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Small conjugated phosphorescent metal iridium (III) complexes with isomer as well as preparation method and application of small conjugated phosphorescent metal iridium (III) complexes

A technology of conjugated phosphorescence and complexes, which is applied in the direction of indium organic compounds, platinum group organic compounds, compounds containing group 8/9/10/18 elements of the periodic table, etc., which can solve the problems affecting the preparation of OLED devices, high prices, The poor solubility of red light complexes and other problems can achieve the effect of small conjugated red phosphorescent emission, reduced energy gap, and efficient separation and purification

Pending Publication Date: 2021-08-03
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the increase in the degree of ligand conjugation reduces the solubility of the complex, which affects the preparation of OLED devices. The development of small conjugated red phosphorescent iridium (III) complexes can well solve the problem of poor solubility of red light complexes.
In addition, due to the high price of precious metal iridium, the commercialization of OLEDs devices using metal iridium(III) complexes as light-emitting materials lacks cost competitiveness.

Method used

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  • Small conjugated phosphorescent metal iridium (III) complexes with isomer as well as preparation method and application of small conjugated phosphorescent metal iridium (III) complexes
  • Small conjugated phosphorescent metal iridium (III) complexes with isomer as well as preparation method and application of small conjugated phosphorescent metal iridium (III) complexes
  • Small conjugated phosphorescent metal iridium (III) complexes with isomer as well as preparation method and application of small conjugated phosphorescent metal iridium (III) complexes

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Example 1: Preparation of a new type of small conjugated phosphorescent metal iridium (III) complexes Ir1-a, Ir1-b, Ir1-c with isomers, confirm the complexes obtained in each step during the preparation process, NMR spectrum such as Figure 1-3 , Figure 7-12 shown.

[0050]

[0051] (1) Preparation of compound 3: 2-chloro-4-trifluoromethylpyridine compound (1mmol, 300mg) and 3-methoxyphenylboronic acid (1.05mmol, 264mg) and tetrakis (triphenylphosphine) palladium ( 0.05mmol, 955mg), was added to a mixed solvent of 80mL toluene, 15mL methanol, and 15mL saturated solution of potassium carbonate, at a temperature of 85°C, nitrogen protection, reflux reaction for 18h, cooled to room temperature, extracted with dichloromethane, and washed with water, After drying with anhydrous sodium carbonate, and spin-dried the solvent under reduced pressure, the crude product was purified by chromatographic column separation, the eluent was petroleum ether: ethyl acetate 200:1 for ...

Embodiment 2

[0057] Example 2: Preparation of a class of novel small conjugated phosphorescent metal iridium (III) complexes Ir2-a, Ir2-b, and Ir2-c with isomers, confirming the complexes obtained in each step during the preparation process, NMR spectrum such as Figure 4-6 , Figure 13-18 shown.

[0058]

[0059] The preparation method of complexes Ir2-a, Ir2-b, and Ir2-c of this example refers to Example 1, the difference is that the raw material 2-chloro-5-trifluoromethylpyridine is used to replace 2-chloro-4-trifluoromethyl Based pyridine, the yields were 33%, 38%, 12%, and the total yield was 83%.

[0060] 2-(3-Methoxy-phenyl)-5-trifluoromethylpyridine: 1 H NMR (400MHz, CDCl 3 ,δ):8.94(s,1H),7.98(dd,J=8.4,2.4Hz,1H),7.84(d,J=8.4Hz,1H),7.63(t,J=3.8Hz,1H),7.58 (dd, J=7.7,1.6Hz,1H),7.42(t,J=8.0Hz,1H),7.03(dd,J=8.2,2.6Hz,1H),3.91(s,3H). 19 F{1H}NMR (376MHz, CDCl 3 δ): -62.23(s).

[0061] Ir2-a (33%): 1 H NMR (400MHz, CDCl 3 ,δ):8.75(s,2H),7.92(d,J=2.0Hz,4H),7.19(d,J=2.6Hz,2H),...

Embodiment 3

[0064] Embodiment 3: the determination of the crystal structure of metal iridium (III) complexes

[0065] X-ray diffraction data were collected with a Bruker Smart CCD Apex DUO diffractometer in ω-2θ scan mode using graphite monochromatized Mo Kα rays as a light source. The test data are corrected by Lorentz and polarization effects. Structural elucidation was performed by the direct method and further refined using the full matrix least squares method of the Olex2 software. All calculations and molecular structure diagrams were carried out with the Olex2 software package and Mercury language. The crystal structure is as follows: Figure 19 shown.

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Abstract

The invention discloses small conjugated phosphorescent metal iridium (III) complexes with isomers as well as a preparation method and application of the complexes. The three isomer complexes with different light emission properties can be obtained through a one-step complex synthesis reaction and a simple column chromatographic separation and purification technology. The complexes are mainly composed of 2-phenylpyridine, methoxy groups with an electron donating property and trifluoromethyl groups with an electron withdrawing property. The phosphorescent metal iridium (III) complexes with three emission wavelengths of orange, orange red and red light are obtained through one-step reaction, so the production process flow of the phosphorescent metal iridium (III) complexes with different emission wavelengths can be simplified, and cost is reduced; and in addition, the obtained red phosphorescent metal iridium (III) complexes has small conjugation properties , is an electroluminescent material with good solubility, and is applied to low-cost OLED display devices and white-light OLED devices.

Description

technical field [0001] The invention relates to a class of small conjugated phosphorescent metal iridium (III) complexes with isomers, a preparation method and application thereof, and belongs to the technical field of organic photoelectric materials. Background technique [0002] Due to the demand for full-color flat panel displays and low-cost light sources, the exploration of organic electroluminescent materials in the preparation of high-efficiency organic light-emitting diodes (OLEDs) has been the focus of research. Compared with fluorescent materials, phosphorescent transition metal complexes can simultaneously utilize singlet and triplet excitons to achieve 100% internal quantum efficiency and significantly improve device performance. The strong spin-orbit coupling effect of heavy metal atoms is used to improve the phosphorescence efficiency of transition metal complexes. Among phosphorescent transition metal complexes, cyclometalated iridium(III) complexes are consi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342Y02B20/00
Inventor 刘淑娟赵方卿赵强陶鹏郑小康黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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