Oxidized thioxanthone derivatives, 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

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

CN104003974BActive Publication Date: 2017-03-01TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Oxidized thioxanthone derivatives, preparation method and application thereof
  • Oxidized thioxanthone derivatives, preparation method and application thereof
  • Oxidized thioxanthone derivatives, 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 LaboratoryOf 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-phenylene diboronic acid pinacol ester at a molar ratio of 2.5:1, and add 0.05 equivalent of tetrakis(triphenyl Phosphine) palladium and 5 equivalents of potassium carbonate, then the mixture was refluxed at 96Β°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 extracted by column chromatography (with The volume ratio...

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 The yield of thioxanthone derivative A-4 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 an oxidized thioxanthone derivative. Its structural formula is as follows: In formula (1) and formula (2), R1, R2, R3, R4, R5, R6, R7, R8 are respectively selected from hydrogen Atom, aryl amino group, aryl group, aromatic heterocyclic group; L is one of none, aryl group, aryl amino group, heterocyclic aryl group, aromatic silane group. The invention discloses the preparation method and application of the oxidized thioxanthone derivatives, and adopts a simple method to synthesize a series of oxidized thioxanthone derivatives with high electron transport rate.

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 have prepared small molecular thin film sandwich devices for the first time by vacuum evaporation method (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, a carrier (...

Claims

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Application Information

Patent Timeline
01 Mar 2017
Publication
CN104003974B
IPC
C07D335/16; C07D409/14; C07F7/08; C09K11/06; H01L51/54
CPC
C09K11/06; C07D335/16; C07D409/14; C07F7/0812; C07F7/083; C09K2211/1092; C09K2211/1088; C09K2211/1011
Inventors
ζ±ͺ鹏飞; ηŽ‹δΌš