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Organic electroluminescence compound with diphosphopentadiene condensed ring and synthesis method of compound

A technology of heterocyclopentadiene and compound, which is applied in the field of organic electroluminescent materials to achieve the effect of reducing LUMO orbital, improving electron injection and transmission capability, and simple route

Inactive Publication Date: 2018-09-21
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there have been no relevant research reports on this type of compound

Method used

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  • Organic electroluminescence compound with diphosphopentadiene condensed ring and synthesis method of compound
  • Organic electroluminescence compound with diphosphopentadiene condensed ring and synthesis method of compound
  • Organic electroluminescence compound with diphosphopentadiene condensed ring and synthesis method of compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of embodiment 1 compound Ia

[0027] (1) Synthesis of compound III

[0028]

[0029] Under nitrogen protection, add 4.85g of compound II, 2.50g of trimethylsilylacetylene, 50ml of triethylamine, 100mg of cuprous iodide, 150mg of dichlorobis(triphenylphosphine)palladium, close the reaction system, and stir overnight at room temperature. The reaction process was detected by gas phase. After the reaction was completed, triethylamine was distilled off under reduced pressure, and the column was eluted with n-hexane eluent, and spin-dried to obtain the crude product. The pure product was obtained by silica gel column chromatography, 3.2 g of white solid, and the yield was 80%. .

[0030] 1 H NMR (300MHz, CDCl 3 )δ=0.08(s,18H),7.65(s,2H).

[0031] (2) Synthesis of compound IV

[0032]

[0033] Under the protection of nitrogen, add 4.25g of compound III, then add 20ml of anhydrous tetrahydrofuran, 20ml of anhydrous ether, cool the system to -75°C ~ -80°...

Embodiment 2

[0047] The synthesis of embodiment 2 compound 1b

[0048]

[0049] Under the protection of nitrogen, add 3.7g of compound V to the reaction flask, then add 6.2g of compound VIb, then add 20ml of dichloroethane, 2.5g of silver hexafluorophosphate, 5g of o-tetrachlorobenzoquinone, 0.2g of palladium acetate, 70-80 ℃ reflux reaction overnight, and the reaction system was processed to obtain the final product Compound I. The pure product was obtained by silica gel column chromatography as a green solid. The cis structure was 5.9g, and the yield was 85%, and the trans structure was 5.7g, and the yield was 82%.

[0050] Shun 31 P{1H}NMR (121MHz, CDCl 3 )δ=40.7; 1 H NMR (300MHz, CDCl 3 )δ=6.90-7.16(m,4H),7.22-7.37(m,4H),7.50-7.78(m,16H).

[0051] opposite 31 P{1H}NMR (121MHz, CDCl 3 )δ=39.1; 1 H NMR (300MHz, CDCl 3 )δ=6.80-7.06(m,4H),7.25-7.39(m,4H),7.45-7.50(m,10H),7.50-7.78(m,6H).

[0052] VIb was synthesized by the method of Via compound, replacing 2,2'-dibromobipheny...

Embodiment 3

[0053] The synthesis of embodiment 3 compound Ic

[0054]

[0055] Add 6.7g of compound Ia (cis) to the reaction flask, then add 20ml of anhydrous toluene, 15.0g of Lawson's reagent, react overnight at 85-95°C, and obtain pure product by silica gel column chromatography, yellow solid cis 5.8g, yield 83 %, trans 6.3g, yield 89%.

[0056] Shun 31 P{1H}NMR (121MHz, CDCl 3 )δ=45.0; 1 H NMR (300MHz, CDCl 3 )δ=7.30-7.52(m,6H),7.70-7.72(m,2H),7.67-7.83(m,12H),8.19-8.22(m,4H),8.78-8.92(m,4H).

[0057] opposite 31 P{1H}NMR (121MHz, CDCl 3 )δ=45.9; 1 H NMR (300MHz, CDCl 3 )δ=7.23-7.30(m,2H),7.31-7.53(m,4H),7.67-7.78(m,14H),8.19-8.22(m,4H),8.80-8.95(m,4H).

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Abstract

The invention discloses an organic electroluminescence compound with a diphosphopentadiene condensed ring and a synthesis method of the compound, and belongs to organophosphorus electroluminescence materials. The compound has a structure general formula as shown in a formula (I), wherein E is O or S, and a pi-conjugated group is phenyl or thiophene and the like. The compound can serve as a luminescent layer of an organic electroluminescence device to be applied to electroluminescence devices, luminescence properties of the device can be effectively changed by simply and chemically modifying phosphorus atoms and changing the pi-conjugated group, adjustment and control from blue light to yellow light are achieved, the compound is good in heat stability, natures of cis-trans-isomer devices are almost indistinguishable, the cis-trans-isomer devices has excellent charge injection and transmitting capacity, and the efficiency and the service lives of the corresponding organic electroluminescence devices can be remarkably improved.

Description

technical field [0001] The present invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent compound containing a bisphosphole heterocyclic ring, in particular to an organic electroluminescent compound containing a bisphosphole condensed ring, a synthesis method and its application . Background technique [0002] Organic electroluminescent devices have self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response, wide temperature range, low driving voltage, flexible, bendable and transparent display panels, and environmental friendliness, etc. With unique advantages, it can be applied to flat panel displays and new generation lighting, and can also be used as a backlight source for LCDs. Organic electroluminescent devices have been widely used in industry, such as screens for cameras and mobile phones. However, there are still some problems in the organic m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568C09K11/06
CPCC07F9/65685C09K11/06C09K2211/1007C09K2211/1092C09K2211/1096
Inventor 周洋赵永德代本才刘长春王兰天张豫黎柴存才陈杰英
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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