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Full-bridge linked triphenylamine compound and application thereof in electroluminescent device

An electroluminescent device, a technology of triphenylamine, applied in the field of organic electroluminescent materials, can solve the problems of high molecular reformation energy and reduced molecular conjugation, and achieve high thermal stability, enhanced conjugation ability, thermal Stability-enhancing effect

Active Publication Date: 2009-09-09
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

[0006] In theory, in 1999, Sakaki proposed the concept of "planar nitrogen", that is, when the central nitrogen atom and the surrounding aromatic groups have a certain degree of conjugation, the hole transport performance is better. Adjacent phenyl groups are in a twisted state, resulting in reduced conjugation of the molecule, and the nitrogen cations formed during transport are sp 2 Hybridization, such molecular reformation energy is higher

Method used

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  • Full-bridge linked triphenylamine compound and application thereof in electroluminescent device
  • Full-bridge linked triphenylamine compound and application thereof in electroluminescent device
  • Full-bridge linked triphenylamine compound and application thereof in electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of 4,8,12-tris(xylylmethylene) bridged triphenylamine (abbreviated as HTM1)

[0020]

[0021] 3.87g p-bromotoluene (22.6mmol) was dissolved in 30ml absolute ether in a Schlenk tube. 9.3ml of n-BuLi (2.45M, 22.8mmol) was dropped into the Schlenk tube at -10°C, and reacted at low temperature for 1 hour after the drop was completed. 0.90g of 2,2',2"-triphenylamine tricarboxylate (2.15mmol) was dissolved in 20ml of absolute anhydrous THF and dropped into a Schlenk tube, and reacted for 3h. After the reaction was completed, dilute NH 4 Cl solution for quenching. Ether extraction. The organic phase was separated, washed three times with water, anhydrous Na 2 SO 4 dry. The organic solvent was spin-dried, and the obtained crude product was dissolved in 30 ml of glacial acetic acid, and heated to reflux. Carefully add 3ml of concentrated HCl dropwise and react for 3h. After the reaction, the solution was poured into 200 ml of ice water. 20ml of chloroform ...

Embodiment 2

[0023] Preparation of 2,6,10-triphenyl-4,8,12-tris(xylylmethylene) bridged triphenylamine (abbreviated as HTM2)

[0024]

[0025] 1.00 g (1.22 mmol) of 4,8,12-tris(xylylmethylene) bridged triphenylamine was dissolved in 20 ml of chloroform in a 50 ml round bottom flask. 0.68 g NBS (3.82 mmol) was added. The reaction was stirred at room temperature for 12h. After the reaction, the organic phase was washed with water three times. Anhydrous Na 2 SO 4 dry. Use petroleum ether: dichloromethane = 3: 1 (volume ratio) for column separation. 1.22 g of white solid 2,6,10-tribromo-4,8,12-tris(xylylmethylene) bridged triphenylamine was obtained with a yield of 95%. 1 H NMR (300MHz, CDCl 3 , δ): 6.91(s, 6H), 6.86(d, J=8.1Hz, 12H), 6.55(d, J=8.1Hz, 12H), 2.30(s, 18H); 13 C NMR (75MHz, CDCl 3 , δ): 141.809, 136.132, 134.261, 130.772, 130.701, 130.001, 128.697, 116.098, 55.293, 21.124.Ahal.Calcd.for C 63 h 48 Br 3 N (%): C, 71.47; H, 4.57; N, 1.32.Found: C, 71.23; H, 4.40; N, 1...

Embodiment 3

[0028] Preparation of 2,6,10-tris(4-triphenylamino)-4,8,12-tris(xylylmethylene) bridged triphenylamine (abbreviated as HTM3)

[0029]

[0030] HTM3 can be prepared in a similar manner to Example 2. 1 H NMR (300MHz, CDCl 3 , δ): 7.18-7.15(m, 18H), 7.05-6.91(m, 30H), 6.78(d, J=7.2Hz, 12H), 6.65(d, J=7.2Hz, 12H), 2.21(s, 18H).Anal.Calcd.for C 117 h 90 N 4 (%): C, 90.54; H, 5.85; N, 3.61.Found: C, 91.01; H, 6.16; N, 3.36; MALDI-TOF-MS: m / z 1551.5 (M + ).

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Abstract

The invention discloses triphenylamine compound with a full-bridge rigid structure and the application of the triphenylamine compound serving as hole transport layer material in electroluminescent device. The general structure of the compound is right formula; wherein, R is hydrogen atoms, phenyl, 4-triphenylamine or 3-(N-p-tert-butyl phenyl) which are same with each other. The triphenylamine compound has high thermal stability, and a synthetic method thereof is simple to be carried out. The compound can be used for preparing the electroluminescent device by a spin coating process, has low cost and extensive use. The electroluminescent device manufactured by triphenylamine compound serving as cavity transport layer material has electroluminescent performances of high efficiency and high brightness and can be widely applied to the organic electroluminescent field.

Description

technical field [0001] The invention relates to a triphenylamine compound with a full-bridge rigid structure and its application as a hole transport material in an electroluminescent device, belonging to the field of organic electroluminescent materials. Background technique [0002] Since 1987, C.W.Tang et al. of Kodak reported for the first time that Alq was prepared by vacuum evaporation method. 3 Since the double-layer device structure of light-emitting materials, organic electroluminescence has received great attention. [0003] In order to obtain devices with high luminous efficiency, devices with multilayer structures have been receiving extensive attention. The so-called multilayer device generally includes the following layers: hole injection layer, hole transport layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer. Among them, the hole transport layer generally contains an aromatic amine structure, and the lone pai...

Claims

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Application Information

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IPC IPC(8): C07D471/16H01L51/54H01L51/50C09K11/06
Inventor 杨楚罗蒋佐权曹越秦金贵
Owner 常熟紫金知识产权服务有限公司
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