3,6-dioxocyclohexyl-1,4-diene-1,2-dinitrile derivative as well as preparation and application thereof
A technology of dioxo ring and derivatives is applied in the field of preparation and application of organic optoelectronic materials, which can solve the problems of poor film-forming property and poor stability, achieve easy operation, improve external quantum efficiency and luminous brightness, and facilitate doping effect of concentration
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[0040] The present invention also provides a preparation method of 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivatives, comprising the following steps:
[0041] (1) RCOOH reacts with potassium tert-butoxide to obtain RCOOK;
[0042] (2) RCOOK and 2,3-dichloro-5,6-dicyano-p-benzoquinone undergo a palladium-catalyzed decarboxylation cross-coupling reaction to obtain the 3,6-dioxocyclohexa-1,4-diene- 1,2-Dinitrile derivatives.
[0043] The 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile derivatives in the present invention, through the 3,6-dioxocyclohexa-1,4-diene-1 , 2-dinitrile is obtained by inserting an electron-withdrawing group R, which is used as a P-type dopant in the hole injection layer of OLED.
[0044] The invention also provides the application of the 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative in organic electroluminescent devices.
[0045] In some embodiments, the 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative is used as a P-type dopant for a...
Embodiment 1
[0051] Taking the 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative as shown in compound 1 as an example, the following synthetic route is adopted:
[0052]
[0053] Potassium 4-cyanobenzoate synthesis:
[0054] Add 4-cyanobenzoic acid (5g), potassium tert-butoxide (3.9g), and ethanol (40ml) into a 250ml beaker, stir at room temperature for 40min, filter with suction to get the upper layer solid, dry at 45°C for 2h to get 8.5 g (93%).
[0055] Synthesis of Compound 1:
[0056] Potassium 4-cyanobenzoate (2.5g), 2,3-dichloro-5,6-dicyano-p-benzoquinone (1g), Pd(OAC) 2 (0.04g), three (o-methylphenyl) phosphorus (0.1g) join in the flask of 50ml, replace N 2 Three times, inject 20ml of diethylene glycol dimethyl ether into it, stir at room temperature for 10min, raise the temperature to 140°C for 24h, distill off diethylene glycol dimethyl ether under reduced pressure, and pass through the column to obtain 0.08g (3.7%) of solid .
[0057] MS(APCI)(m / z):[M+H + ] calcd, 3...
Embodiment 2
[0059] Taking the 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative as shown in compound 4 as an example, the following synthetic route is adopted:
[0060]
[0061] Potassium 4-cyano-3,5-difluorobenzoate Preparation:
[0062] Add 4-cyano-3,5-difluorobenzoic acid (3.2g), potassium tert-butoxide (1.96g), and ethanol (30ml) into a 250ml beaker, stir at room temperature for 40min, and filter with suction to obtain the upper layer solid , dried at 45° C. for 2 h to yield 3.7 g (95.8%).
[0063] Synthesis of Compound 4:
[0064] Potassium 4-cyano-3,5-difluorobenzoate (3.7g), 2,3-dichloro-5,6-dicyano-p-benzoquinone (1.3g), Pd(OAC) 2 (0.04g), three (o-methylphenyl) phosphorus (0.2g) join in the flask of 50ml, replace N 2 Three times, inject 20ml of diethylene glycol dimethyl ether into it, stir at room temperature for 10min, raise the temperature to 140°C for 24h, distill off diethylene glycol dimethyl ether under reduced pressure, pass through the column to obtain 0.13g (5...
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