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A kind of conjugated organic small molecule containing double-terminal pyridine and its preparation method and application

A technology of terminal pyridine and small molecules, which is applied in the field of solar cells, can solve the problems of reducing battery performance, affecting the morphology and compactness of perovskite light-absorbing layers, and poor contact, so as to achieve hysteresis suppression and energy conversion efficiency and open-circuit photovoltage increase, improve the effect of short-circuit photocurrent

Active Publication Date: 2022-05-20
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The uneven surface of nickel oxide leads to poor contact between the perovskite light-absorbing layer and nickel oxide, which affects the morphology and compactness of the perovskite light-absorbing layer, thereby reducing the performance of the battery

Method used

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  • A kind of conjugated organic small molecule containing double-terminal pyridine and its preparation method and application
  • A kind of conjugated organic small molecule containing double-terminal pyridine and its preparation method and application
  • A kind of conjugated organic small molecule containing double-terminal pyridine and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: When X=S, m=0, n=6, the preparation of conjugated small organic molecules (referred to as PTZ-1)

[0041] Prepared according to the literature method [M.Sailer, M.Nonnenmacher, T.Oeser and T.J.J.Müller.Eur.J.Org.Chem.2006,423–435], specifically: using 1,4-dioxane as a solvent, Compound e (X=S, m=0) and bisboronic acid substituted phenothiazine d (X=S, n=6) were mixed at a molar ratio of 3:1, and Pd(PPh 3 ) 4 Reaction with potassium carbonate and water at 80°C for 24 hours, and the product PTZ-1 was obtained as a yellow solid through column chromatography with a yield of 78%. 1 H NMR 8.59(d, J=4.8Hz, 4H), 7.43~7.45(m, 8H), 6.94(d, J=8.4Hz, 2H), 3.89(t, J=7.2Hz, 2H), 1.83(m ,2H),1.47(m,2H),1.32(m,4H),0.89(t,J=6.4Hz,3H). 13 C NMR (100MHz, DMSO-d 6 ) 149.9, 147.0, 145.5, 132.0, 128.4, 125.5, 124.7, 120.7, 115.7, 47.7, 31.3, 26.6, 26.5, 22.5, 13.9. ESI-HRMS (m / z): Calcd.for C 28 h 27 N 3 S: 438.1998. Found: 438.1998.

Embodiment 2

[0042] Example 2: When X=S, m=1, and n=6, the preparation of conjugated small organic molecules (referred to as PTZ-2):

[0043] Specifically: using 1,4-dioxane as a solvent, compound e (X=S, m=1) and bisboronic acid-substituted phenothiazine d (X=S, n=6) in a molar ratio of 2.5: 1 mix. Add Pd(PPh 3 )4 React with potassium carbonate and water at 80°C for 24h, and get the product PTZ-2 through column chromatography with a yield of 68%. 1 H NMR (400MHz, DMSO-d 6 )8.78(d, J=6.0Hz, 4H), 7.94~7.95(m, 4H), 7.86~7.89(m, 4H), 7.78~7.82(m, 4H), 7.06(d, J=8.8Hz, 2H ),3.99(t,J=7.2Hz,2H),1.94(m,2H),1.52(m,2H),1.38(m,4H),0.92(t,J=7Hz,3H). 13 C NMR (100MHz, DMSO-d 6 ) 150.1, 144.6, 133.7, 131.3, 129.6, 128.8, 128.5, 127.9, 126.7, 124.4, 123.5, 115.3, 47.8, 31.5, 26.8, 26.7, 22.6, 14.0. ESI-HRMS (m / z): Calcd.for C 40 h 31 N 7 S 3 :706.1896. Found: 706.1876.

Embodiment 3

[0044] Embodiment 3: When X=S, m=0, n=1, the preparation of conjugated small organic molecules (referred to as PTZ-3)

[0045] Prepared according to the literature method [M.Sailer, M.Nonnenmacher, T.Oeser and T.J.J.Müller.Eur.J.Org.Chem.2006,423–435], specifically: using 1,4-dioxane as a solvent, Compound e (X=S, m=0) and bisboronic acid substituted phenothiazine d (X=S, n=1) were mixed at a molar ratio of 3:1, and Pd(PPh 3 ) 4 Reaction with potassium carbonate and water at 85°C for 20 h, the product PTZ-3 was obtained as a yellow solid through column chromatography, and the yield was 76%.

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Abstract

The invention belongs to the technical field of solar cells, in particular to a conjugated organic small molecule containing double-end pyridine and a preparation method and application thereof. Taking the conjugated organic small molecule based on double-end pyridine as the basic molecular framework, the energy level of the molecule and the degree of conjugation of the molecule are adjusted by introducing electron withdrawing groups. Conjugated organic small molecules based on double-ended pyridines as hole transport materials were self-assembled onto nickel oxide surfaces for application in perovskite solar cells. The invention is beneficial to suppress the hysteresis of the solar cell, improve the short-circuit photocurrent, and facilitate the conduction of electric charges; under simulated sunlight irradiation, the perovskite solar cell device based on nickel oxide modified by conjugated organic small molecules The energy conversion efficiency and open-circuit photovoltage were significantly improved, respectively. The conjugated organic small molecule containing double-end pyridine of the present invention has the advantages of simple structure, easy preparation and high stability, and is a kind of potential interface modification material which can be applied to perovskite solar cells.

Description

technical field [0001] The invention belongs to the technical field of solar cells, and in particular relates to a conjugated organic small molecule containing double-terminal pyridine, a preparation method thereof and an application in a perovskite solar cell. Background technique [0002] As a new type of photovoltaic device, perovskite solar cells (Perovskite solar cells) have attracted extensive attention from academia and industry. The perovskite light-absorbing layer has the advantages of high molar extinction coefficient, wide light absorption range, and long carrier diffusion length. In just a few years, its energy conversion efficiency has rapidly increased from the initial 3.8% to 23.2%. There are two types of perovskite solar cells, forward and reverse. In the reverse structure (P-I-N), PEODT:PSS, PTTA or NiO are usually used as the hole transport layer, but because PEODT:PSS is acidic and easy to absorb water, PTTA needs to be doped with lithium salt, which aff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14C07D413/14H01L51/42H01L51/46
CPCC07D417/14C07D413/14H10K85/654H10K85/6572H10K85/657H10K30/10Y02E10/549
Inventor 王忠胜程浩亮李亚茹
Owner FUDAN UNIV
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