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Iridium-containing coordination compound and organic light-emitting device thereof

A technology of organic light-emitting devices and iridium complexes, which is applied in the fields of light-emitting materials, organic chemistry, and electric solid-state devices, and can solve problems such as poor thermal stability, low luminous efficiency, and short life.

Inactive Publication Date: 2018-10-09
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Organometallic complexes have good luminescent properties, and many of them have been widely studied in the scientific research and industrial production of OLED and other electroluminescent technologies, but there are still deficiencies. Phosphorescent materials generally have poor thermal stability and low luminous efficiency. However, the fundamental factor determining the performance of organic electroluminescent devices is the choice of materials. Therefore, it is urgent to design and develop an organometallic complex with higher luminous efficiency and low driving voltage.

Method used

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  • Iridium-containing coordination compound and organic light-emitting device thereof
  • Iridium-containing coordination compound and organic light-emitting device thereof
  • Iridium-containing coordination compound and organic light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1: the preparation of compound 1

[0064]

[0065] Preparation of Intermediate A1

[0066] To a 100ml round bottom flask, sequentially add compound a1 (10.00g, 50.24mmol), DMF-DMA (8.3g, 70.34mmol), toluene (36.6ml) to dissolve, heat at 110°C for 24h, after the reaction, distill under reduced pressure The organic solvent was removed, and column chromatography was performed with ethyl acetate and hexane to obtain compound b1 (11.80 g, 46.43 mmol).

[0067] In the 500ml round bottom flask, add compound b1 (11.80g, 46.43mmol), compound c1 (5.53g, 1.14mmol), Na 2 CO 3 (3.34g, 31.48mmol) mixed with 300ml of methanol and 60ml of water, slowly added dropwise acetic acid to adjust the pH to about 4, heated at 135°C for 24h, after the reaction, extracted the organic matter with ethyl acetate and water, and distilled under reduced pressure The organic solvent was removed, and column chromatography was performed with ethyl acetate and hexane.

[0068] Into a 500m...

Embodiment 2

[0075] Embodiment 2: the preparation of compound 2

[0076] The b1 in Example 1 was replaced by equimolar b2, and the other steps were the same as in Example 1 to obtain the target compound 2 (5.90 g, 30%).

[0077]

[0078]Mass Spectrum m / z: 983.35 (calculated: 983.34). Theoretical element content (%)C 55 h 46 IrN 6 : C, 67.19; H, 4.72; Ir, 19.55; N, 8.55 Measured element content (%): C, 67.19; H, 4.72; Ir, 19.56; N, 8.54. The above results confirmed that the obtained product was the target product.

Embodiment 3

[0079] Embodiment 3: the preparation of compound 12

[0080] The b1 in Example 1 was replaced by equimolar b12, and the other steps were the same as in Example 1 to obtain the target compound 12 (6.19 g, 29%).

[0081]

[0082] Mass Spectrum m / z: 1067.45 (calculated: 1067.44). Theoretical element content (%)C 61 h 58 IrN 6 : C, 68.64; H, 5.48; Ir, 18.01; N, 7.87 Measured element content (%): C, 68.65; H, 5.47; Ir, 18.01; N, 7.87. The above results confirmed that the obtained product was the target product.

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Abstract

The invention discloses an iridium-containing coordination compound and an organic light-emitting device thereof, and relates to the technical field of an organic photoelectric material. The iridium-containing coordination compound has a structure as shown in a formula (I); an electron-rich dinitrogen coordination structure in the iridium-containing coordination compound is favorable for stabilizing central trivalent metal cation and influences distribution of electron cloud on metal iridium, so that great influence on the photoelectric property of the whole coordination compound molecule is generated; furthermore, a four-membered ring consisting of a ligand and metal of the dinitrogen coordination structure has higher rigidity, so that unnecessary vibration energy loss is reduced and high-efficiency light-emitting property is achieved. The coordination compound has higher heat stability and chemical property by adjusting a substitutional group. The iridium-containing coordination compound is prepared into the organic light-emitting device, in particular serves as a doping material, the device shows up the advantages of low driving voltage and high light-emitting efficiency and isbetter than the existing common OLED device.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an iridium-containing complex and an organic light-emitting device thereof. Background technique [0002] As a key material in OLED devices, organic light-emitting materials can be roughly divided into three categories according to the principle of light emission: traditional fluorescent materials, phosphorescent materials and thermally activated delayed fluorescence (TADF) materials. Traditional fluorescent materials can only use 25% of singlet excitons to emit light, and the luminous efficiency is low; phosphorescent materials can use 25% of singlet excitons and 75% of triplet excitons to emit light, which can theoretically reach 100% Internal quantum efficiency; typical TADF materials require that the energy difference between the singlet state and the triplet state is less than 0.1 eV. Through thermal activation, the triplet state excitons pass through...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/00
Inventor 韩春雪蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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