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Siloxane group-containing A-DA 'D-A type conjugated organic small molecule as well as preparation method and application thereof

An A-DA, siloxane-based technology, applied in the field of A-DA'D-A type conjugated organic small molecules and their preparation, can solve the problems of hindering π-π interaction, affecting charge transport, etc., to increase the intermolecular Effects of interaction force, high electron mobility, high charge transport performance

Pending Publication Date: 2022-07-22
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the steric hindrance effect, although the second longer branched aliphatic side chain ensures better solubility, it will hinder the π-π interaction between the Y series small molecule acceptor and the main chain molecule, and thus affect its charge transport

Method used

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  • Siloxane group-containing A-DA 'D-A type conjugated organic small molecule as well as preparation method and application thereof
  • Siloxane group-containing A-DA 'D-A type conjugated organic small molecule as well as preparation method and application thereof
  • Siloxane group-containing A-DA 'D-A type conjugated organic small molecule as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1 Synthesis of Y6-Si containing siloxane-based organic small molecules

[0059] The present embodiment relates to the preparation of a siloxane-containing A-DA'D-A type conjugated organic small molecule Y6-Si, and the reaction scheme is as follows:

[0060]

[0061] The specific synthesis steps are as follows:

[0062] (1) Synthesis of compound 2

[0063] 3-Undecylthieno[3,2-B]thiophene (27mmol, 7.95g) was dissolved in 100mL of tetrahydrofuran solvent, n-butyllithium (27mmol, 11.34mL) was slowly added under acetone bath, after 2 hours Add tributyltin Bu 3 SnCl (27mmol, 8.78g), then removed the acetone bath, stirred overnight at room temperature, added deionized water to quench the reaction, extracted the organic phase with ethyl acetate, evaporated the solvent, anhydrous MgSO 4 Compound 2 was prepared after drying.

[0064] (2) Synthesis of compound 4

[0065] Under the condition of 110°C, compound 2 (25mmol, 14.6g) prepared in step (1), compound 3 (10mm...

Embodiment 2

[0082] Example 2 Synthesis of Y6-Si-Cl containing siloxane-based organic small molecules

[0083] The present embodiment relates to the preparation of a siloxane-containing A-DA'D-A type conjugated organic small molecule Y6-Si-Cl, and the reaction scheme is as follows:

[0084]

[0085] where R 1 for -C 11 H 23 .

[0086] The specific synthesis steps are as follows:

[0087] Steps (1) to (5) are the same as in Example 1.

[0088] (6) Synthesis of compound 11:

[0089] Compound 9 (0.50 mmol, 706 mg), 5,6-dichloro-3-(dicyanomethylene)indigo (1.50 mmol, 395 mg), pyridine (0.5 mL) and chloroform (20 mL) were mixed under nitrogen Dissolve in a 100mL two-neck round bottom bottle. The reaction was stirred at 65°C overnight. After cooling to room temperature, the mixture was poured into methanol for sedimentation, and the crude product was obtained after suction filtration. The crude product was purified by silica gel column chromatography, using dichloromethane / petroleum e...

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Abstract

The invention discloses a siloxane group-containing A-DA 'D-A type conjugated organic small molecule and a preparation method and application thereof, a diazosulfide unit is taken as a center, a pyrrole ring and two thiophenes are connected in parallel outwards to form a seven-membered fused ring structure which is taken as a molecular core, siloxane is used for blocking a side chain of a pyrrole ring nitrogen atom, and the siloxane group-containing A-DA' D-A type conjugated organic small molecule is obtained. And a series of siloxane group-containing A-DA 'D-A type conjugated organic small molecules are designed and synthesized by changing different acceptor units. The molecules have the advantages of strong light absorption capability, high mobility and proper electron energy level, and can be used as electron acceptor materials for preparing organic solar cells. The siloxane-terminated side chain of the organic small molecule prepared by the invention has a plurality of far-branched Si-O hybrid chains, so that the steric hindrance of the molecule can be effectively reduced, the interaction among the molecules is increased, the pi-pi stacking distance is reduced, and meanwhile, the molecule shows good solubility in a halogen-free solvent; and the halogen-free solvent and printing technology processing of the high-performance organic solar cell can be realized.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and organic photovoltaic materials, in particular to a siloxane group-containing A-DA'D-A type conjugated organic small molecule and a preparation method and application thereof. Background technique [0002] Solution-processable organic solar cells are a green energy technology with unique advantages such as low cost, light weight, and the ability to fabricate large-area devices (X.Guo, Q.Fan and et al.Nat.Commun., 2020, 11, 4612; S. Park, T. Kim and et al. Adv. Mater., 2020, 32, 2002217; H. Chen, R. Zhang and et al. Nat. Energy, 2021, 6, 1045.). In 2019, Yingping Zou's research group reported a star small molecule-Y6 with A-DA'D-A structure, which has a wide absorption range, high absorption coefficient, unique and effective charge transport and exciton delocalization. 3D network. PM6:Y6-based PSCs achieved an astonishing PCE as high as 15.7% when Y6 was matched with the narrow-bandgap polym...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18H01L51/42H01L51/46
CPCC07F7/1804C07F7/1876C07F7/1892H10K85/626H10K85/615H10K85/657H10K85/40H10K30/00
Inventor 张茂杰肖海芹国霞
Owner SUZHOU UNIV
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