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Red-light thermally-induced delayed fluorescence material and preparation method thereof, and organic electroluminescent device

A technology of delayed fluorescence and fluorescent materials, which is applied in the field of luminescent materials, can solve the problems of unfavorable development of large-size OLED full-color display, strong intermolecular force, and low luminous efficiency, so as to suppress non-radiative transitions, improve luminous performance, and high The effect of luminous efficiency

Pending Publication Date: 2021-08-31
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of red-light TADF materials is relatively lagging behind, and the luminous efficiency is low, and materials that meet the requirements of saturated red light emission (λ em >600nm, and CIE x >0.6, CIE y <0.4) The number is relatively small, although red TADF molecules with device EQE close to 30% have been reported one after another, but the overall performance, especially the severe efficiency roll-off at high brightness, is still difficult to meet the needs of practical applications
[0004] At present, red light TADF materials are mainly small molecular compounds that form a twisted structure for (D) / acceptor (A), with linear D (donor)-A (acceptor), D-Ph-A or V-type D-A-D, D-Ph-A-Ph-D molecular structure, small molecular weight, strong intermolecular force, easy to aggregate, poor film-forming properties, high vacuum evaporation technology is often used in the production of devices, which is not conducive to large-size OLED full-color show development

Method used

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  • Red-light thermally-induced delayed fluorescence material and preparation method thereof, and organic electroluminescent device
  • Red-light thermally-induced delayed fluorescence material and preparation method thereof, and organic electroluminescent device
  • Red-light thermally-induced delayed fluorescence material and preparation method thereof, and organic electroluminescent device

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preparation example Construction

[0066] The present invention also provides a preparation method of the red light heat-induced delayed fluorescent material described in the above technical solution, comprising the following steps:

[0067] a) bromoindanone X undergoes an Aldol condensation reaction to form a tribromotriindene intermediate Y;

[0068] b) The tribromotrisindene intermediate Y reacts with aryl borate Z to form a multi-armed star precursor L;

[0069] c) The multi-armed star precursor L undergoes an oxidation reaction to form a red photothermally induced delayed fluorescent material represented by formula (I);

[0070]

[0071] In the formula Z, the aryl Ar- is the unit.

[0072] Regarding step a): bromoindanone X undergoes an Aldol condensation reaction to form a tribromoindan intermediate Y.

[0073] In the present invention, the bromoindanone is shown in formula X:

[0074]

[0075] Preferably, the bromoindanone X is 5-bromoindanone or 6-bromoindanone. When 6-bromoindanone is used ...

preparation example 1

[0116] Intermediate Preparation Example 1: Preparation of 3,8,13-tribromotripolyindene intermediate (i.e. 3,8,13-substituted type, i.e. Y-M) synthetic route is as follows:

[0117]

[0118] The preparation process is as follows:

[0119] Dissolve 6-bromoindanone (3.0g, 14.2mmol), p-toluenesulfonic acid monohydrate (9.5g, 49.9mmol) in dry o-dichlorobenzene (45mL), add propionic acid (3.7mL) under stirring at room temperature ), the system was heated to 135°C for reflux reaction for 72h. After the reaction, cool to room temperature, pour the reaction solution into 100mL methanol, and adjust the pH of the system to neutral with 1M NaOH aqueous solution. At this time, a large amount of precipitates will precipitate out, filter, and wash the filter cake with methanol and ethanol in sequence to obtain the intermediate Body Y-M, light yellow solid 2.3g, yield 84%.

preparation example 2

[0120] Intermediate Preparation Example 2: Preparation of 2,7,12-tribromotripolyindene intermediate (i.e. 2,7,12-substituted type, denoted as Y-N)

[0121] The synthetic route is as follows:

[0122]

[0123] The preparation process is as follows:

[0124] According to the preparation process of Intermediate Preparation Example 1, the difference is that the raw material 6-bromoindanone is replaced by 5-bromoindanone. As a result, the product intermediate Y-N was obtained as a light yellow solid with a yield of 81%.

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Abstract

The invention provides a red-light thermally-induced delayed fluorescence material and a preparation method thereof, and an organic electroluminescent device. The red-light thermally-induced delayed fluorescence material provided by the invention is a red-light thermally-induced delayed fluorescence material with a multi-arm star-shaped structure as shown in a formula (I), the band gap is narrow, and the energy level difference between a first excited singlet state and a first excited triplet state is small, so that the compound has a red-light thermally-induced delayed fluorescence emission property. Moreover, a rigid truxene ketone acceptor unit contains three carbonyl groups, the reverse intersystem crossing rate of the electroluminescent material based on a truxene ketone derivative is favorably improved by utilizing the high intersystem crossing rate of the carbonyl groups, and meanwhile, the rigid plane structure is favorable for inhibiting non-radiative transition and improving the luminescent property of the material. Meanwhile, the truxene derivative as shown in the formula (I) has a multi-arm star-shaped structure, so that the weakening of intermolecular interaction is facilitated, the solubility of the material is improved, and a solution processing device is facilitated.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to a red light thermally induced delayed fluorescent material, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of light weight, good flexibility, wide viewing angle, high contrast and brightness, low energy consumption, fast response, and self-luminescence. They have great application potential in flat panel displays, smartphones, and solid-state lighting. Luminescent materials are the key factors affecting the luminous performance of OLEDs. Conventional fluorescent materials are limited to only 25% exciton utilization, resulting in low luminous efficiency. Phosphorescent complexes (i.e., phosphorescent materials) containing metals such as iridium (III), platinum (II) or osmium (II) strengthen intramolecular intersystem crossing through spin-orbit coupling, and realiz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D209/86C07C225/22C07D519/00C07C221/00C07C209/68C07C211/54C09K11/06H01L51/50
CPCC07D219/02C07D209/86C07C225/22C07D519/00C07C221/00C07C209/68C07C211/54C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C07C2603/54H10K85/624H10K85/631H10K85/6572H10K50/12
Inventor 战宏梅李怡潼姚兵李阔飞邓浩程延祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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