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Dipyridine phenazinyl red/orange photothermal excitation delayed fluorescence material as well as synthesis method and application thereof

A technology of delayed fluorescence and synthetic methods, which is applied in the direction of luminescent materials, chemical instruments and methods, compounds of group 5/15 elements of the periodic table, etc., can solve problems such as concentration quenching, fast decay, and low efficiency of light-emitting devices, and achieve Improve efficiency, inhibit intermolecular interactions, and reduce quenching effects

Active Publication Date: 2019-07-19
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 problem of concentration quenching caused by the large molecular polarity of the existing red / orange light TADF materials and the problems of low efficiency and fast decay of electroluminescent devices, and provides a dipyridophenazine-based Red / orange thermally excited delayed fluorescent materials, synthesis methods and applications

Method used

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  • Dipyridine phenazinyl red/orange photothermal excitation delayed fluorescence material as well as synthesis method and application thereof
  • Dipyridine phenazinyl red/orange photothermal excitation delayed fluorescence material as well as synthesis method and application thereof
  • Dipyridine phenazinyl red/orange photothermal excitation delayed fluorescence material as well as synthesis method and application thereof

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Experimental program
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specific Embodiment approach 1

[0058] Specific embodiment 1: In this embodiment, the structural formula of the dipyridophenazinyl red / orange photothermal excitation delayed fluorescence material is as follows:

[0059] where X is hydrogen or

[0060] Y is hydrogen,

[0061] Z is hydrogen,

[0062] W is hydrogen or

[0063] When X, Y, Z are hydrogen, W is , its structural formula is:

[0064]

[0065] When X, Y are hydrogen, W, Z are , its structural formula is:

[0066]

[0067] When W, Y, Z are hydrogen, X is , its structural formula is:

[0068]

[0069] When W and Z are hydrogen, X and Y are , its structural formula is:

[0070]

[0071] When X, Y are hydrogen, W is Z is , its structural formula is:

[0072]

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

[0074]

specific Embodiment approach 2

[0075] Specific embodiment 2: The synthesis method of the dipyridophenazinyl red / orange photothermal excitation delayed fluorescent material described in specific embodiment 1 is carried out according to the following steps:

[0076] 1. Mix 1 mmol of 5-bromobenzothiadiazole or 4-bromobenzothiadiazole, 1 mmol of triphenylamine-4-boronic acid pinacol ester, 0.05 to 0.1 mmol of tetrakis(triphenylphosphine) palladium, Mix 0.1mmol of tetrabutylammonium bromide, 2-10mmol of sodium hydroxide and 5-10ml of toluene, react at 120°C for 48h, extract with water and dichloromethane, combine the organic layers, remove the organic solvent after drying, and dichloromethane The mixed solvent with petroleum ether is eluent column chromatography and purified to obtain 4-(.benzo[c][1,2,5]thiadiazol-5-yl)-N,N-diphenylaniline or 4-(Benzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenylaniline;

[0077] 2. Add 1 mmol of 5,6-dibromobenzothiadiazole or 4,7-dibromobenzothiadiazole, 2 mmol of triphenylamine-4-bo...

specific Embodiment approach 3

[0082] Specific embodiment three: the difference between this embodiment and specific embodiment two is that in step one, 1 mmol of 5-bromobenzothiadiazole or 4-bromobenzothiadiazole, 1 mmol of triphenylamine-4-boric acid pina Alcohol ester, 0.05mmol of tetrakis(triphenylphosphine) palladium, 0.1mmol of tetrabutylammonium bromide, 6mmol of sodium hydroxide and 10ml of toluene were mixed and reacted at 120°C for 48h; in step 2, 1mmol of 5,6-di Bromobenzothiadiazole or 4,7-dibromobenzothiadiazole, 2mmol of triphenylamine-4-boronic acid pinacol ester, 0.05mmol of tetrakis(triphenylphosphine) palladium, 0.1mmol of tetrabutyl Ammonium bromide, 6mmol sodium hydroxide and 10ml toluene were mixed and reacted at 120°C for 48h. Others are the same as in the second embodiment.

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Abstract

The invention discloses a dipyridine phenazinyl red / orange photothermal excitation delayed fluorescence material as well as a synthesis method and the application thereof. The invention relates to a fluorescence material as well as the synthesis method and the application thereof. The invention aims at solving the problems of concentration quenching, extremely-low efficiency and fast attenuation of electroluminescent devices due to high molecular polarity in an existing red / orange light TADF material. The structure of the material is as shown in the specification. The synthesis method comprises the following steps: preparing (6-(4-(diphenyl amino) phenyl) benzo[c][1,2,5] thiadiazole-5-yl) diphenylphosphine oxide or (7-(4-(diphenyl amino) phenyl) benzo[c][1,2,5]thiadiazole-4-yl) diphenylphosphine oxide; preparing the required donor; and obtaining a final product. The material disclosed by the invention has the advantages that the efficiency of an electroluminescent device is obviously improved, the quenching effect is reduced and the efficiency stability of the electroluminescent device is enhanced. The invention belongs to the preparation field of fluorescent materials.

Description

technical field [0001] The invention relates to a fluorescent material, a synthesis method and an application thereof. Background technique [0002] It has been more than 20 years since Organic Light-Emitting Diodes (OLED) was first reported. During this period, OLED has achieved rapid development in terms of material synthesis process and device preparation. From light sources used for lighting to mobile phones, digital cameras, and mp3 display screens in our daily life, especially in the field of TV display technology, large-size, transparent, and bendable OLED screens have attracted the attention of countless customers. The singlet excitons generated by electrical excitation account for one quarter, and the triplet excitons account for three quarters. However, the phosphine pair generated by the triplet excitons does not participate in the process of luminescence, so the luminous efficiency of fluorescent OLED devices has been considered to be lower than 25% for a period...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC07D471/14C07F9/6561C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1044H10K85/6572H10K50/00
Inventor 韩春苗赵炳捷许辉
Owner HEILONGJIANG UNIV
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