Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof

A luminescent and electromechanical technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of immature blue light-emitting devices, low device life and low efficiency, and achieve high thermal stability and photoelectric performance. Aggregation, not easy to crystallize

Active Publication Date: 2017-03-29
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to realize full-color display, light-emitting devices of red, green, and blue colors are required respectively. Compared wi

Method used

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  • Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof
  • Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof
  • Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0043] Preparation of Example 1 Intermediate 1

[0044] Preparation of Intermediate 1-1: In a 500mL three-necked flask, add methyl 5-bromo-2-iodocarboxylate (34.1g, 0.10mol), dibenzofuran-4-boronic acid (23.3g, 0.11mmol), carbonic acid Potassium (27.6g, 0.20mol), 82.8g water, Pd (PPh 3 ) 4 (578 mg, 0.5 mmol), toluene (150 mL), absolute ethanol (50 mL), N 2Protection, warming up to reflux, holding the reaction for 4 hours, stopping the reaction, cooling to 25°C, separating the liquids, collecting the organic phase, washing with water until neutral, and removing the solvent from the organic phase under reduced pressure to obtain the crude intermediate 1-1, the crude product is not. After purification, it is directly put into the next reaction.

[0045] Preparation of Intermediate 1-2: In a 500mL three-necked flask, add Intermediate 1-1 (38.1g, 0.10mol), sodium hydroxide (12.0g, 0.30mol), absolute ethanol (200mL), N 2 Protect, heat up to reflux, keep reacting for 3 hours, coo...

Example Embodiment

[0050] The preparation of embodiment 2 compound C02

[0051]

[0052] In a 250mL there-necked flask, add Intermediate 1 (6.14g, 10mmol), 1-naphthaleneboronic acid (3.78g, 22mmol), potassium carbonate (4.15g, 30mmol), Pd (PPh) 3 ) 4 (58 mg, 0.05 mmol), mixed with xylenes (80 mL), N 2 Protect, heat up to reflux, keep the reaction for 8 hours, stop the reaction, cool down to 25 ℃, add 50 mL of deionized water, stir for 5 min, separate liquids, collect the organic phase, remove the solvent, and obtain CO2 crude product, which is purified by silica gel column chromatography , the target compound C01 was obtained, the HPLC purity was 99.83%, and the yield was 82.65%. High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 55 H 32 O, theoretical value 708.2453, test value 708.2456. Elemental Analysis (C 55 H 32 O), theoretical value C: 93.19, H: 4.55, O: 2.26, observed value C: 93.17, H: 4.56, O: 2.27.

Example Embodiment

[0053] The preparation of embodiment 3 compound C04

[0054] Referring to Example 2, the raw materials are intermediate 1 and 4-biphenylboronic acid to obtain a C04 compound with a HPLC purity of 99.95% and a yield of 78.52%. High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 59 H 36 O, theoretical value 760.2766, test value 760.2761. Elemental Analysis (C 59 H 36 O), theoretical value C: 93.13, H: 4.77, O: 2.10, observed value C: 93.11, H: 4.76, O: 2.13.

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Abstract

The invention discloses an organic electroluminescent material with a dibenzofuran structure and a preparation method and application thereof. The organic electroluminescent material has the following molecular structure (the structure is shown in the description). The novel spiro-type micromolecular organic electroluminescent material with the dibenzofuran structure has the advantages that molecules are not prone to be crystallized or aggregated, and the good film forming property is achieved, has the suitable HOMO and LUMO energy levels and can be applied in organic electroluminescent devices by serving as a luminescent layer, and therefore the organic electroluminescent devices achieve the high thermal stability and photoelectric property.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent material with an oxyfluorene structure, a preparation method and an application thereof. Background technique [0002] Organic electroluminescent diodes (OLEDs) were produced in the 1980s. They have many advantages such as self-illumination, wide viewing angle, fast response speed, and flexible display, which make them the most favorable competitors for the next generation of flat panel display technology. , has received great attention from people, and after more than 20 years of development, the technology has gradually matured. [0003] At present, organic electroluminescent technology is mainly used in two fields, namely full-color display and white lighting. Commodities based on OLED display technology have gradually realized industrialization, for example, in products such as smart phones and curved TVs. , this technique has...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D307/77C07D405/14C07D307/91C07D405/04H01L51/54
CPCC09K11/06C07D307/77C07D307/91C07D405/04C07D405/14C09K2211/1029C09K2211/1088H10K85/622H10K85/626H10K85/615H10K85/6574H10K85/6572H10K50/11
Inventor 高自良张成新石宇李庆胡葆华孟凡民
Owner VALIANT CO LTD
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