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Thiaxanthene dioxide type organic electroluminescence material and preparation method and application thereof

A technology of thiadioxide and luminescence, which is applied in the direction of luminescent materials, chemical instruments and methods, organic chemistry, etc., to achieve the effects of improving efficiency roll-off, reducing efficiency roll-off, and reducing device voltage

Inactive Publication Date: 2017-05-24
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Currently, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, it is different from actual products Compared with the application requirements, the luminous efficiency and service life of OLED devices need to be further improved

Method used

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  • Thiaxanthene dioxide type organic electroluminescence material and preparation method and application thereof
  • Thiaxanthene dioxide type organic electroluminescence material and preparation method and application thereof
  • Thiaxanthene dioxide type organic electroluminescence material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Compound A1

[0048]

[0049] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 9,9-diphenyl-3-bromo-10,10-thioxanthene dioxide, 0.011mol compound C1, 0.03mol sodium tert-butoxide, 1× 10-4mol Pd 2 (dba) 3 , 1×10-4mol 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 98.56% and a yield of 54%.

[0050] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 46 h 33 NSO 3 , theoretical value: 679.22, test value: 679.43.

Embodiment 2

[0051] Example 2 Compound A2

[0052]

[0053] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 9,9-diphenyl-3-bromo-10,10-thioxanthene dioxide, 0.011mol compound C2, 0.03mol sodium tert-butoxide, 1× 10-4mol Pd 2 (dba) 3 , 1×10-4mol 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 99.70% and a yield of 59%.

[0054] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 46 h 33 NO 3 S, theoretical value: 679.22, test value: 679.58.

Embodiment 3

[0055] Example 3 Compound A3

[0056]

[0057] In a 250ml three-neck flask, under a nitrogen atmosphere, add 0.01mol 9,9-diphenyl-3-bromo-10,10-thioxanthene dioxide, 0.011mol compound C3, 0.03mol sodium tert-butoxide, 1× 10-4mol Pd 2 (dba) 3 , 1×10-4mol tri-tert-butylphosphine, 150ml toluene, heated to reflux for 24 hours, sampled and spot plated, 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 46%.

[0058] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 46 h 33 NO 3 S, theoretical value: 679.22, test value: 679.36.

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Abstract

The invention discloses a thiaxanthene dioxide type organic electroluminescence material and a preparation method and application thereof. A structural formula of the organic electroluminescence material is shown in the description. In the novel thiaxanthene dioxide type organic electroluminescence material, thiaxanthene dioxide is used as a mother nucleus to connect aromatic heterocyclic groups, molecular symmetry is destroyed, accordingly molecular crystallinity is destroyed, an intermolecular aggregation effect is avoided, the material has good film-forming property, most of molecules are rigid groups, and thus the heat stability of the material is improved. In addition, the thiaxanthene dioxide type organic electroluminescence material has a D-A structure, is more balanced in electron and hole distribution, has appropriate energy levels HOMO and LUMO, can effectively improve the exciton utilization ratio and high fluorescent radiation efficiency, reduce efficiency rolling-off under high current density and reduce device voltage, and the problem of efficiency rolling-off under high current density is solved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a thioxanthene dioxide-based organic electroluminescent material and its preparation method and application. 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 OLE...

Claims

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Application Information

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IPC IPC(8): C07D409/04C07D409/10C07D409/14C07D413/04C07D413/14C07D471/04C07D471/06C07D487/04C07D491/048C07D491/056C07D491/153C07D498/06C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D409/04C07D409/10C07D409/14C07D413/04C07D413/14C07D471/04C07D471/06C07D487/04C07D491/048C07D491/056C07D491/153C07D498/06C07D519/00C09K2211/1092H10K85/6576H10K85/6572H10K85/657
Inventor 孙虎王子宁付文岗张善国姜鹏潘作梁
Owner VALIANT CO LTD
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