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CN-121378732-B - Dihexyl fluorene-long-chain alkyl aniline polymer and preparation method thereof

CN121378732BCN 121378732 BCN121378732 BCN 121378732BCN-121378732-B

Abstract

The invention discloses a dihexyl fluorene-long-chain alkyl aniline polymer and a preparation method thereof, belonging to the technical field of organic high molecular polymers, wherein the structural formula of the polymer is shown as formula (I): The introduction of long-chain alkyl aniline in the polymer does not damage the conjugated structure of the polymer chain, and can properly increase the distance between dihexyl fluorene units and inhibit association phenomenon, thereby being beneficial to obtaining obvious narrow-peak and single-peak fluorescence emission spectrum and pure luminescent color.

Inventors

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Assignees

  • 链行走新材料科技(广州)有限公司

Dates

Publication Date
20260512
Application Date
20251225

Claims (10)

  1. 1. The dihexylfluorene-long-chain alkylaniline polymer is characterized in that the structural formula of the dihexylfluorene-long-chain alkylaniline polymer is shown as formula (II): Formula (II); wherein the number average molecular weight is 50 kDa-150 kDa, and the PDI is 1.5-3.5.
  2. 2. A dihexylfluorene-long-chain alkylaniline polymer according to claim 1, wherein the raw material for the preparation thereof comprises a long-chain alkyl-substituted aniline And 2, 7-dibromo-9, 9-di-n-hexylfluorene 。
  3. 3. The method for preparing dihexyl fluorene-long chain alkyl aniline polymer according to any one of claims 1 to 2, characterized by comprising the steps of: long-chain alkyl substituted aniline under the action of palladium catalyst and auxiliary agent And 2, 7-dibromo-9, 9-di-n-hexylfluorene And (3) reacting to obtain the dihexyl fluorene-long-chain alkyl aniline polymer.
  4. 4. The method for producing a dihexyl fluorene-long-chain alkylaniline polymer according to claim 3, wherein the ratio of the amount of the long-chain alkyl-substituted aniline to the amount of the 2, 7-dibromo-9, 9-di-n-hexylfluorene is 1:1 to 1.1.
  5. 5. The method for producing a dihexylfluorene-long-chain alkylaniline polymer according to claim 3, wherein the ratio of the amount of the palladium catalyst to the amount of the 2, 7-dibromo-9, 9-di-n-hexylfluorene is 0.005 to 0.02:1; and/or the palladium catalyst has a structure shown in the following formula (VI): formula (VI), wherein R 1 、R 2 is independently hydrogen, methyl, ethyl or isopropyl, and R 1 、R 2 is not simultaneously hydrogen.
  6. 6. The method for preparing dihexyl fluorene-long chain alkyl aniline polymer according to claim 3, wherein the reaction temperature is 100-120 ℃ and the reaction time is 12-36 hours; And/or, the reaction is carried out under an inert gas atmosphere; And/or, the reaction further comprises a post-treatment step after the reaction is finished.
  7. 7. The method for producing dihexylfluorene-long chain alkylaniline polymer according to claim 6, wherein the post-treatment step comprises a step of sedimentation with methanol.
  8. 8. A process for the preparation of dihexylfluorene-long chain alkylaniline polymers according to claim 3, wherein the auxiliary comprises an organic base and a solvent.
  9. 9. The method for preparing dihexylfluorene-long-chain alkylaniline polymer according to claim 8, wherein the organic base is potassium t-butoxide; and/or the ratio of the organic base to the 2, 7-dibromo-9, 9-di-n-hexylfluorene is 2-4:1.
  10. 10. The method for producing dihexylfluorene-long chain alkylaniline polymer according to claim 8, wherein the solvent is toluene; And/or the dosage ratio of the solvent to the 2, 7-dibromo-9, 9-di-n-hexylfluorene is 2L-4 L:1mol.

Description

Dihexyl fluorene-long-chain alkyl aniline polymer and preparation method thereof Technical Field The invention belongs to the field of organic high molecular polymers, and particularly relates to a dihexylfluorene-long-chain alkylaniline polymer and a preparation method thereof. Background Poly dihexylfluorene as a material with remarkable fluorescence characteristics has wide application potential in the fields of organic light emitting devices, biological imaging, light transfer films and the like. However, the hexyl side chain of the polydihexyl fluorene is relatively short, so that strong interaction exists between the chains, association phenomenon is easy to generate, the fluorescence emission spectrum has red shift and obvious defects of broad peak and multiple peaks, and the luminescent color correspondingly shows bluish green with unpure, so that the application of the polydihexyl fluorene in the pure-color luminescent field is limited. Therefore, there is a need in the art to provide a polydihexyl fluorene fluorescent material having a pure emission color. Disclosure of Invention Aiming at the defects in the prior art, the dihexyl fluorene-long-chain alkylaniline polymer and the preparation method thereof are provided, and the dihexyl fluorene-long-chain alkylaniline polymer structurally comprises dihexyl fluorene units and long-chain alkylaniline units, on one hand, the long-chain alkylaniline is not a large-volume and twisted non-coplanar monomer, the conjugated structure of a polymer chain is not damaged by the introduction of the long-chain alkylaniline, on the other hand, the distance between the dihexyl fluorene units can be properly increased by the introduction of the long-chain alkylaniline, the association phenomenon is inhibited, and the obvious narrow-peak and single-peak fluorescence emission spectrum and the corresponding pure luminescence color can be obtained. The invention aims to provide a dihexyl fluorene-long-chain alkyl aniline polymer, and the structural formula of the dihexyl fluorene-long-chain alkyl aniline polymer is shown as a formula (I): Formula (I); Wherein R is alkyl with 5-12 carbon atoms, the number average molecular weight is 50-150 kDa, and PDI is 1.5-3.5. In some embodiments of the invention, R is pentyl, hexyl, octyl, or dodecyl. In some embodiments of the invention, the dihexylfluorene-long chain alkylaniline polymer has a structural formula shown in formula (II): formula (II); wherein the number average molecular weight is 50 kDa-150 kDa, and the PDI is 1.5-3.5. In some embodiments of the invention, the dihexylfluorene-long chain alkylaniline polymer has a structural formula shown in formula (III): formula (III); wherein the number average molecular weight is 80kDa to 95kDa, and the PDI is 2.0 to 2.5. In some embodiments of the invention, the dihexylfluorene-long chain alkylaniline polymer has a structural formula shown in formula (IV): Formula (IV); Wherein the number average molecular weight is 70kDa to 85kDa and the PDI is 2.5 to 3.0. In some embodiments of the invention, the dihexylfluorene-long chain alkylaniline polymer has a structural formula shown in formula (V): Formula (V); wherein the number average molecular weight is 65 kDa-75 kDa, and the PDI is 2.2-2.8. In some embodiments of the invention, the dihexylfluorene-long-chain alkylaniline polymer is prepared from a material comprising long-chain alkyl-substituted anilineAnd 2, 7-dibromo-9, 9-di-n-hexylfluorene。 The invention also aims to provide a preparation method of the dihexyl fluorene-long-chain alkyl aniline polymer, which comprises the following steps: long-chain alkyl substituted aniline under the action of palladium catalyst and auxiliary agent And 2, 7-dibromo-9, 9-di-n-hexylfluoreneAnd (3) carrying out a raw reaction to obtain the dihexyl fluorene-long-chain alkyl aniline polymer. In some embodiments of the invention, the ratio of the amount of the long-chain alkyl-substituted aniline to the amount of the 2, 7-dibromo-9, 9-di-n-hexylfluorene is 1:1 to 1.1. In some embodiments of the invention, the ratio of the amount of the palladium catalyst to the amount of the 2, 7-dibromo-9, 9-di-n-hexylfluorene material is 0.005 to 0.02:1. In some embodiments of the invention, the palladium catalyst has a structure represented by the following formula (VI): formula (VI); Wherein R 1、R2 is independently hydrogen, methyl, ethyl or isopropyl, and R 1、R2 is not simultaneously hydrogen. In some embodiments of the invention, the auxiliary comprises an organic base and a solvent. In some embodiments of the invention, the organic base is potassium tert-butoxide. In some embodiments of the invention, the ratio of the organic base to the amount of the 2, 7-dibromo-9, 9-di-n-hexylfluorene material is 2-4:1. In some embodiments of the invention, the solvent is toluene. In some embodiments of the invention, the ratio of the solvent to the 2, 7-dibromo-9, 9-di-n-hexylfluorene is 2L-4 L:1mol. In some embodiments o