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Star-shaped tetraaryl ethylene compounds and preparation method and application thereof

A technology of tetraarylethylene and compound, applied in the field of organic light-emitting materials, can solve the problems of weak light absorption ability, low thermal stability of compound, and difficulty in meeting device requirements, etc.

Active Publication Date: 2013-06-26
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing tetraphenylethylene derivatives have the following two problems: (1) only one or two tetraphenylethylene functional groups are contained in the compound molecule, and the light absorption ability is weak; (2) the thermal stability of this type of compound The performance is not high, it is difficult to meet the device requirements

Method used

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  • Star-shaped tetraaryl ethylene compounds and preparation method and application thereof
  • Star-shaped tetraaryl ethylene compounds and preparation method and application thereof
  • Star-shaped tetraaryl ethylene compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of 1-(4-bromophenyl)-1,2,2-triphenylethylene (TPE-Br)

[0054]

[0055] Add 2.02g (12mmol) of diphenylmethane and 20mL of dry tetrahydrofuran into a 50mL Schlenk reaction flask, and place the system in a low-temperature bath at -78°C after removing water and oxygen, and add 4.55mL of 2.2M (10mmol) The butyllithium solution was slowly added dropwise to the system, kept at -78°C, and reacted for 2 hours. Then 2.18g (9mmol) of 4-bromodiphenyl ketone was dissolved in a small amount of dry tetrahydrofuran, and this solution was injected into the reaction system (maintained at -78°C), and then the reaction system was slowly raised to room temperature for 12 hours of reaction. After the reaction, pour the reaction solution into water to terminate the reaction, extract the reaction solution three times with dichloromethane, combine the organic phases, wash with saturated ammonium chloride, saturated saline, water three times, and anhydrous Na 2 SO 4 Dry and spi...

Embodiment 2

[0058] Preparation of 4-(1,2,2-triphenylethenyl)phenylboronic acid (TPE-B(OH) 2 )

[0059]

[0060] Add 1.67g (4.0mmol) TPE-Br into a 100mL Schlenk reaction flask, repeat vacuuming-nitrogen three times, and add 40mL THF under nitrogen atmosphere. The reaction flask was placed in a low-temperature bath (-78°C), and 3.2mL of 2.5M (0.8mmol) n-butyllithium was carefully added dropwise with a syringe, and the reaction was stirred at -78°C for 3h. Then 2.4 mL (22.1 mmol) of trimethyl borate in THF were added at -78°C. The reaction system was raised to room temperature and stirred for 12 h, and the reaction was terminated with 10 mL of 2M HCl. The reaction solution was poured into water, with CH 2 Cl 2 The aqueous phase was extracted several times, and the organic phases were combined, washed with saturated brine and water three times respectively, and anhydrous Na 2 SO 4 After drying, the solvent was spin-dried and separated by a chromatographic column (200-300 mesh silica ...

Embodiment 3

[0062] Preparation of 1,2-bis(4'-(1,2,2-triphenylethenyl)-[1,1'-biphenyl]-4-yl)acetylene

[0063]

[0064] Add 376mg (1.0mmol) TPE-B(OH) to a 150mL Schlenk reaction flask 2 , 134mg (0.4mmol) bis(4-bromophenyl) acetylene and 20mg (0.017mmol) tetrakistriphenylphosphine palladium, repeat vacuuming-nitrogen operation three times, add 50mL THF and 3mL 2M sodium carbonate under nitrogen atmosphere aqueous solution, stirred and refluxed overnight. The reaction solution was poured into water, the aqueous phase was extracted several times with dichloromethane, the organic phases were combined, washed with saturated saline and water three times respectively, and washed with anhydrous Na 2 SO 4 Dry, spin to dry the solvent, and use petroleum ether / dichloromethane as the eluent to separate on a chromatographic column (200-300 mesh silica gel) to obtain 250 mg of a white solid with a yield of 74.5%. 1 HNMR (400MHz, CDCl 3 ), d (ppm): 7.89 (d, 2H, J=8.0Hz), 7.13-7.01 (m, 17H), 4.49 (...

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Abstract

The invention discloses star-shaped tetraaryl ethylene compounds. In the invention, the star-shaped tetraaryl ethylene compounds with rigid frameworks are synthesized through molecular design, each compound molecule contains one or more tetraaryl ethylene groups, and the compounds have special luminescent properties, namely the properties that the compounds almost have no fluorescence in dilute solution and fluorescence is greatly enhanced in an aggregation state or solid state. The invention also discloses a preparation method for the star-shaped tetraaryl ethylene compounds. The compounds have higher decomposition temperature and high thermal stability, and can be used as organic fluorescent materials which are applied to devices. The structural general formula of the compounds is shownin the specification, wherein X and Y are positive integers and the sum of X and Y is equal to 6.

Description

technical field [0001] The present invention relates to tetraarylethene compounds, their preparation method and their use in organic luminescent materials, and belong to the technical field of organic luminescent materials; in particular, they relate to star-shaped tetraarylethene compounds and their preparation methods and use. Background technique [0002] Traditional organic light-emitting molecules only have high fluorescence quantum yields in dilute solutions, and the fluorescence is greatly reduced or even disappeared at high concentrations or in solid states, that is, the concentration quenching effect. In the preparation of organic electroluminescent devices, light-emitting materials are usually made into thin films, so fluorescence quenching is unavoidable on light-emitting materials. In order to avoid fluorescence quenching, light-emitting molecules are usually doped into the polymer material with carrier effect at a low concentration, generally the doping concent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/54C07C15/52C07C1/32C07C25/24C07C17/281C07C43/215C07C43/285C07C41/30C09K11/06
Inventor 李嫕唐海云曾毅陈金平李迎迎
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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