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Hyperbranched electroluminescent polymer as well as polymerization monomer, preparation method and application thereof

A technology of polymerizing monomers and luminescence, which is applied in the direction of chemical instruments and methods, applications, luminescent materials, etc., and can solve the problems of restricting wide application, low luminous efficiency, poor color purity, etc.

Active Publication Date: 2021-03-19
CHINA PETROLEUM & CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The development of red and green light polymers for full-color flat panel displays has been very mature. However, blue light polymers still cannot meet the market display needs, mainly due to low luminous efficiency, short device life, poor color purity and spectral stability. sex difference
[0003] Polyfluorene has the advantages of excellent fluorescence quantum yield, thermal stability and electrochemical stability, and is widely used to construct blue light polymers. Not ideal, limiting its wide application

Method used

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  • Hyperbranched electroluminescent polymer as well as polymerization monomer, preparation method and application thereof
  • Hyperbranched electroluminescent polymer as well as polymerization monomer, preparation method and application thereof
  • Hyperbranched electroluminescent polymer as well as polymerization monomer, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0068] One, the preparation of polymerized monomer (S1)

[0069] (1) Preparation of 2,2'-dibromo-5'-(2-bromophenyl)-1,1':3',1"-triphenyl (C1)

[0070] In a 100 mL single-necked bottle, 2-bromoacetophenone (9.95 g, 50 mmol) was dissolved in 1 mL of trifluoromethanesulfonic acid, and reacted at 130° C. for 8 hours. The reaction was stopped, quenched with water, extracted with dichloromethane and dried with anhydrous magnesium sulfate. After the solution was concentrated, a black liquid was obtained, which was purified by silica gel column chromatography, using petroleum ether as eluent, and the yield was 73%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0071]

[0072] (2) (2"-Bromo-5'-(2-bromophenyl)-[1,1':3',1"-triphenyl]-2-yl)(methyl)sulfide (C2) preparation of

[0073] Under argon atmosphere, 2,2'-dibromo-5'-(2-bromophenyl)-1,1':...

Embodiment 1

[0119] Embodiment 1: the synthesis of hyperbranched polymer BP1

[0120] Under argon atmosphere, 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (321mg, 0.50mmol), 2,7-dibromo-9,9-dioctylfluorene (264.9mg, 0.485mmol) and polymerized monomer S1 (8.5mg, 0.01mmol) were added to a 50mL two-necked bottle, and then 12mL Refined toluene, then added palladium acetate (2.80 mg, 12.45 μmol) and tricyclohexylphosphine (6.98 mg, 24.90 μmol), then added 3 mL of tetraethylammonium hydroxide, raised the temperature to 80 ° C, and reacted for 24 hours; then added 20 mg of benzene Boric acid was capped, and after 12 hours, it was capped with 0.3mL bromobenzene; after the reaction was continued for 12 hours, the reaction was stopped, and when the temperature dropped to room temperature, the product was dropped in 300mL of methanol for precipitation, filtered, and the crude The product was dissolved in 20mL of toluene, 200-300 mesh silica gel was used as the stationary ...

Embodiment 2

[0124] Example 2: Synthesis of Polymer BP2

[0125] Under argon atmosphere, 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (321mg, 0.50mmol), 2,7-dibromo-9,9-dioctylfluorene (256.7mg, 0.47mmol) and polymerized monomer S1 (17mg, 0.02mmol) were added to a 50mL two-necked bottle, and then 12mL was added to refine Add toluene, then add palladium acetate (2.80 mg, 12.45 μmol) and tricyclohexylphosphine (6.98 mg, 24.90 μmol), then add 3 mL of tetraethylammonium hydroxide, heat up to 80 ° C, and react for 24 hours; then add 20 mg of phenylboronic acid After 12 hours, use 0.3mL bromobenzene to carry out capping; after continuing to react for 12 hours, stop the reaction, wait until the temperature drops to room temperature, add the product dropwise to 300mL methanol for precipitation, filter, and then the crude product Dissolve in 20mL of toluene, use 200-300 mesh silica gel as the stationary phase, and use toluene as the eluent for column chromatography. The...

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Abstract

The invention discloses a hyperbranched electroluminescent polymer as well as a polymerization monomer, a preparation method and application thereof, and belongs to the technical field of organic photoelectricity. The structure of the electroluminescent polymer is shown as a formula (II), and a sulfuryl-containing three-dimensional asymmetric polycyclic aromatic structure can improve the thermal stability, the fluorescence quantum yield and the carrier transport capability of a luminescent material, so that a luminescent device can obtain efficient and stable luminescent device performance; and the polymer has large steric hindrance, and is a potential dark blue light emitting polymer. The electroluminescent polymer provided by the invention has good solubility, can be dissolved by adopting a common organic solvent, and can be prepared into a light-emitting layer of a light-emitting diode through spin coating, ink-jet printing or printing film formation.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a hyperbranched electroluminescent polymer, a polymerized monomer, a preparation method and an application thereof. Background technique [0002] Polymer organic light-emitting diodes (PLEDs) have the advantages of low energy consumption and low-voltage drive, and can be used in the preparation of flexible displays, solid-state lighting and other fields. The development of red and green light polymers for full-color flat panel displays has been very mature. However, blue light polymers still cannot meet the market display needs, mainly due to low luminous efficiency, short device life, poor color purity and spectral stability. Poor sex and so on. [0003] Polyfluorene has the advantages of excellent fluorescence quantum yield, thermal stability and electrochemical stability, and is widely used to construct blue light polymers. Not ideal, which limits...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D333/78C08G61/12C09D165/00C09D11/30C09D11/102C09D11/50
CPCC09K11/06C07D333/78C08G61/126C09D165/00C09D11/30C09D11/102C09D11/50C08G2261/132C08G2261/122C08G2261/5222C08G2261/514C08G2261/1412C08G2261/3142C08G2261/3243C08G2261/3162C08G2261/314C08G2261/3247C08G2261/3241C08G2261/312C08G2261/3242C09K2211/1092C09K2211/1458C09K2211/1425H10K85/113
Inventor 郭婷马泓文捷胡黎文应磊彭俊彪曹镛
Owner CHINA PETROLEUM & CHEM CORP
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