CN112142957A - High-molecular electron acceptor material and preparation method and application thereof - Google Patents
High-molecular electron acceptor material and preparation method and application thereof Download PDFInfo
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Abstract
The application discloses an organic polymer electron acceptor material and a preparation method and application thereof. The receptor material is characterized in that: (1) the D-A polymer is formed by alternately coupling the electron donor component and the electron acceptor component, so that the band gap of the compound is reduced, and the LUMO energy level of the compound is reduced, thereby being beneficial to the transmission of electrons; (2) different from the traditional D-A macromolecule, the D-A component constructs a conjugated plane of a whole macromolecule main chain vertically and horizontally through intramolecular cyclization reaction, thus greatly improving the molecular planarity and being beneficial to the transmission of electrons in the macromolecule and among chains; (3) nitrogen atoms are introduced into a main chain of the polymer, lone-pair electrons of the nitrogen atoms participate in conjugation, so that the whole band gap of the polymer can be further reduced, the absorption of the polymer reaches a near infrared region, and the absorption of a receptor material is widened, so that the photocurrent is increased. The receptor material is easy to form a film, is convenient to prepare, can improve the photo-thermal and morphological stability of a device, and can be widely applied to the field of organic solar cells.
Description
Technical Field
The application relates to the field of organic solar cells, in particular to an organic solar cell electron acceptor material and a preparation method and application thereof.
Background
The problem of energy and sustainable development is a hot topic that needs all mankind to face, and the traditional fossil energy has limited storage amount and generates a large amount of pollutants in the using process. Among known clean energy sources, solar energy has the characteristic of inexhaustibility, and has almost no pollution to the environment as a clean energy source. Compared with inorganic solar cells, organic solar cells have attracted interest and attention in the field of scientific research because of a series of advantages.
The organic solar cell materials are mainly divided into electron donor materials and electron acceptor materials, and with the progress of research, more and more excellent small molecule acceptor materials are developed, while few successful cases of high molecule acceptor materials exist. Compared with small molecule receptor materials, the high molecule receptor material has better film forming performance, stronger intermolecular action and more outstanding photo-thermal stability. Therefore, the development of new organic polymer materials with high performance has become a new focus.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present application aims to provide an organic polymer electron acceptor material, and a preparation method and application thereof, and aims to solve the problems of low photo-thermal stability and easy change of film morphology of the existing small molecule electron acceptor material.
The technical scheme of the application is as follows:
provides an organic polymer electron acceptor material, wherein the molecular structural formula is as follows:
formula I
Formula II
Wherein R is1，R2Is C1-C20The alkyl chain of (b) may be a straight chain or a branched chain.
Ar is an electron-donating group, forms a condensed ring structure with a mother nucleus, enhances the intramolecular charge transfer effect and molecular planarity, and can be any one of the following groups (the dotted line is the connecting position of the groups):
wherein R is3，R4Is any one of hydrogen atom, alkyl chain, alkoxy chain, alkenyl, alkynyl, aryl or ester group.
EG is a dye molecule group, has strong light absorption and electron absorption capacity, can improve the light absorption performance of the molecules, and can be any one of the following groups (the dotted line is the connecting position of the groups):
wherein R is5Is any one of hydrogen atom, halogen, alkyl chain, alkoxy chain, alkenyl, alkynyl, aryl or ester group.
The application also provides a preparation method of the organic polymer electron acceptor material, wherein the synthesis of the formula I comprises the following steps:
A. coupling 5, 6-dinitro-4, 7-dibromobenzothiadiazole with a compound 1 under the catalysis of a catalyst to generate a polymer solid 2;
B. reacting the polymer 2 with a reducing reagent to close the ring to obtain a fused ring product 3;
C. polymer 3 with halogenated hydrocarbon R under alkaline conditions1And X is coupled by carbon and nitrogen to obtain the polymer shown in the formula I.
The invention also provides a preparation method of the organic polymer electron acceptor material, wherein the synthesis of the formula II comprises the following steps:
a. coupling N-alkyl-5, 6-dinitro-4, 7-dibromobenzazepine triazole and the compound 4 under the catalysis of a catalyst to generate a polymer solid 5;
b. reacting the polymer 5 with a reducing reagent to close a ring to obtain a fused ring product 6;
c. polymer 6 with halogenated hydrocarbon R under alkaline conditions1X is coupled by carbon and nitrogen to obtain the polymer shown in the formula II.
In the present application, all reactions of steps (a) to (C) and steps (a) to (C) need to be carried out under the protection of an inert gas, which is any one of argon, helium or nitrogen, preferably nitrogen;
preferably, the reaction temperature of the reaction in step (A) and step (a) is 90-120 ℃;
preferably, the reaction time of the reaction in step (A) and step (a) is 12-48 h;
preferably, the solvent in step (a) and step (a) is any one of benzene, toluene and N, N-dimethylformamide, preferably toluene;
preferably, the catalyst in step (A) and step (a) is PdCl2(dppf)、Pd(Ph3)2Cl2And Pd (PPh)3)4Is preferably Pd (PPh)3)4The used molar ratio is 0.1-5%;
preferably, the reaction molar ratio of the 5, 6-dinitro-4, 7-dibromobenzothiadiazole to the compound 1 in the step (A) is 1: 1;
preferably, the reaction molar ratio of the N-alkyl-5, 6-dinitro-4, 7-dibromobenzotriazole and the compound 4 in step (a) is 1: 1;
preferably, the molar proportion of the blocking agent in step (A) and step (a) is 0.1-10%;
preferably, the reaction temperature of the reaction in step (B) and step (B) is 150-;
preferably, the reaction time of the reaction in step (B) and step (B) is 12-48 h;
preferably, the solvent in step (B) and step (B) is any one of toluene, chlorobenzene, o-dichlorobenzene and N, N-dimethylformamide, preferably o-dichlorobenzene;
preferably, the reducing agent in the step (B) and the step (B) is any one of triethyl phosphite or triphenylphosphine, preferably triethyl phosphite, and the preferable reaction molar ratio of the polymer 2 or the polymer 5 to the triethyl phosphite is 1:5-1: 50;
preferably, the reaction temperature of the reaction in step (C) and step (C) is 60-120 ℃;
preferably, the reaction time of the reaction in step (C) and step (C) is 12-48 h;
preferably, the solvent in step (C) and step (C) is any one of benzene, toluene and N, N-dimethylformamide, preferably N, N-dimethylformamide;
preferably, the base in step (C) and step (C) is any one of sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide, preferably potassium hydroxide, and the preferred reaction molar ratio of polymer 3 or polymer 6 to potassium hydroxide is 1:4 to 1: 50;
preferably, the polymer 3 or the polymer 6 and the haloalkane R in step (C) and step (C)1The reaction molar ratio of Br is 1:4-1: 50.
The application also provides a solar cell device, which comprises the organic polymer electron acceptor material.
The application also provides an application of the organic polymer electron acceptor material, wherein the organic polymer electron acceptor material is applied to an organic solar cell device.
Has the advantages that: according to the application, the D-A polymer is formed by alternately coupling the electron donor component and the electron acceptor component (1), so that the band gap of the compound is reduced, and the LUMO energy level of the compound is reduced, so that the electron transmission is facilitated. (2) Different from the traditional D-A macromolecule, the D-A component constructs a conjugated plane of a whole macromolecule main chain vertically and horizontally through intramolecular cyclization reaction, thereby greatly improving the molecular planarity and being beneficial to the transmission of electrons in the macromolecule and among chains. (3) Nitrogen atoms are introduced into a main chain of the polymer, lone-pair electrons of the nitrogen atoms participate in conjugation, so that the whole band gap of the polymer can be further reduced, the absorption of the polymer reaches a near infrared region, and the absorption of a receptor material is widened, so that the photocurrent is increased. Meanwhile, the polymer receptor material is easy to form a film, the preparation difficulty of the device is reduced, the photo-thermal stability and the morphology stability of the device can be improved, and the polymer receptor material can be widely applied to the field of organic solar cells.
Detailed Description
The present application provides an organic polymer electron acceptor material, a method for preparing the same, and applications thereof, and the following further detailed description is provided in order to make the objects, technical schemes, and effects of the present application clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
[ example 1 ]
For the polymer receptor P1, the structural formula is
Wherein E is1The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. under the protection of nitrogen, 5, 6-dinitro-4, 7-dibromobenzene is addedDiazosulfide (3.84g, 10mmol), 2, 5-bistrimethylstannothiophene (4.66g, 10mmol), Pd (PPh)3)4(50mg) was added to 20mL of toluene, heated to 110 ℃ and refluxed overnight, and then capped with an end-capping reagent using E1Boronic acid esters of radicals E1B (0.23g, 0.5mmol) and bromide E1-Br (0.20g, 0.5mmol), formula shown below; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid A1;
B. adding polymer A1 and triethyl phosphite (100mmol) into o-dichlorobenzene (50mL) under the protection of nitrogen, and heating at 180 ℃ overnight; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid B1;
C. polymer B1, alkyl bromide (14.4g,40mmol)
Potassium hydroxide (2.24g,40mmol) was added to 50ml of N, N-dimethylformamide and heated at 80 ℃ overnight; and cooling the reaction to room temperature, performing Soxhlet extraction by respectively adopting methanol, n-hexane and chloroform, pouring the chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P1.
[ example 2 ]
For the polymer receptor P2, the structural formula is
Wherein E is2The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. under the protection of nitrogen, 5, 6-dinitro-4, 7-dibromo benzothiadiazole (3.84g, 10mmol), 2, 5-bistrimethylstannothiophene (4.66g, 10mmol), Pd (PPh)3)4(50mg) was added to 20mL of toluene, heated to 110 ℃ and refluxed overnight, and then capped with an end-capping reagent using E1Boronic acid esters of radicals E2B (0.21g, 0.5mmol) and bromide E2-Br (0.18g, 0.5mmol), formula shown below; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid A2;
B. adding polymer A2 and triethyl phosphite (100mmol) into o-dichlorobenzene (50mL) under the protection of nitrogen, and heating at 180 ℃ overnight; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid B2;
C. polymer B2, alkyl bromide (14.4g,40mmol)
Potassium hydroxide (2.24g,40mmol) was added to 50ml of N, N-dimethylformamide and heated at 80 ℃ overnight; and cooling the reaction to room temperature, performing Soxhlet extraction by respectively adopting methanol, n-hexane and chloroform, pouring the chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P2.
[ example 3 ]
For the polymer receptor P3, the structural formula is
Wherein E is1The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. under the protection of nitrogen, N-2-ethylhexyl-5, 6-dinitro-4, 7-dibromobenzazepine triazole (4.79g, 10mmol), 2, 5-bistrimethylstannothiophene (4.66g, 10mmol) and Pd (PPh)3)4(50mg) was added to 20mL of toluene, heated to 110 ℃ and refluxed overnight, and then capped with an end-capping reagent using E1Boronic acid esters of radicals E1B (0.23g, 0.5mmol) and bromide E1-Br (0.20g, 0.5mmol), formula shown below; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid A3;
B. adding polymer A3 and triethyl phosphite (100mmol) into o-dichlorobenzene (50mL) under the protection of nitrogen, and heating at 180 ℃ overnight; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid B3;
C. polymer B3, bromoisooctane (7.72g,40mmol) and potassium hydroxide (2.24g,40mmol) were added to 50ml of N, N-dimethylformamide under nitrogen protection and heated at 80 ℃ overnight; and cooling the reaction to room temperature, performing Soxhlet extraction by respectively adopting methanol, n-hexane and chloroform, pouring the chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P3.
[ example 4 ]
For the polymer receptor P4, the structural formula is
Wherein E is1The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. under the protection of nitrogen, N-2-ethylhexyl-5, 6-dinitro-4, 7-dibromobenzazepine triazole (4.79g, 10mmol), 2, 5-bistrimethylstannyl-4, 8-bis (2-ethyl-1-hexyloxy) benzodithiophene (7.72g, 10mmol), Pd (PPh)3)4(50mg) was added to 20mL of toluene, heated to 110 ℃ and refluxed overnight, and then capped with an end-capping reagent using E1Boronic acid esters of radicals E1B (0.23g, 0.5mmol) and bromide E1-Br (0.20g, 0.5mmol), formula shown below; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid A4;
B. adding polymer A4 and triethyl phosphite (100mmol) into o-dichlorobenzene (50mL) under the protection of nitrogen, and heating at 180 ℃ overnight; after the reaction is cooled to room temperature, respectively adopting methanol, n-hexane and chloroform to carry out Soxhlet extraction, pouring the chloroform extraction part into methanol to precipitate, filtering and drying to obtain a polymer solid B4;
C. polymer B4, bromoisooctane (7.72g,40mmol) and potassium hydroxide (2.24g,40mmol) were added to 50ml of N, N-dimethylformamide under nitrogen protection and heated at 80 ℃ overnight; and cooling the reaction to room temperature, performing Soxhlet extraction by respectively adopting methanol, n-hexane and chloroform, pouring the chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P4.
In summary, the present application reduces the band gap of the compound and lowers the LUMO level of the compound to facilitate electron transport by (1) utilizing the alternating coupling of an electron donor component and an electron acceptor component to form a D-a polymer. (2) Different from the traditional D-A macromolecule, the D-A component constructs a conjugated plane of a whole macromolecule main chain vertically and horizontally through intramolecular cyclization reaction, thereby greatly improving the molecular planarity and being beneficial to the transmission of electrons in the macromolecule and among chains. (3) Nitrogen atoms are introduced into a main chain of the polymer, lone-pair electrons of the nitrogen atoms participate in conjugation, so that the whole band gap of the polymer can be further reduced, the absorption of the polymer reaches a near infrared region, and the absorption of a receptor material is widened, so that the photocurrent is increased. Meanwhile, the polymer receptor material is easy to form a film, the preparation difficulty of the device is reduced, the photo-thermal stability and the morphology stability of the device can be improved, and the polymer receptor material can be widely applied to the field of organic solar cells.
It should be understood that the application of the present application is not limited to the above examples, and that modifications or changes may be made by those skilled in the art based on the above description, and all such modifications and changes are intended to fall within the scope of the appended claims.
Claims (7)
1. An organic polymer electron acceptor material, characterized in that, the molecular structural formula is as follows:
wherein R is1，R2Is C1-C20The alkyl chain of (a) is a straight chain or a branched chain.
2. The organic polymeric electron acceptor material according to claim 1, wherein Ar is any one of the following groups:
wherein R is3，R4Is any one of hydrogen atom, alkyl chain, alkoxy chain, alkenyl, alkynyl, aryl or ester group.
3. The organic polymer electron acceptor material according to claim 1, wherein EG is any one of the following groups:
wherein R is5Is any one of hydrogen atom, halogen, alkyl chain, alkoxy chain, alkenyl, alkynyl, aryl or ester group.
4. A preparation method of an organic polymer electron acceptor material is characterized by comprising the following steps:
the method specifically comprises the following steps:
A. coupling 5, 6-dinitro-4, 7-dibromobenzothiadiazole with a compound 1 under the catalysis of a catalyst to generate a polymer solid 2;
B. reacting the polymer 2 with a reducing reagent to close the ring to obtain a fused ring product 3;
C. polymer 3 with halogenated hydrocarbon R under alkaline conditions1And X is coupled by carbon and nitrogen to obtain the polymer shown in the formula I.
5. A preparation method of an organic polymer electron acceptor material is characterized by comprising the following steps:
the method specifically comprises the following steps:
a. coupling N-alkyl-5, 6-dinitro-4, 7-dibromobenzazepine triazole and the compound 4 under the catalysis of a catalyst to generate a polymer solid 5;
b. reacting the polymer 5 with a reducing reagent to close a ring to obtain a fused ring product 6;
c. polymer 6 with halogenated hydrocarbon R under alkaline conditions1X is coupled by carbon and nitrogen to obtain the polymer shown in the formula II.
6. An organic solar cell device comprising the organic polymeric electron acceptor material as claimed in claims 1-3 or the organic polymeric electron acceptor material prepared as claimed in claims 4-5.
7. Use of an organic polymeric electron acceptor material according to claims 1-3 or prepared according to claims 4-5 in a solar cell device.
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| CN113174032B (en) * | 2021-04-07 | 2023-11-07 | 香港科技大学深圳研究院 | Fluoro condensed ring benzothiadiazole polymer acceptor material and preparation method thereof |
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| CN108948042A (en) * | 2018-09-10 | 2018-12-07 | 中南大学 | Seven yuan of condensed ring class benzotriazole receptors of one kind and its preparation method and application |
| CN109134513A (en) * | 2018-09-10 | 2019-01-04 | 中南大学 | A kind of non-fullerene acceptor material of condensed ring diazosulfide base and its preparation method and application |
| CN109804481A (en) * | 2016-10-05 | 2019-05-24 | 默克专利有限公司 | Organic photodetector |
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| CN109804481A (en) * | 2016-10-05 | 2019-05-24 | 默克专利有限公司 | Organic photodetector |
| CN108948042A (en) * | 2018-09-10 | 2018-12-07 | 中南大学 | Seven yuan of condensed ring class benzotriazole receptors of one kind and its preparation method and application |
| CN109134513A (en) * | 2018-09-10 | 2019-01-04 | 中南大学 | A kind of non-fullerene acceptor material of condensed ring diazosulfide base and its preparation method and application |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113174032B (en) * | 2021-04-07 | 2023-11-07 | 香港科技大学深圳研究院 | Fluoro condensed ring benzothiadiazole polymer acceptor material and preparation method thereof |
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