CN117924366B - Acridone compound, and preparation method and application thereof - Google Patents

Acridone compound, and preparation method and application thereof Download PDF

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CN117924366B
CN117924366B CN202410332375.1A CN202410332375A CN117924366B CN 117924366 B CN117924366 B CN 117924366B CN 202410332375 A CN202410332375 A CN 202410332375A CN 117924366 B CN117924366 B CN 117924366B
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compound
layer
acridone
electrode
hole transport
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CN117924366A (en
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李明昊
莫易
应昕彤
杨玉雯
曾海鹏
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Trina Solar Co Ltd
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Abstract

The invention relates to an acridone compound, a preparation method and application thereof. The structural general formula of the carbazole compound is shown as formula (I): (I) ; wherein R 1 and R 2 are each independently halogen, alkyl, alkoxy or amino; r 3 is alkylene; n1 and n2 are each independently any integer from 0 to 4. The acridone compound has excellent hole transmission performance, good stability and good wettability, has self-assembly characteristic, is suitable for being used as a hole transmission material, and improves the open-circuit voltage, short-circuit current, filling factor, photoelectric conversion efficiency and thermal stability of a photoelectric device.

Description

Acridone compound, and preparation method and application thereof
Technical Field
The invention relates to the field of organic functional materials, in particular to an acridone compound, a preparation method and application thereof.
Background
Thin film Photovoltaic (PV) technology has received attention over the last decades for its advantages of light weight, translucency, low cost, and versatile applications. Among emerging materials, organic-inorganic metal halide Perovskite (PSCs) has unique properties of low exciton binding energy, bipolar and long Cheng Zailiu sub-transport, and ease of solution handling, making it an ideal candidate for the preparation of high performance solar cells with Power Conversion Efficiencies (PCE) approaching 26.1%.
In PSCs, the hole transport material has the functions of optimizing interface, adjusting energy level matching and the like. Conventional Hole Transport Materials (HTM) are based on [2- (3, 6-dimethoxy-9H-carbazol-9-yl) ethyl ] phosphonic acid (MeO-2 PACz), poly [ bis (4-phenyl) (2, 4, 6-trimethylphenyl) amine ] (PTAA), and the hole mobility of such HTM is generally low, and the problem of high cost also prevents further development of the HTM at PSCs.
Currently, a variety of novel self-assembled monolayer materials (SAM) have been demonstrated to be capable of constructing efficient hole transport layers for PSCs, such as benzene, biphenyl, triindene, etc., but these materials have a charge neutral group as the core, which reduces hole mobility to some extent. In view of the foregoing, there is a need in the industry for a novel hole transport material that has excellent hole transport properties, excellent wettability, and good stability.
Disclosure of Invention
Based on the above, the invention provides an acridone compound, a preparation method and application thereof, wherein the acridone compound is a novel organic functional material with self-assembly property, excellent hole transmission property, good solubility, excellent wettability and good stability, is suitable for being used as a hole transmission material, and improves the open-circuit voltage, short-circuit current, filling factor, photoelectric conversion efficiency and thermal stability of a photoelectric device.
The technical proposal is as follows:
In a first aspect of the present invention, there is provided an acridone compound having a structural general formula shown in formula (I):
（I）；
Wherein R 1 and R 2 are each independently halogen, alkyl, alkoxy or amino;
R 3 is alkylene;
n1 and n2 are each independently any integer from 0 to 4.
In some embodiments, the structural general formula of the acridone compound is shown in formula (II):
（II）。
In some embodiments, R 1 is selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, or amino.
In some embodiments, R 2 is selected from halogen, C1-C20 alkyl, C1-C20 alkoxy, or amino.
In some embodiments, each of said R 3 is independently selected from C1-C20 alkylene.
In some embodiments, the acridone compound has a structure as shown in any one of the following:
、/>、/>、、/>、/>、、/>。
in a second aspect of the present invention, there is provided a method for preparing an acridone compound as described above, comprising the steps of:
Mixing and reacting the compound 1 with ethylene glycol to prepare a compound 2;
Compound 2 and dihaloalkane X 1-R3-X2 are mixed and reacted to prepare compound 3;
Mixing and reacting the compound 3 with triethyl phosphite to prepare a compound 4;
hydrolyzing the compound 4 to prepare the acridone compound;
The reaction equation is expressed as follows:
Wherein X 1 and X 2 are each independently halogen, and R 1、R2 and R 3 are as defined above.
A third aspect of the present invention provides a hole transport material comprising an acridone compound as described above, or an acridone compound prepared according to the method described above.
A fourth aspect of the present invention provides an optoelectronic device comprising functional layers arranged in a stack, at least one of the functional layers comprising a material comprising an acridone compound as described above, or an acridone compound prepared according to a method as described above, or a hole transporting material as described above.
A fifth aspect of the present invention provides a light emitting diode comprising a first electrode, a second electrode, one or more functional layers located between the first electrode and the second electrode, at least one of the functional layers comprising a material comprising an acridone compound as described above, or an acridone compound prepared according to a method as described above, or a hole transporting material as described above.
A sixth aspect of the present invention provides a perovskite solar cell comprising an electrode layer, a first functional layer, a perovskite light absorbing layer, a second functional layer, and a conductive glass layer, which are stacked;
one of the first functional layer and the second functional layer is a hole transport layer, and the other is an electron transport layer, wherein the material of the hole transport layer comprises an acridone compound as described above, or an acridone compound prepared according to the method described above, or a hole transport material as described above.
In some of these embodiments, the material of the electrode layer is selected from at least one of silver, copper, conductive oxide, and carbon electrode.
In some embodiments, the electron transport layer is formed from a material selected from at least one of methyl [6,6] -phenyl-C61-butyrate, C60, and tin oxide.
In some embodiments, the perovskite light absorbing layer has a structural general formula ABX 3, wherein a is selected from one or more of Cs+、MA+(CH3NH3 +)、FA+(CH(NH2)2 +) and Rb +, B is selected from one or more of Pb 2+、Sn2+ and Mn 2+, and X is a halide ion.
In some embodiments, the material of the conductive glass layer is selected from at least one of indium tin oxide, zinc aluminum oxide, indium aluminum oxide, cerium indium oxide, and tungsten indium oxide.
In some of these embodiments, a hole blocking layer is further laminated between the electron transport layer and the electrode layer.
In some embodiments, the hole blocking layer is made of at least one material selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline and zirconium acetylacetonate.
The invention has at least the following beneficial effects:
The acridone compound provided by the invention comprises an acridone mother nucleus, substituent groups R 1 and R 2 connected to the mother nucleus, an anchoring group phosphoric acid and R 3 connected with the anchoring group and the acridone. The acridone is used as a mother nucleus, so that an electric field built in the device is optimized, interface recombination is inhibited, an energy level structure is optimized, and the capability of extracting perovskite holes is improved. And the terminal position uses a phosphoric acid group, and by utilizing the coordination synergistic physical and chemical effects of phosphoric acid and a metal oxide substrate (such as ITO), a layer of hole-transporting small molecular interface can be effectively formed on the metal oxide substrate, meanwhile, the defects on the metal oxide can be passivated, the interface stability is enhanced, and the stability of the photoelectric device under the working condition is improved. By matching with a multifunctional regulation and control means utilizing substituent groups, dioxolane is constructed on a core group, so that the interaction between perovskite and a hole transport material is increased, the molecular solubility is optimized, and the preparation of a large-area perovskite component is facilitated. In addition, the synthesis route of the acridone compound provided by the invention is simple and convenient, and the material cost is low, thereby being beneficial to amplification and industrial production.
According to tests, compared with the traditional hole transport materials, in some examples of the invention, the acridone compound is used in photoelectric devices, such as perovskite solar cells, so that the open circuit voltage of the perovskite solar cells can be improved by more than 9.70%, and some embodiments can be improved by more than 13.6%; the short-circuit current is increased by more than 1.43%, and the short-circuit current can be increased by more than 6.04% in some embodiments; the filling factor is improved by more than 4.99 percent, and the filling factor can be improved by more than 7.64 percent in some embodiments; the photoelectric conversion efficiency is improved by 19.60%, and the photoelectric conversion efficiency can be improved by 27.18% in some embodiments; the thermal stability is improved by more than 20 percent.
Drawings
FIG. 1 is a schematic diagram of a perovskite solar cell according to an embodiment of the invention;
FIG. 2 is a schematic diagram of a perovskite solar cell according to an embodiment of the invention;
FIG. 3 is a J-V curve of perovskite solar cell as per example 1 and comparative example 1 for device according to the invention;
Fig. 4 is a graph showing the thermal stability of perovskite solar cell produced according to example 1 and comparative example 1 of the device of the invention.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The present invention may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
Where the terms "comprising," "having," and "including" are used herein, it is intended to cover a non-exclusive inclusion, another element may be added, unless a specifically defined term is used, such as "consisting of … …," etc.
In the present disclosure, the terms "first," "second," and "second" are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implying a number of technical features being indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include at least one such feature.
In describing positional relationships, when an element such as a layer, film or substrate is referred to as being "on" another film layer, it can be directly on the other film layer or intervening film layers may also be present, unless otherwise indicated. Further, when a layer is referred to as being "under" another layer, it can be directly under, or one or more intervening layers may also be present. It will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present.
The words "preferably," "more preferably," "more preferably," and the like, refer to embodiments of the invention that may provide certain benefits in some instances. However, other embodiments may be preferred under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention. That is, in the present invention, "preferable", "more preferable", etc. are merely description of embodiments or examples that are more effective, but do not limit the scope of the present invention. In the present invention, "further", "still further", "particularly" and the like are used for descriptive purposes to indicate differences in content but should not be construed as limiting the scope of the invention.
In the present invention, "at least one" means one or more, such as one, two or more. The meaning of "plural" or "several" means at least two, for example, two, three, etc., and the meaning of "multiple" means at least two, for example, two, three, etc., unless specifically defined otherwise. In the description of the present invention, the meaning of "several" means at least one, such as one, two, etc., unless specifically defined otherwise.
When a range of values is disclosed in the present invention, the range is considered to be continuous and includes the minimum and maximum values of the range, as well as each value between such minimum and maximum values. Further, when a range refers to an integer, each integer between the minimum and maximum values of the range is included. Further, when multiple range description features or characteristics are provided, the ranges may be combined. In other words, unless otherwise indicated, all ranges disclosed herein are to be understood to include any and all subranges subsumed therein. And only a few numerical ranges are specifically disclosed herein. However, any lower limit may be combined with any upper limit to form a range not explicitly recited; and any lower limit may be combined with any other lower limit to form a range not explicitly recited, and any upper limit may be combined with any other upper limit to form a range not explicitly recited. Furthermore, each separately disclosed point or individual value may itself be combined as a lower limit or upper limit with any other point or individual value or with other lower limit or upper limit to form a range not explicitly recited.
All steps of the present invention may be performed sequentially or randomly unless otherwise specified. For example, the method comprises steps (a) and (b), meaning that the method may comprise steps (a) and (b) performed sequentially, or may comprise steps (b) and (a) performed sequentially. For example, the method may further comprise step (c), meaning that step (c) may be added to the method in any order, e.g., the method may comprise steps (a), (b) and (c), steps (a), (c) and (b), steps (c), (a) and (b), etc.
Unless mentioned to the contrary, singular terms may include plural and are not to be construed as being one in number.
The temperature parameter in the present invention is not particularly limited, and may be a constant temperature treatment or a treatment within a predetermined temperature range. The constant temperature process allows the temperature to fluctuate within the accuracy of the instrument control.
The weights of the relevant components mentioned in the embodiments of the present invention may refer not only to the specific contents of the respective components but also to the proportional relationship between the weights of the respective components, and thus, it is within the scope of the disclosure of the embodiments of the present invention as long as the contents of the relevant components are scaled up or down according to the embodiments of the present invention. Specifically, the weight described in the examples of the present invention may be mass units known in the chemical industry such as mu g, mg, g, kg.
In the present invention, referring to a unit of a data range, if a unit is only carried behind a right end point, the units indicating the left and right end points are the same. For example, 800-850 nm indicates that the units of the left end point "800" and the right end point "850" are nm (nanometers).
In the present invention, "above" or "below" includes the present number, such as 1 or below, indicating 1 or less (1 or less), 1 or above, indicating 1 or more (1 or more).
In the present invention, "a and B are independently selected from x, y or z" means that a and B are independent events, and event a does not affect occurrence of event B, so that B may be selected from any one of x, y or z when a is selected from x, B may be selected from any one of x, y or z when a is selected from y, and B may be selected from any one of x, y or z when a is selected from z.
In the present invention, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The phrase containing the term, for example, "C1-C9 alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which may be, independently of each other, C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantane, and the like.
In the present invention, the term "alkylene" means that the alkyl group loses one more hydrogen atom and may represent a linear, branched and/or cyclic alkylene group. The alkylene group may have a carbon number of 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The phrase containing the term, for example, "C1-C9 alkylene" refers to an alkylene group containing 1 to 9 carbon atoms, which may be, independently of each other, C1 alkylene, C2 alkylene, C3 alkylene, C4 alkylene, C5 alkylene, C6 alkylene, C7 alkylene, C8 alkylene, or C9 alkylene. Non-limiting examples of alkylene groups include methylene, ethylene, n-propylene, n-butylene, and the like.
In the present invention, the term "alkoxy" refers to a group having an "-O-alkyl" group, i.e. an alkyl group as defined above is attached to the alkyl structure via an oxygen atom. The C1-C20 alkoxy group comprises a C1-C19, a C1-C14, a C1-C12, a C2-C6, a C2-C4, a C15, a C10, a C8, a C5, a C20 alkoxy group and the like. Phrases containing the C1-C20 alkoxy term, suitable examples include, but are not limited to: methoxy (-O-CH 3 or-OMe), ethoxy (-O-CH 2CH3 or-OEt), and t-butoxy (-O-C (CH 3)3 or-OtBu).
In the present invention, the term "halogen" means the elements of the seventh main group of the periodic table of elements, including fluorine, chlorine, bromine, iodine, and astatine.
In the present invention, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.gR 2 in (3) is connected with any substitutable site of benzene ring,/>R 2 of (A) is connected with any substitutable site of naphthalene ring.
Hole Transport Materials (HTM) play a vital role in perovskite solar cells, and take on the functions of hole extraction, transport, electron blocking, etc. at the perovskite/HTM interface. At present, a self-assembled monolayer hole transport material based on carbazole derivatives, a synthesis method and application thereof are reported, wherein carbazole derivatives are used as a mother nucleus, butyl phosphoric acid is used as an anchoring group, and due to the influence of pi structures, the hole transport performance of carbazole phosphonic acid derivatives is lower. If the hole transport performance is to be improved, additional groups are required to be introduced, the preparation cost of the device is increased, and uneven interface distribution and larger interface defects are caused by multiple kinds of molecular nucleation. Or reports a scheme of regulating and controlling the molecular structure of carbazole dye by using carbazole as a parent nucleus and enhancing the molecular planeness of carbazole dye by molecular engineering, although the carbazole dye adopts various functional groups (alkyl, alkoxy, phenyl and thiophene) as chemical anchoring groups, the overlap of pi orbitals between adjacent molecules is increased, and the migration capability of delocalized pi electrons is enhanced. However, in order to enhance the flatness and hole transport property of the molecules, polycyclic aromatic hydrocarbon is introduced, which results in the disadvantages of difficult synthesis of materials, high cost and difficult subsequent optimization of materials.
In order to solve the problems, the invention provides an acridone compound, a preparation method and application thereof, wherein the acridone compound is a novel organic functional material with self-assembly property, excellent hole transmission property, good solubility, excellent wettability and good stability, is suitable for being used as a hole transmission material, and improves the open-circuit voltage, short-circuit current, filling factor, photoelectric conversion efficiency and thermal stability of a photoelectric device.
The technical proposal is as follows:
an acridone compound has a structural general formula shown in a formula (I):
（I）；
Wherein R 1 and R 2 are each independently halogen, alkyl, alkoxy or amino;
R 3 is alkylene;
n1 and n2 are each independently any integer from 0 to 4.
In some embodiments, the structural general formula of the acridone compound is shown in formula (II):
（II）。
It is understood that in the present invention r is any integer from 0 to 4, i.e. r is 0,1, 2,3 or 4.
It is understood that in the present invention, R 1 is halogen, alkyl, alkoxy, or amino (-NH 2). Further, R 1 is selected from halogen, C1-C20 alkyl, C1-C20 alkoxy or amino. Still further, the R 1 is selected from fluorine, chlorine, bromine, iodine, C1-C20 straight chain alkyl, C3-C20 branched chain alkyl, C3-C20 cyclic alkyl, C1-C20 straight chain alkoxy, C3-C20 branched chain alkoxy, C3-C20 cyclic alkoxy, or amino. Without limitation, the R 1 is selected from fluorine, chlorine, bromine, iodine, C1-C10 straight chain alkyl, C3-C10 branched chain alkyl, C1-C10 straight chain alkoxy, C3-C20 branched chain alkoxy, or amino.
It is understood that in the present invention n1 is any integer from 0 to 4, i.e. n1 is 0, 1, 2, 3 or 4.
It is understood that in the present invention, R 2 is halogen, alkyl, alkoxy, or amino. Further, R 1 is selected from halogen, C1-C20 alkyl, C1-C20 alkoxy or amino. Still further, the R 2 is selected from fluorine, chlorine, bromine, iodine, C1-C20 straight chain alkyl, C3-C20 branched chain alkyl, C3-C20 cyclic alkyl, C1-C20 straight chain alkoxy, C3-C20 branched chain alkoxy, C3-C20 cyclic alkoxy, or amino. Without limitation, the R 2 is selected from fluorine, chlorine, bromine, iodine, C1-C10 straight chain alkyl, C3-C10 branched chain alkyl, C1-C10 straight chain alkoxy, C3-C20 branched chain alkoxy, or amino.
It will be appreciated that in the present invention n2 is any integer from 0 to 4, i.e. n2 is 0, 1, 2, 3 or 4.
It is understood that in the present invention, R 3 are each independently alkylene. Further, each of said R 3 is independently selected from C1-C20 alkylene. Still further, each of said R 3 is independently selected from the group consisting of C1-C6 alkylene, and each of said R 3 is independently selected from the group consisting of methylene, ethylene, propylene, butylene, pentylene, and hexylene, without limitation.
Without limitation, the acridone compounds of the present invention have any of the following structures:
、/>、/>、、/>、/>、、/>。
the invention also provides a preparation method of the acridone compound, which comprises the following steps:
Mixing and reacting the compound 1 with ethylene glycol to prepare a compound 2;
Compound 2 and dihaloalkane X 1-R3-X2 are mixed and reacted to prepare compound 3;
Mixing and reacting the compound 3 with triethyl phosphite to prepare a compound 4;
hydrolyzing the compound 4 to prepare the acridone compound;
The reaction equation is expressed as follows:
Wherein X 1 and X 2 are each independently halogen, and R 1、R2 and R 3 are as defined above.
In some embodiments, the X 1 is selected from fluorine, chlorine, bromine, or iodine.
In some embodiments, the X 2 is selected from fluorine, chlorine, bromine, or iodine.
The invention also provides a hole transport material comprising an acridone compound as described above, or an acridone compound prepared according to the method described above. The hole transport material has excellent hole transport property, good solubility, excellent wettability and good stability, is used for a functional layer of a photoelectric device, and can improve the open-circuit voltage, short-circuit current, filling factor, photoelectric conversion efficiency and thermal stability of the photoelectric device.
The invention also provides a photoelectric device, which comprises a laminated functional layer, wherein at least one layer of functional layer is made of acridone compounds as described above, or acridone compounds prepared according to the method as described above, or hole transport materials as described above, not only can passivate a metal oxide substrate, but also has excellent hole transport capacity, and is beneficial to improving the photoelectric conversion efficiency, short circuit current, filling factor, open circuit voltage and thermal stability of the photoelectric device.
The invention also provides a light-emitting diode, which comprises a first electrode, a second electrode and one or more functional layers arranged between the first electrode and the second electrode, wherein the material of at least one functional layer is selected from acridone compounds as described above, acridone compounds prepared according to the method, or hole transport materials as described above, not only can passivate a metal oxide substrate, but also has excellent hole transport capability, and is beneficial to improving the photoelectric conversion efficiency, short-circuit current, filling factor, open-circuit voltage and thermal stability of the light-emitting diode.
The perovskite solar cell comprises an electrode layer, a first functional layer, a perovskite light absorption layer, a second functional layer and a conductive glass layer which are stacked;
the first functional layer and the second functional layer are respectively a hole transport layer and an electron transport layer, wherein the material of the hole transport layer comprises the acridone compound, the acridone compound prepared according to the method, or the hole transport material.
In some of these embodiments, the material of the electrode layer is selected from at least one of silver, copper, conductive oxide, and carbon electrode.
In some embodiments, the electron transport layer is formed from a material selected from at least one of methyl [6,6] -phenyl-C61-butyrate, C60, and tin oxide.
In some embodiments, the perovskite light absorbing layer has a structural general formula ABX 3, wherein a is selected from one or more of Cs+、MA+(CH3NH3 +)、FA+(CH(NH2)2 +) and Rb +, B is selected from one or more of Pb 2+、Sn2+ and Mn 2+, and X is a halide ion. Further, A is Cs +, B is Pb 2+, and X is a halogen ion. Further, X is at least one of fluoride, chloride, bromide, and iodide.
In some of these embodiments, the material of the conductive glass layer is selected from at least one of indium tin oxide, zinc aluminum oxide, indium aluminum oxide, cerium indium oxide, and tungsten indium oxide.
In the present invention, the thickness of the electrode layer is 5nm to 200nm, the thickness of the electron transport layer is 5nm to 200nm, the thickness of the perovskite light absorption layer is 0.01 μm to 2 μm, the thickness of the hole transport layer is 5nm to 200nm, and the thickness of the conductive glass layer is 5nm to 200nm, without limitation.
In some of these embodiments, a hole blocking layer is further laminated between the electron transport layer and the electrode layer. Without limitation, the hole blocking layer is made of at least one material selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline and zirconium acetylacetonate. The hole blocking layer has a thickness of 5nm to 200nm, without limitation.
In some of these embodiments, referring to fig. 1, the photovoltaic device is a perovskite solar cell 1 comprising an electrode layer 110, an electron transport layer 120, a perovskite light absorbing layer 130, a hole transport layer 140, and a conductive glass layer 150, which are stacked;
The material of the hole transport layer 140 is selected from acridone compounds as described above, or hole transport materials as described above.
In some of these embodiments, referring to fig. 2, a hole blocking layer 160 is further laminated between the electron transport layer 120 and the electrode layer 110.
The invention also provides a preparation method of the perovskite solar cell, which comprises the following steps:
Providing a substrate;
preparing an organic hole transport material solution, and coating the organic hole transport material solution on a substrate to prepare a hole transport layer;
Preparing a perovskite precursor solution, and coating the perovskite precursor solution on the hole transport layer to prepare a perovskite light absorption layer;
Preparing an electron transport material solution, and coating the electron transport material solution on the perovskite light absorption layer to prepare an electron transport layer;
Preparing a hole blocking layer solution, and coating the hole blocking layer solution on an electron transport layer to prepare a hole blocking layer;
An electrode layer was prepared on the hole blocking layer (vapor deposition method).
In some of these embodiments, the organic hole transport material solution is formulated specifically as follows: dissolving the organic hole transport material in chlorobenzene, stirring and dissolving to obtain the organic hole transport material, wherein the mass-volume ratio of the organic hole transport material to the chlorobenzene is 2mg: (1-3) mL.
The invention will be described in connection with the following examples, but it is not limited thereto, and it is to be understood that the appended claims summarize the scope of the invention and that certain changes made to the various embodiments of the invention which are contemplated by one skilled in the art are to be covered by the spirit and scope of the appended claims.
1. Compound synthesis examples
Synthesis example 1: synthesis of P1
The synthetic route is as follows:
2, 7-dibromoacridone (1236 mg, 3.50 mmol, 1-1), paratoluenesulfonic acid hydrate (50 mg,0.26 mmol), ethylene glycol (2.00 mL,32.2 mmol) were added to a 100mL round bottom flask, which was connected to a condenser via a Dean-Stark apparatus, under nitrogen atmosphere. The nitrogen was replaced by vacuum, the temperature was raised to 100℃after three cycles, and then anhydrous toluene (40 mL) was added dropwise to the reaction system and stirred for 48 hours. Then, carrying out vacuum filtration, washing with methanol and drying under high vacuum to obtain white solid product compounds 1-2;
To a 100 mL round bottom flask was added compound 1-2 (1080 mg, 2.72 mmol) and tetrabutylammonium bromide (0.32 g, 0.27 mmol) in sequence in 1, 4-dibromobutane (15 mL) under nitrogen atmosphere, then 50% aqueous KOH solution (5 mL) was added dropwise, and the mixture was heated to 65 ℃ and stirred overnight. After stopping the reaction, adding water to quench the reaction, extracting the obtained reaction liquid with CH 2Cl2, drying and concentrating, removing excessive dibromobutane under reduced pressure, and purifying by column chromatography. The ratio of petroleum ether to dichloromethane of the eluent is equal to 10:1, and white solid product compounds 1-3 are obtained.
Under the nitrogen atmosphere, adding the compounds 1-3 (1272 mg,2.39 mmol) and triethyl phosphite (10 mL) into a 100 mL reaction tube, heating to 160 ℃ and stirring for 15 hours, and removing unreacted triethyl phosphite by oil pump rotary evaporation (70 ℃) after the reaction is finished to obtain light yellow mucus compounds 1-4 which are directly used for the next reaction.
The pale yellow mucus 1-4 was dissolved in 1, 4-dioxane (10 mL) under nitrogen atmosphere, then trimethylbromosilane (3.66 g,23.90 mmol) was added dropwise, stirred overnight at room temperature, and then the organic solvent was removed by rotary evaporation. Adding 10 mL methanol, dropwise adding deionized water until white solid is precipitated in the methanol solution, continuing stirring at room temperature for 6 hours, filtering to obtain white solid, dissolving the white solid in a small amount of tetrahydrofuran, reprecipitating in acetone, filtering and drying to obtain the target product hole transport material P1 which is the white solid.
1H NMR (500 MHz, Chloroform-d) δ 7.95 (s, 2H), 7.49 (d, J = 2.0 Hz, 2H), 7.45 (dd, J = 8.3, 2.1 Hz, 2H), 6.99 (d, J = 8.2 Hz, 2H), 4.09 (s, 4H), 3.82 (t, J = 5.3 Hz, 2H), 2.00 – 1.90 (m, 2H), 1.83 – 1.75 (m, 2H), 1.75 – 1.64 (m, 2H).
HRMS (ESI/Q-TOF, m/z): Calcd for [M+H]+ C19H21O5Br2NP+: 531.9446, found: 531.9421.
As can be seen from the combination of nmr hydrogen spectrum data and mass spectrum data, the present example successfully synthesizes the target compound.
Synthesis example 2: synthesis of P2
The synthetic route is as follows:
2, 7-dimethoxy acridone (894 mg, 3.50 mmol, 2-1), p-toluene sulfonic acid hydrate (50 mg,0.26 mmol), ethylene glycol (2.00 mL,32.2 mmol) were added under nitrogen to a 100mL round bottom flask connected to a condenser by a Dean-Stark apparatus. The nitrogen was replaced by vacuum, the temperature was raised to 100℃after three cycles, and then anhydrous toluene (40 mL) was added dropwise to the reaction system and stirred for 48 hours. Then, after filtration under vacuum, washing with methanol and drying under high vacuum, the product compound 2-2 was obtained as a white solid.
Compound 2-2 (814 mg, 2.72 mmol) and tetrabutylammonium bromide (0.32 g, 0.27 mmol) were added sequentially to a 100mL round bottom flask under nitrogen atmosphere, dissolved in 1, 4-dibromobutane (15 mL), followed by dropwise addition of 50% aqueous KOH (5 mL), and stirred at 65 ℃ for overnight. After stopping the reaction, adding water to quench the reaction, extracting the obtained reaction liquid with CH 2Cl2, drying and concentrating, removing excessive dibromobutane under reduced pressure, and purifying by column chromatography. The ratio of petroleum ether to dichloromethane of the eluent is equal to 10:1, and the white solid product compound 2-3 is obtained.
Under the nitrogen atmosphere, adding the compound 2-3 (1038 mg,2.39 mmol) and triethyl phosphite (10 mL) into a 100 mL reaction tube, heating to 160 ℃ and stirring for 15 hours, and removing unreacted triethyl phosphite by oil pump rotary evaporation (70 ℃) after the reaction is finished to obtain a light yellow mucus compound 2-4 which is directly used for the next reaction.
The pale yellow mucus 2-4 was dissolved in 1, 4-dioxane (10 mL) under nitrogen atmosphere, then trimethylbromosilane (3.66 g,23.90 mmol) was added dropwise, stirred overnight at room temperature, and then the organic solvent was removed by rotary evaporation. Adding 10 mL methanol, dropwise adding deionized water until white solid is precipitated in the methanol solution, continuing stirring at room temperature for 6 hours, filtering to obtain white solid, dissolving the white solid in a small amount of tetrahydrofuran, reprecipitating in acetone, filtering and drying to obtain the target product hole transport material P2 which is the white solid.
1H NMR (500 MHz, Chloroform-d) δ 7.95 (s, 2H), 7.07 – 6.98 (m, 3H), 6.88 (dd, J = 8.2, 2.1 Hz, 2H), 4.09 (s, 4H), 3.82 (t, J = 5.4 Hz, 2H), 3.82 (s, 7H), 2.00 – 1.90 (m, 2H), 1.83 – 1.75 (m, 2H), 1.75 – 1.64 (m, 2H).
HRMS (ESI/Q-TOF, m/z): Calcd for [M+H]+ C21H27O7NP+: 436.1447, found: 436.1418.
As can be seen from the combination of nmr hydrogen spectrum data and mass spectrum data, the present example successfully synthesizes the target compound.
Synthesis example 3: synthesis of P3
The synthetic route is as follows:
2-Aminoacridone (736 mg, 3.50 mmol, 3-1), paratoluenesulfonic acid hydrate (50 mg,0.26 mmol), ethylene glycol (2.00 mL,32.2 mmol) were added under nitrogen to a 100 mL round bottom flask connected to a condenser by a Dean-Stark apparatus. The nitrogen was replaced by vacuum, the temperature was raised to 100℃after three cycles, and then anhydrous toluene (40 mL) was added dropwise to the reaction system and stirred for 48 hours. Then, after filtration under vacuum, washing with methanol and drying under high vacuum, the product compound 3-2 was obtained as a white solid.
Compound 3-2 (692 mg, 2.72 mmol) and tetrabutylammonium bromide (0.32 g, 0.27 mmol) were added sequentially to a 100mL round bottom flask under nitrogen atmosphere, dissolved in 1, 4-dibromobutane (15 mL), followed by dropwise addition of 50% aqueous KOH (5 mL), and stirred at 65 ℃ for overnight. After stopping the reaction, adding water to quench the reaction, extracting the obtained reaction liquid with CH 2Cl2, drying and concentrating, removing excessive dibromobutane under reduced pressure, and purifying by column chromatography. The ratio of petroleum ether to dichloromethane of the eluent is equal to 10:1, and the white solid product compound 3-3 is obtained.
In a 100 mL reaction tube under nitrogen atmosphere, compound 3-3 (930 mg,2.39 mmol) and triethyl phosphite (10 mL) were added, the temperature was raised to 160 ℃ and stirred for 15 hours, after the reaction was completed, unreacted triethyl phosphite was removed by oil pump rotary evaporation (70 ℃) to obtain pale yellow mucus compound 3-4, which was directly used in the next reaction.
The pale yellow mucus 3-4 was dissolved in 1, 4-dioxane (10 mL) under nitrogen atmosphere, then trimethylbromosilane (3.66 g,23.90 mmol) was added dropwise, stirred overnight at room temperature, and then the organic solvent was removed by rotary evaporation. Adding 10 mL methanol, dropwise adding deionized water until white solid is precipitated in the methanol solution, continuing stirring at room temperature for 6 hours, filtering to obtain white solid, dissolving the white solid in a small amount of tetrahydrofuran, reprecipitating in acetone, filtering and drying to obtain the target product hole transport material P3 which is the white solid.
1H NMR (500 MHz, Chloroform-d) δ 7.95 (s, 2H), 7.35 – 7.29 (m, 2H), 7.26 (td, J = 7.5, 1.5 Hz, 1H), 6.99 (dd, J = 6.3, 1.4 Hz, 1H), 6.96 (d, J = 8.1 Hz, 1H), 6.77 (d, J = 2.2 Hz, 1H), 6.65 (dd, J = 8.1, 2.2 Hz, 1H), 4.98 (d, J = 5.5 Hz, 1H), 4.93 (d, J = 5.5 Hz, 1H), 4.15 – 4.02 (m, 4H), 3.82 (t, J = 5.3 Hz, 2H), 2.00 – 1.90 (m, 2H), 1.83 – 1.75 (m, 2H), 1.75 – 1.64 (m, 2H).
HRMS (ESI/Q-TOF, m/z): Calcd for [M+H]+ C19H24O5N2P+: 391.1345, found: 391.1329.
As can be seen from the combination of nmr hydrogen spectrum data and mass spectrum data, the present example successfully synthesizes the target compound.
Synthesis example 4: synthesis of P4
The synthetic route is as follows:
2, 7-dimethyl-9 (10H) -acridone (782 mg, 3.50 mmol, 4-1), paratoluenesulfonic acid hydrate (50 mg,0.26 mmol), ethylene glycol (2.00 mL,32.2 mmol) were added under nitrogen to a 100 mL round bottom flask connected to a condenser by a Dean-Stark apparatus. The nitrogen was replaced by vacuum, the temperature was raised to 100℃after three cycles, and then anhydrous toluene (40 mL) was added dropwise to the reaction system and stirred for 48 hours. Then, after filtration under vacuum, washing with methanol and drying under high vacuum, the product compound 4-2 was obtained as a white solid.
Compound 4-2 (727 mg, 2.72 mmol) and tetrabutylammonium bromide (0.32 g, 0.27 mmol) were added sequentially to a 100mL round bottom flask under nitrogen atmosphere, dissolved in 1, 4-dibromobutane (15 mL), followed by dropwise addition of 50% aqueous KOH (5 mL), and stirred at 65 ℃ for overnight. After stopping the reaction, adding water to quench the reaction, extracting the obtained reaction liquid with CH 2Cl2, drying and concentrating, removing excessive dibromobutane under reduced pressure, and purifying by column chromatography. The ratio of petroleum ether to dichloromethane of the eluent is equal to 10:1, and the white solid product compound 4-3 is obtained.
In a 100 mL reaction tube under nitrogen atmosphere, compound 4-3 (962 mg,2.39 mmol) and triethyl phosphite (10 mL) were added, the temperature was raised to 160℃and stirred for 15 hours, after the reaction was completed, unreacted triethyl phosphite was removed by rotary evaporation with an oil pump (70 ℃) to give pale yellow mucus compound 4-4, which was directly used in the next reaction.
The pale yellow mucus 4-4 was dissolved in 1, 4-dioxane (10 mL) under nitrogen atmosphere, then trimethylbromosilane (3.66 g,23.90 mmol) was added dropwise, stirred overnight at room temperature, and then the organic solvent was removed by rotary evaporation. Adding 10 mL methanol, dropwise adding deionized water until white solid is precipitated in the methanol solution, continuing stirring at room temperature for 6 hours, filtering to obtain white solid, dissolving the white solid in a small amount of tetrahydrofuran, reprecipitating in acetone, filtering and drying to obtain the target product hole transport material P4 which is the white solid.
1H NMR (500 MHz, Chloroform-d) δ 7.95 (s, 2H), 7.16 – 7.07 (m, 5H), 6.98 (dd, J = 8.0, 3.6 Hz, 2H), 4.09 (s, 4H), 3.82 (t, J = 5.4 Hz, 2H), 2.29 (s, 5H), 2.00 – 1.90 (m, 2H), 1.83 – 1.75 (m, 2H), 1.75 – 1.64 (m, 2H).
HRMS (ESI/Q-TOF, m/z): Calcd for [M+H]+ C21H27O5NP+: 404.1549, found: 404.1513.
As can be seen from the combination of nmr hydrogen spectrum data and mass spectrum data, the present example successfully synthesizes the target compound.
2. Device embodiment
Device example 1:
embodiment 1 of the present device provides a perovskite solar cell shown in fig. 2 and a preparation method thereof, including the following steps:
(1) Ultrasonically cleaning ITO conductive glass with glass cleaning liquid, deionized water and ethanol respectively for 20min, and finally drying in a drying oven at 75 ℃ for later use; placing the dried ITO glass substrate into an ultraviolet ozone machine for treatment of 20min, removing organic impurities on the surface of the ITO glass substrate, and optimizing the surface wettability of the ITO glass substrate;
(2) 1mg of hole transport material P1 is dissolved in 2mL chlorobenzene, and stirred at normal temperature until the hole transport material P1 is completely dissolved, so as to obtain an organic hole transport material solution; dripping 60 mu L of organic hole transport material solution on the treated ITO glass, spin-coating 30 s at a rotation speed of 5000 rpm, and heating and annealing the TCO glass in the step (1) at 100 ℃ on a hot table for 10 min to form a hole transport layer with a thickness of 10 nm;
(3) Lead 722.08 mg iodide and 238.50 mg methyl iodide are dissolved in N, N-Dimethylformamide (DMF) of 1mL, and stirred at normal temperature until the lead 722.08 mg iodide and the 238.50 mg methyl iodide are completely dissolved, so as to obtain perovskite precursor solution; in a nitrogen glove box, 60 mu L of perovskite precursor solution is dripped on ITO conductive glass forming a hole transmission layer, spin coating is carried out for 30s at a rotation speed of 5000 rpm, 150 mu L of chlorobenzene is dripped rapidly in the process of 25 to s, and then the ITO glass is put on a hot table to be heated and annealed at 100 ℃ for 40 to min, so that a perovskite light absorption layer with a thickness of 300nm can be formed;
(4) Dissolving 20 mg methane fullerene phenyl-C61-butyric acid-methyl ester (PCBM) in 1 mL chlorobenzene, stirring at normal temperature to obtain [6,6] -phenyl-C61-butyric acid methyl ester solution; taking 30 mu L of [6,6] -phenyl-C61-methyl butyrate solution and forming an ITO conductive glass with a perovskite light absorption layer, spin-coating 60 s with 3000 rpm to form an electron transport layer with the thickness of 20 nm;
(5) Dissolving 0.5 mg of 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP) in 1mL isopropanol, and stirring at normal temperature to obtain a hole blocking layer solution; dripping 40 mu L of hole blocking layer solution above the electron transport layer, and spin-coating 35 s with 5000 rpm to form a hole blocking layer with a thickness of 6 nm;
(6) Transferring the ITO conductive glass with the hole blocking layer, the electron transport layer, the perovskite layer and the hole transport layer into a vacuum coating instrument, evaporating a silver electrode when the vacuum degree is pumped to 3 x 10 -4 Pa, and forming a silver electrode with the thickness of 100nm, thus obtaining the electrode layer with the thickness of 100 nm.
Device examples 2 to 4 and device comparative example 1 the device structure and fabrication method were substantially the same as those of device example 1, except that the SAM hole transporting material in device example 1 was replaced with the material shown in table 1, and the other conditions were kept unchanged.
Wherein Meo-2PACz has the structural formula of。
The perovskite solar cells of device examples 1 to 4 and device comparative example 1 were subjected to performance testing by the following test methods:
The J-V characteristics of the devices were measured with a computer-controlled Keithley 2400 light source measuring apparatus under AM 1.5G illumination (100 mW/cm 2) of an SS-F5-3A solar simulator (Enli Technology, co., ltd.) without any pretreatment. The light intensity was calibrated by standard silicon solar cells (SRC-00178, calibrated by Enli Technology, co., ltd) prior to testing. Each substrate contained 4 cells with an active area of 0.098 cm 2. During the test, a 0.049 cm 2 reticle was used. The J-V curve of the small area device was measured in reverse scan mode with a scan step size of 0.02V and a dwell time of 1ms for each voltage. The test results are shown in Table 1 below.
TABLE 1
As can be seen from Table 1, compared with the conventional hole transport material Meo-2PACz, the use of the acridone compound shown in the examples of the present invention as a hole transport material in perovskite solar cells can increase the open circuit voltage of the perovskite solar cells by 9.70% or more, and some examples can increase the open circuit voltage by 13.6% or more; the short-circuit current is increased by more than 1.43%, and the short-circuit current can be increased by more than 6.04% in some embodiments; the filling factor is improved by more than 4.99 percent, and the filling factor can be improved by more than 7.64 percent in some embodiments; the photoelectric conversion efficiency is improved by 19.60% or more, and the photoelectric conversion efficiency can be improved by 27.18% or more in some embodiments.
Under the condition of simulated sunlight AM1.5G irradiation with the illumination intensity of 100 mW cm -2, the J-V curves of the battery device using the compound P1 and the reference object Meo-2PACz as hole transport materials are shown in fig. 3, and the EFF can reach 23.49% and 18.47% at most.
The thermal stability curves of the perovskite solar cell device using the compound P1 and the reference Meo-2PACz as the hole transport materials are shown in FIG. 4, and as can be seen from FIG. 4, the PCE of the cell device using Meo-2PACz as the hole transport materials decays by 71% after 200h and 100 ℃ heating aging, and the PCE of the cell device using the compound P1 as the hole transport materials decays by 50% after 200h and 100 ℃ heating aging, which shows that the acridone compound P1 of the invention can be used in the perovskite solar cell to improve the thermal stability.
In summary, the invention provides an acridone compound which is a novel organic functional material with self-assembly property, excellent hole transmission property, good solubility, excellent wettability and good stability, is suitable for being used as a hole transmission material, and improves the open circuit voltage, short circuit current, filling factor, photoelectric conversion efficiency and thermal stability of a photoelectric device.
The technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples merely represent a few embodiments of the present invention and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.

Claims (13)

1. The acridone compound is characterized in that the structural general formula is shown in the formula (I):
（I）；
Wherein R 1 and R 2 are each independently halogen, C1-C20 alkyl, C1-C20 alkoxy or amino;
R 3 is C1-C20 alkylene;
n1 and n2 are each independently any integer from 0 to 4.
2. The acridone compound according to claim 1, wherein the structural general formula is shown in formula (II):
（II）。
3. Acridone according to claim 1 or 2, characterized in that R 1 and R 2 are each independently selected from fluorine, chlorine, bromine, iodine, C1-C10 linear alkyl, C3-C10 branched alkyl, C1-C10 linear alkoxy, C3-C20 branched alkoxy or amino.
4. Acridone according to claim 1 or 2, characterized in that R 3 is selected from C1-C6 alkylene groups.
5. The acridone compound according to claim 1, which has a structure as shown in any one of the following:
、/>、/>、、/>、/>、、/>。
6. A process for the preparation of acridone compounds as claimed in any one of claims 1 to 5, comprising the steps of:
Mixing and reacting the compound 1 with ethylene glycol to prepare a compound 2;
Mixing and reacting the compound 2 with dihaloalkane X 1-R3-X2 to prepare a compound 3;
Mixing and reacting the compound 3 with triethyl phosphite to prepare a compound 4;
Hydrolyzing the compound 4 to prepare the acridone compound of any one of claims 1 to 5;
The reaction equation is expressed as follows:
Wherein each of X 1 and X 2 is independently halogen, and R 1、R2 and R 3 are as defined in any one of claims 1 to 5.
7. A hole transport material comprising the acridone compound according to any one of claims 1 to 5 or prepared by the method of claim 6.
8. An optoelectronic device comprising a stacked arrangement of functional layers, wherein at least one of the functional layers comprises an acridone compound according to any one of claims 1 to 5, an acridone compound prepared by the method of claim 6, or a hole transporting material according to claim 7.
9. A light emitting diode comprising a first electrode, a second electrode, one or more functional layers between the first electrode and the second electrode, at least one of the functional layers comprising the acridone compound of any one of claims 1 to 5, or the acridone compound prepared according to the method of claim 6, or the hole transporting material of claim 7.
10. The perovskite solar cell is characterized by comprising an electrode layer, a first functional layer, a perovskite light absorption layer, a second functional layer and a conductive glass layer which are stacked;
One of the first functional layer and the second functional layer is a hole transport layer, and the other is an electron transport layer, wherein the material of the hole transport layer comprises the acridone compound according to any one of claims 1 to 5, or the acridone compound prepared by the method according to claim 6, or the hole transport material according to claim 7.
11. The perovskite solar cell of claim 10, wherein at least one of the following (1) - (4) is satisfied:
(1) The electrode layer is made of at least one material selected from silver, copper, conductive oxide and carbon electrode;
(2) The material of the electron transport layer is at least one selected from the group consisting of [6,6] -phenyl-C61-methyl butyrate, C60 and tin oxide;
(3) The structural general formula of the perovskite light absorption layer material is ABX 3, wherein A is one or more selected from Cs+、MA+(CH3NH3 +)、FA+(CH(NH2)2 +) and Rb +, B is one or more selected from Pb 2+、Sn2+ and Mn 2+, and X is halogen ion;
(4) The material of the conductive glass layer is at least one selected from indium tin oxide, aluminum zinc oxide, aluminum indium oxide, indium cerium oxide and indium tungsten oxide.
12. The perovskite solar cell according to claim 10 or 11, wherein a hole blocking layer is further provided between the electron transport layer and the electrode layer in a stacked manner.
13. The perovskite solar cell according to claim 12, wherein the material of the hole blocking layer is selected from at least one of 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline and zirconium acetylacetonate.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116178430A (en) * 2023-01-10 2023-05-30 南方科技大学 Acridine-based self-assembled hole selection material and preparation method and application thereof
CN117177595A (en) * 2023-09-05 2023-12-05 天合光能股份有限公司 Photoelectric device, preparation method thereof, photovoltaic module and photovoltaic system

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116178430A (en) * 2023-01-10 2023-05-30 南方科技大学 Acridine-based self-assembled hole selection material and preparation method and application thereof
CN117177595A (en) * 2023-09-05 2023-12-05 天合光能股份有限公司 Photoelectric device, preparation method thereof, photovoltaic module and photovoltaic system

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Inverted perovskite solar cells using dimethylacridine-based dopants;Tan, Qin et al;Nature;20230524;第620卷;545-551 *

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