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Intramolecular charge transfer type red luminescent material and preparation and application thereof

A technology of charge transfer and red light emission, which is applied to the preparation of the above-mentioned materials, and the application of the above-mentioned materials in organic electroluminescent devices, to achieve the effects of good electron transport performance, simple separation, and simple device preparation process

Inactive Publication Date: 2006-04-26
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, there are still relatively few non-doped host red luminescent materials, and it is still very important to synthesize new host luminescent materials with high efficiency and practical applications.

Method used

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  • Intramolecular charge transfer type red luminescent material and preparation and application thereof
  • Intramolecular charge transfer type red luminescent material and preparation and application thereof
  • Intramolecular charge transfer type red luminescent material and preparation and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1: 2,3-dicyano-5,6-bis-(4'-diphenylamino)-phenyl-pyrazine (compound 1)

[0040]

[0041] Step a: In a 100ml three-necked flask, place 4,4'-dibromodiphenylethanedione (2mmol) and 4-tri-n-butyltinphenyl-diphenylamine (4mmol) in about 20ml redistilled N, In N-dimethylformamide, then add the catalyst Pd (PPh 3 ) 2 Cl 2 (0.2mmol) (the catalyst can also be Pd(PPh 3 ) 4 or PhCH 2 Pd(PPh 3 ) 2Cl), under normal pressure, nitrogen atmosphere, temperature controlled at 80-100° C., heated to reflux for about 24 hours; after the reaction stopped, cooled to room temperature. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent: dichloromethane / petroleum ether 1:1 v / v) to obtain an orange-red solid (yield 90%).

[0042] Mass spectrum (MALDI-TOF-MS): m / z calculated value 696.28, measured value 696.3 (M + );

[0043] H NMR spectrum ( 1 H-NMR) (400MHz, CDCl 3 , ppm): δ=8.04(d, J...

Embodiment 2

[0050] Example 2: 6,7-dicyano-2,3-bis-(4'-diphenylamino)-phenyl-quinoxaline (compound 2)

[0051]

[0052] The heating reflux time of step a in embodiment 1 is 16 hours, all the other conditions are the same as embodiment 1, the product 4,4'-(4'-diphenylamino)-diphenylethanedione (0.2mmol) obtained by reaction, 4,5-diamino-phthalocyanine (0.2 mmol) and acetic acid (10 mL) were added into a 50 ml three-neck flask and refluxed for 12 hours under nitrogen atmosphere. After cooling and filtering, the obtained red precipitate was precipitated with dichloromethane and petroleum ether to obtain pure product 2 (yield 93.7%).

[0053] Mass Spectrum (MALDI-TOF-MS) m / z: calculated value 818.32; measured value 818.0 (M + );

[0054] H NMR spectrum ( 1 H-NMR) (400MHz, CDCl 3 , ppm): δ=8.63(s, 2H), 7.70(d, J=8.3Hz, 4H), 7.63(d, J=8.3Hz, 4H), 7.53(d, J=8.5Hz, 4H), 7.28 -7.32 (m, 8H), 7.14-7.16 (m, 12H), 7.07 (t, 4H).

[0055] NMR spectrum ( 13 C-NMR) (100MHz, CDCl 3 , ppm): δ=157....

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Abstract

The present invention relates to serial intermolecular charge transfer type red light emitting materials with unparallel dipole system and its preparation process. The serial red light emitting materials are prepared with triphenylamine and diphenyl naphthylamine with hole transferring radical or their derivative as electron donor and nitrile group with powerful electrophilicity as electronic receptor and through simple Stille coupling reaction and condensation. Their molecular structure, electrochemical properties and physical optical property have been researched and characterized, and devices with the material as light emitting layer and electron transferring layer have been prepared. Tests show that these materials are active red light emitting materials with excellent application foreground.

Description

technical field [0001] The invention relates to an intramolecular charge transfer type red luminescent material with a non-parallel dipole system. [0002] The invention also relates to a method for the preparation of the aforementioned materials. [0003] The present invention also relates to the application of the above materials in organic electroluminescent devices. Background technique [0004] Since Kodak Corporation (Tang, C.W.; Vanslyke, S.A. Appl. Phys. Lett. 1987, 51, 913.) launched an efficient organic electroluminescent device in 1987, with its adjustable luminous color, high brightness, high efficiency, Excellent characteristics such as wide viewing angle, low power consumption, simple preparation process, and the ability to prepare curved and flexible screens, as well as potential applications in the field of large-area flat-panel full-color displays, have attracted widespread attention from the scientific community and the active participation of internationa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H05B33/00
Inventor 刘云圻陈仕艳徐新军于贵孙晓波邱文丰马永强朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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