Red light emitting fluorescent dye, synthesizing process and use thereof

A fluorescent dye and red light technology, applied in the field of fluorescent dye synthesis, can solve the problems of high price, low yield, complex synthesis method, etc., and achieve the effect of separation and purification

Inactive Publication Date: 2006-11-15
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This design idea avoids the active methyl group (C.H.Chen, C.W.Tang, J.Shi, K.P.Klubek, Macromol.Symp., 1997, 125, 49) participating in the reaction well, but the synthesis method is relatively complicated and requires a total of Carry out 5 steps reaction, and wherein the yield of first and second step is very low, is only 21%, 37% respectively; In addition, the raw material used in reaction is complex and expensive, especially the dimethylformide used in the second step Dimethylacetamide dimethyl acetal is expensive, which makes the cost of the product very high
In addition, when preparing electroluminescent devices, the doping concentration is only about 2%, which makes it difficult to ensure the repeatability of device preparation.
[0006] The DCM red light dyes involved in the above papers and patents still have some serious shortcomings, such as the absorption spectrum and the classical host material AlQ 3 Incomplete overlapping of emission spectra or poor electroluminescent color purity or serious concentration quenching effect or complex synthetic route, low yield and high cost

Method used

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  • Red light emitting fluorescent dye, synthesizing process and use thereof
  • Red light emitting fluorescent dye, synthesizing process and use thereof
  • Red light emitting fluorescent dye, synthesizing process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: Synthesis of asymmetric pyrones with the above P14 structure:

[0058]

[0059] Add 200ml of anhydrous ethylene glycol dimethyl ether in a 1000ml three-necked flask equipped with a constant pressure dropping funnel and an airway tube, protect with nitrogen, add 18 grams of sodium hydride (60%, 0.45mol), and heat Reflux, slowly add 100ml of ethylene glycol dimethyl ether solution of 0.15mol acetylacetone (1) dropwise under constant stirring, after 40 minutes after the addition is complete, heat and stir for 40 minutes, then add 0.15mol tert-butyl Quickly pour 100 ml of ethylene glycol dimethyl ether solution of methyl ethyl ester (2) into the reaction flask, the whole process should not exceed 2 minutes, and then reflux the reaction solution for 4 to 8 hours. Then evaporate most of the ethylene glycol dimethyl ether solvent under reduced pressure, add 150ml of ether to the obtained paste under ice-water cooling, stir for 10 minutes, and drop 200ml of cold w...

Embodiment 2

[0070] Embodiment 2: having the general formula M 1 Synthesis of the structure of Y1

[0071]

[0072] In a round bottom flask was added 4-(1,3-indanedione)-2-methyl-6-tert-butyl-pyran (structure A 1 ) 1mmol, N, N-bis-(4-formylphenyl) aniline (structure D 101 ) 1mmol, 30ml acetonitrile, 0.40ml hexahydropyridine, heated to reflux for 24 hours. Cool, filter the reaction solution, and wash the solid with ethanol for several times, and wash it with DMF / CHCl 3 The mixed solution was recrystallized to obtain product Y1 with a yield of 74%.

[0073] Elemental analysis Calculated value (C 38 h 31 NO 3 ): C, 83.03; H, 5.68; N, 2.55;

[0074] Measured value: C, 83.04; H, 5.68; N, 2.54;

[0075] Mass spectrometry (MS + ): 549 (M + )

Embodiment 3

[0076] Embodiment 3: having the general formula M 7 Synthesis of the structure of Y2

[0077]

[0078] In a round bottom flask was added 4-(1,3-indanedione)-2-methyl-6-tert-butyl-pyran (structure A 1 )1mmol, D 122 1.2mmol, 35ml acetonitrile, 0.50ml hexahydropyridine, heated to reflux for 24 hours. Aftertreatment method is the same as embodiment 2, product Y 2 , yield 74%.

[0079] Elemental analysis Calculated value (C 42 h 33 NO 3 ): C, 84.11; H, 5.55; N, 2.34;

[0080] Measured value: C, 84.10; H, 5.57; N, 2.35;

[0081] Mass spectrometry (MS + ): 599 (M + ).

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Abstract

The invention relates to the red beam luminescent dye which the receptor group is the 1, 3-indandione and the derivant 4H-pyrones. So the quenching effect of the new dyestuff has decreased efficiently and it has the saturated colour-purity. It can keep high efficient and the brightness in the high doping content. It is used for the organic photoconductor, the organic nonlinear optical material and the luminescent material of the electroluminescent cell. The emission band spectrum is in the red region of the visible spectrum and it has the high fluorescence quantum efficiency.

Description

technical field [0001] The invention belongs to the field of synthesis of fluorescent dyes, in particular to red light-emitting fluorescent dyes and their synthesis methods and applications. Background technique [0002] Luminescent dyes are the core part of organic electroluminescent devices (OLEDs). Realizing the luminescence of dyes in a specified wavelength range through molecular design is an important and hot research topic in the field of organic electroluminescence. Among the three primary colors of red, green, and blue necessary for full-color display, the practical standards for red light dyes are: current efficiency not less than 4cd / A; color coordinates reaching X=0.65 Y=0.35; device life reaching 10,000 Hours (initial brightness is 300cd / m under constant current drive 2 ). So far, almost no red light dye can meet all the above requirements. The low efficiency of red light devices is the weakest link in OLED commercialization. The doping dyes that are closer ...

Claims

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Application Information

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IPC IPC(8): C09K11/06H05B33/14
Inventor 王雪松姚宜山张宝文
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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