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Red-light metal complex and organic electroluminescent device thereof

A technology of metal complexes and red light, applied in the direction of electric solid devices, electrical components, luminescent materials, etc., to achieve the effects of reducing interaction force, reducing band gap, high luminous efficiency and power efficiency

Active Publication Date: 2017-10-10
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the luminous efficiency of the electroluminescent device of the dendritic phosphorescent material with the green-light metal iridium complex as the luminescent core can reach 53.2cd / A; but the efficiency of the electroluminescent device with the red-light metal iridium complex as the luminescent core Then only reach 13.2cd / A

Method used

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  • Red-light metal complex and organic electroluminescent device thereof
  • Red-light metal complex and organic electroluminescent device thereof
  • Red-light metal complex and organic electroluminescent device thereof

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preparation example Construction

[0061] The present invention provides a method for preparing a red light metal complex as shown in formula (I), comprising:

[0062] The compound of formula (II) structure is reacted with iridium chloride trihydrate to obtain an intermediate;

[0063] The intermediate is reacted with acetylacetone to obtain the red light metal complex shown in formula (I);

[0064] or

[0065] The compound of formula (II) structure is reacted with iridium chloride trihydrate to obtain an intermediate;

[0066] reacting the intermediate with the compound of formula (II) to obtain the red light metal complex shown in formula (I);

[0067]

[0068] Among them, R 2 independently selected from C1-C10 alkyl, C6-C25 aryl, and C6-C25 heterocyclic aryl; Ar is C6-C30 heterocyclic aryl.

[0069] The present invention does not limit the source of iridium chloride trihydrate, which may be commercially available.

[0070] The present invention does not limit the source of the compound of formula (II...

Embodiment 1

[0139]

[0140] Under argon protection, compound (1) (1.56g, 5mmol), 4-iodotriphenylamine (4.22g, 11.39mmol), cuprous chloride (0.20g, 2mmol), o-phenanthro Phenyl (0.79g, 4mmol), potassium hydroxide (2.24g, 40mmol) and p-xylene (50mL), stirred vigorously, heated to reflux for 36 hours. After the reaction, cool to room temperature, extract with ethyl acetate, separate the layers, wash the organic phase three times with water, dry the organic phase with anhydrous sodium sulfate, filter the organic phase, spin dry, and use dichloromethane / petroleum ether as the eluent The reagent was separated by silica gel column chromatography, and after drying, a light yellow solid was obtained with a yield of 45%. After NMR identification, the results are as follows: 1 HNMR(400MHz,DMSO)[ppm]:δ7.75(s,1H),7.73(s,1H),7.67(s,1H),7.65(s,1H),7.61(d,J=1.7Hz,1H ),7.48(dd,J=8.1,1.9Hz,1H),7.32–7.25(m,8H),7.08–6.95(m,20H),1.97–1.86(m,4H),0.27(t,J=7.3 Hz,8H). 13 C NMR (101MHz, CDCl 3 )[ppm]:δ152....

Embodiment 2

[0142] Example 2 Ligand DTPAA-Flpy-CF 3 Synthesis

[0143] Under argon protection, 2-chloro-5-trifluoromethylpyridine (0.44g, 2.44mmol), compound (3) (2.34g), Pd 2 (dba) 3 (0.11g, 0.12mmol), s-phos (0.25g, 0.61mmol) and 2M potassium carbonate solution (10mL) were added to 80mL of toluene, heated to reflux, and reacted for 24 hours. After the reaction, it was extracted with ethyl acetate, separated, washed with water until neutral, and dried over anhydrous sodium sulfate. After filtration and spin-drying, silica gel column chromatography was performed using petroleum ether / dichloromethane as the eluent, and a yellow solid was obtained after drying with a yield of 51%. After NMR identification, the results are as follows: 1 H NMR(400MHz,DMSO)[ppm]:δ9.04(s,1H),8.27(s,2H),8.21(s,1H),8.19–8.10(m,1H),7.86(d,J=8.0 Hz,1H),7.82(s,1H),7.36–7.23(m,8H),7.14–6.92(m,20H),6.52–6.47(m,1H),5.75(s,1H),0.86(s, 4H), 0.31(t, J=7.1Hz, 6H). 13 C NMR (101MHz, C 6 D. 6 )[ppm]:δ160.87,152.47,1...

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Abstract

The invention provides a red-light metal complex shown as a formula (I). In the formula, m is 2 and n is 1 or m is 3 and n is 0; R1 is independently selected from C1 to C10 alkyl, C1 to C10 substituted alkyl and C6 to C10 aryl; R2 is independently selected from C1 to C10 alkyl, C6 to C25 aryl and C6 to C25 heterocyclic aryl; Ar is C6 to C30 heterocyclic aryl. According to the red-light metal complex provided by the invention, an aromatic group is connected with fluorene to form a main group; meanwhile, triphenylamine is used as an end-capping group; the main group and the end-capping group have a synergistic effect and a stereo-hindrance effect of the triphenylamine is utilized, so that the mutual acting force between dye molecules is reduced and a self-quenching phenomenon of triple-state excitons in a solid-state film is reduced; meanwhile, the HOMO energy grade is improved by utilizing a strong electron donating effect, so that a band gap is reduced and red shift of a light spectrum is realized. A red-light to deep red-light phosphorescent iridium complex provided by the invention has relatively good dissolubility in a common solvent and solution machining type devices are easy to prepare; an organic electroluminescent device prepared by the red-light metal complex has relatively high luminous efficiency and power efficiency.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a red light metal complex and an organic electroluminescence device. Background technique [0002] Organic light-emitting diodes (Organic Light-Emitting Diodes, OLEDs) are driven by low-voltage DC, low energy consumption, easy to realize large-area flexible display, active light emission, fast response, low cost, etc., and are favored by academia and industry. Widely concerned, some products have been successfully industrialized and are considered to be the most promising next-generation display and lighting technologies. [0003] According to the different luminescent principles, organic electroluminescent materials can be divided into two categories: fluorescence and phosphorescence. Since phosphorescent materials can simultaneously utilize singlet and triplet excitons, the internal quantum efficiency of the device can theoretically reach 100%. Therefore, ...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342
Inventor 张保华刘雪景谢志元吴江
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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