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N-substituted phenylbenzimidazole trivalent-iridium organometallic complex and its preparation method and use

A phenylbenzimidazole and organometallic technology, which is applied in the field of organic phosphorescent photoluminescent devices, can solve problems such as limiting the application of phosphorescent materials, and achieve the effects of simple preparation, good application prospects, and excellent color coordinates

Active Publication Date: 2012-09-12
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Existing Ir(ppy) 3 Phosphorescent materials such as FIrpic and FIrpic have achieved certain results in photoelectric properties such as brightness and efficiency. However, due to their strong emission point saturation and severe triplet-triplet quenching phenomenon, the maximum efficiency of the corresponding devices usually appears in At low current density (J2 ), and as the current density increases, the efficiency and brightness will decay rapidly, which limits the application of phosphorescent materials in passively driving organic electroluminescent display devices

Method used

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  • N-substituted phenylbenzimidazole trivalent-iridium organometallic complex and its preparation method and use
  • N-substituted phenylbenzimidazole trivalent-iridium organometallic complex and its preparation method and use
  • N-substituted phenylbenzimidazole trivalent-iridium organometallic complex and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In this example, the structural formula of the N-phenyl-2-phenylbenzimidazole trivalent iridium organometallic complex is:

[0030]

[0031] The preparation method of the above-mentioned N-phenyl-2-phenylbenzimidazole trivalent iridium organometallic complex comprises the steps:

[0032] Step 1: Synthesis of intermediate a1: N-phenyl-2-p-bromophenylbenzimidazole (BrPBI)

[0033] In a 250mL three-necked flask equipped with a stirring, thermometer, and gas-introducing device, argon gas was introduced for 10 minutes, and 10 parts of p-bromobenzoyl chloride and 10 parts of 2-aminodiphenylamine were sequentially added to react, 3 parts of triethylamine and 60 parts of tetrahydrofuran. Parts, reacted at room temperature for 24h, the reaction solution was poured into 100 parts of deionized water, extracted and separated with methylene chloride, dichloromethane was distilled off to obtain a crude product, and the crude product was recrystallized in a mixture solution of meth...

Embodiment 2

[0050] In this example, the structural formula of N-phenyl-2-(1'-naphthyl)benzimidazole trivalent iridium organometallic complex is:

[0051]

[0052] The preparation method of above-mentioned N-phenyl-2-(1'-naphthyl) benzimidazole trivalent iridium organometallic complex comprises the steps:

[0053] Step 1: Synthesis of Ligand NpPBI

[0054] In a three-necked flask equipped with a magnetic stirrer, 2 parts of the intermediate b1 synthesized in step 2 in Example 1: N-phenyl-2-(4-(4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl)phenyl)-1H-benzimidazole, 2 parts of 1-bromonaphthalene and 0.2 part of tetraphenylphosphopalladium were dissolved in 40 parts of toluene, under nitrogen protection The reaction was carried out at 105°C for 36 hours, the solvent was removed, and the ligand NpPBI was obtained through column separation and purification.

[0055] The above-mentioned ligand NpPBI is analyzed: mass spectrometry: (M + ): 396.2; elemental analysis: C 87.59, H 5.18, N 7.23,...

Embodiment 3

[0063] In this embodiment, the structural formula of N-phenyl-2-(9,9-dioctyl-fluorenyl) benzimidazole trivalent iridium organometallic complex is:

[0064]

[0065] The preparation method of the above-mentioned N-substituted phenylbenzimidazole trivalent iridium organometallic complex comprises the following steps:

[0066] Step 1: Synthesis of Ligand FPBI

[0067] In a three-necked flask equipped with a magnetic stirrer, 3 parts of the intermediate b1 synthesized in step 2 in Example 1: N-phenyl-2-(4-(4,4,5,5-tetramethyl-1 , 3,2-dioxaborolan-2-yl)phenyl)-1H-benzimidazole, 3 parts of 2-bromo-9,9-dioctylfluorene and 0.3 parts of tetrakistriphenylphosphopalladium were dissolved in 60 parts of toluene was reacted at 105° C. for 48 h under nitrogen protection, the solvent was removed, and the ligand FPBI was obtained through column separation and purification.

[0068] The above-mentioned ligand FPBI is analyzed: mass spectrometry: (M + ): 658.1; elemental analysis: C 87.47,...

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Abstract

The invention discloses an N-substituted phenylbenzimidazole trivalent-iridium organometallic complex and its preparation method and use in an organic electrophosphorescent doped light-emitting device. The N-substituted phenylbenzimidazole trivalent-iridium organometallic complex has a structural formula shown in the specification, wherein R1 and R2 represent any one of hydrogen, C1-C4 alkyl groups, C1-C4 halogenated alkyl groups, aryl groups, fused ring groups, anilino groups, carbazolyl groups and fluorenyl groups respectively. The N-substituted phenylbenzimidazole trivalent-iridium organometallic complex can be used in an organic electrophosphorescent doped light-emitting device having a layered doped structure, can be used as a guest material of a luminescent layer, and can be used for preparation of a yellow light-emitting material having a luminescent spectrum band of 560 to 610nm. Therefore, the N-substituted phenylbenzimidazole trivalent-iridium organometallic complex has good application prospects in monochrome and full color display and illumination white light-emitting devices.

Description

technical field [0001] The present invention relates to the technical field of organic phosphorescent electroluminescence (PhOLED) devices, and particularly designs an N-substituted phenylbenzimidazole trivalent iridium organometallic complex, its preparation method and its application in organic electrophosphorescent doped light emitting devices in the application. Background technique [0002] Organic electroluminescent materials and devices are currently a hot topic in international research. At present, many organic electroluminescent materials have been commercialized, and some organic display devices have also been widely used in mobile phones and displays. According to different luminescent principles, organic electroluminescent materials can be divided into two categories: fluorescent materials and phosphorescent materials. Compared with fluorescent materials, phosphorescent materials can make full use of all energy forms including singlet and triplet states, which...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 葛子义欧阳新华曾水明张兴业
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI