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Metal complex and OLED (Organic Light Emitting Device) thereof

A technology of organic light-emitting devices and metal complexes, which is applied in the fields of light-emitting materials, organic chemistry, and electric solid-state devices. It can solve problems such as low luminous efficiency, poor thermal stability, and low driving voltage, and achieve simple preparation methods and improved stability. , Increase the effect of the conjugated system

Inactive Publication Date: 2018-09-14
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 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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  • Metal complex and OLED (Organic Light Emitting Device) thereof
  • Metal complex and OLED (Organic Light Emitting Device) thereof
  • Metal complex and OLED (Organic Light Emitting Device) thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: the preparation of compound 1

[0073]

[0074] Preparation of Intermediate A-1

[0075] Compound a-1 (6.50g, 37.6mmol) was dissolved in tetrahydrofuran (140mL), and a hexane solvent and 2.5M n-butyl lithium (18mL, 45.1mmol) were added dropwise at -78°C, followed by stirring for 1 hour. After slowly adding trimethyl borate (13 mL, 56.4 mmol) dropwise, stirred for 2 h. Then 2M hydrochloric acid was added dropwise to neutralize, and the product was extracted with ethyl acetate and water. Recrystallization from dichloromethane and hexane gave compound b-1 (2.70 g, 47%). Weigh compound b-1 (19.20g, 125.5mmol), compound c-1 (35.62g, 125.5mmol), tetrakistriphenylphosphine palladium (11g, 10mmol) and potassium carbonate (84.2g, 609mmol), will weigh The reactant was dissolved in a solvent of toluene (1 L) / EtOH (200 mL) / distilled water (200 mL), and heated at 90° C. for 2 hours. Weigh compound d-1 (19.51g, 78mmol), heat at 200°C under the condition of Cu as ...

Embodiment 2

[0082] Embodiment 2: the preparation of compound 9

[0083] The b-1 in Example 1 was replaced by equimolar b-9, and the other steps were the same as in Example 1 to obtain the target compound 9 (5.13 g, 29%).

[0084]

[0085] Mass Spectrum m / z: 885.29 (calculated: 885.28). Theoretical element content (%)C 47 h 40 IrN 4 o 2 : C, 63.78; H, 4.56; Ir, 21.72; N, 6.33; O, 3.62 The measured element content (%): C, 63.79; H, 4.55; The above results confirmed that the obtained product was the target product.

Embodiment 3

[0086] Embodiment 3: the preparation of compound 105

[0087]

[0088] Preparation of Intermediate A-105

[0089] Compound a-105 (7.60g, 37.6mmol) was dissolved in tetrahydrofuran (140mL), and a hexane solvent and 2.5M n-butyllithium (18mL, 45.1mmol) were added dropwise at -78°C, followed by stirring for 1 hour. After slowly adding trimethyl borate (13 mL, 56.4 mmol) dropwise, stirred for 2 h. Then 2M hydrochloric acid was added dropwise to neutralize, and the product was extracted with ethyl acetate and water. Recrystallization from dichloromethane and hexane gave compound b-105 (2.95 g, 47%). Weigh compound b-105 (41.90g, 251mmol), compound c-105 (39.66g, 251mmol), tetrakis triphenylphosphine palladium (11g, 10mmol) and potassium carbonate (84.2g, 609mmol), the reaction The product was dissolved in a solvent of toluene (1 L) / EtOH (200 mL) / distilled water (200 mL), and heated at 90° C. for 2 hours. Weigh compound d-105 (15.62g, 78mmol), add triethyl phosphite (200mL) a...

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Abstract

The invention discloses a metal complex and an OLED (Organic Light Emitting Device) thereof, and relates to the technical field of organic photoelectric materials. The metal complex has a structure asshown in a formula (I), wherein an electron-rich dinitrogen coordination structure in the structure of the metal complex is beneficial for stabilizing central trivalent metal cations, and meanwhile,electron cloud distribution on metal iridium can also be affected, so that great influence to the photoelectric properties of a whole complex molecule can be generated; a quaternary ring formed by a ligand of the dinitrogen coordination structure and metal has stronger rigidity and is beneficial for reducing unnecessary vibration energy loss and realizing high-efficiency luminescence property. Byregulating substituent groups, the metal complex has better thermal stability and chemical property; by preparing the metal complex into a device and particularly using the metal complex as a doping material, the device has the advantages of low driving voltage and high luminous efficiency and is superior to a commonly used OLED.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a metal 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% singlet excitons and 75% triplet excitons to radiate and emit light, which can theoretically achieve 100% internal quantum efficiency. In 1998, M.A.Baldo et al. doped transition metal platinum in the light emitting layer The organic chelating molecule PtOEt prepared a saturated red phosphorescent OLED device with an external quantum...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 韩春雪蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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