CN109535078A - A kind of naphthalimide derivative and solar battery - Google Patents
A kind of naphthalimide derivative and solar battery Download PDFInfo
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- CN109535078A CN109535078A CN201910017162.9A CN201910017162A CN109535078A CN 109535078 A CN109535078 A CN 109535078A CN 201910017162 A CN201910017162 A CN 201910017162A CN 109535078 A CN109535078 A CN 109535078A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
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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
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- 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
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract
The present invention discloses a kind of naphthalimide derivative and solar battery.The present invention provides a series of naphthalimide derivatives, the naphthalimide derivative is using n-type naphthalimide as basic unit, and for naphthalimide by ethylenic linkage, acetylene union or aromatic compound connection, highly polar water/alcohol-soluble group is contained in naphthalimide end.The naphthalimide derivative is water/Alcohol-soluble conjugate small molecule.Such molecule not only has excellent solubility property in environmentally friendly solvent (such as water, alcohol etc.), while can be further improved electronic transmission performance；In addition free-moving that n-type doping can be carried out to active layer material to anion, interface contact performance is improved, the transmission loss of electronics is reduced, improves the efficiency of transmission of electronics.Therefore, such naphthalimide derivative will have very big application potential as cathode interface material in terms of novel solar battery.
Description
Technical field
The present invention relates to water/Alcohol-soluble conjugate small molecule field more particularly to a kind of naphthalimide derivatives and solar energy
Battery.
Background technique
In recent years, the novel solar batteries such as organic/polymer and perovskite have obtained development at full speed, since they have
There is the features such as low cost, large area flexible manufacture, high efficiency, has obtained extensive concern.Preparing this kind of novel photovoltaic device
When, the boundary material between active layer and electrode has played vital effect, and the boundary material haveing excellent performance can be with
Effectively improve performance and the service life of photovoltaic device.
In the past, be all prepared using active metal or high temperature metal oxide method obtain boundary material, but this
Class method is uneconomical, is not suitable for low temperature preparation technique etc..
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of naphthalimide derivative and solar energy
Battery, it is intended to solve the problems, such as the preparation method of existing boundary material is uneconomical and is not suitable for low temperature preparation technique etc..
Technical scheme is as follows:
A kind of naphthalimide derivative, wherein the chemical structural formula of the naphthalimide derivative is as follows:
Wherein, X is fluorine, chlorine, methyl, methoxyl group, trifluoromethyl, itrile group, carbonyl or ester group；
The alkane or be the ethyoxyl that number of repeat unit is 1~4 that R is C1~C20；
Y is tertiary amine group base, pyridine groups, pyridine alkoxy grp, quaternary ammonium salt group, phosphonic acid base, phosphonate group or is
The sulfonic acid ammonium salt group of double type, the quaternary ammonium salt group is F, Cl, Br, I, OH to anion-、CH3COO-、CF3SO3 -、
Structural unit Ar is one of following conjugation or non-conjugated structure:
Wherein, R1、R2Linear or branched alkyl group independently selected from carbon atom number 1-30, or be end be it is phosphate-based,
The linear or branched alkyl group of the carbon atom number 1-30 of hydroxyl；
R3For H, Cl or F；Z is O, S or Se.
The naphthalimide derivative, which is characterized in that the R1、R2In independently one or more carbon atoms by oxygen
Atom replaces, and one or more hydrogen atoms are replaced by fluorine atoms.
A kind of solar battery, including cathode layer and active layer, wherein further include being set to the cathode layer and active layer
Between boundary layer, the interlayer materials be naphthalimide derivative of the present invention.
The solar battery, wherein the boundary layer with a thickness of 1-300 nanometers.
The solar battery, wherein the solar battery is organic solar batteries or Ca-Ti ore type solar energy
Battery.
The solar battery, wherein naphthalimide derivative is dissolved in water or alcohols solvent, by solution plus
The boundary layer is prepared in engineering method.
The solar battery, wherein the solution processing method is spin-coating method, spread coating, spray coating method, dip coating, roller
Coating, silk screen print method, print process or ink-jet printing.
The utility model has the advantages that naphthalimide derivative of the present invention is the water containing naphthalimide/Alcohol-soluble conjugate small molecule.It should
Class molecule not only has excellent solubility property in environmentally friendly solvent (such as water, alcohol etc.), can be further improved simultaneously
Electronic transmission performance；In addition free-moving that n-type doping can be carried out to active layer material to anion, improve interfacial contact
Performance reduces the transmission loss of electronics, improves the efficiency of transmission of electronics.Therefore, such naphthalimide derivative is as cathode circle
Plane materiel material will have very big application potential in terms of novel solar battery.
Detailed description of the invention
Fig. 1 is the structural schematic diagram for the solar battery that the present invention is just setting structure.
Fig. 2 is the structural schematic diagram of the solar battery of inverted structure of the present invention.
Fig. 3 is the structural schematic diagram of the solar battery of laminated construction of the present invention.
Fig. 4 be in embodiment based on naphthalimide derivative 1 be interlayer materials, donor polymer PCDTBT's just sets too
The Current density-voltage figure of positive energy battery.
Fig. 5 be in embodiment based on naphthalimide derivative 1 be interlayer materials, donor polymer PCDTBT's just sets too
The external quantum efficiency curve of positive energy battery.
Specific embodiment
The present invention provides a kind of naphthalimide derivative and solar battery, for make the purpose of the present invention, technical solution and
Effect is clearer, clear, and the present invention is described in more detail below.It should be appreciated that specific embodiment described herein
It is only used to explain the present invention, be not intended to limit the present invention.
The embodiment of the present invention provides a kind of naphthalimide derivative, wherein the chemical structure of the naphthalimide derivative
Formula is as follows:
Wherein, X is fluorine, chlorine, methyl, methoxyl group, trifluoromethyl, itrile group, carbonyl or ester group；
The alkane or be the ethyoxyl that number of repeat unit is 1~4 that R is C1~C20；
Y is tertiary amine group, pyridine groups, pyridine alkoxy grp, quaternary ammonium salt group, phosphonic acid base, phosphonate group or is double
The sulfonic acid ammonium salt group of subtype, the quaternary ammonium salt group is F, Cl, Br, I, OH to anion-、CH3COO-、CF3SO3 -、
Structural unit Ar is one of following conjugation or non-conjugated structure:
Wherein, R1、R2Linear or branched alkyl group independently selected from carbon atom number 1-30, or be end be it is phosphate-based,
The linear or branched alkyl group of the carbon atom number 1-30 of hydroxyl；
R3For H, Cl or F；Z is O, S or Se.
In some embodiments, the R1、R2In independently one or more carbon atoms replaced by oxygen atom, one or
Multiple hydrogen atoms are replaced by fluorine atoms.That is, the R1In one or more carbon atoms can be replaced by oxygen atom, one
Or multiple hydrogen atoms can be replaced by fluorine atoms；The R2In one or more carbon atoms can be replaced by oxygen atom, one or more
A hydrogen atom can be replaced by fluorine atoms.
In some preferred embodiments, in the naphthalimide derivative, the structural unit Ar is vinyl, alkynes
Base, naphthalimide and imide group etc., the Y are the sulfonic acid ammonium salt of tertiary amine group, quaternary ammonium salt group or double type
Group etc..
The embodiment of the invention provides a series of naphthalimide derivatives, the naphthalimide derivative is sub- with n-type naphthoyl
Amine is basic unit, and for naphthalimide by ethylenic linkage, acetylene union or aromatic compound connection, strong pole is contained in naphthalimide end
Water/alcohol-soluble group of property.The naphthalimide derivative is water/Alcohol-soluble conjugate small molecule.Such molecule is not only in environment
There is excellent solubility property in friendiy solvent (such as water, alcohol etc.), while can be further improved electronic transmission performance；In addition
It is free-moving that n-type doping can be carried out to active layer material to anion, interface contact performance is improved, the biography of electronics is reduced
Defeated loss improves the efficiency of transmission of electronics.Therefore, such naphthalimide derivative is as cathode interface material in new type solar energy
Very big application potential will be had in terms of battery.
The embodiment of the present invention also provides a kind of solar battery, including cathode layer and active layer, wherein further includes being set to
Boundary layer between the cathode layer and active layer, the interlayer materials are that naphthalimide described in the embodiment of the present invention is derivative
Object.
Compared with prior art, the embodiment of the present invention has the advantages that
(1) naphthalimide derivative of the embodiment of the present invention organic/perovskite is just being set, be inverted and laminated photovoltaic devices all
Excellent electron-transport and extraction may be implemented；Naphthalimide derivative electron transfer capabilities with higher, can prepare non-
The boundary layer of thickness dependence；
(2) this kind of highly polar naphthalimide derivative can prevent the cathodic metal of vapor deposition to the pollution of active layer, excellent
Change the Ohmic contact of active layer and metal electrode, improve the parallel resistance of device and reduce series resistance, effectively improve device
Built-in potential etc.；
(3) naphthalimide derivative of the embodiment of the present invention is dissolvable in water methanol, ethyl alcohol, alcohol/acid-mixed bonding solvent, dimethyl
In sulfoxide, water isopolarity solvent, therefore intermixing will not occur when constructing multilayer device, between boundary layer and active layer and show
As to realize environmental-friendly processing；
(4) naphthalimide derivative of the embodiment of the present invention can by the modes such as solution spin coating, printing, inkjet printing at
Film, without long-time heating or ultraviolet lighting to change its dissolubility, device preparation technology is simple and easy；
(5) since the metals such as aluminium, silver, gold have excellent air and steam stability, with the naphthoyl of the embodiment of the present invention
Imine derivative modifies high-work-function metal cathode interface, the aerial good processing stability of the composite cathode of composition, device
Stability be greatly improved；It is modified using cathode of the naphthalimide derivative to solar battery, Ke Yida
To the effect for increasing substantially device performance.
In some embodiments, the boundary layer with a thickness of 1-300 nanometers.
In some embodiments, naphthalimide derivative is dissolved in water or alcohols solvent, passes through solution processing method
The boundary layer is prepared.
In some embodiments, the solution processing method be spin-coating method, spread coating, spray coating method, dip coating, rolling method,
Silk screen print method, print process or ink-jet printing.
In the present embodiment, the solar battery can be organic solar batteries or Ca-Ti ore type solar battery.Institute
The structure for stating solar battery, which can be positive, sets structure, inverted structure or stepped construction；Wherein, in some embodiments, such as
Shown in Fig. 1, just setting structure includes the substrate stacked gradually, anode, anode modification layer, active layer, boundary layer and cathode, the boundary
Surface material is naphthalimide derivative；As shown in Fig. 2, inverted structure includes the substrate, cathode, metal oxide stacked gradually
Layer, boundary layer, active layer, anode modification layer and anode, the interlayer materials are naphthalimide derivative；As shown in figure 3, folded
Layer structure includes the substrate stacked gradually, anode, anode modification layer, active layer, boundary layer, anode modification layer, active layer, interface
Layer and cathode, the interlayer materials are naphthalimide derivative.
Below by specific embodiment, the present invention is further described.
Embodiment 1: nitrogen, the bromo- 1,8- aphthalimide of nitrogen-dimethylaminopropylamine -4-
Bromo- 1, the 8- naphthalic anhydride of 4- (5 grams, 18 mMs) is suspended in 100 milliliters of ethyl alcohol, in nitrogen protection
Under, it is added to reflux.3- dimethylaminopropylamine (2.21 grams, 21.6 mMs) is added at one time in above-mentioned reaction solution, and
It is reacted 6 hours under return stirring.Stop being added and being cooled to room temperature, the ethyl alcohol in reaction solution is spin-dried for solvent by decompression, is obtained
To crude product.Then, crude product is recrystallized in ethanol, obtains 4.88 grams of final yellow crystalline product.Its chemistry
Reaction equation is as follows:
Embodiment 2: naphthalimide derivative 1
Under nitrogen protection, by nitrogen, bromo- 1, the 8- aphthalimide of nitrogen-dimethylaminopropylamine -4- (1 gram, 2.77 mMs)
With anti-form-1, bis- (tributyl tin) ethylene of 2- (0.83 gram, 1.38 mMs) are dissolved in 50 milliliters of tetrahydrofurans, and are added four and are closed
Triphenylphosphine palladium (32 milligrams), is heated to flowing back, and reacts 24 hours.It is cooled to room temperature, tetrahydrofuran solvent passes through decompression rotation
Dry, crude product carries out recrystallization 3 times by tetrahydrofuran, obtains 512 milligrams of yellow product.The following institute of its chemical equation
Show:
Embodiment 3:6,6 '-vinyl-two (1,8- naphthalic anhydride)
Under nitrogen protection, by bromo- 1, the 8- naphthalic anhydride of 4- (3 grams, 10.8 mMs) and anti-form-1, bis- (three fourths of 2-
Ji Xi) ethylene (3.27 grams, 5.4 mMs) is dissolved in 100 milliliters of tetrahydrofurans, and is added four and is closed triphenylphosphine palladium (62.4 millis
Gram), it is heated to flowing back, and react 24 hours.It is cooled to room temperature, tetrahydrofuran solvent is spin-dried for by decompression, and crude product passes through two
Chloromethanes carries out column Chromatographic purification, and is recrystallized by chloroform, obtains 1.63 grams of Off-white product.Its chemistry is anti-
Answer equation as follows:
Embodiment 4: naphthalimide derivative 1
6,6 '-vinyl-two (1,8- naphthalic anhydride) (1.4 grams, 3.3 mMs) are suspended in 100 milliliters of DMF
In, under nitrogen protection, it is added to reflux.3- dimethylaminopropylamine (1.01 grams, 9.9 mMs) is added at one time above-mentioned reaction
In solution, and reacted 12 hours under return stirring.Stop being added and being cooled to room temperature, product is precipitated, and filters and removes solution, obtains
To crude product.Then, crude product is recrystallized in tetrahydrofuran, obtains 776 milligrams of final yellow crystalline product.
Its chemical equation is as follows:
Embodiment 5: nitrogen, nitrogen-dimethylaminopropylamine -4- acetylene -1,8- aphthalimide
Under nitrogen protection, by nitrogen, and bromo- 1, the 8- aphthalimide of nitrogen-dimethylaminopropylamine -4- (2 grams, 5.54 mmoles
You), trimethylsilyl acetylene (707 milligrams, 7.2 mMs), two (triphenylphosphines) close palladium chloride (42 milligrams, 0.06 mM),
Triphenylphosphine (157 milligrams, 0.6 mM), cuprous iodide (1.05 grams, 5.54 mMs) are dissolved in 50 milliliters of tetrahydrofurans
In, stirring and dissolving simultaneously deaerates 20 minutes, is then added at one time 10 milliliters of triethylamine, is heated to flowing back, and reacts 24 hours.Stop
It only heats and is cooled to room temperature, solvent is spin-dried for by Rotary Evaporators, and gained crude product carries out column chromatography by methylene chloride and mentions
Pure (note: needing to carry out column chromatography in the silica gel that triethylamine alkalizes), obtains product of the end containing trimethylsilyl；It should
Product is dissolved in tetrahydrofuran, and suitable tetrabutyl ammonium fluoride is added, and is stirred at room temperature one hour, water is then added, and use
Methylene chloride extracts three times, and washing three times, it is dry to be put into anhydrous magnesium sulfate.Dichloromethane solvent is spin-dried for by Rotary Evaporators,
Gained final product recrystallizes 3 times in tetrahydrofuran, obtains 917 milligrams of final goal product.Its chemical equation is as follows
It is shown:
Embodiment 6: naphthalimide derivative 2
Under nitrogen protection, by nitrogen, and bromo- 1, the 8- aphthalimide of nitrogen-dimethylaminopropylamine -4- (1 gram, 2.77 mmoles
You), nitrogen, nitrogen-dimethylaminopropylamine -4- acetylene -1,8- aphthalimide (0.85 gram, 2.77 mMs), two (triphenylphosphines)
It closes palladium chloride (21 milligrams, 0.03 mM), triphenylphosphine (78.5 milligrams, 0.3 mM), and cuprous iodide (0.53 gram, 2.77
MM) be dissolved in 100 milliliters of tetrahydrofurans, stirring and dissolving simultaneously deaerates 20 minutes, is then added at one time 5 milli of triethylamine
It rises, is heated to flowing back, and react 24 hours.Stop heating and being cooled to room temperature, solvent is spin-dried for by Rotary Evaporators, and gained is thick
Product carries out column Chromatographic purification (note: needing to carry out column chromatography in the silica gel that triethylamine alkalizes) by methylene chloride.Dichloro
Methane solvent is spin-dried for by Rotary Evaporators, and gained final product recrystallizes 3 times in tetrahydrofuran, obtains final goal product
1.06 gram.
Embodiment 7: naphthalimide derivative 3
Under nitrogen protection, naphthalimide derivative 1 (0.5 gram, 0.85 mM) is dissolved in 25 in pressure-resistant reaction flask
In milliliter tetrahydrofuran, 10 milliliters of bromoethane are added, is heated to 50 degrees Celsius, and reacted 24 hours, with the progress of reaction,
Along with the precipitation of solid.It is cooled to room temperature, crude product is obtained by filtration.Crude product is recrystallized in methyl alcohol again, is obtained most
582 milligrams of final product.It reacts as follows:
Embodiment 8: naphthalimide derivative 4
Under nitrogen protection, alcohol-soluble small molecule 1 (0.6 gram, 1 mM) is dissolved in 30 milliliters of tetrahydrofurans, then plus
Enter 5 grams of 1,3-propane sultone, be heated to flowing back, and react 24 hours, with the progress of reaction, along with the precipitation of solid；
During the reaction, when there is solid precipitation, suitable acetonitrile solvent is added into reaction system, until solid dissolves.It is cooling
To room temperature, solvent in reaction solution is spin-dried for by Rotary Evaporators, a small amount of methanol dissolution is being added into crude product, then by first
Alcoholic solution Precipitation in methylene chloride.Crude product is recrystallized in methyl alcohol again, obtains 525 milligrams of final product.Its
Reaction is as follows:
Illustrate by taking naphthalimide derivative 1 as an example below naphthalimide derivative of the invention as boundary layer it is organic too
Application (being shown in Table 1 and attached drawing 4,5) in positive energy battery.
Embodiment 9: the preparation and representation of organic solar batteries
By ITO electro-conductive glass, square resistance~20 Ω/ is precut into 15 millimeters × 15 millimeters square pieces.Successively with third
Ketone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasonic cleaning, it is spare that nitrogen purging is placed on constant temperature oven.
Before use, the net piece of ITO is in oxygen plasma etch instrument with plasma bombardment 10 minutes.PEDOT:PSS aqueous dispersions
(1wt%) is purchased from Bayer company, is determined with a thickness of 40 nanometers by solution concentration and revolving speed with sol evenning machine (KW-4A) high speed spin coating
It is fixed, it is surveyed and is monitored with surface profiler (Tritek company Alpha-Tencor500 type).After film forming, in 130 degrees Celsius of thermal annealings
10 minutes, to remove residual solvent.Organic solar batteries active layer material PCDTBT (PC71BM is as receptor) is placed in dry
It weighs, is then continued in the glove box of nitrogen protection in net sample bottle, protected in glove box for high pure nitrogen to maintain hypoxemia
The state of low humidity.The polymer for being used to prepare active layer and PC71BM are mixed to be placed on mixing platform with solvent toluene and stirred
Mixing is completely dissolved material.The ITO substrate for being coated with anode buffer layer being dried in vacuo is moved into glove box and carries out polymer
The process of the spin coating of active layer, spin coating is identical as anode buffer layer.Keep ITO layer exposed with the side that sharp instrument scrapes group diaphragm,
As the anode of device after electrode is deposited.Dry and remove remaining organic solvent.Organic solar batteries active layer thickness is
80 nanometers.Film thickness is measured with surface profiler.Naphthalimide derivative 1 is dissolved in methyl alcohol (be added volume fraction be thousand points
One of acetic acid as cosolvent), be configured to the solution of 1 mg/ml concentration, with 0.45 micron membrane filter filtering.Use sol evenning machine
A thin layer is generated on the ITO substrate for getting rid of organic solar batteries active layer material and PEDOT:PSS layers respectively, with a thickness of
5 nanometers.Aluminium electrode is vaporized on vacuum degree in vacuum coating equipment and reaches 3 × 10-4It is completed when Pa or less.Plated film rate and each layer electrode
Thickness by quartz vibrator film thickness monitor (STM-100 type, Sycon company) monitor in real time.The light emitting region of device is by mask
The region that covering is interacted with ITO is determined as 0.16 square centimeter.All preparation process are providing the gloves of nitrogen inert atmosphere
It is carried out in case.Solar cell properties are in simulated solar irradiation (AM 1.5G100mW/cm2) under measure.For the display present invention
The effect of used boundary layer, using not plus boundary layer device as a comparison.Measurement result is as shown in attached drawing 4,5 and table 1；
Wherein, table 1 is solar cell properties data.
Table 1
Solar battery structure: ITO/PEDOT:PSS/PCDTBT:PC71BM/ boundary layer/Al
As it can be seen from table 1 compared to the solar battery of no boundary layer, using naphthalimide derivative 1 as boundary layer
The short circuit current variation of the solar battery of preparation is little, but open-circuit voltage and fill factor increase, the energy of final the latter
Amount transfer efficiency tool is greatly improved；To the raising of solar cell properties when other naphthalimide derivatives are as boundary layer
Effect and naphthalimide derivative 1 are almost the same, numerous to list herein, illustrate that solar battery of the invention is that one kind has
The embellishing cathode interface material of the solar battery of very big potentiality.
In conclusion a kind of naphthalimide derivative provided by the invention and solar battery, of the invention is sub- containing naphthoyl
Embellishing cathode interface material of the n-type water/alcohol-soluble small molecule (the i.e. described naphthalimide derivative) of amine as solar battery
When, interface dipole effect can be formed between light absorption active layer and cathode, reduce cathode effective work function；Meanwhile it is this kind of small
Molecule electron transfer capabilities with higher, to be effectively facilitated the transmission and extraction of electronics.Small soluble molecules of the invention
Solution is in methanol, ethyl alcohol, alcohol/acid-mixed bonding solvent, dimethyl sulfoxide, water isopolarity solvent, therefore when constructing multilayer device, boundary
Intermixing phenomenon will not occur between surface layer and active layer, to realize environmental-friendly processing.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (7)
1. a kind of naphthalimide derivative, which is characterized in that the chemical structural formula of the naphthalimide derivative is as follows:
Wherein, X is fluorine, chlorine, methyl, methoxyl group, trifluoromethyl, itrile group, carbonyl or ester group；
The alkane or be the ethyoxyl that number of repeat unit is 1~4 that R is C1~C20；
Y is tertiary amine group, pyridine groups, pyridine alkoxy grp, quaternary ammonium salt group, phosphonic acid base, phosphonate group or is double type
Sulfonic acid ammonium salt group, the quaternary ammonium salt group to anion be F, Cl, Br, I, OH-、CH3COO-、CF3SO3 -、
Structural unit Ar is one of following conjugation or non-conjugated structure:
Wherein, R1、R2Linear or branched alkyl group independently selected from carbon atom number 1-30, or be end be phosphate-based, hydroxyl
Carbon atom number 1-30 linear or branched alkyl group；
R3For H, Cl or F；Z is O, S or Se.
2. naphthalimide derivative according to claim 1, which is characterized in that the R1、R2In it is independently one or more
Carbon atom is replaced by oxygen atom, and one or more hydrogen atoms are replaced by fluorine atoms.
3. a kind of solar battery, including cathode layer and active layer, which is characterized in that further include being set to the cathode layer and work
Property layer between boundary layer, the interlayer materials be the described in any item naphthalimide derivatives of claim 1-2.
4. solar battery according to claim 3, which is characterized in that the boundary layer with a thickness of 1-300 nanometers.
5. solar battery according to claim 3, which is characterized in that the solar battery is organic solar batteries
Or Ca-Ti ore type solar battery.
6. solar battery according to claim 3, which is characterized in that naphthalimide derivative is dissolved in water or alcohols
In solvent, the boundary layer is prepared by solution processing method.
7. solar battery according to claim 6, which is characterized in that the solution processing method be spin-coating method, spread coating,
Spray coating method, dip coating, rolling method, silk screen print method, print process or ink-jet printing.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109950404A (en) * | 2019-03-30 | 2019-06-28 | 南昌大学 | A method of improving perovskite solar battery efficiency and hydrothermal stability |
| CN113178550A (en) * | 2021-04-30 | 2021-07-27 | 桂林理工大学 | Aluminum composite electrode, preparation method and application thereof, and dual-ion battery |
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| CN113178550A (en) * | 2021-04-30 | 2021-07-27 | 桂林理工大学 | Aluminum composite electrode, preparation method and application thereof, and dual-ion battery |
| CN115611862A (en) * | 2022-10-12 | 2023-01-17 | 南昌航空大学 | A-D-A type amino naphthalimide micromolecule cathode interface layer and preparation method thereof |
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