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9-pyrene based fluorene structured linear conjugated polymer derivant material and preparation method thereof

A conjugated polymer, polymer technology, used in luminescent materials, chemical instruments and methods, semiconductor/solid-state device fabrication, etc.

Inactive Publication Date: 2008-12-10
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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So far, there are no relevant literature and patent reports at home and abroad

Method used

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  • 9-pyrene based fluorene structured linear conjugated polymer derivant material and preparation method thereof
  • 9-pyrene based fluorene structured linear conjugated polymer derivant material and preparation method thereof
  • 9-pyrene based fluorene structured linear conjugated polymer derivant material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Embodiment 1: the synthesis of polymer I1 (wherein R 1 = R 2 , is n-octyl; R 3 to a hydrogen atom).

[0094] (1) 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-9-phenyl-9-pyrenylfluorene (boron acid esters 1).

[0095] 2,7-Dibromo-9-phenyl-9-pyrenylfluorene (1.3 g, 2.2 mmol) was dissolved in anhydrous and oxygen-free THF (20 mL) under anhydrous and oxygen-free conditions, and cooled to -78°C. n-Butyllithium (1.6M solution in n-hexane) (5 mL, 8 mmol) was injected dropwise into the system with a syringe, and the system was stirred at -78°C for 1.5 h. Methyl triborate (2.5mL, 2.28g, 22mmol) was quickly injected into the system with a syringe at one time. After the system was stirred at -78°C for 1.5h, the temperature was slowly raised to room temperature, and the reaction was continued for 24h. Add 2M hydrochloric acid (50 mL) to acidify for 5 h, separate the layers, extract the aqueous phase with dichloromethane or ether, dry the combined organic phases with an...

Embodiment 2

[0103] Example 2: Absorption spectra of solutions and thin films of polymer I1 (the product in Example 1), determination of photoluminescence spectroscopy.

[0104] Polymer I1 was dissolved in tetrahydrofuran solution, and the absorption and emission spectra were measured by Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer. The photoluminescence spectrum is excited by the maximum absorption wavelength (391 nm) of ultraviolet absorption. The solid film is formed by dropping the solution on a transparent glass plate after the solvent evaporates. The fluorescence quantum efficiency of the solution is measured by 10 in cyclohexane -6 The 9,10-diphenylanthracene solution of M (quantum efficiency 0.9) was used as a standard to measure, and the measured value was 93%.

[0105] The polymer I1 solution has a maximum absorption peak of 391nm in a wavelength range greater than 300nm, sharp absorption peaks at 354nm and 335nm, a shoulder at 324nm...

Embodiment 3

[0107] Embodiment 3: the synthesis of borate 2 (wherein R 3 = n-octyl)

[0108] (1) 1-(2-bromo-5-octylphenyl)pyrene

[0109] 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene (3.28g, 0.01mol) and 1,2-dibromo-4-octane Phenylbenzene (6.96g, 0.02mol) was placed in a 100mL flask with a stirring bar in advance, vacuumed, and nitrogen gas was passed three times, then oxygen-free toluene (40mL) was injected into the flask with a syringe. The mixture was heated to 80°C and stirred until the monomers were completely dissolved, and tetrakis(triphenylphosphide)palladium (Pd(PPh 3 ) 4 ) (0.01mmol) in toluene (10mL), and inject anaerobic nitrogen saturated 2M sodium carbonate solution (10mL) with a syringe. Then the system was warmed up to 90°C. After 48 hours of reaction, the temperature of the system was lowered to room temperature, and saturated sodium bicarbonate solution was added to separate the liquids. The organic phase was washed three times with dichloromethane. After the...

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Abstract

The invention relates to a linear conjugated polymer derivate material with a 9-pyrenyl fluorine structure and a preparation method thereof. The material can be applied in the plastic electronic fields such as polymer electroluminescent materials, polymer integrated circuits, polymer solar batteries, polymer thin-film transistors, polymer dye lasers, polymer nonlinear optical materials, fluorescent probes and so on. The polymer combines two high-performance systems of pyrene and fluorine together by non-conjugated means, and has the advantages that: firstly, the raw materials are low-price, and the synthetic method is simple and convenient; and secondly, the material also has obviously improved hole injection capacity, hole transmitting capacity and electronic transmitting capacity besides good solubility, thermal stability and rheologic property, and a hole injection layer, a hole transmitting layer and an electronic transmitting layer can be not required in an electroluminescent device, thereby the technique of the device is simplified. The electroluminescent device prepared by utilization of the material is satisfactory in the aspects of brightness, luminous efficiency, voltage-resistant stability and so on.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, and specifically relates to a linear conjugated polymer derivative material with a 9-pyreneylfluorene structure and a preparation method thereof. This type of material can be applied to polymer electroluminescent materials, polymer integrated circuits, polymer Organic electronics such as solar cells, polymer thin film transistors, polymer lasers, polymer nonlinear optical materials and fluorescent probes. Background technique [0002] In recent decades, the take-off of inorganic semiconductor devices has greatly promoted the rapid development of the entire electronic information technology. Driven by Moore's Law, the semiconductor industry continues to reduce the size of devices to increase integration to meet the improvement of chip performance and cost reduction, but the chip size cannot be infinitely small, and existing semiconductor devices such as transistor technology have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C09K11/06H01L51/00H01L51/54H01L51/30H01L51/46H10K99/00
CPCY02E10/549Y02B20/00
Inventor 黄维唐超徐慧
Owner NANJING UNIV OF POSTS & TELECOMM
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