CN106410028B - A kind of organic film electronic device and preparation method thereof based on racemic modification - Google Patents
A kind of organic film electronic device and preparation method thereof based on racemic modification Download PDFInfo
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- CN106410028B CN106410028B CN201610940554.9A CN201610940554A CN106410028B CN 106410028 B CN106410028 B CN 106410028B CN 201610940554 A CN201610940554 A CN 201610940554A CN 106410028 B CN106410028 B CN 106410028B
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- 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
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- H—ELECTRICITY
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- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H—ELECTRICITY
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- H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract
This patent discloses a kind of organic film electronic device and preparation method thereof based on racemic modification, including organic film；The organic film is racemic modification film；Racemic modification is by left molecule and right handed molecular composition.Present invention firstly provides in the modified method for utilizing racemic thinking of electronic device organic film material, in the preparation of applied memory device, pass through this racemization, device performance is very significantly improved, and has potential application prospect to later semiconductor device piece optimization and other organic assemblies.
Description
Technical field
The invention belongs to advanced material technical fields, and in particular to a kind of organic film electronics device based on racemic modification
Part and preparation method thereof improves a lot to electronic device practical performance.
Background technique
First generation electronic product is using electron tube as core.It has been born in the world at the end of the 1940s first three pole of semiconductor
It the features such as pipe, it is with small and exquisite, light, power saving, long service life, is soon applied by various countries, in very large range instead of electricity
Son pipe.There is first piece of integrated circuit in the world in the fifties latter stage, it is electronic component integrations such as many transistors one
On block silicon chip, develop electronic product to smallerization.Due to the needs of social development, electronic device becomes more and more multiple
Miscellaneous, this requires electronic device must have that reliability, speed are fast, consumption power is small and light weight, miniaturization, at low cost
The features such as.Wherein the discovery of silicon-based semiconductor opens the revolution of electronic industry.
In the past few decades, apparent increase is had occurred in the memory capacity of inorganic semiconductor memory device, and in size
Also significant reduce occurs.In current memory device, this has passed through traditional lithography technique and has realized.However, this
Class technology also encounters some urgent need to solve the problems at present, such as the limitation of lithography technique physically resolution ratio, height production
Cost etc..These have all seriously threatened the development of current inorganic semiconductor storage material.Discovery accordingly, with respect to alternative materials and
Research is very significant.
Recently, the memory device based on organic semiconducting materials is increasingly by the concern of scientists from all over the world.They with it is low at
This, be easy to large scale preparation, three-dimensional accumulation and device architecture flexible and storage can be regulated and controled by structural modification
The advantages that performance, is widely studied, wherein the resistance device with simple structure is most study.Its basic unit of storage
It is " electrode/membrane/electrode " simple sandwich structure, realizes that two apparent conductive states are presented in storage principle under the applied field,
That is " 0 " or " OFF " state and " 1 " or " ON " state, to realize information storage.This unlike inorganic semiconductor memory device by
It discharges (0) in circuit and charging (1) process completes information storage, the impedance type device based on organic semiconducting materials has completely
The mode of different operation is using response of the active layer to voltage, i.e. presentation high-and low guiding state, to realize that information stores.It compares
In traditional general inorganic semiconductor memory device that complicated circuit forms by small, device architecture obtains greatly simple
Change.It (is corresponded in addition, the advantage of organic semiconductor micro-nano processing aspect makes its storage density can reach 1012 bit/cm2 or more
The diameter of information point is in 10 nm or less), compared with the device of general 106 bit/cm2 of storage density in market, storage capacity is
Surprising.In short, Organic Electricity storage research has established theory and technology basis to the development of the high density information technology in future.Letter
The fast-developing of breath technology has a higher requirement to memory, and such as storage speed is faster, functional dimension is smaller, storage density
Higher and manufacture craft is simpler etc..Although currently, the silicon substrate electrical storage based on conventional semiconductors have quick storage with
And information is held time the features such as long, but there is also sizes it is larger, preparation process is complicated and production cost is higher the problems such as.
In order to meet the requirement of information age mass memory, the challenge of increasingly serious microtechnology is overcome, it is more and more
Research institution start will to research and develop focus and turn to emerging electric memory technology.Currently, emerging memory technology mainly has ferroelectric memory
(FeRAM), magnetic random memory (MRAM), organic electrical storage (OBM), phase transition storage (PCM), nano-crystal memory and
Carbon nanotube memory etc., wherein organic storage has easy processing, high density, low cost, low-power consumption, can be made into large area and soft
The advantages that property, information data storing and in terms of have potential application prospect.In recent years, in relation to small molecule and
The research of polymer achieves very big breakthrough, but very big breakthrough is never had in stability, and a large amount of research is all pair
The change of molecular structure and the change of external condition are to inquire into the influence to device performance, not about accumulation factor to device
The report of the influence of energy.
Summary of the invention
The invention discloses a kind of organic film electronic device and preparation method thereof based on racemic modification；Racemic modification by
Left molecule and right handed molecular composition, electronic structure and molecular entergy level track having the same guarantee the phase of molecular level
Like property, to improve the performance of electronic device.
To achieve the above object of the invention, the present invention adopts the following technical scheme:
A kind of organic film electronic device based on racemic modification, including organic film；The organic film is racemic
Body thin film；The racemic modification is by left molecule and right handed molecular composition.
In above-mentioned technical proposal, using chiral molecules, existing molecule is avoided to have group, flatness, conjugacy, chemical ring
The variation of many factors such as border and cannot only consider the problems of a kind of variation of factor, in the present invention, monomerism can be closest
Chiral unit, preparation process do not change each molecular energy level and electron orbit；Racemic modification organic film has finer and close
Accumulation and smaller interlamellar spacing, greatly improve the ternary ratio and cut-in voltage ratio of electronic device, improve electronics device
The performance of part.
Racemic modification organic film disclosed by the invention can be used for include metal electrode and indium oxide tin glass electricity
Sub- device, as the middle layer of sandwich structure, organic film is between metal electrode and indium oxide tin glass；Electronic device
Including memory electronic device, electronics field-effect quartz crystal device, resistance-type component, capacitance component, inductance component etc..Metal
Electrode and indium oxide tin glass can be respectively as the anode material and cathode material of electronic device, wherein metal electrode
Aluminium electrode, silver electrode etc..
The preparation method of the invention also discloses a kind of organic film electronic device based on racemic modification, including following step
It is rapid: to prepare organic film on indium oxide tin glass surface；Then metal electrode is prepared on organic film surface；The organic film
For racemic modification；The racemic modification is by left molecule and right handed molecular composition；The organic film with a thickness of 90~
110 nanometers, the too thin or too thick transmission for being all unfavorable for electronics, to the number of plies and charge of molecules align under the thickness that the present invention limits
The depth of trap has very important influence, it is hereby achieved that ternary ratio and cut-in voltage ratio etc. were had excellent performance
Electronic device.
In above-mentioned technical proposal, prepared using solution spin-coating method or vapour deposition method on indium oxide tin glass surface organic thin
Film.Preferably, the spin coating revolving speed of the spin-coating method is 1600 turns per minute, and spin-coating time is 30 seconds；In vacuum after the completion of spin coating
Under the conditions of spontaneously dry obtain organic film.From the point of view of vapor deposition, evaporating quality is 5~10mg/cm2, current control is in 40-50A
Obtained film quality is higher.
In above-mentioned technical proposal, spin-coating method is specially by spin-coating equipment by racemic modification solution in clean tin indium oxide
Glass surface carries out spin coating, then spontaneously dries in vacuum equipment, and removal solvent obtains organic film；The organic film
With a thickness of 90~110 nanometers；In racemic modification solution, solvent is ketone or alcohols solvent, molecule heap of the solvent to racemic modification
Product has an impact, so that the performance of obtained organic film is influenced, the final performance for influencing the electronic device comprising the organic film,
The preferred cyclohexanone of the present invention or ethyl alcohol greatly improve electronics device conducive to finer and close packing of molecules and smaller interlamellar spacing
The ternary ratio and cut-in voltage ratio of part, improve the performance of electronic device.According to an embodiment of the invention, the present invention is excellent
Select spin-coating method.
In above-mentioned technical proposal, the preparation of electronic device can also include the preparation and group of base material and encapsulating material
Dress, for example, indium oxide tin glass is compound with clear glass substrate, according to the application range of electronic device, those skilled in the art
Conventional steps can be increased, racemic modification of the present invention is not influenced and prepare the technical effect that organic film improves electronic device performance.
The present invention further discloses a kind of organic films for electronic device, are racemic modification film；Disappear outside described
Body is revolved by left molecule and right handed molecular composition.Racemic modification solution can be spin-coated in substrate or by racemic modification
It is vaporized in substrate, to obtain the organic film for electronic device.
Further, the application the invention discloses racemic modification in the organic film that preparation is used for electronic device；Institute
Racemic modification is stated by left molecule and right handed molecular composition.Racemic modification organic film has finer and close accumulation and smaller
Interlamellar spacing, greatly improve the ternary ratio and cut-in voltage ratio of electronic device, improve the performance of electronic device.
The invention also discloses racemic modifications to prepare the application in organic thin film electronic device；The racemic modification is by a left side
Chiral molecules and right handed molecular composition.Racemic modification organic film of the present invention can be with indium oxide tin glass, metal electrode group
At sandwich structure, it to be used for electronic device, including memory electronic device, electronics field-effect quartz crystal device, resistance-type component, electricity
Hold component, inductance component etc..
In the present invention, for racemic modification by left molecule and right handed molecular composition, the two molar ratio is 1, such as following
Chiral molecules:
Compared with prior art, the present invention has the advantage that
(1) present invention utilizes for the first time obtains organic film by left molecule and the racemic modification of right handed molecular composition,
After electronic device, the ternary ratio and cut-in voltage ratio of electronic device are greatly improved, electronic device is improved
Performance；According to embodiments of the present invention, ternary performance can be made to obtain about 20% under multi-solvents, different film mode to mention
Height, this on device stability for, progress it is outstanding, unexpected technical effect is all achieved under different modes.
(2) present invention obtains organic film by racemic modification using spin-coating method or vapour deposition method, conducive to unimolecule accumulation
Improve, especially using cyclohexanone or ethyl alcohol as spin coating solvents, conducive to finer and close packing of molecules and smaller interlamellar spacing, greatly
The ternary ratio and cut-in voltage ratio for improving electronic device, improve the performance of electronic device.
(3) present invention is obtained with spin-coating method or vapour deposition method by racemic modification without complicated, expensive production equipment
Organic film, complexed metal electrode, indium oxide tin glass sandwich structure consisting, eventually for such as memory electronic device, electricity
The electronic devices such as subfield effect quartz crystal device, resistance-type component, capacitance component, inductance component, improve electronic device
Performance, have excellent industrial feasibility.
Detailed description of the invention
Fig. 1 is the film thickness scanning electron microscope (SEM) photograph of unimolecule S film；
Fig. 2 is the film thickness scanning electron microscope (SEM) photograph of racemic modification film；
Fig. 3 is the scanning electron microscope (SEM) photograph of unimolecule S film surface；
Fig. 4 is the scanning electron microscope (SEM) photograph of racemic modification film surface；
Fig. 5 is the XRD diagram of unimolecule R and unimolecule S powder；
Fig. 6 is the film XRD diagram of unimolecule S and racemic modification；
Fig. 7 is ternary statistical chart of the thin-film device of unimolecule S and racemic modification under different production methods；
Fig. 8 is cut-in voltage statistical chart of the thin-film device of unimolecule S and racemic modification under different production methods；
Fig. 9 is the binary system ternary curve graph of the thin-film device of unimolecule S and racemic modification.
Specific embodiment
Ethyl alcohol, cyclohexanone, acetone, the other materials such as deionized water are bought from traditional Chinese medicines；Chiral molecules is bought from Bellingwell company,
98% or more purity.
Embodiment one
Device is sandwich structure, the ITO/ racemic modification/Al sandwich structure of the right handed molecule/Al of ITO/, preparation
Are as follows: before one layer of organic matter of spin coating, ITO(tin indium oxide) glass first cleaned with washing powder, then successively in deionized water,
It cleans within ultrasound 30 minutes in acetone and ethyl alcohol and is dried for standby.Right handed molecule cyclohexanone solution, the right side of 10 mg/mL is respectively configured
Chiral molecules ethanol solution, racemic modification (R:S=1:1, mol) cyclohexanone solution, racemic modification (R:S=1:1, mol) second
Alcoholic solution, then front end of the syringe needle is respectively got to solution by syringe plus the filtering head of 0.22 micron pore size again
The surface ITO carries out spin coating, and revolving speed is controlled at 1600 turns per minute, spin coating 30 seconds.The good ito glass of spin coating is put into vacuum drying
It is spontaneously dried in case, removes solvent.Finally the ito glass of one layer of organic matter of spin coating is put into high vacuum vapor deposition instrument and plates one layer
Top electrode of the Al spot that thickness is about 100 nm, diameter is 0.5 mm as device.
Embodiment two
Device is sandwich structure, the ITO/ racemic modification/Al sandwich structure of the left molecule/Al of ITO/, preparation
Are as follows: before one layer of organic matter is deposited, ITO(tin indium oxide) glass first cleaned with washing powder, then successively in deionized water,
It cleans within ultrasound 30 minutes in acetone and ethyl alcohol and is dried for standby.By the right handed molecule of 100mg, racemic modification (R:S=1:1, mol)
Under a high vacuum, 45A is vaporized on indium oxide tin glass surface respectively, obtains about 100nm thickness organic film.Finally steamed in high vacuum
Plating instrument in plate a layer thickness be about 100 nm, diameter be 0.5 mm Al spot as device top electrode.
Embodiment one, the chiral molecules of embodiment two are as follows:
(1) SEM film thickness is tested:
Such as Fig. 1 and 2, the right handed molecule of unimolecule S(for the vapor deposition respectively tested under high resolution electron microscopy) film and disappear outside
Revolve the SEM figure of film film thickness, hence it is evident that it can be seen that its film thickness is all about in 110nm or so.Simultaneously to unimolecule S film and racemic modification film
Surface topography test, as a result respectively such as Fig. 3 and Fig. 4, hence it is evident that see that the film of racemic is easier to crystallization and intermolecular knot
It closes even closer.
(2) X-Ray is tested:
XRD test is done to the powder of enantiomer R and S first, from fig. 5, it can be seen that the unimolecule accumulation property of its R and S
Matter is just the same.Then to the unimolecule S film after film is made, racemic modification film has done XRD test respectively, see Fig. 6, reflect
Very big difference, hence it is evident that racemic modification film ratio S film has finer and close accumulation and smaller interlamellar spacing.
(3) device performance counts
It is solvent spin coating, in such a way that cyclohexanone is three kinds of solvent spin coating and vapor deposition as Fig. 7 and Fig. 8 have been counted respectively by ethyl alcohol
Ternary ratio and cut-in voltage ratio.Show that the molecular property of racemic compound is the same, because of the improvement of bulk property
And biggish improvement is indicated on device performance, generally improve about 20% ternary ratio.
(4) memory performance is tested:
The above two organic layer device of difference is done into I-V under three kinds of different production methods (spin coating is using cyclohexanone as solvent)
Performance test, measured typical curve such as Fig. 9, wherein (a) is the right handed molecule/Al of device ITO/, (b) for outside device ITO/
Raceme/Al.
To sum up, it can be clearly seen that the presence of racemic modification and is to have clearly to the improvement of device performance
Generality, it is suitble to multi-solvents system and a variety of preparation methods.
Claims (8)
1. a kind of organic film electronic device based on racemic modification, it is characterised in that: described organic thin based on racemic modification
Film electronic device includes organic film；The organic film is racemic modification film；The racemic modification by left molecule with
Right handed molecular composition；The electronic device is memory electronic device；The left molecule is distinguished as follows with right handed molecule:
。
2. the organic film electronic device based on racemic modification according to claim 1, it is characterised in that: described to be based on disappearing outside
The organic film electronic device for revolving body further includes metal electrode and indium oxide tin glass；The organic film is located at metal electrode
Between indium oxide tin glass；The organic film with a thickness of 90~110 nanometers.
3. a kind of preparation method of the organic film electronic device based on racemic modification, which comprises the following steps:
Indium oxide tin glass surface prepares organic film；Then metal electrode is prepared on organic film surface；The organic film is outer
Racemization body thin film；The racemic modification is by left molecule and right handed molecular composition；The electronic device is electronic memory
Part；The left molecule is distinguished as follows with right handed molecule:
。
4. the preparation method of the organic film electronic device based on racemic modification according to claim 3, it is characterised in that: benefit
Organic film is prepared on indium oxide tin glass surface with solution spin-coating method or vapour deposition method；The organic film with a thickness of 90~
110 nanometers.
5. the preparation method of the organic film electronic device based on racemic modification according to claim 4, it is characterised in that: institute
The spin coating revolving speed for stating spin-coating method is 1600 turns per minute, and spin-coating time is 30 seconds, is done naturally under vacuum condition after the completion of spin coating
It is dry to obtain organic film；When the vapour deposition method, evaporating quality is 5~10mg/cm2, current control is in 40~50A.
6. a kind of organic film for electronic device, it is characterised in that: the organic film for electronic device is to disappear outside
Revolve body thin film；The racemic modification is by left molecule and right handed molecular composition；The electronic device is memory electronic device；
The left molecule is distinguished as follows with right handed molecule:
。
7. application of the racemic modification in the organic film that preparation is used for electronic device；The racemic modification by left molecule with
Right handed molecular composition；The electronic device is memory electronic device；The left molecule is distinguished as follows with right handed molecule:
。
8. racemic modification is preparing the application in organic thin film electronic device；The racemic modification by left molecule with it is right handed
Molecular composition；The electronic device is memory electronic device；The left molecule is distinguished as follows with right handed molecule:
。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1520360A (en) * | 2001-04-27 | 2004-08-11 | 3M | Method ofr thermally transferrying oriented materials for organic electronic displays and devices |
| CN1863890A (en) * | 2003-11-04 | 2006-11-15 | 株式会社Lg化学 | New compound capable of being used in organic layer of organic light emitting device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1520360A (en) * | 2001-04-27 | 2004-08-11 | 3M | Method ofr thermally transferrying oriented materials for organic electronic displays and devices |
| CN1863890A (en) * | 2003-11-04 | 2006-11-15 | 株式会社Lg化学 | New compound capable of being used in organic layer of organic light emitting device |
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