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Preparation and application of a thermally activated delayed fluorescence OLED based on a seven-membered ring diimide acceptor

A heat-activated delay and cyclic imide technology, which is applied in the fields of luminescent materials, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve the problems of restricting the development of high-efficiency delayed fluorescent materials, low device efficiency, and single types, etc., and achieve good results. The effect of industrialization prospect, good performance and good application effect

Active Publication Date: 2022-07-05
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the correlation between the material structure and its photophysical properties and device efficiency is still unclear, which limits the development of high-efficiency delayed fluorescence materials, resulting in a single type of existing TADF materials and low device efficiency, which cannot meet the requirements of high-efficiency organic light-emitting diodes.

Method used

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  • Preparation and application of a thermally activated delayed fluorescence OLED based on a seven-membered ring diimide acceptor
  • Preparation and application of a thermally activated delayed fluorescence OLED based on a seven-membered ring diimide acceptor
  • Preparation and application of a thermally activated delayed fluorescence OLED based on a seven-membered ring diimide acceptor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of Intermediate B1

[0034]

[0035] A magnetic stirring bar was placed in a 250mL there-necked flask, p-bromobenzoic acid (10g, 50mmol), ruthenium trichloride (II) (518.6mg, 2.5mmol), 1,8-diazabicyclo[5.4.0 ] Undec-7-ene (7.2 mL, 50 mmol), replaced oxygen for more than three times, added 60 mL of ethylene glycol dimethyl ether, heated to 110° C. and reacted for 30 hours. After the reaction was completed and cooled to room temperature, potassium carbonate (20.7 g, 150 mmol), methyl iodide (9.5 mL, 150 mmol) were added, and after stirring at room temperature for 4 hours, the solution was filtered under reduced pressure, and the solvent and low boilers were evaporated in vacuo. The crude product was filtered through a column. Purified by chromatography, the eluent was petroleum ether:ethyl acetate=10:1. The target intermediate B1 was obtained in the form of 5.56 g of white solids, and the yield was 52%.

[0036] High-resolution mass spectrometry, ESI sour...

Embodiment 2

[0052] Preparation of Intermediate D1

[0053]

[0054] A magnetic stirring bar was placed in a 250mL there-necked flask, p-bromobenzoic acid (10g, 50mmol), benzoic acid (1.525g, 12.5mmol), dichloro (p-methylcumene) ruthenium (II) dimer were added (736mg, 1.25mmol), copper oxide (1.5g, 18.75mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (9.0mL, 62.5mmol), replaced oxygen more than three times , 60 mL of anhydrous 1,4-dioxane was added, the temperature was raised to 110° C. and the reaction was performed for 30 hours. After the reaction was completed and cooled to room temperature, potassium carbonate (8.625 g, 62.5 mmol), methyl iodide (3.96 mL, 62.5 mmol) were added, stirred at room temperature for 4 hours, filtered under reduced pressure, the solvent and low boilers were evaporated in vacuo, and the crude product was Purified by column chromatography, the eluent is petroleum ether:ethyl acetate=10:1. The target intermediate D1 was obtained in the form of 1.74 g of a white so...

Embodiment 3

[0071] The preparation of compound C4 was similar to that of compound C1, except that 4-(9,9-dimethyl-9,10dihydroacridine)phenylboronic acid was used instead of 9,10-dihydro-9,9-di Methyl acridine was prepared to obtain intermediate E2, and then compound C4 was prepared as a pale yellow solid with a total yield of 37%.

[0072] High-resolution mass spectrometry, ESI source, positive ion mode, molecular formula [C 66 H 55 N 3 O 2 +Na] + , the theoretical value is 944.4186, and the measured value is 944.4182.

[0073] Preparation of Intermediate E2

[0074]

[0075] A magnetic stirring bar was placed in a 25mL high-pressure tube, Intermediate B1 (214mg, 0.5mmol), 4-(9,9-dimethyl-9,10dihydroacridine)phenylboronic acid (362mg, 1.1mmol) were added, Tetrakis(triphenylphosphine)palladium (57.8 mg, 0.05 mmol), potassium carbonate (276 mg, 2.0 mmol), nitrogen was replaced for more than three times, 5.0 mL of degassed tetrahydrofuran was added, and the reaction was refluxed for...

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Abstract

The invention discloses a thermally activated delayed fluorescence OLED material based on a seven-membered ring diimide acceptor and an application thereof, belonging to the technical field of organic optoelectronic materials. It has the structures shown in formula I and formula II: the present invention also discloses the application of the above-mentioned OLED material. The OLED material of the present invention is a kind of organic small molecular compound which is characterized by seven-membered ring diimide and is formed by connecting power supply groups through aromatic groups, and has suitable molecular energy level, high decomposition temperature and glass transition temperature, and has obvious thermally activated delayed fluorescence (TADF) properties and aggregation-induced fluorescence enhancement (AIE) properties. in the field of luminescence.

Description

technical field [0001] The invention relates to a thermally activated delayed fluorescence OLED material with a seven-membered ring diimide as the core and an application thereof, belonging to the technical field of organic optoelectronic materials. Background technique [0002] At present, products based on OLED display technology have been industrialized. Compared with liquid crystal display technology, OLED display technology has many advantages such as self-luminescence, no radiation, light weight, thin thickness, wide viewing angle, wide color gamut, color stability, fast response speed, strong environmental adaptability, and flexible display. Therefore, OLED display technology is gaining more and more attention and corresponding technical input. [0003] The basic structural unit of OLED display is OLED device, which can be divided into two types: fluorescent device and phosphorescent device according to different light-emitting mechanisms. As the first generation of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D413/14C07D403/14C07D401/04C07D403/04C07D413/04C07D417/04C07D223/18C07D417/14C07D401/10C07D403/10C07D413/10C07D417/10C09K11/06H01L51/50H01L51/54
CPCC07D401/14C07D413/14C07D403/14C07D401/04C07D403/04C07D413/04C07D417/04C07D223/18C07D417/14C07D401/10C07D403/10C07D413/10C07D417/10C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1014C09K2211/1022H10K85/631H10K85/636H10K85/657H10K85/6572H10K50/11Y02E10/549
Inventor 游劲松黄珍梅宾正杨
Owner SICHUAN UNIV
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