Triarylamine compound, and application thereof in organic light-emitting device

A compound, triarylamine technology, applied to compounds containing triarylamine structures, the application field of organic electroluminescent devices, can solve different problems and other problems

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

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Triarylamine compound, and application thereof in organic light-emitting device
  • Triarylamine compound, and application thereof in organic light-emitting device
  • Triarylamine compound, and application thereof in organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] Embodiment 1, the synthesis of intermediate G:

[0159]

[0160] (1) Under nitrogen atmosphere, weigh raw material I, raw material J, Pd (PPh 3 ) 4 , toluene and ethanol were stirred and mixed, dissolved sodium carbonate in water, then added aqueous sodium carbonate solution into the reaction system, heated at 100-120°C, and refluxed for 10-24 hours. After the reaction, naturally cooled to room temperature, filtered, and the filtrate Layering, taking the organic phase, carrying out rotary evaporation under reduced pressure, and purifying through a neutral silica gel column to obtain intermediate K; the molar ratio of the raw material I to the raw material J is 1.2 to 2:1, and the molar ratio of sodium carbonate to the raw material I is 2.0~3.0:1, Pd(PPh 3 ) 4 The molar ratio with raw material I is 0.01~0.02:1, and the volume ratio of toluene, ethanol and water is 2:1:1;

[0161] (2) Weigh the intermediate K, dissolve it in o-dichlorobenzene, add triphenylphosphin...

Embodiment 2

[0184] Embodiment 2: the synthesis of compound 1:

[0185]

[0186] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material D1, 0.024mol intermediate G1, 1×10 -4 molPd(PPh 3 ) 4 , 100mL of toluene and 50mL of ethanol were stirred and mixed, 0.03mol of sodium carbonate was dissolved in 50mL of water, and then the aqueous solution of sodium carbonate was added to the reaction system, heated to 110°C, and refluxed for 24 hours. Sampling and spotting showed that there was no raw material D1 remaining. The reaction was complete; naturally cooled to room temperature, filtered, the filtrate was separated, the organic phase was taken, and subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and purified by a neutral silica gel column to obtain the target product with a HPLC purity of 98.8% and a yield of 57.7%;

[0187] Elemental analysis structure (molecular formula C 46 h 30 N 2 O): Theoretical C, 88.15; H, 4.82; N, 4.47; O, 2.55; Tested:...

Embodiment 3

[0188] Embodiment 3: the synthesis of compound 4:

[0189]

[0190] The preparation method of compound 4 is the same as that of Example 2, except that intermediate G1 is replaced by intermediate G2.

[0191] Elemental analysis structure (molecular formula C 52 h 34 N 2 O): theoretical value C, 88.86; H, 4.88; N, 3.99; O, 2.28; tested value: C, 88.89; H, 4.87; N, 3.97; ESI-MS(m / z)(M + ): The theoretical value is 702.27, and the measured value is 702.46.

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Abstract

The invention discloses a triarylamine compound, and an application thereof in an organic light-emitting device. The compound contains a triarylamine structure, has a strong electron enrichment property, and is connected with the long-chain branch structure of a carbazole derivative to make molecules not prone to crystallize and aggregate and achieve a good film-forming property; the compound hasan electron-rich property, the branch chain is an electron-donating group, and groups have different electron-donating capabilities, so the material has different HOMO energy levels, and can be used as different functional layer materials; and additionally, the compound has a high triplet state energy level, so the compound can effectively block energy loss, and is beneficial to energy transfer. When the compound is applied to the OLED as an organic light-emitting functional layer material, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved, and the service life of the device is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a 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 light-emitting device, and the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D405/12C07D209/94C07D487/04C07D491/147C07D471/04C07D307/91C07D491/153H01L51/50H01L51/54
CPCC07D491/048C07D405/12C07D209/94C07D487/04C07D491/147C07D471/04C07D307/91C07D491/153H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 李崇蔡啸张兆超赵四杰徐浩杰
Owner JIANGSU SUNERA TECH CO LTD
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