Compound containing triarylamine structure, and organic light-emitting device prepared from same

A compound, triarylamine technology, applied in the field of organic electroluminescent materials, can solve different problems

Active Publication Date: 2019-12-17
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used ha...

Method used

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  • Compound containing triarylamine structure, and organic light-emitting device prepared from same
  • Compound containing triarylamine structure, and organic light-emitting device prepared from same
  • Compound containing triarylamine structure, and organic light-emitting device prepared from same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1: the synthesis of intermediate B1:

[0065]

[0066] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1-1, 0.012mol raw material 2-1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , obtain target product intermediate B1; HPLC purity 99.37%, yield 73.4%; Elemental analysis structure (molecular formula C 24 h 19 N): theoretical value C, 89.68; H, 5.96; N, 4.36; tested value: C, 89.65; H, 5.99; N, 4.37. ESI-MS (m / z) (M+): The theoretical value is 321.42, and the measured value is 321.58.

Embodiment 2

[0067] Embodiment 2: the synthesis of intermediate D1:

[0068]

[0069] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate B7, 0.012mol of raw material 3-1, 150ml of toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , to obtain the target product intermediate X1;

[0070] Under a nitrogen atmosphere, weigh 0.02mol of intermediate X1, 0.012mol of bis(pinacolate) diboron, 0.0002mol of Pd(dppf)Cl 2 1. Dissolve 0.05mol potassium acetate in toluene, react at 100-120°C for 12-24 hours, take a sample point plate, react completely, cool naturally, filter, and spin evaporate the filtrate to obtain a crude product, pass throug...

Embodiment 3

[0071] Embodiment 3: the synthesis of intermediate A1:

[0072]

[0073] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of raw material 4-1, 0.012mol of raw material 5-1, 150ml of toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , obtain target product intermediate A1; HPLC purity 98.96%, yield 70.5%; Elemental analysis structure (molecular formula C 23 h 13 BrN 2 O): theoretical C, 66.84; H, 3.17; Br, 19.33; N, 6.78; O, 3.87; found: C, 66.86; H, 3.19; Br, 19.31; ESI-MS (m / z) (M+): The theoretical value is 413.27, and the measured value is 413.39.

[0074] The synthetic raw materials of Intermediate A, Intermediate B and Inte...

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Abstract

The invention discloses a compound containing a triarylamine structure, and an organic light-emitting device prepared from the same. The pi conjugation effect in the compound enables the compound to have a very strong hole transport capability, and the high hole transport rate can reduce the initial voltage of the device and improve the efficiency of the organic light-emitting device; the asymmetric triarylamine structure can reduce the crystallinity of molecules, reduce the planarity of the molecules and prevent the molecules from moving on a plane, so that the thermal stability of the molecules is improved; the structure of the compound makes distribution of electrons and holes in a light-emitting layer balanced, and improves the hole injection and transport performances under a proper HOMO energy level; the structure also has an electron blocking layer under a proper LUMO energy level, so the recombination efficiency of excitons in the light-emitting layer is improved; and when thecompound is used as a hole transport layer or an electron blocking layer material of the OLED luminescent device, the triarylamine is matched with the branched chain in the structure, so the exciton utilization rate and the radiation efficiency can be effectively improved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to an organic compound containing a triarylamine structure and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED l...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00H01L51/54
CPCC07D471/04C07D519/00H10K85/622H10K85/615H10K85/624H10K85/636H10K85/633H10K85/6574H10K85/6576H10K85/6572
Inventor 李崇王芳张兆超徐浩杰
Owner JIANGSU SUNERA TECH CO LTD
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