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Dione pyrrolo-pyrrole copolymer red electroluminescent material and preparation method and application thereof

A technology of diketopyrrolopyrrole and copolymer electricity, applied in the field of electroluminescent materials, can solve the problems of low luminous efficiency of devices, low external quantum efficiency of PLED devices, concentration quenching, etc., and achieve good electron transport ability, excellent Effects of improving hole transport ability and electroluminescent performance

Inactive Publication Date: 2013-01-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(2) When the red light material is in the solid film state, due to the strong Л-Л interaction or strong charge transfer characteristics, the concentration quenching effect often occurs, resulting in low luminous efficiency of the device.
(3) Most red light materials are prepared in the form of doping PLED devices, but the doping system must seek a balance between color purity and luminous efficiency. The mutual constraints of the two competing factors make it difficult for the device to achieve both color purity and luminous efficiency. good condition
(4) The energy level difference between the excited state and the excited state of red light materials is small, and the non-radiative inactivation of excited state dye molecules is more significant, so it is generally difficult for red light materials to achieve high fluorescence quantum efficiency
However, the prepared PLED devices have problems such as low external quantum efficiency and poor color purity.

Method used

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  • Dione pyrrolo-pyrrole copolymer red electroluminescent material and preparation method and application thereof
  • Dione pyrrolo-pyrrole copolymer red electroluminescent material and preparation method and application thereof
  • Dione pyrrolo-pyrrole copolymer red electroluminescent material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of 3,6-bis(4-benzaldehyde ethylene glycol acetal)pyrrolo[3,4-c]pyrrole-1,4-dione (compound 2 for short)

[0055] Sodium metal (1.472mg, 64mmol) and anhydrous ferric chloride (74mg, 0.455mmol) were added to 40ml of dry tert-amyl alcohol and reacted at 100°C for 1h until the sodium was completely dissolved. Add p-cyanobenzaldehyde ethylene glycol acetal (7g, 40mmol) in the reaction system, then slowly drop diisopropyl succinate (3.232g, 16mmol, be dissolved in 20ml tert-amyl alcohol in advance), the reaction system gradually Turn into a deep red viscous shape, pay attention to strengthen the stirring. After the dropwise addition, the constant temperature reaction was continued at 100°C for 24h, and a large amount of red solid was formed. After being cooled to room temperature, the reaction mixture was poured into a mixed solvent of 16ml glacial acetic acid and 200ml methanol, and the resulting mixture was filtered after standing still for several hours, and t...

Embodiment 2

[0057] Preparation of 2,5-dioctyl-3,6-bis(4-benzaldehyde ethylene glycol acetal)pyrrolo[3,4-c]pyrrole-1,4-dione (compound 3 for short)

[0058] Compound (2) (3.456g, 8mmol), potassium tert-butoxide (1.975g, 17.2mmol) was added to 80ml of dried N-methylpyrrolidone (NMP), stirred at 60°C for 1h, and then bromo n-octane (9.264g, 48mmol, pre-dissolved in 20ml NMP). React at constant temperature at 60°C for 24h, cool to room temperature, filter, add 50ml ethyl acetate to the filtrate, wash with water three times, and wash with anhydrous MgSO 4 After drying, filtering and rotary evaporation to remove the solvent, the crude product was separated by column chromatography (silica gel, ethyl acetate / petroleum ether 1:5). The resulting solid was recrystallized from dichloromethane / methanol to obtain 2.414 g of orange crystals (yield 46%). m.p.=130-131℃. 1 H NMR (400MHz, CDCl 3 ): δ7.81(d, 4H), 7.62(d, 4H), 5.87(s, 1H), 4.14-4.04(m, 8H), 3.70(t, 4H), 1.54(br, 4H), 1.21( br, 20H), 0.8...

Embodiment 3

[0060] Preparation of 2,5-dioctyl-3,6-di(4-benzaldehyde)pyrrolo[3,4-c]pyrrole-1,4-dione (referred to as compound 4)

[0061] Compound (3) (1.968g, 3mmol) was added to a mixed solvent of 30ml tetrahydrofuran and 15ml hydrochloric acid solution (2mol / l), and reacted at 60°C for 2h. Cool to room temperature, add 30ml ethyl acetate, wash with water three times, the organic layer is dried with anhydrous magnesium sulfate, filter, rotary evaporation removes solvent, the obtained crude product is recrystallized with dichloromethane / methanol to obtain 1.67g purple-black solid (yield 98 %). m.p.=128-130℃. 1 H NMR (400MHz, CDCl 3 ): δ10.08(s, 2H), 8.03-7.94(m, 8H), 3.74(t, 4H), 1.54(br, 4H), 1.18(br, 20H), 0.82(t, 6H).Anal. Calcd for C 36 h 44 N 2 o 4 :C,76.02;H,7.75;N,4.93.Found:C,76.10,H,7.85,N,4.97.

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Abstract

The invention discloses a dione pyrrolo-pyrrole copolymer red electroluminescent material and a preparation method and application thereof. The method introduces dione pyrrolo-pyrrole (DPP), hydroquinone ether and para-dicyano-benzene constitutional units into a main polymer chain to prepare a series of copolymer electroluminescent materials (PCA). A copolymer of the invention has excellent hole and electronic transporting properties at the same time and can be applied to preparing polymer red electroluminescent devices (PLED). The DDP copolymer prepared by the method serving as the red electroluminescent material not only has good solubility and can be easily prepared into high-quality organic films through spin coating, but also has the advantages of high luminous efficiency, high brightness, good current carrier mobility, good color purity, emission of pure saturated red light, low device driving voltage, good stability and the like.

Description

technical field [0001] The invention relates to an electroluminescent material, in particular to an electroluminescent red light material of a diketopyrrolopyrrole copolymer, a preparation method and an application thereof. Background technique [0002] Since no organic material that can effectively emit white light has been found, the current PLED technology is based on the superposition of the three primary colors of red, green, and blue. Blue primary color materials are very important. High-performance green and blue light materials can already meet the requirements of PLED technology, but the relative lack of red light materials has seriously restricted the development of PLED [Sun Xiaobo, Liu Yunqi, Yu Gui, etc. Science Bulletin, 2003, 48(23): 2402]. [0003] The main reasons for the shortage of red light-emitting materials are as follows: (1) The band gap energy of red light-emitting materials must be narrow enough, otherwise short-wavelength stray light will easily a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C08G61/12H01L27/32
Inventor 曹德榕乔智林水木
Owner SOUTH CHINA UNIV OF TECH
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