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Bivalent platinum coordination compound and application thereof as well as organic photoelectric device

A technology of organic photoelectric devices and platinum complexes, which is applied in organic chemistry, circuits, and compounds containing elements of Group 8/9/10/18 of the periodic table, etc., can solve problems such as difficulties and limited types of organic photoelectric devices, and achieve Narrow luminescent range, easy sublimation and purification, and easy preparation

Active Publication Date: 2019-05-14
NANJING UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the types of organic optoelectronic devices that can reach the blue light emitting range are relatively limited. Correspondingly, it is more difficult to control the appropriate blue light spectrum so that blue light emitting devices can exhibit excellent performance during the light emitting process.

Method used

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  • Bivalent platinum coordination compound and application thereof as well as organic photoelectric device
  • Bivalent platinum coordination compound and application thereof as well as organic photoelectric device
  • Bivalent platinum coordination compound and application thereof as well as organic photoelectric device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Complex 16 and its preparation

[0083] Synthesis of 2-bromo-9-(2-pyridyl)carbazole:

[0084]

[0085] To a sealed 48 mL tube with a magnetic rotor, 2-bromocarbazole 0001 (3.69 g, 15 mmol), 2-bromopyridine 0002 (1.57 mL, 16.5 mmol), cuprous iodide (0.3 mmL, 0.02 equiv), and 1-Methylimidazole (0.3 mmol, 1.2 equiv), t-BuOLi (18 mmol, 1.2 equiv) and toluene (50 mL), the resulting mixture was bubbled with nitrogen for 10 minutes and then heated to 120° C. and stirred for 8 hours. Cool to room temperature, add water to quench the reaction, extract with ethyl acetate, combine the organic phases, wash with an appropriate amount of saturated aqueous sodium chloride solution and dry over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude product was separated and purified by silica gel column chromatography, the eluent was petroleum ether:ethyl acetate=25:1, and a white solid was obtained with a yield of 93%.

[0086] ...

Embodiment 2

[0103] Complex 18 and its preparation

[0104] Synthesis of 2-(3-methyl-5-amino-phenol)-9-(2-pyridyl)carbazole 0007:

[0105]

[0106] Add 2-bromo-9-(2-pyridyl)carbazole 0003 (1 equiv), 3-methyl-5-amino-phenol 0006 (1.2 equiv), cuprous iodide (10% ), L-proline (L-Pro, 20%), cesium carbonate (2equiv) and dimethylsulfoxide (0.5M). The resulting mixture was bubbled with nitrogen for 10 minutes and stirred at 120°C for 3 days. After cooling, water and ethyl acetate (EA) were added, and the mixture was filtered. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with brine, and the organic phase was washed with anhydrous Na 2 SO 4 dry. Using PE:EA=8:1 as eluent, the obtained solution was purified by silica gel chromatography to obtain the target product 0007 (brown viscous liquid, yield 75%).

[0107] Synthesis of 2-bromo-N-isopropyl-aniline 1102:

[0108]

[0109] 15 ml of acetone and 75 ml of acetic acid were added to...

Embodiment 4

[0137] Synthesis of complex 31

[0138] Synthesis of 2-bromo-N-isobutyl-aniline 4102:

[0139]

[0140] 15 ml of acetone and 75 ml of acetic acid were added to a solution of 8 g of o-bromoaniline 1101 in 150 ml of dichloromethane. 6 ml of borane dimethyl sulfide solution was added at 0°C, followed by stirring overnight at room temperature. After the reaction was complete, 25 wt% ammonia solution was added to adjust the pH to 8. After adding 50 ml of water, it was extracted three times with dichloromethane. The organic phase was collected and dried with anhydrous sodium sulfate, and spin-dried to obtain the crude product of compound 4102, which was directly used in the next step (yellow oil, yield 96%).

[0141] Synthesis of phenylenediamine derivative 4103:

[0142]

[0143] Add 2-bromo-N-(isopropyl)-aniline 4102 (1 equiv), 2-(3-amino-phenolyl)-9-(2-pyridyl)carbazole 0005 ( 1.1 equiv), palladium acetate (5%), J-phos (2-(dicyclohexylphosphino)biphenyl, 5%), sodiu...

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Abstract

The invention belongs to the technical field of organic electroluminescent materials and provides a bivalent platinum coordination compound and the application thereof as well as an organic photoelectric device. The bivalent platinum coordination compound provided by the invention has a chemical structure as shown in a formula I and is a blue light emitting material. The blue light emitting material serves as a doping material in OLED light-emitting devices and equipment, and the peak value of blue light emitted by the blue light emitting material ranges between 450 and 470 nm. Benzimidazole carbene is introduced into a ligand structure of the bivalent platinum coordination compound; the benzimidazole carbene structure has proper triplet energy, has a more stable carbon platinum coordination bond compared with a nitrogen platinum coordination bond, and has a more stable excited state conjugated system compared with the imidazole carbene structure. Therefore, the whole blue light spectrum is narrower, molecules are more stable in photoluminescence and device electroluminescence, the development of the blue light emitting material is promoted and the properties of light-emitting devices are improved.

Description

technical field [0001] The present invention relates to the technical field of optoelectronic materials, in particular to a divalent platinum complex, its application and an organic optoelectronic device using the divalent platinum complex as a light-emitting material. Background technique [0002] Compounds capable of absorbing and / or emitting light are applicable to a variety of optical and optoelectronic devices, including but not limited to light absorbing devices such as solar, photosensitive, organic light emitting diodes (OLEDs), light emitting devices, or both light absorbing and light emitting devices. Emissive capable devices and related applications for biomarkers. Much research has been devoted to the discovery of organic and organometallic materials for use in optical and electroluminescent devices. Significant progress has been made in the research of optoelectronic materials (red and green organometallic materials used as phosphorescent materials, blue organo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 杭晓春盛永健
Owner NANJING UNIV OF TECH