CN101665678B - Electric tristable material, and preparation and application thereof - Google Patents
Electric tristable material, and preparation and application thereof Download PDFInfo
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Abstract
The invention relates to an electric storage material, in particular to an electric tristable material, and preparation and application thereof. The chemical structural formula of the electric tristable material is displayed in the specification, wherein R is selected from one of halogen group, nitro group or methoxyl group; and R1 is selected from one of C1-C6 alkyl group or phenyl group. Due to the application of the electric tristable material, a 3-digit data storage device is successfully manufactured. Meanwhile, the organic material of the invention has the advantages of simple synthesis, mature manufacturing process of devices and stable device performance; and the data storage capacity in unit density can grow exponentially as compared with the storage devices based on 0 and 1. Therefore, the electric tristable material has great value in the application of super-high density data storage in the next generation.
Description
Technical field
The present invention relates to a kind of electric storage medium, be specifically related to material of a kind of electric tristable and preparation method thereof.
Background technology
Information storage technology has successively experienced magnetic storage and two stages of optical storage, the mechanism that their can carry out information storage is respectively to utilize suitable the diamagnetism of magneticsubstance and light active material to finish the storage of " 0 " and " 1 " two bit data for the response that relates to laser, the big or small correspondence of information memory cell the size of minimum magnetic-particle and the interference wavelength of optical signal.Since magnetic-particle is less be subjected to the larger and optical wavelength of the impact of external magnetic field environment fixed range so that the information storage density of material be subject to certain restrictions, the limit of the storage density that can reach at present is that three-dimensional light storage and Hologram Storage are about 1000Gbit/cm3, thereby has caused the growth of information explosion formula and the contradiction between the continuous microminiaturized demand of electron device.Therefore the information storage technology of super-high density becomes the focus of materials and devices expert research in recent years.
Device based on " electrode/organic semiconductor material/electrode " sandwich structure is the research direction that potential super-high density data are stored, its principle is that device is under a continuous voltage scanning, the middle layer organic semiconductor changes the larger state of electric current (ON attitude) into by the less state of electric current (OFF attitude) moment, even this two states also can keep stable or keep relative stability under steady electric field intensity after electric field is removed, organic semiconductor with this function is called as " electric bi-stable organic semiconductor material (Organic BistableMaterials) ", and OFF and ON two states are " O " and " 1 " two states with respect to the data storage.But the device that utilizes this sandwich structure making processes and the good mechanical property of organic materials and the performance of large-area manufacturing from bottom to top, element manufacturing can be piled up the three-dimension device that final expansion is door bolt type structure as shown in Figure 1 layer by layer, comprise: substrate (1), organic film (2) and electrode (3), organic film (2) is clipped between nano level two metal electrodes (3), and each right-angled intersection point is exactly a storage unit.The realization of this stereoscopic three-dimensional memory technology will solve the traditional silicon memory device and make the storage technology complicated, that cost is expensive, two-dimentional to the problems such as restriction of storage capacity, and storage density improves 10,000 to 1,000,000 times on the basis of existing memory device.
Yet no matter magnetic storage and optical storage, or the above-mentioned electricity storage based on the organic bistable material of mentioning, up to the present all be the two bit data storage based on " 0 " and " 1 ".American scientist A Jiawo in 2008 takes the lead in having reported that at " nanometer news flash " magazine a kind of inorganic nanowires can realize three kinds of phase change of crystalline state, amorphous state and intermediates under power on condition, namely with respect to three storages of " 0 ", " 1 " and " 2 " in the data storage.Various countries scientists' great interest appears namely having caused in this report one, everybody generally acknowledges that this three bit data storage based on " 0 ", " 1 " and " 2 " or even long numeric data storage will be target and the research cores of Ultrahigh-Density Data Storage technology pursue of future generation, and its data storage capacity under equal area is compared two bit data memory devices will be exponential growth.Regrettably this material that can realize the long numeric data memory function lacking very, can't realize based on present testing method in other words; And how the element manufacturing of the material realization feasibility with long numeric data memory function, for its potential application indicates exercisable process orientation, it is a difficult problem that needs to be resolved hurrily at present, although above-mentioned nano wire can realize the variation of three kinds of phase places by making alive and then realize three storages, it is from realizing element manufacturing truly and using also very remote.
Summary of the invention
The object of the invention provides a kind of electric tristable material.
For achieving the above object, the concrete technical scheme of the present invention is, a kind of electric tristable material, and the chemical structural formula of described electric tristable material is as follows:
In the formula, described R is selected from:
A kind of in halogen, nitro or the methoxyl group; Wherein, R
1Be selected from: a kind of in the alkyl or phenyl of C1～C6.
Described electric tristable material belongs to the tetrazo sulfobenzide compounds with symmetrical structure.
Prepare the method for above-mentioned electric tristable material, may further comprise the steps:
(1) take DMF and water as mixed solvent, under 0～10 ℃, carries out the diazotization reaction of DDS, obtain the diazonium salt solution of DDS;
The chemical structural formula of the diazonium salt of described DDS is:
(2) use the diazonium salt pair of the DDS that step (1) obtains
Carry out electrophilic substitution reaction, obtain described electric tristable material.
In the actual mechanical process, prepare the method for above-mentioned electric tristable material, specifically may further comprise the steps:
(1) according to the diazotization reaction of routine, with reactant 4,4 '-diaminodiphenylsulfone(DDS), solvent N, dinethylformamide and acid mix, and mixing solutions placed the ice bath environment, slowly drip frozen water solution and the stirring of Sodium Nitrite, filter after the solution clarification, the gained diazonium salt solution cools off preservation in the ice bath atmosphere;
Wherein, a kind of in diazotization reaction commonly used hydrochloric acid, sulfuric acid or the formic acid selected in described acid;
(2) configure 0.5～2mol/L's
N, dinethylformamide solution, at 0～10 ℃, slowly be added drop-wise in the diazonium salt solution in the step (1), react the pH value to 5 of regulator solution after 0.5～2 hour～7, continue to stir after Precipitation is arranged, filter, the oven dry filter cake, the gained crude product obtains described electric tristable material through recrystallization.
Use the method that the electric tristable material prepares three bit data memory devices, may further comprise the steps:
(1) at the above-mentioned electric tristable material of the upper deposition of nano indium tin metal conductive oxide glass (ITO, In dium Tin Oxides), obtains one deck organic film;
(2) vacuum moulding machine one deck aluminium electrode on organic film is again made the sandwich structure device of " electrode/organic film/electrode ".
Prove that by voltage sweep above-mentioned sandwich structure device has three kinds of states of OFF, ON1 and ON2, i.e. proof: electric tristable material of the present invention can be for the preparation of having " 0 ", " 1 ", and the three bit data memory devices of " 2 ".
Because technique scheme is used, the present invention compared with prior art has following advantages:
Because the application of electric tristable material of the present invention, the present invention successfully makes three bit data memory devices, simultaneously, organic materials related among the present invention is synthetic simple, device performance is stable, memory data output in unit intensity will than being exponential growth based on " 0 " and " 1 " two bit data, therefore have huge value in follow-on super-high density data-storage applications.
Description of drawings
Fig. 1. the three-dimension device schematic diagram of door bolt type structure in the prior art;
Fig. 2. sandwich structure device schematic diagram among the embodiment three;
Fig. 3. the graphic representation of the current-voltage of electric tristable device among the embodiment three;
Fig. 4. among the embodiment three the electric tristable device current under constant voltage to the stability diagram of time;
Fig. 5. the schematic diagram that three storages of device data are stored and read among the embodiment three;
Wherein, 1. substrate; 2. organic film; 3. electrode; 4. aluminium electrode; 5. organic film; 6.ITO glass.
Embodiment
The invention will be further described below in conjunction with drawings and Examples:
Embodiment one
A kind of tetrazo sulfobenzide compound with symmetrical structure synthetic, its general formula is:
When R1 was methyl, its synthesis step was as follows:
(1). take by weighing 4 of 5mmol, 4 '-dimethylamino sulfobenzide joins the N of 10-30mL, in the mixing solutions of the concentrated hydrochloric acid of dinethylformamide and 3-10mL and reaction system is cooled to below 10 ℃, the Sodium Nitrite frozen water solution of configuration 0.4-0.8g/mL also slowly is added drop-wise in the previous reaction system, question response liquid continues to stir 20-120 minute after becoming clarification, filter the filtrate freezing;
(2). take by weighing the N of 8-12mmol, accelerine is dissolved in the N of 5-15mL, in the dinethylformamide, gained solution slowly is added drop-wise under 10 ℃ in the diazonium salt solution of step (1), and stirring reaction 20-120 minute, the pH value of regulation system continued stirring reaction 1-5 hour behind 5-7, filter, the filter cake oven dry obtains crude product, and crude product namely gets target compound A1 behind recrystallization, and its structural formula is as follows:
A1。
Ultimate analysis measured value %:C, 65.47; H, 5.52; N, 16.30; Ultimate analysis theoretical value: C, 65.60; H, 5.51; N, 16.39;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.11 (s, 12H, CH
3).
When the R1 group is respectively ethyl, propyl group, butyl, amyl group, hexyl and phenyl, reactions steps and reactant ratio are the same, that change is reactant N in the step (2), accelerine is replaced by N accordingly, N-Diethyl Aniline, N, N-dipropyl aniline, N, N-dibutyl aniline, N, N-diamyl aniline, N, N-dihexyl aniline and triphenylamine.The gained target compound is respectively A2, A3, and A4, A5, A6 and A7, its molecular structural formula, ultimate analysis and H-NMR data are as follows respectively:
A2
Ultimate analysis measured value %:C, 67.57; H, 6.42; N, 14.60; Ultimate analysis theoretical value: C, 67.58; H, 6.38; N, 14.78;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.35 (m, 8H), 1.13 (t, 12H).
A3
Ultimate analysis measured value %:C, 69.26, H, 7.18, N, 13.39; Ultimate analysis theoretical value: C, 69.20; H, 7.10; N, 13.45;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.35 (t, 8H), 1.49 (m, 8H), 0.98 (t, 12H).
A4
Ultimate analysis measured value %:C, 70.48, H, 7.71, N, 12.40; Ultimate analysis theoretical value: C, 70.55; H, 7.70; N, 12.34;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.35 (t, 8H), 1.52 (m, 8H), 1.33 (m, 8H), 0.96 (t, 12H).
A5
Ultimate analysis measured value %:C, 71.58, H, 8.17, N, 11.46; Ultimate analysis theoretical value: C, 71.70; H, 8.21; N, 11.40;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.35 (t, 8H), 1.52 (m, 8H), 1.29 (m, 8H), 1.33 (m, 8H), 0.96 (t, 12H).
A6
Ultimate analysis measured value %:C, 72.70; H, 8.75; N, 10.47; Ultimate analysis theoretical value: C, 72.69; H, 8.64; N, 10.60;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.35 (t, 8H), 1.52 (m, 8H), 1.28-1.32 (m, 16H), 1.33 (m, 8H), 0.96 (t, 12H).
A7
Ultimate analysis measured value %:C, 75.70; H, 4.75; N, 11.04; Ultimate analysis theoretical value: C, 75.77; H, 4.77; N, 11.04;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.70 (d, 8H), 7.01 (d, 8H), 6.68 (d, 4H), 6.60 (d, 4H), 6.46 (d, 8H).
Embodiment two
A kind of tetrazo sulfobenzide compound with symmetrical structure synthetic, its general formula is:
When R was methoxyl group, its synthesis step was as follows:
(1). take by weighing 4 of 5mmol, 4 '-dimethylamino sulfobenzide joins the N of 10-30mL, in the mixing solutions of the concentrated hydrochloric acid of dinethylformamide and 3-10mL and reaction system is cooled to below 10 ℃, the Sodium Nitrite frozen water solution of configuration 0.4-0.8g/mL also slowly is added drop-wise in the previous reaction system, question response liquid continues to stir 20-120 minute after becoming clarification, filter the filtrate freezing;
(2). the anisole that takes by weighing 8-12mmol is dissolved in the N of 5-15mL, in the dinethylformamide, gained solution slowly is added drop-wise in the diazonium salt solution of step (1) under 10 ℃, stirring reaction 20-120 minute, the pH value of regulation system continued stirring reaction 1-5 hour behind 5-7, filter also the oven dry of gained filter cake is obtained crude product, crude product namely gets target compound B1 behind recrystallization, and its structural formula is as follows:
B1
Ultimate analysis measured value %:C, 64.08; H, 4.65; N, 11.44; Ultimate analysis theoretical value: C, 64.18; H, 4.56; N, 11.52;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.89 (d, 8H), 6.74 (d, 4H), 3.68 (s, 6H).
When being respectively the halogen atoms such as nitro, fluorine, chlorine, bromine, iodine when the R group, reactions steps and reactant ratio are the same, variation be that reactant anisole in the step (2) is replaced by oil of mirbane, fluorobenzene, chlorinated benzene, bromobenzene and phenyl-iodide accordingly.The gained target compound is respectively B2, B3, and B4, B5 and B6, its molecular structural formula, ultimate analysis and H-NMR data are as follows respectively:
B2
Ultimate analysis measured value %:C, 55.74; H, 3.20; N, 16.27; Ultimate analysis theoretical value: C, 55.81; H, 3.12; N, 16.27;
1H-NMR (DMSO-d
6): δ (ppm)=8.32 (d, 4H), 8.05-8.10 (d, 8H), 8.00 (d, 4H).
B3
Ultimate analysis measured value %:C, 62.35; H, 3.60; N, 12.07; Ultimate analysis theoretical value: C, 62.33; H, 3.49; N, 12.11;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.90-7.98 (d, 8H), 7.05 (d, 4H).
B4
Ultimate analysis measured value %:C, 58.15; H, 3.30; N, 11.34; Ultimate analysis theoretical value: C, 58.19; H, 3.26; N, 11.31;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.90-7.95 (d, 8H), 7.35 (d, 4H).
B5
Ultimate analysis measured value %:C, 49.40; H, 2.73; N, 9.56; Ultimate analysis theoretical value: C, 49.34; H, 2.76; N, 9.59;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.88-7.92 (d, 8H), 7.60 (d, 4H).
B6
Ultimate analysis measured value %:C, 42.43; H, 2.33; N, 8.26; Ultimate analysis theoretical value: C, 42.50; H, 2.38; N, 8.26;
1H-NMR (DMSO-d
6): δ (ppm)=8.05 (d, 4H), 7.84-7.89 (d, 8H), 7.70 (d, 4H).
Embodiment three
Store active material as example take the compound (A1) that embodiment one obtains as electricity, the electrical storage device of preparation sandwich structure, production process is as follows: ITO conductive glass (6) successively water, acetone, Virahol cleans respectively in ultrasonic wave and was placed in 5～30 minutes in the vacuum plating unit as the organic materials deposition substrate; Get 20-30 milligram compound (A1) and behind quartz crucible, be positioned in the molybdenum boat of vacuum plating unit, be evacuated to the interior pressure of coating equipment less than 3 * 10
-3Pa begins the evaporation organic molecule, controls organic thickness between 60-100nm by film thickness detector; After the organic membrane evaporation was complete, at film loam cake one many diameters being arranged was the metal mask of 0.2mm, hung a certain amount of aluminium wire at the tungsten filament of vacuum plating unit, again was evacuated to the interior vacuum tightness of coating equipment less than 8 * 10
-4Pa begins to heat the tungsten filament AM aluminum metallization, finally forms numerous aluminium spots at organic film (5), as aluminium electrode (4), become the device design sketch to see Fig. 2.
What Fig. 3 represented is to apply the current conditions that flows through device when continuous voltage scans between upper/lower electrode, apply 0 to-3V continuous voltage when choose a point at device, electric current by device-1.37V and-the more prominent of twice moment occured in 2.09V, this unit that expression is selected has OFF, three states of ON1 and ON2 (scanning 1 expression among Fig. 3).In order to prove that these three attitudes all are that stable and selected unit is not accidental, we have selected second point to carry out repeatability and stability test, at first apply lasting-1V voltage, the stability of test OFF attitude, the gained electric current represents with the A line in accompanying drawing 4 stable case of time, affected by the data hold capacity of instrument and can only test 1000 seconds, it is stable that OFF attitude electric current keeps; Next to this o'clock from 0 to-1.7V scanning, has preferably circulation ratio with first point, the for the first time prominent ON1 attitude (scanning 3 expressions among Fig. 3) that more arrives has occured in electric current when-1.40V, uses immediately-stability of 1V voltage tester ON1 attitude, and corresponding stable case represents with the B line in accompanying drawing 4; Continuation to this o'clock from 0 to-3V scanning, electric current occurs prominently more to the ON2 attitude when-2.1V, and remains on the ON1 attitude at prominent more front electric current, uses immediately-stability of 1V voltage tester ON2 attitude again, corresponding stable case represents with the C line in accompanying drawing 4.By the test to other unit on the device, proved that all this device has the stability of extraordinary circulation ratio and three states.The OFF of device, ON1 and ON2 attitude correspond in the data storage can be expressed as " 0 ", three storage attitudes of " 1 " and " 2 ", we have selected 18 points at device, with different voltage they are opened to respectively different states, usefulness-1V voltage reads their electric current, by in twos combination, obtained the represented data storage of Fig. 5 and the schematic diagram that reads, this figure sufficient proof the feasibility of this device as the storage of three bit data.Arrived the feature that ON1 attitude and ON2 attitude all can not be returned to the OFF attitude according to device current, shown that this device is a kind of WORM (write once read many times) type device.
Claims (2)
1. the application of electric tristable material in preparation three bit data storeies, the chemical structural formula of described electric tristable material is as follows:
In the formula, described R is selected from:
A kind of in halogen, nitro or the methoxyl group; Wherein, R
1Be selected from: a kind of in the alkyl or phenyl of C1～C6.
2. use the method that the electric tristable material prepares three bit data memory devices, the chemical structural formula of described electric tristable material is as follows:
In the formula, described R is selected from:
A kind of in halogen, nitro or the methoxyl group; Wherein, R
1Be selected from: a kind of in the alkyl or phenyl of C1～C6, it is characterized in that, may further comprise the steps:
(1) at the above-mentioned electric tristable material of nano indium tin metal conductive oxide deposition on glass, obtains one deck organic film;
(2) vacuum moulding machine one deck aluminium electrode on organic film is again made the sandwich structure device of " electrode/organic film/electrode ".
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| CN102437284B (en) * | 2011-12-27 | 2014-07-02 | 苏州大学 | Quanternary electrical storage material and preparation and use thereof |
| CN102936208B (en) * | 2012-11-19 | 2015-08-19 | 苏州大学 | The azo molecules three-shift electricity storage medium at diaryl ketone center and Synthesis and applications |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD226674A1 (en) * | 1984-09-03 | 1985-08-28 | Wolfen Filmfab Veb | SILVER-FREE LIGHT-SENSITIVE MATERIAL |
| CN101339974A (en) * | 2008-08-12 | 2009-01-07 | 苏州大学 | Organic polymer electronic memory and manufacturing method therefor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD226674A1 (en) * | 1984-09-03 | 1985-08-28 | Wolfen Filmfab Veb | SILVER-FREE LIGHT-SENSITIVE MATERIAL |
| CN101339974A (en) * | 2008-08-12 | 2009-01-07 | 苏州大学 | Organic polymer electronic memory and manufacturing method therefor |
Non-Patent Citations (1)
| Title |
|---|
| Jean-Michel Nunzi,Celine Fiorini,Paul Raimond,etc..optically structured plastic electro-optic devices:about the particular photoinduced migration mechanism of bis-azodyes doped into polymers.《Molecular Crystals and Liquid Crystals Science and Technology》.2001,第374卷135-138. * |
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