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Phosphinoxy red/orange thermally excited delayed fluorescent material, synthesis method and application

A technology of delayed fluorescence and phosphine red, which is applied in luminescent materials, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc., can solve the problems of concentration quenching, fast decay, and low efficiency of light-emitting devices , to improve efficiency, inhibit intermolecular interactions, and reduce quenching effects

Active Publication Date: 2019-04-05
JIANGSU FUXIN ELECTRONICS LIGHTING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the problem of concentration quenching caused by the large molecular polarity of the existing red / orange TADF materials and the problems of low efficiency and fast decay of electroluminescent devices, and provides a phosphine-based red / orange TADF material. Orange thermally excited delayed fluorescent material, synthesis method and application

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  • Phosphinoxy red/orange thermally excited delayed fluorescent material, synthesis method and application
  • Phosphinoxy red/orange thermally excited delayed fluorescent material, synthesis method and application
  • Phosphinoxy red/orange thermally excited delayed fluorescent material, synthesis method and application

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specific Embodiment approach 1

[0057] Specific embodiment 1: In this embodiment, the structural formula of phosphine red / orange photothermal excitation delay fluorescent material is as follows:

[0058] When X is carbazolyl, Y is , its structural formula is:

[0059] When X is 3,6-di-tert-butylcarbazolyl, Y is , its structural formula is:

[0060] When X is carbazolyl, Y is , its structural formula is:

[0061] When X is 3,6-di-tert-butylcarbazolyl, Y is , its structural formula is:

[0062] When X is carbazolyl, Y is , its structural formula is:

[0063] When X is 3,6-di-tert-butylcarbazolyl, Y is , its structural formula is:

specific Embodiment approach 2

[0064] Specific embodiment two: the synthetic method of phosphine red / orange photothermal excitation delayed fluorescent material described in specific embodiment one, the synthetic method is as follows:

[0065] 1. Mix 2~5mmol of carbazole or 3,6-di-tert-butylcarbazole, 1mmol of 3-bromo-4-fluorobenzaldehyde, 5~20ml of dimethyl sulfoxide and 2~5mmol of potassium carbonate , stirred and reacted at 150°C for 12-24 hours, then poured into ice water, filtered with suction, dissolved the obtained solid in benzene, added 5-10 mmol of ethylene glycol, 0.1-1 mmol of p-toluenesulfonic acid, and refluxed for 3- After cooling for 12 hours, extract with water and dichloromethane, combine the organic layers, remove the organic solvent after drying, and recrystallize with absolute ethanol to obtain 9-(2-bromo-4-(1,3-dioxolane- 2-yl)phenyl)-9H-carbazole or 9-(2-bromo-4-(1,3-dioxolan-2-yl)phenyl)-3,6-di-tert-butyl-9H - carbazole;

[0066] 2. Dissolve the product synthesized in Step 1 in tet...

specific Embodiment approach 3

[0068] Specific embodiment three: the difference between this embodiment and specific embodiment two is that in step one, 3 mmol of carbazole or 3,6-di-tert-butyl carbazole, 1 mmol of 3-bromo-4-fluorobenzaldehyde, 10 ml of Dimethyl sulfoxide and 4 mmol of potassium carbonate were mixed. Others are the same as the specific implementation.

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Abstract

A phosphinoxy red / orange photothermally excited delayed fluorescent material, a synthesis method and an application thereof relate to a thermally excited delayed fluorescent material, a synthetic method and an application thereof. The invention aims to solve the problems of concentration quenching caused by the large molecular polarity of the existing red / orange light TADF materials and low efficiency and fast decay of electroluminescent devices. The structural formula of this material is as follows: Synthetic method: prepare 9-(2-bromo-4-(1,3-dioxolane-2-yl)phenyl)-9H-carbazole or 9-(2-bromo-4- (1,3-dioxolane-2-yl)phenyl)-3,6-di-tert-butyl-9H-carbazole; preparation of 4-(9H-carbazole-9-yl)-3-(di phenylphosphinoxy)benzaldehyde or 4-(3,6-di-tert-butyl-9H-carbazol-9-yl)-3-(diphenylphosphinoxy)benzaldehyde; the final product is obtained. The material of the invention significantly improves the efficiency of the electroluminescent device, reduces the quenching effect, and enhances the stability of the efficiency of the electroluminescent device. The invention belongs to the field of preparation of fluorescent materials.

Description

technical field [0001] The invention relates to a heat-excited delayed fluorescent material, a synthesis method and an application thereof. Background technique [0002] Organic light-emitting diodes (Organic Light Emitting Diodes, OLEDs) are favored for their outstanding advantages such as ultra-light and ultra-thin, flexible and flexible, fast response, energy saving and environmental protection, and have become a new generation of flat panel display technology and lighting field. stand out. The traditional first-generation organic electroluminescent materials are fluorescent materials, because they only use singlet excitons to emit light, so the theoretical internal quantum efficiency can only reach 25%. Phosphorescent materials based on heavy metal complexes can simultaneously utilize singlet and triplet excitons to achieve 100% internal quantum efficiency, becoming the second generation of electroluminescent materials; however, the high cost of metal complexes is still...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/547C09K11/06H01L51/50
CPCC09K11/06C07F9/547C09K2211/1014C09K2211/1029C09K2211/1007C09K2211/1088H10K85/6574H10K85/6572H10K30/865
Inventor 韩春苗赵炳捷许辉
Owner JIANGSU FUXIN ELECTRONICS LIGHTING TECH
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