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Luminescent organic-polymer/metal complex, luminescent organic-polymer/metal complex composition capable of forming film by wet process, and process for producing the same

A metal complex, organic polymer technology, applied in electroluminescent light sources, chemical instruments and methods, luminescent materials, etc., can solve the problems of low efficiency of electroluminescent elements

Inactive Publication Date: 2006-07-05
NIPPON LIGHT METAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these substances are all copolymers having repeating units combined with aluminum complexes and repeating units without aluminum complexes, and aluminum complexes cannot be introduced into high-molecular repeating units at a high rate, and have high efficiency as electroluminescence elements. low problem

Method used

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  • Luminescent organic-polymer/metal complex, luminescent organic-polymer/metal complex composition capable of forming film by wet process, and process for producing the same
  • Luminescent organic-polymer/metal complex, luminescent organic-polymer/metal complex composition capable of forming film by wet process, and process for producing the same
  • Luminescent organic-polymer/metal complex, luminescent organic-polymer/metal complex composition capable of forming film by wet process, and process for producing the same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0044] Synthesis example 1 (polyQ 1 Synthesis)

[0045] 8-hydroxyquinoline (Q 1 ) 26.2 g (0.201 mol), concentrated hydrochloric acid 36 mL, and 28 wt%-formalin 32 mL (0.3 mol), and hydrogen chloride gas dried at room temperature for 90 minutes was introduced into the obtained mixed solution.

[0046] After the reaction was over, the resulting precipitate was filtered and dried to obtain the chloromethylated product of an amorphous yellow solid (Q 1 -CH 2 Cl·HCl) 37.2 g (yield 80%). The melting point of the obtained product is 280° C. (decomposition), which is in good agreement with the literature value (J. Org. Chem. 26, p4078 (1961); 280° C. (decomposition).

[0047] Then, the chloromethylation product (Q 1 -CH 2 14.5 g (0.0629 mol) of Cl·HCl) and 60 mL (0.43 mol) of excess 2-hydroxyethyl methacrylate (HMA) were reacted at 60° C. for 2 days under an argon atmosphere.

[0048] After the reaction was completed and returned to room temperature, 150 mL of water was added, ...

Synthetic example 2

[0054] Synthesis example 2 (polyQ 2 Synthesis)

[0055] Charge 7-(4-ethyl-1-methyloctyl)-8-hydroxyquinoline (Q 2 ) 45.0g (0.15mol), concentrated hydrochloric acid 75mL, and 28wt%-formalin 25mL (0.23mol), and introduced hydrogen chloride gas dried at 65-75°C for 17 hours into the resulting mixed solution. The resulting reaction was a mixture of an aqueous layer and a dark yellowish-orange solid.

[0056] After completion of the reaction, extraction was performed four times with 100 mL of chloroform from which the stabilizer was removed, and the obtained extract was reprecipitated with 4 L of ether to obtain 23 g of an amorphous yellow solid product.

[0057] The resulting product is 1 H-NMR and 13 Each spectrum of C-NMR confirmed that the 5-position was chloromethylated (Q 2 -CH 2 Cl·HCl) (57% yield).

[0058] 1 H-NMR (400MHz; CDCl 3 )δ (ppm) = 9.14 (1H, d, J = 7.2Hz), 9.04 (1H, br.s), 7.99 (1H, br.s), 7.75 (1H, s), 8.06 (2H, s), 3.68 (1H, m), 1.64 (2H, br.d, J=5.6Hz)...

Synthetic example 3

[0069] Synthesis example 3 (polyQ 2 Synthesis)

[0070] The product obtained in the same manner as in Synthesis Example 2 above (Q2 -CH 2 2.13 g (4.82 mmol) of HMA) and 0.872 g (5.79 mmol) of tert-butyldimethylsilyl chloride were dissolved in dry DMF (5 mL), and imidazole was added to the resulting solution while stirring at room temperature. 0.82 g (12.0 mmol), and after stirring at room temperature for 10 hours, saturated sodium bicarbonate water was added to stop the reaction, followed by extraction with hexane. After drying the obtained organic layer, it was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain a colorless oily product [Q 2 (OSi)-CH 2 -HMA] 2.68g (yield over 99%).

[0071] The resulting product [Q 2 (OSi)-CH 2 -HMA] 1 H-NMR data are as follows.

[0072] 1 H-NMR (400MHz; CDCl 3 )δ (ppm) = 8.76 (1H, dd, 2, 4Hz), 8.41 (1H, dd, 2, 9Hz), 7.35 (1H, s), 7.32 (1H, dd, 4, 9Hz), 6.08 (1H, br.s), 5.55 (1H, quintet, 1Hz), 4.91 (2H, s...

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Abstract

This invention provides a luminescent organic polymer metal complex represented by polyQ M K n-1 (1) which is obtained by the reaction of a polymer ligand (polyQ) with an 8-hydroxyquinoline derivative introduced to its side chain through a spacer group, an 8-hydroxyquinoline derivative ligand (K) and a divalent to tetravalent metal ion (M n+ ) wherein the 8-hydroxyquinoline derivative ligand (K) has a bulky substituent. This invention also provides a luminescent organic polymer metal complex composition comprising said luminescent organic polymer metal complex and additionally a low-molecular-weight ligand and a process for producing the same.

Description

technical field [0001] The present invention relates to a novel luminescent organic polymer metal complex (or "coordination compound") and a luminescent organic polymer metal complex composition capable of wet film formation comprising the organic polymer metal complex and its production The method, in particular, relates to a light-emitting organic polymer metal complex useful as a light-emitting layer material of an organic electroluminescence element (organic EL element), a light-emitting organic polymer metal complex composition capable of wet film formation, and a production method thereof . Background technique [0002] Organic EL elements are expected to be used in displays such as televisions, personal computers, and series computers, as well as backlights of liquid crystal display devices, various advertising towers, and display lights, due to the possibility of producing surface-emitting, large-area light-emitting elements. Applied in many uses. [0003] Especial...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F8/42C08F20/36C09K11/06H05B33/14
Inventor 工藤一秋小林恭高山俊雄佐野弘
Owner NIPPON LIGHT METAL CO LTD
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