Organic luminescent material phenylene ethynylene dimmer, synthesizing method and use

A technology of phenylene acetylene and synthesis method, which is applied in the direction of light-emitting materials, silicon organic compounds, chemical instruments and methods, etc., and can solve the problems of limited research on the types, properties and photoelectric properties of alkyl substituents

Inactive Publication Date: 2009-07-22
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although there have been previous studies on the synthesis of DPEs, the research on the types, properties and photoelectric properties of the alkyl substituents in the DPEs structure is quite limited.

Method used

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  • Organic luminescent material phenylene ethynylene dimmer, synthesizing method and use
  • Organic luminescent material phenylene ethynylene dimmer, synthesizing method and use
  • Organic luminescent material phenylene ethynylene dimmer, synthesizing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: 4-(2-methyl-4-trimethylsilylethynyl phenylethynyl) phenyl thioacetate ( 1a )Synthesis

[0052] Add 1.89 g (6.0 mmol) of 2-methyl-4-trimethylsilylethynyl iodobenzene, 0.21 g (0.30 mmol) of bistriphenylphosphine palladium dichloride, and 0.057 g (0.30 mmol) of copper iodide into a 100 mL four-necked flask. g (0.30mmol), 4.48g (10.8mmol) of tri-n-butylamine and 30mL tetrahydrofuran, stirred at room temperature for 0.5h under nitrogen protection, then added 1.16g (6.6mmol) of p-thioacetylphenylacetylene, and continued the reaction for 24h before adding The reaction was quenched with 50 mL of water. Dichloromethane (30mL × 3) was extracted, the organic layer was washed with saturated NaCl solution, anhydrous MgSO 4 Dry, evaporate the solvent under reduced pressure to obtain a dark brown solid, which is separated and purified by column chromatography (silica gel filling, n-hexane / ethyl acetate) to obtain a light yellow solid 4-(2-methyl-4-trimethylsilylethynyl...

Embodiment 2

[0053] Embodiment 2: 4-(2-ethyl-4-trimethylsilylethynyl phenylethynyl) phenyl thioacetate ( 1b )Synthesis

[0054] Add 1.97 g (6.0 mmol) of 2-ethyl-4-trimethylsilylethynyl iodobenzene, 0.21 g (0.30 mmol) of bistriphenylphosphine palladium dichloride, and 0.057 g (0.30 mmol) of copper iodide into a 100 mL four-neck flask. g (0.30mmol), 4.48g (10.8mmol) of tri-n-butylamine and 30mL tetrahydrofuran, stirred at room temperature for 0.5h under nitrogen protection, then added 1.16g (6.6mmol) of p-thioacetylphenylacetylene, and continued the reaction for 24h before adding The reaction was quenched with 50 mL of water. Dichloromethane (30mL × 3) was extracted, the organic layer was washed with saturated NaCl solution, anhydrous MgSO 4 Dry, evaporate the solvent under reduced pressure to obtain a black solid, which is separated and purified by column chromatography (silica gel filling, n-hexane / ethyl acetate) to obtain a light yellow solid 4-(2-ethyl-4-trimethylsilylethynyl- Phenyle...

Embodiment 3

[0055] Embodiment 3: 4-(2,6-dimethyl-4-trimethylsilylethynyl phenylethynyl) phenyl thioacetate ( 1c )Synthesis

[0056] Add 1.97g (6.0mmol) of 2,6-dimethyl-4-trimethylsilylethynyl iodobenzene into a 100mL four-neck flask, 0.21g (0.30mmol) of bistriphenylphosphine palladium dichloride, and iodide Cuprous 0.057g (0.30mmol), tri-n-butylamine 4.48g (10.8mmol) and 30mL tetrahydrofuran, stirred at room temperature for 0.5h under nitrogen protection, then added 1.16g (6.6mmol) of p-thioacetylphenylacetylene, and continued the reaction After 30 h, 50 mL of water was added to quench the reaction. Dichloromethane (30mL × 3) was extracted, the organic layer was washed with saturated NaCl solution, anhydrous MgSO 4 Dry, and evaporate the solvent under reduced pressure to obtain a black solid, which is separated and purified by column chromatography (filling with silica gel, n-hexane / ethyl acetate) to obtain a light yellow solid 4-(2,6-dimethyl-4-trimethylsilane Ethynyl-phenylethynyl)ph...

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Abstract

The invention provides a 2-polyphenylene ethynylene luminescent material of organic molecules as well as a preparation method and an application thereof; the preparation method comprises the steps that: paratrimethyl silicane acetylene iodobenzene substituted by short chain alkyls is taken as a raw material; the paratrimethyl silicane acetylene iodobenzene substituted by short chain alkyls, and para ethanethioyl phenylacetylene conduct a Sonogashira coupling reaction in tetrahydrofuran for 20 hours to 50 hours with 2-(triphenylphosphine) palladium chloride/cuprous iodide as a catalyst and under the action of tri-n-butylamine to obtain phenylene ethynylene dipolymer series; the phenylene ethynylene dipolymer series can be applied to the luminescent layer or the electron transport layer of the organic LED.

Description

technical field [0001] The invention relates to a phenylene acetylene dimer [Dimeric(phenylene ethylene)s, DPEs], a synthesis method and application. Especially with regard to the flexible alkyl substituent at the side chain position, the compound can be used as an organic light-emitting material for the light-emitting layer or electron transport layer in an organic light-emitting diode device. technical background [0002] Organic light-emitting diode display device (Organic light-emitting diode, OLED) will become a new generation of light source and flat panel due to its many excellent advantages such as rich colors, active light emission, small size, thin thickness, wide viewing angle, low energy consumption and fast response speed. A strong contender for the display. Since it was first reported in 1987 [1] Therefore, the research and development of organic light-emitting materials with high fluorescence yield and good stability has become one of the hot spots of scient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C09K11/06H01L51/50H01L51/54
Inventor 朱红军刘睿常进李玉峰罗维李钰皓刘山
Owner NANJING UNIV OF TECH
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