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Polymer ultraviolet fluorescent material used for anti-counterfeiting technology

A polymer and fluorescence emission technology, applied in luminescent materials, chemical instruments and methods, etc., can solve the problems of fluorescence emission weakening, poor stability, quenching, etc., and achieve strong fluorescence emission, good stability, and high fluorescence emission. Effect

Active Publication Date: 2013-07-10
严梅
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, small molecular organic compounds are easy to crystallize and lead to molecular aggregation, which weakens or quenches the fluorescence emission, so doping is often required in practical applications.
In addition, when used as anti-counterfeiting materials, the volatility of small molecular organic compounds makes the fluorescence disappear after a long time and lose the ability to identify
Therefore, in anti-counterfeiting applications, inorganic materials are used more, but because of their processing difficulties, they are difficult to use in specific fields
Polymer light-emitting materials have attracted widespread attention due to their outstanding features such as simple processing technology, diverse processing methods, low cost, and flexible display. For example, Chinese patent 200810012430. The use of rare earth luminescence to achieve a wider range of applications, however, the incomplete coordination of rare earth ions and the poor stability of rare earth coordination compound units can easily lead to unstable luminescence of the material, and more importantly, its luminescence wavelength cannot be achieved due to the dependence on the emission of rare earth ions. regulation, thereby losing the privacy of anti-counterfeiting

Method used

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  • Polymer ultraviolet fluorescent material used for anti-counterfeiting technology
  • Polymer ultraviolet fluorescent material used for anti-counterfeiting technology
  • Polymer ultraviolet fluorescent material used for anti-counterfeiting technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Synthesis of Polymer P1:

[0019] The synthetic route is as follows:

[0020]

[0021]

[0022] 4-Potassium sulfonate-1,8-naphthalene anhydride (0.64g, 2.0mmol), 8-bromooctylamine (0.42g, 2.0mmol) and glacial acetic acid (50mL) were mixed uniformly, heated to reflux under stirring for 24 hours, cooled , and the solvent was removed under reduced pressure to obtain oily compound P1-1, which was directly used in the next step of synthesis without purification.

[0023] Compound P1-1 and trisphenol (0.25g, 2.0mmol) were dissolved in DMSO (20mL), KOH solution (0.12g dissolved in 5mL of water) was added dropwise under stirring, heated at 100°C for 4 hours, and part of it was removed under reduced pressure Solvent, add ethanol 60mL to heat, filter while hot, and cool to obtain compound P1-2, which is recrystallized from ethanol to obtain 0.85g, yield: 77%.

[0024] Compound P1-2, p-fluorodiphenylsulfone (0.38g, 1.5mmol), 5mL toluene, 5mL DMF and excess K 2 CO 3 Mix w...

Embodiment 2

[0026] Synthesis of Polymer P2:

[0027] The synthetic route is as follows:

[0028]

[0029] 4-Dimethylamino-1,8-naphthalene anhydride (0.48g, 2.0mmol), 4-bromobutylamine hydrochloride (0.38g, 2.0mmol) and glacial acetic acid (50mL) were mixed uniformly, heated to reflux under stirring After 24 hours, it was cooled, poured into water, neutralized to PH=7, extracted with dichloromethane, dried, and the solvent was removed under reduced pressure to obtain compound P2-1, which was directly used in the next step of synthesis without purification.

[0030] Compound P2-1 and trisphenol (0.25g, 2.0mmol) were dissolved in DMSO (20mL), KOH solution (0.12g dissolved in 5mL of water) was added dropwise under stirring, heated at 100°C for 4 hours, and part of it was removed under reduced pressure The solvent was added to dichloromethane for extraction, washed with water, dried, and the solvent was removed to obtain compound P2-2, which was separated on a silica gel column to obtain 0...

Embodiment 3

[0033] Synthesis of Polymer P3:

[0034] The synthetic route is as follows:

[0035]

[0036] Compound P2-2 (0.75g, 1.8mmol), p-fluorobenzophenone (0.39g, 1.8mmol), 5mL toluene, 5mLDMF and excess K 2 CO 3 Mix well, and heat to 160°C for 24 hours under stirring. After cooling, dichloromethane was added, washed with water until neutral, dried, concentrated to about 5 ml, and settled in methanol to obtain filamentous polymer P3. The polymer was purified by sedimentation three times, and dried in vacuum to obtain 0.89 g, yield: 82%. Number average molecular weight: 89000; weight average molecular weight: 174000; fluorescence emission peak position: 488nm.

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Abstract

The invention relates to a polymer fluorescent material and a preparation method thereof, belonging to the technical field of functional polymer materials. The invention provides the polymer fluorescent material which is prepared by introducing a micro-molecular organic light-emitting group with a definite structure to a side chain of a stable polyarylether non-conjugated polymer and a preparation method thereof; the emission wavelength of the polymer depends on emission of the organic light-emitting group grafted on a main chain of the polymer and is not affected by other groups, the advantages of stability and good processability of the polyarylether polymer enables the application scope of an organic micro-molecular light-emitting material to be greatly expanded, and the prepared polymer fluorescent material can be used in luminescence fields like display, anti-counterfeiting and sensing.

Description

field of invention [0001] The invention relates to a polymer fluorescent emitting material, a preparation method and application thereof, and belongs to the technical field of polymer functional materials. Background of the invention [0002] Compared with inorganic light-emitting materials, organic light-emitting small molecule compounds are easy to finely modify the molecular structure to achieve precise regulation of the light-emitting wavelength, obtain the desired light-emitting color and specific emission band, and can be used in a wider range of fields. However, small molecular organic compounds are easy to crystallize and lead to molecular aggregation, which weakens or quenches the fluorescence emission, so doping is often required in practical applications. In addition, when used as anti-counterfeiting materials, the volatility of small molecular organic compounds makes the fluorescence disappear after a long time and lose the ability to identify. Therefore, in ter...

Claims

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Application Information

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IPC IPC(8): C09K11/06C08G65/40
Inventor 高永建张光晋王东贤
Owner 严梅