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Phosphinoxy group-modified dipyridophenazinyl red light/near-infrared thermally excited delayed fluorescence material, synthesis method and application thereof

A near-infrared heat and delayed fluorescence technology, which is applied in the direction of luminescent materials, chemical instruments and methods, and compounds of group 5/15 elements of the periodic table, can solve the problems of low efficiency of light-emitting devices, concentration quenching, and fast decay. Reach the effect of reducing quenching effect, improving efficiency and inhibiting intermolecular interaction

Active Publication Date: 2021-11-26
HEILONGJIANG UNIV
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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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  • Phosphinoxy group-modified dipyridophenazinyl red light/near-infrared thermally excited delayed fluorescence material, synthesis method and application thereof
  • Phosphinoxy group-modified dipyridophenazinyl red light/near-infrared thermally excited delayed fluorescence material, synthesis method and application thereof
  • Phosphinoxy group-modified dipyridophenazinyl red light/near-infrared thermally excited delayed fluorescence material, synthesis method and application thereof

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specific Embodiment approach 1

[0067] 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,

[0068] Z is hydrogen, W is hydrogen or M is hydrogen or V is hydrogen or

[0069] N is hydrogen or U is hydrogen or

[0070] When W, Y, Z, M, V are hydrogen, X is N and U are , its structural formula is:

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

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

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

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

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

[0076] When W, Y, Z, N, U are hydr...

specific Embodiment approach 2

[0082] 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:

[0083] 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;

[0084] 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

[0085] 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

A dipyridophenazine-based red light / near-infrared thermally excited delayed fluorescent material modified by a phosphinoxyl group, a synthesis method and an application thereof, which relate to a thermally excited delayed fluorescent material, a synthetic method and an application thereof. The invention aims to solve the problems of the existing red / near-infrared TADF materials, such as the concentration quenching caused by the large polarity of molecules, and the problems of low efficiency and fast decay of electroluminescent devices. The structural formula is as follows: Synthetic method: 1. Prepare the intermediate; 2. Mix the intermediate, palladium acetate, sodium acetate, diphenylphosphine and N,N dimethylformamide, react at 150°C for 48 hours, oxidize, water and dichloro Extract with methane, combine the organic layers, remove the organic solvent after drying, and purify to obtain the dipyridoxphenazinyl red light / near-infrared thermal excitation delayed fluorescence material modified by phosphine groups. 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) 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 Patents(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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