CN105130988B - It is a kind of Li sub- Xing perylene diimide class materials and preparation method and its organic memory device - Google Patents
It is a kind of Li sub- Xing perylene diimide class materials and preparation method and its organic memory device Download PDFInfo
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- CN105130988B CN105130988B CN201510465372.6A CN201510465372A CN105130988B CN 105130988 B CN105130988 B CN 105130988B CN 201510465372 A CN201510465372 A CN 201510465372A CN 105130988 B CN105130988 B CN 105130988B
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- 239000000463 material Substances 0.000 title claims abstract description 36
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical class C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000005466 alkylenyl group Chemical group 0.000 claims abstract description 3
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960005222 phenazone Drugs 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 238000001556 precipitation Methods 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000001291 vacuum drying Methods 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 239000012298 atmosphere Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 210000003739 neck Anatomy 0.000 claims description 6
- 238000004528 spin coating Methods 0.000 claims description 5
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 3
- 238000007738 vacuum evaporation Methods 0.000 claims description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical class CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 abstract description 6
- 238000011105 stabilization Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000005669 field effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 10
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 7
- 230000005611 electricity Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- HVOYZOQVDYHUPF-UHFFFAOYSA-N CNCCN(C)C Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N O=C(c1ccc(-c(cc2)c3c4c2C(O2)=O)c5c1c1ccc5-c3ccc4C2=O)OC1=O Chemical compound O=C(c1ccc(-c(cc2)c3c4c2C(O2)=O)c5c1c1ccc5-c3ccc4C2=O)OC1=O CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- -1 perylene acid anhydrides Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VACCAVUAMIDAGB-UHFFFAOYSA-N sulfamethizole Chemical compound S1C(C)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 VACCAVUAMIDAGB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Semiconductor Memories (AREA)
Abstract
The invention particularly discloses a kind of Li sub- Xing perylene diimide class materials and preparation method and its organic memory device.The chemical structural formula of the electric bi-stable material is as follows：Wherein R1、R2Selected from C1~C6Alkyl or phenyl one kind.R3It is one kind of Cl, Br, I.The present invention is successfully prepared electric bi-stable WORM type devices, with preferable on-off ratio, suitable read-write voltage, and duration more long.Meanwhile, raw material of the invention is easy to get, and synthesis is simple, and device making technics are ripe, device performance stabilization.Make the material of perylene diimide derivative shows good heat endurance, excellent photoelectric properties and characteristic easy to process so that it has a wide range of applications in fields such as organic solar batteries, organic field effect tube and organic electrical storage devices.
Description
Technical field
The present invention relates to a kind of electricity storage bistable material, belong to information material technical field.
Background technology
Since Kardos is since the mono- perylene system derivative of synthesis in 1913, people start the synthesis of Dui perylenes system derivative
Many discussions have been carried out with property.Perylene diimide is the knot that a class has very big π-pi-electron conjugated structure and rigid plane
The material of structure.Have strong absorption in visible-range, fluorescence quantum yield is high, with excellent photostability, heat endurance,
Electron transport ability.Last decade Sui perylene diimide and its derivative and is subject to increasing scientific research work as organic photoelectrical material
The concern of author.Perylene diimide derivative has larger conjugated system, has stronger active force between molecule.Yi Ban perylene acyls
The derivative of the imines poor shortcoming of dissolubility in organic solvent.Mu Qian perylene diimides itself and derivative is used as organic photoelectric material
Material is quite varied in the application of the aspects such as field-effect transistor (OFET), organic solar batteries (OPV).
In terms of Organic Electricity storage, Li Xing perylene diimides and its derivative are but seldom set foot in , perylene diimide derivatives
It is that a kind of typical n-type material has larger planar structure, there is electron affinity energy and electricity higher as electron acceptor
Sub- transmittability.ShoukeYan seminars report Li Yong perylene diimides derivatives and prepare tool with another monomer terthienyl
There is the functional polymer of D-A type structure as organic accumulation layer, with excellent storage performance.Yin Ci perylene diimides and its derivative
Thing also has the potential quality of further research in terms of Organic Electricity storage.
Small molecule perylene diimides and its derivative have special advantage, particularly ionic as organic memory material
Perylene diimide derivatives, with being easily-synthesized, structure-controllable, excellent photostability, favorable solubility, heat endurance are high, excellent
Electron transport ability more and filming performance.The spin-coating film on ITO, is fabricated to " electrode/organic film/electrode " three of classics
Mingzhi's structure.Under positive and negative scanning voltage, the write-once for forming stabilization repeatedly reads (WORM) type storage effect, and when continuing
Between stabilization, repeatability preferably.
The content of the invention
Technical problem：It is an object of the invention to provide a kind of Li sub- Xing perylene diimide class materials and preparation method and its organic
Memory device, the material is a kind of this kind of structure with very big π-pi-electron conjugated structure and rigid plane of Ji Yu perylene diimides
Material and its derivant material.The big plane construction unit has and has strong absorption, fluorescence quantum yield in visible-range
Height, with excellent photostability, heat endurance, the advantages of electron transport ability is strong.Using the construction unit, developing one is
Arrange from sub- type perylene diimide derivant material, these materials show electron affinity can be strong, it is excellent heat endurance, good
Photoelectric properties and characteristic easy to process cause that it has extensively in organic field effect tube and organic electrical storage device field
General application prospect.
Technical scheme：In order to achieve the above object, it is of the invention a kind of Li sub- Xing perylene diimide class materials, with following knot
Structure：
Wherein R1、R2It is C1~C6Alkyl or phenyl one kind, R3It is one kind of Cl, Br, I.
The preparation method is comprised the following steps：
1) with quinoline as solvent, in nitrogen atmosphere, under the conditions of 140~160 DEG C, N, N- dimethyl-ethylenediamine Yu perylene acid anhydrides enter
Row substitution reaction, obtains dark red solid；
The chemical structural formula of described dark red solid is：
2) iodomethane and step 1) the middle dark red solid reaction for obtaining, prepare described Li sub- Xing perylene diimide class materials
Material, the i.e. material of electric bi-stable.
The method for preparing electrical storage device includes step：
1) the leafing subtype perylene diimide materials of spin coating one on indium tin oxide electro-conductive glass, prepared one layer organic
Film：
2) one layer of aluminium electrode of vacuum evaporation on organic film again, eventually forms a kind of " electrode/organic film/electrode "
The electrical storage device structure of sandwich.
Beneficial effect：The present invention creatively will from sub- type perylene diimide it is this kind of with π-pi-conjugated rigid planar structure material
Material, creatively uses during organic electronic stores its device, successfully prepares a kind of stabilization WORM type Organic Electricities high, reproducible
Memory device.Raw material of the present invention is easy to get, and organic synthesis is easy, and dissolubility is good, it is easy to process, device stability is good, therefore
It has a wide range of applications in organic electrical storage device field.
Brief description of the drawings
Fig. 1 is based on Li sub- Xing perylene diimide derivative PBI (R1=C2H5, R2=CH3, R3=I) proton nmr spectra.
Fig. 2 is based on Li sub- Xing perylene diimide derivative PBI (R1=C2H5, R2=CH3, R3=I) prepare electric bi-stable
Organic electrical storage device schematic diagram.
Fig. 3 is based on Li sub- Xing perylene diimide derivative PBI (R1=C2H5, R2=CH3, R3=I) prepare electric bi-stable
Organic electrical storage device current -voltage curve figure.
Fig. 4 is based on Li sub- Xing perylene diimide derivative PBI (R1=C2H5, R2=CH3, R3=I) prepare electric bi-stable
Organic electrical storage device electric current under constant voltage to the time stabilization figure.
Wherein, 1. aluminium electrode；2. organic film；3.ITO；4. glass.
Specific embodiment
The method for preparing above-mentioned electric bi-stable material, specifically includes following steps：
(1) in N2Under the conditions of , Jiang perylene tetracid dianhydride, N, N- dimethyl-ethylenediamines and quinoline in molar ratio 1:16:34 ratio
Example mixing, 140 DEG C are heated to by mixed solution, are reacted 24 hours.Uniform temperature is down to, methyl alcohol is added, continues to flow back.It is cooled to
Room temperature, precipitation filtering, methyl alcohol washing, vacuum drying obtains dark red solid.
(2) by dark red solid obtained above, it is dissolved in toluene, adds iodomethane (8 times of equivalents), flows back 5 hours.It is cold
But to room temperature, filtering precipitation is washed with ether, is vacuum dried, and obtains above-mentioned electric bi-stable material.
The preparation method of organic memory device, comprises the following steps：
(1) the above-mentioned electric bi-stable material of spin coating on indium tin oxide electro-conductive glass (ITO, Indium Tin Oxides),
Obtain one layer of organic film；
(2) one layer of aluminium electrode of vacuum evaporation on organic film, forms a kind of " electrode/organic film/electrode " sandwich device
Part structure.
Technical scheme is further illustrated below by embodiment, to be better understood from present disclosure.
Embodiment 1：
Synthetic route is as follows：
1) weigh 2.00g compounds A and 7.05gN, N- dimethyl diethylamine are placed in bottle with two necks, vacuumize, drum nitrogen is anti-
It is multiple three times, N2In atmosphere, 20mL quinoline is added, be heated to 140 DEG C, reacted 24 hours.50 DEG C are cooled to, 30mL methyl alcohol is added,
After continuing to be heated to reflux half an hour, room temperature is cooled to.Precipitation filtering, methyl alcohol washing, vacuum drying obtains red solid B.
2) weigh red 0.50g solids B and 1.03g NBB to be dissolved in 30mL toluene, flow back 5 hours.It is cooled to room temperature,
Precipitation is filtered, is washed with ether, be vacuum dried, obtain dark red solid C.
Embodiment 2：
Synthetic route is as follows：
1) 2.00g compounds A, 7.05gN are weighed, N- dimethyl diethylamine is placed in bottle with two necks, vacuumizes, drum nitrogen is anti-
It is multiple three times.N2In atmosphere, 20mL quinoline is added, under the conditions of 140 DEG C, reacted 24 hours.50 DEG C are cooled to, 30mL methyl alcohol is added,
Continue to be cooled to room temperature after being heated to reflux half an hour, filtering precipitation, methyl alcohol washing, vacuum drying obtains red solid B.
2) take 0.50g red solids B to be dissolved in 30mL toluene, add 0.82g bromoethanes, flow back 5 hours.It is cooled to room
Temperature, filtering precipitation, is washed with ether, is vacuum dried, and obtains dark red solid D.
Embodiment 3：
Synthetic route is as follows：
1) 2.00g compound A, 7.05g N, N- dimethyl diethylamine is taken in bottle with two necks, is vacuumized, drum nitrogen repeatedly three
It is secondary, N2In atmosphere, 20mL quinoline is added.140 DEG C are heated to, are reacted 24 hours.Cooling, adds 30mL methyl alcohol, flows back half an hour,
It is subsequently cooled to room temperature.Precipitation filtering, methyl alcohol washing, vacuum drying obtains red solid B.
2) take 0.50g red solids B to be dissolved in 30mL toluene, be subsequently adding 1.07g iodomethane, flow back 5 hours.It is cooled to
Room temperature, precipitation is filtered, and is washed with ether, vacuum drying, to dark red solid E.
Embodiment 4：
By taking compound E prepared by example 3 as an example, the electrical storage device of sandwich structure is prepared.Preparation procedure is as follows：In nitrogen
In the glove box that atmosphere is enclosed, 4.00mg compounds E is weighed in 10mL bottles, add 5mL methyl alcohol, room-temperature dissolution 24 hours.Then
Filtered with 0.22 micron membrane filter, obtain 0.8mg/mL PBI solution.ITO uses scavenger specially, deionized water, acetone, second successively
Alcohol is respectively washed 15 minutes in ultrasonic wave, nitrogen drying, in 120 DEG C of vacuum drying ovens toast 30 minutes it is standby.With 500rpm/
Organic active layer film is prepared with rotating speed spin coating in 800rpm/30 seconds within 10 seconds, the thickness for preparing film is 20nm.Then nitrogen atmosphere
Middle annealing, the time is 30min.Finally, vacuum is 3 × 10-4During Pa, evaporating Al electrode, the thickness for being deposited with layer is 100nm, is obtained
To the organic electrical storage device of WORM types.
Knowable to from Fig. 3 and Fig. 4, PBI, as active storing material, prepares threshold voltage in organic electrical storage device
It is 3.7V, on-off ratio 1.2 × 10-4, the duration is up to 10000s.Yin Ci perylene diimide class materials are made high performance Organic Electricity
Memory device, realizes the WORM types storage effect that write-once repeatedly reads, and duration stabilization, repeatability preferably, is hoped
Organic field of storage has very big application prospect.
Claims (3)
1. it is a kind of Li sub- Xing perylene diimide class materials, it is characterised in that the material has following structure：
Wherein R1、R2It is C1~C6Alkyl or phenyl one kind, R3It is one kind of Cl, Br, I.
2. a kind of preparation method Li sub- Xing perylene diimide class materials as claimed in claim 1, it is characterised in that:
(1) R is worked as1Take ethyl, R2It is butyl, R3When taking Br, its syntheti c route and preparation method are：
A) weigh 2.00g compounds A and 7.05gN, N- dimethyl diethylamine are placed in bottle with two necks, vacuumize, drum nitrogen repeatedly three
It is secondary, N2In atmosphere, 20mL quinoline is added, be heated to 140 DEG C, reacted 24 hours, be cooled to 50 DEG C, add 30mL methyl alcohol, continued
After being heated to reflux half an hour, room temperature is cooled to, precipitation filtering, methyl alcohol washing, vacuum drying obtains red solid B,
B) weigh red 0.50g solids B and 1.03g NBB to be dissolved in 30mL toluene, flow back 5 hours, be cooled to room temperature, will be heavy
Form sediment and filter, washed with ether, be vacuum dried, obtain dark red solid C,
(2) R is worked as1、R2Take ethyl, R3When taking Br, its syntheti c route and preparation method are：
A) weigh 2.00g compound A, 7.05g N, N- dimethyl diethylamine to be placed in bottle with two necks, vacuumize, drum nitrogen repeatedly three
It is secondary, N2In atmosphere, 20mL quinoline is added, under the conditions of 140 DEG C, reacted 24 hours, be cooled to 50 DEG C, add 30mL methyl alcohol, continued
Room temperature is cooled to after being heated to reflux half an hour, filtering precipitation, methyl alcohol washing, vacuum drying obtains red solid B,
B) take 0.50g red solids B to be dissolved in 30mL toluene, add 0.82g bromoethanes, flow back 5 hours, be cooled to room temperature, mistake
Filter precipitation, is washed with ether, is vacuum dried, and obtains dark red solid D,
(3) R is worked as1Take ethyl, R2It is methyl, R3When taking I, its syntheti c route and preparation method are：
1) 2.00g compound A, 7.05g N, N- dimethyl diethylamine is taken in bottle with two necks, is vacuumized, rouse nitrogen repeatedly for three times, N2
In atmosphere, 20mL quinoline is added, be heated to 140 DEG C, reacted 24 hours, cooling adds 30mL methyl alcohol, flows back half an hour, then
Room temperature is cooled to, precipitation filtering, methyl alcohol washing, vacuum drying obtains red solid B,
2) take 0.50g red solids B to be dissolved in 30mL toluene, be subsequently adding 1.07g iodomethane, flow back 5 hours, be cooled to room
Temperature, precipitation is filtered, and is washed with ether, vacuum drying, to dark red solid E.
3. a kind of method for preparing electrical storage device Li sub- Xing perylene diimide class materials as claimed in claim 1, its feature exists
Include step in the method for preparing electrical storage device：
1) the leafing subtype perylene diimide materials of spin coating one on indium tin oxide electro-conductive glass, are obtained one layer of organic film：
2) one layer of aluminium electrode of vacuum evaporation on organic film again, eventually forms a kind of " electrode/organic film/electrode " sandwich
Electrical storage device structure.
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| CN108832000B (en) * | 2018-06-19 | 2021-11-05 | 南京邮电大学 | Ternary polymer solar cell |
| CN111072657B (en) * | 2019-12-25 | 2022-02-11 | 青岛科技大学 | Fluorescent probe for detecting activity of acetylcholinesterase and synthetic method and application thereof |
| CN113178550B (en) * | 2021-04-30 | 2022-08-16 | 桂林理工大学 | Aluminum composite electrode, preparation method and application thereof, and dual-ion battery |
| CN113637015A (en) * | 2021-08-10 | 2021-11-12 | 南昌航空大学 | Quaternary ammonium salt functionalized perylene diimide micromolecule interface layer and preparation method thereof |
| CN114380826B (en) * | 2022-01-21 | 2024-02-23 | 吉林大学 | Perylene porous organic salt material with stable light and heat properties, and preparation method and application thereof |
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