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Bridged triphenyl amine compound, and use in electrophosphorescent device

A technology of electrophosphorescence and compounds, which is applied in the field of organic electroluminescent materials, can solve the problems of insufficient luminous efficiency, insufficient rigidity, and insufficient thermal stability of electrophosphorescent devices, and achieve high-efficiency electroluminescent performance and stability Improvement, high thermal stability effect

Active Publication Date: 2009-08-05
常熟紫金知识产权服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the triphenylamine compound currently reported as the host material is not sufficiently rigid, resulting in insufficient thermal stability. In addition, the luminous efficiency of the electrophosphorescent device prepared using it as the host material is not high enough.

Method used

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  • Bridged triphenyl amine compound, and use in electrophosphorescent device
  • Bridged triphenyl amine compound, and use in electrophosphorescent device
  • Bridged triphenyl amine compound, and use in electrophosphorescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of 3,11-bis(triphenylsilyl)-7-tert-butyl-5,5,9,9-tetraphenyl-13b-azinaphthoanthracene (abbreviated as Host1)

[0025]

[0026] 1.4 g of bromobenzene (8.8 mmol) were dissolved in 10 ml of THF in a Schlenk bottle. 3.4ml of n-BuLi (2.6M, 8.8mmol) was dropped into a Schlenk bottle at -78°C, and reacted at -78°C for 1 hour after the drop was completed. 0.83 g of 2-(diphenylamino)-5-tert-butyl-1,3-isophthalic acid dimethyl ester was dissolved in 10 ml of THF and dropped into a Schlenk bottle for 3 hours of reaction. After the reaction was completed, it was quenched with distilled water. extracted with ether, the organic phase was separated, washed three times with water, anhydrous Na 2 SO 4 dry. The organic solvent was spin-dried to obtain a light green solid. The crude product was dissolved in 30ml of glacial acetic acid, heated to reflux at 110°C, and 3ml of concentrated HCl was carefully added dropwise to react for 3h. After the reaction, the solution ...

Embodiment 2

[0030] Preparation of 3,11-bis(triphenylsilyl)-7-tert-butyl-5,5,9,9-tetrakis(p-tolyl)-13b-azanaphthoanthracene (abbreviated as Host2)

[0031]

[0032] Using a method similar to Example 1, the difference is that p-methylbromobenzene is used as a starting material instead of bromobenzene to obtain 3,11-bis(triphenylsilyl)-7-tert-butyl-5, 5,9,9-Tetrakis(p-tolyl)-13b-azinaphthoanthracene, the yield is 47%. 1 H NMR (300MHz, CDCl 3 , δ): 7.42-7.34(m, 18H), 7.30-7.25(m, 16H), 7.01-6.90(m, 12H), 6.80-6.73(m, 8H), 2.31(s, 6H), 2.25(s , 6H), 1.08(s, 9H); 13 CNMR (300MHz, CDCl 3 ,δ):144.04,143.56,143.30,140.15,139.12,136.43,135.65,135.54,134.79,134.39,131.39,129.44,129.13,128.61,128.15,127.89,126.38,125.06,116.96,99.83,56.83,34.55,31.60, 21.29, 21.12. Anal. Calcd. for C 88 h 75 NSi 2 (%): C, 87.88; H, 6.29; N, 1.16. Found: C, 88.36; H, 5.96; N, 0.85. MS (MALDI-TOF) m / z 1201.9 [M + ].

Embodiment 3

[0034] Preparation of 3,11-bis(9-phenylfluorenyl)-7-tert-butyl-5,5,9,9-tetraphenyl-13b-azinaphthoanthracene (abbreviated as Host3)

[0035]

[0036] 0.31 g of 7-tert-butyl-5,5,9,9-tetraphenyl bridged triphenylamine (0.5 mmol), and 0.258 g of 9-phenyl-9-fluorenol (1 mmol) were put into 50 ml round bottom flasks respectively. 10 ml of dichloromethane were added. Carefully add 0.15ml BF 3 ·Et 2 O (1.1 mmol, 7.73M). Reaction at room temperature for 2h. After the reaction was completed, methanol was first added, followed by water to quench, and the organic phase was separated. Using petroleum ether:dichloromethane=2:1 (volume ratio) for column separation, 0.47 g of white solid was obtained with a yield of 86%. Characterization analysis confirmed that the white solid was Host3. 1 H NMR (300MHz, CDCl 3 , δ): 7.67(d, J=7.2Hz, 4H), 7.27-7.25(m, 6H), 7.19-7.02(m, 24H), 6.99-6.81(m, 16H), 6.74-6.62(m, 4H ), 1.04(s, 9H); 13 C NMR (300MHz, CDCl 3 ,δ):151.66,151.46,146.86,146.2...

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Abstract

The invention discloses bridged triphenylamine compounds and an electrophosphorescent device taking the bridged triphenylamine compounds as a main body material. A general structural formula of the compounds is shown at the right, wherein Ar2s are triphenylsilyls or 9-phenylflourenyls which are the same as each other when Ar1s are phenyls; and the Ar2s are the triphenylsilyls or 9-p-tolyl flourenyls which are the same as each other when the Ar1s are p-tolyls. The electrophosphorescent device produced by taking the compounds as the main body material has high-efficiency and high-brightness electroluminescent property, and can be widely applied in the field of organic electroluminescence.

Description

technical field [0001] The invention relates to a class of bridging triphenylamine compounds and their application in electrophosphorescent devices, belonging to the field of organic electroluminescent materials. Background technique [0002] Since C.W.Tang et al. of Kodak Company reported for the first time in 1987 that a double-layer device structure using Alq3 as a light-emitting material was prepared by vacuum evaporation, organic electroluminescence has attracted great attention. [0003] Organic electroluminescence can be divided into fluorescence and phosphorescence electroluminescence. According to the spin quantum statistical theory, the formation probability ratio of singlet excitons and triplet excitons is 1:3, that is, singlet excitons only account for 25% of the "electron-hole pairs". Therefore, the fluorescence from the radiative transition of singlet excitons only accounts for 25% of the total input energy, while the electroluminescence of phosphorescent mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07D455/03C09K11/06H01L51/50H01L51/54
Inventor 杨楚罗蒋佐权樊聪秦金贵
Owner 常熟紫金知识产权服务有限公司
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