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A kind of dithioxanthone derivatives and its preparation method and application

A technology of thioxanthone and its derivatives, which is applied in the field of organic electroluminescence display, can solve the problems that it is not suitable for the preparation of high color rendering index white light OLED devices, and cannot realize light emission at different positions, so as to improve the electron and hole transport performance , high color rendering index, and the effect of widening the conjugate length

Active Publication Date: 2022-03-04
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

[0003] It has been reported before that thermally activated delayed fluorescent light-emitting materials based on thioxanthone derivatives show excellent luminous performance in OLED devices, but the light-emitting positions are in the yellow and orange light regions, and light emission at different positions cannot be achieved. Suitable for preparing white OLED devices with high color rendering index

Method used

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  • A kind of dithioxanthone derivatives and its preparation method and application
  • A kind of dithioxanthone derivatives and its preparation method and application
  • A kind of dithioxanthone derivatives and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0123] Synthesis of 2,9-dibromothiochromeno[2,3-b]thioxanthene-7,14-dione:

[0124]

[0125] Dissolve 150mg of compound 1 and 180mg of compound sodium hydride in 10ml of ultra-dry N,N-dimethylformamide (DMF), vacuumize and blow with nitrogen. 500 mg of compound 2 was dissolved in 10 ml of DMF, and added to the solution of compound 1, and the reaction mixture was heated to 130° C. for 5 h. 100ml of water was added to the reacted solution, the precipitate was filtered out, and 438mg of product 3 was obtained by column chromatography.

[0126] Mix 200mg of compound 3, 5g of potassium hydroxide, 10ml of water, and 10ml of ethanol in a flask, heat it to 100°C until the reaction solution becomes clear and then cool down to room temperature, add excess hydrochloric acid to precipitate the precipitate, filter the precipitate, and dry it in vacuum Oven drying yielded 210 mg of compound 4.

[0127]200mg of compound 4 was dissolved in 10ml of concentrated sulfuric acid, heated to 60...

Embodiment 2

[0129] Synthesis of 2,9-dibromothiochromeno[2,3-b]thioxanthene-7,14-dione oxidation product: Dissolve 200mg of compound a-1 in 20ml of dichloromethane in an ice-water bath, slowly add 300mg, The reaction solution was moved to room temperature for overnight reaction. The reaction solution was concentrated, and column chromatography obtained 106 mg of the compound represented by the product formula a-2. 1H NMR (400MHz, TFA) δ8.22 (s, 2H), 8.09 (d, J = 1.5Hz, 2H), 7.93 (dd, J = 7.5, 1.5Hz, 2H), 7.75 (d, J = 7.5Hz ,2H).EIMS m / z(%):calcd for C20H8Br2O6S2,567.81; Found:567.81.

[0130]

Embodiment 3

[0132] Synthesis of Triphenylamine-substituted Dithioxanthone Derivatives Comp-1

[0133] Weigh 200mg of 2,9-dibromothiochromeno[2,3-b]thioxanthene-7,14-dione and 650mg of 9-triphenylamine boronic acid into a 250mL two-necked bottle, add 50mg of tetrakistriphenyl Phosphine palladium, 15mL of 2M potassium carbonate aqueous solution and 40mL of toluene solvent, after reflux reaction under nitrogen protection for 5h, the solvent was removed under reduced pressure, extracted with dichloromethane and water, the organic phases were combined, the solvent was evaporated to dryness under reduced pressure, and column chromatography was obtained m-chloroperoxybenzoic acid to dithioxanthone derivatives Comp-1.

[0134]

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Abstract

The invention discloses a dithioxanthone derivative, a preparation method thereof and an application in an electroluminescent device. The general structural formula of the dithioxanthone derivatives is shown in formula I and formula II: wherein, X is selected from a sulfur atom or a sulfone group; R 1 , R 2 , R 3 , R 4 and R 5 Each independently selected from a hydrogen atom, an arylamino group of 6 to 30 carbon atoms, an aryl group of 6 to 30 carbon atoms, a substituted aryl group of 6 to 30 carbon atoms, a substituted aromatic group of 5 to 50 ring atoms heterocyclic group. In the present invention, oxidized and unoxidized dithioxanthone derivatives introduce a variety of electron-donating groups, realize effective donor-acceptor molecular design, and can effectively separate the highest occupied orbital energy level and the lowest empty orbital of molecules The energy level not only reduces the energy level difference between the singlet state and the triplet state, but also realizes the property of thermally activated delayed fluorescence, and realizes the emission of different colors. Applied to the light-emitting layer of an organic electroluminescent device, the device has excellent performance.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence display. More specifically, it relates to a dithioxanthone derivative and its synthesis preparation method, and the application of organic electroluminescent devices. Background technique [0002] As one of the indispensable and important components in Organic Light-Emitting Diode (OLED) devices, organic light-emitting materials directly affect the device performance of OLEDs. Although fluorescent light-emitting materials exhibit excellent stability, the internal quantum efficiencies (IQEs) of fluorescent OLED devices are limited to 25%, resulting in unsatisfactory device performance of such devices. OLED devices based on phosphorescent emitters can achieve 100% exciton utilization under electrical excitation. However, the introduction of expensive transition metals into phosphorescent materials increases the cost of device fabrication. In addition, phosphorescent OLED device...

Claims

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Application Information

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IPC IPC(8): C07D495/04C09K11/06H01L51/50H01L51/54
CPCC07D495/04C09K11/06C09K2211/1092C09K2211/1007C09K2211/1014C09K2211/1029H10K85/6576H10K85/6572H10K50/11Y02B20/00
Inventor 王鹰刘建君汪鹏飞魏晓芳李志毅王瑞芳胡晓晓高洪磊刘冠豪
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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