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Benzene-naphthalene diimide derivative, preparation method and its application

A naphthalene diimide and naphthalene imide technology, which is applied in the field of optoelectronic materials, can solve the problems of n-type carrier injection and transport materials with single types and narrow band gap

Inactive Publication Date: 2009-10-07
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The existing n-type carrier injection and transport materials suitable for organic light-emitting diodes are relatively single, mainly a class of compound materials represented by metal complexes with 8-hydroxyquinoline as a ligand, such compounds are Green luminescent material λmax=~518nm, emission peak half-maximum width>50nm, HOMO and LUMO energy level positions are located at 5.62eV and 2.85eV respectively, narrow band gap

Method used

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  • Benzene-naphthalene diimide derivative, preparation method and its application
  • Benzene-naphthalene diimide derivative, preparation method and its application
  • Benzene-naphthalene diimide derivative, preparation method and its application

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Embodiment 1

[0045] Embodiment 1: 1,3,5-three [(N'-butyl)-1 ', the synthesis of 8'-naphthalimide-4'-base] benzene

[0046] use as figure 1 Shown synthetic route prepares, specifically comprises the following steps:

[0047] (1), 1,3, the synthesis of 5-benzenetriboronic acid-tributanol ester

[0048] After passing nitrogen gas in a 250ml three-necked flask for 30min, add bisglutaryl boron (33mmol), appropriate amount of PdCl 2 With dppf, 90mmol potassium acetate, 1,3,5-bromobenzene (10mmol), and 120ml dimethyl sulfoxide (DMSO), heat and stir at 70°C until the raw material 1,3,5-bromobenzene disappears, and the reaction is terminated. After the reaction liquid was cooled to room temperature, it was filtered, and dimethyl sulfoxide (DMSO) was distilled from the filtrate under reduced pressure. The evaporated matter was washed with water with the filter cake, extracted with benzene, and the extract was dried with anhydrous magnesium sulfate. The solvent was distilled off by rotary distill...

Embodiment 2、1

[0053] Example 2, 1,3,5-tri{[N'-(2"-ethylhexyl)]-1',8'-naphthylamide-4'-yl}benzene

[0054] use as figure 1 Shown synthetic route prepares, specifically comprises the following steps:

[0055] (1), 1,3, the synthesis of 5-benzenetriboronic acid-tributanol ester:

[0056] After passing nitrogen gas in a 250ml three-necked flask for 30min, add bisglutaryl boron (33mmol), appropriate amount of PdCl 2With dppf, 90mmol potassium acetate, 1,3,5-bromobenzene (10mmol), and 120ml dimethyl sulfoxide (DMSO), heat and stir at 150°C until the raw material 1,3,5-bromobenzene disappears, and the reaction is terminated. After the reaction liquid was cooled to room temperature, it was filtered, and dimethyl sulfoxide (DMSO) was distilled from the filtrate under reduced pressure. The evaporated matter was washed with water with the filter cake, extracted with benzene, and the extract was dried with anhydrous magnesium sulfate. The solvent was distilled off by rotary distillation, and the si...

Embodiment 3、1

[0061] Example 3, 1,3,5-tri{[N'-(9", 9"-dibutylfluorene-2"-yl)]-1', 8'-naphthylamide-4'-yl}benzene

[0062] use as figure 1 The synthetic route shown specifically comprises the following steps:

[0063] (1), 1,3, the synthesis of 5-benzenetriboronic acid-tributanol ester:

[0064] After passing nitrogen gas in a 250ml three-necked flask for 30min, add bisglutaryl boron (33mmol), appropriate amount of PdCl 2 With dppf, 90mmol potassium acetate, 1,3,5-bromobenzene (10mmol), and 120ml dimethyl sulfoxide (DMSO), stir at 20°C until the raw material 1,3,5-bromobenzene disappears, and the reaction is terminated. After filtration, the filtrate was distilled off under reduced pressure to remove dimethyl sulfoxide (DMSO). The evaporated matter was washed with water with the filter cake, extracted with benzene, and the extract was dried with anhydrous magnesium sulfate. The solvent was distilled off by rotary distillation, and silica gel column chromatography was eluted with a mixed ...

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Abstract

The invention discloses a benzene-naphthalene diimide derivative, preparation method and its application. The benzene-naphthalene diimide derivative has the structure as shown in the right. The compound has good film-forming properties, higher mobility and fluorescent efficiency, stable narrow-band light-emitting properties, excellent electron injection and transport capacity. The preparation method uses amidation, Miyaura boric acid esterification, Suzuki coupling and other organic synthesis reactions, the preparation process is simple, and the product yield is high. The benzene-naphthalene diimide derivative can be applied in optoelectronic device fabrication.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, and relates to a benzene-naphthalene diimide derivative, a preparation method, and an application as an electroluminescence material in the manufacture of optoelectronic devices, especially organic light emitting diode devices and white light lighting devices. Background technique [0002] In 1987, C.W.Tang of Eastern Kodak Company successfully applied organic materials to organic EL devices with a sandwich structure in the literature Appl.Phys.Lett., 1987, 51, 913 and patent US4356429, and obtained high-efficiency organic light-emitting diode devices , so that the research work on organic semiconductor materials and devices has entered a practical era. For more than two decades, the application of organic semiconductor materials as active layers in plastic-based optoelectronic devices such as light-emitting diodes, field-effect transistors, and photovoltaic devices has attracted...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D401/14C07D409/14C07D417/14C07D413/14C09K11/06H01L51/50H01L51/54
CPCC09B57/08H10K85/621H10K85/655H10K85/615H10K85/6572H10K85/657H10K50/16
Inventor 曾鹏举刘亚伟牛憨笨牛芳芳连加荣胡强
Owner SHENZHEN UNIV
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