CN110444667A - A kind of preparation method of organic diode laminated film - Google Patents
A kind of preparation method of organic diode laminated film Download PDFInfo
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- CN110444667A CN110444667A CN201910720334.9A CN201910720334A CN110444667A CN 110444667 A CN110444667 A CN 110444667A CN 201910720334 A CN201910720334 A CN 201910720334A CN 110444667 A CN110444667 A CN 110444667A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 40
- -1 chloro- 4- fluorophenyl Chemical group 0.000 claims abstract description 24
- 239000004411 aluminium Substances 0.000 claims abstract description 19
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 17
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 claims abstract description 17
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 17
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 claims abstract description 15
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 claims abstract description 15
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001771 vacuum deposition Methods 0.000 claims description 19
- 229910052774 Proactinium Inorganic materials 0.000 claims description 15
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 229920000049 Carbon (fiber) Polymers 0.000 claims 1
- 239000004917 carbon fiber Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 52
- 239000004744 fabric Substances 0.000 abstract description 22
- KYNYDOGKVPHFNF-UHFFFAOYSA-N 2-phenylmethoxy-3H-pyridin-4-one Chemical compound C(C1=CC=CC=C1)OC1=NC=CC(C1)=O KYNYDOGKVPHFNF-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 10
- 239000010409 thin film Substances 0.000 abstract description 5
- 238000007738 vacuum evaporation Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 21
- 150000002894 organic compounds Chemical class 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 16
- 239000000835 fiber Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 9
- RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000002687 intercalation Effects 0.000 description 3
- 238000009830 intercalation Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 241000522215 Dipteryx odorata Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- OKWATXMSXLFWAN-UHFFFAOYSA-N 1-(2h-triazol-4-yl)piperidine Chemical compound C1CCCCN1C1=CNN=N1 OKWATXMSXLFWAN-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- VFSJPKSXNJQIFG-UHFFFAOYSA-N 6-methoxyquinazoline;hydrochloride Chemical compound Cl.N1=CN=CC2=CC(OC)=CC=C21 VFSJPKSXNJQIFG-UHFFFAOYSA-N 0.000 description 1
- 206010017472 Fumbling Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- 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 a potential-jump barrier or a surface barrier
- H10K10/20—Organic diodes
-
- 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 a potential-jump barrier or a surface barrier
- H10K10/80—Constructional details
-
- 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
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Abstract
The invention belongs to thin film technique field, specially a kind of preparation method of organic diode laminated film.Method proposed by the present invention is successively vacuum evaporation 7 on carbon cloth, 8- dihydroxy -3- (4 '-fluorophenyl) cumarin, N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5-, aluminium, obtain organic diode laminated film.The commutating ratio of the organic diode laminated film is 6,210,000 ~ 6,930,000.
Description
Technical field
The invention belongs to thin film technique field, specially a kind of preparation method of organic diode laminated film.
Background technique
Organic electronics are exactly to use organic matter as the electronics of " conduction " material, i.e., with organic molecule and macromolecule material
Electronic device and relevant issues based on material, especially high-molecular compound semiconductor material, grinding in terms of its electric conductivity
Study carefully and obtains Nobel chemistry Prize in 2000.Diode is in electronic component, and there are two the devices of electrode for a kind of tool, only allows electricity
Stream is flowed through by single direction, and many uses are the functions using its rectification.
Liu Ming etc. discloses a kind of organic diode device and preparation method thereof (CN102074653A), belongs to semiconductor skill
Art field.The organic diode device, including substrate, anode, organic semiconductor layer and cathode, anode and organic semiconductor layer
Between also set up at least one layer of organic Iy self-assembled layer, organic Iy self-assembled layer is made of metallo-organic complex；Anode by except gold with
Outer anode metal or alloy is made.The described method includes: making anode on substrate；It makes on the anode organic from group
Fill layer；Organic semiconductor layer is made on organic Iy self-assembled layer；Cathode is made on the organic semiconductor layer；It is described to have
Machine Iy self-assembled layer is made of metallo-organic complex；The anode by addition to gold anode metal or alloy be made.The invention
Organic diode device performance is high, stability is good and at low cost, and preparation process is simple, reproducible.
Huang such as discloses a kind of organic diode and preparation method thereof (CN102891264A).The organic diode packet
Transparent flexible substrate, transparent positive electrode, transparent negative electrode, the area flexible and transparent p of doping and the area flexible and transparent n of doping are included,
In, the transparent negative electrode is located at the transparent flexible substrate, and the area flexible and transparent n of the doping is located at described transparent negative
On electrode, the area flexible and transparent p of the doping is located on the area flexible and transparent n of the doping, the transparent positive electrode position
On the area flexible and transparent p of the doping.The invention also discloses a kind of preparation methods of organic diode.The present invention is mentioned
Organic diode of confession and preparation method thereof replaces traditional inorganic material using transparent organic material, at low cost, is guaranteeing
On the basis of the fundamental characteristics for not changing traditional inorganic device, low in energy consumption, fast response time is not necessarily to high temperature work in preparation process
Skill also as save preparation time on the basis of reducing energy consumption.
Bright east of instrument etc. discloses a kind of organic diode electrical storage device and method for being provided simultaneously with storage and rectification
(CN104979473A), which increases by one layer of buffer layer between anode-medium bed boundary, and entire device is from top to bottom successively
Be: metallic cathode, dielectric layer, anode buffer layer, ito anode substrate, the anode buffer layer of this structure had both had preferable exhausted
Edge, while ITO can also be modified.Pass through measurement device electrical properties and relevant experimental data, it is possible to determine that this device is
One is provided simultaneously with the stabilization organic diode electrical storage device of storage and rectification.It is an advantage of the invention that the organic diode
Memory device has storage hysteresis and considerable rectifying effect simultaneously, has big on-off ratio commutating ratio, and apply and continue outside
Preferable performance is also maintained after voltage, meanwhile, easily designed compared to same type device architecture, the invention yield is high, has pervasive
Property, there is important research significance.
A Ji washes space etc. and discloses a kind of low threshold voltage organic diode (CN104409634A), and the low threshold voltage is organic
Diode includes: lower electrode；The metal oxide intercalation being formed on lower electrode；It is formed on metal oxide intercalation
Organic functional material layer；The organic material buffer layer being formed on organic functional material layer；And it is formed in organic material and delays
Rush the top electrode on layer.The invention also discloses a kind of method for preparing low threshold voltage organic diode.Using the invention,
The contact berrier of lower electrode and organic material layer is adjusted with metal oxide intercalation, to reach the threshold of adjustment organic diode
The effect of threshold voltage significantly reduces the threshold voltage of organic diode.
In conclusion between two electrodes by organic functional thin film folder, constructing the electronic device of sandwich structure, being big
The technology of preparing of most organic diodes, organic functional thin film decide the performance of organic diode, but organic diode is opened
Hair is still in the stage of fumbling, needs constantly to accumulate knowledge and experience.The common recognition of those skilled in the art is, organic diode it is whole
Stream is more related to the composition of organic functional thin film than not only, additionally depends on the structure of film, needs to cooperate with optimization organic functions thin
The component and structure of film, to obtain the organic diode of high commutating ratio.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of organic diode laminated film.
The preparation method of organic diode laminated film proposed by the present invention, the specific steps are as follows:
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30 ~ 50nm thickness is successively deposited in fiber cloth, (3- is chloro- by the N- of 30 ~ 50nm thickness
4- fluorophenyl) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 30 ~
1- hydroxyl -2- methylol-the 5- two of (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide of 50nm thickness, 30 ~ 50nm thickness
The aluminium of benzyloxy -4- pyridone, 100 ~ 150nm thickness, obtains organic diode laminated film.
Reference literature (Fudan Journal (natural science edition), 2005,44 (4): 597-600) function generator, number
Oscillograph, universal meter measure the electrical property of device, measure organic diode laminated film commutating ratio be 6,210,000 ~
6930000.
Organic diode laminated film prepared by the present invention has " carbon cloth/organic layer/metal " structure, wherein organic
Layer is formed by four kinds of layer-by-layer vacuum depositions of organic material, if only using a kind of organic material prepares organic layer, the present invention is mentioned
As a comparison for following 4 technical solutions:
(1) the 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, In
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30nm thickness, the aluminium of 100nm thickness are successively deposited on carbon cloth, obtains organic multiple
Film is closed, the electrical property of device is measured with function generator, digital oscilloscope, universal meter, it is thin to measure organic composite
The commutating ratio of film is 1, i.e. device does not have rectification characteristic.
(2) the 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3 Pa
Under, N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- the amino-l, 3,4- thiadiazoles -2- of 50nm thickness are successively deposited on carbon cloth
Sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 150nm thickness aluminium, organic compound film is obtained, with function generator, number
Oscillograph, universal meter measure the electrical property of device, and the commutating ratio for measuring organic compound film is 1, i.e. device does not have
There is rectification characteristic.
(3) the 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3 Pa
Under, it is thick that (1- benzyl -4- neighbour pyridyl group -1,2,3-triazoles) nickelous bromide of 40nm thickness, 150nm are successively deposited on carbon cloth
Aluminium obtains organic compound film, is measured, is measured to the electrical property of device with function generator, digital oscilloscope, universal meter
The commutating ratio of organic compound film is 1, i.e. device does not have rectification characteristic.
(4) the 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3 Pa
Under, two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5-, the 100nm that 30nm thickness is successively deposited on carbon cloth are thick
Aluminium, obtain organic compound film, the electrical property of device measured with function generator, digital oscilloscope, universal meter, survey
The commutating ratio for obtaining organic compound film is 1, i.e. device does not have rectification characteristic.
Four kinds of organic matters it can be seen from correlation technique scheme (1) ~ (4): 7,8- dihydroxy -3- (4 '-fluorophenyl) tonka-bean
Element, N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -
4- amine, (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, two benzyloxy -4- pyridine of 1- hydroxyl -2- methylol -5-
Ketone, cannot be separately as the organic layer material of organic diode laminated film.
If four kinds of organic matters in the organic layer of the organic diode laminated film in the present invention lack one kind, the present invention
Also provide following 4 technical solutions as a comparison:
(5) lack 7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin in organic layer
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) third of 30nm thickness is successively deposited in fiber cloth
Oxygroup] -6- methoxyquinazoline hydrochloride -4- amine, (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide of 40nm thickness, 50nm thickness
Two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5-, 100nm thickness aluminium, obtain organic compound film, occurred with function
Device, digital oscilloscope, universal meter measure the electrical property of device, and the commutating ratio for measuring organic compound film is 1, i.e. device
Part does not have rectification characteristic.
(6) lack N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) third in organic layer
Oxygroup] -6- methoxyquinazoline hydrochloride -4- amine
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 50nm thickness, (1- benzyl -4- neighbour's pyrrole of 40nm thickness are successively deposited in fiber cloth
Piperidinyl -1,2,3- triazole) nickelous bromide, the two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5- of 30nm thickness, 100nm thickness
Aluminium, obtain organic compound film, the electrical property of device measured with function generator, digital oscilloscope, universal meter, survey
The commutating ratio for obtaining organic compound film is 1, i.e. device does not have rectification characteristic.
(7) lack (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide in organic layer
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 50nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 30nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 50nm thickness 1- hydroxyl
The aluminium of two benzyloxy -4- pyridone of base -2- methylol -5-, 150nm thickness, obtains organic compound film, with function generator, number
Word oscillograph, universal meter measure the electrical property of device, and the commutating ratio for measuring organic compound film is 1, i.e., device is not
With rectification characteristic.
(8) lack two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5- in organic layer
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 40nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 40nm thickness (1-
Benzyl -4- neighbour pyridyl group -1,2,3-triazoles) nickelous bromide, 150nm thickness aluminium, organic compound film is obtained, with function generator, number
Word oscillograph, universal meter measure the electrical property of device, and the commutating ratio for measuring organic compound film is 1, i.e., device is not
With rectification characteristic.
By above-mentioned correlation technique scheme (5) ~ (8) once it can be seen from a certain component missing in organic layer, then prepare
The laminated film of " carbon cloth/organic layer/metal " structure does not have rectification effect.
If four kinds of organic matter vaporization platings sequence in the organic layer of the organic diode laminated film in the present invention is different, this
Invention also provides following 3 technical solutions as a comparison:
(9) two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5- is first deposited
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
Two benzyloxy -4- the pyridone of 1- hydroxyl -2- methylol -5- of 50nm thickness, the 7,8- bis- of 30nm thickness are successively deposited in fiber cloth
N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles-of hydroxyl -3- (4 '-fluorophenyl) cumarin, 50nm thickness
2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 30nm thickness (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) bromination
The aluminium of nickel, 100nm thickness, obtains organic compound film, with function generator, digital oscilloscope, universal meter to the electrical property of device
It measures, the commutating ratio for measuring organic compound film is 6.9, i.e. the rectification characteristic of device is weaker.
(10) (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide is first deposited
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
(1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide of 30nm thickness, the 1- hydroxyl-of 50nm thickness are successively deposited in fiber cloth
Two benzyloxy -4- pyridone of 2- methylol -5-, 7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30nm thickness, 50nm are thick
N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -
The aluminium of 4- amine, 100nm thickness, obtains organic compound film, with function generator, digital oscilloscope, universal meter to the electrical property of device
It can be carried out measurement, the commutating ratio for measuring organic compound film is 7.8, i.e. the rectification characteristic of device is weaker.
(11) N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group]-first is deposited
6- methoxyquinazoline hydrochloride -4- amine
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
N- (the chloro- 4- fluorophenyl of 3-) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) third of 50nm thickness is successively deposited in fiber cloth
Oxygroup] -6- methoxyquinazoline hydrochloride -4- amine, (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide of 30nm thickness, 50nm thickness
Two benzyloxy -4- pyridone of 1- hydroxyl -2- methylol -5-, 30nm thickness 7,8- dihydroxy -3- (4 '-fluorophenyl) tonka-bean
The aluminium of element, 100nm thickness, obtains organic compound film, with function generator, digital oscilloscope, universal meter to the electrical property of device
It measures, the commutating ratio for measuring organic compound film is 5.9, i.e. the rectification characteristic of device is weaker.
By above-mentioned correlation technique scheme (9) ~ (11) once it can be seen from organic layer membrane structure change, then make
The commutating ratio of the laminated film of standby " carbon cloth/organic layer/metal " structure is only about the million of claim technical solution
/ mono-, rectification characteristic decline is significant.
In conclusion the beneficial effects of the present invention are: use 4 kinds itself not have commutating character material, by excellent
Change component and device architecture, obtains the organic diode laminated film with high commutating ratio；Moreover, in organic layer if
Lack a certain material for not having commutating character itself, then the laminated film of " carbon cloth/organic layer/metal " structure is whole
Fluidity can disappear；If membrane structure changes, the commutating ratio of laminated film is only about the million of claim technical solution
/ mono-.
Therefore, the technical solution of the claims in the present invention has marked improvement outstanding, produces unexpected technology
Effect, the creativeness with patent statute.
Specific embodiment
The present invention is further described below by example.
Embodiment 1
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 30nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 30nm thickness (1-
Benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, 30nm thickness two benzyloxy -4- pyridine of 1- hydroxyl -2- methylol -5-
The aluminium of ketone, 100nm thickness, obtains organic diode laminated film；With function generator, digital oscilloscope, universal meter to device
Electrical property measures, and the commutating ratio for measuring organic diode laminated film is 6,930,000.
Embodiment 2
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 50nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 50nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 50nm thickness (1-
Benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, 50nm thickness two benzyloxy -4- pyridine of 1- hydroxyl -2- methylol -5-
The aluminium of ketone, 150nm thickness, obtains organic diode laminated film；With function generator, digital oscilloscope, universal meter to device
Electrical property measures, and the commutating ratio for measuring organic diode laminated film is 6,210,000.
Embodiment 3
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 50nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 30nm thickness (1-
Benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, 50nm thickness two benzyloxy -4- pyridine of 1- hydroxyl -2- methylol -5-
The aluminium of ketone, 100nm thickness, obtains organic diode laminated film；With function generator, digital oscilloscope, universal meter to device
Electrical property measures, and the commutating ratio for measuring organic diode laminated film is 6,660,000.
Embodiment 4
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 35nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 45nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 50nm thickness (1-
Benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, 30nm thickness two benzyloxy -4- pyridine of 1- hydroxyl -2- methylol -5-
The aluminium of ketone, 120nm thickness, obtains organic diode laminated film；With function generator, digital oscilloscope, universal meter to device
Electrical property measures, and the commutating ratio for measuring organic diode laminated film is 6,760,000.
Embodiment 5
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 39nm thickness, N- (the chloro- 4- fluorobenzene of 3- of 35nm thickness are successively deposited in fiber cloth
Base) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 42nm thickness (1-
Benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, 48nm thickness two benzyloxy -4- pyridine of 1- hydroxyl -2- methylol -5-
The aluminium of ketone, 132nm thickness, obtains organic diode laminated film；With function generator, digital oscilloscope, universal meter to device
Electrical property measures, and the commutating ratio for measuring organic diode laminated film is 6,410,000.
Claims (1)
1. a kind of preparation method of organic diode laminated film, which is characterized in that specific step is as follows:
The 200 grammes per square metre carbon cloths of 5cm × 4cm are placed in vacuum coating equipment, are 2 × 10 in vacuum degree-3Under Pa, in carbon fiber
7,8- dihydroxy -3- (4 '-fluorophenyl) cumarin of 30 ~ 50nm thickness, N- (the chloro- 4- of 3- of 30 ~ 50nm thickness are successively deposited on Wei Bu
Fluorophenyl) -7- [3- (5- amino-l, 3,4- thiadiazoles -2- sulfydryl) propoxyl group] -6- methoxyquinazoline hydrochloride -4- amine, 30 ~ 50nm
1- hydroxyl -2- methylol -5- hexichol the first of thick (1- benzyl -4- neighbour pyridyl group -1,2,3- triazole) nickelous bromide, 30 ~ 50nm thickness
The aluminium of oxygroup -4- pyridone, 100 ~ 150nm thickness, obtains organic diode laminated film；
Wherein the performance of organic diode laminated film is that commutating ratio is 6,210,000 ~ 6,930,000.
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Application publication date: 20191112 |