CN104716274A - Preparation for perylene bisimide film and application of perylene bisimide film as high-density rapid information storage material - Google Patents
Preparation for perylene bisimide film and application of perylene bisimide film as high-density rapid information storage material Download PDFInfo
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- CN104716274A CN104716274A CN201510071007.7A CN201510071007A CN104716274A CN 104716274 A CN104716274 A CN 104716274A CN 201510071007 A CN201510071007 A CN 201510071007A CN 104716274 A CN104716274 A CN 104716274A
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- H—ELECTRICITY
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- H10K19/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- H—ELECTRICITY
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Abstract
The invention relates to preparation for a perylene bisimide film and the application of the perylene bisimide film as a high-density rapid information storage material, and belongs to the technical field of organic information storage materials. According to the preparation, firstly, soluble perylene bisimide derivatives containing the electron donor and receptor structure are obtained through reaction of PTCDA replaced at the second perylene bay position and imide containing carbazole electro-donating unit monoamine; secondly, the self-assembling perylene bisimide film is prepared by relying on the pi-pi accumulation action among molecules through a steam diffusion self-assembling method. The self-assembling perylene bisimide film is applied to an active layer of an information memory device, the storage device shows excellent electric bistable state information storage behavior, the switch ratio of the storage device is higher than 104, the signal write-in voltage is only 0.8 V, the device performance is stable, and the device shows no signal attenuation after being read 108 times. In addition, the device shows extremely high response speed, and responds to the voltage immediately without any lag, the signal balance time reaches the level of 30 nanoseconds, and the device has significant use value in the high-density rapid information storage field.
Description
Technical field
The invention belongs to organic information storage material technical field, be specifically related to the preparation of Yi Zhong perylene diimide film and the application as high density snap information storage medium thereof.
Background technology
21 century take information industry as era of knowledge-driven economy of core.Along with the development of information technology and electronic equipment, traditional semi-conducting material (as silicon, germanium) has moved closer to the limit in application.Therefore, development of new material and memory technology develop into current key issue urgently to be resolved hurrily with what tackle information storage technology.
In numerous materials, the organic material with electric bi-stable becomes the hot topic of research.This is because organic molecule diverse in function, can be cut by structure and the performance of device is effectively regulated; The size of organic molecule functional unit is at nanoscale on the other hand, and the size of memory point may diminish to nanometer level in theory; In addition, compared with traditional semiconductor storage, organic memory device is easily processed, cost is low, can large area preparation, and can make the memory device of three-dimensional structure by the method for superposition, thus realizes the storage of super-high density Large Copacity information.The electric bi-stable material organic polymer-based in this field prepared larger progress.By introducing the way of electron donor and electron acceptor unit in polymer chain simultaneously, successfully obtain the Polymers information storage material with flash-type, read-only, the different storage behavior such as dynamic random storage-type and static random storage-type at present.But although the research of Polymers electricity storage medium achieves greater advance at present, its performance is not very good, and main manifestations is that device yield is lower, and performance parameter deviation is large, and reappearance is undesirable.Trace it to its cause mainly due to the internal morphology of material with phase is uneven uncontrollablely causes.Therefore, prepare the Organic Electricity information storage material that tactical rule is orderly, stable performance is controlled to be significant.
Perylene diimide is the compound containing special condensed cyclic structure in molecule structure, has the structure of multiple derivative.Perylene diimide compounds has good photo-thermal and chemical stability, the feature that visible region strong Absorption and fluorescence quantum yield is high on the one hand; Due to it, there is very large common phenyl ring plane and π-pi-conjugated electron system on the other hand, thus there is very high electronics nucleophilic gesture and the very strong high electric transmission efficiency obtaining electronic capability and bring thus.The research of Guan Yu perylene diimide in recent years relates to molecule aggregate field in a large number, and its large π-pi-conjugated electron system and its imine nitrogen atom are with the feature that various functional group can be modified in position, perylene core bay becomes the good unit constructing functional supermolecule and macromolecular system.At present, this material achieves good result in the application in the fields such as organic solar batteries, field-effect transistor and biological fluorescent labeling, has particularly prepared the N-shaped material that current organic optoelectronic field is best.But such material is also not yet reported at the investigation and application in bi-stable electric organic state information storage material field.
For this reason, the present invention proposes Ji Yu perylene diimide supramolecular aggregation and prepares the thinking with excellent electric bi-stable information storage material, first Tong Guo perylene gulf position Er replaces perylenetetracarboxylic dianhydride and contains carbazole to the imidization reaction of the monoamine of electronic unit, has obtained the Ke soluble perylene diimide derivatives containing Electron donor acceptor structure.Then, by diffusion of vapor self-assembly method, rely on intermolecular pi-pi accumulation effect get perylene diimide self-assembled film.Then, this self-assembled film is used for the active layer of information recording device, prepares information recording device.
Perylene diimide self-assembled film obtained by the present invention has excellent electric bistable information memory property, memory device shows excellent electric bi-stable information and stores behavior, its on-off ratio is more than 104, signal write voltage only has 0.8V, and device performance is stable and do not show any signal attenuation after reading 108 times.In addition, device shows response speed extremely fast, and to voltage summary responses, without any delayed, the signal-balanced time reaches the level of 30 nanoseconds, has a extensive future in high density snap information field of storage.Gai perylene diimide film of ， is owing to being formed by self assembly compared with traditional thin polymer film active layer obtained by spin-coating method, and therefore its structure is more in order regular, and performance is more stable.The orderly accumulation of Te other Shi perylene diimide molecule is that the transmission of electric charge provides passage, and being therefore active layer with this material, memory device signal response speed is faster.The present invention is that organic information storage material field provides new material.
Summary of the invention
The object of the invention is to prepare Yi Zhong perylene diimide film and use it for high density snap information storage medium field.Perylene diimide self-assembled film provided by the present invention may be used for the active layer of information recording device, the memory device prepared shows excellent electric bi-stable information and stores behavior, switching voltage is low, fast response time, without any delayed, stable long with access time, relative to traditional thin polymer film active layer obtained by spin-coating method, its structure is more regular in order, performance is more stable, has important use value in high density snap information field of storage.
Of the present invention containing electronics give-chemical constitution of receptor structure perylene diimide compound is as follows:
This film provided by the present invention is obtained by solution vapor diffusion self-assembly method, and thickness is 30 ~ 80nm, and its preparation process is as follows:
Perylene diimide is dissolved in good solvent by A:, and being mixed with finite concentration is 1 × 10
-5~ 1 × 10
-3the solution of M, adoptable good solvent comprises chloroform, carrene, dimethyl sulfoxide (DMSO) etc.;
B: the solution prepared in steps A is dropped on clean substrate, substrate can be silicon chip, mica sheet, the directed cracking graphite flake of high temperature and electro-conductive glass (ITO);
C: be then placed in specific solvent steam atmosphere by the above-mentioned substrate carrying perylene diimide solution, solvent vapo(u)r can be methyl alcohol, oxolane and chloroform etc.;
D: temperature is set in a certain steady state value between 25 ~ 50 DEG C, keeps 5 ~ 60 hours, the self-assembled film of get perylene diimide processed.
Method of the present invention obtains perylene diimide film as high density snap information storage medium, and signal write voltage only has 0.8V, more energy-conservation relative to traditional memory material of polymer.Its on-off ratio is 10
4above, device performance is stablized and is read 10
8any signal attenuation is not shown after secondary.In addition, device shows response speed extremely fast, and to voltage summary responses, without any delayed, the signal-balanced time reaches the level of 30 nanoseconds, has important use value, have a extensive future in high density snap information field of storage.
Compared with existing memory material of polymer, the present invention has following beneficial effect:
(1) film that prepared by the present invention is orderly self-assembled film, and compared with the polymer disordered thin film prepared by spin-coating method, this film inner molecular structure is in order regular, and therefore when the active layer as information recording device, performance is also more stable.
(2) in the film prepared of the present invention, the orderly accumulation of functional molecular is that the transferring charge of material internal provides direct channel, thus substantially increase charge migration efficiency, therefore, the memory device being active layer with it has signal response speed faster.
(3) prepare with the present invention the memory device performance that perylene diimide film prepared for active layer to stablize, rate of finished products is high.
Accompanying drawing explanation
Fig. 1. the infrared spectrum of 1,7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride (PDA-TBP) prepared by embodiment 1;
Fig. 2. N prepared by embodiment 2, the infrared spectrum of N '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides (PDI-6Cz);
Fig. 3. N prepared by embodiment 2, the hydrogen nuclear magnetic spectrogram of N '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides (PDI-6Cz);
Fig. 4. N prepared by embodiment 3, the infrared spectrum of N '-two (2-carbazole ethyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides (PDI-2Cz);
Fig. 5. N prepared by embodiment 3, the hydrogen nuclear magnetic spectrogram of N '-two (2-carbazole ethyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides (PDI-2Cz);
Fig. 6. the uv atlas contrast of perylene acid anhydrides prepared by embodiment 1,2 and 3 and perylene diimide compound;
Fig. 7. with N, N, '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides are the current-voltage curve of the sandwich type memory device that active layer obtains;
Fig. 8. with N, N, '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides are the write-reading-erasing-write curve again of the sandwich type memory device that active layer obtains;
Fig. 9. with N, N, '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides are the operating time curve of the sandwich type memory device that active layer obtains;
Figure 10. with N, N, '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides are the reading times curve of the sandwich type memory device that active layer obtains;
Figure 11. with N, N, '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides are the voltage response curves of sandwich type memory device when 0.4V and 2V that active layer obtains.
Embodiment
Below in conjunction with specific embodiment, set forth invention further.It is noted that following examples are only in order to illustrate the present invention and and unrestricted technical scheme described in the invention.Therefore, although this specification with reference to following embodiment to present invention has been detailed description, it will be understood by those of skill in the art that and still can modify to the present invention or equivalent to replace; And all do not depart from technical scheme and the improvement thereof of the spirit and scope of the present invention, it all should be encompassed in the middle of right of the present invention.
Embodiment 1
The preparation of 1,7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride (PDA-TBP):
In 250ml there-necked flask, add 98% concentrated sulfuric acid (113ml) and 3,4,9,10-perylenetetracarboxylic dianhydride (7.272g, 18.5mmol), be warming up to 55 DEG C of magnetic agitation 16h, be warming up to 85 DEG C, add I
2start after (0.519g, 2mmol) to drip Br
2(2.1ml, 41mmol), 1h drips off, and finishes, insulation reaction 27h.Be cooled to room temperature, dropwise add water (50ml) and make the concentration of sulfuric acid be reduced to about 80%, now a large amount of solids is separated out, and sand core funnel filters, and filter cake first uses 80%H
2sO
4(70ml) wash, then be washed till neutrality with deionized water.Through acetone washing final vacuum dry dark red solid reaction intermediate.
Add in 100ml single port flask and walk product (1.012g; 1.82mmol); tert-butyl phenol (0.915g, 6mmol), potash (1.015g; 7.24mmol); dry DMF (40ml), under nitrogen protection; be heated to backflow, magnetic agitation reaction 7h.Be cooled to room temperature, poured into by mixture in 25% acetic acid (60ml), have aubergine solid to separate out, filter, filter cake washes with water to neutrality, obtains aubergine 1,7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride under vacuum environment after drying.
Productive rate 80%; Infrared (KBr compressing tablet): 3058cm
-1(phenyl ring C-H stretching vibration), 2962cm
-1(alkyl chain C-H stretching vibration), 1767 and 1737cm
-1(stretching vibration of acid anhydrides C=O key), 1595 and 1506cm
-1(stretching vibration of phenyl ring C=C key).(as shown in Figure 1)
Embodiment 2
The preparation of N, N '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides (PDI-6Cz):
1 is added in 50ml there-necked flask; 7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride (0.1374g; 0.2mmol), 6-carbazyl hexyl amine (0.5809g, 2mmol); imidazoles (0.2768g; 4mmol), dry pyridine 20ml, nitrogen protection; be heated to backflow, stirring reaction 11 hours.Be cooled to after room temperature until system after reaction terminates, product is poured into 25ml water, in the mixed solution of 30ml chloroform and 10 concentrated hydrochloric acids, repeatedly extracting organic phase with chloroform again and obtain crude product after revolve steaming after sodium acid carbonate washing, is eluent dry target product after post is separated with benzinum/carrene (2:5).
Productive rate 40%, infrared (KBr compressing tablet): 2957-2856cm
-1(alkyl chain C-H stretching vibration), 1697 and 1657cm
-1(stretching vibration of acid imide C=O key) (as shown in Figure 2), nuclear-magnetism
1h NMR (CDCl
3, 600MHz), δ (ppm): 9.59 (d, 2H, J=8.4Hz), 8.56 (d, 2H, J=8.3Hz), 8.34 (s, 2H), 8.05 (d, 4H, J=7.7Hz), 7.45 (d, 4H, J=7.7Hz), 7.42 (t, 4H, J=7.1Hz), 7.36 (d, 4H, J=8.2Hz), 7.18 (t, 4H, J=7.3Hz), 7.08 (d, 4H, J=8.7Hz), 4.28 (t, 4H, J=7.2Hz), 4.13 (t, 4H, J=7.4Hz), 1.88 (t, 4H, J=7.1Hz), 1.7 (t, 4H, J=7.0Hz), 1.45 (m, 8H), 1.369 (s, 18H). (as shown in Figure 3)
Embodiment 3
The preparation of N, N '-two (2-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides (PDI-2Cz):
1 is added in 50ml there-necked flask; 7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride (0.12g; 0.2mmol), 2-carbazyl ethylamine (0.2834g, 2mmol); imidazoles (0.2834g; 4mmol), dry pyridine 20ml, nitrogen protection; be heated to backflow, stirring reaction 12 hours.Be cooled to after room temperature until system after reaction terminates, product is poured into 25ml water, in the mixed solution of 30ml chloroform and 11 concentrated hydrochloric acids, repeatedly extracting organic phase with chloroform again and obtain crude product after revolve steaming after sodium acid carbonate washing, is eluent dry target product after post is separated with benzinum/carrene (3:5).
Productive rate 30%; Infrared (KBr compressing tablet): 2961-2865cm
-1(alkyl chain C-H stretching vibration), 1699 and 1661cm
-1(stretching vibration of acid imide C=O key) (as shown in Figure 4); Nuclear-magnetism
1h NMR (CDCl
3, 400MHz), δ (ppm): 9.67 (d, 2H, J=8.34Hz), 8.66 (d, 2H, J=8.34Hz), 8.42 (s, 2H), 8.08 (d, 4H, J=6.2Hz), 7.68 (d, 4H, J=7.49Hz), 7.519 (m, 12H), 7.00 (s, 4H), 4.64 (m, 8H), 1.4 (s, 18H). (as shown in Figure 5)
Embodiment 4
Containing electronics give-by the spectrum behavior of body structure perylene diimide compound solution:
In single good solvent, 1x10 is mixed with in chloroform respectively by 1,7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride with containing the perylene diimide compound of carbazole electron donor
-5the solution of mol/L.Analyzed reaction mixture by ultraviolet-visible spectrophotometer, result as shown in Figure 6, finds to occur perylene ring characteristic absorption peak at 400-600nm, corresponds respectively to S
0-S
2, S
0-S
1(0-0), S
0-S
1(0-1) electron transition.Because carbazole has strong electron donation, after Qi Yin Ru perylene diimide, it there occurs electric charge delocalization as electron donor Yu between perylene diimide perylene core (can be used as electron acceptor), define charge transfer complex, thus cause it band gap to reduce, spectral absorption bands of a spectrum generation red shift.The absorption spectra of PDI-2Cz molecule shows red shift more significant than PDI-6Cz, this is because the bridging in PDI-6Cz and PDI-2Cz molecule between carbazole group Yu perylene core is respectively the n-hexyl chain of 6 carbon and the ethyl chain of 2 carbon, in comparison, carbazole in PDI-2Cz molecule is Yu the distance between perylene core is nearer, therefore electric charge delocalization degree is larger, and spectral red shift is also more obvious.
Embodiment 5
With N, N '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides is that active layer has obtained the memory device of sandwich type, and hearth electrode is for mixing indium tin oxide, top electrode is gold, then carries out semiconductor parametric test to device.
To with N, N '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides is that the sandwich type memory device that active layer obtains carries out current-voltage curve test (as shown in Figure 7).In first time voltage forward scan process, electric current starts to maintain lower conductance state, has then jumped to height at about 0.8V and has led state.Voltage continues to increase, and the electric current of memory device maintains height, and to lead state constant.Carry out the scanning of second time forward voltage subsequently, find that memory device remains on height always and leads state.But negative voltage scanning is carried out to device, electric current starts to maintain higher conductance state, then suddenly jumps to lowly to lead state about-3.2V.Again carry out the voltage scanning of 0 to-4, memory device maintains always lowly leads state, shows that written information is all wiped free of.Again carry out above-mentioned scan round after power-off, memory device repeats the process write-read-wipe-again read again, and has good repeatability.According to the current-voltage curve of device, information write-read-wipe-is read again corresponding voltage and be set to 2 respectively, 0.4,4.5,-1V, the duration of every section of voltage is 2s, observes electric current with the situation of change of voltage, can obtain information write as shown in Figure 8-read-erasing-write curve again.Discuss the current on/off ratio (as shown in Figure 9) of device, long-time stability (as shown in Figure 10) and response time (as shown in figure 11) respectively simultaneously.Result shows, when operating voltage is 0.4V, with N, N, '-two (6-carbazole hexyl)-1,7-bis-(4-tert-butyl group phenoxy group)-3,4,9,10-perylene tetracarboxylic acid diimides are that the device of active layer has and is greater than 10
4on-off ratio, and stability is good, in reading 10
8any signal attenuation is not shown after secondary.Figure 11 shows, during beginning, device is in closed condition, and apply 0.4V voltage to it, device is still in closed condition.And, after the voltage of 2V (being greater than threshold voltage) is applied to it, current value becomes large instantaneously, namely device becomes open mode from closed condition, and do not observe any response time, and equilibration time is 30ns, relative to traditional semi-conducting material, there is signal response speed more fast.
Claims (4)
1. the preparation of Yi Zhong perylene diimide film and the application as high density snap information storage medium thereof, it is characterized in that the chemical composition of: perylene diimide film be containing electronics give-receptor structure perylene diimide derivative ， perylene diimide film is the self-assembled film that the solution vapor diffusion method supported by surface is formed on the substrate of cleaning.
2. according to claim 1 containing electronics give-receptor structure perylene diimide derivative, it is characterized in that, it is by adopting perylene gulf position Er to replace perylenetetracarboxylic dianhydride and obtain Qi Zhong perylene gulf of position Er containing carbazole to the imidization reaction of the monoamine of electronic unit and replace perylenetetracarboxylic dianhydride and comprise 1,7-bis-(phenoxy group) perylene tetracid dianhydride and 1,7-bis-(4-tert-butyl group phenoxy group) perylenetetracarboxylic dianhydride, comprises 2-carbazyl ethylamine, 6-carbazyl hexyl amine and 12-carbazyl lauryl amine containing carbazole to the monoamine of electronic unit.Its structure is as follows:
3., according to claim 1 Suo Shu perylene diimide film and preparation method thereof, it is characterized in that this film is obtained by solution vapor diffusion self-assembly method, thickness is 30 ~ 80nm, and its preparation process is as follows:
Perylene diimide is dissolved in good solvent by A:, and being mixed with finite concentration is 1 × 10
-5~ 1 × 10
-3the solution of M, adoptable good solvent comprises chloroform, carrene, dimethyl sulfoxide (DMSO) etc.;
B: the solution prepared in steps A is dropped on clean substrate, substrate can be silicon chip, mica sheet, the directed cracking graphite flake of high temperature and electro-conductive glass (ITO);
C: be then placed in specific solvent steam atmosphere by the above-mentioned substrate carrying perylene diimide solution, solvent vapo(u)r can be methyl alcohol, oxolane and chloroform etc.;
D: temperature is set in a certain steady state value between 25 ~ 50 DEG C, keeps 5 ~ 60 hours, the self-assembled film of get perylene diimide processed.
4. the method according to claim 1-3 obtains the application of perylene diimide film, it is characterized in that, Suo Shu perylene diimide film is as the application of high density snap information storage medium.
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| CN108767111A (en) * | 2018-06-26 | 2018-11-06 | 东莞理工学院 | Sandwich structure memory device containing polymer nanocomposite film and preparation method |
| CN108767111B (en) * | 2018-06-26 | 2022-07-05 | 东莞理工学院 | Sandwich structure memory device containing polymer nano-film and preparation method thereof |
| CN110845505A (en) * | 2019-11-18 | 2020-02-28 | 陕西理工大学 | Perylene diimide derivative, electric impedance type distinguishing and detecting pyridine derivative sensor based on perylene diimide derivative, and preparation method and application of perylene diimide derivative |
| CN110845505B (en) * | 2019-11-18 | 2022-03-29 | 陕西理工大学 | Perylene diimide derivative, electric impedance type distinguishing and detecting pyridine derivative sensor based on perylene diimide derivative, and preparation method and application of perylene diimide derivative |
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