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Electroluminescent monomer and polymer and preparation and application methods thereof

A luminescence and polymer technology, applied in the direction of electrical solid-state devices, semiconductor/solid-state device manufacturing, circuits, etc., can solve the problems of reducing the color purity and efficiency of devices

Active Publication Date: 2018-09-28
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The rigidity and planarity of indenofluorene are improved, and its optical, chemical and electrical properties are improved. However, the fluorescent molecules based on indenofluorene tend to aggregate or form excimer associations, resulting in long-wave luminescence, thereby reducing the Device color purity and efficiency

Method used

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  • Electroluminescent monomer and polymer and preparation and application methods thereof
  • Electroluminescent monomer and polymer and preparation and application methods thereof
  • Electroluminescent monomer and polymer and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Embodiment 1: the preparation of polymerization monomer M1

[0076] Preparation of ethyl o-bromobenzoate: In a 500mL three-neck flask, dissolve o-bromobenzoic acid (20.1g, 0.1mol) in 200ml ethanol, and add 20ml of concentrated sulfuric acid dropwise to the reaction solution, and stir at room temperature for 12 hours , stop the reaction, quench the reaction with water, extract with dichloromethane and dry with anhydrous magnesium sulfate, obtain a yellow liquid after the solution is concentrated, purify by silica gel column chromatography, the mixed solvent of petroleum ether / dichloromethane (4 / 1 , v / v) was the eluent, and the yield was 87%. 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:

[0077]

[0078] Preparation of ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxabor-2-yl)ethyl benzoate: Under argon atmosphere, ethyl o-bromobenzoate T...

Embodiment 2

[0096] Example 2: Synthesis of Electroluminescent Polymer P1

[0097] Under argon atmosphere, 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene ( 321 mg, 0.50 mmol), 2,7-dibromo-9,9-dioctylfluorene (246.8 mg, 0.45 mmol) and 2,11-dibromo-13,13,14,14-tetrahexyl-13,14 -Dihydrodibenzo[c]indole[2,1-a]fluorene (M1) (39.9mg, 0.05mmol) was added to a 50ml two-neck flask, then 12ml of refined toluene was added, and then palladium acetate (2.80mg, 12.45 μmol) and tricyclohexylphosphine (6.98mg, 24.90μmol), then add 3ml tetraethylammonium hydroxide aqueous solution, raise the temperature to 80°C, and react for 24 hours; then add 20mg phenylboronic acid for capping, and after 12 hours, use 0.3ml of bromobenzene was capped; after continuing the reaction for 12 hours, stop the reaction, and when the temperature dropped to room temperature, the product was added dropwise in 300ml of methanol for precipitation, filtered, and then the crude product was dissolved in 20m...

Embodiment 3

[0101] Example 3: Synthesis of electroluminescent polymer P2

[0102] Under argon atmosphere, 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene ( 321 mg, 0.50 mmol), 2,7-dibromo-9,9-dioctylfluorene (219.4 mg, 0.40 mmol) and 2,11-dibromo-13,13,14,14-tetrahexyl-13,14 -Dihydrodibenzo[c]indole[2,1-a]fluorene (M1) (79.9mg, 0.10mmol) was added to a 50ml two-neck flask, then 12ml of refined toluene was added, and then palladium acetate (2.80mg, 12.45 μmol) and tricyclohexylphosphine (6.98mg, 24.90μmol), then add 3ml tetraethylammonium hydroxide aqueous solution, raise the temperature to 80°C, and react for 24 hours; then add 20mg phenylboronic acid for capping, and after 12 hours, use 0.3ml of bromobenzene was capped; after continuing the reaction for 12 hours, stop the reaction, and when the temperature dropped to room temperature, the product was added dropwise in 300ml of methanol for precipitation, filtered, and then the crude product was dissolved in 20m...

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Abstract

The invention belongs to the field of organic optoelectronics and discloses an electroluminescent monomer and polymer and preparation and application methods thereof. The structural formula of the electroluminescent polymer is shown as follows, which introduces a naphthalene nucleus on the structural basis of 10, 12-indane[2, 1-b] fluorene, accordingly, not only can the advantages of the 10, 12-indane[2, 1-b] fluorene which can effectively inhibit production of exciplexes and shortening of conjugated length to lead to movement of luminescent wavelength towards short wavelength and further to facilitate emission of purer blue light be retained, but also, by means of an asymmetric structure, the electroluminescent polymer can facilitate formation of amorphous film to inhibit fluorescence quenching. The electroluminescent polymer is high in dissolving property and applicable to processing solution, reducing device production costs as well as preparing large-area flexible OLED (organic light emitting diode) devices, and saves annealing treatment during production of electroluminescent devices, thereby being simple in production processes and having a huge potential and prospect for development in the field of organic electronic display.

Description

technical field [0001] The invention belongs to the field of organic optoelectronics, and in particular relates to an electroluminescence monomer, an electroluminescence polymer and a preparation method and application thereof. Background technique [0002] Organic light-emitting diode (OLED) displays use organic materials as light-emitting materials. The material structure is easy to modify and improve, and the selection range is wide; the driving voltage is low, only 3-12V DC voltage is required; self-illumination, no backlight is required; wide viewing angle , can be close to 180°; the response speed is fast, up to 1 μs; in addition, it has the advantages of light weight, ultra-thin, large size, flexible panel, and easy molding and processing. Due to the many advantages of OLED displays, it has attracted extensive attention from the scientific and industrial circles. Since Kodak Corporation of the United States developed OLED devices in 1987, many institutions have invest...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/54
CPCC08G61/121C08G2261/411C08G2261/5222C08G2261/124C08G2261/1412C08G2261/18C08G2261/1646C08G2261/312C08G2261/228C08G2261/95H10K85/624
Inventor 应磊胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司
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