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A compound based on oxidized thioxanthone, preparation method and application thereof

A technology for oxidizing thioxanthone and compounds, which is applied in the fields of chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve different problems and achieve the goals of avoiding aggregation, improving thermal stability, and good photoelectric properties Effect

Active Publication Date: 2019-02-26
VALIANT 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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  • A compound based on oxidized thioxanthone, preparation method and application thereof
  • A compound based on oxidized thioxanthone, preparation method and application thereof
  • A compound based on oxidized thioxanthone, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Compound 1

[0051]

[0052] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-10,10-dioxo-10H-thianthracene-9-one, 0.015mol compound M1, 0.03mol sodium tert-butoxide, 1× 10 -4 molPd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150mL toluene, heated and refluxed for 24 hours, sampled and spotted, cooled naturally, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 98.90% and a yield of 50.9%.

[0053] HPLC-MS, molecular formula C 34 h 23 NO 4 S, theoretical value: 541.13, test value: 541.43.

Embodiment 2

[0054] Example 2 Compound 8

[0055]

[0056] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 3-bromo-10,10-dioxo-10H-thianthracene-9-one, 0.015mol compound M2, 0.03mol sodium tert-butoxide, 1× 10 -4 molPd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150mL toluene, heated to reflux for 24 hours, sampled and spotted, cooled naturally, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.80% and a yield of 47%.

[0057] HPLC-MS, molecular formula C 40 h 28 N 2 o 3 S, theoretical value: 616.18, test value: 616.28.

Embodiment 3

[0058] Example 3 Compound 16

[0059]

[0060] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-10,10-dioxo-10H-thianthracene-9-one, 0.011mol compound M3, 0.03mol sodium tert-butoxide, 1× 10 -4 molPd 2 (dba) 3 , 1×10 -4 mol tri-tert-butylphosphine, 150mL toluene, heated to reflux for 24 hours, sampled and spotted, cooled naturally, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.10% and a yield of 56%.

[0061] HPLC-MS, molecular formula C 36 h 25 NO 3 S, theoretical value: 551.16, test value: 551.19.

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Abstract

The invention discloses a compound based on oxidized thioxanthone, a preparation method and an application thereof, and belongs to the technical field of organic photoelectric materials. It has the structure shown in formula I: the compound based on thioxanthone oxide of the present invention is not easy to crystallize between molecules, not easy to aggregate, and has good film-forming properties, and the rigid group in the molecule can improve the thermal stability of the material , while the compound of the present invention has a D-A structure, and the distribution of electrons and holes is more balanced. When used as a light-emitting layer material in an OLED device, the efficiency roll-off at high current densities of the device decreases, the drive voltage of the device decreases, and the current of the device Increased efficiency and longevity.

Description

technical field [0001] The invention relates to a compound based on oxidized thioxanthone, a preparation method and an application thereof, and belongs to the technical field of organic photoelectric materials. 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. [0003] 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,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/048C07D413/04C07D471/04C07D487/04C07D491/052C07D491/056C07D409/04C07D413/10C07D409/10C07D498/06C07D491/153C07D471/06C07D409/14C09K11/06H01L51/54
CPCC09K11/06C07D409/04C07D409/10C07D409/14C07D413/04C07D413/10C07D471/04C07D471/06C07D487/04C07D491/048C07D491/052C07D491/056C07D491/153C07D498/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088C09K2211/1092H10K85/6576H10K85/657H10K85/6572
Inventor 杨福山胡葆华付文岗孟凡民王子宁秦余虎
Owner VALIANT CO LTD
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