2-substituted rubrene compound and its synthesis method and application

A synthesis method and compound technology, applied in the field of 2-substituted rubrene compounds and their synthesis, can solve the problems of inactive properties and low effects, and achieve the effect of broadening the scope of application

Inactive Publication Date: 2007-02-14
辽宁奥克华辉新材料有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is mostly reported that 2-substituted rubrene is used in the manufacture of organic electroluminescent devices, and although the above-mentioned compounds have achieved the purpose of making rubrene with substituents, their substituents can increase the degree of π electron conjugation, so that The role played by the red shift of the emission wavelength is not very large, and their nature is not active, and they need to be converted into active groups, such as bromomethyl, aldehyde groups, etc.

Method used

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  • 2-substituted rubrene compound and its synthesis method and application
  • 2-substituted rubrene compound and its synthesis method and application
  • 2-substituted rubrene compound and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of 2-formylrubrene (2-formyl-5,6,11,12-tetraphenyltetracene)

[0039] (1) Synthesis of intermediate 2-(1',3'-dioxolane)-6,11-diphenyl-5,12-tetracenequinone

[0040]

[0041] Add 0.964 g (2.00 mmol) of 2-formyl-6,11-diphenyl-5,12-tetraphenoquinone in a 100 ml two-necked flask, 60 ml of ethylene glycol, 28.9 mg of p-toluenesulfonic acid , heated to 160° C. for about 8 hours under the protection of nitrogen. During this period, HPLC (methanol: water = 9: 1) and TLC (n-hexane: ethyl acetate = 8: 3) were used to track the entire reaction process, and the reaction was stopped when the raw materials were basically consumed. The reaction solution was poured into an appropriate amount of saturated aqueous sodium bicarbonate solution and then filtered, and the filtered product was separated by column chromatography (silica gel 500-800 mesh, eluent was n-hexane:ethyl acetate=30:1), 2-(1',3'-dioxolane)-6,11-diphenyl-5,12-tetraphenoquinone was obtained as a...

Embodiment 2

[0045] Embodiment 2: the synthesis of 2-hydroxymethyl rubrene

[0046]

[0047] In a dark room, 56.1 mg (0.1 mmol) of 2-formylrubrene and 11.4 mg (0.3 mmol) of NaBH 4 Add in the mortar, mix thoroughly and grind, grind for about 30 min, add 10 ml of water to dissolve excess sodium borohydride, extract the product with 20 ml of chloroform, evaporate the solvent, and then process with the solvent method to obtain the target product (51.6 mg, the yield is 91.9%), and the melting point is greater than 300°C. IR (KBr, cm -1 ): 1020, 2928, 2956, 3070, 3620; mass spectrometry (MS - )562.0 (product molecular weight is 562.7); 1 H NMR (500MHz, CD 2 Cl 2 ): δ (ppm): 7.32-7.34 (m, 2H), 7.25 (s, 1H), 7.04-7.11 (m, 16H), 6.85-6.86 (m, 8H), 4.51-4.53 (m, 2H); Product liquid ultraviolet maximum absorption wavelength is 303.35, 462.16, 492.16, 526.35nm respectively (solvent is CH 2 Cl 2 ); the maximum emission wavelength of liquid fluorescence is 561.68nm (the solvent is CH 2 Cl 2...

Embodiment 3

[0048] Embodiment 3: the synthesis of N-(2'-methylene rubrenyl) aniline

[0049]

[0050] Add 56.1 mg (0.1 mmol) of 2-formylrubrene to a 20-milliliter two-port reactor wrapped in tin foil and vacuumize the dry and closed reaction system with an oil pump for 2 hours, during which four weeks are replaced with nitrogen. Once, add 9.2 microliters (0.1 mmol) of aniline with a micro-syringe, then add 5 milliliters of tetrahydrofuran that has just undergone anhydrous treatment with a syringe, and heat to reflux for 4 hours, during which HPLC (mobile phase is pure methanol) and TLC (n-hexane Alkane:ethyl acetate=10:1) followed the whole reaction process, and stopped the reaction when the relative peak of the target product reached the highest. The reaction solution was evaporated to dryness, and then treated by solvent method to obtain the target product (52.3 mg, yield 82.2%). The melting point is greater than 300°C. IR (KBr, cm-1): 1380, 1616; HRMS (EI): M + , found 636.2609.C...

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Abstract

The present invention is one kind of 2-substituted rubrene compound as shown and its synthesis process. The synthesis process includes the first synthesis of 2-formoxyl rubrene, and the subsequent oxidation, reduction and condensation with 2-formoxyl rubrene to obtain other 2-substituted rubrene compound. The synthesis process of 2-formoxyl rubrene under protection of inert gas includes the first reaction of 2-formoxyl -6, 11-diphenyl-5, 12-tetracene quinine material with glycol and catalyst at 120-160 deg.c; the subsequent reflux reaction with phenyl magnesium bromide and anhydrous tetrafuran; and final reflux reaction with iron powder and glacial acetic acid under heliophobic condition to obtain 2-formoxyl rubrene. The 2-substituted rubrene compound of the present invention as new type of red fluorescent material has high fluorescence quantum efficiency and may be used as the luminous material in electroluminescent device.

Description

technical field [0001] The invention relates to a 2-substituted rubrene compound and its synthesis method and application. Background technique [0002] Functional pigments can produce some special responses under various energy stimuli such as light, heat, and electricity. Using these properties, they can be used as information recording and display materials for electronic products; photosensitive materials for copiers and laser printers; laser energy conversion materials; solar energy Conversion and storage of materials, etc., are widely used in communications, automatic control, military industry, chemical industry, pharmaceuticals, pesticides and other fields. [0003] Polycyclic aromatic compound rubrene, whose chemical name is 5,6,11,12-tetraphenyltetracene, is a dye with high fluorescence efficiency, and its luminescence efficiency in solution is as high as 99% (Yildiz A, Kissinger PT, Reilley C N.J.Chem.Phys., 1968,49:1403.), as a functional fluorescent material, i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07D405/14C07D233/64C09K11/06
Inventor 胡知之张志强赵洪斌迟海军木村胜雷芃邹萍王东川石琨俞昌琪
Owner 辽宁奥克华辉新材料有限公司
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