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Aryl substituted pyrimidine spirobifluorene derivative and preparation thereof

A technology of pyrimidine spirobifluorene and aryl pyrimidine, which is applied in the field of aryl-substituted pyrimidine spirobifluorene derivatives and their preparation, can solve the problems of not being developed, achieve novel molecular structure, good thermal stability, and improve optical purity Effect

Inactive Publication Date: 2009-01-28
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, a single aromatic pyrimidine-substituted spirobifluorene derivative for organic electroluminescent materials has not been developed based on the characteristics of these two types of compounds, spirobifluorene and 2-aminopyrimidine.

Method used

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  • Aryl substituted pyrimidine spirobifluorene derivative and preparation thereof
  • Aryl substituted pyrimidine spirobifluorene derivative and preparation thereof
  • Aryl substituted pyrimidine spirobifluorene derivative and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Preparation of spirobifluorene

[0022] Add 1.26g of magnesium to a flask containing 10ml of ether, and slowly add a solution of 2-bromobiphenyl (11.65g, 50.0mmol) in 20ml of ether under the trigger of 1,2-dibromoethane, and reflux for 3 hours , to make the Grignard reagent. The prepared Grignard reagent was slowly added to a 40ml solution of 9-fluorenone (9.9g, 55mmol), and refluxed for 3 hours. The resulting yellow magnesium complex was collected by suction filtration, washed with dry ether, and the solid was stirred in ice-cold saturated ammonium chloride solution. After 2 hours, the solid was collected, filtered and dried, dissolved in hot acetic acid, and added dropwise Concentrate hydrochloric acid until the generated solids no longer increase, filter, and recrystallize from ethanol to obtain 14.0 g of spirobifluorene in colorless flaky crystals, with a yield of about 88.7%. m.p.207~208℃; 1 HNMR (CDCl 3 , 500MHz) δ: 6.75(d, J=7Hz, 1H, Ar-H), 7.13(t, J=8Hz,...

Embodiment 2

[0040] (1) Preparation of spirobifluorene

[0041] Same as Example 1

[0042] (2) Preparation of 2-acetylspirobifluorene

[0043] Same as Example 1

[0044] (3) preparation of chalcone

[0045] Add 2-acetyl spirobifluorene (1.58g, 5mmol) and 1-naphthaldehyde (0.80g, 5.1mmol) and tetrahydrofuran and ethanol in the volume ratio of 4: 1 mixed solvent 100ml, and then add 10ml of 30% sodium hydroxide solution was stirred at room temperature for 12 hours, acidified to neutrality with 2N hydrochloric acid, extracted with dichloromethane (3×20ml), then dried with anhydrous magnesium sulfate, spin-dried and washed with ethanol After recrystallization, 1.99 g of chalcone as a pale yellow solid was obtained with a yield of about 80%.

[0046] Physical constants and spectral data of the product:

[0047] Product appearance: pale yellow solid, melting point: 237-239°C, 1 HNMR (CDCl 3 , 500MHz) δ: 6.77(tJ=8Hz3H), 7.14(t, J=8Hz, 2H), 7.20(t, J=8Hz, 2H), 7.50(m, 6H), 7.56(q, 2H), 7.81(...

Embodiment 3

[0055] (1) Preparation of spirobifluorene

[0056] Same as Example 1

[0057] (2) Preparation of 2-acetylspirobifluorene

[0058] Same as Example 1

[0059] (3) preparation of chalcone

[0060] Add 2-acetylspirobifluorene (1.58g, 5mmol) and p-chlorobenzaldehyde (0.72g, 5.1mmol) and tetrahydrofuran and ethanol into the flask in a volume ratio of 4: 1 mixed solvent 100ml, and then add 10ml of 30% sodium hydroxide solution was stirred at room temperature for 12 hours, acidified to neutrality with 2N hydrochloric acid, extracted with dichloromethane (3×20ml), then dried with anhydrous magnesium sulfate, spin-dried and washed with ethanol After recrystallization, 2.07 g of chalcone in colorless flaky crystals was obtained with a yield of about 86%.

[0061] Physical constants and spectral data of the product:

[0062]Product appearance: colorless flaky crystal, melting point: 190~192℃; 1 HNMR (CDCl 3 , 500MHz) δ: 6.76(m, 3H), 7.13(t, J=8Hz, 2H), 7.19(t, J=8Hz, 1H), 7.34(q, 3...

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Abstract

The invention discloses an aryl substituted pyrimidine spirobifluorene derivative which is characterized in that aryl pyrimidine is linked with the spirobifluorene, an aromatic substituted pyrimidine group is introduced at the place of 2 of the spirobifluorene, and the substituted aryls are a phenyl group, naphthyl, parachlorobenzyl, p-methoxy phenyl, thienyl and furyl. A preparation method thereof comprises the following steps: the spirobifluorene and acetyl chloride are synthesized into monoacetyl spirobifluorene by acylation reaction, the monoacetyl spirobifluorene and the aryl are synthesized into chalcone by condensation reaction, and then the chalcone and guanidine nitrate are prepared into the aryl substituted pyrimidine spirobifluorene derivative by ring closing reaction. When being used in organic electroluminesent materials, the aryl substituted pyrimidine spirobifluorene derivative has the advantages of good thermal stability, a relatively smooth acromion-free emission peak, easily obtaining pure color electroluminescence, being favorable for an organic light-emitting diode (OLED) to adjust emitting light colors, and effectively improving optical purity, luminescent efficiency and service life. The derivative has simple synthesis process and high yield. The aryl substituted pyrimidine spirobifluorene derivative is a novel material presently used for producing big screens and soft screens with high-brightness and high-definition.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials and their synthesis, in particular to an aryl-substituted pyrimidine spirobifluorene derivative and a preparation method thereof. Background technique [0002] Since the 1980s, the research on organic electroluminescent (OLED) materials has developed rapidly. OLED has the characteristics of low starting voltage, good stability, high efficiency, long life and good moldability, so it is used in lighting, instruments , Instrument display and other fields have a wide range of applications. Moreover, OLED is currently the only new material that can be used to produce large-screen, high-brightness, high-definition soft-screen full-band display. It has huge commercial value and is expected to become a pillar industry of the country. [0003] In organic electroluminescent materials, there are many electronic systems such as tetrahedral molecules, dendritic molecules, and spir...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07D407/04C07D409/04C09K11/06
Inventor 刘乾才史英博
Owner EAST CHINA NORMAL UNIVERSITY
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