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Bi(phenylpyridine) fluorene derivatives and binuclear liquid crystal polarized cyclometalated platinum complex

A platinum complex, pyridine phenyl technology, applied in the field of liquid crystal polarized organic light-emitting materials, can solve the problem of low luminous efficiency and luminous brightness of liquid crystal polarized OLEDs, restricting the development and application of liquid crystal polarized light-emitting diodes, and disadvantageous high-efficiency, high-brightness liquid crystals problems such as backlight source, to achieve the effect of easy synthesis and purification, easy product, good liquid crystal performance and polarized luminescence performance

Active Publication Date: 2011-02-16
XIANGTAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main problems of liquid crystal polarized luminescent materials are: (1) Compared with traditional OLEDs, liquid crystal polarized OLEDs have low luminous efficiency and luminous brightness, which is not conducive to the application of high-efficiency, high-brightness liquid crystal backlights; (2) reports Liquid crystal polarized organic electroluminescent materials are only fluorescent materials; and liquid crystal polarized organic electrophosphorescent materials have not been reported in the literature
This restricts the development and application of liquid crystal polarized light-emitting diodes; (3) There are few types of liquid crystal polarized light-emitting materials based on heavy metal complexes, and the relationship between structure and performance needs to be further studied

Method used

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  • Bi(phenylpyridine) fluorene derivatives and binuclear liquid crystal polarized cyclometalated platinum complex
  • Bi(phenylpyridine) fluorene derivatives and binuclear liquid crystal polarized cyclometalated platinum complex
  • Bi(phenylpyridine) fluorene derivatives and binuclear liquid crystal polarized cyclometalated platinum complex

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Embodiment 1

[0047] Synthesis of 2-(4'-bromophenyl)-5-(alkoxymethyl)pyridine

[0048]

[0049] 1.1 Synthesis of 2-(4'-bromophenyl)-5-(butoxymethyl)pyridine

[0050] In a 100mL three-necked flask, add 5.0g (25mmol) 4-bromophenylboronic acid ester, 6.1g (25mmol) 2-bromo-5-(butoxymethyl)pyridine, 0.58g (0.5mmol) Pd(PPh 3 ) 4 , 15mL 2M K 2 CO 3 Solution, 30mL of toluene and 15mL of ethanol were reacted at 80°C for 24h under the protection of nitrogen. After cooling, the reaction solution was poured into saturated NH 4 Cl solution, extracted with dichloromethane, the extract was washed with water, anhydrous Na2SO 4 After drying, distilling off the solvent, and column separation (petroleum ether / ethyl acetate=20:1), 6.8 g of white solid was obtained. Yield 85.6%. 1 H NMR (400MHz, CDCl 3 , TMS), 8.65 (s, 1H), 7.90-7.89 (d, J=8.4Hz, 2H), 7.78-7.76 (d, J=7.0Hz, 1H), 7.71-7.69 (d, J=8.1Hz, 1H), 7.62-7.60(d, J=8.4Hz, 2H), 4.57(s, 2H), 4.06-4.00(t, 2H), 3.55-3.52(t, 2H), 1.70-1.60(m, 2H) ...

Embodiment 2

[0056] Synthesis of 5-(alkoxymethyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

[0057]

[0058] 2.1 Synthesis of 5-(butoxymethyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

[0059] In a 100mL three-necked flask, add 2.0g (5.4mmol) 2-(4'-bromophenyl)-5-(butoxymethyl)pyridine, 1.5g (5.9mmol) bisanalyl borate, 1.6g (16.2mmol) potassium acetate, 0.13g (0.16mmol) PdCl 2 (dppf)CH 2 Cl 2 And 60mL of dimethyl sulfoxide, reacted at 80°C for 24h under the protection of nitrogen. Cool, pour the reaction solution into 100mL water, extract with dichloromethane, wash the extract with water, anhydrous Na 2 SO 4 Drying, distillation to remove the solvent, and column separation (petroleum ether / ethyl acetate=10:1) yielded 1.2 g of off-white solid with a yield of 60.5%. 1 H NMR (400MHz, CDCl 3 , TMS), δ (ppm): 8.67 (s, 1H), 8.03-8.01 (d, J = 8.0Hz, 2H), 7.94-7.92 (d, J = 8.0Hz, 2H), 7.78 (s, 2H) , 4.57(s, 2H), 3.54-3.50(t, 2H), 1.67-1....

Embodiment 3

[0065] Synthesis of 2,7-bis[4'-(4"-alkoxymethyl-2"-pyridine)phenyl]-9,9-bis(dodecyl)fluorene

[0066]

[0067] 3.1 Synthesis of 2,7-bis[4′-(4″-butoxymethyl-2″-pyridine)phenyl]-9,9-bis(dodecyl)fluorene

[0068] In a 100mL three-necked flask, add 1.0g (2.7mmol) 2-[(4′-bromophenyl)-5-(alkoxymethyl)pyridine]-4,4,5,5-tetramethyl-1, 3,2-Dioxaborane, 0.8g (1.2mmol) 9,9-dioctyl-2,7-dibromofluorene, 93mg (0.08mmol) Pd(PPh 3 ) 4 , 15mL 2M K 2 CO 3 Solution, 30mL of toluene and 15mL of ethanol were reacted at 80°C for 24h under the protection of nitrogen. After cooling, the reaction solution was poured into saturated NH 4 Cl solution, extracted with dichloromethane, the extract was washed with water, anhydrous Na 2 SO 4 After drying, distilling off the solvent, and column separation (petroleum ether / ethyl acetate=10:1), 0.89 g of white solid was obtained after drying, with a yield of 75.6%. 1 H NMR (400MHz, CDCl 3 , TMS), 8.70(s, 2H), 8.15-8.13(d, J=8.2Hz, 4H), 7.83-7.81(m, 1...

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Abstract

The invention provides synthesis of a binuclear liquid crystal polarized cyclometalated platinum complex by using 2,7-bi[4'-(4''-alkoxymethyl-2''-pyridine)-phenyl]-9,9-bi(dodecyl) fluorene as cyclomedtalating ligand and bi[(4-dodecoxy) benzoyl]methane as anionic ligand, and research of polarized fluorescence and liquid crystal performance thereof. In the method, alkoxymethyl is introduced to the 5-position of a pyridine ring of the traditional cyclomedtalating ligand 2-phenylpyridine molecule; a C N cyclomedtalating ligand of double alkoxy chain with dual coordination center and liquid crystal performance through fluorene bridge connection is constructed; a novel binuclear cyclometalated platinum complex is synthesized by using the bi[(4-dodecoxy) benzoyl]methane as the anionic ligand and the 2,7-bi[4'-(4''-alkoxymethyl-2''-pyridine)-phenyl]-9,9-bi(dodecyl) fluorene liquid crystal material as the cyclomedtalating ligand. Compared with the traditional cyclometalated platinum luminescence material using the functional phenylpyridine as the cyclomedtalating ligand, the binuclear liquid crystal polarized cyclometalated platinum complex not only has high-efficiency luminescence performance, but also has good liquid crystal performance and polarized fluorescence performance. The binuclear liquid crystal polarized cyclometalated platinum complex of the invention provides a new way for obtaining the organic electrophosphorescent material 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 2,7-bis[4′-(4″-alkoxymethyl-2″-pyridine)phenyl]-9,9-bis(deca Synthesis and Photophysical, Liquid Crystal and Polarized Fluorescent Properties of Binuclear Cyclometallic Platinum Complexes with Dialkyl)fluorene as Cyclometallic Ligand and Bis[(4-Dodecyloxy)benzoyl]methane as Anionic Ligand . Background technique [0002] Since the Dyreklev research group first applied organic polarized light-emitting materials to organic electroluminescent devices (OLEDs) in 1995, [1] Due to the advantages of small size, light weight, active light emission, high luminous brightness, and no need for polarizers, liquid crystal polarized OLEDs can be directly used as background light sources for liquid crystal displays (LCDs). New Research Hotspots in the Field [1-8] . [0003] The key to realize the practical application of liquid crystal polarized...

Claims

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Application Information

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IPC IPC(8): G02F1/13357C09K19/34C09K19/40H01L51/54C09K11/06C07F15/00C07D213/30
Inventor 朱卫国王亚飞刘煜朱美香
Owner XIANGTAN UNIV
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