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Neutral iridium complex with bidentate ligand, and preparation method and application thereof

A technology of iridium complexes and bidentate ligands, applied in the field of photoelectric functional organic materials, to avoid concentration quenching, simple synthesis steps, and improve carrier transport performance

Active Publication Date: 2014-10-08
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in order to meet the needs of commercialization, consider various market conditions, and improve the yield of devices, higher requirements are put forward for materials used in OLEDs, which gives material scientists a more difficult task

Method used

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  • Neutral iridium complex with bidentate ligand, and preparation method and application thereof
  • Neutral iridium complex with bidentate ligand, and preparation method and application thereof
  • Neutral iridium complex with bidentate ligand, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Complex Ir(Cpq) 2 Preparation of (pybz)

[0035] The reaction formula is as follows:

[0036]

[0037] 2-(4-Methylphenyl)quinoline (Cpq): Add 1.9g (12.5mmol) of o-nitrobenzaldehyde and 42.5mL of absolute ethanol into a round bottom flask, stir to dissolve it, then add 5g of iron powder ( 89.25mmol), 42.5mL of acetic acid and 21mL of distilled water, finally add a drop of concentrated hydrochloric acid, reflux for 15min (the reaction is complete as monitored by TLC) to stop the reaction, filter with suction, wash and filter with 100mL of water, collect the filtrate with CH 2 Cl 2 Extraction, the combined organic layers were separated with NaHCO 3 Aqueous and distilled water washes, anhydrous MgSO 4 Dry and concentrate to obtain anthranilaldehyde as a yellow oil. Add 5 mmol of anthranilaldehyde and 5 mmol of p-methylacetophenone to 20 mL of absolute ethanol, and then add saturated NaOH ethanol solution. The reaction mixture was heated and refluxed overnight, then ...

Embodiment 2

[0040] Complex Ir(COpq) 2 Preparation of (pybz)

[0041] The reaction formula is as follows:

[0042]

[0043] 2-(4-Methoxyphenyl)quinoline (COpq): Add 1.9g (12.5mmol) of o-nitrobenzaldehyde and 42.5mL of absolute ethanol in a round bottom flask, stir to dissolve it, and then add 5g of iron powder (89.25mmol), 42.5mL of acetic acid and 21mL of distilled water, finally add a drop of concentrated hydrochloric acid, reflux for 15min (the reaction is complete as monitored by TLC) to stop the reaction, filter with suction, wash and filter with 100mL of water, collect the filtrate with CH 2 Cl 2 Extraction, the combined organic layers were separated with NaHCO 3 Aqueous and distilled water washes, anhydrous MgSO 4 Dry and concentrate to obtain anthranilaldehyde as a yellow oil. Add 5 mmol of anthranilaldehyde and 5 mmol of p-methoxyacetophenone to 20 mL of absolute ethanol, and then add saturated NaOH ethanol solution. The reaction mixture was heated and refluxed overnight, ...

Embodiment 3

[0046] Compound Ir(Sipq) 2 Preparation of (pybz)

[0047] The reaction formula is as follows:

[0048]

[0049] 2-(4-triphenylsilylphenyl)quinoline (Sipq): Add 7.6g (50mmol) of o-nitrobenzaldehyde and 170mL of absolute ethanol into a round bottom flask, stir to dissolve it, and then add 20g of iron powder ( 357mmol), 170mL of acetic acid and 85mL of distilled water, finally add a drop of concentrated hydrochloric acid, reflux for 15min (the reaction is complete as monitored by TLC) to stop the reaction, filter with suction, wash and filter with 100mL of water, collect the filtrate with CH 2 Cl 2 Extraction, the combined organic layers were separated with NaHCO 3 Aqueous and distilled water washes, anhydrous MgSO 4 Dry and concentrate to give a yellow oil. Add 7.8mmol anthranilaldehyde and 7.8mmol p-bromoacetophenone to 30mL absolute ethanol, and then add saturated NaOH ethanol solution. The reaction mixture was heated and refluxed overnight, then cooled and filtered, ...

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Abstract

The invention relates to a neutral iridium complex with a bidentate ligand, and a preparation method and application thereof, and belongs to the technical field of photoelectric functional organic materials. The invention concretely relates to the preparation method for the neutral iridium complex with the bidentate ligand, and application of the neutral iridium complex to organic electroluminescent devices, bioimaging and biolabeling. The neutral iridium complex employs a phenylquinoline derivative as a cyclometalated ligand, and has the general structural formula of [Ir(C^N)2(N^N)]. The material is simple in synthetic steps and mild in conditions. By introducing different main-group elements for changing into different cyclometalated ligands, adjusting on photophysical properties of the complex is realized, and the complex has relatively high quantum efficiency, so that the complex has great application prospect in the field of organic photoelectric functional materials.

Description

technical field [0001] The invention belongs to the technical field of photoelectric functional organic materials, and specifically relates to a preparation method of a neutral iridium complex with a bidentate ligand and its application in organic electroluminescent devices and biological imaging and labeling. Background technique [0002] When electrons and holes recombine in organic molecules, two excited states will be generated due to the difference in electron spin symmetry, which are singlet excited state and triplet excited state. The singlet excited state is formed by non-spin symmetric excited electrons, while the triplet excited state is formed by spin symmetric excited electrons. The transition from the singlet excited state to the ground state is fluorescent emission, while the transition from the triplet excited state to the ground state is phosphorescent emission. Normally, the process of electrons from the singlet excited state to the ground state is allowed,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 赵强黄维刘淑娟许文娟徐杭董晓臣
Owner NANJING UNIV OF POSTS & TELECOMM
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