CN115611892A - Micromolecule electron transport layer material and preparation method and application thereof - Google Patents
Micromolecule electron transport layer material and preparation method and application thereof Download PDFInfo
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- CN115611892A CN115611892A CN202110786094.XA CN202110786094A CN115611892A CN 115611892 A CN115611892 A CN 115611892A CN 202110786094 A CN202110786094 A CN 202110786094A CN 115611892 A CN115611892 A CN 115611892A
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- 239000000463 material Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 32
- 239000013067 intermediate product Substances 0.000 claims description 16
- 229910052763 palladium Inorganic materials 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 12
- 150000003384 small molecules Chemical class 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical class C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=C2C(=O)N(CCN(C)C)C(=O)C1=C32 HPJFXFRNEJHDFR-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 229960001701 chloroform Drugs 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- KZDTZHQLABJVLE-UHFFFAOYSA-N 1,8-diiodooctane Chemical compound ICCCCCCCCI KZDTZHQLABJVLE-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- 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
-
- 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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Abstract
The invention provides a micromolecule electron transport layer material and a preparation method and application thereof. The micromolecule electron transport layer material has a structural general formula shown as a formula I, wherein X is any unit in a formula II. The micromolecule electron transport layer material provided by the invention has the characteristics of easily available raw materials and mild preparation conditions, and is mainly applied to organic solar cells. In a PM6/BTP-eC9 organic solar cell system, the electron transport layer VI provided by the invention is selected, so that the photoelectric conversion efficiency of 18.4 percent is obtained.
Description
Technical Field
The invention belongs to the technical field of semiconductor materials, and particularly relates to a micromolecule electron transport layer material, and a preparation method and application thereof.
Background
In the field of organic solar cells, solution processable small molecules or polymers are often selected as transport layers in order to improve the energy levels at the interface of the active layer and the electrode, and to enhance the injection and collection of electrons. Compared with polymers, the small molecule type transmission layer has the advantages of simple synthesis, clear structure, easy purification and the like, and is rapidly developed in recent years.
The polymer solar cell has the remarkable characteristics of low cost, light weight, good film forming property, capability of being prepared into a large-area flexible device and the like, shows high research value and considerable application prospect, and draws wide attention in academic and industrial fields. For an organic solar cell, different electron transport layer materials are selected, so that the injection and collection efficiency of electrons is changed, and the photoelectric conversion efficiency of a device is greatly influenced.
Disclosure of Invention
The technical problem to be solved by the invention is to overcome the defects of the prior art and provide a small-molecule electron transport layer material.
The second purpose of the invention is to provide a preparation method of the small molecule electron transport layer material.
The third purpose of the invention is to propose the application of the small molecule electron transport layer material.
The technical scheme for realizing the aim of the invention is as follows:
the invention provides a micromolecule electron transport layer material which has the following structural general formula (shown in a formula I), wherein X can be any unit in a formula II.
The invention further provides a preparation method of the micromolecule electron transport layer material, which comprises the following steps:
(1) Performing coupling reaction on the naphthalene diimide derivative and the thiophene unit in a first organic solvent under the action of a palladium complex to obtain an intermediate product a after the reaction; the substituent of the naphthalene diimide derivative is a halogen atom.
(2) Reacting the intermediate product a with a brominating reagent in a second organic solvent to obtain an intermediate product b after the reaction is finished;
(3) And (3) carrying out coupling reaction on the intermediate product b and the compound shown in the formula III or the derivative thereof in a mixed solvent of a third organic solvent and an alkaline aqueous solution under the catalysis of a palladium complex.
Wherein, the molar ratio of the naphthalene diimide derivative to the thiophene unit in the step (1) is 1.
Wherein, the palladium complex in the step (1) is tetratriphenylphosphine palladium or a mixture of tris (dibenzylideneacetone) dipalladium and tri-o-tolylphosphine; preferably, the molar ratio of the naphthalene diimide derivative to the palladium complex is 5-10;
more preferably, the first organic solvent in step (1) is selected from one or two of toluene and xylene; the coupling reaction temperature is 80-120 ℃; the reaction time is 12-48h.
Wherein, the brominating reagent in the step (2) is N-bromosuccinimide; preferably, the molar ratio of the intermediate product a to the N-bromosuccinimide is 1; preferably, the reaction temperature of the step (2) is 20-40 ℃; the reaction time is 8-24h.
Wherein, the second organic solvent in the step (2) is trichloromethane and acetic acid, and preferably, the volume ratio of the trichloromethane to the acetic acid is 1.
More preferably, the concentration of the intermediate product a in the second organic solvent is 0.1 to 0.5mol/L.
Wherein the molar ratio of the intermediate product b in the step (3) to the compound shown in the formula III or the derivative thereof is 1.
Wherein, the palladium complex in the step (3) is palladium tetratriphenylphosphine or a mixture of tris (dibenzylideneacetone) dipalladium and tri-o-tolylphosphine; preferably, the molar ratio of the intermediate b (the compound X) to the palladium complex in the step (3) is 5-10;
wherein, the third organic solvent in the step (3) is one or two of toluene and xylene; the alkaline aqueous solution is sodium carbonate or potassium carbonate aqueous solution, and the molar ratio of the intermediate product b (the compound X) to the solute in the alkaline aqueous solution is 1.
Preferably, the molar concentration of the potassium carbonate aqueous solution in the step (3) is 1-5mol/L.
Preferably, the reaction temperature of the step (3) is 80-120 ℃, and the reaction time is 12-72h.
Wherein, the derivative of the compound shown in the formula III in the step (3) is prepared by the following method:
adding hydrogen peroxide into a compound shown in a formula III, and heating to react at 60-100 ℃; obtaining a compound shown as a formula IV;
a derivative II (a compound shown in a formula V) is obtained by reacting a compound shown in a formula III with bromoethane in an ethanol solvent; the molar ratio of the compound shown in the formula III to the bromoethane is 1.
The solar cell is prepared by applying the micromolecule electron transport layer material.
Compared with the prior art, the invention has the following beneficial effects:
the micromolecule electron transport layer material provided by the invention has the characteristics of easily available raw materials and mild preparation conditions, and is mainly applied to organic solar cells. In a PM6/BTP-eC9 organic solar cell system, the electron transport layer VI provided by the invention is selected, so that the photoelectric conversion efficiency of 18.4 percent is obtained.
Drawings
Fig. 1 is a current-voltage curve of a photovoltaic device in application example 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The materials in the examples are prepared according to known methods or are directly commercially available, unless otherwise specified.
Example 1
This example provides a novel small molecule electron transport layer, which has the following structure,
the embodiment also provides a preparation method of the small molecule electron transport layer material, which comprises the following steps:
(1) Performing coupling reaction on a naphthalimide derivative shown in a formula VII and a thiophene unit shown in a formula VIII (the molar ratio is 1; after the reaction is finished, the compound shown as the formula IX is obtained. The palladium complex is tetratriphenylphosphine palladium. The molar ratio of the naphthalimide derivative shown in the formula VII to the palladium complex is 8.
(2) Reacting a compound shown as a formula IX with N-bromosuccinimide (the molar ratio is 1.
(3) A compound shown in a formula X and a compound shown in a formula III (the molar ratio is 1: 3) are subjected to a coupling reaction in an aqueous solution of toluene and 2mol/L potassium carbonate under the action of a palladium complex, the temperature is 110 ℃, and the time is 72 hours, so that a compound shown in a formula VI is obtained. The molar ratio of the compound X to the potassium carbonate is 1.
Example 2
This example provides a new small molecule electron transport layer material, which has the following structure,
the first two steps of the preparation in this example were the same as in example 1.
(3) Adding hydrogen peroxide into the compound shown in the formula III, heating and reacting in an ethanol solution, and obtaining the compound shown in the formula IV after the reaction is finished. The molar ratio of the compound III to hydrogen peroxide is 1.
(4) The compound of formula X and the compound of formula IV are subjected to coupling reaction in an organic solvent to obtain the compound of formula XI, and the preparation steps are the same as the step (3) in the example 1.
Example 3
This example provides a novel small molecule electron transport layer, which has the following structure,
the first two steps of the preparation in this example were the same as in example 1.
(3) And (3) reacting the compound shown in the formula III with bromoethane in an ethanol solvent to obtain the compound shown in the formula V after the reaction is finished. The molar ratio of compound iii to bromoethane was 1. The reaction temperature was 25 ℃. The reaction time was 72h.
(4) A compound represented by the formula X and a compound represented by the formula V are subjected to a coupling reaction in an organic solvent to obtain a compound represented by the formula XII, and the preparation procedure is the same as that in the step (3) in example 1.
Application example 1
The electron transport layer according to the invention is used in an organic photovoltaic cell device, preferably a polymer solar cell: the PM6/BTP-eC9 system selects a compound shown as a formula VI as an electron transport layer, and the preparation method of the device is as follows:
and ultrasonically cleaning the transparent conductive glass with the ITO by using deionized water, acetone and isopropanol sequentially for 15 minutes, drying the ITO glass by using a nitrogen gun, placing the dried ITO glass into UVO for treatment for 15 minutes, spin-coating PEDOT (PSS) on the ITO at the rotation speed of 4000 rpm, and drying the ITO glass at the temperature of 150 ℃ for 15 minutes to obtain a modification layer with the thickness of about 25 nm. In a glove box, a chloroform solution of 7mg/ml of PM6 and BTP-eC9 was prepared at a mass ratio of 1.2, 0.3% of 1, 8-Diiodooctane (DIO) was added, the solution was uniformly spin-coated on PEDOT: PSS at 2800 rpm, an electron transport layer (a compound represented by formula VI) prepared with methanol was then spin-coated on the active layer at 3000 rpm, and silver was deposited on the electron transport layer in a vacuum of 1X 10-6 Torr to form an electrode having a thickness of 100 nm.
The combination of a 500W xenon lamp and an AM 1.5 filter is used as a white light source for simulating sunlight, and the light intensity at the measuring position of the device is adjusted to 100mW/cm -2 To makeThe prepared polymer solar cell device was tested for three parameters of open circuit voltage, short circuit current and fill factor using Keithley. The results are shown in fig. 1, where the open-circuit voltage Voc =0.852V, the short-circuit current Jsc =27.6mA/cm2, the fill factor FF =78.3%, and the photoelectric conversion efficiency PCE =18.4%.
The present invention is illustrated by the above embodiments, but the present invention is not limited to the above embodiments, that is, the present invention is not limited to the above embodiments. It will be apparent to those skilled in the art that any modifications to the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific forms, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. The micromolecule electron transport layer material is characterized by having a structural general formula shown as a formula I, wherein X is any unit in a formula II.
2. The method for preparing a small molecule electron transport layer material according to claim 1, comprising the steps of:
(1) Performing coupling reaction on the naphthalene diimide derivative and the thiophene unit in a first organic solvent under the action of a palladium complex to obtain an intermediate product a after the reaction; the substituent of the naphthalene diimide derivative is a halogen atom;
(2) Reacting the intermediate product a with a brominating agent in a second organic solvent to obtain an intermediate product b after the reaction is finished;
(3) And (3) carrying out coupling reaction on the intermediate product b and a compound shown in the formula III or a derivative thereof in a mixed solvent of a third organic solvent and an alkaline aqueous solution under the action of a palladium complex to obtain the micromolecular electron transport layer material.
3. The production method according to claim 2, characterized in that, in the step (1), the molar ratio of the naphthalene diimide derivative to the thiophene unit is 1.
4. The method according to claim 2, wherein in the step (1), the palladium complex is tetrakistriphenylphosphine palladium or a mixture of tris (dibenzylideneacetone) dipalladium and tri-o-tolylphosphine; preferably, the molar ratio of the naphthalene diimide derivative to the palladium complex is 5-10;
more preferably, the coupling reaction temperature in step (1) is 80-120 ℃; the reaction time is 12-48h.
5. The method according to claim 2, wherein in the step (2), the brominating agent is N-bromosuccinimide; preferably, the molar ratio of the intermediate product a to the N-bromosuccinimide is 1; preferably, in the step (2), the reaction temperature is 20-40 ℃; the reaction time is 8-24h.
6. The method according to claim 2, wherein in the step (2), the brominating agent is N-bromosuccinimide; the second organic solvent is trichloromethane and acetic acid; preferably, the volume ratio of trichloromethane to acetic acid is 1;
more preferably, the concentration of the intermediate product a in the second organic solvent is 0.1 to 0.5mol/L.
7. The method according to claim 2, wherein in the step (3), the molar ratio of the intermediate product b to the compound represented by the formula III or the derivative thereof is 1.
8. The preparation method according to claim 2, wherein in the step (3), the basic aqueous solution is sodium carbonate or potassium carbonate aqueous solution, and the molar ratio of the intermediate product b to the solute in the basic aqueous solution is 1;
preferably, the reaction temperature of the step (3) is 80-120 ℃, and the reaction time is 12-72h.
9. The process according to any one of claims 2 to 8, wherein the derivative of the compound of formula III in step (3) is prepared by:
the first derivative is shown as a compound shown as a formula IV, hydrogen peroxide is added into the compound shown as the formula III for heating reaction, and the heating temperature is 60-100 ℃; obtaining a compound shown as a formula IV;
the derivative II is shown as a compound of a formula V, and the compound of the formula III reacts with bromoethane in an ethanol solvent to obtain the compound of the formula V; the molar ratio of the compound shown in the formula III to the bromoethane is 1.
10. A solar cell prepared by applying the small molecule electron transport layer material of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110786094.XA CN115611892B (en) | 2021-07-12 | Small molecule electron transport layer material and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110786094.XA CN115611892B (en) | 2021-07-12 | Small molecule electron transport layer material and preparation method and application thereof |
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| Publication Number | Publication Date |
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| CN115611892A true CN115611892A (en) | 2023-01-17 |
| CN115611892B CN115611892B (en) | 2024-05-10 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190066931A1 (en) * | 2017-08-31 | 2019-02-28 | Boe Technology Group Co., Ltd. | Polymer, method for preparing the same and solar cell comprising the polymer |
| KR20210017454A (en) * | 2019-08-08 | 2021-02-17 | 포항공과대학교 산학협력단 | Composition comprising fluorinated naphthalene diimide derivative compound, organic solar cell comprising same and method of preparing same |
| CN112375079A (en) * | 2020-11-20 | 2021-02-19 | 常州大学 | Micromolecular receptor material based on naphthalene diimide unit derivative, preparation method and application |
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190066931A1 (en) * | 2017-08-31 | 2019-02-28 | Boe Technology Group Co., Ltd. | Polymer, method for preparing the same and solar cell comprising the polymer |
| KR20210017454A (en) * | 2019-08-08 | 2021-02-17 | 포항공과대학교 산학협력단 | Composition comprising fluorinated naphthalene diimide derivative compound, organic solar cell comprising same and method of preparing same |
| CN112375079A (en) * | 2020-11-20 | 2021-02-19 | 常州大学 | Micromolecular receptor material based on naphthalene diimide unit derivative, preparation method and application |
Non-Patent Citations (3)
| Title |
|---|
| CHAO-CHEN LIN等: "Synthesis and characterization of naphthalene diimide (NDI)-based near infrared chromophores with two-photon absorbing properties", 《TETRAHEDRON》, vol. 66, pages 8629 - 8634, XP027415286 * |
| DOLI SRIVANI等: "Small molecular non-fullerene acceptors based on naphthalenediimide and benzoisoquinoline-dione functionalities for efficient bulk-heterojunction devices", 《DYES AND PIGMENTS》, vol. 143, pages 1 - 9 * |
| JING YANG等: "Effects of Inserting Thiophene as a π‑Bridge on the Properties of Naphthalene Diimide-alt-Fused Thiophene Copolymers", 《APPLIED MATERIALS & INTERFACES》, vol. 9, pages 44070 * |
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