CN101412794B - Polymeric / carbon nano-tube composite flash memory material with side chain containing carbazole, synthetic method and use - Google Patents
Polymeric / carbon nano-tube composite flash memory material with side chain containing carbazole, synthetic method and use Download PDFInfo
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Abstract
The invention relates to a macromolecular/carbon nanotube composite flash memory material, a synthesis method thereof and application of the macromolecular/carbon nano tube composite flash memory material. The macromolecular/carbon nanotube composite flash memory material the side chains of which contain carbazole is characterized in that the macromolecular/carbon nanotube composite flash memory material has a chemical structure of a general formula on the right, wherein R is a carbon nanotube, X is Cl or Br, and n is between 20 and 200. The composite flash memory material has lower cut-in voltage and higher switched current ratio.
Description
Technical field
The present invention relates to one family macromolecule/carbon nano-tube composite flash memory material and preparation method and use, can be applicable to novel material, areas of information technology.
Background technology
Material, information technology and the energy also become three big pillars of modern civilization.In new century, the storage medium and the device of the development need ultra-high speed super-high density of information technology.In the electronic product field, silicon remains important semiconductor material at present, playing the part of almost irreplaceable role, but its cost is higher, and along with the development of semi-conductor industry, silicon industry is faced with the difficult problem of impassable nanometer.And organic polymer material have inorganicss such as many silicon the advantage that can't replace, for example: density is little, and is in light weight, is difficult for oxidation, cost is low, is easy to machine-shaping or the like.In recent years, along with the research of polymer at aspect of performances such as photoelectromagnetisms constantly makes progress, macromolecular material is also more and more wider in the range of application of photoelectron product scope.Utilized at present novel macromolecular material to produce the electron device that to make of silicon materials usually before a lot of, wherein photodiode has been used for the scale operation of flat-panel monitor, and the research of photovoltaic cell and field-effect transistor also accomplishes tangible results etc.
Some electroactive polymer novel material can change the state in current carrier (electronics or hole) under extra electric field, thereby can canned data.If use these electroactive polymer novel materials to make device, just might read the information that is stored in above it, these materials are exactly the polymer flash memory material.Therefore it is expected to be used for making the electronic component of high integration, as ultra-high speed switching element and ultrahigh density storage device etc.For the organic polymer information recording device, according to the storage behavior of device, can be divided into and can wipe rewriting type, Write once and read is several types such as type and dynamic random read-write type repeatedly.Generally speaking, storage effect is relevant with charge storage (comprising electric charge capture, charge separation or charge transfer etc.) in the organic polymer layer active group.But because polymer self, charge transfer is not very desirable, at present for the polymer information recording device, still is in the exploratory stage.
As everyone knows, carbon nanotube has excellent mechanical property and electric property.Carbon nanotube is added in the polymer, can significantly improve the multinomial performance of macromolecular material.Compare with the blend method of routine, copolymerization method, particularly controllable polymerization method can allow polymer and carbon nanotube realize combining closely on the microcosmic level, and can realize the controlled of molecular weight polymeric, molecular weight distribution and molecular structure.At present, controllable polymerization method has been applied to the graft copolymerization of vinylbenzene, methyl acrylate and methyl methacrylate etc. and carbon nanotube.
Summary of the invention
The object of the present invention is to provide a kind of side chain to contain the polymeric/carbon nano-tube composite flash memory material and the preparation method and use of carbazole, this composite flash memory material has lower cut-in voltage and high switch current ratio.
To achieve these goals, technical scheme of the present invention is: side chain contains the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that it has the chemical structure of following general formula:
Wherein R is a carbon nanotube; X is Cl or Br; N=20-200.
Described carbon nanotube is multi-walled carbon nano-tubes or Single Walled Carbon Nanotube.
Above-mentioned side chain contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that it comprises the steps:
1) press carbon nanotube: strong acid=10g:100-200mL, choose carbon nanometer tube material and strong acid, use strong acid at 80-90 ℃ of reflow treatment 12-24h carbon nanometer tube material, the filtering and washing drying obtains the acidifying carbon nanotube;
2) set by step 1) the acidifying carbon nanotube that obtains: thionyl chloride=7.1g:200-300mL chooses thionyl chloride, adds thionyl chloride in the acidifying carbon nanotube, and at 60-70 ℃ of reaction 12-24h, the filtering and washing drying obtains acylated carbon nano-tube;
3) set by step 2) acylated carbon nano-tube that obtains: quadrol=6.9g:100-150mL chooses quadrol, adds quadrol in the acylated carbon nano-tube, and at 100-120 ℃ of reaction 36-48h, the filtering and washing drying obtains the carbon nanotube that the surface has amido;
4) at first set by step 3) surface that obtains has the carbon nanotube of amido: 2-bromine isobutyl acylbromide: trichloromethane (chloroform)=5.6g:4-6g:80-100mL, choose 2-bromine isobutyl acylbromide and trichloromethane, 2-bromine isobutyl acylbromide is dispersed in the trichloromethane, obtains containing the chloroformic solution of 2-bromine isobutyl acylbromide;
Then set by step 3) surface that obtains has the carbon nanotube of amido: triethylamine: trichloromethane=5.6g:3-4.2g:100-150mL, choose triethylamine and trichloromethane, and the carbon nanotube, the triethylamine that the surface are had amido are dispersed in the trichloromethane; Add the chloroformic solution that contains 2-bromine isobutyl acylbromide under the vigorous stirring, react 36-48h down at 0 ℃-20 ℃, (obtain having the group that causes the atom transferred free radical reaction) after the filtering and washing drying, get the carbon nanotube of surperficial band initiating group in carbon nano tube surface;
5) side chain contain carbazole vinyl monomer (preparation of 9-(2-(4-vinyl (phenoxy group) ethyl)-9-carbazole):
Press 9H-carbazole-9-ethanol: sodium hydride: p-chloromethyl styrene: tetrahydrofuran (THF): diethyl ether=20-30mmol:30-50mmol:20-30mmol:50-80mL:25-40mL, choose 9H-carbazole-9-ethanol, sodium hydride, p-chloromethyl styrene, tetrahydrofuran (THF) and diethyl ether;
Earlier 9H-carbazole-9-ethanol and sodium hydride are dissolved in the exsiccant tetrahydrofuran (THF), add p-chloromethyl styrene again, at 50-60 ℃ of nitrogen protection reaction 12-24h; Reaction finishes back evaporate to dryness tetrahydrofuran (THF), gets thick product; With diethyl ether thick product is carried out recrystallization purifying, get the vinyl monomer that side chain contains carbazole;
6) by the surperficial carbon nanotube of being with initiating group: solvent: catalyzer: anti-activator: part: side chain contains the vinyl monomer of carbazole: methyl alcohol=1g:5-15mL:2-6mg:0.6-1.5mg:0.14-0.45mmol:0.3-0.8g:80-100m L, and carbon nanotube, solvent, catalyzer, anti-activator, part, the side chain of choosing surface band initiating group contain the vinyl monomer and the methyl alcohol of carbazole;
The surface is dispersed in (solvent is contained in the flask) in the solvent with the carbon nanotube of initiating group, under the argon gas atmosphere condition, add catalyzer, anti-activator, part and side chain respectively and contain the vinyl monomer (VBEC) of carbazole, continue to feed argon gas 20-30min, reacted 6-120 hour down at 60-100 ℃; Add the methyl alcohol stopped reaction then, suction filtration washs with chloroform, vacuum-drying under the room temperature, and the side chain that obtains black contains the polymeric/carbon nano-tube composite flash memory material of carbazole.
Described strong acid is the vitriol oil or concentrated nitric acid.
Described solvent is methylene dichloride, toluene or Nitromethane 99Min..
Described catalyzer is cuprous chloride or cuprous bromide;
Described anti-activator is cupric chloride or cupric bromide;
Described part is bipyridine, pentamethyl-diethyl triamine (PMDETA) or hexamethyl triethyl tetramine (HMTETA).
Above-mentioned side chain contains the application of the polymeric/carbon nano-tube composite flash memory material of carbazole: the polymeric/carbon nano-tube composite flash memory material that side chain contains carbazole has fabulous solvability, is easy to film forming, is used for information recording device as flash memory material.
Vigorous stirring is meant that the agitator motor rotating speed is 1000～3000 rev/mins.
The invention has the beneficial effects as follows (comparing) with the high molecular memory device that only uses side chain to contain carbazole:
1, carbon nanometer tube material is treated to the carbon nanotube of surface band initiating group, utilize initiating group to make side chain contain the vinyl monomer of carbazole at the carbon nano tube surface controllable polymerization, improve the distribution of carbon nanotube in polymer, improved both micro compatibilities.
2, side chain of the present invention contains the polymeric/carbon nano-tube composite flash memory material of carbazole, have good solubility, be easy to film forming, the side chain that had both contained storage effect contains the polymer of carbazole, simultaneously because the introducing of carbon nanotube absorbs volumetric shrinkage and the expansion of macromolecular material under electric field, and the high conductivity of carbon nanotube reduces the resistance of mixture, thereby obviously reduce the cut-in voltage of polymer memory device, and improve switch current ratio, improved the over-all properties of memory device.These performances can contain the adjustment of macromolecular structure of carbazole and the change of each component unit content is regulated by side chain in the composite flash memory material in addition, in the information recording device field important application prospects are arranged.
Contain the performance test experiment of memory device of the polymeric/carbon nano-tube composite flash memory material of carbazole based on side chain: get the 2mg composite flash memory material and be dissolved in the 20ml toluene, spin-coating is on glass in electroconductive ITO.Then on this ito glass evaporation metal aluminium as the top electrode of memory device.Measure the cut-in voltage and the switch current ratio of device.The result shows with the high molecular memory device that only uses side chain to contain carbazole and compares that this device has lower stable cut-in voltage and high switch current ratio.
Embodiment
For a better understanding of the present invention, further illustrate content of the present invention, but content of the present invention not only is confined to the following examples below in conjunction with embodiment.
Embodiment 1:
Side chain contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, and it comprises the steps:
1) 10g multi-walled carbon nano-tubes raw material is used the acid of the 100mL vitriol oil at 80 ℃ of reflow treatment 24h, suction filtration obtains acidifying carbon nanotube 7.1g with the deionized water wash drying;
2) add the 200mL thionyl chloride in the 7.1g acidifying carbon nanotube, at 70 ℃ of reaction 24h, suction filtration washs with tetrahydrofuran (THF), and drying obtains acylated carbon nano-tube 6.9g;
3) 6.9g acylated carbon nano-tube and 150mL quadrol are at 100 ℃ of reaction 48h, and suction filtration washs with tetrahydrofuran (THF), and the washing drying obtains the carbon nanotube 5.6g that the surface has amido;
4) carbon nanotube 5.6g, the triethylamine 4.2g (23.38mmol) that the surface is had an amido is dispersed in the 150mL trichloromethane (chloroform), the 80mL chloroform that will contain 5.32g (23.38mmol) 2-bromine isobutyl acylbromide under the vigorous stirring is added drop-wise in the above-mentioned system, at room temperature (0 ℃-20 ℃) react 48h, suction filtration washs with chloroform, obtains the carbon nanotube 5.5g of surface band initiating group after the drying;
5) side chain contains the vinyl monomer (preparation of 9-(2-(4-vinyl (phenoxy group) ethyl)-9-carbazole): earlier the 9H-carbazole-9-ethanol of 25mmol and the sodium hydride of 42mmol are dissolved in the tetrahydrofuran (THF) of exsiccant 70mL of carbazole, again to the p-chloromethyl styrene that wherein adds 27.5mmol, at 60 ℃ of nitrogen protection reaction 24h; Reaction finishes back evaporate to dryness tetrahydrofuran (THF), and thick product carries out recrystallization purifying with the 30mL diethyl ether; Get the vinyl monomer that side chain contains carbazole;
6) the carbon nanotube 1g with above-mentioned surface band initiating group is dispersed in the flask that 10mL toluene is housed, adding catalyzer cuprous chloride 4mg (0.05mmol), anti-activator cupric chloride 1mg (0.007mmol), part pentamethyl-diethyl triamine (PMDETA) 50 μ L (0.24mmol), side chain in argon gas atmosphere respectively contains the vinyl monomer of carbazole (9-(2-(4-vinyl (phenoxy group) ethyl)-9-carbazole) is 0.5g (1.53mmol) (VBEC), continue to feed argon gas 30min, reacted 70 hours down at 100 ℃; Add 100mL methyl alcohol stopped reaction, suction filtration washs with chloroform, vacuum-drying under the room temperature, the side chain that obtains black contains the polymeric/carbon nano-tube composite flash memory material 1.31g of carbazole, be equivalent to carbon nanotube graft copolymerization rate be 62%.
Above-mentioned side chain contains the application of the polymeric/carbon nano-tube composite flash memory material of carbazole: the polymeric/carbon nano-tube composite flash memory material that side chain contains carbazole has fabulous solvability, is easy to film forming, is used for information recording device as flash memory material.
Vigorous stirring is meant that the agitator motor rotating speed is 1000～3000 rev/mins.
Embodiment 2:
Methylene chloride is substituted toluene, and other is with embodiment 1, the composite flash memory material 1.28g of black, be equivalent to carbon nanotube graft copolymerization rate be 56%.
Embodiment 3:
The solvent Nitromethane 99Min. is substituted toluene, and other is with embodiment 1, the composite flash memory material 1.24g of black, be equivalent to carbon nanotube graft copolymerization rate be 48%.
Embodiment 4:
The part bipyridine is substituted pentamethyl-diethyl triamine (PMDETA), and promptly consumption is 40mg (0.24mmol), and other is with embodiment 1, the composite flash memory material 1.18g of black, be equivalent to carbon nanotube graft copolymerization rate be 36%.
Embodiment 5:
Part hexamethyl triethyl tetramine (HMTETA) is substituted pentamethyl-diethyl triamine (PMDETA), be that consumption is 66.2 μ L (0.24mmol), other is with embodiment 1, the composite flash memory material 1.29g of black, be equivalent to carbon nanotube graft copolymerization rate be 58%.
Embodiment 6:
The step 6) reaction times is replaced by 6 hours, and other is with embodiment 1, the composite flash memory material 1.06g of black, be equivalent to carbon nanotube graft copolymerization rate be 12%.
Embodiment 7:
The step 6) reaction times is replaced by 120 hours, and other is with embodiment 1, the composite flash memory material 1.40g of black, be equivalent to carbon nanotube graft copolymerization rate be 80%.
Embodiment 8:
Step 6) copolyreaction temperature is replaced by 60 ℃, and other is with embodiment 1, the composite flash memory material 1.10g of black, be equivalent to carbon nanotube graft copolymerization rate be 20%.
Embodiment 9:
Step 6) copolyreaction temperature is replaced by 80 ℃, and other is with embodiment 1, the composite flash memory material 1.26g of black, be equivalent to carbon nanotube graft copolymerization rate be 52%.
Embodiment 10:
Single Walled Carbon Nanotube is substituted multi-walled carbon nano-tubes, and other is with embodiment 1, the composite flash memory material 1.32g of black, be equivalent to carbon nanotube graft copolymerization rate be 64%.
Embodiment 11:
The part consumption is brought up to 80 μ L (0.384mmol), and other is with embodiment 1, the composite flash memory material 1.30g of black, be equivalent to carbon nanotube graft copolymerization rate be 60%.
Embodiment 12:
The part consumption is reduced to 30 μ L (0.144mmol), and other is with embodiment 1, the composite flash memory material 1.24g of black, be equivalent to carbon nanotube graft copolymerization rate be 48%.
Embodiment 13:
Vinyl monomer (VBEC) consumption that side chain is contained carbazole is brought up to 0.7g (2.142mmol), and other is with embodiment 1, the composite flash memory material 1.49g of black, be equivalent to carbon nanotube graft copolymerization rate be 70%.
Embodiment 14:
Vinyl monomer (VBEC) consumption that side chain is contained carbazole reduces to 0.3g (0.918mmol), and other is with embodiment 1, the composite flash memory material 1.14 of black, be equivalent to carbon nanotube graft copolymerization rate be 47%.
Embodiment 15:
The anti-activator cupric chloride is brought up to 1.43mg (0.01mmol), and other is with embodiment 1, the composite flash memory material 1.29g of black, be equivalent to carbon nanotube graft copolymerization rate be 58%.
Embodiment 16:
The anti-activator cupric chloride is reduced to 0.72mg (0.005mmol), and other is with embodiment 1, the composite flash memory material 1.32g of black, be equivalent to carbon nanotube graft copolymerization rate be 64%.
Embodiment 17:
Catalyzer cuprous chloride consumption is brought up to 6mg (0.75mmol), other monomeric charge when reaction conditions and treatment step with embodiment 1, the composite flash memory material 1.34g of black, be equivalent to carbon nanotube graft copolymerization rate be 68%.
Embodiment 18:
Catalyzer cuprous chloride consumption is reduced to 2mg (0.25mmol), and other is with embodiment 1, the composite flash memory material 1.23g of black, be equivalent to carbon nanotube graft copolymerization rate be 46%.
Embodiment 19:
Catalyzer cuprous bromide and anti-activator cupric bromide are substituted cuprous chloride and cupric chloride respectively, be that the two consumption is respectively 7.17mg (0.05mol) and 1.56mg (0.007mol), other is with embodiment 1, the composite flash memory material 1.28g of black, be equivalent to carbon nanotube graft copolymerization rate be 56%.
Embodiment 20:
Catalyzer cuprous bromide, anti-activator cupric bromide and part bipyridine are substituted cuprous chloride, cupric chloride and pentamethyl-diethyl triamine (PMDETA) respectively, be that three's consumption is respectively 7.17mg (0.05mol), 1.56mg (0.007mol) and 40mg (0.24mmol), other is with embodiment 1, the composite flash memory material 1.25g of black, be equivalent to carbon nanotube graft copolymerization rate be 50%.
Embodiment 21:
Catalyzer cuprous bromide, anti-activator cupric bromide and hexamethyl triethyl tetramine (HMTETA) are substituted cuprous chloride, cupric chloride and pentamethyl-diethyl triamine (PMDETA) respectively, be that three's consumption is respectively 7.17mg (0.05mol), 1.56mg (0.007mol) and 66.2 μ L (0.24mmol), other is with embodiment 1, the composite flash memory material 1.30g of black, be equivalent to carbon nanotube graft copolymerization rate be 60%.
Get the polymeric/carbon nano-tube composite flash memory material that side chain that embodiment 1 makes contains carbazole, the preparation memory device also carries out the performance test experiment: get the polymeric/carbon nano-tube composite flash memory material that the 2mg side chain contains carbazole and be dissolved in the 20ml toluene, spin-coating is on glass in electroconductive ITO, then on this ito glass evaporation metal aluminium as the top electrode of memory device.The cut-in voltage of measuring device is 1.5V and switch current ratio 10
6, and only use the cut-in voltage that side chain contains the high molecular memory device of carbazole to be 2.1V and switch current ratio 10
4, the result shows that this device has lower stable cut-in voltage and high switch current ratio.
Each cited raw material of the present invention can both be realized the present invention, and the bound value of each raw material, interval value can both realize the present invention; Do not enumerate embodiment one by one at this.Bound value, the interval value of processing parameter of the present invention (as temperature, time etc.) can both be realized the present invention, do not enumerate embodiment one by one at this.
Claims (8)
1. side chain contains the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that it has the chemical structure of following general formula:
Wherein R is a carbon nanotube; X is Cl or Br; N=20-200.
2. side chain according to claim 1 contains the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that: described carbon nanotube is multi-walled carbon nano-tubes or Single Walled Carbon Nanotube.
3. side chain as claimed in claim 1 contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that it comprises the steps:
1) press carbon nanotube: strong acid=10g: 100-200mL, choose carbon nanometer tube material and strong acid, use strong acid at 80-90 ℃ of reflow treatment 12-24h carbon nanometer tube material, the filtering and washing drying obtains the acidifying carbon nanotube;
2) set by step 1) the acidifying carbon nanotube that obtains: thionyl chloride=7.1g: 200-300mL, choose thionyl chloride, add thionyl chloride in the acidifying carbon nanotube, at 60-70 ℃ of reaction 12-24h, the filtering and washing drying obtains acylated carbon nano-tube;
3) the set by step 2) acylated carbon nano-tube that obtains: quadrol=6.9g: 100-150mL, choose quadrol, add quadrol in the acylated carbon nano-tube, at 100-120 ℃ of reaction 36-48h, the filtering and washing drying obtains the carbon nanotube that the surface has amido;
4) at first set by step 3) surface that obtains has the carbon nanotube of amido: 2-bromine isobutyl acylbromide: trichloromethane=5.6g: 4-6g: 80-100mL, choose 2-bromine isobutyl acylbromide and trichloromethane, 2-bromine isobutyl acylbromide is dispersed in the trichloromethane, obtains containing the chloroformic solution of 2-bromine isobutyl acylbromide;
Then set by step 3) surface that obtains has the carbon nanotube of amido: triethylamine: trichloromethane=5.6g: 3-4.2g: 100-150mL, choose triethylamine and trichloromethane, and the carbon nanotube, the triethylamine that the surface are had amido are dispersed in the trichloromethane; Add the chloroformic solution that contains 2-bromine isobutyl acylbromide under the vigorous stirring, react 36-48h down, after the filtering and washing drying, get the carbon nanotube of surperficial band initiating group at 0 ℃-20 ℃;
5) side chain contains the preparation of the vinyl monomer of carbazole:
Press 9H-carbazole-9-ethanol: sodium hydride: p-chloromethyl styrene: tetrahydrofuran (THF): diethyl ether=20-30mmol: 30-50mmol: 20-30mmol: 50-80mL: 25mL-40mL, choose 9H-carbazole-9-ethanol, sodium hydride, p-chloromethyl styrene, tetrahydrofuran (THF) and diethyl ether;
Earlier 9H-carbazole-9-ethanol and sodium hydride are dissolved in the exsiccant tetrahydrofuran (THF), add p-chloromethyl styrene again, at 50-60 ℃ of nitrogen protection reaction 12-24h; Reaction finishes back evaporate to dryness tetrahydrofuran (THF), gets thick product; With diethyl ether thick product is carried out recrystallization purifying, get the vinyl monomer that side chain contains carbazole;
6) by the surperficial carbon nanotube of being with initiating group: solvent: catalyzer: anti-activator: part: side chain contains the vinyl monomer of carbazole: methyl alcohol=1g: 5-15mL: 2-6mg: 0.6-1.5mg: 0.14-0.45mmol: 0.3-0.8g: 80-100mL, and carbon nanotube, solvent, catalyzer, anti-activator, part, the side chain of choosing surface band initiating group contain the vinyl monomer and the methyl alcohol of carbazole;
Described anti-activator is cupric chloride or cupric bromide;
The carbon nanotube of surface with initiating group is dispersed in the solvent, under the argon gas atmosphere condition, adds the vinyl monomer that catalyzer, anti-activator, part and side chain contain carbazole respectively, continue to feed argon gas 20-30min, reacted 6-120 hour down at 60-100 ℃; Add the methyl alcohol stopped reaction then, suction filtration washs with chloroform, vacuum-drying under the room temperature, and the side chain that obtains black contains the polymeric/carbon nano-tube composite flash memory material of carbazole.
4. side chain according to claim 3 contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that: described strong acid is the vitriol oil or concentrated nitric acid.
5. side chain according to claim 3 contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that: described solvent is methylene dichloride, toluene or Nitromethane 99Min..
6. side chain according to claim 3 contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that: described catalyzer is cuprous chloride or cuprous bromide.
7. side chain according to claim 3 contains the synthetic method of the polymeric/carbon nano-tube composite flash memory material of carbazole, it is characterized in that: described part is bipyridine, five methyl diethylentriamine or 1,1,4,7,10,10-hexamethyl Triethylenetetramine (TETA).
8. side chain as claimed in claim 1 contains the application of the polymeric/carbon nano-tube composite flash memory material of carbazole: the polymeric/carbon nano-tube composite flash memory material that side chain contains carbazole is used for information recording device as flash memory material.
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