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Triphenylamine derivative pure-organic room-temperature phosphorescent material and preparation method thereof

A technology of room temperature phosphorescence and derivatives, applied in organic chemistry methods, preparation of organic compounds, luminescent materials, etc., can solve problems such as lack of pure organic room temperature phosphorescence materials, single molecular structure, limited application research, etc., and achieve raw material price Inexpensive, simple preparation method, high luminous efficiency

Active Publication Date: 2019-11-05
HKUST SHENZHEN RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a pure organic room temperature phosphorescent material of triphenylamine derivatives and its preparation method, to solve the problem of the extreme shortage of pure organic room temperature phosphorescent materials in the prior art, single molecular structure, poor luminescence performance and application research limited issues

Method used

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  • Triphenylamine derivative pure-organic room-temperature phosphorescent material and preparation method thereof
  • Triphenylamine derivative pure-organic room-temperature phosphorescent material and preparation method thereof
  • Triphenylamine derivative pure-organic room-temperature phosphorescent material and preparation method thereof

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preparation example Construction

[0062] Such as figure 1 Shown, the preparation method of above-mentioned pure organic room temperature phosphorescence material, comprises:

[0063] will react raw material And metal catalysts and alkaline reagents carry out coupling reactions in polar solvents. The reaction temperature of the coupling reaction is 10°C to 20°C higher than the boiling point of the polar solvent. The reaction time of the coupling reaction is 24-48 hours.

[0064] Wherein, alkaline reagent is potassium carbonate, alkaline reagent and reaction raw material The molar ratio is 1.2~1.5:1. Metal catalyst comprises copper powder and cuprous iodide, and the molar ratio of copper powder and cuprous iodide is 4:1, and the total amount of copper powder and cuprous iodide and reaction raw material The molar ratio is 1:4. That is to say, copper powder, cuprous iodide and reaction raw materials The molar ratio is 0.2:0.05:1. Reaction material and The molar ratio is 1:1.2~1.5. The polar solven...

Embodiment 1

[0066] Embodiment 1: the synthesis of compound A1

[0067]

[0068] Diphenylamine (846.1mg, 5.0mmol), methyl 2-iodobenzoate (1.6g, 6.0mmol), copper powder (63.6mg, 1.0mmol), cuprous iodide (47.6mg, 0.25mmol) and Potassium carbonate (829.3 g, 6.0 mmol) was dissolved in n-butyl ether (10 mL), heated to reflux under nitrogen protection, and stirred for 48 hours. After the reaction was completed, it was filtered through diatomaceous earth, washed several times with dichloromethane, the filtrate was concentrated under reduced pressure, separated by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 2:1), and purified to obtain a light yellow solid product A1 (1.22 g, yield: 80.5%). Figure 22 show 1 H NMR (400MHz, CDCl 3 )δ:7.68(dd,J 1 =8.0Hz,J 2 =1.6Hz,1H),7.39-7.44(m,1H),7.15-7.22(m,6H),6.94-7.01(m,6H),3.42(s,3H).HR-MS(MALDI-TOF), m / z: calcd for C 20 h 17 NO 2 ,303.1259.Found,303.1253.

[0069] figure 2 is the overlay of the fluorescence e...

Embodiment 2

[0070] Embodiment 2: the synthesis of compound A2

[0071]

[0072] The synthetic method of compound A2 is the same as the synthetic method of A1, and the reaction substrate is aniline (931.2mg, 10.0mmol) and o-iodobenzoic acid methyl ester (5.5g, 21.0mmol), and purification obtains yellow solid product A2 (1.97g, produces rate: 54.5%). Figure 23 show 1 H NMR (400MHz, CDCl 3 )δ:7.65(dd,J 1 =8.0Hz,J 2 =1.2Hz, 2H), 7.39-7.43(m, 2H), 7.20-7.11(m, 6H), 6.86(t, J=7.2Hz, 1H), 6.76(d, J=8.0Hz, 2H), 3.39 (s,6H).HR-MS(MALDI-TOF),m / z:calcd for C 22 h 19 NO 4 ,361.1314.Found,361.1327.

[0073] Figure 4 is the overlay of the fluorescence emission spectrum of compound A2 in the crystalline state and the steady-state emission spectrum after a delay of 1 millisecond. The figure shows that the position of the maximum emission peak on the steady-state emission spectrum after a delay of 1 millisecond has a red shift of about 42 nm relative to the fluorescence spectrum, and a new ...

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Abstract

The invention relates to a triphenylamine derivative pure-organic room-temperature phosphorescent material and a preparation method thereof. Triphenylamine containing nitrogen heteroatoms is selectedas a pi-conjugated structure, the triphenylamine derivative pure-organic room-temperature phosphorescent material with the long luminescent life and high luminescent efficiency is firstly obtained. According to the preparation method, different functional groups are easily introduced into a triphenylamine skeleton, preparation is easy, the application of the pure organic room-temperature phosphorescent material to aspects of organic electroluminescent devices, chemical sensors, biological imaging, data encryption, anti-fake labeling and the like is advantageously promoted, the preparation method is simple, raw materials are cheap and easy to obtain, the reaction steps are few, the reaction condition is mild, the yield is high, and industrialization is easy to achieve.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to a pure organic room temperature phosphorescent material of triphenylamine derivatives and a preparation method thereof. Background technique [0002] Phosphorescence refers to the process that after the luminescent molecule is excited to the singlet excited state, its singlet excitons undergo intersystem crossing to form triplet excitons, and then relax to the ground state through radiation. 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 excito...

Claims

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Application Information

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IPC IPC(8): C07C227/08C07C227/18C07C229/58C09K11/06
CPCC07C229/58C09K11/06C09K2211/1007C07B2200/13
Inventor 唐本忠熊玉赵征林荣业赵伟军
Owner HKUST SHENZHEN RES INST
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