Synthesis of new 3,4,9,10-perylenetetracarboxylic diimide cyclometalated iridium complex and application to regulate fluorescence-phosphorescence dual emission through utilization of solution concentration of complex

A dual-emission, iridium complex technology, applied in indium organic compounds, platinum group organic compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, etc., can solve problems such as unfavorable broad-spectrum emission

Active Publication Date: 2017-11-07
CHANGZHOU UNIV
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  • Abstract
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Problems solved by technology

There are mainly two problems in this kind of compounds: 1. At present, most of the reported single-molecule multicolor light-emitting compounds are fluorescent molecules, and they can only use singlet excitons to emit light, and the internal quantum efficiency is 25%; 2. , Most of its multi-color luminescence spectra come from the same excited state (singlet or triplet state), which leads to the concentration of luminous colors in a small area, which is not conducive to obtaining broad-spectrum emission 13
To the best of our knowledge, there are few reports of multiple emissions from cyclometalated iridium complexes

Method used

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  • Synthesis of new 3,4,9,10-perylenetetracarboxylic diimide cyclometalated iridium complex and application to regulate fluorescence-phosphorescence dual emission through utilization of solution concentration of complex
  • Synthesis of new 3,4,9,10-perylenetetracarboxylic diimide cyclometalated iridium complex and application to regulate fluorescence-phosphorescence dual emission through utilization of solution concentration of complex
  • Synthesis of new 3,4,9,10-perylenetetracarboxylic diimide cyclometalated iridium complex and application to regulate fluorescence-phosphorescence dual emission through utilization of solution concentration of complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] When R 1 When it is a methoxy group, taking the preparation of Ir-1, Ir-2 and Ir-4 as an example, the synthetic route is as follows:

[0039]

[0040] Synthesis of N,N'-di(dodecyl)-3,4,9,10-perylenetetracarboxyimide(1)

[0041] In a 100mL single-necked bottle, add 3,4,9,10-perylenetetracarboxylic dianhydride (1.0g, 2.55mmol), dodecylamine (2.8g, 15.31mmol), 5g imidazole and 5mL toluene in sequence, at 180°C Reaction 24h. Pour the reaction solution into 100mL 2M hydrochloric acid, filter with suction, and filter the cake with CH 2 Cl 2 As the eluent, it was separated by column chromatography to obtain 0.8 g of black-red solid with a yield of 43.2%. 1 H NMR (CDCl 3 ,400MHz,TMS),δ(ppm):8.67(d,J=7.6Hz,4H),8.60(d,J=8.0Hz,4H),4.21(t,J=6.8Hz,4H),1.76(m ,4H),1.46-1.26(m,36H),0.87(m,6H).

[0042] Synthesis of N,N'-bis(dodecyl)-1-nitro-3,4,9,10-perylenetetracarboxyimide (2)

[0043] In a 100mL three-necked flask, add N,N'-bis(dodecyl)-3,4,9,10-perylenetetracarboxylic d...

Embodiment 2

[0068] Perylene imide ligand and ring metal iridium complex ultraviolet performance test in embodiment 1:

[0069] The perylene imide auxiliary ligand and ionic cyclometal iridium complexes Ir-1, Ir-2 and Ir-4 were dissolved in chloroform solution (10 -5 mol / L), measure its ultraviolet absorption performance at room temperature, and its ultraviolet absorption spectrum is as figure 1 shown. Ligands and cyclometalated iridium complexes exhibit similar absorption spectra in the UV-vis region. According to similar literature reports, the absorption of strong absorption in the 240-580nm region is mainly attributed to the π-π allowed by the ligand spin * transitions, i.e. π-π including phenylpyridine * Transition, π-π of phenylisoquinoline * Transition, π-π of 4-[N,N-bis(4-methoxyphenyl)amino]phenyl-2-pyridine * Transition, π-π of 2-(4-dimethylborophenyl)pyridine * jump. The region from 530nm to 580nm shows a weaker absorption peak, which is mainly caused by the metal-to-liga...

Embodiment 3

[0071] Photoluminescence performance test of perylene imide ligand and cyclometal iridium complex in Example 1:

[0072] The perylene imide ligand and the ring metal iridium complexes Ir-1, Ir-2 and Ir-4 were dissolved in chloroform, and the concentration was 1.0×10 -5 M and 1.0×10 -2 M solution, test its photoluminescence performance at room temperature, its photoluminescence spectrum is as follows figure 2 shown. When the excitation wavelength is 443nm, at low concentration (10 -5 M), the peryleneimide ligand has stronger emission at 481nm and 516nm ( figure 2 ). At the same time, the emission spectrum of the iridium complex is similar to that of the ligand, with a strong emission at 470-540nm, which is mainly attributed to the π-π transition of the peryleneimide ligand. At high concentrations (10 -2 M), the emission peak of the peryleneimide ligand is red-shifted by nearly 80nm compared with its low concentration, and there is a maximum emission at 600nm, which is m...

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Abstract

The invention discloses a 3,4,9,10-perylenetetracarboxylic-diimide-based cyclometalated iridium complex fluorescence-phosphorescence dual emission material and an application to regulate excited state luminescence through utilization of the solution concentration of the material. The cyclometalated iridium complex takes a 3,4,9,10-perylenetetracarboxylic diimide derivative as an auxiliary ligand and takes a phenyl pyridine derivative as a main ligand unit. Through introduction of triphenylamine, carbazole and Mi borane electron-donating / electron-withdrawing groups to phenyl pyridine, energy levels of the ligand and complex are regulated. The material in a low-concentration solution (10<-5>M) emits yellow fluorescence, and has a maximum emission peak of 520 nm. The material in a high-concentration solution (10<-2>M) emits near-infrared phosphorescence, and has a maximum emission peak of 740 nm. As far as we know, it is reported for the first time, the excited state luminescence of the cyclometalated iridium complex is regulated through utilization of the solution concentration.

Description

technical field [0001] The present invention relates to the field of single-molecule fluorescence-phosphorescence dual emission: 1. It relates to a class of ring metal iridium complexes with perylene imide derivatives as auxiliary ligands and phenylpyridine derivatives as main ligands; 2. These ring Metal iridium complexes exhibit short-wavelength fluorescence emission in low-concentration solutions, and near-infrared phosphorescence emission in high-concentration solutions. To the best of our knowledge, this is the first report of a cyclometalated iridium complex whose excited-state emission is regulated by solution concentration. Background technique [0002] Single-molecule multicolor luminescent materials can emit different color spectra under different conditions, so they have broad application prospects in the fields of full-color displays, optical sensors, and light conversion. 1-7 . This single-molecule polychromatic light-emitting compound is usually caused by rel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC07F15/0033C09K11/06C09K2211/185
Inventor 王亚飞石军伟朱卫国
Owner CHANGZHOU UNIV
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