CN112142957B - Polymer electron acceptor material and preparation method and application thereof - Google Patents
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Abstract
The application discloses an organic polymer electron acceptor material, and a preparation method and application thereof. The acceptor material is characterized in that: (1) The electron donor component and the electron acceptor component are alternately coupled to form a D-A polymer, so that the band gap of the compound is reduced, the LUMO energy level of the compound is reduced, and the electron transmission is facilitated; (2) Compared with the traditional D-A polymer, in the application, the D-A component constructs a conjugated plane of a main chain of the whole polymer vertically and horizontally through intramolecular cyclization reaction, so that the planeness of the polymer is greatly improved, and the transmission of electrons in the polymer and among chains is facilitated; (3) The nitrogen atoms are introduced into a main chain of the polymer, and lone pair electrons of the nitrogen atoms participate in conjugation, so that the overall band gap of the polymer can be further reduced, the polymer can be absorbed to reach a near infrared region, and the absorption of an acceptor material is widened, so that the photocurrent is increased. The acceptor material is easy to form a film, is convenient to prepare, can improve the photo-thermal and morphological stability of the 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, a preparation method and application thereof.
Background
The problems of energy and sustainable development are hot topics facing all people, and traditional fossil energy reserves are limited and a large amount of pollutants are generated in the using process. Among known clean energy sources, solar energy has the inexhaustible characteristic, and is almost free from pollution to the environment as a clean energy source. Organic solar cells have attracted interest and attention in the scientific field due to a series of advantages over inorganic solar cells.
Organic solar cell materials are mainly divided into electron donor materials and electron acceptor materials, and as people research into the materials, more and more excellent small molecule acceptor materials are developed, and the successful cases of high molecule acceptor materials are rare. Compared with a small molecular receptor material, the high molecular receptor material has better film forming performance, stronger intermolecular action and more outstanding photo-thermal stability. Therefore, development of a novel organic polymer material with high performance has become a new hot spot.
Disclosure of Invention
In view of the defects in the prior art, the application aims to provide an organic high-molecular electron acceptor material, a preparation method and application thereof, and aims to solve the problems that the existing small-molecular electron acceptor material is low in photo-thermal stability and the appearance of a film is easy to change.
The technical scheme of the application is as follows:
an organic polymer electron acceptor material is provided, wherein the molecular structural formula is as follows:
i is a kind of
II (II)
Wherein R is 1 ，R 2 Is C 1 -C 20 The alkyl chain of (2) may be a straight chain or a cross chain.
Ar is an electron donating group, forms a condensed ring structure with a mother nucleus, enhances 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 is 3 ，R 4 Is any one of a hydrogen atom, an alkyl chain, an alkoxy chain, an alkenyl group, an alkynyl group, an aryl group or an ester group.
EG is a dye molecule group, has strong light absorption and electron absorption capability, can improve the light absorption performance of molecules, and can be any one of the following groups (the dotted line is the connection position of the group):
wherein R is 5 Is any one of a hydrogen atom, a halogen, an alkyl chain, an alkoxy chain, an alkenyl group, an alkynyl group, an aryl group or an 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-binitro-4, 7-dibromobenzothiadiazole and a compound 1 under the catalysis of a catalyst to generate a polymer solid 2;
B. the polymer 2 reacts with a reducing reagent to close the ring to obtain a condensed ring product 3;
C. polymer 3 with halogenated hydrocarbon R under alkaline conditions 1 X is coupled through 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-binitro-4, 7-dibromobenzonitrogen triazole and a compound 4 under the catalysis of a catalyst to generate polymer solid 5;
b. the polymer 5 reacts with a reducing reagent to close the ring to obtain a condensed ring product 6;
c. polymer 6 is reacted with a halogenated hydrocarbon R under alkaline conditions 1 X is coupled through carbon and nitrogen to obtain the polymer shown in the formula II.
In the present application, all the 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 reactions in step (a) and step (a) is from 90 to 120 ℃;
preferably, the reaction time of the reactions in step (a) and step (a) is from 12 to 48 hours;
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 PdCl 2 (dppf)、Pd(Ph 3 ) 2 Cl 2 And Pd (PPh) 3 ) 4 Any of them is preferably Pd (PPh) 3 ) 4 The molar ratio of the used is 0.1-5%;
preferably, the reaction molar ratio of 5, 6-dinitro-4, 7-dibromobenzothiadiazole to compound 1 in step (A) is 1:1;
preferably, the molar ratio of the N-alkyl-5, 6-dinitro-4, 7-dibromobenzotriazol to the compound 4 in step (a) is 1:1;
preferably, the molar ratio of the end-capping agent in step (a) and step (a) is from 0.1 to 10%;
preferably, the reaction temperature of the reactions in step (B) and step (B) is 150-200 ℃;
preferably, the reaction time of the reactions in step (B) and step (B) is from 12 to 48 hours;
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 step (B) and step (B) is any one of triethyl phosphite or triphenylphosphine, preferably triethyl phosphite, and the preferred molar ratio of polymer 2 or polymer 5 to triethyl phosphite is 1:5-1:50;
preferably, the reaction temperature of the reactions in step (C) and step (C) is 60-120 ℃;
preferably, the reaction time of the reactions in step (C) and step (C) is from 12 to 48 hours;
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 molar ratio of polymer 3 or polymer 6 to potassium hydroxide is from 1:4 to 1:50;
preferably, in step (C) and step (C) said polymer 3 or polymer 6 and haloalkane R 1 The molar ratio of Br reaction is 1:4-1:50.
The application also provides a solar cell device comprising 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.
The beneficial effects are that: the electron donor component and the electron acceptor component are alternately coupled to form the D-A polymer, so that the band gap of the compound is reduced, and the LUMO energy level of the compound is reduced, thereby being beneficial to electron transmission. (2) Unlike traditional D-A polymer, the D-A component forms a conjugated plane of the whole polymer main chain through intramolecular cyclization reaction, greatly improves the planarity of the polymer and is beneficial to the transmission of electrons in the polymer and among chains. (3) The nitrogen atoms are introduced into a main chain of the polymer, and lone pair electrons of the nitrogen atoms participate in conjugation, so that the overall band gap of the polymer can be further reduced, the polymer can be absorbed to reach a near infrared region, and the absorption of an acceptor material is widened, so that the photocurrent is increased. Meanwhile, the polymer acceptor material is easy to form a film, the preparation difficulty of the device is reduced, and the photo-thermal stability and the morphological stability of the device can be improved, so that the polymer acceptor material can be widely applied to the field of organic solar cells.
Detailed Description
The application provides an organic polymer electron acceptor material, a preparation method and application thereof, and the application is further described in detail below in order to make the purposes, technical schemes and effects of the application clearer and more definite. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the present application.
[ example 1 ]
For the macromolecular receptor P1, the structural formula is
Wherein E is 1 The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. under the protection of nitrogen, 5, 6-binitro-4, 7-dibromobenzothiadiazole (3.84 g,10 mmol) and 2, 5-bistrimethyl tin-thiofuran (4.66 g,10 mmol) are added with Pd (PPh) 3 ) 4 (50 mg) was added to 20mL of toluene, heated to 110℃and refluxed overnight, then blocked with blocking agent E 1 Boric acid esters of radicals E 1 -B (0.23 g,0.5 mmol) and bromo E 1 Br (0.20 g,0.5 mmol), the formula is shown below; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid A1;
B. polymer A1, triethyl phosphite (100 mmol) was added to o-dichlorobenzene (50 mL) under nitrogen blanket and heated at 180℃overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid B1;
C. polymer B1, bromoalkane (14.4 g,40 mmol) was purged with nitrogen
Potassium hydroxide (2.24 g,40 mmol) was added to 50mL of N, N-dimethylformamide and heated at 80deg.C overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P1.
[ example 2 ]
For the macromolecular receptor P2, the structural formula is
Wherein E is 2 The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. under the protection of nitrogen, 5, 6-binitro-4, 7-dibromobenzothiadiazole (3.84 g,10 mmol) and 2, 5-bistrimethyl tin-thiofuran (4.66 g,10 mmol) are added with Pd (PPh) 3 ) 4 (50 mg) was added to 20mL of toluene, heated to 110℃and refluxed overnight, then blocked with blocking agent E 1 Boric acid esters of radicals E 2 -B (0.21 g,0.5 mmol) and bromo E 2 Br (0.18 g,0.5 mmol), of the formula; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid A2;
B. polymer A2, triethyl phosphite (100 mmol) was added to o-dichlorobenzene (50 mL) under nitrogen blanket and heated at 180℃overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid B2;
C. polymer B2, bromoalkane (14.4 g,40 mmol) was purged with nitrogen
Potassium hydroxide (2.24 g,40 mmol) was added to 50mL of N, N-dimethylformamide and heated at 80deg.C overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P2.
[ example 3 ]
For the macromolecular receptor P3, the structural formula is
Wherein E is 1 The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. n-2-ethylhexyl-5, 6-dinitro-4, 7-dibromobenzoazatriazole (4.79 g,10 mmol), 2, 5-bistrimethylstannylthiophene (4.66 g,10 mmol), pd (PPh) under nitrogen 3 ) 4 (50 mg) was added to 20mL of toluene and heated at 110℃backFlowing overnight, then adding end-capping agent for end capping, wherein the end-capping agent adopts E 1 Boric acid esters of radicals E 1 -B (0.23 g,0.5 mmol) and bromo E 1 Br (0.20 g,0.5 mmol), the formula is shown below; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid A3;
B. polymer A3, triethyl phosphite (100 mmol) was added to o-dichlorobenzene (50 mL) under nitrogen blanket and heated at 180℃overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid B3;
C. polymer B3, bromoisooctane (7.72 g,40 mmol) and potassium hydroxide (2.24 g,40 mmol) were added to 50mL of N, N-dimethylformamide under nitrogen and heated at 80deg.C overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P3.
[ example 4 ]
For the macromolecular receptor P4, the structural formula is
Wherein E is 1 The structural formula of the group is as follows:
the preparation process comprises the following steps:
A. n-2-ethylhexyl-5, 6-dinitro-4, 7-dibromobenzoazatriazole (4.79 g,10 mmol), 2, 5-ditrimethylstannyl-4, 8-bis (2-ethyl-1-hexyloxy) benzodithiophene (7.72 g,10 mmol) and Pd (PPh) 3 ) 4 (50 mg) was added to 20mL of toluene, heated to 110℃and refluxed overnight, then blocked with blocking agent E 1 Boric acid esters of radicals E 1 -B (0.23 g,0.5 mmol) and bromo E 1 Br (0.20 g,0.5 mmol), the formula is shown below; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid A4;
B. polymer A4, triethyl phosphite (100 mmol) was added to o-dichlorobenzene (50 mL) under nitrogen blanket and heated at 180℃overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain a polymer solid B4;
C. polymer B4, bromoisooctane (7.72 g,40 mmol) and potassium hydroxide (2.24 g,40 mmol) were added to 50mL of N, N-dimethylformamide under nitrogen and heated at 80deg.C overnight; after the reaction is cooled to room temperature, respectively adopting methanol, normal hexane and chloroform for Soxhlet extraction, pouring a chloroform extraction part into the methanol for precipitation, filtering and drying to obtain the compound P4.
In summary, the present application facilitates electron transport by (1) alternately coupling electron donor components with electron acceptor components to form D-A polymers, lowering the compound bandgap, lowering the LUMO level of the compound. (2) Unlike traditional D-A polymer, the D-A component forms a conjugated plane of the whole polymer main chain through intramolecular cyclization reaction, greatly improves the planarity of the polymer and is beneficial to the transmission of electrons in the polymer and among chains. (3) The nitrogen atoms are introduced into a main chain of the polymer, and lone pair electrons of the nitrogen atoms participate in conjugation, so that the overall band gap of the polymer can be further reduced, the polymer can be absorbed to reach a near infrared region, and the absorption of an acceptor material is widened, so that the photocurrent is increased. Meanwhile, the polymer acceptor material is easy to form a film, the preparation difficulty of the device is reduced, and the photo-thermal stability and the morphological stability of the device can be improved, so that the polymer acceptor material can be widely applied to the field of organic solar cells.
It is to be understood that the application of the present application is not limited to the examples described above, but that modifications and variations can be made by a person skilled in the art from the above description, all of which modifications and variations are intended to fall within the scope of the claims appended hereto.
Claims (5)
1. The organic polymer electron acceptor material is characterized in that the organic polymer electron acceptor material is formed by alternately coupling an electron donor component and an electron acceptor component to form a D-A polymer, and the D-A component forms a conjugated plane of a whole polymer main chain in a longitudinal and transverse manner through intramolecular cyclization reaction, and the molecular structural formula of the organic polymer electron acceptor material is shown as formula I or formula II:
wherein R is 1 ，R 2 Is C 1 -C 20 An alkyl chain of (a), the alkyl chain being a straight or cross chain; ar is any one of the following groups:
wherein R is 3 ，R 4 Is any one of hydrogen atom, alkyl chain, alkoxy chain, alkenyl group, alkynyl group, aryl group or ester group;
EG is any of the following groups:
wherein R is 5 Is any one of a hydrogen atom, a halogen, an alkyl chain, an alkoxy chain, an alkenyl group, an alkynyl group, an aryl group or an ester group.
2. A method for preparing the organic polymer electron acceptor material according to claim 1, wherein the process comprises the following steps:
the method specifically comprises the following steps:
A. coupling 5, 6-binitro-4, 7-dibromobenzothiadiazole with a compound 1 under the catalysis of a catalyst, and then adding a blocking agent to end-cap to generate a polymer solid 2;
B. the polymer 2 reacts with a reducing reagent to close the ring to obtain a condensed ring product 3;
C. polymer 3 with halogenated hydrocarbon R under alkaline conditions 1 X is coupled through carbon and nitrogen to obtain the polymer shown in the formula I.
3. A method for preparing the organic polymer electron acceptor material according to claim 1, wherein the process comprises the following steps:
the method specifically comprises the following steps:
a. coupling N-alkyl-5, 6-binitro-4, 7-dibromo-benzotriazole and a compound 4 under the catalysis of a catalyst, and then adding a blocking agent to block the mixture to generate polymer solid 5;
b. the polymer 5 reacts with a reducing reagent to close the ring to obtain a condensed ring product 6;
c. polymer 6 with halogen under alkaline conditionsSubstituted hydrocarbon R 1 X is coupled through carbon and nitrogen to obtain the polymer shown in the formula II.
4. An organic solar cell device comprising the organic polymer electron acceptor material according to claim 1 or the organic polymer electron acceptor material prepared according to claim 2 or 3.
5. Use of an organic polymeric electron acceptor material according to claim 1 or prepared according to claim 2 or 3 in solar cell devices.
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