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Derivative of 8-hydroxyquinoline of emitting red light

A technology of hydroxyquinoline and derivatives, which is applied in the field of 8-hydroxyquinoline derivatives containing dicyanomethylisophorone, which can solve the problems that the luminous performance of the device is greatly affected, and the luminous chromaticity and brightness are difficult to balance. , to achieve the effect of improving electron transport performance and reducing LUMO orbital

Inactive Publication Date: 2005-10-26
INESA ELECTRON +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the two dyes, DCM and DCJTB, have a planar structure, they are easy to form an aggregated state, and have a very obvious self-quenching phenomenon caused by the doping concentration, which has a great impact on the luminous performance of the device, and it is difficult to balance the luminous chromaticity and brightness.

Method used

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  • Derivative of 8-hydroxyquinoline of emitting red light
  • Derivative of 8-hydroxyquinoline of emitting red light
  • Derivative of 8-hydroxyquinoline of emitting red light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of compound I-1:

[0022]

[0023] In the flask, add 0.346 gram of 5-formyl-8-hydroxyquinoline (2mmol), 0.372 gram of 2-(3,5,5-trimethylcyclohexene-2-ylidene) malononitrile (2mmol) , 5ml of freshly treated anhydrous acetonitrile and 2 drops of piperidine. Under the protection of argon, the reaction mixture was refluxed for 20h. After the reactant was cooled to room temperature, a dark red precipitate precipitated, which was filtered and washed with 10 ml of acetonitrile. After drying, 0.612 g of dark red powder was obtained, with a yield of 92.8%.

[0024] m.p.253~255℃.

[0025] 1 H NMR (500MHz, CDCl 3 , ppm): δ8.91(d, J=3.5Hz, 1H), 8.66(d, J=7.5Hz, 1H), 7.91(d, J=6.2Hz, 1H), 7.68(s, 1H), 7.65 (t, J=5.5Hz, 1H), 7.40(m, 1H), 7.05(d, 1H), 6.9(s, 1H), 2.64(s, 2H), 2.57(s, 2H), 1.13(s, 6H).

[0026] The maximum absorption wavelength in tetrahydrofuran is 437nm (logε=4.25), the maximum emission wavelength is 603nm, and it is orange-red fluorescence.

Embodiment 2

[0028] Synthesis of Compound 1-2:

[0029]

[0030] (1) Synthesis of (E)-2-(3-(4-nitrostyryl)-5,5-dimethylcyclohex-2-enyl) malononitrile (compound A):

[0031] In the flask, add 0.66 g of p-nitrobenzaldehyde (4.4 mmol), 0.81 g of 2-(3,5,5-trimethylcyclohexene-2-ylidene) malononitrile (4.4 mmol), 5 ml of new Treat with anhydrous acetonitrile and 2 drops of piperidine. Under the protection of argon, it was refluxed for 2h. After the reactant was cooled to room temperature, a tan precipitate precipitated, which was filtered and washed with 10 ml of acetonitrile. After drying, 1.05 g of brown yellow powder of compound A was obtained, with a yield of 72.0%.

[0032] (2) Synthesis of (E)-2-(3-(4-aminostyryl)-5,5-dimethylcyclohex-2-enyl)malononitrile (compound B):

[0033] In a flask, 1.05 g of compound A (3.3 mmol), 3.70 g of stannous dichloride dihydrate (16.4 mmol), 20 ml of ethanol and 2 drops of glacial acetic acid were added. Under the protection of argon, it was reflux...

Embodiment 3

[0040] Synthesis of Compound I-3

[0041]

[0042]

[0043] (1) References for the preparation of 8-hydroxy-2-methylquinoline-5-sulfonyl chloride (J.A.C.S.2001, 123, 5160), references for the synthesis of p-piperazinyl benzaldehyde (Dyes and Pigments 2003, 59, 143 ).

[0044] (2) Synthesis of Compound C

[0045] In the flask, add 0.19 g of p-piperazinyl benzaldehyde (1.0 mmol), 0.20 g of potassium carbonate (1.5 mmol) and 20 ml of dichloromethane, after stirring for 20 min, add 0.26 g of 8-hydroxyl-2-methylquine in batches Phenyl-5-sulfonyl chloride (1.0 mmol), stirred at room temperature for 4h. Pour into 50ml of water, extract with dichloromethane, and dry the organic phase with anhydrous sodium sulfate. After rotary evaporation, a tan powder was obtained, which was passed through a silica gel column with a developing solvent of chloroform / methanol (4:1). Collect the first component, 0.32 g of light-colored powder after rotary evaporation. Yield 77.8%.

[0046] (...

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Abstract

The present invention relates to a 8-hydroxyquinoline derivative containing dicyanomethylisophorous. Said invention is characterized by adopting the following steps: chemically modifying 8-hydroxyquinoline, introducing the structure containing dicyanomethylisophorone and utilizing the group capable of forming conjugated system or the group capable of introducing N atoms as donor group to form conjugated system with D-pi-A structure to form connection between two functional gruops of hydroxyquinolnie and dicyanomethylisopho-rone. The dicyan and 8-hydroxyquinoline metal complex in said compound can effectively reduce molecular LUMO track, raise electronic transmission performance of material, so that it is a n-type semiconductor material emitting red light.

Description

technical field [0001] The present invention relates to a kind of 8-hydroxyquinoline derivative, in particular to a kind of 8-hydroxyquinoline derivative containing dicyanomethyl isophorone. Background technique [0002] With the development of multimedia technology, the performance requirements of flat panel displays are getting higher and higher. Organic electroluminescent devices (OLEDs) have the advantages of low-voltage DC drive, active light emission, large vision, fast response, rich colors, and low cost, and are recognized as the most ideal and most promising next-generation display technology. Since 2000, there has been an upsurge in OLED research and development around the world. Prototype samples and products have been launched continuously, with an average annual growth rate of more than 100%. In 2003, the world OLED sales revenue reached 263 million US dollars, an increase of 127% over the previous year. Display Search predicts that from now to 2008, the world'...

Claims

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Application Information

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IPC IPC(8): C07D215/26
Inventor 田禾金松卜东生谢军涛孟凡顺苏建华余峰
Owner INESA ELECTRON
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