Phosphonooxy-modified dipyridophenazine-based red/near-infrared thermally excited delayed fluorescent material, and synthesis method and application thereof

A near-infrared thermal and delayed fluorescence technology, 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, low efficiency of light-emitting devices, fast decay, etc.

Active Publication Date: 2019-09-27
HEILONGJIANG UNIV
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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 technical problems of existing red / near-infrared TADF materials such as concentration quenching caused by high molecular polarity and low efficiency and fast decay of electroluminescent devices, and provides a phosphine-oxy group-modified Dipyridophenazine-based red light / near-infrared thermally excited delayed fluorescence material, synthesis method and application thereof

Method used

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  • Phosphonooxy-modified dipyridophenazine-based red/near-infrared thermally excited delayed fluorescent material, and synthesis method and application thereof
  • Phosphonooxy-modified dipyridophenazine-based red/near-infrared thermally excited delayed fluorescent material, and synthesis method and application thereof
  • Phosphonooxy-modified dipyridophenazine-based red/near-infrared thermally excited delayed fluorescent material, and synthesis method and application thereof

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Experimental program
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specific Embodiment approach 1

[0068] Specific Embodiment 1: The structural formula of the dipyridoxphenazinyl red light / near-infrared thermally excited delayed fluorescent material modified with phosphine groups in this embodiment is as follows: where X is hydrogen or Y is hydrogen,

[0069] Z is hydrogen, W is hydrogen or M is hydrogen or V is hydrogen or

[0070] N is hydrogen or U is hydrogen or

[0071] When W, Y, Z, M, V are hydrogen, X is N and U are , its structural formula is:

[0072] When W, Z, M, V are hydrogen, X, Y are N and U are , its structural formula is:

[0073] When X, Y, Z, M, V are hydrogen, W is N and U are , its structural formula is:

[0074] When X, Y, M, V are hydrogen, W, Z are N and U are , its structural formula is:

[0075] When W, Z, M, V are hydrogen, X is Y, N, U are , its structural formula is:

[0076] When X, Y, M, V are hydrogen, W is Z, N, U are , its structural formula is:

[0077] When W, Y, Z, N, U are hydr...

specific Embodiment approach 2

[0083] Specific embodiment 2: The synthesis method of the dipyridoxphenazinyl red light / near-infrared thermal excitation delayed fluorescent material modified by the phosphine group described in the specific embodiment 1 is carried out according to the following steps:

[0084] 1. Take 0.8~1.2mmol of 2,9-dibromophenanthroline-5,6-dione or 3,8-dibromophenanthroline-5,6-dione, 1mmol of the reaction precursor and ethanol 5 Mix ~10ml, react at 80°C for 48h, extract with water and dichloromethane, combine the organic layers, dry, and purify by column chromatography using a mixed solvent of dichloromethane and ethyl acetate as eluent to obtain the intermediate;

[0085] 2. Take 1 mmol of the intermediate synthesized in step 1, 0.05 mmol of palladium acetate, 1 to 10 mmol of sodium acetate, 1 mmol of diphenylphosphine and 5 to 10 ml of N,N dimethylformamide, mix them at 150°C for 48 hours, and add 5 mmol h 2 o 2 Oxidation, extraction with water and dichloromethane, combined organic...

specific Embodiment approach 3

[0086] Specific embodiment 3: The difference between this embodiment and specific embodiment 2 is that the reaction precursor described in step 1 is N4', N4'-diphenyl-[1,1'-biphenyl]-3,4,4 'Triamine, N4', N4'-diphenyl-[1,1'-biphenyl]-2,3,4'Triamine, N4, N4, N4', N4"-tetraphenyl[1,1 ':2',1"-terphenyl]-4,4',4",5'-tetramine, N4,N4,N4',N4"-tetraphenyl[1,1':4',1" -terphenyl]-2',3',4,4"-tetramine, (4,5-diamino-4'-(diphenylamino)-[1,1'-biphenyl]-2- Base) diphenylphosphine oxide, (2,3-diamino-4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)diphenylphosphine oxide, N4', N4'-diphenyl-[1,1'-biphenyl]-3,4,4'triamine, N4',N4'-diphenyl-[1,1'-biphenyl]-2,3, 4'triamine, N4, N4, N4', N4"-tetraphenyl[1,1':2',1"-terphenyl]-4,4', 4", 5'-tetramine, N4, N4, N4', N4"-tetraphenyl[1,1':4',1"-terphenyl]-2',3',4,4"-tetramine, (4,5-diamino-4 '-(diphenylamino)-[1,1'-biphenyl]-2-yl)diphenylphosphine oxide or (2,3-diamino-4'-(diphenylamino)-[1 ,1'-biphenyl]-4-yl)diphenylphosphine oxide. Others are the same as...

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Abstract

The invention relates to a thermally excited delayed fluorescent material, and a synthesis method and an application thereof, and concretely relates to a phosphonooxy-modified dipyridophenazine-based red/near-infrared thermally excited delayed fluorescent material, and a synthesis method and an application thereof. The purpose of the invention is to solve the problem of concentration quenching caused by large molecular polarity of existing problems of red/near-infrared TADF materials and the problems of low efficiency and fast attenuation of electroluminescent devices. The structural formula of the material is shown in the description. The synthesis method comprises the following steps: 1, preparing an intermediate; 2, taking and mixing the intermediate, palladium acetate, sodium acetate, diphenylphosphine and N,N-dimethylformamide, reacting the obtained mixture at 150 DEG C for 48 h, oxidizing the obtained reaction product, extracting the oxidized reaction product with water and dichloromethane, mixing obtained organic layers, drying the organic layer mixture to remove the organic solvent, and purifying the obtained product to obtain the phosphonooxy-modified dipyridophenazine-based red/near-infrared thermally excited delayed fluorescent material. The material of the invention significantly improves the efficiency of electroluminescent devices, reduces the quenching effect, and enhances the efficiency stability of the electroluminescent devices. 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) have attracted much attention due to their outstanding advantages of light weight, flexibility, low power consumption and low cost, and have become the leader in the field of new generation flat panel display technology and lighting. In the light-emitting layer of an organic light-emitting diode, the excitons formed by the recombination of holes and electrons injected from the anode and cathode respectively are divided into excited singlet excitons and excited triplet excitons, and the ratio of the numbers is 1:3. The singlet excitons radiate back to the ground state to emit fluorescence, while the triplet excitons are spin-forbidden, so the process of returning to the ground state from triplet radiation cannot occur, and most of them are l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561C09K11/06H01L51/54
CPCC07F9/65616C09K11/06C09K2211/1044C09K2211/1007C09K2211/1014H10K85/6572
Inventor 韩春苗赵炳捷许辉
Owner HEILONGJIANG UNIV
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