A pure organic material with strong yellow afterglow and its preparation method and application

A technology of organic materials and luminescent materials, applied in the field of organic afterglow luminescent materials, can solve problems such as low luminous efficiency, and achieve the effects of simple structure, excellent afterglow luminescent performance, and high phosphorescence quantum efficiency

Active Publication Date: 2022-02-22
TIANJIN NORMAL UNIVERSITY
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Problems solved by technology

[0003] The purpose of the present invention is to aim at the technical defects existing in the prior art, and provide a pure organic material with strong yellow afterglow luminescence and its preparation method and application. The afterglow luminous efficiency is greater than 10%, which overcomes the luminous efficiency of pure organic afterglow luminescent materials. low problem

Method used

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  • A pure organic material with strong yellow afterglow and its preparation method and application
  • A pure organic material with strong yellow afterglow and its preparation method and application
  • A pure organic material with strong yellow afterglow and its preparation method and application

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Effect test

Embodiment 1

[0032] Preparation of BBr: benzo[b]carbazole (0.1 g, 0.46 mmol) was dissolved in 10 mL of DMF, and stirred for 10 minutes under an ice-water bath. NaH (0.06 g, 60%) was slowly added to the above solution, and stirring was continued at 0° C. for 1 hour. Add 1-bromo-4-(5-bromophenoxy)benzene (0.17g dissolved in 5mL DMF) solution dropwise to the above solution, continue stirring for 2 hours, pour into 200mL water, and filter with suction to obtain a light yellow solid. Column chromatography purification (petroleum ether / CH 2 Cl 2 = 2 / 1). Yield: 17%. Elemental analysis: theoretical value: C, 71.19; H, 5.55; N, 2.96; actual value: C, 71.15; H, 5.58; N, 2.93. 1 H NMR (400MHz, d6-DMSO) δ8.73(s, 1H), 8.30(d, J=7.6Hz, 1H), 8.08(d, J=8.3Hz, 1H), 8.02(d, J=8.5Hz ,1H),7.97(s,1H),7.60(d,J=8.2Hz,1H),7.54(t,J=7.5Hz,1H),7.48(t,J=7.0Hz,1H),7.39(t ,J=7.0Hz,1H),7.38(d,J=10.0Hz,2H),7.24(t,J=7.4Hz,1H),6.81(J=9.0Hz,2H),4.45(t,J=6.9 Hz,2H),3.88(t,J=6.4Hz,2H),1.87(m,2H),1.65(m,2H),1.44(m,4H). ...

Embodiment 2

[0034] Preparation of ABr: ABr was prepared according to the conditions for the synthesis of BBr. A colorless solid was obtained, yield: 42%. Elemental analysis: theoretical value: C, 68.25; H, 5.73; N, 3.32; actual value: C, 68.28; H, 5.70; N, 3.34. 1 H NMR (400MHz, CDCl 3 )δ8.13(d, J=7.7Hz, 2H), 7.53–7.46(m, 2H), 7.43(d, J=8.1Hz, 2H), 7.40–7.36(m, 2H), 7.28–7.21(m ,2H),6.74(d,J=9.0Hz,2H),4.35(t,J=7.1Hz,2H),3.89(t,J=6.4Hz,2H),2.04–1.90(m,2H),1.80 –1.67(m,2H),1.53–1.40(m,4H). 13 C NMR (101MHz, CDCl3 )δ158.14,140.44,132.22,125.63,122.86,120.40,118.79,116.29,112.66,108.64,67.97,42.94,29.02,28.95,27.06,25.92.HRMS(m / z):[M+H] + calcd.for C 24 h 25 BrNO, 422.1114; found, 422.1110.

Embodiment 3

[0036] Preparation of AI: Prepare AI according to the conditions for synthesizing BBr. A colorless solid was obtained, yield: 54%. Elemental analysis: theoretical value: C, 61.42; H, 5.15; N, 2.98; actual value: C, 61.46; H, 5.13; N, 2.94. 1 H NMR (400MHz, CDCl 3 )δ8.12(s,2H),7.54(s,2H),7.51–7.46(m,2H),7.43(d,J=8.1Hz,2H),7.28–7.21(m,2H),6.64(d ,J=9.0Hz,2H),4.35(t,J=7.1Hz,2H),3.88(t,J=6.4Hz,2H),1.94(m,2H),1.75(m,2H),1.49(m ,4H). 13 C NMR (101MHz, CDCl 3 )δ158.89,140.42,138.17,125.62,122.85,120.39,118.78,116.90,108.63,82.50,67.82,42.93,28.99,28.94,27.05,25.91.HRMS(m / z):[M+H] + calcd.for C 24 h 25 INO, 470.0981; found, 470.0976.

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Abstract

The invention discloses a pure organic material with strong yellow afterglow luminescence and its preparation method and application. The organic compound AX and BBr are mixed, the molar content of the AX is 80%-99.9%, and the BBr The molar content is 0.1% to 20%; when BBr is doped into ABr at a concentration of 0.1% to 10%, the obtained material emits white light under the excitation of ultraviolet light, and the phosphorescence quantum efficiency is between 12 and 39%. The life span is between 90 and 168ms. When BBr is doped into Al at a concentration of 0.1%-10%, the obtained material emits yellow light under the excitation of ultraviolet light, the phosphorescence quantum efficiency is between 19-51%, and the phosphorescence lifetime is between 9-30ms. The preparation method of the material involved in the invention is simple, and due to the high phosphorescence quantum efficiency, the material will have wide application in the fields of biological imaging, anti-counterfeiting marks and the like.

Description

technical field [0001] The invention relates to the technical field of organic afterglow luminescent materials, in particular to an organic material of pure organic material with strong yellow afterglow luminescence, a preparation method and application thereof. Background technique [0002] Materials with room-temperature phosphorescence have been widely used in road markings, emergency signs, biomarkers, and electroluminescent diodes. Among them, afterglow luminescent materials with a luminous time of more than 20 ms have attracted much attention due to their advantages of eliminating background emission noise. Such materials are mostly inorganic materials containing rare earth elements. Due to intermolecular and vibrational quenching, purely organic afterglow materials have rarely been reported. Adachi doped different compounds in the vitreous body of estradiol to obtain afterglow luminescent materials with different colors (Adv. Funct. Mater. 2013, 23, 3386; J. Phys. C...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D209/80C09K11/06
CPCC07D209/86C07D209/80C09K11/06C09K2211/1029C09K2211/1007C07B2200/13
Inventor 薛鹏冲
Owner TIANJIN NORMAL UNIVERSITY
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