Light conversion film for green dye containing agglomeration-induced emission (AIE) properties

A technology of aggregation-induced luminescence and light-conversion film, which is applied in the field of green light dyes and flat-panel displays, and can solve problems such as unreported, increased display panel thickness, and insufficient film absorption.

Inactive Publication Date: 2017-06-09
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the commonly used organic dyes are prone to aggregation between molecules, resulting in fluorescence quenching, and almost no light in the thin film state. Dispersed in transparent polymer resin, too low concentration will often lead to insufficient light absorption of the film. To obtain sufficient light conversion effect, the thickness of the film must be increased, resulting in an increase in the thickness of the entire display panel
[0007] Academician Tang Benzhong of the Hong Kong University of Science and Technology proposed the concept of aggregation-induced emission (AIE). This type of AIE-type molecule has a high quantum yield in the solid state. The solid-state quantum yield of molecules composed of benzothiadiazole and tetraphenylethylene is The yield (QY) reached 89% (references: Chem.Commun., 2011, 47, 8847–8849), and this type of molecule is widely used in bioluminescent probes, ion detection, OLED light-emitting layer materials, etc., but its The application in organic light conversion film materials has not been reported, and the high quantum yield of AIE-type molecules in the solid state gives them a natural advantage in the application in this field

Method used

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  • Light conversion film for green dye containing agglomeration-induced emission (AIE) properties
  • Light conversion film for green dye containing agglomeration-induced emission (AIE) properties
  • Light conversion film for green dye containing agglomeration-induced emission (AIE) properties

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The synthesis of embodiment 1 green light dye GA1:

[0044]

[0045] (1) Synthesis of compound 3a

[0046] Synthesis steps: Dissolve compound 1a (commercially available) (5.61g, 20mmol) in anhydrous THF (100mL) under nitrogen protection, cool the reaction solution to 0°C, slowly add butyllithium (2.2M, 14mL) dropwise under stirring After the dropwise addition, continue stirring at low temperature for 1 h, then add compound 2a (commercially available) (10.45 g, 40 mmol) into the reaction solution, and continue stirring at low temperature for 1 h. The reaction solution was then warmed to room temperature and stirred overnight.

[0047] Post-reaction treatment: After the reaction, the reaction solution was poured into water, extracted with EA (100mL*3) and separated, the organic layers were combined, dried with anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The crude product was directly used in the next reaction without purification.

[...

Embodiment 2

[0060] The synthesis of embodiment 2 green light dye GA1:

[0061]

[0062] (1) Synthesis of compound 3b

[0063] Synthetic steps: add compound 6a (commercially available) (2.93g, 10mmol) to 250mL reaction flask, compound 2b (commercially available) (2.68g, 22mmol), tetrakistriphenylphosphine palladium (1.15g, 5%), K 2 CO 3 (4.14g, 30mmol), toluene (100mL) and water (20mL). Nitrogen was evacuated 3 times, heated up to 80° C., kept at this temperature, and reacted for 8 hours. TLC detected that the reaction of compound 6a was complete.

[0064] Post-reaction treatment: Stop heating, lower the temperature to 20°C, pour the reaction liquid into water, extract and separate the liquids with EA (100 mL*3), combine the organic layers, dry with anhydrous sodium sulfate, and evaporate to dryness under reduced pressure. The crude product was subjected to column chromatography to obtain pale yellow compound 3b (2.3g, yield 79.8%). 1 H NMR (400 MHz, CHLOROFORM-d) δ = 7.97 (d, J = 7...

Embodiment 3

[0073] The photophysical property test of embodiment 3 green light dyes GA1 and GA2:

[0074] The test of photophysical properties of green light dyes GA1 and GA2 in solution is to dissolve the corresponding dyes in toluene or dichloromethane, and the concentration of the solution is 1×10 -5 mol / L, the dye-based CCF film was prepared by dissolving the dye and the corresponding proportion of PMMA in toluene, and then drying it. The photophysical properties of the dye film were measured after the dye was dissolved in THF and then spin-coated to prepare the film. The effect of CCF films prepared with GA1 and GA2 on background blue light (λ max ≈450nm) has good absorption, and the emitted light is green light. The fluorescence of GA1 and GA2 in solution is weak (QY<50%), and they show strong fluorescence after being made into solid or PMMA film, with With typical AIE properties, the present invention applies AIE dye molecules to organic light conversion film materials for the fir...

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Abstract

The invention relates to a light conversion film for green dye containing agglomeration-induced emission (AIE) properties. The light conversion film is formed by the green dye and cured polymer resin, and the molecular structure of the green dye is as described in the formula (I). The green dye with the AIE properties is used to produce the light conversion film for the first time, green rays can be sent out under blue light, strong fluorescence is presented after the green dye is produced into solid or PMMA (polymethyl methacrylate) film, and the application of dye in solid high luminescence to organic light-converting film materials has great advantages.

Description

technical field [0001] The invention relates to a light conversion film, in particular to a class of green light dyes containing tetraphenylethylene groups with aggregation-induced luminescent properties, which are made into a light conversion film by solution spin coating and can be applied to plane displays. Background technique [0002] With the continuous breakthrough of the display industry technology and the increasing market demand, the flat panel display has risen rapidly due to its advantages of small size, light weight, low power consumption, low radiation, and good electromagnetic compatibility, and has become the mainstream of display technology in the 21st century. . The color forming method of the flat panel display plays a very important role in its production process, and its quality directly determines the color rendering effect, production cost and service life of the flat panel display. [0003] At present, the mainstream technology for realizing color di...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09K11/02C09B67/02C09B57/00C08L33/12
CPCC08J5/18C08J2333/12C08L33/12C08L2203/16C09B57/00C09B67/0097C09K11/025C09K11/06C09K2211/1051
Inventor 周鹏程戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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