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Amido metal iridium complex electrophosphorescent luminescent material adopting phenylpyrazole main ligand and preparation thereof

A luminescent material and electrophosphorescence technology, applied in the field of amide-based metal iridium complexes and amide-based metal iridium organic complexes electrophosphorescence luminescent materials, can solve the problems of thermal decomposition, poor anti-crystallization performance, etc., and achieve easy synthesis, The effect of low cost, strong phosphorescent luminescence properties

Inactive Publication Date: 2013-07-17
JIANGNAN UNIV
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Problems solved by technology

[0005] The purpose of the present invention is to provide a class of amide group metal iridium complex electrophosphorescent luminescent materials with phenylpyrazole as the main ligand, which can be plated on transparent indium tin oxide (ITO) glass by evaporation. OLED can also be synthesized by simple ligand modification to polymerize the synthesized metal iridium complex to the polymer, and then spin-coat it into a PLED to solve the thermal decomposition of small molecule light-emitting materials that are prone to occur during the evaporation process. Disadvantages such as poor anti-crystallization performance

Method used

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  • Amido metal iridium complex electrophosphorescent luminescent material adopting phenylpyrazole main ligand and preparation thereof
  • Amido metal iridium complex electrophosphorescent luminescent material adopting phenylpyrazole main ligand and preparation thereof
  • Amido metal iridium complex electrophosphorescent luminescent material adopting phenylpyrazole main ligand and preparation thereof

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preparation example Construction

[0027] The preparation method of the metal iridium complex of the present invention: first use aniline or aniline derivatives and acid anhydrides or acid chlorides to heat and reflux in acetic acid to obtain amides (Hayl), and then use the obtained amides (Hayl) and 1-phenylpyrazole derivatives Dichloro bridge compound (C^N) of compound (C^N) 2 Ir(μ-Cl) 2 Ir(C^N) 2 Carry out reaction, obtain target product (C^N) 2 Ir(ayl). Concrete reaction steps are as follows:

[0028] (1) Synthesis of auxiliary ligand (Hayl)

[0029] The synthesis of acetaniline: the mixture of aniline (or 4-methylaniline, 2,6-dimethylaniline, 4-chloroaniline) and acetic anhydride (molar ratio of 1:2) was refluxed in acetic acid for 4 hours, and then The solution obtained by the reaction was poured into ice water, a large amount of solids were precipitated, stirred vigorously for 15 minutes and then suction filtered, and the obtained solids were recrystallized with ethanol to obtain relatively pure ace...

Embodiment 1

[0036] Embodiment 1: the auxiliary ligand is acetanilide, and the main ligand is the metal iridium complex (C^N) of 1-phenylpyrazole 2 The synthesis of Ir (ayl), i.e. two (1-phenylpyrazole)-acetanilide metal iridium complex, its structural formula is as follows:

[0037]

[0038] (1) Preparation of Acetanilide:

[0039] Add 9.3g of freshly distilled aniline and 20mL of acetic acid into a 100mL round bottom flask, then add 5.1g of acetic anhydride dropwise under stirring, heat to reflux at 120°C, and stop reflux after reflux for 4 hours. After cooling, the reaction solution was poured into ice water, a large amount of white solid was precipitated, filtered with suction, and the obtained white solid was dissolved in 100 mL of ethanol to crystallize. 10.9 g (81.0% yield) of colorless flaky crystals were obtained, m.p=125°C.

[0040] (2) Dichloro bridge compound (ppz) 2 Ir(μ-Cl) 2 Ir(ppz) 2 Synthesis:

[0041] Under nitrogen protection, add 0.068g (0.1929mmol) IrCl to the...

Embodiment 2

[0046] Embodiment 2: the auxiliary ligand is benzoyl naphthylamine, and the main ligand is the metal iridium complex (C^N) of 1-phenylpyrazole 2 The synthesis of Ir (ayl), i.e. two (1-phenylpyrazole)-benzoyl naphthylamine metal iridium complex, its structural formula is as follows:

[0047]

[0048] (1) preparation of benzoyl naphthylamine:

[0049] Add 5g of benzoic acid and 15mL of thionyl chloride into a 100mL round bottom flask, add 2 drops of N,N-dimethylformamide as a catalyst, and introduce the tail gas (HCl) generated by the reaction into a saturated sodium hydroxide solution, and reflux until hydrogen chloride-free generate. Distill under reduced pressure to remove unreacted thionyl chloride to obtain a colorless benzoyl chloride liquid.

[0050] Take another 100mL round-bottomed flask, add 5mL aniline and 30mL chloroform, then dissolve the benzoyl chloride obtained in the previous step in 20mL chloroform, and slowly add it dropwise to the vigorously stirred trie...

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Abstract

The invention relates to an amido metal iridium complex electrophosphorescent luminescent material adopting phenylpyrazole as main ligand and a preparation thereof, belonging to the technical field of electrofluorescence. The electrophosphorescent luminescent material is an amido metal iridium complex adopting the phenylpyrazole as main ligand, the molecular structure is (C^N)2Ir(ayl), wherein, (C^N) is bidentate ligand containing 1-phenylpyrazole structure, and ayl is bidentate ligand containing amide structure. The preparation method comprises the following steps : firstly, using aniline or aniline derivative and anhydride or acyl chloride to heat and backflow in acetic acid so as to obtain amide, then carrying out reaction by using the obtained amide and dichloro-bridge compound (C^N)2Ir(mu-Cl)2Ir(C^N)2 as the derivative of 1-phenylpyrazole (C^N) in ethylene glycol under the existence of sodium alcoholate, and obtaining the target product (C^N)2Ir(ayl) of electrophosphorescent luminescent material of bidentate ligand containing 1-phenylpyrazole structure. The synthetized metal iridium complex has stronger luminescent performance of phosphorescence and can be used as a functional material in an organic electrophosphorescent device.

Description

technical field [0001] The electrophosphorescent luminescent material of the amido metal iridium complex with phenylpyrazole as the main ligand and its preparation relates to the amido metal iridium complex with phenylpyrazole as the main ligand, and specifically relates to a class of metal iridium complexes that can be used in The invention relates to an electrophosphorescent luminescent material of an amido metal iridium organic complex containing phenylpyrazole as a main ligand in the field of electroluminescence. It belongs to the technical field of electroluminescence. Background technique [0002] Organic electroluminescence (EL) refers to a luminescence phenomenon in which organic materials directly convert electrical energy into light energy under the action of an electric field. The research on organic electroluminescent devices (OEL), that is, organic light-emitting diodes (OLEDs), began in the 1950s. By 1987, Eastern Kodak Company Tang et al. invented a sandwich...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F15/00
Inventor 丁玉强徐宏周伟
Owner JIANGNAN UNIV
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