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High-efficiency long-service life organic room-temperature phosphorescence material and preparation method thereof

A technology for phosphorescence and preparation steps is applied in the field of high-efficiency and long-life organic room-temperature phosphorescence materials and their preparation, which can solve the problems of weak intermolecular interaction strength and the like, and achieve the effects of low cost, simple synthesis and great application prospects.

Active Publication Date: 2018-12-14
BEIJING NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Inhibition of k by weak intermolecular interactions nr Limited by the packing form of molecules, and the strength of intermolecular interactions is weak

Method used

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  • High-efficiency long-service life organic room-temperature phosphorescence material and preparation method thereof
  • High-efficiency long-service life organic room-temperature phosphorescence material and preparation method thereof
  • High-efficiency long-service life organic room-temperature phosphorescence material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] When W is an ethoxy group, 4-hydroxy xanthone (5.3g, 25mmol), K 2 CO 3 (6.9g, 50mmol), ethyl bromide (2.23mL, 30mmol) were added to a 250mL two-necked flask, an appropriate amount of acetone solvent was added, and refluxed under nitrogen atmosphere for 12 hours. The reaction was completely cooled to room temperature, and an appropriate amount of dilute hydrochloric acid solution (2mol / L) was added until no bubbles were generated, extracted with chloroform, combined and concentrated organic phases to obtain a crude product, which was purified by chromatography to obtain a pure product. and use 1 H-NMR and 13 The structure was characterized by C-NMR, and it was confirmed that the product was the compound of Example 1. . 1 H-NMR (400 MHz, CDCl 3 )δ8.33(dd,J=7.9,1.6Hz,1H),8.25(d,J=8.9Hz,1H),7.73-7.63(m,1H), 7.45(d,J=8.3Hz,1H), 7.37(t, J=7.5Hz, 1H), 6.94(dd, J=8.9, 2.3Hz, 1H), 6.87(d, J=2.3 Hz, 1H), 4.16(q, J=7.0Hz, 2H), 1.49(t,J=7.0Hz,3H). 13 C NMR (126MHz, CDCl 3 ...

Embodiment 2

[0046] When W is a propoxyl group, 4-hydroxy xanthone (5.3g, 25mmol), K 2 CO 3 (6.9g, 50mmol), and bromopropane (2.72mL, 30mmol) were added to a 250mL two-necked flask, an appropriate amount of DMF solvent was added, and refluxed under nitrogen for 5 hours. The reaction was completely cooled to room temperature, and an appropriate amount of dilute hydrochloric acid solution (2mol / L) was added until no bubbles were generated, extracted with chloroform, combined and concentrated organic phases to obtain a crude product, which was purified by chromatography to obtain a pure product. and use 1 H-NMR and 13 The structure was characterized by C-NMR, and it was confirmed that the product was the compound of Example 2. 1 H-NMR (400MHz, CDCl 3 ) δ8.22(dd, J=7.9,1.5Hz,2H),8.12(d,J=8.9Hz,2H),7.61-7.49(m,1H),7.60-7.50(m,1H),7.33-7.19 (m,2H),7.37-7.15(m,2H),6.80(dd,J=8.9,2.3Hz,1H),6.80(dd,J=8.9,2.3Hz,1H),6.68(d,J=2.3 Hz,1H),6.68(d,J=2.3Hz,1H),3.90(t,J=6.6Hz,2H),1.87-1.64 (m,2H),1.01(...

Embodiment 3

[0048] When W is n-butoxy, 4-hydroxy xanthone (5.3g, 25mmol), K 2 CO 3 (6.9g, 50mmol), n-bromobutane (3.23mL, 30mmol) were added to a 250mL two-necked flask, an appropriate amount of acetone solvent was added, and refluxed under nitrogen atmosphere for 12 hours. The reaction was completely cooled to room temperature, and an appropriate amount of dilute hydrochloric acid solution (2mol / L) was added until no bubbles were generated, extracted with chloroform, combined and concentrated organic phases to obtain a crude product, which was purified by chromatography to obtain a pure product. and use 1 H-NMR and 13 The structure was characterized by C-NMR, and it was confirmed that the product was the compound of Example 3. 1 H NMR (400 MHz, CDCl 3 )δ8.32(dd, J=7.9,1.6Hz,1H),8.24(d,J=8.9Hz,1H),7.68(ddd,J=8.6,7.1,1.7Hz,1H),7.45(dd,J =8.4,0.6Hz,1H),7.36(ddd,J=8.0,7.2,1.0Hz,1H),6.93(dd,J=8.9,2.4Hz,1H),6.87(d,J=2.3Hz,1H) ,1.88-1.77(m,2H),1.58-1.47(m,2H),1.01(t,J=7.4Hz, 3H). 13 C NM...

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Abstract

The invention provides an alkoxy, benzyloxy or bromine substituted xanthone derivative and a preparation method thereof. The xanthone derivative is simple in preparation method, has a phosphorescencepeak on a long wavelength peak and is long in phosphorescence service life and high in light emission efficiency. The preparation method of the xanthone derivative comprises the following preparationsteps: 1, putting phenol, potassium carbonate, DMF (Dimethyl Formamide) and methylbenzene into a reaction container, backflowing for 3-5 hours in a nitrogen environment, and carrying out dehydration treatment till the system has no water generation; removing the methylbenzene, recovering to the room temperature, adding 4-bromine-2-fluorobenzonitrile, backflowing for 3-5 hours in the nitrogen environment, after the reaction is completed, diluting the solution with 100mL of methylbenzene, filtering, washing with water, drying so as to obtain a crude product of a crystal, and purifying with a spectrum column so as to obtain an intermediate as shown in the specification; 2, mixing the intermediate obtained in the step 1 with water and sulfuric acid, heating to 150-200 DEG C in the nitrogen environment, stirring, and backflowing for 10-15 hours; after the reaction is completed, cooling to the room temperature, diluting with water, extracting by using trichloromethane and a saturated sodiumchloride solution, combining organic phases, drying, filtering, carrying out vacuum distillation so as to remove the solvent and obtain a crude product of a crystal, and purifying with a spectrum column, so as to obtain an intermediate as shown in the specification.

Description

technical field [0001] The invention belongs to the field of functional organic photoelectric materials, relates to an organic room-temperature phosphorescent material with high efficiency and long life and a preparation method thereof, and provides a new idea and scheme for the design and synthesis of the room-temperature phosphorescent material. Background technique [0002] Room temperature phosphorescence (RTP) materials have become a research hotspot because of their potential applications in electroluminescent displays, sensors, and bioimaging. For example, when a phosphorescent material is used for biological imaging, since the phosphorescent material has a longer luminous lifetime, it can eliminate the interference of the short-lived self-luminescence of the organism. Compared with traditional inorganic and metal complex RTP materials, pure organic RTP materials have the advantages of good processability, low cost, low toxicity, good biocompatibility, and easy regula...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86C09K11/06
CPCC07D311/86C09K11/06C09K2211/1088
Inventor 董永强向雪琴
Owner BEIJING NORMAL UNIVERSITY
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