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Thioxanthone oxide derivative, preparation method and application thereof

A technology for oxidizing thioxanthone and thioxanthone, which is applied in chemical instruments and methods, silicon organic compounds, compounds of group 4/14 elements of the periodic table, etc., and can solve the problem of no host material for the light-emitting layer

Active Publication Date: 2014-08-27
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still very few phosphorescent devices in the true sense, especially blue phosphorescent devices. The fundamental reason is that there is no suitable host material for the light-emitting layer.

Method used

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  • Thioxanthone oxide derivative, preparation method and application thereof
  • Thioxanthone oxide derivative, preparation method and application thereof
  • Thioxanthone oxide derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0119] Synthesis of oxidized thioxanthone derivatives A-1:

[0120] The synthesis of 2-bromothioxanthone is referenced from Contribution From The Chemical Laboratory Of Iowa State College, vol.24, 1914~1916; William G P, Samuel S. The interaction of aromatic disulphides and sulfuric acid [J], JSC, 1910, 19II: 640-649.

[0121] The synthesis of 1,4-diphenylboronic acid pinacol ester refers to Chem.Eur.J.2004,10,2681–2688; Adv.Funct.Mater.2009,19,277-284; Adv.Funct.Mater.2007,17 ,2432–2438.

[0122] (1) Under the protection of an inert gas, mix 2-bromothioxanthone and 1,4-phenylenediboronic acid penalyl ester at a molar ratio of 2.5:1, and add 0.05 equivalent of tetrakis(triphenyl base phosphine) palladium and 5 equivalents of potassium carbonate, then the mixture was refluxed at 96°C for 8 hours in a mixed solvent of toluene, ethanol, and water with a volume ratio of 4:3:2, and the product was extracted, and the product was subjected to column chromatography (with The volume...

Embodiment 2

[0128] Synthesis of oxidized thioxanthone derivatives A-4:

[0129]

[0130] Same as Example 1, with 3-bromothioxanthone instead of 2-bromothioxanthone, and 1,3-benzenediboronic acid pinacol ester instead of 1,4-benzenediboronic acid pinacol ester, to obtain oxidized Thioxanthone derivative A-4, the yield is about 71%. EI-MS, m / z: 530.06 (100.0%), 531.07 (34.2%), 532.06 (8.4%).

Embodiment 3

[0132] Synthesis of oxidized thioxanthone derivatives A-7:

[0133]

[0134] Same as in Example 1, using 1,1'-biphenyl diboronic acid linalyl ester instead of 1,4-phenylene diboronic acid linalyl ester to obtain oxidized thioxanthone derivative A-7 with a yield of about 70 %. EI-MS, m / z: 606.10 (100.0%), 607.09 (43.1%), 608.11 (9.2%).

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Abstract

The invention discloses a thioxanthone oxide derivative, which has structural formulas as the following. In formula (1) and formula (2), R1, R2, R3, R4, R5, R6, R7 and R8 are respectively one of hydrogen atom, arylamino, aryl, and aromatic heterocyclic group; L can be absent or one of aryl, arylamino, heterocyclic aryl, and aromatic silane group. The invention also discloses a preparation method and application of the thioxanthone oxide derivative. By a simple method, a series of thioxanthone oxide derivatives with a high electron transmission rate can be synthesized.

Description

technical field [0001] The invention relates to oxidized thioxanthone derivatives and a preparation method thereof, as well as the application of the oxidized thioxanthone derivatives in organic electroluminescent devices. Background technique [0002] Since 1987, C.W.Tang et al. of Kodak Corporation of the United States first used the vacuum evaporation method to prepare small molecular thin film sandwich devices (C.W.Tang, S.A.Vanslyke, Applied Physics Letters, 1987, 51, 913), research on organic electroluminescent materials It has entered a new era. An organic electroluminescent device is mainly composed of a positive electrode, a negative electrode, and an active layer. Wherein, the active layer is a light-emitting layer, which is sandwiched between the positive and negative electrode layers to form a sandwich structure similar to a sandwich. In order to improve the injection and transport of carriers and improve the working efficiency of devices, carrier (hole and ele...

Claims

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Application Information

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IPC IPC(8): C07D335/16C07D409/14C07F7/08C09K11/06H01L51/54
CPCC09K11/06C07D335/16C07D409/14C07F7/0812C07F7/083C09K2211/1092C09K2211/1088C09K2211/1011C09K2211/1007C09K2211/1029H10K85/615H10K85/631H10K85/626H10K85/6576H10K85/6574H10K85/6572H10K85/40
Inventor 汪鹏飞王会刘卫敏王鹰
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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