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Phosphorescent dye parent materials with tetrahedral structure, and application thereof in electroluminescent device

A phosphorescent dye, tetrahedral technology, applied in the field of organic electroluminescent materials, can solve the problem of lack of parent materials, etc., and achieve the effects of high carrier migration ability and high electroluminescence efficiency

Inactive Publication Date: 2012-11-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One of the important reasons is the lack of suitable parent materials, that is, materials with high triplet energy levels and bipolar carrier transport properties

Method used

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  • Phosphorescent dye parent materials with tetrahedral structure, and application thereof in electroluminescent device
  • Phosphorescent dye parent materials with tetrahedral structure, and application thereof in electroluminescent device
  • Phosphorescent dye parent materials with tetrahedral structure, and application thereof in electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0035] Synthesis of SiPy

[0036]

[0037] Combine 0.83g (2mmol) 4-bromophenyl-triphenyl silicon, 0.30g (2.4mmol) 4-pyridineboronic acid and 92mg (4mol%) [(PPh 3 ) 4 The Pd(0) catalyst was dissolved in a mixed solvent of 12mL toluene, 6mL methanol and 6mL sodium carbonate solution with a concentration of 2mol / L. The system was degassed for three times and then transferred to an oil bath and reacted at 85°C for 48 hours. The reaction solution was poured into water, extracted three times with dichloromethane, and the collected organic phase was dried with anhydrous magnesium sulfate. After filtration, use a rotary evaporator to concentrate the solution, use a mixed solvent of dichloromethane, petroleum ether and ethyl acetate (volume ratio 1:4:1) as the eluent, and purify by thin layer chromatography to obtain 0.68g of white solid , The yield is 82%. 1 H NMR(CDCl 3 , 500MHz, ppm): δ8.67-8.66 (2H, d, J = 4.27 Hz, Ar-H), 7.71-7.69 (2H, d, J = 7.94 Hz, Ar-H), 7.65-7.64 (2H, d, J = 8....

Synthetic example 2

[0039] Synthesis of CzSi

[0040]

[0041] 0.84g (5mmol) of carbazole, 2.49g (6mmol) of monomer 4-bromophenyl-triphenylsilica, 95mg (10mol%) of Cul catalyst, 114mg (20mol%) of trans 1,2- Diaminocyclohexane, 2.23g (210mol%) potassium phosphate, 12mL toluene solvent were placed in a 100mL round bottom flask, the system was degassed three times and then transferred to an oil bath, and reacted at 110°C for 48 hours. The reaction solution was poured into water, extracted three times with dichloromethane, and the collected organic phase was dried with anhydrous magnesium sulfate. After filtration, the solution was concentrated with a rotary evaporator, using a mixed solvent of dichloromethane and petroleum ether (volume ratio of 1:6) as the eluent, thin layer chromatography to obtain 1.23 g of white solid with a yield of 49%. 1 H NMR(CDCl 3 , 500MHz, ppm): δ8.16-8.14 (2H, d, J=7.94Hz, Ar-H), 7.82-7.81 (2H, d, J=8.24Hz, Ar-H), 7.67-7.65 (6H, m, Ar-H), 7.62-7.60 (2H, d, J=8.24 Hz, Ar-H)...

Synthetic example 3

[0043] Synthesis of DCzSi

[0044]

[0045] The synthesis process is the same as CzSi. White solid, the yield is 62%. 1 H NMR(CDCl 3 , 500MHz, ppm): δ 8.29-8.28 (1H, d, J=1.83 Hz, Ar-H), 8.19-8.18 (2H, d, J=7.94 Hz, Ar-H), 8.12-8.10 (1H, d, J = 7.63 Hz, Ar-H), 7.88-7.86 (2H, d, J = 8.24 Hz, Ar-H), 7.69-7.66 (9H, m, Ar-H), 7.57-7.54 (2H, m , Ar-H), 7.51-7.43 (10H, m, Ar-H), 7.41-7.39 (4H, m, Ar-H), 7.34-7.28 (3H, m, Ar-H), 13 C NMR(CDCl 3 , 125MHz, ppm): 142.29, 141.74, 140.16, 139.11, 138.47, 136.86, 134.64, 134.21, 130.46, 130.30, 128.49, 127.10, 126.60, 126.28, 125.93, 124.96, 123.54, 121.00, 120.69, 120.02, 119.91, 111.44, 110.72, 110.23. Theoretical value of element analysis: C 48 H 34 N 2 Si: C, 86.45%; H, 5.14%; N, 4.20%. Actual value: C, 86.71%; H, 5.08%; N, 4.16%. Mass spectrum: m / z 667.3 (100%).

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Abstract

The invention belongs to the technical field of organic electroluminescence material, in particular to a series of phosphorescent dye parent materials with a tetrahedral structure, and the application of the materials in an electroluminescent device. The phosphorescent dye parent materials can be used for a panel display device, a light-emitting diode (LED) and an electronic imaging device. The phosphorescent dye parent material has excellent electronic and hole transmission properties, can be independently used as a luminous layer and a current carrier transmission layer, and can be used as matrix and doped with other fluorescent or phosphorescent dyes. The compound has stronger fluorescent property in a state of solution or solid, can be used for forming an even film, and has better optical stability and thermal stability. R1, R2, R3 and R4 are respectively connected with phenyl group by a single bond, and are respectively selected from one of hydrogen, alkyl group, alkoxy, nitryl, hydroxyl, cyano-group, benzene cyano-group, amino, sulfydryl, halogen, diphenyl phosphoryl, furan, thiophene, pyrrole, pyridina, diazine, triazine, pyran, quinoline, benzpyrole, carbazole, aniline or phenothiazine, and X is C or Si.

Description

Technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and specifically relates to a series of phosphorescent dye matrix materials with a tetrahedral structure and their applications in electroluminescent devices. Such materials can be used in flat panel display devices, light-emitting diodes, and electronic imaging equipment. Background technique [0002] Since 1987, Kodak Company Tang et al. of the United States first reported on double-layer light-emitting devices prepared by vacuum evaporation, organic light-emitting devices have received extensive attention. In 1997, Professor Ma Yuguang first reported a light-emitting device containing osmium-containing heavy metal complex phosphorescent material, which opened a new chapter in light-emitting devices. Compared with fluorescent materials, electroluminescence of phosphorescent materials can utilize all excitons to achieve an internal quantum efficiency of nearly 100%, whic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C07F9/572C07F9/53C09K11/06H01L51/50H01L51/54
Inventor 马於光路萍胡德华刘贺吕营
Owner JILIN UNIV
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