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Fluorescent polymer compound, preparation method and light-emitting device based on polynorbornene main chain and space charge transfer luminescence

A polymer compound, polynorbornene technology, applied in the direction of electrical solid devices, chemical instruments and methods, luminescent materials, etc., can solve the problems that are not conducive to blue light emission, difficult to take care of, and difficult to accurately control the distribution of electron clouds

Active Publication Date: 2021-05-28
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem is that it is difficult to achieve a small ΔE due to the difficulty of precisely controlling the electron cloud distribution of the donor and acceptor in the polymer TADF material. ST and higher PLQY
At the same time, the electron cloud of the main chain of the conjugated polymer has a large degree of delocalization, which is easy to cause a red shift in the emission spectrum of the conjugated polymer, which is not conducive to the realization of blue light emission.

Method used

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  • Fluorescent polymer compound, preparation method and light-emitting device based on polynorbornene main chain and space charge transfer luminescence
  • Fluorescent polymer compound, preparation method and light-emitting device based on polynorbornene main chain and space charge transfer luminescence
  • Fluorescent polymer compound, preparation method and light-emitting device based on polynorbornene main chain and space charge transfer luminescence

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preparation example Construction

[0114] The present invention also provides a method for preparing a fluorescent polymer compound based on polynorbornene main chain and space charge transfer luminescence as described above, comprising the following steps:

[0115] Under protective gas atmosphere, after the monomer of structure shown in formula (X), catalyst and organic solvent are mixed, carry out reaction, obtain the polymer compound shown in formula (I);

[0116] Or under protective gas atmosphere, after the monomer of structure shown in formula (X), the monomer of structure shown in formula (Y), catalyst and organic solvent are mixed, carry out reaction, obtain the polymer shown in formula (II) compound;

[0117]

[0118] The present invention has no special restrictions on the source of the monomers with the structure shown in (X) and the monomers with the structure shown in the formula (Y). They can be prepared by conventional preparation methods well known to those skilled in the art or purchased fro...

Embodiment 1

[0147] Synthesis of monomers:

[0148]

[0149] Under argon atmosphere, 1 (5.5 g, 15 mmol), 2 (8.49 g, 19.5 mmol), potassium carbonate (5.4 g, 39 mmol), 2,5-norbornadiene (6.1 mL, 60 mmol), THF ( 80mL) and H 2 O (40mL) was added in a 250ml two-necked flask, and after the temperature was raised to 60°C, a THF solution (6mL) of triphenylphosphine (0.39g, 1.5mmol) and palladium acetate (0.13g, 0.6mmol) was added to the reaction system, The reaction was stirred at 60°C for 24h in the dark. After cooling to room temperature, the reaction solution was diluted with diethyl ether and washed with saturated brine. The organic phase was separated and dried over anhydrous sodium sulfate, concentrated, and separated on a silica gel column to obtain 3.5 g of a white solid with a yield of 35%.

[0150] C 46 h 34 N 4 Elemental analysis (%): C, 85.82; H, 5.60; N, 8.53.

[0151] According to mass spectrometry (MALDI-TOF), its molecular weight is 643.3.

[0152] Proton NMR spectrum ana...

Embodiment 2

[0158] Synthesis of monomers:

[0159]

[0160] Under argon atmosphere, 3 (10.3 g, 25 mmol), 2 (14.2 g, 32.5 mmol), potassium carbonate (9.0 g, 65 mmol), 2,5-norbornadiene (10.2 mL, 100 mmol), THF ( 100mL) and H 2 O (50mL) was added in the 250ml two-necked flask, after the temperature was raised to 60°C, the THF solution (10mL) of triphenylphosphine (0.66g, 2.5mmol) and palladium acetate (0.22g, 1.0mmol) was added in the reaction system, The reaction was stirred at 60°C for 24h in the dark. After cooling to room temperature, the reaction solution was diluted with diethyl ether and washed with saturated brine. The organic phase was separated, dried over anhydrous sodium sulfate, concentrated, and separated on a silica gel column to obtain 6.9 g of a white solid with a yield of 40%.

[0161] C 49 h 40 N 4 Elemental analysis (%): C, 85.72; H, 5.99; N, 8.11.

[0162] According to mass spectrometry (MALDI-TOF), its molecular weight is 685.3.

[0163] Proton NMR spectrum a...

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Abstract

The invention provides a fluorescent polymer compound based on polynorbornene main chain and space charge transfer light emission, which has the structure shown in formula I or formula II. The invention designs and develops a kind of fluorescent macromolecule material based on the main chain of polynorbornene, the donor and the acceptor are separated in space, and has space charge transfer luminescence. Its norbornene main chain is a non-conjugated structure with a wide band gap, which can easily realize blue light emission. At the same time, the donor and acceptor are spatially separated, which is beneficial to reduce the ΔE ST And realize the TADF effect. By connecting the D and A fragments on the same norbornene unit, the donor and the acceptor can be effectively interacted in space, and the rigid connection method is conducive to suppressing the non-radiative transition process to improve the fluorescence quantum efficiency. The invention also provides a preparation method of fluorescent polymer compound based on polynorbornene main chain and space charge transfer light emission and an organic electroluminescent device.

Description

technical field [0001] The invention belongs to the field of organic light-emitting materials, and in particular relates to a fluorescent polymer compound based on polynorbornene main chain and space charge transfer light emission, a preparation method and an organic electroluminescent device. Background technique [0002] Organic electroluminescence refers to the phenomenon that organic materials emit light under the excitation of electric current or electric field. Organic light-emitting diodes (OLEDs) are considered to be an ideal third-generation display technology to replace liquid crystal technology due to their inherent advantages, such as self-illumination, high brightness, wide viewing angle, fast response, low energy consumption, and flexible display devices. The classic OLED structure adopts a "sandwich" structure, the anode material is mostly indium tin oxide (ITO), and the cathode material is mostly a metal material with a low work function. Holes and electrons...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/08C09K11/06H01L51/50H01L51/54
CPCC08G61/08C09K11/06C09K2211/1466C09K2211/1475C09K2211/1483C09K2211/1491C08G2261/11C08G2261/143C08G2261/144C08G2261/148C08G2261/418C08G2261/149C08G2261/147C08G2261/95C08G2261/5222H10K85/111H10K50/11
Inventor 王利祥邵世洋李强王兴东赵磊吕剑虹
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI