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Phosphorescent Osmium (II) complexes and uses thereof

a technology of phosphorescent osmium and complexes, which is applied in the field of phosphorescent compounds, can solve the problems of low efficiency, poor viewing angle, and lcd technology

Inactive Publication Date: 2007-01-04
TAO YE +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The new Os(II) complexes achieve high luminescence efficiency and stability, enabling red, blue, and green phosphorescent emissions, improving OLED and PLED performance by utilizing both singlet and triplet excitons effectively.

Problems solved by technology

While the technology of LCDs has various limitations such as low efficiency, poor viewing angles, slow switching speed and narrow temperature ranges, the main advantages of OLEDs are full color, high efficiency, large viewing angles, high switching speed, and low operational temperature.
While some materials meet or exceed some of the requirements for commercial displays, none are believed to meet them all.
Efficient and stable red and blue emitters are especially lacking.
The design and synthesis of red emitting complexes is intrinsically difficult because their luminescence quantum yield tends to their ionic nature observed in the traditional design involving Os(II) complexes such as [Os(bpy)3][PF6]2, where bpy=2,2′-bipyridine; [Carlson, B. et al., J. Am. Chem. Soc.
The positively charged Os(II) fragments and their counter anions may undergo significant drifting under high electric field during device operation towards the cathode and the anode, respectively, leading to instability in device performance and a relatively long response time.

Method used

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  • Phosphorescent Osmium (II) complexes and uses thereof
  • Phosphorescent Osmium (II) complexes and uses thereof
  • Phosphorescent Osmium (II) complexes and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of [Os(fppz)2(CO)2]

[0057] To a 50 mL reaction flask, it was charged with 3-trifluoromethyl-5-(2-pyridyl) pyrazole (fppzH, 296 mg, 1.39 mmol), pulverized Os3(CO)12 (200 mg, 0.22 mmol), and 25 mL of anhydrous diethylene glycol monoethyl ether. The solution was maintained at 180˜190° C. for 24 hours. After then, the solvent was evaporated and the solid material was sublimed under reduced pressure (300 mtorr / 210° C). The sublimate was further crystallized from a mixture of CH2Cl2 and hexane, giving the product [Os(fppz)2(CO)2] as colorless needle-like crystals (267 mg, 0.40 mmol) in 60% yield.

[0058] Spectral data: MS (EI, 192Os): m / z 672 (M+), 616 (M+—2CO). IR (CH2Cl2): ν(CO), 2043 (s), 1973 (s) cm−1. 1H NMR (500 MHz, d6-acetone, 294K): δ9.17 (ddd, JHH=6.0, 1.5, 1.0 Hz), 8.20 (ddd, JHH=8.0, 8.0, 1.5 Hz), 8.10 (ddd, JHH=8.0, 1.5, 1.0 Hz), 7.48 (ddd, JHH=8.0, 6.0, 1.5 Hz), 7.10 (s). 13C NMR (125 MHz, d6-acetone): δ177.6 (CO), 157.1 (CH), 155.8 (C), 151.7 (C), 144.1(q, 2JCF=35.5...

example 2

Synthesis of [Os(fmpz)2(CO)2]

[0059] 3-Trifluoromethyl-5-(4-methyl-2-pyridyl) pyrazole (fmpzH, 240 mg, 1.04 mmol) and finely pulverized Os3(CO)12 (150 mg, 0.165 mmol) were loaded in a 25 mL Carius tube and degassed. It was then sealed under vacuum and placed in an oven maintained at temperatures 180˜185° C. for 2.5 days, during which time its color changed gradually from light yellow to red-brown and finally to orange yellow. After stopped the reaction, the tube was cooled, opened and the content was dissolved in acetone. The insoluble material was filtered off, and the filtrate was dried under vacuum and the residue was sublimed (0.24 torr, 220° C.). The product was then subjected to recrystallization in CH2Cl2 and hexane, giving [Os(fmpz)2(CO)2] as colorless needle-like crystals (34 mg, 0.048 mmol) in 29% yield.

[0060] Spectral data: MS (EI, 192Os): m / z 700 (M+), 644 (M+—2CO). IR (CH2Cl2): v(CO), 2041 (s), 1970 (s) cm□1. 1H NMR (400 MHz, d6-acetone, 294K): 8.97 (d, JHH=6.0 Hz), 7.9...

example 3

Synthesis of [Os(bptz)2(CO)2]

[0061] To a 50 mL reaction flask, it was charged with 3-t-butyl-5-(2-pyridyl) 1,2,4-triazole (bptzH, 273 mg, 1.35 mmol), pulverized Os3(CO)12 (200 mg, 0.22 mmol), and 25 mL of anhydrous diethylene glycol monoethyl ether. The solution was maintained at 180° C. for 24 hours. After then, the solvent was evaporated and the residue was washed with water. The crude product was crystallized from a mixture of acetone and hexane, giving [Os(bptz)2(CO)2] as colorless block-shaped crystals (309 mg, 0.48 mmol) in 72% yield.

[0062] Spectral data: MS (EI, 192Os): m / z 651 (M+), 591 (M+—2CO). IR (CH2Cl2): v(CO), 2041 (s), 1970 (s) cm−1. 1H NMR (400 MHz, acetone-d6, 298K): δ9.16 (dd, JHH=6.8, 1.2 Hz), 8.25 (ddd, JHH=7.4, 6.8, 1.2 Hz), 8.10 (dd, JHH=7.4, 1.2 Hz), 7.55 (ddd, JHH=6.8, 7.4, 1.2 Hz), 1.12 (s, tBu). Anal. Calcd for C24H26N8O2Os: C, 44.43; N, 17.27; H, 4.04. Found: C, 44.26; N, 17.60; H, 4.30.

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Abstract

There is disclosed herein phosphorescent compounds, uses thereof, and devices including organic light emitting diode (OLEDs) including such compounds. Compounds of interest include: wherein A is Os or Ru The anionic chelating chromophores NˆN, which are formed by connecting one pentagonal ring structure containing at least two nitrogen atoms to a hexagonal pyridine type of fragment via a direct carbon-carbon linkage. L is a neutral donor ligand; the typical example includes carbonyl, pyridine, phosphine, arsine and isocyanide; two neutral L's can also combine to produce the so-called chelating ligand such as 2,2′-bipyridine, 1,10-phenanthroline and N-heterocyclic carbene (NHC) ligand, or bidentate phosphorous ligands such as 1,2-bis(diphenylphosphino)ethane, 1,2-bis(diphenylphosphino)benzene. L can occupy either cis or trans orientation. When L occupies the trans position, the preferred structure contains both the hexagonal fragment of NˆN as well as its pentagonal fragment located at the trans position respect to their counterparts of the second NˆN chromophore. When L occupies the cis position, the preferred structure consists of the pentagonal unit of NˆN chromophores residing opposite to the L. X,1 X2 and X3 independently are C or N; when X2 is N, R1 is omitted, when X3 is N, R2 is omitted, R1 is H, C1-C8 alkyl, C1-C8 substituted phenyl or C1-C4 perfluoroalkyl, R2 is H, F or cyano substituent, X4 is either C or N; X4 may locate at any position of the hexagonal ring, when X4 is N and R3 and R4 are not linked to X4, R3 is H, methyl or C1-C3 small alkyl, R4 is H, methyl or C1-C3 small alkyl, or R3 and R4 together form an additional conjugated unit with structure

Description

FIELD OF THE INVENTION [0001] The invention relates to phosphorescent compounds and uses thereof. CROSS-REFERENCE TO RELATED APPLICATIONS [0002] This application is a continuation of U.S. Ser. No. 10 / 981,755 filed on Nov. 5, 2004 which is incorporated herein by reference. BACKGROUND [0003] It has long been felt that a technically viable emissive display technology could compete with the currently dominating technology of liquid crystal displays (LCDs), and OLEDs are presently considered well placed to do so. While the technology of LCDs has various limitations such as low efficiency, poor viewing angles, slow switching speed and narrow temperature ranges, the main advantages of OLEDs are full color, high efficiency, large viewing angles, high switching speed, and low operational temperature. Therefore, organic light emitting diodes (OLEDs) and polymer light emitting diodes (PLEDs) have attracted a tremendous amount of research interests from both academia and industry in the past de...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01L51/00C07F15/00C09K11/06H05B33/14H10K99/00
CPCC07F15/002C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/185H05B33/14H01L51/0059H01L51/0062H01L51/0081H01L51/0088H01L51/5016H01L51/0042H10K85/146H10K85/649H10K85/631H10K85/348H10K85/324H10K50/11H10K2101/10
Inventor TAO, YECHI, YUNTUNG, YUNG-LIANGCARTY, ARTHUR
Owner TAO YE
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