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Platinum complexes and devices

A compound and independent technology, applied in the field of platinum complexes, can solve the problems of poor processability, less than ideal stability, low efficiency, etc.

Inactive Publication Date: 2015-06-10
ARIZONA STATE UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Despite remarkable progress in research dedicated to optical and electro-optic materials, currently available materials exhibit a number of disadvantages including, inter alia, poor processability, inefficient emission or absorption, and less than ideal stability

Method used

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  • Platinum complexes and devices
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0446] The platinum complex PtON12 was prepared according to the following scheme:

[0447]

[0448] Synthesis of 1-(3-methoxyphenyl)-1H-indazole 1:

[0449]

[0450] To a dry pressure tube equipped with a magnetic stir bar was added 1H-indazole (3.54 g, 30 mmol, 1.0 equiv), 1-iodo-3-methoxybenzene (8.07 g, 36 mmol, 1.2 equiv), CuI (0.29 g , 1.5mmol, 0.05 equivalent), K 2 CO 3 (13.37 g, 63 mmol, 2.1 equiv) and trans-1,2-cyclohexanediamine (0.65 g, 6 mmol, 0.2 equiv). The tube was then taken into the glove box, and the solvent toluene (40 mL) was added. The mixture was bubbled with nitrogen for 5 minutes and the tube was sealed. The tube was removed from the glove box, and the mixture was stirred in an oil bath at 105-115°C for 3 days. The mixture was cooled to ambient temperature, diluted with ethyl acetate, then filtered and washed with ethyl acetate. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane and...

Embodiment 2

[0462] The platinum complex PtON12-tBu was prepared according to the following scheme:

[0463]

[0464] Synthesis of 2-(3-(1H-indazol-1-yl)phenoxy)-9-(4-tert-butylpyridin-2-yl)-9H-carbazole ligand ON12-tBu:

[0465]

[0466] To a dry Shlenck tube fitted with a magnetic stir bar was added 3-(1H-indazol-1-yl)phenol 2 (630 mg, 3.0 mmol, 1.0 equiv), 9-(4-tert-butylpyridin-2-yl) -2-Bromo-9H-carbazole (1365mg, 3.6mmol, 1.2eq), CuI (57mg, 0.3mmol, 0.1eq), picolinic acid (74mg, 0.6mmol, 0.2eq) and K 3 PO 4 (1273 mg, 6.0 mmol, 2.0 equiv). The tube was evacuated and backfilled with nitrogen. The vacuum and backfill procedure was repeated two more times. Then the solvent DMSO (9 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at a temperature of 90-100° C. for 3 days and then cooled to ambient temperature. Water was added to dissolve the solids. The mixture was extracted three times with ethyl acetate. The combined organic layers were washed...

Embodiment 3

[0472] The platinum complex PtON13 can be prepared according to the following scheme:

[0473]

[0474] Synthesis of 4-bromo-1-(3-methoxyphenyl)-1H-pyrazole 3:

[0475]

[0476] To a dry pressure tube equipped with a magnetic stir bar was added 4-bromo-1H-pyrazole (3674 mg, 25 mmol, 1.0 eq), CuI (95 mg, 0.5 mmol, 0.02 eq) and K 2 CO 3 (7256 mg, 52.5 mmol, 2.1 equiv). Then trans-1,2-cyclohexanediamine (570 mg, 5 mmol, 0.2 equiv), 1-iodo-3-methoxybenzene (3.57 mL, 30 mmol, 1.2 equiv) and Solvent dioxane (50 mL). The mixture was bubbled with nitrogen for 5 minutes. Seal the tube before removing it from the glove box. The mixture was stirred at a temperature of 100° C. in an oil bath for two days. The mixture was then cooled to ambient temperature, filtered, and washed with ethyl acetate. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane and ethyl acetate (20:1-15:1) as eluent to give the desired product 4-b...

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Abstract

Platinum compounds of Formulas I and II useful in a variety of devices, such as, for example organic-light emitting diodes (OLEDs).

Description

[0001] Cross References to Related Applications [0002] This application claims U.S. Serial No. 61 / 890,545, entitled "PLATINUM COMPLEXES, DEVICES, AND USES THEREOF," both filed October 14, 2013, and entitled "PLATINUM COMPLEXES, DEVICES, AND USES THEREOF." PLATINUM COMPLEXES, DEVICES, AND USES THEREOF" of US Serial No. 61 / 890,580, both of which are incorporated herein by reference in their entirety. technical field [0003] The present invention relates to platinum complexes and devices comprising said platinum complexes. Background technique [0004] Compounds capable of absorbing and / or emitting light are ideally suited for use in a wide variety of optical and electroluminescent devices, including, for example, light-absorbing devices such as solar-sensitive and photosensitive devices, organic light-emitting diodes (OLEDs), light-emitting Devices, or devices capable of both light absorption and light emission and as markers for biological applications. Much research has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/00H01L51/54H01L51/46H10K99/00
CPCC07D231/12C07D231/38C07D231/56C07D401/14C07D403/14C07D491/048C07D519/00C07F15/0086C07F19/00C09K11/06C09K2211/185H10K85/346H10K50/11H10K2101/10H10K30/50Y02E10/549C07F15/00H10K50/00H10K30/00C09K2211/1007C09K2211/1022C09K2211/1044
Inventor J·李G·李J·布鲁克斯
Owner ARIZONA STATE UNIVERSITY
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