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A kind of 2,5-dinaphthyl oxane derivative and preparation method thereof

A technology of naphthyloxane and derivatives, applied in the field of new charge transport materials, can solve the problems affecting the luminous efficiency and life of the device, easy crystallization, etc., achieve strong conjugation, increase glass transition temperature, and high fluorescence quantum efficiency Effect

Active Publication Date: 2016-08-24
山东盛华电子新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, because its glass transition temperature Tg is only 60°C, it is easy to crystallize, which seriously affects the luminous efficiency and life of the device.
Therefore, its performance needs to be improved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1, a 2,5-dinaphthyloxane derivative, the structural formula of the derivative is as follows:

[0028] , where R=R` or R≠R`, R and R` are hydrogen atoms, ethyl or propylalkyl groups;

[0029] The above-mentioned derivative in this embodiment is 2,5-dinaphthyl-1,3-oxane, and its structural formula is as follows:

[0030] ;

[0031] Its preparation method is: add 2-naphthyl-1,3 propanediol 30g, 4-p-propylphenyl naphthyl formaldehyde 23g, silicon-based Solid acid catalyst (p-toluenesulfonic acid supported on diatomite) 3g, toluene 110ml, placed under ultrasonic conditions, began to stir and heat, reacted at 80-90°C for 1h, sampled and analyzed, determined that the reaction was terminated according to the gas phase analysis results, cooled, Filter, then add 50ml of water to the filtrate, separate the liquids, extract the water phase with 20ml of toluene, combine the organic phases, wash with water until neutral, dry with 5g of anhydrous magnesium sulfate for 4h...

Embodiment 2

[0039] Embodiment 2, a 2,5-dinaphthyloxane derivative, the derivative is 2,5-di(4-ethyl)naphthyl-1,3-dioxane, and its structural formula is:

[0040] ;

[0041] The preparation method is as follows: add 2-(4-ethyl-1-naphthyl)-1, 30 g of 3-propanediol, 4-ethylnaphthalene to a 250 ml three-necked reaction flask equipped with mechanical stirring, reflux condenser, and addition funnel. 23g of methyl formaldehyde, 3g of silicon-based solid acid catalyst (p-toluenesulfonic acid supported on diatomite), 110ml of DMF, placed under ultrasonic conditions, began to stir and heat, reacted at 90-110°C for 1h, sampled and analyzed, according to the results of gas phase analysis Determine the termination of the reaction, cool, filter, then add 500ml of water to the filtrate, rinse with 100ml of water after filtration, until neutral, dry for 4h, take a sample and analyze to determine the quality of the crude product ω: 75%, recrystallize, filter, and purify, the mother liquor Recycled, 37....

Embodiment 3

[0049] Embodiment 3, a 2,5-dinaphthyloxane derivative, the derivative is 2,5-di(4-propyl)naphthyl-1,3-dioxane, and its structural formula is:

[0050] ;

[0051] Its preparation method is: add 2-(4-propyl-1-naphthyl)-1, 30g of 3-propanediol, 4-propylnaphthalene to the 250ml three-neck reaction flask that is equipped with mechanical stirring, reflux condenser, and addition funnel successively 23g of methyl formaldehyde, 3g of silicon-based solid acid catalyst (p-toluenesulfonic acid supported on diatomite), 150ml of DMF, placed under ultrasonic conditions, began to stir and heat, reacted at 90-130°C for 1h, sampled and analyzed, according to the results of gas phase analysis Determine the termination of the reaction, cool, filter, then add 800ml of water to the filtrate, rinse with 100ml of water after filtration, until neutral, dry for 4h, take a sample and analyze to determine the quality of the crude product ω: 77%, recrystallize, filter, and purify, the mother liquor Rec...

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Abstract

The invention discloses a 2,5-dinaphthyloxane derivative, which is characterized in that the structural formula of the derivative is as follows: where R=R` or R≠R`, R and R` are hydrogen atoms, ethyl groups or Propylalkyl group is 4-substituted-1-naphthyl formaldehyde and 2-(4-substituted)naphthyl-1,3-propanediol, dissolved in DMF or toluene at a ratio of 1mol:0.8~2.0mol In such organic solvents as catalyzed by a silicon-based solid acid catalyst, react at 40-150°C for 0.5-2.0h under ultrasonic radiation to obtain 2,5-dinaphthyloxane derivatives. The present invention has high fluorescence quantum efficiency, It is not suitable for crystallization and has the characteristics of simple preparation method.

Description

technical field [0001] The invention belongs to the technical field of organic charge transport materials, and in particular relates to a new charge transport material and a synthesis method thereof. technical background [0002] OLED display technology has been gradually applied in daily life. Organic charge transport material is its core material. Organic charge transport material is a kind of carrier (electron or hole) injection, under the action of electric field, it can realize the The directional and orderly movement of flow carriers, thereby carrying out the organic semiconductor material of charge transport. The material is further divided into hole transport materials and electron transport materials. [0003] Most of the current research and application are hole transport materials. Due to the difficulty in preparation and characterization of electron transport materials, there are not many related research reports, which makes the research of electron transport ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/06C09K11/06H01L51/54
CPCC09K11/06C07D319/06C09K2211/1018H10K85/653
Inventor 王哲王作鹏武生喜盛丽杜开昌王永峰
Owner 山东盛华电子新材料有限公司
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