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Preparation method of fluorescent polymer and application of 2,2,6,6-tetraalkyl piperidine oxide

A tetraalkylpiperidine, fluorescent polymer technology, used in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of few reports, how to control the performance of fluorescent polymers, etc., and achieve a wide range of application prospects. Effect

Active Publication Date: 2019-07-19
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Dibenzothiophene sulfone is an important fluorescent compound, and most studies focus on its derivatization and modification, but there are very few reports on its introduction into polymer side chains to form fluorescent polymers
CN107814916A, CN106243329A and CN106117524A disclose a fluorescent polymer luminescent material, but none of them involve how to regulate the performance of fluorescent polymers containing dibenzothiophene sulfone

Method used

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  • Preparation method of fluorescent polymer and application of 2,2,6,6-tetraalkyl piperidine oxide
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  • Preparation method of fluorescent polymer and application of 2,2,6,6-tetraalkyl piperidine oxide

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[0035]

[0036] The preparation method of the fluorescent polymer of the present invention includes (1) a fluorescent monomer synthesis step and (2) a living radical polymerization step, which will be described in detail below.

[0037] In the fluorescent monomer synthesis step (1), 3-vinyl-6-phenothiazine dibenzothiophene sulfone is synthesized from dibenzothiophene; it includes the synthesis process of 3,6-dibromodibenzothiophene, 3,6-dibromodibenzothiophene sulfone synthesis process, 3-vinyl-6-bromodibenzothiophene sulfone synthesis process and 3-vinyl-6-phenothiazine dibenzothiophene sulfone synthesis process.

[0038] During the synthesis of 3,6-dibromodibenzothiophene, add dibenzothiophene to chloroform at a temperature below 0°C, then add the chloroform solution containing liquid bromine dropwise, and react at 20-30°C for 2-3 After the reaction was completed, 3,6-dibromodibenzothiophene was obtained by purification. The dosage of dibenzothiophene is 27-30mmol, prefer...

Embodiment 1

[0069] (1) Synthesis of fluorescent monomer 3-vinyl-6-phenothiazine dibenzothiophene sulfone:

[0070] ①Synthesis of intermediate 3,6-dibromodibenzothiophene

[0071]

[0072] In an ice-water bath, 27.2 mmol of dibenzothiophene was added to a single-necked flask containing 30 ml of chloroform, and then a chloroform solution (obtained by dissolving 4 ml of liquid bromine in 5 ml of chloroform) was added dropwise, and reacted at 25°C for 2 days. After the reaction, add 30ml saturated NaHSO 3 The organic layer was extracted with an aqueous solution, and the organic layer was poured into a separatory funnel, extracted three times with dichloromethane, and washed three times with saturated NaCl aqueous solution until the aqueous layer became colorless. The organic layer was dried with anhydrous sodium sulfate and filtered, and the obtained filtrate was spin-dried in a rotary evaporator to obtain 8.54 g of a white solid with a yield of 92%.

[0073] ②Synthesis of 3,6-dibromodib...

Embodiment 2

[0086] (1) Synthesis of fluorescent monomer 3-vinyl-6-phenothiazine dibenzothiophene sulfone:

[0087] It is the same as that of Embodiment 1 and will not be repeated here.

[0088] (2) Synthesis of fluorescent polymer PDPD-2

[0089] Add 0.03mmol of AIBN, 0.039mmol of TEMPO, 2mL of DMF and 3mmol of 3-vinyl-6-phenothiazine dibenzothiophene sulfone into a 5ml polymerization bottle, and seal it after freezing with liquid nitrogen three times and exhausting with argon Polymer bottle. Stir at 70°C for 24h, then raise the temperature to 135°C for 48h, quench to terminate the reaction; pour the reaction liquid into 20-30 times the volume of ethanol, filter, wash the filter cake with ethanol repeatedly for 3 times, filter, and vacuum-dry. The light yellow powder polymer PDPD-2 was obtained. Fluorescence performance test results see figure 1 .

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Abstract

The invention discloses a preparation method of a fluorescent polymer. The method comprises the following steps: synthesizing 3-vinyl-6-thiophenylamine dibenzothiophene sulfone from dibenzothiophene as a raw material; taking 3-vinyl-6-thiophenylamine dibenzothiophene sulfone as a fluorescent monomer, and carrying out a living radical polymerization reaction to obtain the fluorescent polymer underthe condition of the presence of a radical initiator and 2,2,6,6-tetraalkylpiperidine oxide, wherein the alkyl in the 2,2,6,6-tetraalkylpiperidine oxide is C1-C3 alkyl; the radical initiator is selected from an azo initiator or a peroxide initiator; a molar ratio of the radical initiator to the fluorescent polymer is (0.003-0.03):1; and a molar ratio of the radical initiator to the 2,2,6,6-tetraalkylpiperidine oxide is 1:(1-2). The invention further provides application of the 2,2,6,6-tetraalkylpiperidine oxide. According to the method disclosed by the invention, the fluorescent polymer with controllable performance can be obtained.

Description

technical field [0001] The invention relates to a preparation method and application of a fluorescent polymer, in particular to a preparation method and application of a thermally active delayed fluorescent polymer. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of fast response, low driving voltage, flexibility, and active light emission, and are highly valued by related industries. The theoretical limit value of the quantum efficiency of the fluorescent OLED based on singlet emission is only 25%, which is difficult to further improve. The internal quantum efficiency of the device using the triplet light-emitting phosphorescent material can reach 100%, but it has problems such as poor stability and short life. [0003] At present, most phosphorescent materials are based on complexes formed by non-renewable noble metal ions such as Ir and Pt, which are expensive, resulting in high cost of OLED devices. The low triplet energy level o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F112/32C07D417/04C09K11/06
CPCC07D417/04C08F112/32C08F2438/02C09K11/06C09K2211/1458C09K2211/1483
Inventor 任忠杰李晨森闫寿科李慧慧孙晓丽
Owner BEIJING UNIV OF CHEM TECH
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