Pure organic room-temperature phosphorescent material of distorted donor-receptor structure and preparation method and application of pure organic room-temperature phosphorescent material

A room temperature phosphorescence and organic technology, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of single molecular structure, poor luminescence performance, and lack of pure organic room temperature phosphorescence materials, etc., and achieves a simple and good preparation method. The effect of luminous performance and high yield

Active Publication Date: 2019-11-05
HKUST SHENZHEN RES INST
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Problems solved by technology

[0006] The object of the present invention is to provide a pure organic room-temperature phosphorescent material with a twisted donor-acceptor structure and its preparation method and application, so

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  • Pure organic room-temperature phosphorescent material of distorted donor-receptor structure and preparation method and application of pure organic room-temperature phosphorescent material
  • Pure organic room-temperature phosphorescent material of distorted donor-receptor structure and preparation method and application of pure organic room-temperature phosphorescent material
  • Pure organic room-temperature phosphorescent material of distorted donor-receptor structure and preparation method and application of pure organic room-temperature phosphorescent material

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preparation example Construction

[0050] The present invention also provides a method for preparing the above-mentioned pure organic room temperature phosphorescent material, comprising:

[0051]

[0052] The compound represented by formula III is mixed with reaction raw materials, alkaline reagent and dehydrating agent, and esterified in a polar organic solvent to obtain a pure organic room-temperature phosphorescent material with a distorted donor-acceptor structure. The reaction temperature of the esterification reaction is room temperature; the reaction time of the esterification reaction is 6-24 hours.

[0053] When preparing the pure organic room temperature phosphorescent material shown in formula I, the reaction raw material is ROH; when preparing the pure organic room temperature phosphorescent material shown in formula II, the reaction raw material is OH-R'-OH; wherein, X H, F, Cl, Br or I; R is H, 1-10 carbon alkyl chain, 1-10 carbon glycol chain, phenyl, bromophenyl, iodophenyl, allyl 2-hydroxy...

Embodiment 1

[0056] Embodiment 1: the synthesis of compound A1

[0057]

[0058] Weigh 2-(9H-carbazol-9-yl)benzoic acid (402.0mg, 1.4mmol), DMAP (324.1 mg, 2.8mmol), EDCl (0.55g, 2.8mmol) and n-butanol (103.8mg, 1.4 mmol), dissolved in dichloromethane (10 mL), and stirred at room temperature for 24 hours under nitrogen protection. After the reaction, add water to the reaction solution, extract 3 times with dichloromethane, dry with anhydrous magnesium sulfate after the organic phases are combined, concentrate under reduced pressure, separate by silica gel column chromatography (eluent is sherwood oil: dichloromethane =2:1), recrystallized in n-hexane / dichloromethane mixed solvent to obtain white crystalline compound A1 (0.3 g, yield: 62.4%). Figure 16 show 1 H NMR (400MHz, CDCl 3 )δ:8.11-8.15(m,3H), 7.75(dt,J 1 =7.6Hz,J 2 =1.2Hz,1H),7.55-7.62(m,2H),7.34-7.38(m,2H), 7.24-7.27(m,2H),7.13(s,1H),7.10(s,1H),3.60( t,J=6.4Hz,2H), 0.68-0.73(m,2H),0.59-0.64(m,2H),0.52(t,J=6.8Hz,3H).HR-MS ...

Embodiment 2

[0061] Embodiment 2: the synthesis of compound A2

[0062]

[0063] The synthetic method of compound A2 is the same as that of A1, the reaction substrates are 2-(9H-carbazol-9-yl)benzoic acid (574.6mg, 2.0mmol) and n-hexanol (204.3mg, 2.0mmol), and purified to obtain White crystalline compound A2 (0.6 g, yield: 80.8%). Figure 17 show 1 H NMR (400 MHz, CDCl 3 )δ:8.11-8.15(m,3H),7.74(dt,J 1 =8.0Hz,J 2 =1.2Hz,1H), 7.55-7.62(m,2H),7.34-7.38(m,2H),7.23-7.27(m,2H),7.13(s,1H),7.11(s, 1H),3.58( t, J=6.4Hz, 2H), 0.87-1.03(m, 2H), 0.57-0.86(m, 9H). MALDI-TOF, m / z: 371.3.

[0064] Figure 5 It is the overlay of the steady-state emission spectrum of compound A2 in the crystalline state and the steady-state emission spectrum after a delay of 10 milliseconds. The figure shows that the position of the emission peak in the steady-state emission spectrum after a delay of 10 milliseconds is consistent with the position of the emission peak at the long-wave band in the steady-state em...

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Abstract

The invention relates to a pure organic room-temperature phosphorescent material of a distorted donor-receptor structure and a preparation method and application of the pure organic room-temperature phosphorescent material. By simply establishing a pi-conjugated structure with a distorted donor-receptor structure, a pure organic room-temperature phosphorescent material which is long in light emission life and high in light emission efficiency can be prepared. The pure organic room-temperature phosphorescent material is simple in preparation method, low in raw material price, easy in raw material obtaining, small in reaction step, mild in reaction condition, high in yield and easy in industrialization; and by adopting the preparation method, different function groups can be introduced to the tail end of an alkyl side chain, and application of the pure organic room-temperature phosphorescent material in aspects such as organic electroluminescence devices, chemical sensation, biological imaging, data encryption and anti-fake marking can be promoted.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to a pure organic room-temperature phosphorescent material with a twisted donor-acceptor structure and its preparation method and application. Background technique [0002] Phosphorescence is a slow-emitting photoluminescence phenomenon, that is, after the excitation stops, its luminescence can last for a period of time (such as figure 1 shown). Compared with traditional fluorescent materials, the advantages of phosphorescent materials are mainly reflected in their longer luminous lifetime, which can eliminate the interference of biological autofluorescence (nanosecond level) and reduce background noise, thereby achieving high resolution. and high signal-to-noise ratio biological imaging. On the other hand, in the process of electroluminescence, phosphorescent materials can simultaneously use singlet and triplet excitons to emit light, breaking through the upper limi...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C07D209/88
CPCC09K11/06C07D209/86C07D209/88C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1014Y02E10/549
Inventor 唐本忠熊玉赵征林荣业王志明赵伟军
Owner HKUST SHENZHEN RES INST
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