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Solid-state upconversion light emitting material based on triplet state-triplet state annihilation and preparation method thereof

A technology for triplet annihilation and luminescent materials, applied in the direction of luminescent materials, chemical instruments and methods, etc., can solve the problems of increasing the annihilation efficiency of triplet excitons, performance gap, etc., and achieve the effect of benefiting the upconversion luminous efficiency

Active Publication Date: 2018-01-12
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although researchers have made great efforts in developing new solid-state or quasi-solid-state TTA upconversion systems, there is still a large gap in the performance of these systems compared with homogeneous solutions.
Therefore, how to improve the energy transfer and migration efficiency between the solid-state triplet-triplet state, increase the annihilation efficiency of the triplet excitons in the solid-state environment, reduce the concentration-induced or self-quenching of the excited state of the acceptor in the aggregated state, and improve the upconversion of the aggregated state Luminescent performance is critical and challenging

Method used

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  • Solid-state upconversion light emitting material based on triplet state-triplet state annihilation and preparation method thereof
  • Solid-state upconversion light emitting material based on triplet state-triplet state annihilation and preparation method thereof
  • Solid-state upconversion light emitting material based on triplet state-triplet state annihilation and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0072] A preparation of a solid-state up-conversion luminescent material based on triplet-triplet annihilation, comprising the following steps:

[0073] 1. Synthesis of annihilation agent DSA-1

[0074] 1. Synthetic compound 9,10-dichloromethylanthracene:

[0075] In a 500mL three-necked flask, add anthracene (18.0g, 101mmol), paraformaldehyde (16.4g), 25mL concentrated HCl solution and 150mL 1,4-dioxane solution in sequence, and introduce HCl gas under stirring, and reflux for 2h. Then stop feeding HCl gas, and the reaction solution continued to reflux for 3h. After the reaction, cool to room temperature, filter with suction, and wash the filter cake twice with 1,4-dioxane and water respectively to obtain 3.0 g of a yellow-green solid with a yield of 75%.

[0076] 2. Synthesis of compound 9,10-bis(diethoxyphosphomethyl)anthracene:

[0077] Add 2.5 g (9.1 mmol) of 9,10-dichloromethylanthracene and 18 mL of triethyl phosphite solution into the reaction flask, and reflux for ...

Embodiment 2

[0087] A preparation of a solid-state up-conversion luminescent material based on triplet-triplet annihilation, comprising the following steps:

[0088] 1. Synthesis of annihilation agent DSA-2

[0089] 1. Synthesis of compound 9,10-bis(diethoxyphosphomethyl)anthracene: same as in Example 1.

[0090] 2. Synthesis of Compound II: Same as in Example 1.

[0091] 3. Synthesis of 9,10-bis((E)-4-fluorostyryl)anthracene (DSA-2):

[0092] Compound II (200mg, 0.42mmol) and 4-fluorobenzaldehyde (114mg, 0.92mmol) and 20mL of dry THF were added to the reaction flask, and potassium tert-butoxide (380mg, 3.34mmol) was added with stirring at 0°C. Return to room temperature and react for 8 hours. After the reaction, add an appropriate amount of ethanol, filter with suction, wash the filter cake twice with ethanol and water, and recrystallize once with THF to obtain 123 mg of yellow-green solid DSA-2, with a yield of 70%. figure 2 Shows that the prepared DSA-2 is in CDCl 3 middle 1 H NMR...

Embodiment 3

[0096] A preparation of a solid-state up-conversion luminescent material based on triplet-triplet annihilation, comprising the following steps:

[0097] 1. Synthesis of annihilation agent DSA-3

[0098] 1. Synthesis of compound 9,10-bis(diethoxyphosphomethyl)anthracene: same as in Example 1.

[0099] 2. Synthesis of Compound II: Same as in Example 1.

[0100] 3. Synthesis of 9,10-bis((E)-4-chlorostyryl)anthracene (DSA-3):

[0101] Compound II (200mg, 0.42mmol) and 4-chlorobenzaldehyde (129mg, 0.92mmol) and 20mL of dry THF were added to the reaction flask, and potassium tert-butoxide (380mg, 3.34mmol) was added under stirring at 0°C. Return to room temperature and react for 8 hours. After the reaction, add an appropriate amount of ethanol, filter with suction, wash the filter cake twice with ethanol and water, and recrystallize once with THF to obtain 129 mg of yellow-green solid DSA-3, with a yield of 65%. image 3 Shows that the prepared DSA-3 is in CDCl 3 middle 1 H NMR...

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Abstract

The invention discloses a solid-state upconversion light emitting material based on triplet state-triplet state annihilation, and relates to the technical field of photon upconversion. The solid-stateupconversion light emitting material comprises a photosensitive agent and an annihilation agent with a 9,10-diphenyl vinyl anthracene structure, wherein the annihilation agent has AIE (aggregation-induction emission) effect. The solid-state upconversion light emitting material is formed by physically doping the annihilation agent into the photosensitive agent, and has the advantages that becausethe annihilation agent has regular structure in the solid state, the fluorescence quantum yield is high in the solid state, the energy transfer in the annihilation is favorably performed, the self-quenching of conversion light emitting is avoided, and the problem of self-quenching of the annihilation agent in the solid due to aggregation is certainly solved; the quick energy transfer among the triplet states of the annihilation agent in the solid is favorable for realizing the triplet state-triplet state annihilation of the molecules of the annihilation agent, and is further favorable for improving the upconversion light emitting efficiency.

Description

technical field [0001] The invention relates to the technical field of photon up-conversion. More specifically, it relates to a solid-state up-conversion luminescent material based on triplet-triplet annihilation and a preparation method thereof. Background technique [0002] Photon upconversion is a technology that absorbs two or more low-energy photons, converts them into high-energy photons, and releases them. Photon upconversion has also shown broad application prospects in the fields of solar energy conversion, biological imaging, and diagnosis and treatment, and has received more and more attention. At present, the systems for achieving upconversion luminescence mainly include two-photon absorption upconversion, rare earth doped nano-scale upconversion, nonlinear optical materials, and triplet-triplet annihilation upconversion (TTA). Compared with other upconversion methods, triplet-triplet annihilation upconversion has the advantage of using a low-power incoherent e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
Inventor 李嫕李力曾毅于天君陈金平
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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