Dark blue organic light-emitting material and preparation method and application thereof

A luminescent material, dark blue technology, applied in the direction of luminescent materials, organic chemistry, silicon organic compounds, etc., can solve the problems of poor stability and poor color purity of blue light, and achieve the effect of enhanced stability and improved color purity

Inactive Publication Date: 2020-02-14
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide a deep blue organic luminescent material and its preparation method, aiming to solve the problems of poor color purity and poor stability of blue light in existing TADF blue light materials

Method used

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  • Dark blue organic light-emitting material and preparation method and application thereof
  • Dark blue organic light-emitting material and preparation method and application thereof
  • Dark blue organic light-emitting material and preparation method and application thereof

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preparation example Construction

[0038] The embodiment of the present invention provides a method for preparing a deep blue organic light-emitting material as described above, wherein the reaction formula is: According to reaction formula (1), including steps:

[0039] A. Under the inert atmosphere, under the joint catalysis of tris(dibenzylideneacetone)dipalladium and tri-tert-butylphosphorus, R 1 The substituted 1,3-dibromobenzene reacts with the secondary amine compound in the first organic solvent, and is separated by column chromatography to obtain the ditertiary amine compound; the secondary amine compound is

[0040] B. Under inert atmosphere, ditertiary amine compounds and MBr 3 The reaction is carried out in the second organic solvent and purified to obtain a dark blue organic light-emitting material.

[0041] In one embodiment, the inert atmosphere may be, but not limited to, a nitrogen atmosphere or an argon atmosphere.

[0042] In one embodiment, in step A, the first organic solvent may be...

Embodiment 1

[0057] Example 1 Preparation of dark blue organic light-emitting material 1b, the reaction formula is

[0058]

[0059] (1) Preparation of ditertiary amine compound 1a

[0060] According to reaction formula (2), the specific steps are: under nitrogen atmosphere, tris(dibenzylideneacetone)dipalladium (0.4mmol), tri-tert-butylphosphorus (1.2mmol), 1-fluoro-3,5- Dibromobenzene (10 mmol) and diphenylamine (22 mmol) were dispersed in dry toluene (80 mL), heated to reflux (110° C.) and reacted at this temperature for 16 h. After the reaction system was cooled to room temperature, the reaction solution was diluted, and the diluted reaction solution was suction filtered with a Buchner funnel covered with silica gel. Silica gel column chromatography was performed as the eluent to obtain ditertiary amine compound 1a with a yield of 94%.

[0061] (2) Preparation of dark blue organic light-emitting material 1b

[0062] According to reaction formula (2), the specific steps are: under...

Embodiment 2

[0064] (1) Preparation of dark blue organic light-emitting material 1c

[0065] The reaction formula is The specific steps are as follows: under a nitrogen atmosphere, the dark blue organic light-emitting material 1b (5 mmol) and carbazole (6 mmol) are dissolved in N,N-dimethylformamide (30 mL), cesium carbonate (20 mmol) is added, and at 140 The reaction was carried out at ℃ for 16 h. After the reaction was completed, it was extracted with ethyl acetate, washed with water to separate the liquids, dried the organic phase, spin-dried and separated on the column to obtain the dark blue organic light-emitting material 1c with a yield of 83%. The structure of the dark blue organic light-emitting material 1c was identified, and the measured data included: 1 H NMR (CDCl 3 ,400MHz)δ9.04(dd,J=18.9,2.1Hz,2H),8.33(d,J=1.8Hz,1H),8.16(d,J=2.0Hz,1H),7.55–7.36(m,5H ), 7.34–7.10 (m, 11H), 6.65 (d, J=9.0Hz, 1H), 6.20–6.15 (m, 1H); 13 C NMR (CDCl 3 ,100MHz)13C NMR(101MHz,CDCl3)δ151.90,15...

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Abstract

The invention discloses a dark blue organic light-emitting material and a preparation method and application thereof. The dark blue organic light-emitting material contains a structural unit disclosedin the invention, wherein, M is B or Bi; X is O, S or NR4; R1-R4 are independently selected from connecting bonds or groups obtained from H-H, H-F, H-O-H, H-S-H, H-CN, saturated hydrocarbons, unsaturated hydrocarbons, fluorinated hydrocarbons, heterocyclic compounds, organoboron, organosilicone, alcohols, mercaptans, ethers, thioethers, phenols, thiophenol, aldehydes, ketones, amines, amides, nitriles or sulfones losing one or more H; R1-R3 are located at any substitution position on rings of the structural unit where R1-R3 are located, and the bond energy between the ring where R3 is locatedand M is greater than or equal to the bond energy between the ring where R2 is located and M. The dark blue organic light-emitting material containing the B / Bi-N main body structure has very narrow light-emitting spectrum and TADF properties; the color purity is high, and the stability is good.

Description

technical field [0001] The present invention relates to the technical field of organic light-emitting materials, in particular to a deep blue organic light-emitting material and a preparation method and application thereof. Background technique [0002] Since the discovery of organic light-emitting diodes (OLEDs), organic light-emitting devices mainly use organic light-emitting small molecules and high molecular polymers as light-emitting materials, and prepare organic light-emitting layers by evaporation or spin coating. However, due to the poor solubility of organic light-emitting small molecules, the low luminous efficiency of fluorescent materials, and the fact that phosphorescent light-emitting materials generally contain precious metals, the conditions required by the evaporation process are harsh, making the manufacturing process cost of organic light-emitting devices extremely high; Due to the poor reproducibility of the synthesis and the difficulty in purification, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F9/94C09K11/06C07F7/08H01L51/54
CPCC07F5/027C07F9/94C09K11/06C07F7/0816C09K2211/107C09K2211/1055C09K2211/1096C09K2211/1029C09K2211/1085H10K85/60H10K85/657H10K85/40H10K85/6572
Inventor 孟鸿施明孙越
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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