Phosphorescent tetradentate metal complexes having modified emission spectra

A compound and composition technology, applied in the field of phosphorescent tetradentate metal complexes with improved emission spectrum, can solve the problems of low stability, low-efficiency luminescence or absorption, poor processability, etc.

Active Publication Date: 2014-12-24
THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIV OF ARIZONA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Despite the remarkable progress in the research devoted to optical and optoelectronic materials, many currently available materials still show many disadvantages, including poor processability, low efficiency of light emission or absorption, and less than ideal stability, etc.

Method used

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  • Phosphorescent tetradentate metal complexes having modified emission spectra
  • Phosphorescent tetradentate metal complexes having modified emission spectra
  • Phosphorescent tetradentate metal complexes having modified emission spectra

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0159] The platinum complex PtN1N can be prepared according to the following scheme:

[0160]

[0161] Synthesis of 2-bromo-9H-carbazole 1:

[0162]

[0163] 4'-Bromo-2-nitrobiphenyl (22.40g, 80.55mmol) and P(OEt) 3 (150 mL) was added to a three-neck round bottom flask equipped with a magnetic stir bar and condenser under nitrogen. The mixture was heated to 150°C-160°C in an oil bath for 30 hours, cooled to ambient temperature, and excess P(OEt) was removed by distillation under high vacuum 3 . The residue was recrystallized in toluene to give the desired product 2-bromo-9H-carbazole (8.30 g) as white crystals. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1) as eluents to obtain the desired product 2-bromo-9H-carbazole 1 (2.00 g, 52% yield). 1 H NMR (DMSO-d 6 ,400MHz): δ7.17(t,J=7.6Hz,1H),7.28(dd,J=8.0,1.6Hz,1H),7.41(t,J=7.6Hz,1H),7.49(d,J= 8.4Hz, 1H), 7.65(d, J=1.6Hz, 1H),...

Embodiment 2

[0183] The platinum complex PtN1NMe can be prepared according to the following scheme:

[0184]

[0185] Synthesis of 9-(2'-nitrobiphenyl-4-yl)-2-(1H-pyrazol-1-yl)-9H-carbazole 6:

[0186]

[0187] 2-(1H-pyrazol-1-yl)-9H-carbazole 5 (1.35g, 5.78mmol, 1.0 equivalent), 4'-iodo-2-nitrobiphenyl 3 (2.26g, 6.94mmol, 1.2 Equivalent), K 3 PO 4 (2.58g, 12.14mmol, 2.1eq) and CuI (55mg, 0.29mmol, 0.05eq) were added to a dry pressure tube equipped with a magnetic stir bar. The tube was evacuated and then backfilled with nitrogen. The evacuation and backfilling process was repeated twice, then 1,2-cyclohexanediamine (0.33 g, 290 uL, 2.89 mmol, 0.5 equiv) and dioxane (20 mL) were added. The mixture was bubbled with nitrogen for 30 minutes and the tube was sealed. The mixture was stirred for 3 days in an oil bath at a temperature of 110-120°C and then cooled to ambient temperature. The solvent was removed under reduced pressure and the residue was purified by column chromatograph...

Embodiment 3

[0198] The platinum complex PtN1N-tBu can be prepared according to the following scheme:

[0199]

[0200] Synthesis of 9-(4-tert-butylpyridin-2-yl)-2'-(1H-pyrazol-1-yl)-9H-2,9'-dicarbazole ligand N1N-tBu:

[0201]

[0202] 2'-(1H-pyrazol-1-yl)-9H-2,9'-dicarbazole 7 (398mg, 1.0mmol, 1.0eq), Pd 2 (dba) 3 (46mg, 0.05mmol, 0.05 equivalent), JohnPhos (30mg, 0.1mmol, 0.1 equivalent) and t BuONa (154 mg, 1.6 mmol, 1.6 equiv) was added to a dry pressure Schlenk tube equipped with a magnetic stir bar. The tube was then evacuated and backfilled with nitrogen. The process of evacuation and backfilling was repeated twice, then anhydrous toluene (4 mL), dioxane (4 mL) and 2-bromo-4-tert-butylpyridine (418 mg, 2.0 mmol, 2.0 equiv) were added under nitrogen . The tube was sealed and the mixture was stirred for 2 days in an oil bath at a temperature of 95-105°C. The mixture was then cooled to ambient temperature. The solvent was removed under reduced pressure and the residue was...

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Abstract

Multidentate metal complexes useful as phosphorescent emitters in display and lighting applications having the following structures.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to U.S. Application 61 / 833,091, filed June 10, 2013, entitled "Phosphorescent Tetradentate Metal Complexes," which is hereby incorporated by reference in its entirety . technical field [0003] The present disclosure relates to multidentate metal complexes and compositions containing the same, which are useful as emitters in display and lighting applications, and devices containing these complexes and compositions. Background technique [0004] Compounds capable of absorbing and / or emitting light are ideally suited for use in a wide variety of optical and optoelectronic devices, including for example light-absorbing devices such as sunlight- and light-sensitive devices, organic light-emitting diodes (OLEDs), light-emitting devices, or capable of both Light-absorbing and light-emitting devices, and as markers for biological applications. [0005] figure 1 Examples of OLEDs are describ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/54H01L51/46
CPCC09K2211/1007C09K2211/1029C09K2211/1044C07F15/0086Y02E10/549C09K11/06C09K2211/185A61K31/4427H10K85/346C09K2211/18H10K50/11H10K2101/10
Inventor J.李G.李J.布鲁克斯
Owner THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIV OF ARIZONA
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