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Diphenylamine derivative organic room temperature phosphorescent compound and its preparation method and application

A room temperature phosphorescence and compound technology, applied in the field of materials science, can solve the problems of lack of theoretical guidance for molecular design and insufficient understanding of luminescent mechanism, and achieve the effects of high yield, low cost and simple synthesis steps

Active Publication Date: 2022-04-26
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, in the prior art, so far, such materials are still relatively rare, the main reason is that the understanding of their light-emitting mechanism is not deep enough, so there is a lack of theoretical guidance for molecular design

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  • Diphenylamine derivative organic room temperature phosphorescent compound and its preparation method and application
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  • Diphenylamine derivative organic room temperature phosphorescent compound and its preparation method and application

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preparation example Construction

[0035] Preparation method of diphenylamine derivative organic room temperature phosphorescent compound

[0036] In the second aspect of the present invention, the present invention provides a method for preparing the diphenylamine derivative organic room temperature phosphorescent compound described in the first aspect of the present invention, and the diphenylamine derivative organic room temperature phosphorescent compound is represented by formula 2 The compound and the compound shown in formula 3 are prepared, and the reaction formula is as follows:

[0037]

[0038] Among them, R 1 , R 2 , R 3 , R 4 Each independently selected from one of hydrogen, C1~C6 alkyl; preferably, R 1 One selected from methyl, isopropyl and tert-butyl; R 2 is hydrogen or methyl; R 3 is hydrogen or methyl; R 4 is hydrogen or methyl.

[0039] In one or more embodiments of the present invention, the preparation method of diphenylamine derivative organic room temperature phosphorescent com...

Embodiment 1

[0052] Example 1: DPA

[0053] The structural formula of compound DPA is as follows:

[0054]

[0055] Compound DPA is commercially available. Using petroleum ether as the eluent, the compound DPA was chromatographed on a silica gel column, separated and purified, and dried in vacuo to obtain a white solid compound DPA, and the H NMR and C NMR spectra ( 1 H NMR, 13 C NMR) characterizes the structure, confirms that this white solid is compound DPA. The test results are as follows:

[0056] DPA: 1 H NMR (400MHz, CDCl 3 )δ7.28(s,1H),7.27(d,J=1.1Hz,2H),7.25(d,J=2.0Hz,1H),7.09(d,J=1.1Hz,3H),7.06(d, J=1.0Hz, 2H), 6.95–6.90(m, 2H), 5.70(s, 1H). 13 C NMR (100MHz, CDCl 3 )δ143.11, 129.34, 120.99, 117.80.

Embodiment 2

[0057] Embodiment 2: Synthesis of S1-DPA-Me

[0058] The structural formula of the target compound S1-DPA-Me is as follows:

[0059]

[0060] The synthesis of S1-DPA-Me comprises the following steps:

[0061] Under nitrogen protection, in a reaction flask, 2-methylaniline (1.62mL, 15mmol, 1eq.), 2-bromobenzene (1.73mL, 16.5mmol, 1.1eq.), NaOtBu (2.88g, 30mmol, 2eq .) and Pd(dppf)Cl 2 ·CH 2 Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]palladium dichloride) (0.37 g, 0.45 mmol, 0.03 eq.) was dissolved in sufficient toluene solvent. The mixture was heated to 110° C. with stirring, and the reaction was continued for 16 hours. After the reaction mixture was cooled to room temperature (15-35°C), the reaction was quenched with 1M dilute hydrochloric acid, and then extracted with dichloromethane. The obtained organic layer was washed with saturated aqueous sodium chloride solution (200 mL), dried over anhydrous sodium sulfate Removal of solvent gave crude product. Using petrol...

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Abstract

The present invention provides a diphenylamine derivative organic room temperature phosphorescent compound, which is characterized in that the structural formula of the diphenylamine derivative organic room temperature phosphorescent compound is shown in Formula 1, wherein R 1 , R 2 , R 3 , R 4 Each independently selected from one of hydrogen and C1-C6 alkyl. The diphenylamine derivative organic room-temperature phosphorescent compound has a long afterglow phenomenon, and its solid crystals can all undergo room-temperature phosphorescence, and the phosphorescence lifetime is as long as 660ms at room temperature. The invention also provides a method for preparing the above diphenylamine derivative organic room temperature phosphorescent compound, which has simple synthesis steps, mild preparation conditions, high yield and low cost, and is suitable for large-scale production. The above diphenylamine derivative organic room temperature phosphorescent compound can be applied to prepare anti-counterfeiting marks, anti-counterfeiting films and the like.

Description

technical field [0001] The invention relates to the technical field of material science, in particular to a diphenylamine derivative organic room-temperature phosphorescent compound and a preparation method and application thereof. Background technique [0002] Pure organic room-temperature phosphorescent materials with ultra-long luminescence lifetime can be applied in the fields of organic light-emitting diodes (OLEDs), biological imaging, chemical sensors, optics and anti-counterfeiting technology due to their afterglow properties after removal of the excitation light source. In recent years, it has attracted much attention because of its broad application prospects. [0003] However, in the prior art, so far, such materials are still relatively rare, mainly because the understanding of their light-emitting mechanism is not deep enough, thus lacking theoretical guidance for molecular design. [0004] Therefore, it is necessary to develop long-lived pure organic room-temp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/55C07C209/10C07C209/84C09K11/06B42D25/36
CPCC07C211/55C07C209/10C07C209/84C09K11/06B42D25/36C09K2211/1014
Inventor 李倩倩高原李振
Owner WUHAN UNIV
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