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A Class of Europium Complex Luminescent Materials Based on Tridentate Anionic Ligands

A technology of anionic ligands and europium complexes, which can be applied to luminescent materials, compounds of Group 5/15 elements of the periodic table, compounds containing elements of Group 3/13 of the periodic table, etc., which can solve the problem of easy dissociation of sexual ligands. , poor stability and other problems, to achieve the effects of high carrier mobility, high coordination stability constant, and high thermal decomposition temperature

Active Publication Date: 2017-11-03
苏州睿尔思科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the technical problems of easy dissociation and poor stability of the neutral ligands of existing rare earth complexes, and to obtain a rare earth luminescent material with high luminous efficiency, thermal stability and light stability

Method used

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  • A Class of Europium Complex Luminescent Materials Based on Tridentate Anionic Ligands
  • A Class of Europium Complex Luminescent Materials Based on Tridentate Anionic Ligands
  • A Class of Europium Complex Luminescent Materials Based on Tridentate Anionic Ligands

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The synthetic route involved in the present embodiment is as follows:

[0046]

[0047] 1.1 Synthesis of ligand 1f (4-hydroxy-6-diethylphosphoryl-1,5-naphthyridine, 4-hydroxy-6-(diethylphosphoryl)-1,5-naphthyridine)

[0048] Reaction of 4-hydroxy-6-chloro-1,5-naphthyridine (1a) with NaOH affords its sodium salt 1b. Heat 30mmol of diethylphosphine chloride (1c) and 60mmol of metal sodium in tetrahydrofuran solution to reflux for 24h to obtain the sodium salt of diethylphosphine (1d). Add 30mmol sodium salt 1b of chlorinated ND to the freshly prepared solution of sodium diethylphosphine (1d), heat to reflux for 24h, and obtain ND (1e) substituted by diethylphosphine through coupling reaction. After the reaction, an equivalent amount of m-chloroperoxybenzoic acid (mCPBA) was added, stirred for 1 h, and then the pH of the solution was adjusted to 7-8 with hydrochloric acid to obtain the oxidized product. The product was purified by vacuum sublimation, then recrystalliz...

Embodiment 2

[0053] The synthetic route involved in the present embodiment is as follows:

[0054]

[0055] 2.1 Ligand 2f (3-methyl-4-hydroxy-6-diethylphosphinooxy-1,5-naphthyridine, 3-methyl-4-hydroxy-6-(diethylphosphoryl)-1,5-naphthyridine) Synthesis

[0056] The synthesis procedure is the same as in Example 1 (part 1.1), except that 4-hydroxyl-6-chloro-1,5-naphthyridine (1a) is replaced by 3-methyl 4-hydroxyl-6-chloro-1,5-naphthyridine (2a). Ligand 2f white powder 0.95 g was obtained with a yield of 12%.

[0057] 1 H NMR (400 MHz, MeOD) 8.15-8.03 (m, 2H), 7.99 (s, 1H), 2.68 (s, 3H), 2.11-1.92 (m, 4H), 1.03-0.90 (m, 6H). Mass spectrometry (m / z, ESI): Calculated 264.1, found 265.1 (M+H) + . Elemental analysis (mass percentage): C, 59.02 (59.09); H, 6.48 (6.48); N, 10.65 (10.60), the theoretical values ​​in brackets.

[0058] 2.2 Synthesis of complex Eu2

[0059] The synthesis steps are the same as in Example 1 (part 1.2), except that the ligand 1f is replaced with 2f. 0.73 g o...

Embodiment 3

[0061] The synthetic route involved in the present embodiment is as follows:

[0062]

[0063] 3.1 Ligand 3f (3-cyano-4-hydroxyl-6-diethylphosphinoxy-1,5-naphthyridine, 3-cyano-4-hydroxy-6-(diethylphosphoryl)-1,5-naphthyridine) Synthesis

[0064] The synthesis procedure is the same as in Example 1 (part 1.1), except that 4-hydroxyl-6-chloro-1,5-naphthyridine (1a) is replaced by 3-cyano 4-hydroxyl-6-chloro-1,5-naphthyridine (3a). Ligand 3f white powder 1.56g was obtained with a yield of 19%.

[0065] 1 H NMR (400 MHz, MeOD) 8.36-8.20 (m, 2H), 8.16 (s, 1H), 2.18-1.96 (m, 4H), 1.03-0.92 (m, 6H). Mass spectrometry (m / z, ESI): calculated 275.1, found 276.1 (M+H) + . Elemental analysis (% by mass): C, 56.78 (56.73); H, 5.09 (5.13); N, 15.31 (15.27), the theoretical values ​​in brackets.

[0066] 3.2 Synthesis of complex Eu3

[0067] The synthesis steps are the same as in Example 1 (part 1.2), except that the ligand 1f is replaced with 3f. 0.83 g of the white target europ...

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Abstract

The invention discloses a rare earth europium complex luminescent material based on tridentate anionic ligand and its preparation method and application. The general structural formula of the europium complex is Eu(t-ND)3, where t-ND is a 4-hydroxy-1,5-naphthyridine tridentate anionic ligand substituted by a phosphineoxy group, a sulfoxide group or a sulfone group. . This type of europium complex has a more rigid structure, a high coordination stability constant, is not prone to dissociation of ligands, and has a high thermal decomposition temperature; the phosphine atoms and sulfur atoms are sp3 hybridized without strong conjugation effects. It ensures that the ligands have appropriate energy levels and the complexes also have high luminous efficiency; in addition, this type of europium complex also has good ultraviolet light tolerance and high electron and hole mobility, and can be used as down-conversion Photoluminescent materials and organic electroluminescent materials.

Description

technical field [0001] The invention relates to a rare earth europium complex luminescent material, a preparation method thereof, and an application in the fields of photoluminescence and electroluminescence. Background technique [0002] Rare earth complex luminescent materials have unique advantages such as high luminous efficiency, long life, and good color purity, and have important application prospects in the fields of lighting, display, light conversion film, and biomedicine. As a photoluminescent material, due to the large molar absorptivity of organic ligands, compared with pure inorganic materials (such as Y 2 o 3 : Eu 3+ ), the light-absorbing ability of rare earth complexes can be increased hundreds of times, and the amount of rare earth can be greatly reduced. Moreover, rare earth complexes have better compatibility with polymers, and are more suitable for use in functional light conversion films than inorganic materials, such as agricultural light conversion...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6561C07F5/00C07D471/04C09K11/06C09K11/02H01L51/54
Inventor 卞祖强卫慧波魏晨赵子丰刘志伟黄春辉
Owner 苏州睿尔思科技有限公司