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Excitation wavelength dependent type ultra-long room temperature phosphorescent polymer material as well as preparation and application thereof

A technology of polymer material and room temperature phosphorescence, which is applied in the direction of luminescent materials, applications, household appliances, etc., can solve the problems that product safety cannot be guaranteed with high quality, safety omissions are easy to occur, and afterglow color cannot be adjusted, etc. The effects of large-scale preparation and use, good solubility and mild preparation conditions

Active Publication Date: 2021-07-09
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, most of the existing amorphous room temperature phosphorescent materials can only show a single luminescent color under the excitation of ultraviolet light of a specified wavelength, and the afterglow color cannot be adjusted. For example, Chinese patent CN112210037A discloses an organic phosphonium salt type Long-life room temperature phosphorescent polymer materials, the amorphous state of this type of material at room temperature has the characteristics of long luminescence lifetime phosphorescence, based on its good water solubility, it can be used as a security ink in the field of anti-counterfeiting, but this kind of luminescence When phosphorescent materials with a single color are used in the field of anti-counterfeiting and security printing, safety omissions are prone to occur, and product safety cannot be guaranteed with high quality. At present, there are few reports on amorphous systems with adjustable afterglow colors. If you want to realize afterglow The development of tunable phosphorescent materials is still a very challenging task

Method used

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  • Excitation wavelength dependent type ultra-long room temperature phosphorescent polymer material as well as preparation and application thereof
  • Excitation wavelength dependent type ultra-long room temperature phosphorescent polymer material as well as preparation and application thereof
  • Excitation wavelength dependent type ultra-long room temperature phosphorescent polymer material as well as preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation method of NYPP-1

[0034] The chemical structural formula of NYPP-1 is as follows:

[0035]

[0036] The preparation steps of NYPP-1 mainly include:

[0037] ①Under a nitrogen atmosphere, dissolve (2-naphthyl)diphenylphosphine in DMF, then add 4-bromo-1-butene at a molar ratio of 1:1, heat at 120°C for 12 hours, then distill under reduced pressure and spin dry , and then purified by column chromatography to obtain N1-PM;

[0038] Characterization of compound N1-PM: 1H NMR (400MHz, CDCl3) δ8.76(d, J=15.3Hz, 1H), 8.20(d, J=8.3Hz, 1H), 8.12(dd, J=8.6, 3.3Hz ,1H),7.91(ddd,J=13.5,12.6,4.8Hz,5H),7.82(dt,J=7.4,3.7Hz,2H),7.77–7.64(m,7H),6.06(ddt,J=16.6 ,10.1,6.4Hz,1H),5.09(dd,J=17.1,1.3Hz,1H),5.01(d,J=10.5Hz,1H),4.16–4.01(m,2H),2.59–2.44(m, 2H).

[0039] ②Weigh 0.021g of compound N1-PM, 0.170g of acrylamide, and 0.004g of azobisisobutyronitrile and dissolve it in 2mL of N,N-dimethylformamide, freeze-vacuum-thaw three times, and react at 65°...

Embodiment 2

[0042] Embodiment 2: the preparation method of NYPP-2

[0043] The chemical structural formula of NYPP-2 is as follows:

[0044]

[0045] The preparation steps of NYPP-2 mainly include:

[0046] ①Under a nitrogen atmosphere, dissolve bis(2-naphthyl)phenylphosphine in DMF, then add 4-bromo-1-butene at a molar ratio of 1:1, heat at 120°C for 16 hours, then distill under reduced pressure and spin dry , and then purified by column chromatography to obtain N2-PM;

[0047]Characterization of compound N2-PM: 1H NMR (400MHz, CDCl3) δ8.79(d, J=15.3Hz, 2H), 8.19(d, J=8.0Hz, 2H), 8.13(dd, J=8.6, 3.3Hz ,2H),8.01–7.91(m,4H),7.83(dd,J=8.4,6.4Hz,1H),7.79–7.66(m,8H),6.11(ddt,J=16.8,10.4,6.4Hz,1H ), 5.10(dd, J=17.0, 1.3Hz, 1H), 5.02(d, J=9.6Hz, 1H), 4.27–4.13(m, 2H), 2.57(s, 2H).

[0048] ② Weigh 0.024g of compound N2-PM, 0.170g of acrylamide, 0.004g of azobisisobutyronitrile and dissolve it in 2mL of N,N-dimethylformamide, freeze-vacuum-thaw three times, and react at 65°C for 12h. The...

Embodiment 3

[0051] Embodiment 3: the preparation method of NYPP-3

[0052] The chemical structural formula of NYPP-3 is as follows:

[0053]

[0054] The preparation steps of NYPP-3 mainly include:

[0055] ①Under a nitrogen atmosphere, dissolve tris(2-naphthyl)phosphine in DMF, then add 4-bromo-1-butene at a molar ratio of 1:1, heat at 120°C for 24 hours, then distill and spin dry under reduced pressure, and then Purify by column chromatography to obtain N3-PM;

[0056] Characterization of compound N3-PM: 1H NMR (400MHz, CDCl3) δ8.67 (d, J = 14.7Hz, 3H), 8.06–7.97 (m, 6H), 7.84 (d, J = 8.0Hz, 3H), 7.67 –7.53(m,9H),6.00(ddt,J=16.8,10.0,6.5Hz,1H),4.99–4.93(m,1H),4.87(d,J=10.1Hz,1H),4.22–4.10(m ,2H),2.47(t,J=16.9Hz,2H).

[0057] ②Weigh 0.026g of compound N3-PM, 0.170g of acrylamide, and 0.004g of azobisisobutyronitrile and dissolve it in 2mL of N,N-dimethylformamide, freeze-vacuum-thaw three times, and react at 65°C for 12h. The resulting product was washed with methanol and dried t...

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Abstract

The invention discloses an excitation wavelength dependent type ultra-long room temperature phosphorescent polymer material as well as preparation and application thereof, wherein the room temperature phosphorescent polymer material comprises three kinds of NYPP-1, NYPP-2 and NYPP-3, and is obtained by taking a triphenylphosphine derivative as a phosphorescent monomer, modifying with different numbers of naphthyl and bromine atoms, and copolymerizing with acrylamide; the obtained polymer has the characteristic of adjustable afterglow color in an amorphous state at room temperature, overcomes the defect of single light emitting color of the conventional room-temperature phosphorescent material, shows yellow afterglow after being irradiated by a 300 nm ultraviolet lamp, and can show red afterglow after being irradiated by a 365 nm ultraviolet lamp; the characteristic of good solubility of the material is utilized, an aqueous solution of the material is used as novel optical anti-counterfeiting ink for water-based printing, the application of the material in the fields of information encryption and anti-counterfeiting can be greatly promoted, the anti-counterfeiting safety is comprehensively improved due to the characteristic of adjustable afterglow color, and a new thought is provided for safe printing.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric functional materials, in particular to a kind of excitation wavelength-dependent ultra-long room temperature phosphorescent polymer material and its preparation and application. Background technique [0002] Organic room-temperature phosphorescent materials have a wide range of applications in anti-counterfeiting, bioimaging, and chemical sensing due to their unique generation process and long-lived luminescent properties. In order to overcome the disadvantages of no room-temperature phosphorescence in the amorphous state and difficulties in practical application of crystalline materials, amorphous room-temperature phosphorescent materials have been developed and applied successively. [0003] However, most of the existing amorphous room temperature phosphorescent materials can only show a single luminescent color under the excitation of ultraviolet light of a specified wavelength, a...

Claims

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Application Information

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IPC IPC(8): C08F220/56C08F230/02C09D11/50C09D11/107C09K11/06
CPCC08F220/56C09D11/50C09D11/107C09K11/06C09K2211/1416C09K2211/1425C09K2211/1433C08F230/02
Inventor 马云刘晨园魏娟赵强刘淑娟
Owner NANJING UNIV OF POSTS & TELECOMM
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