A kind of preparation method of OLED material based on arylamine-substituted anthracene derivatives

Abstract

The invention belongs to the technical field of organic electroluminescent materials, discloses a method for preparing an anthracene derivative OLED (Organic Light-emitting Diode) material based on arylamine substitution, and specifically discloses a method for synthesizing 9,10-dis(naphthalene-2-yl)-N2,N2,N6,N6-tetraphenyl anthracene-2,6-diamine. The method disclosed by the invention comprises the following steps: performing lithium halogen exchange on 2-bromonaphthalene and n-butyllithium under anhydrous oxygen-free low-temperature conditions, and then reacting with 2,6-dibromoanthraquinone to produce dihydroxy dibromide ADN; reducing with sodium sulfite and hydroiodic acid to produce 2,6-dibromo-9,10-dis(naphthalene-2-yl)anthracene; and carrying out Ullmann reaction between the 2,6-dibromo-9,10-dis(naphthalene-2-yl)anthracene and diphenylamine, thereby obtaining the target product. The synthetic method disclosed by the invention has the characteristics of readily available raw materials, fewer reaction steps, higher product yield and the like; the product is an orange solid and is easily dissolved in tetrahydrofuran; and the derivative is good in stability and can serve as an intermediate of organic electroluminescent materials such as OLEDs.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, in particular to a method for synthesizing 9,10-di(naphthalene-2-yl)-N2, N2, N6, N6-tetraphenylanthracene-2,6-diamine . Background technique [0002] Organic electroluminescent devices (OLEDs) are the third generation of flat-panel displays after cathode ray tube flat-panel displays and liquid crystal displays. It is the mainstream display technology in the display field in the future. The luminous performance of OLED is mainly determined by the OLED material. Therefore, in the preparation process of OLED materials, high-purity OLED materials and their intermediates are required. Anthracene is a blue fluorescent material. However, due to the planar structure of anthracene molecules, it is easy to aggregate between anthracene molecules to produce crystallization. If a group is introduced at the 9,10-position of anthracene molecules to reduce the aggregation between an...

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Problems solved by technology

[0003] 9,10-bis[3,5-bis(phenyl)phenyl]anthracene was found to be a better blue organic electroluminescent material (Jiang X Y, Z hang Z L, Z hang B X, et al.Stable blue and white or ganiclight emitting diodes[J].Chin.J.Lumin.,2000,21(4):369-372.), but there are few reports about its synthesis; synthesis of 9,10-position substituted anthracene derivatives Method (Miyaur a N, Suzuki A.Palladium-Catalyzedcross-coupling reactions of organoboron compounds[J].Chem.Rev.,1995,95(7):2457-2483), generally divided into two steps: the first step consists of Halogen (such as aryl bromide) is exchanged with n-butyllithium (n-BuLi) under anhydrous and oxygen-free low temperature conditions, and then reacted with trimethyl borate to obtain aryl boronic acid; the second step is from aryl boronic acid with 9, 10-dibromoanthracene reacts under the action of tetrakis(triphenylphosphine) palladium catalyst to obtain 9,10-disubstituted anthracene derivatives; the first step of this method requires anhydrous and oxygen-free low temperature conditions, and the second step requires expensive palladium Catalyst, a small amount of palladium remains in the final product and is difficult to remove, and the entire reaction takes a long time

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