A kind of 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile derivative, its preparation and application

A technology of dioxo rings and derivatives, which is applied in the preparation and application of organic photoelectric materials, can solve the problems of poor film formation and poor stability, achieve easy operation, improve external quantum efficiency and luminous brightness, and solve the problem of organic film Effect of Layer Pollution

Active Publication Date: 2021-03-26
HUAZHONG UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Aiming at the above deficiencies or improvement needs of the prior art, the present invention provides a 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative, its preparation and application, through The key chemical structure of the 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative was improved, a strong electron-withdrawing group was introduced, and the 3,6-dioxo Substituted cyclohexa-1,4-diene-1,2-dinitrile derivatives are used as P-type dopants in organic electroluminescent devices, which greatly improves the hole density on the hole transport layer HOMO. Concentration, the mobility of holes is increased, which can effectively improve device efficiency, reduce efficiency roll-off and turn-on voltage, and the derivative has good thermal stability, thus solving the problem of P-type dopant in the prior art in device preparation Poor stability in the application and technical problems such as crystallization and poor film formation in the application

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  • A kind of 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile derivative, its preparation and application
  • A kind of 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile derivative, its preparation and application
  • A kind of 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile derivative, its preparation and application

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preparation example Construction

[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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Abstract

The invention belongs to the technical field of preparation and application of organic photoelectric materials, and more specifically relates to a 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative, its preparation and application. By improving the key chemical structure of the 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative, a strong electron-withdrawing group was introduced, and the 3,6-diene Oxycyclohexyl-1,4-diene-1,2-dinitrile derivatives are used as P-type dopant materials in organic electroluminescent devices, which greatly improves the hole transport layer HOMO. Hole concentration increases the mobility of holes, which can effectively improve device efficiency, reduce efficiency roll-off and turn-on voltage, and this derivative has good thermal stability, thus solving the problem of P-type dopants in the prior art. There are technical problems such as poor stability in the preparation and crystallization and poor film-forming properties in the application.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of organic photoelectric materials, and more specifically relates to a 3,6-dioxocyclohexa-1,4-diene-1,2-dinitrile derivative, its preparation and application. Background technique [0002] With the progress of the times, low-carbon environmental protection has increasingly become the focus of people's attention. Therefore, how to save energy has also begun to attract more and more people's attention. Organic Light Emitting Diode (OLED) is an emerging technology in recent years to meet the needs of the times. With its unique characteristics such as wide viewing angle, low energy consumption, self-illumination, high brightness, wide application environment, and flexible products, OLED has a wide range of applications in white lighting and flat panel display. [0003] The organic light-emitting diode (OLED) electrons are injected through the cathode, and holes are injected throug...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07C255/56C07C253/30C09K11/06H01L51/50H01L51/54
CPCC07C255/56C09K11/06C09K2211/1007H10K85/60H10K50/155
Inventor王磊李先杰郭闰达庄少卿
OwnerHUAZHONG UNIV OF SCI & TECH