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Compound comprising 9,9-dimethyl-9.10-dihydracridine and preparation and application thereof

A technology of dihydroacridine and dimethyl, which is applied in the application field of organic electroluminescent materials, can solve problems hindering development and practical application, and achieve easy operation, good thermal stability, high product yield and purity Effect

Active Publication Date: 2018-02-23
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most TADF molecules have several challenges that seriously hinder their development and practical applications

Method used

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  • Compound comprising 9,9-dimethyl-9.10-dihydracridine and preparation and application thereof
  • Compound comprising 9,9-dimethyl-9.10-dihydracridine and preparation and application thereof
  • Compound comprising 9,9-dimethyl-9.10-dihydracridine and preparation and application thereof

Examples

Experimental program
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Embodiment 1

[0031] Example 1. Preparation of (3,5-biscarbazole-9-phenyl)-(4-(9,9-dimethyl-9-acridine-10-)-phenyl)-methanone, steps as follows:

[0032](1) Synthesis and Characterization of 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole)

[0033] Carbazole (8.35g, 50mmol), 1,3,5-tribromobenzene (7.85g, 25mmol), CuI (0.48g, 2.5mmol), 18-crown-6 (1.0g, 3.8mmol), carbonic acid Potassium (18.3 g, 75 mmol) was dissolved in o-dichlorobenzene (100 mL), heated to 180° C. and stirred for 24 h under nitrogen. After cooling to room temperature, saturated (NH 4 ) 2 CO 3 The solution was quenched, and the mixture was extracted with chloroform; the organic layers were combined, washed three times with distilled water, and dried over anhydrous magnesium sulfate. Then the solvent was spin-dried to obtain the crude product, which was separated by column chromatography to obtain the white solid compound 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole) (6.0 g, yield 50 %). 1 H NMR (600MHz, CDCl 3 ): δ8.14...

Embodiment 2

[0040] Embodiment 2. Structure, preparation and performance of organic electroluminescent devices:

[0041] We have prepared a non-doped organic electroluminescence device, the structure of the device is: ITO / HATCN, thickness 20nm / TAPC, thickness 30nm / the said 9,9-dimethyl-9,10-dihydro The compound with acridine structure has a thickness of 25nm / TmPyPB, a thickness of 40nm / LiF, a thickness of 1nm / Al, and a thickness of 150nm; the structures of three doped organic electroluminescent devices are: ITO / HATCN, a thickness of 20nm / TAPC, a thickness of 30nm / all The compound containing 9,9-dimethyl-9,10-dihydroacridine structure (mass fraction 6%, 10%, 20%): CBP, thickness 25nm / TmPyPB, thickness 40nm / LiF, thickness 1nm / Al, thickness 150nm. Among them, HATCN is used as a hole injection layer, and TAPC is used as a hole transport layer; (3,5-biscarbazole-9-phenyl)-(4-(9,9-dimethyl-9-acridine-10- )-phenyl)-methanone (compound DCPDAPM) as the light emitting layer; TmPyPB as the electro...

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Abstract

The invention provides a compound comprising 9,9-dimethyl-9,10-dihydracridine and preparation and an application of the compound. The name of the compound is (3,5-dicarbazyl-9-phenyl)-(4-(9,9-dimethyl-9H-acridine-10)-phenyl)-ketone. A preparation method comprises the following steps: firstly preparing 9,9'-(5-bromine-1,3-phenylene)di(9H-carbazole); enabling the 9,9'-(5-bromine-1,3-phenylene)di(9H-carbazole), t-BuLi, 4-bromobenzaldehyde and PCC to react to obtain (3,5-dicarbazyl-9-phenyl)-(4-bromophenylacetone)-ketone; and finally enabling the (3,5-dicarbazyl-9-phenyl)-(4-bromophenylacetone)-ketone and the 9,10-dihydro-9,9-dimethyl acridine to react to obtain the (3,5-dicarbazyl-9-phenyl)-(4-(9,9-dimethyl-9H-acridine-10)-phenyl)-ketone. The compound is excellent in thermal stability, electrochemical property, charge transfer performance and luminescence property, and can be used as a green organic electroluminescent material.

Description

technical field [0001] The present invention relates to a heterocyclic compound containing carbon, hydrogen, oxygen and nitrogen, specifically a benzophenone-centered compound containing a carbazole group and a 9,9-dimethyl-9,10-dihydroacridinyl group The preparation method of the compound of the group, and the application of the compound as an organic electroluminescence material. Background technique [0002] Over the past few decades, significant progress has been made in the optimization of solid-state organic fluorescent materials for the fabrication of high-efficiency OLEDs. However, the maximum internal quantum efficiency (IQE) of classical OLEDs is limited to 25%. Such a small IQE greatly limits the development of OLEDs. In 2012, Adachi et al. fabricated an undoped OLED device by using a fluorescent light-emitting material with thermally activated delayed fluorescence (TADF) properties, and its external quantum efficiency (EQE) reached 19.3%. According to the lumi...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C09K2211/1029C09K2211/1007H10K85/6572H10K50/11H10K2102/00H10K2102/301
Inventor 董秀清施和平赵耀东王淑娟张鑫磊程芳琴
Owner SHANXI UNIV
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