Conjugated polymer photoelectric material containing amine oxide groups and application thereof

A technology of conjugated polymers and amine oxides, which is applied in luminescent materials, photovoltaic power generation, circuits, etc., can solve the problems of response speed conjugated polyelectrolyte charge mobility ions, affecting long-term stability of devices, etc., to achieve excellent electronic performance Effect of Injection/Transport Performance

Active Publication Date: 2014-04-02
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the vast majority of conjugated polyelectrolytes have freely mobile counter ions, which may be able to diffuse into the emissive layer and affect the long-term stability of the device.
In addition, the response speed of the device and the charge mobility of the conjugated polyelectrolyte are greatly affected by the ion

Method used

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  • Conjugated polymer photoelectric material containing amine oxide groups and application thereof
  • Conjugated polymer photoelectric material containing amine oxide groups and application thereof
  • Conjugated polymer photoelectric material containing amine oxide groups and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: The synthetic route of poly{2,7-[9,9'-bis(N,N-diethylhexyl-6-amine oxide)fluorene]} (PF6NO) is as follows:

[0031]

[0032] (1) Monomers 1 and 2 are prepared according to the method disclosed in the literature [Adv.Mater., 2011, 23, 1665];

[0033] (2) Preparation of poly{2,7-[9,9'-bis(N,N-diethylhexyl-6-amino)fluorene]} (PF6N)

[0034] Monomer 2,7-bis(trimethylene borate)-9,9'-bis(N,N-diethylhexyl-6-amino)fluorene (728 mg, 1 mmol), monomer 2,7 -dibromo-9,9'-bis(N,N-diethylhexyl-6-amino)fluorene (634mg, 1mmol) and 10mg tetraphenylphosphorous palladium catalyst dissolved in 10ml toluene and 5ml tetrahydrofuran In the solvent, add 4ml of 2mol / L sodium carbonate aqueous solution, under the protection of argon, reflux reaction for 48 hours, then cool to room temperature, precipitate the reaction solution in methanol to obtain the crude product, dissolve the crude product in tetrahydrofuran, pass through 0.45μm The organic filter membrane was concentrated...

Embodiment 2

[0036]Example 2: Synthesis of poly{2,7-[9,9'-bis(N,N-diethylhexyl-6-amine oxide)fluorene]co-2,5-pyridine}(PF6NO25Py)

[0037] The synthetic route is as follows:

[0038]

[0039] (1) The monomer 2,5-dibromopyridine is directly purchased from Bailingwei Company and used after recrystallization with methanol;

[0040] (2) Preparation of poly{2,7-[9,9'-bis(N,N-diethylhexyl-6-amino)fluorene]co-2,5-pyridine} (PF6N25Py);

[0041] The monomer 2,7-bis(trimethylene borate)-9,9'-bis(N,N-diethylhexyl-6-amino)fluorene (728mg, 1mmol) prepared in Example 1 , monomer 2,5-dibromopyridine (237mg, 1mmol) and 10mg tetraphenylphosphorous palladium catalysts are dissolved in the mixed solvent of 10ml toluene and 5ml tetrahydrofuran, add the sodium carbonate aqueous solution of 4ml 2mol / L, under argon Under the protection of the reflux reaction for 48 hours, then cooled to room temperature, the reaction solution was precipitated in methanol to obtain a crude product, the crude product was diss...

Embodiment 3

[0044] Example 3: Synthesis of poly{2,7-[9,9'-bis(N,N-diethylhexyl-6-amine oxide)fluorene]co-3,5-pyridine}(PF6NO35Py)

[0045] The synthetic route is as follows:

[0046]

[0047] (1) The monomer 3,5-dibromopyridine is directly purchased from Bailingwei Company and used after recrystallization with methanol;

[0048] (2) Preparation of poly{2,7-[9,9'-bis(N,N-diethylhexyl-6-amino)fluorene]co-3,5-pyridine} (PF6N35Py)

[0049] The monomer 2,7-bis(trimethylene borate)-9,9'-bis(N,N-diethylhexyl-6-amino)fluorene (728mg, 1mmol) prepared in Example 1 , monomer 3,5-dibromopyridine (237mg, 1mmol) and 10mg tetraphenylphosphorous palladium catalysts are dissolved in the mixed solvent of 10ml toluene and 5ml tetrahydrofuran, add the sodium carbonate aqueous solution of 4ml 2mol / L, under argon Under the protection of the reflux reaction for 48 hours, then cooled to room temperature, the reaction solution was precipitated in methanol to obtain a crude product, the crude product was diss...

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Abstract

Disclosed are an amine-oxide-group-containing conjugated polymer photoelectric material and application thereof. The amine-oxide-group-containing conjugated polymer photoelectric material consists of conjugated main chains and a side chain containing an amine oxide unit, and is applied in an organic photoelectric device. The material has desirable alcohol / water solubility and photoelectric properties, is suitable for making a multi-layer solution for machining a device, and meanwhile can prevent an adverse effect incurred by freely moving counter ions in a common polyelectrolyte to the device. The material may be used as a cathode interface modification layer applied in organic photoelectric devices such as light-emitting and photovoltaic devices, so as to improve performance of the devices.

Description

technical field [0001] The invention relates to the field of polymer photoelectric materials, in particular to a class of conjugated polymer photoelectric materials containing amine oxide groups and applications thereof. Background technique [0002] Since the invention of the first polymer electroluminescent diode in 1990, polymer electro-optic materials have received extensive attention from academia and industry. [0003] In order to realize high-efficiency polymer electroluminescent devices, the efficient injection of electrons and holes from the cathode and anode, respectively, is the key. Therefore, many high-efficiency polymer electroluminescent devices adopt a multi-layer device structure, that is, in addition to the light-emitting layer, it also contains one or more hole transport / injection layers or electron transport / injection layers. Therefore, in addition to the development of excellent light-emitting materials, the development of excellent electron transport / i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/02C08G61/10C08G61/12C09K11/06H01L51/54
CPCC08G2261/411C08G61/122H01L51/0037C08G61/12H01L51/0043C08G2261/124C08G2261/3142C08G2261/143Y02E10/549H01L51/0039C08G61/02H10K85/115H10K85/1135H10K85/151H10K30/30H10K50/171H10K50/16H10K30/00
Inventor 黄飞管星张凯曹镛
Owner SOUTH CHINA UNIV OF TECH
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