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D-A-pi-A-D type fluorescent compound and preparation method thereof

A fluorescent compound, -A-D technology, applied in chemical instruments and methods, photovoltaic power generation, luminescent materials, etc., can solve problems affecting molecular geometry, stacking and electron density distribution, poor molecular planarity, etc.

Active Publication Date: 2021-10-22
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

D-A-D type molecules have strong intramolecular charge transfer characteristics, which will affect their band gap and absorption characteristics, but are prone to charge recombination; D-π-D type molecules increase the π conjugation length of the molecule through the π bridge, further strengthening the molecule The stacking between them improves its charge transport properties, but its molecular planarity is poor
[0003] Triphenylamine derivatives are commonly used structural units in hole transport materials. It has strong electron donating ability, and its non-planar molecular configuration can inhibit molecular aggregation and form a uniform, smooth and stable film. Terminal functional groups affect molecular geometry, packing and electron density distribution, especially hole mobility

Method used

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  • D-A-pi-A-D type fluorescent compound and preparation method thereof
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  • D-A-pi-A-D type fluorescent compound and preparation method thereof

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Embodiment 1

[0032] A D-A-π-A-D type fluorescent compound, the synthetic route is:

[0033]

[0034] The preparation process is as follows:

[0035] In the first step, 0.43g compound (I), 0.59g compound (II), 0.06g tetrakis(triphenylphosphine)palladium, 26mL2.0mol / L potassium carbonate aqueous solution and 70mL THF were added to a three-necked flask, Heat under reflux (73°C) for 24h, cool, extract with ethyl acetate and water, collect the organic phase, dry over anhydrous magnesium sulfate, separate and purify by column chromatography (eluent, petroleum ether: ethyl acetate 20:1 (volume ratio )) and dried in a vacuum oven after rotary evaporation to obtain 0.26 g of compound (Ⅲ) as a red powder. Characterization data: 1 H NMR (500MHz, DMSO) δ8.07(d, J=7.7Hz, 1H), 7.84(d, J=8.7Hz, 2H), 7.70(d, J=7.7Hz, 1H), 7.13(d, J =8.8Hz, 4H), 6.98(d, J=8.9Hz, 4H), 6.90(d, J=8.7Hz, 2H), 3.79(s, 6H); 13 C NMR (75MHz, DMSO) δ 158.83, 155.90, 155.18, 151.55, 142.32, 135.41, 135.30, 132.54, 129.88, 12...

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Abstract

The invention discloses a D-A-pi-A-D type fluorescent compound and a preparation method thereof, wherein the structural formula of the D-A-pi-A-D type fluorescent compound is shown in the specification, wherein methoxytriphenylamine is used as an electron donor D, benzothiadiazole is used as an electron acceptor A, and carbazole is a pi bridge. The D-A-pi-A-D type fluorescent compound disclosed by the invention has the advantages that the energy level is easy to adjust and the pi conjugate length is easy to prolong so as to improve the charge transport property, has good symmetry and higher thermal stability and morphological stability, is an excellent fluorescent compound, and can be applied to perovskite solar cells (PSCs) as a hole transport material.

Description

technical field [0001] The invention relates to a D-A-π-A-D fluorescent compound and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Hole transport materials (HTMs) are important components in perovskite solar cells (PSCs), which play important roles in transporting holes, blocking carrier recombination, and protecting the perovskite layer. Two commonly used design strategies for linear small molecule hole transport materials are the D-A-D and D-π-D structures, where D, A, and π correspond to the electron donor, electron acceptor, and π bridge, respectively. D-A-D type molecules have strong intramolecular charge transfer characteristics, which will affect their band gap and absorption characteristics, but are prone to charge recombination; D-π-D type molecules increase the π conjugation length of the molecule through the π bridge, further strengthening the molecule Interstitial stacking improves its charge t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06H01L51/46
CPCC07D417/14C09K11/06C09K2211/1051C09K2211/1029H10K85/657H10K85/6572Y02E10/549
Inventor 高宏窦立薇高亚楠商士斌宋湛谦
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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