CN105789443A - Modified polythiophene organic magnetic resistance film material, preparation method therefor and application thereof - Google Patents
Modified polythiophene organic magnetic resistance film material, preparation method therefor and application thereof Download PDFInfo
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Hall/Mr Elements (AREA)
Abstract
The invention provides an organic magnetic resistance film material. The organic magnetic resistance film material is obtained after compounding a polythiophene compound and a polycyclic aromatic hydrocarbon derivative. According to the organic magnetic resistance film material, a polycyclic aromatic hydrocarbon organic small molecular compound is mixed with a polythiophene organic high molecular polymer, so that polythiophene organic high molecules can be doped and modified. The highest occupied orbital energy level of a dopant is higher than that of a doped object, so that hole carriers are blocked by the dopant in a transmission process of the doped object to form a "carrier trap", and due to the introduction of the "carrier trap", a more sensitive magnetic resistance effect can be generated; and meanwhile the polycyclic aromatic hydrocarbon dopant has higher carrier migration rate than the polythiophene doped object, so that the introduction of the dopant further enhances the conductivity of the doped object.
Description
Technical field
The present invention relates to magnetoresistance material technical field, be specifically related to a kind of modified polythiophene class organo-magnetoresistive thin-film material and preparation method thereof, application.
Background technology
Magnetoresistance (MagnetoresistanceEffect), is also called magneto-resistance effect, refers to the phenomenon that the resistance value of some metal or quasiconductor changes with externally-applied magnetic field change.Magnetoresistance is broadly divided into normal magnetic resistance, giant magnetoresistance, super giant magnetoresistance, incorgruous magnetic resistance, tunnel magneto-resistance effect etc..In most metals, the changing value of resistivity is just, and the change in resistance value of transition metal and metalloid alloy and saturation magnets is negative, and especially quasiconductor has very big magneto-resistor anisotropy.Utilize the magneto-resistance effect of material, it is possible to make mistor element, be used for constructing displacement transducer, speed probe, position sensor and velocity sensor etc..
Along with organic semiconducting materials in the photoelectric devices such as organic electroluminescence device, photovoltaic cell and field effect transistor broad development application, especially the conjugation organic semiconductor polyfluorene of the report such as Francis in 2004 shows huge Negative magneto resistance effect, room-temperature magnetoresistance rate considerably beyond inorganic non-magnetic material so that scholars begin to focus on the organic semiconducting materials performance study in magnetic effect field.
Organic semiconductor refers to the organic functional material with characteristic of semiconductor, mainly a class comprises organic polymer and the organic molecule of 7c conjugated structure, owing to externally-applied magnetic field can change the injection current of organic semiconductor device, photoelectric current, luminescence generated by light, electroluminescent etc., this wherein organic magneto-resistor be a kind of model experiment phenomenon that organic material shows, organic semiconducting materials resistance change rate under room temperature and downfield (～10mT) is up to more than 10%.Thus the photoelectric characteristic that organic semiconductor device is under the action of a magnetic field becomes a research field received much concern in recent ten years,
Such as the organo-magnetoresistive device disclosed in Chinese patent (CN101427145B) and application thereof, (CN101427395A) apparatus and method of condition monitoring for equipment ingredient disclosed in the device with magnetoresistance disclosed in and application thereof and (CN103748477A) etc., all disclose a series of organic polymer film member with magnetoresistance, " AMR (anisotropic magnetoresistive) " effect ratio with conventional monolayers system, sensitivity improves an order of magnitude, and GMR (giant magnetoresistance) effect and TMR (tunnel magnetoresistive) effect are the main representative of these organic thin layer components.nullIn addition by " HangGu,TheoKreouzis,WilliamGillin " show，It is published in " OrganicElectronics (organic electronics) ",2014 years，15th volume，8th phase 1711-1716 page，Article " Thetransitionfrombipolarontotriplet-polaronmagnetoresist anceinasinglelayerorganicsemiconductordevice (in monolayer organic semiconductor device from biexction magnetoresistance to triplet state-exciton magnetoresistance change) " also illustrates such as polythiophene class organic polymer magnetoresistance etc..But organic polymer magnetoresistance material is in the application such as sensor disclosed in existing, however it remains the shortcoming that conductive capability is relatively poor and magnetic resistance response sensitivity is relatively low.
Thus, how to obtain a kind of organo-magnetoresistive material, it is possible to increase conductive capability in application process and magnetic resistance response sensitivity, it has also become scholar that this area is forward-looking and enterprise's extensive concern focus.
Summary of the invention
In view of this, the technical problem to be solved in the present invention is in that to provide a kind of organic polymer magnetoresistance material and its preparation method and application, especially a kind of modified polythiophene class organo-magnetoresistive thin-film material and preparation method thereof, application.Modified polythiophene class organic polymer thin film provided by the invention has higher electric conductivity, and the electronic device prepared has higher magnetic resistance responsiveness.
The invention provides a kind of organo-magnetoresistive thin-film material, obtained by after polythiophene class compound and condensed-nuclei aromatics analog derivative compound.
Preferably, described polythiophene class compound includes one or more in 3-hexyl substituting polythiophene, 3-octyl group substituting polythiophene and poly-(3-butyl polythiophene-2,5-bis-base)；
Described condensed-nuclei aromatics analog derivative includes one or more in Benzo[b five polythiophenes, 6,13-dimethyl Benzo[b and 6,13-diethyl Benzo[b.
Preferably, described condensed-nuclei aromatics analog derivative is (0.1～10) with the mass ratio of described polythiophene class compound: (99.9～90).
Preferably, the thickness of described organo-magnetoresistive thin film is 50nm～1 μm；
The carrier mobility of described organo-magnetoresistive thin film is 1 × 10-4cm2/ V s～0.1cm2/V·s。
The preparation method that the invention provides a kind of organo-magnetoresistive thin-film material, comprises the following steps:
1), after polythiophene class compound and condensed-nuclei aromatics analog derivative being mixed in organic solvent, mixed liquor is obtained；
2), after mixed liquor film forming above-mentioned steps obtained, organo-magnetoresistive thin-film material is obtained.
Preferably, described organic solvent includes o-dichlorobenzene, m-dichloro-benzenes, o-dichlorobenzene and one or more in chlorobenzene.
Preferably, the method for described film forming includes pressing, spraying process, bar type rubbing method or print process.
Preferably, described step 1) particularly as follows:
Condensed-nuclei aromatics analog derivative is dissolved in organic solvent, after adding the mixing of polythiophene class compound, obtains mixed liquor.
The invention provides the application in mistor element of the organo-magnetoresistive thin-film material described in technique scheme any one or the organo-magnetoresistive thin-film material prepared by technique scheme any one.
Present invention also offers a kind of organic electronic element, there is Rotating fields and at least two contact of at least three layers,
Described three layers is upper conductive layer, organic intermediate layer and lower conductiving layer；Wherein, described organic intermediate layer adopts the organo-magnetoresistive thin-film material described in technique scheme any one or the organo-magnetoresistive thin-film material prepared by the method described in technique scheme any one.
The invention provides a kind of organo-magnetoresistive thin-film material, obtained by after polythiophene class compound and condensed-nuclei aromatics analog derivative compound.Compared with prior art, the present invention utilizes the organic micromolecule compound of condensed-nuclei aromatics class to mix with polythiophene class organic high molecular polymer, it is achieved to polythiophene class organic polymer doping vario-property.The present invention is based on being incorporated foreign material polythiophene class organic polymer band structure and the contrast of described alloy condensed-nuclei aromatics class material band structure, the highest orbital energy level that is occupied that alloy can be with is higher than the highest track that is occupied being incorporated foreign material, therefore class carrier in hole can be incorporated foreign material stop in the transmitting procedure be incorporated foreign material, thus forming the mechanism of " carrier traps ", and the introducing of " carrier traps " can produce sensitiveer magnetoresistance；Simultaneously condensed-nuclei aromatics class alloy is incorporated foreign material than polythiophene class and has higher carrier mobility, and therefore the introducing of alloy also enhances the electric conductivity being incorporated foreign material.
Test result indicate that, the device with magnetic resistance performance prepared based on the organic composite material after doping provided by the invention, compare traditional magnetosensitive device, electronic device magnetic resistance responsiveness provided by the invention strengthens (maximum up to～5 times), conductive capability strengthens, thus it is poor to solve tradition organic polymer magnetoresistive transducer device electric conductivity, magnetic resistance response is insensitive, the uncontrollable problem of doping level.
Accompanying drawing explanation
The structure simplification figure of the rigidity organic diode electronic components with magnetoresistance that Fig. 1 provides for the embodiment of the present invention；
The structure simplification figure of the flexible organic diode electronic components with magnetoresistance that Fig. 2 provides for the embodiment of the present invention.
Detailed description of the invention
In order to further appreciate that the present invention, below in conjunction with embodiment, the preferred embodiments of the invention are described, but it is to be understood that these describe simply as to further illustrate the features and advantages of the present invention rather than the restriction to patent requirements of the present invention.
The all raw materials of the present invention, be not particularly limited its source, that commercially buy or prepare according to conventional method well known to those skilled in the art.
The all raw materials of the present invention, are not particularly limited its purity, present invention preferably employs analytical pure or the purity that magnetic-sensitive material is conventional is prepared in this area.
The invention provides a kind of organo-magnetoresistive thin-film material, obtained by after polythiophene class compound and condensed-nuclei aromatics analog derivative compound.
Organo-magnetoresistive thin-film material of the present invention and organo-magnetoresistive thin film；Described polythiophene class compound is not particularly limited by the present invention, with such high-molecular organic material with magnetoresistance well known to those skilled in the art, those skilled in the art can according to practical condition, service condition and properties of product select, polythiophene class compound of the present invention preferably includes 3-hexyl substituting polythiophene, 3-octyl group substituting polythiophene and poly-(3-butyl polythiophene-2, 5-bis-base) in one or more, it is more preferably 3-hexyl substituting polythiophene, 3-octyl group substituting polythiophene or poly-(3-butyl polythiophene-2, 5-bis-base)；Described condensed-nuclei aromatics analog derivative is not particularly limited by the present invention, with condensed-nuclei aromatics analog derivative well known to those skilled in the art or condensed-nuclei aromatics compounds, those skilled in the art can select according to practical condition, service condition and properties of product, condensed-nuclei aromatics analog derivative of the present invention preferably include Benzo[b five polythiophenes, 6,13-dimethyl Benzo[b and 6, one or more in 13-diethyl Benzo[b, be more preferably include Benzo[b five polythiophenes, 6,13-dimethyl Benzo[b or 6,13-diethyl Benzo[bs.
Concrete structure after the definition of described compound or compound is not particularly limited by the present invention, with the concept of compound well known to those skilled in the art, can be one or more in mixing, coating, cladding and doping in the present invention, and the present invention is preferably doping.The mass ratio of described condensed-nuclei aromatics analog derivative Yu described polythiophene class compound is not particularly limited by the present invention, with conventional doping ratio well known to those skilled in the art, those skilled in the art can according to practical condition, prescription and properties of product select, the present invention limits based on equipment precision, and dopant material more than 10% after, there will be organo-magnetoresistive film surface degree of roughness to increase, the problems such as Quality Down, the mass ratio of described condensed-nuclei aromatics analog derivative and described polythiophene class compound is preferably (0.1～10): (99.9～90), it is more preferably (0.5～8): (99.5～92), it is more preferably (1～7): (99～93), it most preferably is (3～6): (97～94).
Other character of described organo-magnetoresistive thin-film material are not particularly limited by the present invention, with organo-magnetoresistive thin film well known to those skilled in the art or organo-magnetoresistive material, the present invention ensures or improves the electromagnetic performance of organo-magnetoresistive thin film, the thickness of organo-magnetoresistive thin film is preferably 50nm～1 μm, it is more preferably 100nm～900nm, it is more preferably 200nm～500nm, it is most preferred that for 300nm～400nm.Difference according to preparation method, the carrier mobility of organo-magnetoresistive thin-film material of the present invention hole at room temperature and electronics, namely carrier mobility can be distributed in 1 × 10-4～0.1cm2/ V s, it is also possible to be distributed in 1 × 10-3～0.05cm2/ V s, it is also possible to be distributed in 1 × 10-4～1 × 10-3cm2/ V s or 3 × 10-4～8 × 10-4cm2Between/V s.
The present invention utilizes condensed-nuclei aromatics organic micromolecule compound (such as Benzo[b etc.) to carry out controllability ratio with polythiophene class organic high molecular polymer (such as 3-hexyl substituting polythiophene etc.) to mix, achieve polythiophene class organic macromolecule controllability doping vario-property, thus improve polythiophene class high-molecular organic material electric conductivity, and the meeting of " carrier traps " that formed produces sensitiveer magnetoresistance.
The preparation method that the invention provides a kind of organo-magnetoresistive thin-film material, comprises the following steps:
1), after polythiophene class compound and condensed-nuclei aromatics analog derivative being mixed in organic solvent, mixed liquor is obtained；
2), after mixed liquor film forming above-mentioned steps obtained, organo-magnetoresistive thin film is obtained.
The present invention is to optimum principles such as the selection of described organo-magnetoresistive thin-film material preparation process Raw and ratios, as without dated especially, with the equal one_to_one corresponding in aforementioned organo-magnetoresistive thin-film material, this is no longer going to repeat them.
The present invention obtains mixed liquor after first polythiophene class compound and condensed-nuclei aromatics analog derivative being mixed in organic solvent.
Described hybrid mode is not particularly limited by the present invention, and with hybrid mode well known to those skilled in the art, the present invention is dispersed, magneton stirring or heated and stirred preferably；The present invention is for improving mixed effect, it is also preferred that adopt ultrasonic method or microwave method to accelerate material dissolution.The equipment of described mixing is not particularly limited by the present invention, and with mixing apparatus well known to those skilled in the art, the present invention is preferably sol evenning machine.The detailed process of described mixing is not particularly limited by the present invention, those skilled in the art can select according to practical condition, mixing situation and properties of product, the present invention improves the effect of doping vario-property, condensed-nuclei aromatics analog derivative is preferably dissolved in organic solvent by described blend step, after adding the mixing of polythiophene class compound, obtain mixed liquor.
The present invention is in above-mentioned blend step, the additional proportion of described condensed-nuclei aromatics analog derivative and polythiophene class compound, those skilled in the art can according to practical condition, prescription and properties of product select, the present invention is based on equipment precision restriction and raw material dissolubility restriction in organic solvent, and dopant material more than 10% after, there will be organo-magnetoresistive film surface degree of roughness to increase, the problems such as Quality Down, the mass ratio of described condensed-nuclei aromatics analog derivative and described polythiophene class compound is preferably (0.1～10): (99.9～90), it is more preferably (0.5～8): (99.5～92), it is more preferably (1～7): (99～93), it most preferably is (3～6): (97～94).Described organic solvent is not particularly limited by the present invention, with the Organic substance for this compounds well known to those skilled in the art, present invention preferably comprises o-dichlorobenzene, m-dichloro-benzenes, one or more in o-dichlorobenzene and chlorobenzene, more preferably o-dichlorobenzene, m-dichloro-benzenes, o-dichlorobenzene or chlorobenzene, it is most preferred that for o-dichlorobenzene.The concrete consumption of described organic solvent is not particularly limited by the present invention, with the Conventional solvents consumption of this compounds of dissolving well known to those skilled in the art.
After the mixed liquor film forming that above-mentioned steps is obtained by the present invention subsequently, obtain organo-magnetoresistive thin film.Detailed process and the method for described film forming are not particularly limited by the present invention, with organic compound film build method well known to those skilled in the art and film forming procedure, such as conventional pressing, spraying process, bar type rubbing method or print process.
Present invention also offers the application in mistor element of the organo-magnetoresistive thin-film material described in technique scheme any one or the organo-magnetoresistive thin-film material prepared by technique scheme any one.
The definition of described mistor element is not particularly limited by the present invention, and with the definition of mistor element well known to those skilled in the art, mistor element of the present invention can be single device or device etc., it is also possible to for basic resistive elements；The concrete structure of described mistor element is not particularly limited by the present invention, with the structure of mistor element well known to those skilled in the art.
Present invention also offers a kind of organic electronic element, have Rotating fields and at least two contact of at least three layers, described three layers is upper conductive layer, organic intermediate layer and lower conductiving layer；Wherein, described organic intermediate layer adopts the organo-magnetoresistive thin-film material described in technique scheme any one or the organo-magnetoresistive thin-film material prepared by the method described in technique scheme any one.
Other concrete structures of described organic electronic element are not particularly limited by the present invention, with organic electronic element structure well known to those skilled in the art, concrete, described organic electronic element can be magneto-dependent sensor, and described magneto-dependent sensor has preferably included the organic film component with diode structure；
And organic film component includes Rotating fields and at least two contact with at least three layers；
Described three layers is upper conductive layer, organic intermediate layer and lower conductiving layer；Wherein, described organic intermediate layer is the organo-magnetoresistive thin-film material described in technique scheme any one or the organo-magnetoresistive thin-film material prepared by technique scheme any one.
The concrete structure of described magneto-dependent sensor is not had other to limit especially by the present invention, with the structure of magneto-dependent sensor well known to those skilled in the art；Magneto-dependent sensor of the present invention can be defined as the magneto-dependent sensor containing mistor element, it is also possible to is defined as mistor element.
Provided by the invention above-mentioned based on organo-magnetoresistive thin-film material provided by the invention, i.e. the sensor device with magnetoresistance of the organic molecule after doping vario-property/macromolecular material mixture.Wherein said sensor device preferably included have diode structure containing organo-magnetoresistive film member provided by the invention, and this electronic component structure includes at least three layers, upper and lower two conductive layers and the middle modified organic molecule/Thin Polymer Mixture Films layer with magnetoresistance.
It should be noted that under this design conditions, " layer " is not that narrow sense is referred to as independent layer, and refers to a kind of functional composition.Therefore the layer that in three-decker, upper and lower both sides can be conducted electricity, can be included the sandwich such as cushion completely or realize substituting by intermediate layer of adulterating by introducing.Each layer in three layers can supplement perfect by interpolation auxiliary layer, and the organic electronic component with magnetoresistance can exist with encapsulating, it is also possible to does not exist with not encapsulating.Those skilled in the art can be clearly understood from, and above-mentioned improvement is also in protection scope of the present invention.
The present invention is optional, and described upper and lower two conductive layers, the deposition process of conductive material includes: vacuum thermal evaporation, vaccum gas phase sedimentation method, magnetron sputtering method, plasma sputtering, spraying process, print process etc..
Optionally, to include following material at least one or several for described upper and lower two layers of conductive material: platinum, palladium, nickel, copper, titanium, gold, silver, aluminum, Graphene, the aluminum being cushion with lithium fluoride, polymer P EDOT:PSS, tin indium oxide, tin-antiomony oxide and Indium sesquioxide. tin silver/tin indium oxide；Can also be platinum, palladium, nickel, copper, titanium, gold, silver, aluminum, Graphene, polymer P EDOT:PSS, the aluminum being cushion with lithium fluoride, the tin indium oxide being cushion with zinc oxide, the tin indium oxide being cushion with titanium dioxide, tin-antiomony oxide and Indium sesquioxide. tin silver/tin indium oxide
Optionally, described electronic component structure also includes base material, and described base material can be divided into rigid basement class material and flexible substrates class material.Metal material substrate or the glass material substrates etc. such as rigid basement class material includes: copper coin, nickel plate, gold plate, iron plate.Flexible base material includes: polystyrene, polyethylene, polrvinyl chloride, politef, polyester, Merlon, polyacrylate, the substrate of plastics material such as polyimides and polyethers or paper material substrate.
Further, electronic component structure of the present invention also can be selected for being configured to the electronic component of transistor arrangement, and the structure of transistor includes the electrical contact that at least three layers is different with at least three, two layers that can conduct electricity and an organic layer.In described three layers, at least one of which is structurized layer.In this layer, structured source electrode and drain electrode, source electrode and the drain electrode of being provided with is embedded in organic layer, lays insulating barrier in lower end, embeds gate electrode in a insulating layer, is laid on the base layer by said structure.
The present invention utilizes the organic micromolecule compound of condensed-nuclei aromatics class to mix with polythiophene class organic high molecular polymer, realize polythiophene class organic polymer doping vario-property, and by the ratio adjustment of controllability, moreover it is possible to realize the controllability doping vario-property for magnetic resistance responsive materials.The present invention is by being incorporated foreign material polythiophene class organic polymer band structure and the contrast of described alloy condensed-nuclei aromatics class material band structure, the highest orbital energy level that is occupied that alloy can be with is higher than the highest track that is occupied being incorporated foreign material, therefore class carrier in hole can be incorporated foreign material stop in the transmitting procedure be incorporated foreign material, thus forming " carrier traps ", the introducing of " carrier traps " can produce more sensitive magnetic inhibition effect, it is achieved that based on the magnetic resistance response sensitivity of the magnetically sensitive device of doping vario-property material；Simultaneously condensed-nuclei aromatics class alloy is incorporated foreign material than polythiophene class and has higher carrier mobility, thus the introducing of alloy enhances the electric conductivity being incorporated foreign material, it is achieved that the modified electric conductivity of magnetic resistance responsive materials promotes.
Test result indicate that, the device with magnetic resistance performance prepared based on the organic composite material after doping provided by the invention, compare traditional magnetosensitive device, electronic device magnetic resistance responsiveness provided by the invention strengthens (maximum up to～5 times), conductive capability strengthens, thus it is poor to solve tradition organic polymer magnetoresistive transducer device electric conductivity, magnetic resistance response is insensitive, the uncontrollable problem of doping level.
In order to be further appreciated by the present invention, below in conjunction with embodiment, a kind of modified polythiophene class organo-magnetoresistive thin-film material provided by the invention and preparation method thereof, application being illustrated, protection scope of the present invention is not limited by the following examples.
Embodiment 1
Prepare Benzo[b/3-hexyl substituting polythiophene compound organic film
First, setting the doping ratio of 1%, the mixed solution concentration of preparation is set as 30 mg/ml, is 29.7 milligrams by containing 3-hexyl substituting polythiophene in calculating acquisition 1 ml soln, and Benzo[b is 0.3 milligram.
30.0 milligrams of Benzo[bs of the electronic balance weighing utilizing precision to be 0.01 milligram are dissolved in 100.0 milliliters of o-dichlorohenzene solvents, and by heating, magneton alr mode is accelerated to dissolve, and is configured to the pentacene solution of 0.3 mg/ml.
The electronic balance weighing utilizing precision to be 0.01 milligram obtains 29.7 milligrams of 3-hexyl substituting polythiophenes.
1.0mL liquid-transfering gun is utilized to take the above-mentioned pentacene solution prepared of 1.0ml, the 29.7 of above-mentioned weighing milligrams of 3-hexyl substituting polythiophenes are dissolved in this solution, by heating, the mode such as magneton stirring is accelerated to dissolve, and is configured to the Benzo[b/3-hexyl substituting polythiophene mixed solution of 30mg/mL.
Then pass through spin coating method by evenly laid out for this solution on electrode, after the volatilization of solvent o-dichlorohenzene, form Benzo[b/3-hexyl substituting polythiophene compound organic film.
Adopt 3-hexyl substituting polythiophene according to above-mentioned concentration proportioning, the pure 3-hexyl substituting polythiophene organic film of preparation non-doped material.
Preparation rigid basement organo-magnetoresistive film member
Structure simplification figure referring to the rigidity organic diode electronic components with magnetoresistance that Fig. 1, Fig. 1 provide for the embodiment of the present invention.Fig. 1 select glass as basal layer 04, 100 nano-indium stannum oxides are prepared on the glass substrate by the mode of magnetron sputtering, utilize photoetching technique, photoresist is smeared at indium tin oxide surfaces, template is utilized to block desired structure position, other positions expose, all the other positions are washed away by the sodium hydroxide developer solution of 0.5%, now expose tin indium oxide, " chloroazotic acid " solution being configured to by dilute hydrochloric acid and dust technology washes away the tin indium oxide exposed, after utilizing deionized water to clean, acetone is utilized to wash away photoresist, what now stay is the hearth electrode of desired structure, i.e. lower conductiving layer 03 in Fig. 1.
Utilize sol evenning machine, when constant rotational speed, modified Benzo[b/3-hexyl substituting polythiophene mixed solution is spin-coated on indium tin oxide surfaces, after the adjacent two chloroform volatilizations of solvent, form Benzo[b/3-hexyl substituting polythiophene mixture film layer, the i.e. modified organic molecule/Thin Polymer Mixture Films layer 02 with magnetoresistance in Fig. 1.
Utilizing vacuum thermal evaporation instrument, the template that 100 nanometer metallic silvers are determined by structure is deposited with on Benzo[b/3-hexyl substituting polythiophene mixture film layer surface, i.e. upper conductive layer 01 in Fig. 1.Namely the organic film component with " sandwich " organic diode structure on rigid basement glass is obtained.
The organic film component with diode structure finally prepared by above-mentioned steps carries out adaptability assembling, obtains the organic polymer magnetoresistive transducer of rigid basement.
The magnetoresistive transducer device that magnetoresistive transducer device prepared by above-mentioned steps of the present invention and pure 3-hexyl substituting polythiophene organic film assemble carries out performance detection, result is referring to table 1 and table 2, the rigidity organic film magneto-resistive transducing device magnetic response Sensitivity comparison that table 1 is based on 1% dopant material with based on pure material collects, and the rigidity organic film magneto-resistive transducing device electric conductivity contrast that table 2 is based on 1% dopant material with based on pure material collects.
Table 1 collects based on 1% dopant material with based on pure material rigidity organic film magneto-resistive transducing device magnetic response Sensitivity comparison
Table 2 collects based on 1% dopant material with based on the contrast of pure material rigidity organic film magneto-resistive transducing device electric conductivity
From above-mentioned testing result, the rigidity organic film magneto-resistive transducing device with magnetic resistance performance prepared based on the organic composite material after doping provided by the invention, compare traditional magnetosensitive device, electronic device magnetic resistance responsiveness provided by the invention strengthens (maximum up to～5 times), and conductive capability is remarkably reinforced.
Embodiment 2
Prepare Benzo[b/3-hexyl substituting polythiophene compound organic film
Solution preparation process is identical with example 1.
Utilize rod coater, be coated with under speed by evenly laid out on electrode constant paving, after the volatilization of solvent o-dichlorohenzene, form Benzo[b/3-hexyl substituting polythiophene compound organic film.
Adopt 3-hexyl substituting polythiophene according to above-mentioned concentration proportioning, the pure 3-hexyl substituting polythiophene organic film of preparation non-doped material.
Preparation flexible substrates organo-magnetoresistive film member
Structure simplification figure referring to the flexible organic diode electronic components with magnetoresistance that Fig. 2, Fig. 2 provide for the embodiment of the present invention.
Selecting polyethylene in Fig. 2 is basal layer 04, by 50 nano-indium stannum oxides, 50 nanometer silvers, 50 nano-indium stannum oxides are prepared in polyethylene flexible substrates by the mode of magnetron sputtering, bar type rubbing method is utilized to smear photoresist at indium tin oxide surfaces, template is utilized to block desired structure position, other positions expose, the alkaline-based developer being configured to by the sodium hydroxide of 0.5% washes away all the other positions, now expose tin indium oxide, the solution being configured to by dilute hydrochloric acid and dust technology washes away the Indium sesquioxide. tin silver/indium tin oxide material exposed, after utilizing deionized water to clean, alkaline solution is utilized to deluster photoresist, what now stay is the hearth electrode of desired structure, i.e. lower conductiving layer 03 in Fig. 2.
Utilize rod coater, it is coated with under speed constant paving and modified Benzo[b/3-hexyl substituting polythiophene mixed solution uniform spreading is coated in Indium sesquioxide. tin silver/indium tin oxide surfaces, after the adjacent two chloroform volatilizations of solvent, form Benzo[b/3-hexyl substituting polythiophene mixture film layer, the i.e. modified organic molecule/Thin Polymer Mixture Films layer 02 with magnetoresistance in Fig. 2.
Utilize printing instrument, control elargol concentration, at Benzo[b/3-hexyl substituting polythiophene one layer of elargol of mixture film layer surface printing, it is thus achieved that this type of organo-magnetoresistive electronic installation on flexible substrates polyethylene, i.e. upper conductive layer 01 in Fig. 2.Namely the suprabasil organic film component with " sandwich " organic diode structure of flexible polyethylene is obtained.
The organic film component with diode structure finally prepared by above-mentioned steps carries out adaptability assembling, obtains the organic polymer magnetoresistive transducer of flexible substrates.
The magnetoresistive transducer device that magnetoresistive transducer device prepared by above-mentioned steps of the present invention and pure 3-hexyl substituting polythiophene organic film assemble carries out performance detection, and result is referring to table 3 and table 4.The flexible organic film magneto-resistive transducing device magnetic response Sensitivity comparison that table 3 is based on 1% dopant material with based on pure material collects, and the flexible organic film magneto-resistive transducing device electric conductivity contrast that table 4 is based on 1% dopant material with based on pure material collects.
Table 3 collects based on 1% dopant material with based on pure material flexible organic film magneto-resistive transducing device magnetic response Sensitivity comparison
Table 4 collects based on 1% dopant material with based on the contrast of pure material flexible organic film magneto-resistive transducing device electric conductivity
From above-mentioned testing result, the flexible organic film magneto-resistive transducing device with magnetic resistance performance prepared based on the organic composite material after doping provided by the invention, compare traditional magnetosensitive device, electronic device magnetic resistance responsiveness provided by the invention strengthens (maximum up to～5 times), and conductive capability is remarkably reinforced.
Above to a kind of modified polythiophene class organo-magnetoresistive thin-film material provided by the invention and preparation method thereof, application is described in detail, principles of the invention and embodiment are set forth by specific case used herein, the explanation of above example is only intended to help to understand method and the core concept thereof of the present invention, should be understood that, for those skilled in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out some improvement and modification, these improve and modify in the protection domain also falling into the claims in the present invention.
Claims (10)
1. an organo-magnetoresistive thin-film material, it is characterised in that obtained by after polythiophene class compound and condensed-nuclei aromatics analog derivative compound.
2. organo-magnetoresistive thin-film material according to claim 1, it is characterised in that described polythiophene class compound includes one or more in 3-hexyl substituting polythiophene, 3-octyl group substituting polythiophene and poly-(3-butyl polythiophene-2,5-bis-base)；
Described condensed-nuclei aromatics analog derivative includes one or more in Benzo[b five polythiophenes, 6,13-dimethyl Benzo[b and 6,13-diethyl Benzo[b.
3. organo-magnetoresistive thin-film material according to claim 1, it is characterised in that the mass ratio of described condensed-nuclei aromatics analog derivative and described polythiophene class compound is (0.1～10): (99.9～90).
4. organo-magnetoresistive thin-film material according to claim 1, it is characterised in that the thickness of described organo-magnetoresistive thin film is 50nm～1 μm；
The carrier mobility of described organo-magnetoresistive thin film is 1 × 10-4cm2/ V s～0.1cm2/V·s。
5. the preparation method of an organo-magnetoresistive thin-film material, it is characterised in that comprise the following steps:
1), after polythiophene class compound and condensed-nuclei aromatics analog derivative being mixed in organic solvent, mixed liquor is obtained；
2), after mixed liquor film forming above-mentioned steps obtained, organo-magnetoresistive thin-film material is obtained.
6. preparation method according to claim 5, it is characterised in that described organic solvent includes o-dichlorobenzene, m-dichloro-benzenes, o-dichlorobenzene and one or more in chlorobenzene.
7. preparation method according to claim 5, it is characterised in that the method for described film forming includes pressing, spraying process, bar type rubbing method or print process.
8. preparation method according to claim 5, it is characterised in that described step 1) particularly as follows:
Condensed-nuclei aromatics analog derivative is dissolved in organic solvent, after adding the mixing of polythiophene class compound, obtains mixed liquor.
9. the organo-magnetoresistive thin-film material described in Claims 1 to 4 any one or the organo-magnetoresistive thin-film material prepared by the claim 5～8 any one application in mistor element.
10. an organic electronic element, has Rotating fields and at least two contact of at least three layers, it is characterised in that
Described three layers is upper conductive layer, organic intermediate layer and lower conductiving layer；Wherein, described organic intermediate layer adopts the organo-magnetoresistive thin-film material described in Claims 1 to 4 any one or the organo-magnetoresistive thin-film material prepared by the method described in claim 5～8 any one.
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| CN101427145A (en) * | 2006-04-26 | 2009-05-06 | 西门子公司 | Organo-magnetoresistive sensor and uses thereof |
| CN102110515A (en) * | 2009-12-29 | 2011-06-29 | 中国科学院物理研究所 | Magnetic multilayer film for organic magnetoresistance device and manufacturing method thereof |
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| CN101427145A (en) * | 2006-04-26 | 2009-05-06 | 西门子公司 | Organo-magnetoresistive sensor and uses thereof |
| CN102110515A (en) * | 2009-12-29 | 2011-06-29 | 中国科学院物理研究所 | Magnetic multilayer film for organic magnetoresistance device and manufacturing method thereof |
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