Rare earth polymer luminescent material with Tpy as neutral ligand, and preparation and application thereof

A technology of rare earth polymers and neutral ligands, applied in luminescent materials, compounds containing group 3/13 elements of the periodic table, semiconductor/solid-state device manufacturing, etc., can solve unstable quality and performance, low brightness and efficiency , difficulty in preparation and other issues, to achieve the effect of improving electroluminescence and electrical storage performance, small steric hindrance effect, and simple preparation method

Inactive Publication Date: 2013-12-11
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solve the problems of difficult preparation, long preparation cycle, unstable quality and per

Method used

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  • Rare earth polymer luminescent material with Tpy as neutral ligand, and preparation and application thereof
  • Rare earth polymer luminescent material with Tpy as neutral ligand, and preparation and application thereof
  • Rare earth polymer luminescent material with Tpy as neutral ligand, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1 Synthesis of 4-(4-vinylbenzyloxy)benzaldehyde

[0067] 4.89 grams of p-hydroxybenzaldehyde (40mmol) and 7.16 grams of 4-vinylbenzyl chloride (40mmol) were added to a 250mL one-necked flask, completely dissolved with 100mL of DMF, then 2.25 grams of KOH (40mmol) was added, and stirred at room temperature for 12 hours, After the reaction, the obtained solution was added to 800 mL of distilled water, and a large amount of precipitates were precipitated, filtered, washed with 50 mL of distilled water for 3 times, and vacuum-dried at 60°C. In order to remove excess 4-vinylbenzyl chloride, the dried product was washed three times with 30 mL of n-hexane, and the obtained solid was dried to obtain 8.11 g of the product, with a yield of 85%. 1 H NMR (400MHz CDCl 3 ):5.14(s,2H);5.27-5.29(d,1H,J HH =11);5.75-5.80(d,1H,J HH =18);6.69-6.76(dd,1H,J HH =18, J HH =12);7.06-7.09(d,2H,J HH =9);7.38-7.46(dd,4H,J HH =8,J HH =8);7.83-7.85(d,2H,J HH =8);9.89(s,1H).ESI-MS:m...

Embodiment 2

[0068] Example 2 Synthesis of polymerizable tpy ligands

[0069] 2.38 grams of 4-(4-vinylbenzyloxy)benzaldehyde (10mmol) and 2.42 grams of 2-acetylpyridine (20mmol) were added together in a 250mL three-necked flask with magnetic stirring, then 100mL of absolute ethanol was added, and ultrasonic Allow the reactants to dissolve completely, then add 1.55 g of KOH (85%, 20 mmol) and 30 mL of ammonia solution (29.3, 25 mmol), stir at room temperature for 12 hours, filter after the reaction, and wash the resulting solid three times with 60 mL of absolute ethanol, and dry Obtain milky white solid powder 2.73 grams, productive rate 62%. 1 H NMR (400MHz CDCl 3 ):8.65-8.71(m,6H,tpy),7.83-7.88(t,4H,ArH),7.40-7.45(m,4H,ArH),7.26-7.33(t,2H,tpy),7.07-7.09( d,2H,ArH),6.70-6.77(m,1H,CH=CH 2 ),5.75-5.80(d,1H,CH=CH 2 ),5.25-5.28(d,1H,CH=CH 2 ),5.08(S,2H,-CH 2 -). 13 C NMR (100MHz CDCl 3):159.5,156.2,155.7,149.5,148.9,137.1,136.8,136.3,130.9,128.4,127.7,126.4,123.7,121.3,118.2,115.1,114....

Embodiment 3

[0070] Embodiment 3 Synthesis of polymerizable monomer tpy rare earth europium complex

[0071] In a round-bottomed flask with a reflux device and a stirring device, dissolve 3 mmol of β-diketone in tetrahydrofuran, then add 3 mmol of hydrogen sodium oxide, and react at 65°C for 20 minutes, then add one equivalent of β-diketone dissolved in ethanol EuCl in 3 2H 2 O solution, reacted at 65°C for 1h, then added 1mmol of polymerizable tpy compound containing a small amount of polymerization inhibitor to the aforementioned reaction system, and then reacted at 65°C for 6h, cooled to room temperature after the reaction, and then vacuum desolventized, After washing with appropriate amount of distilled water and ethanol, and vacuum drying, 0.93 g of a polymerizable tpy rare earth europium complex was obtained. The product was bright yellow, and the yield was 74%. (Found: C, 50.08; H, 2.94; N, 3.19.EuC 54 h 35 f 9 N 3 o 7 S 3 [EuVTPY]requires C,51.60;H,2.81;N,3.35%). 1 H NMR (...

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Abstract

The invention discloses a rare earth polymer luminescent material with Tpy as a neutral ligand and preparation and application thereof, belonging to the field of luminescent materials. The invention overcomes the problems of great preparation difficulty, a long period, instable quality and performance, low brightness and efficiency, etc. of rare earth electroluminescent polymer materials in the prior art. According to the invention, a polymerizable Tpy rare earth complex and N-vinyl carbazole are used as monomers and subjected to radical copolymerization so as to obtain the rare earth polymer luminescent material with Tpy as the neutral ligand. The rare earth polymer luminescent material with Tpy as the neutral ligand is applied as a luminescent layer material or luminescent layer doping material for an electroluminescent device, and the prepared electroluminescent device has turn-on voltage of 12 to 37 V, electroluminescent brightness of 0.1 to 70 cd/m<2> and maximum external quantum efficiency of 0.37%. The prepared polymer can also be applied to an electroactive layer of a polymer electrical memory device. A synthetic method used in the invention is simple and easily practicable and is easy to industrialize.

Description

technical field [0001] The invention belongs to the field of light-emitting materials, and in particular relates to a rare-earth polymer light-emitting material with terpyridine (tpy) as a neutral ligand, as well as its preparation and application. Background technique [0002] my country is rich in rare earth resources, accounting for more than 80% of the world's proven reserves. Rare earth elements are known as industrial "gold". Due to their excellent optical, electromagnetic and other physical properties, they can be combined with other materials to form a wide variety of new materials with different properties. The most significant function is to greatly improve the quality and quality of other products. performance. Especially in the field of luminescent materials, rare earth elements, as important elements in inorganic semiconductors, have shown vigorous vitality once they are introduced into the field of organic electronics, showing significant advantages and broad ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/00C08F230/04H01L51/54
Inventor 吕满庚杨朝龙许静
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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