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Blue fluorescent material with high exciton utilization rate and preparation and application thereof

A technology of blue fluorescence and utilization rate, which is applied in the direction of luminescent materials, semiconductor/solid-state device manufacturing, electrical components, etc., can solve the problems of efficiency roll-off, unfavorable application, and exciton utilization rate of only 62.5%, achieving good performance, The effect of reducing exciton quenching and improving exciton utilization

Active Publication Date: 2021-03-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the first two types of materials rarely meet the blue light color coordinates CIE y <0.15 high-efficiency materials, in addition, these two types of materials also face serious efficiency roll-off problems, which is not conducive to practical application
However, the TTA fluorescent material forms a singlet exciton by fusing two triplet excitons, and the exciton utilization rate is only 62.5% [Science China Chemistry, 2014, 57, 335–345]

Method used

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  • Blue fluorescent material with high exciton utilization rate and preparation and application thereof
  • Blue fluorescent material with high exciton utilization rate and preparation and application thereof
  • Blue fluorescent material with high exciton utilization rate and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of embodiment 1 compound M1

[0033] The structural formula and reaction equation of compound M1 are

[0034]

[0035] (1) Synthesis of compound 1

[0036] Under nitrogen protection, phenanthrenequinone (10mmol), p-bromobenzaldehyde (10mmol), aniline (10mmol), ammonium acetate (30mmol) were added to 80ml of acetic acid, heated to reflux for 24 hours. After cooling to room temperature and standing still, suction filtration was performed, and the filter residue was washed with ethanol three times to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 77%. 1 HNMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0037] (2) Synthesis of compound 2

[0038] In a nitrogen atmosphere, compound 1 (10mmol), biboronic acid pinacol ester (12mmol), potassium acetate (30mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium ...

Embodiment 2

[0043] The preparation of embodiment 2 compound M2

[0044] The structural formula and reaction equation of compound M2 are

[0045]

[0046] (1) Synthesis of compound 4

[0047] Under nitrogen protection, phenanthrenequinone (10mmol), m-bromobenzaldehyde (10mmol), aniline (10mmol), ammonium acetate (30mmol) were added to 80ml of acetic acid, heated to reflux for 24 hours. After cooling to room temperature and standing still, suction filtration was performed, and the filter residue was washed with ethanol three times to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 74%. 1 HNMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0048] (2) Synthesis of compound 5

[0049] In a nitrogen atmosphere, compound 4 (10mmol), biboronic acid pinacol ester (12mmol), potassium acetate (30mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium ...

Embodiment 3

[0054] The preparation of embodiment 3 compound M3

[0055] The structural formula and reaction equation of compound M3 are

[0056]

[0057] (1) Synthesis of Compound 7

[0058] Under nitrogen protection, add phenanthrenequinone (10mmol), p-bromobenzaldehyde (10mmol), 2-naphthylamine (10mmol), ammonium acetate (30mmol) into 80ml of acetic acid, and heat to reflux for 24 hours. After cooling to room temperature and standing still, suction filtration was performed, and the filter residue was washed with ethanol three times to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 71%. 1 HNMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0059] (2) Synthesis of Compound 8

[0060] In a nitrogen atmosphere, compound 7 (10mmol), biboronic acid pinacol ester (12mmol), potassium acetate (30mmol), [1,1'-bis(diphenylphosphino)ferrocene]palla...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a blue fluorescent material with high exciton utilization rate as well as preparation and application thereof. The blue fluorescent material is one or more of a formula I and a formula II. The invention also discloses a preparation method of the blue fluorescent material. The material provided by the invention is a blue fluorescent material, can form hybrid local charge transfer state (HLCT) luminescence, realizes a high-energy triplet state to singlet state reverse system crossing process, and improves the exciton utilization rate. Meanwhile, the blue fluorescent material is high in fluorescence quantum yield, high in carrier mobility and good in stability. The material provided by the inventionhas good performance in organic light-emitting devices. The blue fluorescent material disclosed by the invention is used for preparing an organic light-emitting device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of phenanthroimidazole-based blue fluorescent materials, a preparation method thereof and an application in electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of self-luminescence, low-voltage drive, high contrast, fast response, low energy consumption, wide operating range, and flexibility, and have attracted extensive attention from industry and academia. OLED-related research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic molecular single crystal anthracene for the first time, and then some single crystal structure materials have electroluminescence properties. However, due to the high driving voltage of the device at that time, it failed to attract widespread attention. It wasn't...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C09K11/06H01L51/50H01L51/54
CPCC07D235/02C09K11/06C09K2211/1044H10K85/615H10K85/6572H10K50/11Y02E10/549
Inventor 马於光应磊胡德华
Owner SOUTH CHINA UNIV OF TECH