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D-A-D cyclometalated iridium complex near-infrared luminous material based on aryl quinoxaline and application

A technology of D-A-D and iridium complexes, which can be applied to luminescent materials, compounds containing elements of group 8/9/10/18 of the periodic table, indium organic compounds, etc., and can solve problems such as low luminous efficiency and unclear structure-activity relationship , to achieve the effects of simple synthesis steps, easy purification, good solubility and film-forming properties

Inactive Publication Date: 2019-01-04
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Aiming at the problems that the current near-infrared luminescent materials of cyclometal iridium (III) complexes generally have low luminous efficiency and unclear structure-activity relationship, the present invention develops a class of D-A-D cyclometal iridium complexes based on aryl-quinoxaline and Its application in near-infrared polymer electroluminescent diodes

Method used

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  • D-A-D cyclometalated iridium complex near-infrared luminous material based on aryl quinoxaline and application
  • D-A-D cyclometalated iridium complex near-infrared luminous material based on aryl quinoxaline and application
  • D-A-D cyclometalated iridium complex near-infrared luminous material based on aryl quinoxaline and application

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Preparation of D-A-D Cyclometallic Iridium Complex Ir-1 Based on Arylquinoxaline

[0049] The synthetic route of iridium complex Ir-1 is as follows:

[0050]

[0051] Synthesis of Intermediate 1

[0052] In a 100mL single-necked bottle, add 1,2-phenylenediamine (325mg, 3.00mmol), 3,6-dibromo-9,10-phenanthrenequinone (1g, 2.73mmol) and absolute ethanol (30mL), acetic acid (1mL), heated at 80°C, stirred at reflux for 4h, and a large amount of yellow-green solid precipitated. Cool to room temperature, filter with suction, wash the filter cake with absolute ethanol (10×3 mL) and vacuum-dry for 3 hours to obtain 1.19 g of a yellow-green solid with a yield of 91%, which is directly put into the next reaction.

[0053] Synthesis of Intermediate 2

[0054] In a 100mL two-necked flask, sequentially add intermediate 1 (500g, 1.14mmol), (4-hexylthienyl)tributyltin (1.56g, 3.42mmol), tetrakis(triphenylphosphine)palladium (40mg, 0.034mmol ), toluene (20mL), heated to 80°C und...

Embodiment 2

[0059] Preparation of D-A-D Cyclometallic Iridium Complex Ir-2 Based on Arylquinoxaline

[0060] The synthetic route of iridium complex Ir-2 is as follows:

[0061]

[0062] Synthesis of Intermediate 3

[0063] In a 100mL two-necked flask, intermediate 1 (500g, 1.14mmol), triphenylamine 4-boronate (824mg, 2.85mmol), tetrakis(triphenylphosphine) palladium (40mg, 0.034mmol) were added in turn in Example 1 ), 2mol / L potassium carbonate solution (5mL), absolute ethanol (1mL), toluene (25mL), under nitrogen atmosphere, heated to 80°C, and stirred for 12h. The toluene was distilled off under reduced pressure, and the remaining liquid was extracted with dichloromethane, washed with water, anhydrous MgSO 4 After drying and filtering, the filtrate was distilled off under reduced pressure to remove the solvent, and the residue was separated and purified through a silica gel column using a mixed solution of dichloromethane and petroleum ether (1 / 2, V / V) as an eluent to obtain 716 mg...

Embodiment 3

[0067] Preparation of D-A-D Cyclometallic Iridium Complex Ir-3 Based on Arylquinoxaline

[0068] The synthetic route of iridium complex Ir-3 is as follows:

[0069]

[0070] Synthesis of Intermediate 4

[0071] In a 100mL two-necked flask, add 4-triphenylamine borate (1.40g, 4.70mmol), 4,5-dibromo-o-phenylenediamine (0.50g, 1.88mmol), tetrakis(triphenylphosphine) palladium ( 130mg, 0.029mmol), 2mol / L potassium carbonate solution (8mL), toluene (20mL), under nitrogen atmosphere, heated to 80°C, and stirred for 12h. The toluene was distilled off under reduced pressure, and the remaining liquid was extracted with dichloromethane, washed with water, anhydrous MgSO 4 After drying and filtering, the filtrate was distilled off under reduced pressure to remove the solvent, and dried in vacuo for 3 hours to obtain 894 mg of white solid with a yield of 80%. Because the product is extremely sensitive to oxygen, it was directly put into the next reaction without purification.

[0072...

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Abstract

The invention discloses a D-A-D cyclometalated iridium complex near-infrared luminous material based on aryl quinoxaline. The near-infrared cyclometalated iridium (III) complex comprises a D-A-D C^N cyclometalated ligand taking aryl quinoxaline as an electron acceptor (A) unit and an electron-rich substituent group as an electron donor (D) unit, and an acetylacetone, dibenzoyl methane and pyridinecarboxylic acid auxiliary ligand. The material can emit strong near-infrared light with luminous wavelength greater than 700nm and is high in fluorescence quantum efficiency; an aggregation state isadjustable; the highest external quantum efficiency of a doped polymer electroluminescent device reaches 6.2%; and the highest irradiance of the device is 1416 microwatts / Sr / cm<2>.

Description

technical field [0001] The invention relates to the technical field of near-infrared luminescent materials, in particular to a class of arylquinoxaline-based D-A-D cyclometal iridium complex near-infrared luminescent materials and their application. Background technique [0002] Near-infrared luminescence (700-2500nm), thanks to its strong penetrating power, has shown unparalleled advantages in the fields of military, communication, medical treatment and phototherapy. At present, commonly used near-infrared luminescent materials are roughly divided into organic luminescent materials, inorganic There are three categories of luminescent materials and organic-inorganic composite luminescent materials. Among them, organic near-infrared light-emitting materials mainly include small organic molecules, polymers and metal complexes. According to the different luminescence mechanism, it can be divided into fluorescent materials and phosphorescent materials. The early reported near-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 朱卫国游财发刘邓辉王亚飞刘煜朱梦冰朱美香
Owner CHANGZHOU UNIV
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