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Cyclic metal platinum complex liquid crystal polarized luminescent material and its application

A technology of platinum complexes and luminescent materials, which is applied in the field of liquid crystal polarized luminescent materials and cyclometal platinum complexes, can solve the problems of low luminous efficiency and luminous brightness, no literature reports, unfavorable liquid crystal backlight, etc., and achieve high luminescence Efficiency, ease of synthesis and purification, and simple synthesis process

Inactive Publication Date: 2011-12-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The main problems of liquid crystal polarized organic electroluminescent materials and their OLEDs are: (1) the maximum luminous efficiency compared with traditional OLEDs is 19%, and the luminous brightness is 100000cd / m 2 Compared with liquid crystal polarized OLED, the luminous efficiency and luminous brightness are low, which is not conducive to being used as a high-efficiency, high-brightness liquid crystal backlight; (2) the reported liquid crystal polarized organic electroluminescent materials are only fluorescent materials; and liquid crystal polarized organic electroluminescent materials Phosphorescent materials have not been reported in the literature
However, liquid crystal polarized organic electrophosphorescent materials have not been reported in the literature

Method used

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  • Cyclic metal platinum complex liquid crystal polarized luminescent material and its application
  • Cyclic metal platinum complex liquid crystal polarized luminescent material and its application
  • Cyclic metal platinum complex liquid crystal polarized luminescent material and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Synthesis of 2-(4'-alkoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0069]

[0070] 1.1 Synthesis of 4-butoxybromobenzene

[0071] In a 250mL single-necked bottle, add 6.9g (39.6mol) p-bromophenol, 7.9g (57.3mol) 1-bromobutane, 15.0g (108.7mol) anhydrous potassium carbonate, 0.5g (4.2mol) potassium iodide and 100mL acetone , at N 2 Reflux for 24h under atmosphere. Cool, filter with suction, and remove acetone under reduced pressure. The residue is separated by column chromatography using petroleum ether as the eluent to obtain 7.5 g of a colorless liquid with a yield of 82.9%. 1 H NMR (400MHz, CDCl 3 , TMS), δ (ppm): 7.37-7.34 (m, 2H), 6.79-6.76 (m, 2H), 3.93-3.90 (t, 2H), 1.79-1.72 (m, 2H), 1.53-1.43 (m , 2H), 0.99-0.95(t, 3H).

[0072] 1.2 Synthesis of 4-octyloxybromobenzene

[0073] The method is the same as 1.1 to obtain a colorless liquid with a yield of 82.9%. 1 H NMR (400MHz, CDCl 3 , TMS), δ (ppm): 7.37-7.34 (m, 2H), 6.79-6.76 (m, 2H), 3.92-3.89 ...

Embodiment 2

[0087] Synthesis of 2-(3'-fluoro-4'-alkoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane

[0088]

[0089] 2.1 Synthesis of 3-fluoro-4-octyloxybromobenzene

[0090] In a 250mL three-necked flask, add 5.0g (26.2mmol) 2-fluoro-4-bromophenol, 6.0g (31.1mmol) 1-bromo-n-octane, 15.0g (108.7mmol) anhydrous K 2 CO 3 , a catalytic amount of potassium iodide and 80 mL of acetone were refluxed for 24 h under the protection of nitrogen. Cool, filter with suction, and remove acetone under reduced pressure. The residue is separated by column chromatography with petroleum ether as eluent to obtain 4.8 g of colorless liquid with a yield of 60.5%. 1 H NMR (400MHz, CDCl 3 , TMS), δ (ppm): 7.25-7.22 (d, J = 12.0Hz, 1H), 7.18-7.16 (d, J = 8.0Hz, 1H), 6.86-6.82 (t, 1H), 4.02-3.99 ( t, 2H), 1.83-1.79(m, 2H), 1.465-1.29(m, 10H), 0.9-0.87(t, 3H).

[0091] 2.2 Synthesis of 3-fluoro-4-dodecyloxybromobenzene

[0092] The method is the same as 2.1 to obtain a light yellow liquid with a yield of ...

Embodiment 3

[0102] Synthesis of 2-bromo-5-(alkoxymethyl)pyridine

[0103]

[0104] 3.1 Synthesis of 2-bromo-5-pyridinecarbaldehyde

[0105] In a 500mL three-necked flask, add 6.0g (25.3mmol) of 2,5-dibromopyridine and 200mL of anhydrous ether, under nitrogen protection, at -78.5°C, slowly add 16mL (25.6mmol) of n-butyllithium (1.6mol / L), after reacting for 30min, add 2.2mL DMF dropwise, continue to react for 2h, then warm up to room temperature for 1h, add 50mL water to terminate the reaction. The reaction solution was adjusted to PH=7 with dilute HCl, distilled off ether, and then distilled off with CH 2 Cl 2 extraction. The extract was washed with water, dried over anhydrous magnesium sulfate, and separated by a column (petroleum ether: ethyl acetate = 6:1) to obtain 2.21 g of a white solid. Yield 47.0%. m.p.: 104-110°C. 1 HNMR (400MHz, CDCl 3 , TMS), 10.09(s, 1H), 8.82(s, 1H), 8.03-8.00(d, J=10.6Hz, 1H), 7.69-7.67(d, J=8.1Hz, 1H).

[0106] 3.2 Synthesis of 2-bromo-5-pyridin...

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Abstract

The invention discloses a cyclometal platinum complex liquid crystal polarized luminescence material and its application, which is a kind of cyclometal platinum complex liquid crystal polarized light emission based on a phenylpyridine derivative liquid crystal material as a cyclometal ligand and acetylacetone as an anion ligand Material. The present invention introduces an alkoxy group at the 4-position of the benzene ring of the traditional ring metal ligand 2-phenylpyridine molecule, and introduces an alkoxymethyl group at the 5-position of the pyridine ring to form a liquid crystal. The C^N ring metal ligand of the double alkoxy chain; or on this basis, on the 3-position of the benzene ring, introduce fluorine to form the C^N of the fluorine-containing double alkoxy chain with liquid crystal properties Cyclometallic ligands, and then using acetylacetone as anionic ligands, a new class of cyclometallic platinum complexes with phenylpyridine derivative liquid crystal materials as cyclometallic ligands was synthesized. Compared with the traditional cyclometal platinum luminescent material in which the functionalized phenylpyridine is the cyclometal ligand, the invention not only has high-efficiency luminescence performance, but also has good liquid crystal performance and polarized luminescence performance. The invention provides a new approach for obtaining organic electrophosphorescent materials with liquid crystal polarization.

Description

technical field [0001] The invention relates to the field of liquid crystal polarized organic luminescent materials, in particular to a class of 2-(4'-alkoxyphenyl)-5-(alkoxymethyl)pyridine or 2-(3'-fluoro-4'-alkane Cyclic metal ligands of oxyphenyl)-5-(alkoxymethyl)pyridine, liquid crystal polarized luminescent materials of cyclometal platinum complexes composed of such ligands and acetylacetonate anion ligands, and applications thereof. Background technique [0002] In 1995, Dyrekley et al. used the stretching method for the first time to obtain an organic electroluminescent diode with an external quantum efficiency of 0.1%, a driving voltage of 2 volts, and a polarization rate of 2.4, which directly emits polarized light, creating a liquid crystal polarized organic electroluminescent material. The New Situation of Its Research on Organic Light Emitting Diode (OLED) [1] . Due to the advantages of small size, light weight, active light emission, high luminous brightness, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/30C09K11/06C09K19/40C09K19/34C07F15/00H01L51/54H01L51/50
Inventor 朱卫国王亚飞刘煜朱美香
Owner XIANGTAN UNIV
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