Aggregation-induced light emitting material simultaneously containing triphenylethylene structure and tetraphenylethylene structure and synthesis method and application thereof

A technology of aggregation-induced luminescence and tetraphenylethylene, applied in the direction of luminescent materials, chemical instruments and methods, hydrocarbons, etc., can solve the problems of aggregation fluorescence quenching, etc., and achieve the effect of easy purification, high thermal stability, and high luminous intensity

Active Publication Date: 2010-12-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, as the light-emitting materials used in organic light-emitting devices, they must be used in the state of solid thin films. Therefore, with the formation of solid thin films, the aggregation fluorescence quenching phenomenon will inevitably occur, which seems to be a difficult problem to solve.

Method used

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  • Aggregation-induced light emitting material simultaneously containing triphenylethylene structure and tetraphenylethylene structure and synthesis method and application thereof
  • Aggregation-induced light emitting material simultaneously containing triphenylethylene structure and tetraphenylethylene structure and synthesis method and application thereof
  • Aggregation-induced light emitting material simultaneously containing triphenylethylene structure and tetraphenylethylene structure and synthesis method and application thereof

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preparation example Construction

[0021] The synthesis method of above-mentioned luminescent material, comprises the following steps:

[0022] Step 1: Synthesis of triphenylethylene intermediates with functional groups

[0023] The synthesis of triphenylethylene intermediates with functional groups adopts the reaction of benzophenone and its halogenated products with halogenated phenylphosphonate ylide reagents to form halogenated triphenylethylene intermediates. Preferred benzophenone raw material of the present invention is 4,4'-dibromobenzophenone, 4-bromobenzophenone and benzophenone; Preferred ylide reagent is 4-bromobenzylidene phosphonic acid diethyl ester. The preparation process for synthesizing the triphenylethylene intermediate from the above preferred raw materials is simple and the yield is high, which is one of the main features of the present invention. For the synthesis of substituents, conventional organic synthesis methods are used, including Friedel-Crafts alkylation, amine alkylation, halo...

Embodiment 1

[0036] Triphenylethylene-tetraphenylethylene [VP 3 -(TPE) 1 ]Synthesis:

[0037] (1) Bromotriphenylethylene (VP 3 -Br) synthesis

[0038] Dissolve benzophenone (13.59g, 74.6mmol) and diethyl 4-bromobenzylidene phosphonate (27.49g, 89.5mmol) in 250mL THF, add potassium tert-butoxide (10.01g, 89.5mmol) , Stir the reaction at room temperature under the protection of argon for 4h. The solvent was evaporated under reduced pressure, the sample was purified by silica gel column chromatography, and the eluent was n-hexane to obtain 23.20 g of white crystals with a yield of 93%.

[0039]

[0040] (2) Synthesis of brominated tetraphenylethylene (TPE-Br):

[0041]Dissolve diphenylmethane (4.00g, 23.8mmol) in 50mL tetrahydrofuran, stir for 30min at 0°C under argon protection, slowly drop into 2.2M n-hexane solution of n-butyllithium (13.0mL, 28.6mmol), stir Reaction 1h. Then 4-bromobenzophenone (4.97g, 19.0mmol) was added, the temperature was slowly raised to room temperature, a...

Embodiment 2

[0050] Triphenylethylene-bis(tetraphenylethylene)[VP 3 -(TPE) 2 ]Synthesis:

[0051] (1) Dibromotriphenylethylene (VP 3 -Br 2 )Synthesis:

[0052] Dissolve 4,4'-dibromobenzophenone (2.00g, 5.8mmol) and diethyl benzylidene phosphonate (1.98g, 8.7mmol) in 40mL tetrahydrofuran, add potassium tert-butoxide (0.98g , 8.7mmol), and stirred at room temperature for 4h under the protection of argon. The solvent was evaporated under reduced pressure, and the sample was purified by column chromatography using n-hexane as the mobile phase and silica gel as the stationary phase to obtain 2.10 g of white crystals with a yield of 88%.

[0053]

[0054] (2) Triphenylethylene - two (tetraphenylethylene) [VP 3 -(TPE) 2 ]Synthesis:

[0055] put VP 3 -Br 2 (0.22g, 0.53mmol) and TPEB (0.48g, 1.3mmol) were dissolved in 30mL of toluene, 2M potassium carbonate aqueous solution (0.7mL) and 5 drops of Aliquat336 were added, and after argon flow for 40min, a catalytic amount of Pd(PPh 3 ) ...

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Abstract

The invention belongs to the technical field of organic light emitting materials, and discloses an aggregation-induced light emitting material simultaneously containing a triphenylethylene structure and a tetraphenylethylene structure. During synthesis, a triphenylethylene intermediate containing a functional group and a tetraphenylethylene intermediate containing a functional group are connected together by coupling reaction. A synthesis method of the invention has the advantages of simple process and convenient purification; and the synthesized organic light emitting material simultaneously containing the triphenylethylene structure and the tetraphenylethylene structure has the advantages of obvious aggregation-induced light emitting performance, high thermal stability, high glass-transition temperature and high luminous intensity and is suitable for preparing a light emitting layer material in an organic electroluminescent material device.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, in particular to an aggregation-induced luminescent material containing both triphenylethylene and tetraphenylethylene structures, a synthesis method and application thereof. Background technique [0002] Due to their huge potential applications in flexible display and lighting, organic light-emitting devices such as organic light-emitting diodes (OLEDs) have been highly valued by the scientific and industrial circles in recent years, and are one of the current research and development hotspots. [0003] Organic light-emitting materials play a pivotal role in the technology of organic light-emitting devices, which directly affect the luminous efficiency and service life of light-emitting devices. Most organic light-emitting materials have high fluorescence quantum yields in the dilute solution state, but become weakly fluorescent or do not emit light at all in the solid stat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C15/52C07C1/32C07C1/34H01L51/54
Inventor 池振国许炳佳黎小芳李海银张锡奇王程程周炜张艺刘四委许家瑞
Owner SUN YAT SEN UNIV
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