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Metal-aluminum complexes and their applications in organic light-emitting devices

A technology of electroluminescent devices and complexes, which is applied in the direction of luminescent materials, organic chemistry, electric solid devices, etc., can solve the problems of lack of long-life transport materials and host materials, and achieve high electron mobility, good stability, and The effect of low bright voltage

Active Publication Date: 2016-07-06
TSINGHUA UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The problem to be solved by the present invention is the lack of long-life high electron mobility transport materials and host materials, thereby providing a class of metal aluminum complexes with high electron mobility, low HOMO energy level and higher triplet energy level; Applying such materials to the functional layers of organic electroluminescent devices, such as the main light-emitting layer, hole blocking layer or electron transport layer, realizes the multifunctionalization of a single material, thereby simplifying the device structure and achieving high efficiency and high efficiency of the device. low voltage

Method used

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  • Metal-aluminum complexes and their applications in organic light-emitting devices
  • Metal-aluminum complexes and their applications in organic light-emitting devices
  • Metal-aluminum complexes and their applications in organic light-emitting devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: Compound Q1-1

[0056] Reaction formula:

[0057]

[0058] 4.1g (20mmol) of aluminum isopropoxide and 3.42g (20mmol) of 4-(3-pyridine)phenol were dissolved in 80ml of toluene, heated to reflux and stirred for 3 hours. Then 2-methyl-8-hydroxyquinoline was dissolved in 20 ml of toluene, and the solution was added dropwise into the reaction bottle, and the solution was heated and stirred under reflux to react overnight. Filter and wash with toluene to obtain a white flocculent solid. The final product was purified by partition sublimation to obtain 4.3 g of a yellowish solid with a yield of 42%.

[0059] 1 H-NMR (CDCl 3 ,300MHz,δ[ppm]):2.73(s,6H),6.79~6.81(d,2H),6.89~6.92(m,2H),7.19~7.20(d,4H),7.37~7.39(m,4H ),7.60~7.62(d,2H),7.89~7.92(d,2H),8.65~8.67(d,2H).

[0060] ESI-MS[m / z]:514[M+H] + .Elemental analysis (C 31 h 24 AlN 3 o 3 ): Anal. Calcd.: C, 72.53; H, 4.71; N, 8.18. Found: C, 72.37; H, 4.36; N, 8.36.

Embodiment 2

[0061] Embodiment 2: Compound Q1-2

[0062] The synthesis of 3-(3-pyridine)phenol ligand can be obtained by referring to the literature (US20110039958A1). The synthesis of the complex refers to the synthesis method of Example 1, and the yield is 45%.

[0063] ESI-MS[m / z]:514[M+H] + .Elemental analysis (C 31 h 24 AlN 3 o 3 ): Anal. Calcd.: C, 72.53; H, 4.71; N, 8.18. Found: C, 72.44; H, 4.55; N, 8.00.

Embodiment 3

[0064] Embodiment three: compound Q1-3

[0065] The synthesis method is the same as in Example 1, except that 4-(3-pyridine)phenol is replaced by 2-(3-pyridine)phenol. The yield was 42%.

[0066] ESI-MS[m / z]:514[M+H] + .Elemental analysis (C 31 h 24 AlN 3 o 3 ): Anal. Calcd.: C, 72.53; H, 4.71; N, 8.18. Found: C, 72.37; H, 4.36; N, 8.36.

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Abstract

The invention provides a metal aluminium complex with the structural formula shown as a formula (I). In the formula (I), Q has a structural formula selected from a formula (Q1) or a formula (Q2); R1 is methyl, R2-R6 are independently selected from hydrogen, methyl and cyan; L has a structural formula shown as a formula (IV); R7-R11 are independently selected from hydrogen, phenyl, pyridyl, pyrimidinyl, C6-C30 substituted or unsubstituted aromatic rings and C6-C30 nitrogen-containing heteroaromatic rings. The invention also provides an organic luminescent device containing the metal aluminium complex. The metal aluminium complex is high in electro mobility, and is applicable to OLED devices as a luminescent-layer main material, a cavity barrier-layer material or an electron transfer layer, so that the multi-functionalization of a single material is realized, also the structure of the device is simplified, and high efficiency and low voltage of the device are realized.

Description

technical field [0001] The invention relates to a novel organic light-emitting material and its application in organic light-emitting devices. In particular, it relates to a class of metal-aluminum complexes and organic electroluminescence devices containing such materials. Background technique [0002] In 1987, Kodak's Deng Qingyun (C.W.Tang) and VanSlyke reported the use of tris (8-hydroxyquinoline) aluminum (Alq 3 ) as an organic functional layer, organic electroluminescent devices (OLEDs) were successfully prepared at low voltage for the first time, which aroused a research boom in the field of electroluminescence of organic materials. Due to their good thermal stability, the organometallic aluminum complexes are easy to deposit into void-free films under vacuum, the synthesis process is simple, and the cost is low. As electron transport layers or main light-emitting layers, they are widely developed and applied to OLEDs. middle. [0003] The hole mobility of commonly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/06C09K11/06H01L51/54
Inventor 乔娟林娜邱勇
Owner TSINGHUA UNIV
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