Host red luminous material with charge transferring structure and its prepn and application

A red-emitting, host-based technology, applied in luminescent materials, chemical instruments and methods, can solve problems such as increasing the concentration of objects, reducing device efficiency, and incomplete matching, and achieves simple preparation processes, good thermal stability, and good solubility. Effect

CN1706909AInactive Publication Date: 2005-12-14INST OF CHEM CHINESE ACAD OF SCI
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2005-12-14
Estimated Expiration
Not applicable · inactive patent

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Abstract

The present invention is host red luminous material with charge transfer structure and its preparation process. Serial red luminous materials are prepared with three kinds of excellent hole transfer radicals, carbazole, triphenylamine and phenothiazine and its substituent derivative as electron donor, with nitrile radical with strong electrophilic capacity as electron acceptor, and through double condensation reaction to form C=C double bond. The molecular structure of these red luminous materials is characterized in mass spectral analysis, nuclear magnetic resonance spectroscopy, element analysis, etc; the electrochemical property is characterized with circular volt-ampere characteristic; the physical, including optical, properties are researched in ultraviolet absorption and fluorescent spectrum; and device with the material as light emitting layer is made. Experiment shows that the material has excellent light emitting property.
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Description

technical field

[0001] The invention relates to an intramolecular charge transfer type red luminescent material with A-π-D-π-A symmetrical structure.

[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] Organic electroluminescent devices are a new type of display technology that is gradually becoming mature in the field of optoelectronic devices and has great practical prospects. Since Kodak Corporation (Tang, C.W.; Vanslyke, S.A. Appl. Phys. Lett. 1987, 51, 913.) introduced high-efficiency organic electroluminescent devices 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 po...

Examples

Embodiment 1

[0045] 3,5-bis(2'-dicyanomethenyl-4',4'-dimethyl-cyclohexenyl)methenyl-9-propyl-carbazole (compound 1)

[0046]

[0047] In a 100ml three-necked flask, mix 3,6-dialdehyde-9-propyl-carbazole (2mmol) and 2-dicyanomethenyl-4,4,6-trimethyl-cyclohexene (8mmol ) was placed in about 20ml of acetonitrile, 3ml of piperidine was added as a catalyst, and heated to reflux at 80°C for 10 hours under a nitrogen atmosphere; after the reaction stopped, cooled to room temperature, extracted with water / dichloromethane (60ml×2); combined organic phase, dried over anhydrous magnesium sulfate. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent-dichloromethane / petroleum ether 2:1 v / v) to obtain a dark red solid with metallic luster (yield 82%).

[0048] Mass spectrum (MALDI-TOF-MS): m / z calculated value 601, measured value 601.6 (M + );

[0049] H NMR spectrum ( 1 H-NMR) (400MHz, CDCl 3 , ppm): δ=1.01(...

Embodiment 2

[0053] 4,4'-bis(2'-dicyanomethenyl-4',4'-dimethyl-cyclohexenyl)methenyl-triphenylamine (compound 2)

[0054]

[0055] In a 100ml three-necked flask, put 4.4'-dialdehyde-triphenylamine (2mmol) and 2-dinitrile methyl-4,4,6-trimethyl-cyclohexene (8mmol) in about 20ml of acetonitrile , add 3ml of piperidine as a catalyst, and heat to reflux at 80°C for 10 hours under a nitrogen atmosphere; after the reaction stops, cool to room temperature and extract with water / dichloromethane (60ml×2); dry. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent-dichloromethane / petroleum ether 2:1 v / v) to obtain a dark red solid with metallic luster (yield 72%).

[0056] Mass spectrometry (TOF-MS-EI + )m / z: calculated value 637; measured value 637;

[0057] H NMR spectrum ( 1 H-NMR) (300MHz, CDCl 3 , ppm): δ=1.08(s, 12H), 2.46(s, 4H), 2.60(s, 4H), 6.82(s, 2H), 6.92-6.99(m, 4H), 7.07-7.09(t, 4H ), 7.17(t...

Embodiment 3

[0061] 3,5-bis(2'-dicyanomethenyl-4',4'-dimethyl-cyclohexenyl)methenyl-9-propyl-phenothiazine (compound 3)

[0062]

[0063] In a 100ml three-necked flask, 3,6-dialdehyde-9-propyl-phenothiazine (2mmol) and 2-dicarbonitrile-4,4,6-trimethyl-cyclohexene ( 8mmol) was placed in about 20ml of acetonitrile, 3ml of piperidine was added as a catalyst, under nitrogen atmosphere, heated to reflux at 80°C for 10 hours; after the reaction was stopped, cooled to room temperature, extracted with water / dichloromethane (60ml×2); combined The organic phase was dried over anhydrous magnesium sulfate. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent-dichloromethane / petroleum ether 2:1 v / v) to obtain a purple-red solid with metallic luster (yield 78%).

[0064] Mass spectrum (MALDI-TOF-MS): m / z calculated 633; ​​measured 633.1.

[0065] H NMR spectrum ( 1 H-NMR) (300MHz, CDCl 3 , ppm): δ=1.03(t, 3H),...