CN110491994A - End group is application of the porphyrin material of four sulfydryls in organic storage - Google Patents
End group is application of the porphyrin material of four sulfydryls in organic storage Download PDFInfo
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- CN110491994A CN110491994A CN201910844771.1A CN201910844771A CN110491994A CN 110491994 A CN110491994 A CN 110491994A CN 201910844771 A CN201910844771 A CN 201910844771A CN 110491994 A CN110491994 A CN 110491994A
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- 150000004032 porphyrins Chemical class 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 title claims abstract description 14
- 239000004065 semiconductor Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000001338 self-assembly Methods 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- PBHVCRIXMXQXPD-UHFFFAOYSA-N chembl2369102 Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C(C1=CC=C(N1)C(C=1C=CC(=CC=1)S(O)(=O)=O)=C1C=CC(=N1)C(C=1C=CC(=CC=1)S(O)(=O)=O)=C1C=CC(N1)=C1C=2C=CC(=CC=2)S(O)(=O)=O)=C2N=C1C=C2 PBHVCRIXMXQXPD-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical class C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000005669 field effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- NCAJWYASAWUEBY-UHFFFAOYSA-N 3-[20-(2-carboxyethyl)-9,14-diethyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoic acid Chemical compound N1C2=C(C)C(CC)=C1C=C(N1)C(C)=C(CC)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 NCAJWYASAWUEBY-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- QOTGGUKPKRQHKS-UHFFFAOYSA-N C(C)O[SiH](OCC)OCC.[Ru] Chemical compound C(C)O[SiH](OCC)OCC.[Ru] QOTGGUKPKRQHKS-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- -1 imino ruthenium triethoxysilane Chemical compound 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007334 memory performance Effects 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 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 potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- 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
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- 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
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
This patent is mainly to apply the porphyrin material that end group is four sulfydryls in organic memory device.By self assembly and surface chemical reaction, the interface between dielectric layer and organic semiconductor layer is implanted into porphyrin monolayers；Porphyrin Molecule ring plain structure and electronic structure abundant, device show storage performance, also show and broad application prospect potential in fields such as organic memory, organic photodetector, organic light emissions.
Description
Technical field
The present invention relates to application of the porphyrin material that end group is four sulfydryls in organic memory.
Background technique
Organic field effect tube memory is using organic material as functional activity material, is by applying just to gate electrode
To or backward voltage cause the invertibity of threshold voltage to be drifted about, to realize the storage of information.Characterize the important ginseng of storage performance
Number has mobility, switching current ratio, threshold voltage, memory window, holds time, reads and writes and wipe cycle-index, operation voltage etc..
Typical organic film FET consists of the following components: organic semiconductor layer, dielectric layer, three electrodes
(source electrode, drain electrode, grid).Wherein, source electrode and drain electrode is contacted with organic semiconductor layer, by position between grid and organic semiconductor layer
It is separated in intermediate dielectric layer.When voltage is applied in grid, charge accumulates at semiconductor layer and dielectric interface.Interface
Characteristic, interface Electronic Performance, band structure, chemical structure, roughness etc., to memory performance, as mobility, storage time,
Memory window etc. has vital influence.Organic interface material monolayer is embedded in interface application in depositing by self assembly
Reservoir (C. W. Tseng, D. C. Huang and Y. T. Tao,ACS Appl. Mater. Interfaces.,
2015,7,9767-9775).
Summary of the invention
1. the invention is characterized in that a kind of porphyrin material with abundant characteristic electron of design, four sulfydryls pass through alkyl chain
It is connected on porphyrin ring；The hydroxyl and Malaysia acid imide of porphyrin material molecule occur surface chemical reaction and form porphyrin unimolecule
Bed boundary, porphyrin ring plain are parallel to dielectric layer plane；Porphyrin material molecule structure:
N is 3 ~ 8 alkyl straight-chains in structure；
Succinimide molecular structure:。
2. above-mentioned n is 3, material TPPS4, structural formula is
。
3. the present invention provides the corproporphyrin material in SiO2Surface forms unimolecule by self assembly and surface chemical reaction
The method of layer.
4. the present invention applies the corproporphyrin interfacial monolayer in organic memory.
Detailed description of the invention
Above and other feature and advantage of the invention will be more clearly understood that in conjunction with following attached drawing and detailed description,
In:
Fig. 1 compound I nucleus magnetic hydrogen spectrum；
Fig. 2 compound II nucleus magnetic hydrogen spectrum；
Fig. 3 TPPS4 nucleus magnetic hydrogen spectrum；
Fig. 4 porphyrin material is in SiO2Surface forms the schematic diagram of molecular layer by self assembly and surface chemical reaction；
Fig. 5 organic field effect tube memory construction schematic diagram；The length of channel and it is wide be respectively 100 μm with 2000 μm；
Fig. 6 device Si/SiO2/ SAM (1)+SAM (2)/pentacene/Cu memory window.
Specific embodiment
Preferred implementation case of the invention is described in detail below, so that advantages and features of the invention can be easier to
It is readily appreciated by one skilled in the art.It elaborates below to porphyrin TPPS4 chemical synthesis.
Case study on implementation 1: the synthesis of porphyrin TPPS4:
It synthesizes as follows:
。
The synthesis of compound I
By 2.46 g (12.2 mmol) 1,3- dibromopropane, 0.5 g (4.1 mmol) parahydroxyben-zaldehyde, 0.428 g
(6.1 mmol) K2CO3 It is added in the flask equipped with 30 ml acetone, N2Protection.1 h is stirred at 80 DEG C, reaction terminates
Afterwards, stop heating, system is cooled to 0 DEG C.Revolving removes solvent, and a small amount of distilled water is added, and three times with chloroform extraction, closes
And organic phase, appropriate anhydrous MgSO is added4It is dry, after standing half an hour, it is filtered to remove MgSO4, revolving removing chloroform, chromatographic column
Separating-purifying (ethyl acetate: petroleum ether=1:4), obtains colourless oil liquid, yield 51%.1H NMR (400 MHz;
CDCl3): δ 9.89 (1H, s), 7.83 (2H, d), 7.00 (2H, d), 4.20 (2H, t), 3.61 (2H,
t), 2.36 (2H, m)。
The synthesis of compound II
0.729 g (3 mmol) compound I is added in the flask equipped with 30 ml DMF, N2It protects and is cooled to 0 DEG C.
0.342 g (3 mmol) KSAc is dissolved in 5 ml DMF, reaction system is added dropwise in 30 min, room temperature stirs 3 h.Instead
After answering, revolving removes DMF, and a small amount of water is added, and is extracted 3 times with chloroform, remaining residue in reaction flask, is added few
It is extracted 3 times after measuring water dissolution with chloroform, merges organic phase, appropriate anhydrous MgSO is added4, stand half an hour.It is filtered to remove
MgSO4, rotate and remove chloroform, chromatographic column separating-purifying (ethyl acetate: petroleum ether=1:4) obtains white solid, yield
93%。1H NMR (400 MHz; CDCl3): δ 9.91 (1H, s), 7.84 (2H, d), 7.00 (2H, d), 4.12
(2H, t), 3.09 (2H, t), 2.37 (3H, s), 2.13 (2H, m)。
Porphyrin TPPS4 synthesis
0.067 g of pyrroles (1 mmol) will newly be steamed and 0.238 g (1 mmol) compound II is dissolved in equipped with 30 ml
CH2Cl2 Flask in, N2Protection.0.114 g (1 mmol) trifluoroacetic acid is dissolved in 2 ml CH2Cl2 In, it is slowly added into anti-
System is answered, 0.170 g (0.75 mmol) tetrachloroquinone (TCQ) is added after 1.5 h are stirred in dark, flow back 1 h, instead
It should terminate.Stop heating, after system is cooled to room temperature, appropriate triethylamine is added, is filtered after standing half an hour, revolving removes molten
Agent, chromatographic column separating-purifying obtain violet solid, yield 30%.1H NMR (400 MHz; CDCl3): δ 8.87 (8H,
s), 8.13 (8H, d), 7.26 (8H, d), 4.30 (8H, t), 3.24 (8H, t), 2.43 (12H, s),
2.27 (8H, m)。
Case study on implementation 2: the preparation of self-assembled film SAM (1)+SAM (2)
Step 1: the silicon wafer having a size of 1 × 1 cm successively with acetone, ethyl alcohol, 10 min of ultrapure water sonic oscillation and is used into N2It blows
It is dry；
Step 2: by clean Si/SiO2Substrate UV-O330 min are irradiated, to be formed on its surface hydroxyl group；
Step 3: the toluene (drying) that the silicon wafer after activation is immersed in the dimaleoyl imino ruthenium triethoxysilane of 10 ml is molten
(10 in liquid-3 M), N2Protection, is heated to 75 DEG C, 36 h of self assembly, in Si/SiO2One layer of maleimide of self assembly on substrate
The self-assembled film SAM (1) of base ruthenium triethoxysilane；
Step 4: using reacting for maleimide and thiol, silicon wafer is immersed in the THF solution of the porphyrin TPPS4 of 2 ml (5 ×
10-4 M), N2Protection, is heated to 55 DEG C, 30 h of self assembly, will be with there are four sulfydryl porphyrin TPPS4 to be connected to Si/SiO2/ Malaysia
On imide propyl-triethoxysilicane surface, self-assembled film SAM (1)+SAM (2) is prepared, the big ring of mesoporphyrin is flat
Face is parallel to SiO2Surface.
Case study on implementation 3: the preparation of organic field effect tube memory
The SiO of porphyrin monolayers will be had2Substrate is put into vacuum evaporation room, is 3 x 10 in vacuum degree-4 Pa, evaporation rate
For 0.1 S-1Under 50 nm organic semiconducting materials pentance are successively deposited, be then deposited 50 nm Au as source, electric leakage
Pole, the length of transistor channel and it is wide be respectively 100 μm with 2000 μm.Device architecture is Si/SiO2/SAM (1) + SAM
(2)/pentacene (50 nm)/Au (50 nm)。
Case study on implementation 4: device performance test
Device is tested for the property using Keithley2400.Test condition is the source grid in source-drain electrode -15 V of making alive
Electrode sweeps to -25 V from 10 V, obtains initial state curve；Then add -30 V voltages to continue one second to device, then carry out source grid
Electrode sweeps to -25 V from 10 V, obtains a curve.From fig. 6, it can be seen that device shows apparent storage performance, storage
Window has 15V.
Claims (4)
1. a kind of organic memory, which is characterized in that the organic memory includes: grid, source electrode, drain electrode, dielectric layer and has
Machine semiconductor layer；Have porphyrin monolayers between the dielectric layer and organic semiconductor layer, the porphyrin monolayers it is big
Plane of a loop is parallel to the dielectric layer plane；The material of the porphyrin monolayers is that there are four the Porphyrin Molecules of sulfydryl for end group band
Material, Porphyrin Molecule structural formula are as follows:
N is 3 ~ 8 alkyl straight-chains in structure.
2. a kind of preparation method of organic memory device, which is characterized in that the described method includes: forming single point of porphyrin on dielectric layer
Sublayer；Organic semiconductor layer is formed on the porphyrin monolayers；The big plane of a loop of the porphyrin monolayers is parallel to institute
Give an account of electric layer plane.
3. according to the method described in claim 2, it is characterized in that, the formation porphyrin monolayers are by self assembly and table
Face chemical reaction is formed in dielectric layer surface.
4. according to the method described in claim 2, it is characterized in that, the length and width of the channel of the organic memory are respectively
50-200 μm and 1000-3000 μm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910844771.1A CN110491994A (en) | 2019-09-07 | 2019-09-07 | End group is application of the porphyrin material of four sulfydryls in organic storage |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910844771.1A CN110491994A (en) | 2019-09-07 | 2019-09-07 | End group is application of the porphyrin material of four sulfydryls in organic storage |
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|---|---|
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Family
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|---|---|---|---|
| CN201910844771.1A Pending CN110491994A (en) | 2019-09-07 | 2019-09-07 | End group is application of the porphyrin material of four sulfydryls in organic storage |
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|---|---|---|---|---|
| US20050019500A1 (en) * | 2003-07-25 | 2005-01-27 | The Regents Of The University Of California | Attachment of organic molecules to group III, IV or V substrates |
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- 2019-09-07 CN CN201910844771.1A patent/CN110491994A/en active Pending
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|---|---|---|---|---|
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