CN107814724A - Electron transport material and preparation method thereof and perovskite solar cell - Google Patents
Electron transport material and preparation method thereof and perovskite solar cell Download PDFInfo
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- CN107814724A CN107814724A CN201710947979.7A CN201710947979A CN107814724A CN 107814724 A CN107814724 A CN 107814724A CN 201710947979 A CN201710947979 A CN 201710947979A CN 107814724 A CN107814724 A CN 107814724A
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- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/50—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
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- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- C07D209/56—Ring systems containing three or more rings
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- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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Abstract
The present invention relates to photovoltaic art, specifically discloses a kind of electron transport material, and it includes the compound of below formula：Wherein, ring F represents fullerene；R1 represents following substituent：N1 is selected from 1~2；R2 represents following substituent：‑NH‑CH2‑CH2‑NR’2、‑NH‑CH2‑CH2‑OR’；R ' represents H or C1‑C3Alkyl；N2 is selected from 1~4.Above-mentioned electron transport material, not only with electric transmission function, while also there is the dual-use function of calcium titanium ore bed passivation.It can strengthen the solidification of halogens in calcium titanium ore bed, the defects of so can both having reduced calcium titanium ore bed state, the stability of calcium titanium ore bed can also be improved；Hole can also be preferably obstructed simultaneously, it is compound to prevent that the electronics in the photohole and electron transfer layer of calcium titanium ore bed from occurring, improves the contact with calcium titanium ore bed, is advantageous to the stability of perovskite solar cell, is then also beneficial to improve photoelectric transformation efficiency.Present invention also offers a kind of preparation method of electron transport material and perovskite solar cell.
Description
Technical field
The present invention relates to field of photovoltaic technology, more particularly to a kind of electron transport material and preparation method thereof and perovskite
Solar cell.
Background technology
Perovskite solar cell is a kind of novel solar battery occurred in recent years, and it is by perovskite light absorbent system
Into.Perovskite light absorbent has excellent photoelectric properties, high carrier mobility (monocrystalline 66cm2V-1s-1, polycrystalline
11.6cm2V-1s-1) including long electron hole diffusion length (monocrystalline is more than 175 μm, and polycrystalline is more than 1 μm), high absorptivity and width
Wide light absorption range (covering whole visible region) so that perovskite area of solar cell is rapidly sent out in a short time
Exhibition.
At present, the Organic Electron Transport Material used in perovskite solar cell, essentially fullerene derivate material
Material.The machine electron transport material of common are has：PCBM、ICMA、ICBA.
But PCBM, ICMA, ICBA these Organic Electron Transport Materials, manufactured perovskite solar cell stability
Deficiency.
The content of the invention
Based on this, there is provided a kind of new electron transport material.
A kind of electron transport material, the electron transport material include the compound of below formula：
Wherein, ring F represents fullerene；
R1 represents following substituent：
N1 is selected from 1~2；
R2 represents following substituent：
-NH-CH2-CH2-NR’2、-NH-CH2-CH2-OR’；R ' represents H or C1-C3Alkyl；
N2 is selected from 1~4.
Above-mentioned electron transport material, not only with electric transmission function, while also there is the dual work(of calcium titanium ore bed passivation
Energy.Above-mentioned electron transport material, the solidification of halogens in calcium titanium ore bed can be strengthened, so can both reduce calcium titanium ore bed
The defects of state, the stability of calcium titanium ore bed can also be improved；Hole can also be preferably obstructed simultaneously, prevents the light of calcium titanium ore bed
Raw hole and the electronics generation in electron transfer layer are compound, improve the contact with calcium titanium ore bed, are advantageous to perovskite solar-electricity
The stability in pond, then it is also beneficial to improve photoelectric transformation efficiency.
In one of the embodiments, the electron transport material is the compound of below formula：
Present invention also offers a kind of preparation method of electron transport material.
A kind of preparation method of electron transport material, comprises the following steps：
Under an inert atmosphere, the first reactant is mixed with the second reactant and in 60 DEG C~85 DEG C heating responses；Then
Product is separated, obtains electron transport material；
First reactant is selected from the compound of below formula：
Wherein, ring F represents fullerene；
R1 represents following substituent：
N1 is selected from 1~2；
Second reactant is selected from NH2-CH2-CH2-NR’2、NH2-CH2-CH2-OR’；R ' represents H or C1-C3Alkyl.
The preparation method of above-mentioned electron transport material, it is simple to operation.
In one of the embodiments, second reactant is selected from ethylenediamine, monoethanolamine, N- methyl ethylenediamines, N, N-
One or more in dimethyl-ethylenediamine or 2- methoxyethyl amines.
In one of the embodiments, the time of the reaction is 5min~30min.
In one of the embodiments, the temperature of the reaction is 60 DEG C~85 DEG C.
In one of the embodiments, the inert atmosphere is nitrogen atmosphere or argon gas atmosphere.
Present invention also offers a kind of perovskite solar cell.
A kind of perovskite solar cell, including electron transfer layer；The electron transfer layer includes provided by the present invention
Electron transport material.
Above-mentioned perovskite solar cell, due to including electron transport material provided by the present invention in electron transfer layer；
So electron transfer layer also has the dual-use function to calcium titanium ore bed passivation, the solidification that can strengthen halogens in calcium titanium ore bed is made
With, the defects of so can both having reduced calcium titanium ore bed state, the stability of calcium titanium ore bed can also be improved；While electron transfer layer is also
Hole can preferably be obstructed, it is compound to prevent that electronics in the photohole and electron transfer layer of calcium titanium ore bed from occurring, improve with
The contact of calcium titanium ore bed, be advantageous to improve photoelectric transformation efficiency.
In one of the embodiments, the thickness of the electron transfer layer is 20nm~100nm.
In one of the embodiments, the perovskite solar cell is inverted structure.
Brief description of the drawings
Fig. 1 is the structural representation of the perovskite solar cell of an embodiment of the present invention.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, it is right below in conjunction with embodiment
The present invention is further elaborated.It should be appreciated that embodiment described herein is only to explain the present invention,
It is not intended to limit the present invention.
Unless otherwise defined, all of technologies and scientific terms used here by the article is with belonging to technical field of the invention
The implication that technical staff is generally understood that is identical.Term used in the description of the invention herein is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.Term as used herein " and/or " include one or more
The arbitrary and all combination of related Listed Items.
A kind of electron transport material, include the compound of below formula：
Wherein, ring F represents fullerene；
R1 represents following substituent：
N1 is selected from 1~2；
R2 represents following substituent：
-NH-CH2-CH2-NR’2、-NH-CH2-CH2-OR’；R ' represents H or C1-C3Alkyl；It is understood that two
R ' can be with identical, can also be different.
N2 is selected from 1~4.
Wherein, n1 represents the number of R1 substituents, and n2 represents the number of R2 substituents.
Further, ring F can represent fullerene C60, fullerene C70, fullerene C76Or fullerene C84.In the present invention,
The position of substitution of R1 and R2 on ring F is random, is not particularly limited.
Preferably, electron transport material is selected from the compound of below formula：
It is highly preferred that electron transport material is selected from following compound：
Above-mentioned electron transport material, because the N in the amido that is introduced into can provide lone pair electrons to the halogen in perovskite
Vacancy, the defects of having replenished calcium titanium ore bed；And chemical bond is formed to improve its passivation, therefore above-mentioned electricity with perovskite surface
Sub- transmission material, not only make electron transport material that there is electric transmission function, while also there is the dual work(of passivation calcium titanium ore bed
Can, the solidification of halogens in calcium titanium ore bed can be strengthened, the defects of so can both having reduced calcium titanium ore bed state, can also carry
The stability of high calcium titanium ore bed；Hole can also be preferably obstructed simultaneously, prevents the photohole and electric transmission of calcium titanium ore bed
Electronics generation in layer is compound, improves the contact with calcium titanium ore bed, is advantageous to improve photoelectric transformation efficiency.
Present invention also offers a kind of preparation method of above-mentioned electron transport material.
A kind of preparation method of electron transport material, comprises the following steps：
S1, under an inert atmosphere, the first reactant is mixed with the second reactant and in 60 DEG C~85 DEG C heating responses.
Wherein, the first reactant is the fullerene derivate with electric transmission function.
Specifically, the first reactant is selected from the compound of below formula：
Wherein, ring F represents fullerene；
R1 represents following substituent：
N1 is selected from 1~2.
The effect of second reactant is to provide electron rich group.
Specifically, the second reactant is selected from NH2-CH2-CH2-NR’2、NH2-CH2-CH2-OR’；R ' represents H or C1-C3Alkane
Base.It is understood that two R ' can be with identical, can also be different.
Preferably, the second reactant is selected from ethylenediamine, monoethanolamine, N- methyl ethylenediamines, N, N- dimethyl-ethylenediamines or 2-
One or more in methoxyethyl amine.
Wherein, inert atmosphere does not produce side reaction with the reactant before reaction and reacted product, does not influence to react
Be smoothed out.It is highly preferred that inert atmosphere is nitrogen atmosphere or argon gas atmosphere.It is, of course, understood that can also be it
Its atmosphere, such as helium atmosphere.
Wherein, heating can use water-bath, oil bath or electric hot plate heating.Stirring can be magnetic agitation or mechanical agitation.
Wherein, the time of reaction is 5min-30min.The length in reaction time can control the substitution amount of R2 groups,
5min-30min can make R2 group substitution amount suitable, further improve the performance of electron transport material.
S2, product separated, obtain electron transport material.Specifically, after reaction finishes, by remaining second reactant
Go divided by separate product, then product is cleaned, then separation of solid and liquid, finally dry.
Wherein it is preferred to remove remaining second reactant by depressurizing rotary evaporation.Ethanol-second can be used in cleaning
The mixed solvents such as acetoacetic ester, methanol-ethyl acetate, ethanol-acetone or methanol-acetone；Solid-liquid separating method can use centrifugation point
From method；Dry is preferably to be dried in vacuo.
The preparation method of the electron transport material of the present invention, it is simple to operation.
Present invention also offers a kind of perovskite solar cell.
Referring to Fig. 1, a kind of perovskite solar cell 100, including calcium titanium ore bed 110, positioned at the side of calcium titanium ore bed 110
Hole transmission layer 121 and first electrode 131, and electron transfer layer 122, Yi Ji positioned at the opposite side of calcium titanium ore bed 110
Two electrodes 132.
Wherein, calcium titanium ore bed 110 is the core component layer of perovskite solar cell 100, and its main function is to absorb light
Hole and electronics and can be produced.
Preferably, the perovskite material in calcium titanium ore bed 110 is selected from the compound representated by following chemical formula：MAxFA1- xPbI3-aBra、MAxFA1-xPbI3-bClb、MAxFA1-xPbBr3-cClc, wherein, x values 0~1, the equal value 0~3 of a, b, c；Wherein
MA chemical structural formula is CH3NH3 +, FA chemical structural formula is CH (NH2)2 +.It is, of course, understood that the calcium of the present invention
Titanium ore material does not limit to above-claimed cpd, can also be that those skilled in the art think suitable other perovskite materials.
Preferably, the thickness of calcium titanium ore bed 110 is 300nm~1000nm.It so can further improve the perovskite sun
The performance of energy battery 100.
Wherein, hole transmission layer 121 is located at the side (upside in Fig. 1) of calcium titanium ore bed 110, and its main function is to be
Hole caused by calcium titanium ore bed 110 is separated and transmits export.
Hole transmission layer 121 can be organic hole transport material layer, can also be inorganic hole transporter layer.Specifically
Ground, when hole transmission layer 121 is organic hole transport material layer, hole transmission layer 121 be preferably Spiro-OMeTAD layers,
PEDOT:PSS layer, P3HT layers, PTAA layers or PCDTBT layers.Wherein, Spiro-OMeTAD represents 2,2', 7,7'- tetra- [N, N- bis-
(4- methoxyphenyls) amino] two fluorenes of -9,9'- spiral shells.When hole transmission layer 121 is inorganic hole transporter layer, hole passes
Defeated layer 121 is preferably nickel oxide layer, CuI layers or the CuSCN layers of non-stoichiometric.
Preferably, the thickness of hole transmission layer 121 is 300nm~600nm.It so can both ensure quality of forming film, reduce
The defects of hole transmission layer 121；It may insure that the series resistance of inside is relatively low again, be advantageous to short circuit current raising.
Wherein, electron transfer layer 122 is located at the side (downside in Fig. 1) of calcium titanium ore bed 110, and its main function is to be
It will be electrically separated caused by calcium titanium ore bed 110 and transmit export.
Preferably, the thickness of electron transfer layer 122 is 10nm~50nm.It so can both ensure quality of forming film, reduce and lack
Fall into；It may insure that the series resistance of inside is relatively low again, be advantageous to short circuit current raising.
Electron transfer layer 122 of the present invention, on the one hand, the halogens in calcium titanium ore bed 110 can be solidified, so both can be with
The defects of reducing calcium titanium ore bed 110 state, the stability of calcium titanium ore bed 110 can also be improved；On the other hand, can preferably obstruct
Hole, prevent the photohole of calcium titanium ore bed 110 and electronics in electron transfer layer 122 occur it is compound.
Preferably, electron transfer layer is to form coating liquid by the coating of spin-coating method, spraying process or knife coating.More preferably
Ground, the solvent of coating liquid is chlorobenzene, o-dichlorohenzene, or both mixing；The concentration of electron transport material in coating liquid is preferred
For 10-40mg/ml.
Wherein, the main function of first electrode 131 is to collect hole and be connected with external circuit.Second electrode 132 it is main
Effect is to collect electronics and be connected with external circuit.
The perovskite solar cell 100 of the present invention can be forward structure or inverted structure.
When perovskite solar cell 100 is forward structure, first electrode 131 is metal electrode；Second electrode 132 is
Electrically conducting transparent substrate.It is highly preferred that when perovskite solar cell 100 is forward structure, hole transmission layer 121 is from organic
Hole transport material.
When perovskite solar cell 100 is inverted structure, first electrode 131 is electrically conducting transparent substrate；Second electrode
132 be metal electrode.It is highly preferred that when perovskite solar cell 100 is inverted structure, hole transmission layer 121 selects nothing
Machine hole transport material.
Wherein, electrically conducting transparent substrate provides support for other each layers of perovskite solar cell 100.Electrically conducting transparent substrate
Side is perovskite solar cell 100 to light side.
Specifically, electrically conducting transparent substrate includes transparent base layer and the transparent conductive film being attached on transparent base layer
Layer.The thickness of transparent conductive film layer is preferably 300nm~500nm.It so can further improve perovskite solar cell
Performance.Transparent conductive film layer is preferably ITO layer, FTO layers, ZTO layer, AZO layers, IWO layers etc..
The thickness of transparent base layer is preferably 1.1mm~2.5mm.Enough mechanically supported power so can be both ensured, again
Absorption of the transparent base layer to light can be reduced, so that more light enter in calcium titanium ore bed 110, so as to increase the absorption of light profit
With.
Transparent conductive film layer can be formed on transparent base layer by physical vaporous deposition, evaporation or sputtering.
Specifically, electrically conducting transparent substrate is preferably transparent conducting glass or electrically conducting transparent plastics.That is, formed transparent
Transparent base layer in basalis is glassy layer or plastic layer.Such as FTO electro-conductive glass, FTO conductive plastics, ITO electro-conductive glass,
ITO conductive plastics.When electrically conducting transparent substrate is ITO electro-conductive glass or ITO conductive plastics, the thickness of ITO layer is preferably 300nm
~400nm.When electrically conducting transparent substrate is FTO electro-conductive glass or FTO conductive plastics, the thickness of FTO layers is 500nm.
Wherein, metal electrode side is the backlight side of perovskite solar cell 100.
Preferably, metal electrode is silver electrode, aluminium electrode or gold electrode.
Preferably, the thickness of metal electrode is 100nm~200nm.
Preferably, metal electrode is formed using vacuum evaporation or vacuum sputtering.
In the present invention, calcium titanium ore bed 110, hole transmission layer 121 can be chemical spray layer, spin-coated layer, scraping coating etc..
The perovskite solar cell of the present invention, due to including electric transmission material provided by the present invention in electron transfer layer
Material；So electron transfer layer also has the dual-use function to calcium titanium ore bed passivation, consolidating for halogens in calcium titanium ore bed can be strengthened
Change acts on, the defects of so can both having reduced calcium titanium ore bed state, the stability of calcium titanium ore bed can also be improved；Electric transmission simultaneously
Layer can also preferably obstruct hole, and it is compound to prevent that the electronics in the photohole and electron transfer layer of calcium titanium ore bed from occurring, changes
The kind contact with calcium titanium ore bed, be advantageous to improve photoelectric transformation efficiency.
Below in conjunction with specific embodiment, the present invention is further illustrated.
Embodiment 1
In a nitrogen atmosphere, take 0.1g PC60BM to be put into 100mL monoethanolamine, then stirred under the conditions of 80 DEG C of oil bath
React 0.5h.After reaction finishes, remaining monoethanolamine is removed using decompression rotary evaporation, solid residue will be obtained with mixed
Bonding solvent (ethanol：Ethyl acetate=1:2) clean, be then centrifuged for separating, 12h is dried in vacuo at last 60 DEG C.
Obtained electron transport material, is denoted as A1.
Embodiment 2
In a nitrogen atmosphere, 0.1g IC are weighed60BA is put into 100mL monoethanolamine, is then stirred under the conditions of 80 DEG C of water-bath
React 0.5h.After reaction finishes, remaining monoethanolamine is removed using decompression rotary evaporation, solid residue will be obtained with mixed
Bonding solvent (ethanol：Ethyl acetate=1:2) clean, be then centrifuged for separating, 12h is dried in vacuo at last 60 DEG C.
Obtained electron transport material, is denoted as A2.
Embodiment 3
Electron transport material A1 is added in chlorobenzene, is configured to the chlorobenzene solution that concentration is 20mg/mL.
Under 2000rpm rotating speed, by the FTO electro-conductive glass substrates of above-mentioned chlorobenzene solution spin coating after cleaning, as
Electron transfer layer；Then in the MAPbI of spin coating 1.5M thereon3Solution, rotating speed 2500rpm, and 0.5h is heated at 100 DEG C,
Form fine and close calcium titanium ore bed；Hole is formed on calcium titanium ore bed with 2000rpm rotating speed spin coating spiro-OMeTAD solution again
Transport layer；Last evaporation thickness is 100nm Ag films as back electrode.
Each technical characteristic of embodiment described above can be combined arbitrarily, to make description succinct, not to above-mentioned reality
Apply all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, the scope that this specification is recorded all is considered to be.
Embodiment described above only expresses the several embodiments of the present invention, and its description is more specific and detailed, but simultaneously
Can not therefore it be construed as limiting the scope of the patent.It should be pointed out that come for one of ordinary skill in the art
Say, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the protection of the present invention
Scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (10)
1. a kind of electron transport material, it is characterised in that the electron transport material includes the compound of below formula：
Wherein, ring F represents fullerene；
R1 represents following substituent：
N1 is selected from 1~2；
R2 represents following substituent：
-NH-CH2-CH2-NR’2、-NH-CH2-CH2-O R’；R ' represents H or C1-C3Alkyl；
N2 is selected from 1~4.
2. electron transport material according to claim 1, it is characterised in that the electron transport material is below formula
Compound：
3. a kind of preparation method of electron transport material, it is characterised in that comprise the following steps：
Under an inert atmosphere, the first reactant is mixed with the second reactant and in 60 DEG C~85 DEG C heating responses；Then will production
Thing separates, and obtains electron transport material；
First reactant is selected from the compound of below formula：
Wherein, ring F represents fullerene；
R1 represents following substituent：
N1 is selected from 1~2；
Second reactant is selected from NH2-CH2-CH2-NR’2、NH2-CH2-CH2-OR’；R ' represents H or C1-C3Alkyl.
4. the preparation method of electron transport material according to claim 3, it is characterised in that second reactant is selected from second two
One or more in amine, monoethanolamine, N- methyl ethylenediamines, N, N- dimethyl-ethylenediamines or 2- methoxyethyl amines.
5. the preparation method of electron transport material according to claim 3, it is characterised in that the time of the reaction be 5min~
30min。
6. the preparation method of electron transport material according to claim 3, it is characterised in that the temperature of the reaction be 60 DEG C~
85℃。
7. the preparation method of electron transport material according to claim 3, it is characterised in that the inert atmosphere is nitrogen atmosphere
Or argon gas atmosphere.
8. a kind of perovskite solar cell, it is characterised in that including electron transfer layer, the electron transfer layer will comprising right
Seek the electron transport material described in 1~2 any one.
9. perovskite solar cell according to claim 8, it is characterised in that the thickness of the electron transfer layer is
20nm~100nm.
10. perovskite solar cell according to claim 8, it is characterised in that the perovskite solar cell is
Inverted structure.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113809240A (en) * | 2021-09-08 | 2021-12-17 | 中山大学 | Method for passivating perovskite thin film layer and application of method in solar cell |
| CN114409549A (en) * | 2022-01-25 | 2022-04-29 | 华能新能源股份有限公司 | Fullerene derivative material, preparation method thereof and perovskite solar cell |
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|---|---|---|---|---|
| CN103242172A (en) * | 2013-05-08 | 2013-08-14 | 中国科学院化学研究所 | Amino modified fullerene derivative, and preparation method and application thereof |
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