Compound containing 9,9-spiral thioxanthene as well as preparation and application

A compound, thioxanthene technology, applied in the field of electroluminescent materials, achieves the effects of good reproducibility, improved device performance, and determined molecular weight

Inactive Publication Date: 2018-12-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Up to now, most of the evaporation molecules used in organic optoelectronic devices have skeletons of sulfoxyfluorene, phosphorus oxide, ...

Method used

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  • Compound containing 9,9-spiral thioxanthene as well as preparation and application
  • Compound containing 9,9-spiral thioxanthene as well as preparation and application
  • Compound containing 9,9-spiral thioxanthene as well as preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Dissolve 2-bromophenylphenylsulfide (11mmol, 2.93g) in 60ml of anhydrous THF, cool to -78°C, add n-BuLi (14.36mmol) dropwise, keep warm for 1 hour, and 9, 10-Anthraquinone (10mmol, 2.08g) was dissolved in 100ml THF and added dropwise to the reaction system overnight. It was extracted with dichloromethane, dried, and passed through a silica gel chromatography column Br to obtain a white solid. The obtained product was directly added to glacial acetic acid, heated to reflux, and 15 ml of concentrated hydrochloric acid was added to form a solid precipitate, which was filtered by suction to obtain the white solid product M1 (2.7 g, yield 50%). 1 H NMR (500MHz, CDCl 3 ( ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 6.52 (dd, J = 8.1, 1.1 Hz, 1H).

[0030] (2) Dissolve M1 (2.7g, 7.7mmol) in 50mL of glacial acetic acid and heat to reflux. Add 2 times molar equivalent of liquid bromine and react overnight. It was extracted with dichloromethane, washed with water, dried, and the solv...

Embodiment 2

[0035](1) Dissolve 2-bromophenylphenyl ether (11mmol, 2.82g) in 60ml of anhydrous THF, cool to -78°C, add n-BuLi (14.36mmol) dropwise, keep warm for 1 hour, and 2,7 -Dibromothioxanthone (10mmol, 3.70g) was dissolved in 100ml THF and added dropwise to the reaction system overnight. It was extracted with dichloromethane, dried, and passed through a silica gel chromatography column Br to obtain a white solid. The obtained product was directly added to glacial acetic acid, heated to reflux, and 15 ml of concentrated hydrochloric acid was added to form a solid precipitate, which was filtered by suction to obtain the white solid product M4 (2.7 g, yield 50%).

[0036] (2) Add M4 and 50mL glacial acetic acid in a 100mL three-necked flask, after stirring, add 10mL of 30% hydrogen peroxide, heat to reflux overnight, add ethanol after cooling, filter with suction, and remove the solvent under reduced pressure to obtain a white solid M5 with a yield of 97 %. 1 H NMR (500MHz, CDCl 3 )δ...

Embodiment 3

[0040] (1) Dissolve 2-bromotriphenylamine (11mmol, 3.42g) in 60ml of anhydrous THF, cool to -78°C, add n-BuLi (14.36mmol) dropwise, keep warm for 1 hour, and 2,7-di Bromothioxanthone (10mmol, 3.70g) was dissolved in 100ml THF and added dropwise to the reaction system overnight. It was extracted with dichloromethane, dried, and passed through a silica gel chromatography column Br to obtain a white solid. The obtained product was directly added to glacial acetic acid, heated to reflux, and 15 ml of concentrated hydrochloric acid was added to generate a solid precipitate, which was filtered by suction to obtain a white solid product M6 (2.7 g, yield 50%).

[0041] (2) Add M6 and 50mL glacial acetic acid in a 100mL three-necked flask, after stirring, add 10mL of 30% hydrogen peroxide, heat to reflux overnight, add ethanol after cooling, filter with suction, remove the solvent under reduced pressure to obtain a white solid M7, the yield is 97 %. 1 H NMR (500MHz, CDCl 3 )δ: 8.01 ...

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PUM

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Abstract

The invention belongs to the technical field of electroluminescent materials, and discloses a compound containing 9,9-spiral thioxanthene as well as a preparation and application. The compound containing 9,9-spiral thioxanthene has the structural formula represented by formula 1 or formula 2, wherein R1 and R2 are the same or different electron-donating vinylene group, ethynylene group, aromatic ring composed of carbon and hydrogen atoms, aromatic heterocyclic ring composed of carbon, nitrogen and hydrogen atoms, aromatic heterocyclic ring composed of carbon, nitrogen, oxide and hydrogen atoms, aromatic heterocyclic ring composed of carbon, sulfur and hydrogen atoms, and aromatic heterocyclic ring composed of carbon, silicon and hydrogen atoms, C1-C24 alkyl group, alkyl-substituted conjugated unit, alkoxy-substituted conjugated unit or conjugated unit in which an alkyl group and an alkoxy group are simultaneously substituted; X is a carbon atom, a nitrogen atom, a sulfur atom, a silicon atom, an oxygen atom, carbonyl or phosphorus atom group. The compound obtained by the invention has fluorescence, and is as the light-emitting layer of an organic electroluminescent diode that can significantly improve the external quantum efficiency of the device. (The formulas are shown in the description).

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a compound containing 9,9-spirothioxanthene and its preparation and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and developed an OLED device with a luminous brightness of 1000cd / m2 driven by a 10V DC voltage. 2 , so that OLED has achieved an epoch-making development. Over the past two decades, OLED devices employing novel emitters, especially organic-heavy metal complex phosphorescent emitters, have achieved considerable success. However, due to the difficulty in obtaining ba...

Claims

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Application Information

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IPC IPC(8): C07D495/10C07D409/14C07D413/14C07D417/14C07D335/04C09K11/06H01L51/50H01L51/54H01L51/56
CPCC09K11/06C07D335/04C07D409/14C07D413/14C07D417/14C07D495/10C09K2211/1092C09K2211/1088C09K2211/1037C09K2211/1033C09K2211/1029C09K2211/1007H10K85/6576H10K85/6572H10K85/657H10K50/11
Inventor 苏仕健刘坤坤彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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