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2,6-diphenyl naphthalene derivative and preparation method and application thereof

A technology of diphenylnaphthalene and its derivatives, which is applied in the field of 2,6-diphenylnaphthalene derivatives and its preparation, can solve the problems of increasing the material cost budget and increasing the manufacturing cost of OLED devices, and achieve the improvement of external quantum efficiency, Effect of improving transmittance and enhancing luminous efficiency

Active Publication Date: 2016-11-09
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of an additional layer of CPL material not only needs to increase the cost budget of the material, but also needs to add a separate evaporation chamber, which increases the preparation cost of OLED devices.

Method used

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  • 2,6-diphenyl naphthalene derivative and preparation method and application thereof
  • 2,6-diphenyl naphthalene derivative and preparation method and application thereof
  • 2,6-diphenyl naphthalene derivative and preparation method and application thereof

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preparation example Construction

[0047] The present invention also provides a preparation method of the 2,6-diphenylnaphthalene derivative, comprising:

[0048] The compound shown in formula (A) and the compound shown in formula (B) are obtained the 2,6-diphenylnaphthalene derivative shown in formula (I) through coupling reaction under nitrogen protection:

[0049]

[0050] Among them, Ar is a C6-C60 aryl group, a C10-C60 fused aryl group, a C5-C60 six-membered heterocycle or a C4-C60 five-membered heterocycle, and X is a C6-C30 arylamino group or a C6-C30 of fused heterocycles.

[0051] According to the present invention, the intermediate shown in formula (A) is prepared according to the method shown below:

[0052] (1) 2,6-dichloronaphthalene shown in formula A-1 is reacted with elemental bromine to obtain a compound shown in formula A-2;

[0053] (2) reacting the compound represented by formula A-2 with Grignard reagent Ar-MgBr to obtain the intermediate represented by formula (A).

[0054]

[005...

Embodiment 1

[0063] Embodiment 1: the preparation of intermediate A

[0064]

[0065] (1) Synthesis of compound A-2: add 82ml fuming nitric acid (29%SO 3 ), followed by adding 11.0g (56mmol) of 2,6-dichloronaphthalene (compound A-1), 36g (225mmol) of Br 2 , 0.25g of Fe and 0.25g of I 2 , stirred vigorously at 60-70 °C for 6 hours. The mixed system was poured into ice water, filtered, and the solid was washed successively with aqueous sodium bisulfite, aqueous sodium bicarbonate and water. Recrystallization in toluene afforded 26.1 g (yield 91%) of compound A-2.

[0066] (2) Synthesis of intermediate A-a: Add 32ml of dry tetrahydrofuran and 5.8g (32mmol) of phenylmagnesium bromide successively to a dry 150ml three-necked flask, and dissolve 2.45g (4.0mmol) of compound A-2 in 20ml of dry in THF, in N 2 Added to the reaction system under the protection of , and stirred at room temperature for 12 hours. At 0°C, 6.35g (25mmol) of I 2 Added to the reaction system, stirred at room tempe...

Embodiment 2

[0070] Embodiment 2: the synthesis of compound TM1

[0071] Add 684mg (1mmol) of intermediate A-a and 231mg (0.2mmol) of tetrakis (triphenylphosphine) palladium mixture in 10ml of deaerated toluene, under N 2 Under protection, the system was heated to 60°C and stirred for 5 minutes. 636 mg (2.2 mmol) of triphenylamine-4-boronic acid, 2.5 ml of deaerated ethanol and 5 ml of deaerated 2M sodium carbonate aqueous solution were sequentially added to the system, and stirred at 80° C. for 21 hours. The reaction system was poured into a large amount of water and extracted with dichloromethane. The organic layer was washed successively with saturated brine and water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure. The residual solid was purified by column chromatography (hexane / dichloromethane=4:4, V / V), and recrystallized in a mixed solution of hexane / chloroform to obtain 597 mg (0.65 mmol) of compound TM1 with a yield of 65 %. Mass Spectrum m / z: 919...

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Abstract

The invention provides a 2,6-diphenyl naphthalene derivative and a preparation method and application thereof, and relates to the technical field of organic optoelectronic materials. The 2,6-diphenyl naphthalene derivative obtained by optimizing the molecular structure design has the higher optical extraction efficiency, can be used for preparing organic electroluminescence devices and especially can effectively improve the optical emitting efficiency of OLED devices by serving as an optical extraction material of the organic electroluminescence devices, and the OLED devices are superior to existing commonly-used OLED devices. The invention further provides the preparation method of the 2,6-diphenyl naphthalene derivative. The preparation method is simple, and the raw materials are easy to obtain.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a 2,6-diphenylnaphthalene derivative and a preparation method and application thereof. Background technique [0002] Organic electroluminescence display (organic electroluminescence display) technology is known as a flat display technology with fantastic display characteristics, because its light-emitting mechanism is similar to that of light-emitting diodes (LEDs), so it is also called OLED (organic light emitting diode). Since 2000, OLED has received great attention from the industry and has begun to enter the stage of industrialization. [0003] After decades of development, OLED has come a long way. Although its internal quantum efficiency is close to 100%, its external quantum efficiency is only about 20%. Most of the light is confined inside the light-emitting device due to factors such as substrate mode loss, surface plasmon loss, and waveguide ef...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C211/54C07C211/58C07C211/61C07C213/08C07C217/92C07D209/86C07D335/02C07D409/14H01L51/54
CPCC07C211/54C07C211/58C07C211/61C07C217/92C07D209/86C07D335/02C07D409/14H10K85/655H10K85/633H10K85/631H10K85/6572
Inventor 周雯庭郭建华
Owner CHANGCHUN HYPERIONS TECH CO LTD
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