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Aggregation-induced luminescent and piezochromism luminescent near-infrared ion-type iridium (III) complex and application thereof

A technology of aggregation-induced luminescence and piezochromism, which is applied in the direction of color-changing fluorescent materials, compounds containing elements of group 8/9/10/18 of the periodic table, luminescent materials, etc., can solve low-concentration doping, low luminous efficiency, There are few types of near-infrared luminescent materials, etc., to achieve the effects of mild synthesis conditions, high yield, good film formation and solubility

Active Publication Date: 2019-01-18
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] Aiming at the problems that there are few types of near-infrared luminescent materials for cyclometal iridium (III) complexes, the luminous efficiency is generally low, and low concentrations need to be doped in the host material, etc., the present invention is committed to developing a class of pyrazino[2, 3-f][1,10]phenanthroline derivatives as electron-accepting units (A), electron-rich aromatic amines as electron-donating units, D-A (donor-acceptor) type N^N auxiliary ligands and their ionic forms Iridium(III) complexes, which have dual characteristics of aggregation-induced phosphorescence emission and piezochromic emission

Method used

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  • Aggregation-induced luminescent and piezochromism luminescent near-infrared ion-type iridium (III) complex and application thereof
  • Aggregation-induced luminescent and piezochromism luminescent near-infrared ion-type iridium (III) complex and application thereof
  • Aggregation-induced luminescent and piezochromism luminescent near-infrared ion-type iridium (III) complex and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Ionic Iridium(III) Complex (2Fppy) 2 Ir + [dppz-(11,12-diTPA) 2 ]PF 6 ﹣ preparation of

[0051] The synthetic route of this iridium (III) complex is as follows:

[0052]

[0053] Synthesis of Intermediate 1

[0054] 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. Cool to room temperature, remove toluene by distillation under reduced pressure, and extract the remaining liquid with dichloromethane, wash with water, anhydrous MgSO 4 After drying and filtering, the solvent was distilled off under reduced pressure 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 purificat...

Embodiment 2

[0062] Ionic iridium(III) complexes (ppy) 2 Ir + [dppz-(11,12-diTPA) 2 ]PF 6 ﹣ preparation of

[0063] The synthetic route of this complex is as follows:

[0064]

[0065] Synthesis of Intermediate 4

[0066] In a 100mL single-necked bottle, add 2-phenylpyridine (1.0g, 6.44mmol), iridium trichloride hydrate (IrCl 3 ·nH 2 O) (959.6mg, 3.22mmol), distilled water (5mL) and ethylene glycol monoethyl ether (15mL), heated to 100°C under nitrogen protection, and stirred for 24h. The reaction system was cooled to room temperature, distilled water (5 mL) was added, a large amount of yellow solid was precipitated, filtered with suction, the solid was washed several times with distilled water, petroleum ether and n-hexane successively, and dried in vacuum to obtain 1.50 g of yellow powder product with a yield of 87.0%.

[0067] Complex (ppy) 2 Ir + [dppz-(11,12-diTPA) 2 ]PF 6 ﹣ Synthesis

[0068] In a 100mL single-necked bottle, sequentially add Intermediate 4 (100mg, 0....

Embodiment 3

[0070] Photophysical properties of 11,12-bis(4-triphenylamino)dipyrido[3,2-a:2',3'-c]phenazine

[0071] Intermediate 2 is 11,12-bis(4-triphenylamino)dipyrido[3,2-a:2',3'-c]phenazine N^N ligand, and its ultraviolet-visible (UV-Vis ) absorption spectrum and fluorescence spectrum (PL) respectively as attached figure 1 and figure 2 shown. This N^N ligand was formulated as 1×10 -5 mol / L tetrahydrofuran (THF), chloroform (CHCl 3 ), dichloromethane (DCM) solution, and sequentially pipette 3mL into a quartz cuvette to test the UV-Vis and PL spectra of these solutions; prepare 10mg / mL of CHCl 3 solutions, and were spin-coated onto quartz wafers, and these films were tested for UV-Vis and PL spectra.

[0072] Depend on figure 1 It can be seen that: (1) The ligand has absorption from 250nm to 550nm and presents two characteristic absorption bands, among which, the strong absorption band from 250nm to 400nm is attributed to the charge transfer transition absorption of π→π*, while t...

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Abstract

The invention discloses an aggregation-induced luminescent and piezochromism luminescent double-characteristic ion-type iridium (III) complex near-infrared luminescent material. The ion-type iridium (III) complex comprises C-N cyclic metal ligand comprising a 2-phenylpyridine derivative, N-N auxiliary ligand of aryl pyrazine[2,3-f][1,10] phenanthroline of an electron donar-receptor (D-A) unit structure and halogen-comprising anions. The material is extremely weak in luminescence at a solution state and capable of emitting high near-infrared rays at an aggregation state and under the pressure,and can be widely applied to near-infrared electroluminescence devices and stress sensors.

Description

technical field [0001] The invention relates to a class of near-infrared luminescent materials of ionic iridium (III) complexes with dual characteristics of aggregation-induced phosphorescent emission and piezochromic luminescence, and their application in organic light-emitting diodes (OLEDs) and stress sensors, belonging to luminescent materials field. Background technique [0002] In recent years, near-infrared (700–2500 nm) luminescent materials have attracted much attention due to their potential applications in information security displays, night vision equipment, biological imaging, optical fiber communication, and medical diagnosis. At present, the reported near-infrared luminescent materials roughly include three types: inorganic luminescent materials, organic luminescent materials, and organic-inorganic composite luminescent materials. Among them, near-infrared organic light-emitting materials are mainly divided into organic small molecule fluorescent materials a...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06C09K9/02H01L51/50H01L51/54
CPCC09K9/02C09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/00
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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