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US20130203996A1 - Synthesis of Four Coordinated Palladium Complexes and Their Applications in Light Emitting Devices Thereof - Google Patents

Synthesis of Four Coordinated Palladium Complexes and Their Applications in Light Emitting Devices Thereof Download PDF

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US20130203996A1
US20130203996A1 US13/695,337 US201113695337A US2013203996A1 US 20130203996 A1 US20130203996 A1 US 20130203996A1 US 201113695337 A US201113695337 A US 201113695337A US 2013203996 A1 US2013203996 A1 US 2013203996A1
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Jian Li
Eric Turner
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Definitions

  • the present disclosure relates to palladium complexes which are capable of absorbing and/or emitting light and are thus useful as an emissive or absorption material in a device.
  • Photo-absorbing devices such as solar and photo-sensitive devices
  • photo-emitting devices such as organic light emitting diodes (OLEDs)
  • OLEDs organic light emitting diodes
  • the present invention relates to palladium complexes that exhibit photo-absorption and photo-emission, to methods of making such compounds, and to applications thereof, including optical devices comprising the compounds.
  • the compounds are represented by the formula:
  • each R 1 and R 2 in (R 1 ) 2 and (R 2 ) 2 independently represents hydrogen, optionally substituted C 1 -C 4 alkyl, halogen, hydroxyl, amino, nitro, or thiol;
  • R 3 represents methyl, ethyl, propyl, or butyl
  • Y 1a represents O, S, NR 4a , wherein R 4a represents optionally substituted C 1 -C 4 alkyl; Si(R 4b ) 2 , wherein each R 4b in (R 4b ) 2 independently represents optionally substituted C 1 -C 4 alkyl; or C(R 4c ) 2 , wherein each R 4c in (R 4c ) 2 represents hydrogen or optionally substituted C 1 -C 4 alkyl;
  • n is an integer 0 or 1;
  • Y 1b when present, represents O, S, NR 5a , wherein R 5a represents optionally substituted C 1 -C 4 alkyl; Si(R 5b ) 2 , wherein each R 5b in (R 5b ) 2 independently represents optionally substituted C 1 -C 4 alkyl; or C(R 5c ) 2 , wherein each R 5c in (R 5c ) 2 represents hydrogen or optionally substituted C 1 -C 4 alkyl;
  • each of Y 2a , Y 2b , Y 2c , and Y 2d independently represents N, NR 6a , or CR 6b , wherein each of R 6a and R 6b independently represents hydrogen, optionally substituted C 1 -C 4 alkyl, halogen, hydroxyl, amino, nitro, or thiol;
  • each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c , and Y 4d independently represents N, O, S, NR 6a , CR 6b , wherein each of R 6a and R 6b independently represents hydrogen or optionally substituted C 1 -C 4 alkyl; or Z(R 6c ) 2 , wherein Z is C or Si, and wherein each R 6c in (R 6c ) 2 independently represents hydrogen or optionally substituted C 1 -C 4 alkyl;
  • n is an integer 1 or 2;
  • each of Y 2a and Y 2d is CH and each of Y 2b and Y 2c is N, then at least one of Y 4a , Y 4b , Y 3a , or Y 3d is not N;
  • each of Yea and Y 2d is CH, and each of Y 2b and Y 2c is N, then at least one of Y 3b or Y 3c is not N.
  • optical devices such as organic light emitting devices and luminescent display devices that comprise one or more compounds of the invention as a functional material, such as a light-emitter or absorber, or both.
  • FIG. 1 is a drawing of a cross-section of an exemplary organic light-emitting diode (OLED).
  • OLED organic light-emitting diode
  • FIG. 2 is a photoluminescence spectrum produced from a specific embodiment, 2-(3-(pyridin-2-yl)phenoxy)-6-(pyridin-2-yloxy)phenyl]Pd(II) (Pd003) taken in degassed dichloromethane at room temperature, wherein the quantum yield was about 0.1 and the luminescence lifetime was about 11 ⁇ sec.
  • the chemical structure of Pd003 is also illustrated in the inset.
  • FIG. 3 is a photoluminescence spectrum produced from a specific embodiment, 2-(3-(pyridin-2-yl)phenoxy)-6-(pyridin-2-yloxy)phenyl]Pd(II) (Pd003) doped into a polymethylmethacrylate (PMMA) thin film at room temperature, which shows a thin film photoluminescence quantum yield over 70%.
  • PMMA polymethylmethacrylate
  • FIG. 4 illustrates (A) a specific embodiment, and (B) a photoluminescence spectrum of the same in a solution of dichloromethane, obtained at room temperature wherein the quantum yield was about 0.16 and the luminescent lifetime was about 30 ⁇ sec.
  • FIG. 5 illustrates (A) a specific embodiment, (B) an electroluminescent spectrum from a OLED device comprising the specific embodiment, (C) a plot of external quantum efficiency vs. current density for a Pd003 based device, and (D) a current vs. voltage plot at a 1% doping level.
  • Ranges can be expressed herein as from “about” one particular value, and/or to “about” another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. For example, if the value “10” is disclosed, then “about 10” is also disclosed. It is also understood that each unit between two particular units are also disclosed. For example, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are also disclosed.
  • the terms “optional” or “optionally” means that the subsequently described event or circumstance can or can not occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.
  • alkyl as used herein is a branched or unbranched saturated hydrocarbon group of 1 to 24 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, s-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, and the like.
  • the alkyl group can be cyclic or acyclic.
  • the alkyl group can be branched or unbranched.
  • the alkyl group can also be substituted or unsubstituted.
  • the alkyl group can be substituted with one or more groups including, but not limited to, optionally substituted alkyl, cycloalkyl, alkoxy, amino, ether, halide, hydroxy, nitro, silyl, sulfo-oxo, or thiol, as described herein.
  • a “lower alkyl” group is an alkyl group containing from one to six (e.g., from one to four) carbon atoms.
  • amine or “amino” as used herein are represented by the formula NA 1 A 2 A 3 , where A 1 , A 2 , and A 3 can be, independently, hydrogen or optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.
  • halide refers to the halogens fluorine, chlorine, bromine, and iodine.
  • hydroxyl as used herein is represented by the formula —OH.
  • nitro as used herein is represented by the formula —NO 2 .
  • nitrile as used herein is represented by the formula —CN.
  • thiol as used herein is represented by the formula —SH.
  • compositions of the invention Disclosed are the components to be used to prepare the compositions of the invention as well as the compositions themselves to be used within the methods disclosed herein.
  • these and other materials are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these materials are disclosed that while specific reference of each various individual and collective combinations and permutation of these compounds can not be explicitly disclosed, each is specifically contemplated and described herein. For example, if a particular compound is disclosed and discussed and a number of modifications that can be made to a number of molecules including the compounds are discussed, specifically contemplated is each and every combination and permutation of the compound and the modifications that are possible unless specifically indicated to the contrary.
  • a metal when depicted as a portion of a chemical structure, the notation can refer to a single metal atom and/or to a plurality of atoms. In one aspect, a notation for a metal refers to a single metal atom. In another aspect, a notation for a metal refers to a plurality of metal atoms.
  • the invention comprises phosphorescent multidentate, for example, tridentate and/or tetradentate, palladium (II) complexes.
  • multidentate palladium complexes can be modified and/or specifically tailored to tune the emission spectra from, for example, ultraviolet to near-infrared emission.
  • the inventive compositions can provide improved stability and efficiency over conventional light emitting materials.
  • the inventive compositions can be useful as luminescent labels, absorbers, emitters, or a combination thereof.
  • inventive compositions are represented by the general formula:
  • Ar1, Ar2, Ar3, and Ar4, if present, represent aromatic groups, wherein each E represents an optional linking atom, such as, for example, carbon or oxygen, and wherein R, if present, represents an ancillary ligand
  • an ancillary ligand can comprise one or more of the following:
  • R 1 -R 10 of the ancillary ligand each independently represent a hydrogen atom, an alkyl group, a haloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono- or di-alkylamino group, a mono- or diaryl amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a hydroxyl group, amercapto group, a hal
  • an ancillary ligand can comprise a hydrogen atom.
  • an ancillary ligand can comprise an alkyl group.
  • an ancillary ligand can comprise a haloalkyl group.
  • an ancillary ligand can comprise a aralkyl group.
  • an ancillary ligand can comprise a alkenyl group.
  • an ancillary ligand can comprise an alkynl group.
  • an ancillary ligand can comprise an aryl group.
  • an ancillary ligand can comprise an amino group.
  • an ancillary ligand can comprise an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, an acyloxy group, or a combination thereof.
  • an ancillary ligand can comprise an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a hydroxyl group, amercapto group, a halogen atom, a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydrazino group, a substituted silyl group, a polymerizable group, or a combination thereof.
  • an ancillary ligand can comprise a group or groups difference from those specifically recited herein, and the present invention is not intended to be limited to any particular ancillary ligand.
  • inventive composition can be grouped and illustrated by ligand class.
  • inventive composition can be represented by the general formula:
  • compositions within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • each E represents an optional linking atom, such as, for example, carbon or oxygen
  • R represents an ancillary ligand
  • each C represents an aromatic group.
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • a specific example of an inventive composition within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • inventive compositions within this ligand class can comprise:
  • inventive composition can be represented by the general formula:
  • each N represents a nitrogen substituted aromatic group
  • each E represents an optional linking atom, such as, for example, carbon or oxygen
  • C represents an aromatic group
  • each R 1 and R 2 in (R 1 ) 2 and (R 2 ) 2 independently represents hydrogen, optionally substituted C 1 -C 4 alkyl, halogen, hydroxyl, amino, nitro, or thiol;
  • Y 1a represents O, S, NR 4a , wherein R 4a represents optionally substituted C 1 -C 4 alkyl;
  • Si(R 4b ) 2 wherein each R 4b in (R 4b ) 2 independently represents optionally substituted C 1 -C 4 alkyl; or C(R 4c ) 2 , wherein each R 4c in (R 4c ) 2 represents hydrogen or optionally substituted C 1 -C 4 alkyl;
  • n is an integer 0 or 1;
  • Y 1b when present, represents O, S, NR 5a , wherein R 5a represents optionally substituted C 1 -C 4 alkyl; Si(R 5b ) 2 , wherein each R 5b in (R 5b ), independently represents optional
  • each of Y 2a and Y 2d is CH and each of Y 2b and Y 2c is N, then at least one of Y 4a , Y 4b , Y 3a , or Y 3d is not N.
  • the following compound is not included in the above formula:
  • m is 1, each of Y 2a and Y 2d is CH and each of Y 2b and Y 2c is N; however, each of Y 4a , Y 4b , Y 3a , or Y 3d is N. It follows that the preceding example, according to this embodiment, is not included within the general formula above. In the practice of this embodiment, similar analysis can be used to determine whether or not a compound is or is not included within the general formula above.
  • n is 0, m is 2, each of Y ea and Y 2d is CH, and each of Y 2b and Y 2c is N. However, each of Y 3b and Y 3c is N. It follows that the preceding example, according to this embodiment, is not included within the general formula above. Once more, in the practice of this embodiment, similar analysis can be used to determine whether or not a compound is or is not included within the general formula above.
  • the compound is represented by the formula:
  • the compounds of the invention can be made using a variety of methods.
  • Y 1a is O
  • the compounds can be provided according to Scheme 1.
  • step “a” can be accomplished, for example, by using a catalytic amount of a coupling reagent, such as Cu 2 O, which couples alcohols, particularly phenols, with halogenated phenyl groups.
  • a coupling reagent such as Cu 2 O, which couples alcohols, particularly phenols, with halogenated phenyl groups.
  • the variable “X” in Scheme 1 above represents a halogen (i.e., Cl, F, I, Br), and is preferably I when used in conjunction with Scheme 1.
  • each side of a ligand which complexes a metal can be made independently using a variety of methods, which, in one aspect, depend on whether Y 3a is N or C.
  • the precursor when Y 4a is N, the precursor can, in one aspect, be provided according to Scheme 2(A), wherein a halogenated phenyl compound is reacted with a pyrazole, imadazole, 1H-1,2,3-triazole, 1H-tetrazole, or 2H-pentazole.
  • the halogenated phenyl compound can comprise any halogen (X), including Cl, Br, F, or I, but is preferably I, which is typically more reactive in a coupling reaction.
  • the halogenated phenyl compound and corresponding pyrazole, imadazole, 1H-1,2,3-triazole, 1H-tetrazole, or 2H-pentazole can be coupled using a metallic and/or organometallic coupling agent, such as, for example, Cu 2 O.
  • a metallic and/or organometallic coupling agent such as, for example, Cu 2 O.
  • an acid scavenger such as, for example, syn-2-pyridinealdoxime, in a small molar ratio, for example, about 20 mol %.
  • a different protocol can be used to provide the precursor.
  • a halogenated phenyl as discussed above can be reacted with a tetrazole, 1,2,3-triazole, pyrazole, or pyrrole to achieve a carbon-carbon bond coupling, as opposed to a carbon-nitrogen bond coupling as shown in Scheme 2(A).
  • the carbon-carbon bond coupling can also be achieved using an organometallic catalyst, such as, for example, a Pd(II) catalyst (e.g., Pd(OAc) 2 ) in a small molar ratio.
  • such an organometallic catalyst can optionally be used together with an excess of a salt mixture, such as KI and/or CuI.
  • a salt mixture such as KI and/or CuI.
  • the compounds of the invention can be useful in a variety of optical applications.
  • the inventive compounds can be useful in organic light emitting diodes (OLED)s, luminescent devices and displays, and/or other light emitting devices.
  • OLED organic light emitting diodes
  • FIG. 3 for example, a specific embodiment, 2-(3-(pyridin-2-yl)phenoxy)-6-(pyridin-2-yloxy)phenyl]Pd(II) exhibits photoluminescence (absorption of light followed by emission of light) across a range of wavelengths, including a narrow blue emission and other emission bands out to the red to near-IR region of the spectrum.
  • the emission (and absorption) profile of the compounds can be tuned by varying the structure of the ligand surrounding the metal center.
  • compounds having a ligand with electron withdrawing substituents can, in one aspect, generally exhibit different optical properties, including emission and absorption, than compounds having a ligand with electron donating substituents.
  • a chemical structural change can affect the electronic structure of the compound, thereby affecting the absorption and emission properties of the compound.
  • the compounds of the present invention can be tailored or tuned to a specific application that desires a particular emission or absorption characteristic.
  • One of skill in the art, in possession of this disclosure could readily design and/or select an appropriate multidentate palladium compound, in accordance with the various aspects described herein, to use in a particular application.
  • FIG. 1 illustrates a cross-sectional view of an exemplary OLED 100 , which includes substrate 102 with an anode 104 , which is typically a transparent material, such as indium tin oxide, a layer of hole-transporting material(s) (HTL) 106 , a layer of light processing material 108 , such as an emissive material (EML) including an emitter and a host, a layer of electron-transporting material(s) (ETL) 110 , and a metal cathode layer 112 .
  • anode 104 which is typically a transparent material, such as indium tin oxide, a layer of hole-transporting material(s) (HTL) 106 , a layer of light processing material 108 , such as an emissive material (EML) including an emitter and a host, a layer of electron-transporting material(s) (ETL) 110 , and a metal cathode layer 112 .
  • EML emissive material
  • the layer of light processing material 108 can comprise one or more compounds of the present invention optionally together with a host material.
  • the host material if present, can be any suitable host material known in the art.
  • the emission color of an OLED can be determined by the emission energy (optical energy gap) of the light processing material 108 , which as discussed above can be tuned by tuning the electronic structure of the emitting compounds and/or the host material.
  • Both the hole-transporting material in the HTL layer 106 and the electron-transporting material(s) in the ETL layer 110 can comprise any suitable hole-transporter known in the art. A selection of which is well within the purview of those skilled in the art.
  • Phosphorescent OLEDs i.e., OLEDs with phosphorescent emitters
  • OLEDs with phosphorescent emitters typically have higher device efficiencies that other OLEDs, such as fluorescent OLEDs.
  • Light emitting devices based on electrophosphorescent emitters are described in more detail in WO2000/070655 to Baldo et al., which is incorporated herein by this reference for its teaching of OLEDs, and in particular phosphorescent OLEDs.
  • a pressure vessel was charged with a magnetic stir bar, resorcinol (110 mmol), 2-bromopyridine (100 mmol), 1-methylimidazole (5 mmol), and potassium carbonate (200 mmol). Pyridine (80 mL) was added and bubbled with nitrogen for 20 minutes before copper(I) iodide (10 mmol) was added and bubbled 10 minutes further.
  • the vessel was sealed and heated to 140° C. while stirring. After 2 days, the solution was allowed to cool. The solids were filtered off and rinsed with a 50:50 mixture of toluene and methanol.
  • a pressure vessel was charged with a magnetic stir bar, 3-(pyridin-2-yloxy)phenol (50 mmol), 2,6-dibromopyridine (50 mmol), 1-methylimidazole (25 mmol), and potassium carbonate (100 mmol).
  • Toluene 80 mL was added and bubbled with nitrogen for 20 minutes before copper(I) iodide (5 mmol) was added and the solution bubbled for 10 minutes further.
  • the vessel was sealed and heated to 140° C. while stirring. After 2 days, the solution was allowed to cool and the solids were filtered off and rinsed with dichloromethane. The filtrate was added to a separatory funnel containing DCM and water.
  • the water phase was washed 3 times with 75 mL DCM, and the combined organic layers were washed once with pure water.
  • the organic layer was collected, dried with magnesium sulfate, filtered, and the filtrate reduced by rotary evaporation.
  • the resulting oil was purified by column chromatography using DCM over silica resulting in the pure product 2-(3-(3-bromophenoxy)phenoxy)pyridine with a 60% yield.

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US9382273B2 (en) 2016-07-05
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US9755163B2 (en) 2017-09-05
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US20180130960A1 (en) 2018-05-10
US10727422B2 (en) 2020-07-28
US20170005278A1 (en) 2017-01-05
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US20140114072A1 (en) 2014-04-24
JP2013530135A (ja) 2013-07-25
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