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Dark blue light-emitting organic micro-nano crystal material and preparation method thereof

A crystalline material, dark blue technology, applied in luminescent materials, organic chemistry methods, organic chemistry and other directions, can solve the problems of few micro-nano crystals, red shift, lack of electricity, etc., to achieve strong adaptability, regular shape, easy to operate Effect

Active Publication Date: 2021-06-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there have been in-depth studies on the acid-base-stimulated fluorescence response of pyridine-containing functional chromophores in the solution state, but only a few of these compounds show good fluorescence reversible responses in the crystal state; secondly, due to protonation Due to the extreme charge-deficient nature of the post-pyridine group, the above-mentioned functional chromophores often show obvious red shifts when protonated, but rarely show bright luminescence in the deep blue region (wavelength ≤ 430nm)
Moreover, to obtain high-quality blue-light organic micro-nano crystals in the prior art, it is often first to obtain irregular powder through solution reaction, and then to prepare micro-nano crystals, and it is rare to directly obtain micro-nano crystals with appropriate sizes.

Method used

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  • Dark blue light-emitting organic micro-nano crystal material and preparation method thereof
  • Dark blue light-emitting organic micro-nano crystal material and preparation method thereof
  • Dark blue light-emitting organic micro-nano crystal material and preparation method thereof

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preparation example Construction

[0060] The present invention also provides a method for preparing the above-mentioned dark blue light-emitting organic micro-nano crystal material, which uses 2,2'-bis(2-pyridyl)biphenyl and protonic acid as raw materials to prepare the organic micro-nano crystal material. Steps include:

[0061] Step 1. Using 2,2'-bis(2-pyridyl)biphenyl as the proton acceptor, and the proton acid as the proton donor;

[0062] Step 2. Accurately weigh 2,2'-bis(2-pyridyl)biphenyl, add an organic solvent and ultrasonically dissolve to obtain a stock solution of proton acceptor molecules;

[0063] Step 3. Add the protonic acid to the stock solution of proton acceptor molecules under gentle ultrasound, and let stand at room temperature;

[0064] Step 4. The liquid left standing at room temperature is dropped on the substrate, and the organic solvent is evaporated to dryness to obtain a deep blue light-emitting organic micro-nano crystal material based on the molecule shown in formula I.

[0065]...

Embodiment 1

[0075] This embodiment provides a blue organic micro-nano crystal material, which is composed of chloride ion and protonated 2,2'-bis(2-pyridyl)biphenyl cation (2,2'-([1,1'-biphenyl) Benzene]-2,2'-diyl)bis(pyridin-1-ium)) consists of (2,2'-([1,1'-biphenyl]-2,2'-diyl)bis(pyridine- 1-onium) hydrochloride), the chemical formula is C 22 h 26 Cl 2 N 2 o 4 , the molecular weight is 453.35, the crystal space group of the crystal material is C 1 2 / c 1, and the unit cell parameter is α=90°, β=125.443(4)°, γ=90°, V=1615.80(5), a single crystal structure includes a protonated 2,2'-bis(2-pyridyl)biphenyl cation, Two chloride ions and four water molecules, the chloride ion and the hydrogen on the protonated pyridinic nitrogen are connected by a hydrogen bond N-H...Cl, and the length of the hydrogen bond is N-H bond length is

[0076] The present invention provides a preparation method of 2,2'-([1,1'-biphenyl]-2,2'-diyl)bis(pyridin-1-ium) hydrochloride:

[0077] Accurately wei...

Embodiment 2

[0088] This embodiment provides another kind of blue organic micro-nano crystal material, which consists of perchlorate ion and protonated 2,2'-bis(2-pyridyl)biphenyl cation (2,2'-([1,1 '-biphenyl]-2,2'-diyl)bis(pyridin-1-ium)) from (2,2'-([1,1'-biphenyl]-2,2'-diyl)bis (pyridin-1-ium) perchlorate), the chemical formula is C 22 h 18 Cl 2 N 2 o 8 , the molecular weight is 509.28, the crystal space group of the crystal material is P-1, and the unit cell parameter is α=67.08(3)°, β=67.81(3)°, γ=76.78(3)°, V=1434.2(7), a single crystal structure including a protonated 2,2'-bis(2-pyridine base) biphenyl cation, two perchlorate ions, the hydrogen on the perchlorate ion and the protonated pyridinium nitrogen is connected by a strong hydrogen bond N-H...O, and the length of the hydrogen bond is N-H bond length is

[0089] The invention provides a preparation method of 2,2'-([1,1'-biphenyl]-2,2'-diyl)bis(pyridin-1-ium)perchlorate:

[0090] Accurately weigh 3.0mg of 2,2'-bi...

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Abstract

The invention provides a dark blue light-emitting organic micro-nano crystal material and a preparation method thereof, belongs to the field of organic light-emitting materials, and solves the problems that in the prior art, the steps for preparing a dark blue light-emitting organic material are complicated, and an organic micro-nano crystal with a controllable size cannot be obtained in situ. The structural formula of the crystal is shown as (I), wherein X is an acid radical ion of protonic acid. The preparation method comprises the following steps: taking 2, 2 '-bis (2-pyridyl) biphenyl and protonic acid as raw materials to prepare the material. The obtained dark blue light-emitting organic micro-nano crystal compound is regular in morphology and controllable in size, the fluorescence intensity shows good reversibility of acid / alkali stimulation, and the dark blue light-emitting organic micro-nano crystal compound plays an important role in the fields of fluorescence sensors, memories, logical operation and the like.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials, in particular to a dark blue light-emitting organic micro-nano crystal material and a preparation method thereof. Background technique [0002] Deep blue light-emitting organic materials can effectively reduce device energy consumption, and can also achieve full-color light emission through energy transfer, so they play an important role in the fields of solid-state lighting and full-color display. [0003] Among organic light-emitting three-primary-color display materials, compared with green and red light materials that have better performance in terms of efficiency, lifespan and color purity, blue light materials are subject to problems such as large band gaps and low luminous quantum efficiency, and their development is relatively lagging behind. Pyridine-containing organic compounds take advantage of the nucleophilicity and basicity of the pyridine group to show reve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/06C07D213/127C09K11/06
CPCC07D213/06C07D213/127C09K11/06C07B2200/13C09K2211/1029C09K2211/1007
Inventor 钟羽武李仲秋唐健洪龚忠亮
Owner INST OF CHEM CHINESE ACAD OF SCI