3',4,4'-二苯砜四酸二酐)共聚,通過調(diào)節(jié)DAPAP和BAPF的比例,制備了一系列新型功能化共聚聚酰亞胺(coPI-DAPAPx,x=100, 50, 20, 10, 5, 1, 0,其中x代表DAPAP占總的二胺單體的摩爾比例)。產(chǎn)物表現(xiàn)出良好的溶解性和優(yōu)異的熱穩(wěn)定性。通過旋轉(zhuǎn)涂膜和真空蒸鍍制備了具有ITO/聚酰亞胺/Au結(jié)構(gòu)的存儲(chǔ)器件,并對(duì)其存儲(chǔ)性能進(jìn)行研究。結(jié)果表明,DAPAP在該系列共聚型聚酰亞胺中作為主要的電子給體。隨著DAPAP含量的降低,對(duì)應(yīng)的聚酰亞胺的存儲(chǔ)特性由非易失向易失型轉(zhuǎn)變。DAPAP含量為100%、50%、20%和10%的聚酰亞胺表現(xiàn)出非易失的WORM型存儲(chǔ)特性,而DAPAP含量為5%和1%的聚酰亞胺表現(xiàn)出易失的SRAM型存儲(chǔ)特性。DAPAP含量為0%的聚酰亞胺不具有雙穩(wěn)態(tài)存儲(chǔ)性能。對(duì)表征結(jié)果和分子模擬結(jié)果進(jìn)行分析后認(rèn)為,隨著DAPAP含量的降低,聚酰亞胺分子的HOMO (最高已占據(jù)軌道)軌道能級(jí)和Eg(前線軌道能級(jí)差)降低,導(dǎo)致施加電壓后聚酰亞胺分子中形成的電荷轉(zhuǎn)移絡(luò)合物穩(wěn)定性降低,因而出現(xiàn)非易失到易失型存儲(chǔ)性能的轉(zhuǎn)變。(2)合成了三種含電子給體-蒽-的新型二胺,1-DAPAA (N,N-二(4-氨基)苯基-1 -蒽胺)、2-DAPAA(N,N-二(4-氨基)苯基-2-蒽胺)和 9-DAPAA (N,N-二(4-氨基)苯基-9-蒽胺),將其與6FDA (4,4'-(六氟異丙基)二酞酸酐)聚合,采用兩步法合成了三種含有相似電子給體的電活性聚酰亞胺,1-DAPAA-6FDA、2-DAPAA-6FDA 和 9-DAPAA-6FDA。三種聚酰亞胺的唯一區(qū)別在于,蒽作為側(cè)基,和聚酰亞胺主鏈相連接的位點(diǎn)不同(1-,2-,9-)。半導(dǎo)體分析結(jié)果表明,1-DAPAA-6FDA和9-DAPAA-6FDA具有非易失的WORM型存儲(chǔ)行為,而2-DAPAA-6FDA表現(xiàn)出易失的SRAM型存儲(chǔ)行為。分子模擬結(jié)果表明,三種二胺具有相似的給電子能力,Mulliken電荷分布結(jié)果也證明,三種聚酰亞胺中從基態(tài)到激發(fā)態(tài)發(fā)生電荷轉(zhuǎn)移的電量幾乎相同,因而排除了電子效應(yīng)對(duì)存儲(chǔ)性能造成的影響�？臻g結(jié)構(gòu)分析表明,上述的不同連接位點(diǎn)導(dǎo)致蒽基所在平面和主鏈間二面角(θ1)大小的不同,其中2-DAPAA-6FDA中的θ1最小,整個(gè)分子的平面性相對(duì)更好,利于電荷轉(zhuǎn)移和反向的電荷傳輸,因而表現(xiàn)出易失的SRAM型存儲(chǔ)性能。而1-D APAA-6FDA和9-DAPAA-6FD A因?yàn)檩旎椭麈滈g較大的二面角不利于電荷轉(zhuǎn)移,而呈現(xiàn)出非易失的WORM型存儲(chǔ)性能。(3)合成了兩種新型的含不同長度非共軛脂肪鏈結(jié)構(gòu)的二胺,DATP6Cz(N,N-二(4-氨基)苯基-6-(9-咔唑基)己胺)和DATP2Cz (N,N-二(4-氨基)苯基-2-(9-咔唑基)乙胺),并采用二步法,將其分別與兩種二酐,DSDA和NTDA (1,4,5,8-萘四甲酸二酐)縮聚,得到四種不同的聚酰亞胺,DATP6Cz-DSDA,DATP6Cz-NTDA,DATP2Cz-DSDA,DATP2Cz-NTDA。咔唑和聚酰亞胺主鏈之間亞乙基和亞己基的引入,成功改變了電子給體和分子鏈間的相對(duì)空間位置。半導(dǎo)體分析結(jié)果表明,含DSDA的兩種聚酰亞胺,DATP6Cz-DSDA和DATP2Cz-DSDA均呈現(xiàn)出非易失的WORM型存儲(chǔ)行為,而含NTDA的兩種聚酰亞胺,DATP6Cz-NTDA和DATP2Cz-NTDA分別呈現(xiàn)出易失的SRAM和DRAM型存儲(chǔ)行為。分子模擬結(jié)果表明,相比于NTDA中的羰基,DSDA中的砜基具有更強(qiáng)的電荷捕獲能力,且捕獲電荷之后形成的締合物不易解離,而NTDA捕獲電荷后形成的締合物容易解離,因而含DSDA和NTDA的聚酰亞胺分別呈現(xiàn)出非易失和易失的存儲(chǔ)性能。而不同長度的非共軛脂肪鏈導(dǎo)致解離過程中電荷從受體到給體之間的傳輸過程不同,要克服的能壘也不同,因而宏觀上表現(xiàn)出不同的保留時(shí)間,并分別呈現(xiàn)出SRAM和DRAM的存儲(chǔ)行為。綜上所述,本論文的設(shè)計(jì)思路及研究結(jié)果證明,通過分子模擬手段對(duì)電子給受體的結(jié)構(gòu)進(jìn)行有目的的設(shè)計(jì)和調(diào)節(jié),以調(diào)整電子給體的給電子能力、分子鏈中給受體的空間結(jié)構(gòu)、電荷捕捉位點(diǎn)的深度以及給受體空間分布等,以實(shí)現(xiàn)對(duì)聚酰亞胺基存儲(chǔ)材料存儲(chǔ)性能的調(diào)節(jié)。這種理論結(jié)合實(shí)踐的研究方法和多項(xiàng)研究結(jié)論為新型聚合物基存儲(chǔ)材料的研究提供了具有指導(dǎo)意義的準(zhǔn)則,對(duì)我國信息存儲(chǔ)材料和技術(shù)的發(fā)展具有重要意義。
[Abstract]:The explosive growth of the total amount of data in the information age requires that new storage materials and components have super high storage density, ultra fast reading and writing and response speed, low start voltage and low cost and easy processing. The traditional semiconductor storage technology is mainly made of silicon and germanium, but the size of the line width and the storage point of the device has been already made. It is difficult to meet the requirements of the new age, and the newly developed polymer based information storage materials have become the focus of research because of their flexibility, low cost, easy processing, super capacity, ultra-low energy consumption and performance control through molecular cutting. Polyimides with excellent thermal stability, chemical stability and dimensional stability have become the focus of research. In recent years, the focus of research on polyimide based information storage materials is to design a new polyimide with both electron donor and electron acceptor in the molecular chain to facilitate the application of voltage. The charge transfer between the electrons and the macroscopic electric bihomeostasis on the microcosmic electron acceptor. So far, scholars have synthesized a variety of Polyimides with different chemical structures and obtained different storage properties, such as volatile random storage (DRAM) and static random storage (SRAM), and non volatile one write times. Read (WORM) and flash memory (Flash) storage performance. However, there are many factors such as the molecular orbital energy level, the front orbital energy level, the molecular space configuration, the electron and electron absorption capacity of the electron to the receptor, the space distribution of the charge capture loci, the ability to capture the charge, the thickness of the active layer, the surface morphology of the material and the type of the electrode. The mechanism of storage in polyimide based memory is very complex. So, although many research results have been found in this field, more in-depth research and detailed analysis are needed, especially, how to explore the relationship between the molecular structure and storage performance of polyimide in order to achieve the storage behavior. In this paper, we designed and synthesized three series of new electroactive polyimides, and studied their information storage performance. In combination with their photophysical properties, electrochemical properties and molecular simulation results, we studied the electron donor capacity and the spatial junction of the molecules to the receptors in the molecular chain. The main research contents and results in this paper are as follows: (1) a new two amine DAPAP (N, N- two (4- amino) phenyl -1- pyrene) containing the electron group pyrene, and BAPF (9,9'- pair (4- amino) phenyl fluorene) and DSDA (3,3', 4,4) A series of new functional copolymerized polyimides (coPI-DAPAPx, x=100, x=100, 50, 20, 10, 5, 1, 0, and X representing DAPAP accounted for the total of the total two amine monomer) were prepared by adjusting the ratio of DAPAP and BAPF. The product showed good solubility and excellent thermal stability. Through rotating coating and vacuum, the product showed good thermal stability. The storage devices with ITO/ polyimide /Au structure were prepared by steam plating and their storage properties were studied. The results showed that DAPAP was the main electron donor in this series copolymerized polyimide. With the decrease of DAPAP content, the corresponding storage properties of polyimide were 100%, 50%, 20% from non-volatile and easy to lose type. And 10% polyimide showed nonvolatile WORM storage properties, while Polyimides with DAPAP content of 5% and 1% showed a loss of SRAM type storage properties of 0% polyimide with no bistable storage performance. The analysis of characterization results and molecular simulation results showed that polyimide decreased with the decrease of DAPAP content. The HOMO (the highest occupied orbital) orbital energy level and the Eg (front-line orbital energy difference) decrease, resulting in a decrease in the stability of the charge transfer complex formed in the polyimide molecules after the application of the voltage. Therefore, there is a change in the non volatile storage properties of the easily lost type. (2) three new two amines containing electron donor anthracene, 1-DAPAA (N, N- two (4), 4) have been synthesized. - amino) phenyl -1 - anthracene), 2-DAPAA (N, N- two (4- amino) phenyl -2- anthracene) and 9-DAPAA (N, N- two (4- amino) phenyl -9- anthracene), and polymerized with 6FDA (six fluoroisopropyl) two phthalic anhydride), and three kinds of electroactive polyimides containing similar electric subgroups were synthesized by two steps. Three kinds and three kinds of electroactive polyimides were synthesized. The only difference in polyimides is that anthracene is the side group and the site of the main chain of polyimide is different (1-, 2-, 9-). The result of semiconductor analysis shows that 1-DAPAA-6FDA and 9-DAPAA-6FDA have a nonvolatile WORM type storage behavior, while 2-DAPAA-6FDA shows a volatile SRAM type storage behavior. The molecular simulation results show that three kinds of two amines have phase. The Mulliken charge distribution results also show that the charge transfer from the ground state to the excited state in the three polyimides is almost the same, so the effect of the electron effect on the storage performance is excluded. ) the difference in size, in which the 2-DAPAA-6FDA is the smallest of theta 1, and the plane of the whole molecule is relatively better, which is beneficial to the charge transfer and the reverse charge transfer, thus showing the loss of SRAM type storage performance. The 1-D APAA-6FDA and 9-DAPAA-6FD A are not favorable for the charge transfer because the anthracene and the main chain between the main chains are not favorable for the charge transfer, and the non volatile WORM is presented. (3) two new types of amines, DATP6Cz (N, N- two (4- amino) phenyl -6- (9- carbazole) hexylamine) and DATP2Cz (N, N- two (4- amino) phenyl -2- (9- carbazole) ethylamine) are synthesized, and two step method is used to polycondensation with two kinds of two anhydride and two anhydride, two anhydride, four formic acid two anhydride, The introduction of four different polyimides, DATP6Cz-DSDA, DATP6Cz-NTDA, DATP2Cz-DSDA, DATP2Cz-NTDA. carbazole and polyimide chain, has successfully changed the relative space position between the electron donor and the molecular chain. The results of semiconductor analysis showed that two polyimides, DATP6Cz-DSDA and DATP2Cz-DSDA containing DSDA were found. The non volatile WORM type storage behavior is presented, and two kinds of polyimides containing NTDA, DATP6Cz-NTDA and DATP2Cz-NTDA exhibit the loss of SRAM and DRAM type storage behavior respectively. The molecular simulation results show that the sulfone group in DSDA has a stronger charge capture ability than the carbonyl group in NTDA, and the associates formed after the capture of the charge are not. It is easy to dissociate, and the associates formed after the NTDA capture the charge are easily dissociated, thus the polyimides containing DSDA and NTDA exhibit a non-volatile and volatile storage performance, and the different lengths of the non conjugated fat chains lead to the different transfer of the charge from the receptor to the donor during the dissociation process, and the energy barrier to be overcome is different, thus macroscopically. The storage behavior of SRAM and DRAM is presented with different retention times. To sum up, the design ideas and research results of this paper prove that the structure of electron donor is designed and regulated by molecular simulation, in order to adjust the electronic capacity of the electron donor and the spatial structure of the receptor in the molecular chain, The depth of the charge capture site and the spatial distribution of the receptor are used to regulate the storage properties of the polyimide based storage materials. This theory provides a guiding principle for the study of the new polymer based storage materials, which combines practical research methods and many research conclusions. Development is of great significance.
【學(xué)位授予單位】：北京化工大學(xué)
【學(xué)位級(jí)別】：博士
【學(xué)位授予年份】：2017
【分類號(hào)】：O633.22
本文編號(hào)：2127646
[Abstract]:The explosive growth of the total amount of data in the information age requires that new storage materials and components have super high storage density, ultra fast reading and writing and response speed, low start voltage and low cost and easy processing. The traditional semiconductor storage technology is mainly made of silicon and germanium, but the size of the line width and the storage point of the device has been already made. It is difficult to meet the requirements of the new age, and the newly developed polymer based information storage materials have become the focus of research because of their flexibility, low cost, easy processing, super capacity, ultra-low energy consumption and performance control through molecular cutting. Polyimides with excellent thermal stability, chemical stability and dimensional stability have become the focus of research. In recent years, the focus of research on polyimide based information storage materials is to design a new polyimide with both electron donor and electron acceptor in the molecular chain to facilitate the application of voltage. The charge transfer between the electrons and the macroscopic electric bihomeostasis on the microcosmic electron acceptor. So far, scholars have synthesized a variety of Polyimides with different chemical structures and obtained different storage properties, such as volatile random storage (DRAM) and static random storage (SRAM), and non volatile one write times. Read (WORM) and flash memory (Flash) storage performance. However, there are many factors such as the molecular orbital energy level, the front orbital energy level, the molecular space configuration, the electron and electron absorption capacity of the electron to the receptor, the space distribution of the charge capture loci, the ability to capture the charge, the thickness of the active layer, the surface morphology of the material and the type of the electrode. The mechanism of storage in polyimide based memory is very complex. So, although many research results have been found in this field, more in-depth research and detailed analysis are needed, especially, how to explore the relationship between the molecular structure and storage performance of polyimide in order to achieve the storage behavior. In this paper, we designed and synthesized three series of new electroactive polyimides, and studied their information storage performance. In combination with their photophysical properties, electrochemical properties and molecular simulation results, we studied the electron donor capacity and the spatial junction of the molecules to the receptors in the molecular chain. The main research contents and results in this paper are as follows: (1) a new two amine DAPAP (N, N- two (4- amino) phenyl -1- pyrene) containing the electron group pyrene, and BAPF (9,9'- pair (4- amino) phenyl fluorene) and DSDA (3,3', 4,4) A series of new functional copolymerized polyimides (coPI-DAPAPx, x=100, x=100, 50, 20, 10, 5, 1, 0, and X representing DAPAP accounted for the total of the total two amine monomer) were prepared by adjusting the ratio of DAPAP and BAPF. The product showed good solubility and excellent thermal stability. Through rotating coating and vacuum, the product showed good thermal stability. The storage devices with ITO/ polyimide /Au structure were prepared by steam plating and their storage properties were studied. The results showed that DAPAP was the main electron donor in this series copolymerized polyimide. With the decrease of DAPAP content, the corresponding storage properties of polyimide were 100%, 50%, 20% from non-volatile and easy to lose type. And 10% polyimide showed nonvolatile WORM storage properties, while Polyimides with DAPAP content of 5% and 1% showed a loss of SRAM type storage properties of 0% polyimide with no bistable storage performance. The analysis of characterization results and molecular simulation results showed that polyimide decreased with the decrease of DAPAP content. The HOMO (the highest occupied orbital) orbital energy level and the Eg (front-line orbital energy difference) decrease, resulting in a decrease in the stability of the charge transfer complex formed in the polyimide molecules after the application of the voltage. Therefore, there is a change in the non volatile storage properties of the easily lost type. (2) three new two amines containing electron donor anthracene, 1-DAPAA (N, N- two (4), 4) have been synthesized. - amino) phenyl -1 - anthracene), 2-DAPAA (N, N- two (4- amino) phenyl -2- anthracene) and 9-DAPAA (N, N- two (4- amino) phenyl -9- anthracene), and polymerized with 6FDA (six fluoroisopropyl) two phthalic anhydride), and three kinds of electroactive polyimides containing similar electric subgroups were synthesized by two steps. Three kinds and three kinds of electroactive polyimides were synthesized. The only difference in polyimides is that anthracene is the side group and the site of the main chain of polyimide is different (1-, 2-, 9-). The result of semiconductor analysis shows that 1-DAPAA-6FDA and 9-DAPAA-6FDA have a nonvolatile WORM type storage behavior, while 2-DAPAA-6FDA shows a volatile SRAM type storage behavior. The molecular simulation results show that three kinds of two amines have phase. The Mulliken charge distribution results also show that the charge transfer from the ground state to the excited state in the three polyimides is almost the same, so the effect of the electron effect on the storage performance is excluded. ) the difference in size, in which the 2-DAPAA-6FDA is the smallest of theta 1, and the plane of the whole molecule is relatively better, which is beneficial to the charge transfer and the reverse charge transfer, thus showing the loss of SRAM type storage performance. The 1-D APAA-6FDA and 9-DAPAA-6FD A are not favorable for the charge transfer because the anthracene and the main chain between the main chains are not favorable for the charge transfer, and the non volatile WORM is presented. (3) two new types of amines, DATP6Cz (N, N- two (4- amino) phenyl -6- (9- carbazole) hexylamine) and DATP2Cz (N, N- two (4- amino) phenyl -2- (9- carbazole) ethylamine) are synthesized, and two step method is used to polycondensation with two kinds of two anhydride and two anhydride, two anhydride, four formic acid two anhydride, The introduction of four different polyimides, DATP6Cz-DSDA, DATP6Cz-NTDA, DATP2Cz-DSDA, DATP2Cz-NTDA. carbazole and polyimide chain, has successfully changed the relative space position between the electron donor and the molecular chain. The results of semiconductor analysis showed that two polyimides, DATP6Cz-DSDA and DATP2Cz-DSDA containing DSDA were found. The non volatile WORM type storage behavior is presented, and two kinds of polyimides containing NTDA, DATP6Cz-NTDA and DATP2Cz-NTDA exhibit the loss of SRAM and DRAM type storage behavior respectively. The molecular simulation results show that the sulfone group in DSDA has a stronger charge capture ability than the carbonyl group in NTDA, and the associates formed after the capture of the charge are not. It is easy to dissociate, and the associates formed after the NTDA capture the charge are easily dissociated, thus the polyimides containing DSDA and NTDA exhibit a non-volatile and volatile storage performance, and the different lengths of the non conjugated fat chains lead to the different transfer of the charge from the receptor to the donor during the dissociation process, and the energy barrier to be overcome is different, thus macroscopically. The storage behavior of SRAM and DRAM is presented with different retention times. To sum up, the design ideas and research results of this paper prove that the structure of electron donor is designed and regulated by molecular simulation, in order to adjust the electronic capacity of the electron donor and the spatial structure of the receptor in the molecular chain, The depth of the charge capture site and the spatial distribution of the receptor are used to regulate the storage properties of the polyimide based storage materials. This theory provides a guiding principle for the study of the new polymer based storage materials, which combines practical research methods and many research conclusions. Development is of great significance.
【學(xué)位授予單位】：北京化工大學(xué)
【學(xué)位級(jí)別】：博士
【學(xué)位授予年份】：2017
【分類號(hào)】：O633.22
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