Cyclometalated platinum complexes liquid crystal polarized luminescent material and application thereof

A technology of platinum complexes and luminescent materials, applied in the field of liquid crystal polarized organic luminescent materials, can solve the problems of low luminous efficiency and luminous brightness, no literature reports, unfavorable liquid crystal backlight, etc., achieve high luminous efficiency, easy synthesis and The effect of simple purification and synthesis process

Inactive Publication Date: 2009-12-30
XIANGTAN UNIV
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  • Abstract
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  • 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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  • Cyclometalated platinum complexes liquid crystal polarized luminescent material and application thereof
  • Cyclometalated platinum complexes liquid crystal polarized luminescent material and application thereof
  • Cyclometalated platinum complexes liquid crystal polarized luminescent material and application thereof

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) of p-bromophenol, 7.9g (57.3mol) of 1-bromobutane, 15.0g (108.7mol) of anhydrous potassium carbonate, 0.5g (4.2mol) of potassium iodide and 100mL of 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, ...

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 cyclometalated platinum complexes liquid crystal polarized luminescent material which is based on that phenylpyridine derivatives liquid crystal material is used as cyclomedtalating ligand and acetylacetone is used as anion ligand, and an application thereof. The material is prepared by the following steps: introducing alkoxy to benzene C-4 of the traditional cyclomedtalating ligand phenylpyridine C-2 and introducing alkoxymelthyl to pyridine C-5 to form C^N cyclomedtalating ligand of dialkoxy chain with liquid crystalline properties or in addition introducing fluorine to benzene C-3 to form fluorine-containing C^N cyclomedtalating ligand of dialkoxy chain with liquid crystalline properties, and then using acetylacetone as anion ligand to synthesizing a kind of new cyclomedtalating platinum complex which adopts phenylpyridine derivatives as cyclomedtalating ligand. Compared with the traditional cyclomedtalating platinum luminescent material which adopts functionalized phenylpyridine as cyclomedtalating ligand, the material of the invention has not only high-efficiency luminous performance, but also good liquid crystalline properties and polarisation luminous performance. The material of the invention provides a new way to obtain liquid crystal polarization organic electrophosphorescent material.

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 Applications(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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