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CN-121990939-A - Benzamide derivative and preparation method and application thereof

CN121990939ACN 121990939 ACN121990939 ACN 121990939ACN-121990939-A

Abstract

The invention belongs to the technical field of battery preparation, and particularly relates to a benzamide derivative and a preparation method and application thereof. The molecule contains trifluoromethyl and amido with strong electron withdrawing and is set in meta position, and indole groups which can promote efficient extraction of charges and inhibit interface recombination can effectively regulate and control the crystallization process of perovskite thin film and passivate surface and interface defects. The derivative is used as an additive to be added into a perovskite precursor, so that the filling factor and the power conversion efficiency of a trans-perovskite device can be remarkably improved. The invention also provides a simple preparation method of the derivative, which has the advantages of easily available raw materials, mild reaction conditions and high yield, and provides a new technical scheme for preparing the high-performance trans-perovskite device.

Inventors

  • DING YE
  • LI WANYI
  • ZHAO JIARUI

Assignees

  • 中茂绿能科技(西安)有限公司

Dates

Publication Date
20260508
Application Date
20260211

Claims (9)

  1. 1. The structure of the benzamide derivative is shown as a formula (1): Formula (1); Wherein L represents a- (CH 2 ) n alkyl chain, n is 0-2, R represents any one of a hydrogen atom, 3-methyl-1H-indol-5-yl) oxy group, (3-ethyl-1H-indol-5-yl) oxy group or (3-isopropyl-1H-indol-5-yl) oxy group.
  2. 2. The benzamide derivative according to claim 1, wherein the benzamide derivative is any one of the following compounds A1 to A3 and B1 to B3; 。
  3. 3. a method for preparing a benzamide derivative according to claim 2, wherein the preparation process of the compounds A1 and A2 specifically comprises the following steps: Bromobenzene or bromobenzyl is used as a raw material, and carboxylic acid intermediates are obtained through an organometal reagent-mediated carboxylation reaction; The method comprises the steps of taking N, N-dimethylformamide as a catalyst, carrying out an acylation reaction on a carboxylic acid intermediate and thionyl chloride under a heating reflux condition to generate an acyl chloride intermediate, carrying out ammonolysis reaction for crystallization, and drying to obtain the catalyst; the preparation process of the compound A3 specifically comprises the following steps: Palladium acetate and tri (o-methylphenyl) phosphorus are used as a catalytic system, N-diisopropylethylamine is used as alkali, bistrifluoromethyl bromobenzene and acrylamide are mixed according to the mass ratio of 11-11.1:4-4.1, heck coupling reaction is carried out, methanol-water recrystallization is carried out after reaction liquid is extracted, dried and concentrated, an enamide intermediate is obtained, raney nickel is used as a hydrogenation catalyst and ethanol is used as a solvent, catalytic hydrogenation reduction reaction is carried out on the enamide intermediate under a protective atmosphere, double bonds are reduced, saturated amide is obtained, and the reaction liquid is subjected to catalyst removal, concentration and drying.
  4. 4. A process for producing a benzamide derivative according to claim 3, characterized in that, A1, taking n-butyllithium as an organic metal reagent, and performing carboxylation reaction on a bromobenzene raw material after hydrogen is extracted, wherein the molar mass ratio of the n-butyllithium to bromobenzene is 45.05-45.15:37.54-37.64; a2, taking magnesium chips as an organic metal reagent, preparing a Grignard reagent with a bromobenzyl raw material, and then completing carboxylation reaction with dry ice, wherein the reaction liquid is subjected to extraction, pH adjustment by dilute hydrochloric acid and crystallization to obtain a carboxylic acid intermediate, and the mass ratio of the magnesium chips to the bromobenzyl is 1.04-1.14:12.00-12.10; The mass ratio of the N, N-diisopropylethylamine to the bis (trifluoromethyl) bromobenzene is 9.7-9.75:0.94-0.99:11-11.05, and the mass ratio of palladium acetate to tris (o-methylphenyl) phosphorus in the catalytic system is 0.25-0.30:0.69-0.74.
  5. 5. The preparation method of the benzamide derivative as claimed in claim 2, wherein the preparation process of the compounds B1 to B3 is specifically as follows: Taking the intermediate B as a substrate, respectively reacting with any one of 5-hydroxy-3-methylindole, 5-hydroxy-3-ethylindole and 5-hydroxy-3-isopropylindole as a reactant, taking potassium carbonate as alkali and dimethyl sulfoxide as a solvent, heating to 120-125 ℃ for 4-4.5 hours, extracting, separating out solids, directly filtering, and drying to obtain corresponding target compounds B1-B3; in the preparation process of the compound B1, the mass ratio of the intermediate B to the reactant is 3.00-3.05:1.69-1.74; in the preparation process of the compound B2, the mass ratio of the intermediate B to the reactant is 4.00 g-4.05 g, 2.46 g-2.51 g; In the preparation process of the compound B3, the mass ratio of the intermediate B to the reactant is 3.00 g-3.05 g:2.10 g-2.15 g; the structural formula of the compound B is as follows: 。
  6. 6. Use of a benzamide derivative of claim 2 in the preparation of a perovskite battery additive, said perovskite battery additive being added to a perovskite light absorbing layer.
  7. 7. The application of claim 6, wherein the addition amount of the benzamide derivative is 1% -1.5% of the mass of the perovskite light absorbing layer.
  8. 8. A perovskite solar cell is characterized by comprising an anode, a hole transmission layer, a perovskite light absorption layer, an electron transmission layer and a cathode, wherein the benzamide derivative of claim 1 is added into the perovskite light absorption layer.
  9. 9. The perovskite solar cell according to claim 8, wherein the perovskite light absorbing layer is obtained in the following specific process: After adding the benzamide derivative into a perovskite precursor solution, depositing a perovskite film on the hole transport layer by using chlorobenzene as an antisolvent through a one-step method, and annealing to obtain a perovskite light absorption layer; The molar quantity of the benzamide derivative in the perovskite precursor solution is 0.1-0.2 mmol.

Description

Benzamide derivative and preparation method and application thereof Technical Field The invention belongs to the technical field of battery preparation, and particularly relates to a benzamide derivative and a preparation method and application thereof. Background At present, perovskite Solar Cells (PSCs) have become research hot spots in the photovoltaic field due to the advantages of high power conversion efficiency, low preparation cost, solution processability and the like. The trans-perovskite device (p-i-n structure) has the characteristics of simple structure, low preparation temperature, good stability and the like, is more suitable for preparing a laminated device with a silicon-based solar cell, and has wide commercial application prospect. However, the performance and stability of trans-perovskite devices is still limited by the crystalline quality of the perovskite thin film, the surface and interface defect density, and the energy level mismatch between the perovskite and the charge transport layer. Meanwhile, the energy level mismatch between perovskite and a hole transport layer such as NiO x and Me-4PACz or an electron transport layer such as C60 and BCP can prevent charge extraction and influence the efficiency of the device. In addition, defects such as pinholes, grain boundaries and the like are easy to form in the crystallization process of the perovskite film, and the performance attenuation of the device is further aggravated. To solve the above problems, methods of adding small organic molecule additives are generally adopted at present to regulate perovskite crystallization, passivate defects and optimize energy level arrangement. For example, aniline derivatives such as Phenethylamine (PEA) and 4-fluorophenylethylamine (F-PEA) are used as additives to passivate defects and improve interface contact by forming coordination bonds between amino groups in molecules and Pb 2+ on the surface of perovskite, and trifluoromethyl-containing compounds can adjust molecular dipole moment due to their strong electron withdrawing property to optimize energy level arrangement. However, the existing additive is difficult to realize three functions of 'regulating crystallization, passivating defects and optimizing energy level'. Disclosure of Invention In order to solve the problems, the invention provides a benzamide derivative, a preparation method and application. The specific technical scheme is as follows. The structure of the benzamide derivative is shown as a formula (1): Formula (1); Wherein L represents a- (CH 2) n alkyl chain, n is 0-2, R represents any one of a hydrogen atom, 3-methyl-1H-indol-5-yl) oxy group, (3-ethyl-1H-indol-5-yl) oxy group or (3-isopropyl-1H-indol-5-yl) oxy group. The 2 meta-CF 3 structures in the invention realize the coordination of strong electron coordination and uniform space limitation, the strong coordination function delays nucleation, provides a time window for uniform nucleation, ensures uniform dispersion of additive molecules by symmetrical space configuration, realizes global growth regulation, inhibits abnormal growth of crystal grains by superposition of steric hindrance effect, and finally obtains the perovskite crystal structure with low defect density, high crystallinity and regular orientation. Compared with a single-CF 3 or 2-CF 3 which are not arranged in the meta position, the perovskite structure cannot achieve the regulation and control targets of uniform nucleation, ordered growth and low defect crystal lattice at the same time due to insufficient synergism of an electronic effect and a steric effect, and finally the perovskite structure cannot achieve better effects in the aspects of uniformity of crystal grain size, lattice integrity and grain boundary quality. In addition, R in the structure is indole ring as nitrogen-containing aromatic heterocycle, and lone pair electrons of ring nitrogen atoms can form strong coordination action with Pb 2+ with low coordination in perovskite crystal lattice through Lewis acid-base reaction, so that cation defects generated by insufficient coordination of Pb 2+ in the perovskite film are accurately passivated. In another preferred embodiment, the benzamide derivative is any one of the following compounds A1 to A3 and B1 to B3; 。 The second aspect of the invention provides a preparation method of the benzamide derivative, and the preparation process of the compounds A1 and A2 is specifically as follows: Bromobenzene or bromobenzyl is used as a raw material, and carboxylic acid intermediates are obtained through an organometal reagent-mediated carboxylation reaction; N, N-dimethylformamide is used as a catalyst, carboxylic acid intermediates and thionyl chloride are subjected to acylation reaction under the condition of heating reflux to generate acyl chloride intermediates, and dichloroethane solution of acyl chloride is directly added into ammonia water solution in a dropwise manner, and is subjected to am