WO2011063083A1 - 3-coordinate copper (i) - carbene complexes - Google Patents

3-coordinate copper (i) - carbene complexes Download PDF

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Publication number
WO2011063083A1
WO2011063083A1 PCT/US2010/057169 US2010057169W WO2011063083A1 WO 2011063083 A1 WO2011063083 A1 WO 2011063083A1 US 2010057169 W US2010057169 W US 2010057169W WO 2011063083 A1 WO2011063083 A1 WO 2011063083A1
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complex
group
alkyl
aryl
heteroaryl
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French (fr)
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Mark Thompson
Peter Djurovich
Valentina Krylova
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University of Southern California USC
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University of Southern California USC
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Priority to CN201080059525.2A priority Critical patent/CN102695711B/zh
Priority to IN5146DEN2012 priority patent/IN2012DN05146A/en
Priority to CN201710567865.XA priority patent/CN107793437B/zh
Priority to EP10832153.0A priority patent/EP2501707B1/en
Priority to CN202410614438.2A priority patent/CN118561876A/zh
Priority to KR1020127015896A priority patent/KR101822668B1/ko
Priority to JP2012540041A priority patent/JP2013511532A/ja
Publication of WO2011063083A1 publication Critical patent/WO2011063083A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, The University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.
  • the present invention relates to phosphorescent copper complexes, and their use in organic light emitting devices (OLEDs). More particularly, the invention relates to phosphorescent complexes comprising a carbene ligand coordinated to a three coordinate copper atom, and devices containing such complexes.
  • Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • OLEDs organic light emitting devices
  • the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
  • OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
  • One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy) 3 , which has the structure:
  • organic includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices.
  • Small molecule refers to any organic material that is not a polymer, and "small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a
  • a dendrimer may be a "small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
  • top means furthest away from the substrate, while “bottom” means closest to the substrate.
  • first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is "in contact with” the second layer.
  • a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • solution processible means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
  • a ligand may be referred to as "photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material.
  • a ligand may be referred to as "ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
  • a first "Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or "higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level.
  • IP ionization potentials
  • a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
  • a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
  • the LUMO energy level of a material is higher than the HOMO energy level of the same material.
  • a "higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower” HOMO or LUMO energy level.
  • a first work function is "greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a "higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
  • Novel phosphorescent complexes are provided, the complexes comprising a carbene ligand coordinated to a three coordinate copper atom.
  • the carbene ligand has the formula:
  • Formula I. *C is a divalent carbon atom coordinated to a monovalent copper atom Cu.
  • Xi and X 2 are substituents independently selected from alkyl, amine, phosphine, heteroalkyl, aryl and heteroaryl. Xi and X 2 may be further substituted, and Xi and X 2 are optionally linked to form a cycle.
  • the carbene ligand is
  • each of Xi and X 2 independently forms a bond with *C.
  • a first bond is formed between *C and an atom ⁇ in substituent Xi
  • a second bond is formed between *C and an atom X' 2 in substituent X 2 .
  • ⁇ and X' 2 are independently selected from the group consisting of C, N, O, S and P.
  • the carbene ligand is monodentate.
  • Xi and X 2 are not joined to form a cycle. In another aspect, Xi and X 2 are joined to form a cycle.
  • the copper complex is neutral. In another aspect, the copper complex is charged.
  • the complex has the formula:
  • Yi is independently selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl. Yi is a monodentate ligand or a bidentate ligand. n is 1 or 2. Preferably, n is 2.
  • the complex has the formula: Formula III.
  • Yi and Y 2 are substituents that are independently selected from the group consisting of alkyl, heteroalkyl, aryl and heteroaryl. Yi and Y 2 may be further substituted. Yi and Y 2 are joined. Each of Yi and Y 2 form a bond with Cu. A first bond is formed between Cu and an atom ⁇ in substituent Yi and a second bond is formed between Cu and an atom Y' 2 in substituent Y 2 .
  • ⁇ is selected from the group consisting of N, P, *C, O, and S.
  • Y' 2 is selected from the group consisting of N, P, *C, tetravalent carbon, O, and S.
  • ⁇ is N.
  • the ring comprising Cu, ⁇ and Y' 2 is a 5- membered or 6-membered ring.
  • Y 1 is selected from the group consisting of pyridyl, pyrazole, alkyl amine, imidazole, benzimidazole, triazole, tetrazole, pyridazine, pyrimidine, pyrazine, triazine, tetrazine, oxazole, thiazole, benzoxazole and benzothiazole.
  • Yi- Y 2 is selected from the group consisting of:
  • ⁇ X is selected from the group consisting of NR, O, S, Se, CR 2 , and CO.
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Each ring is further substituted by a substituent selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • each R includes a substituent independently selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, azacarbazole,
  • Y Y 2 is selected from the group consisting of:
  • X is selected from the group consisting of NR, O, S, Se, CR 2 , and CO.
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Each ring is further substituted by a substituent selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • each R includes a substituent independently selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, azacarbazole, azadibenzofuran, and azadibenzothiophene.
  • Y is an unconjugated, monoanionic ligand containing BY 4 ⁇ , SO3Y “ , CY 4 " , Si0 4 " , OY 2 " , or SY 2 " .
  • Each Y is independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl and heteroaryl.
  • Yi is BY 4 " .
  • the ligand Yi comprises two
  • the ligand Yi has the formula:
  • the ligand Yi that comprises two monodentate ligands, at least one of which is BY 4 " is selected from the group consisting of:
  • Yi and Y 2 are independently selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl and phosphine.
  • Yi and Y 2 may be extended by fusion, e.g., benzanulation. Additionally, Yi and Y 2 may be further substituted with alkyl, aryl, donor or acceptor groups.
  • Y 3 and Y 4 are independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteralkyl and heteroaryl. In one aspect, Y 3 and Y 4 are joined to form a cycle, may be extended by fusion, e.g., benzanulation.
  • Yi is a bidentate ligand having the formula BY 4 " .
  • the ligand Yi is selected from the group consisting of: .
  • Yi is a bidentate chelating ligand having the formula: .
  • Y'i-Y"i represents a neutral, i.e., uncharged, chealting ligand.
  • Y'i-Y"i are capable of coordinating to a metal center.
  • ⁇ - ⁇ ' ⁇ ligand examples include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Yi and Y 2 are independently selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl and phosphine.
  • Yi and Y 2 may be extended by fusion, e.g., benzanulation. Additionally, Yi and Y 2 may be further substituted with alkyl, aryl, donor or acceptor groups.
  • Y ⁇ and Y 4 are independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteralkyl and heteroaryl.
  • Y 3 and Y 4 are joined to form a cycle, which may be extended by fusion, e.g., benzanulation.
  • Yi and Y 2 are the same.
  • Specific examples of ligands where Yi and Y 2 are the same include, but are not limited to, ligands selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • C* is a divalent carbon atom, n is 0, 1 , or 2.
  • m is 0, 1, or 2.
  • Y 1 and Y 2 are different.
  • Specific examples of ligands where Yi and Y 2 are different include, but are not limited to, ligands selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Yi is SO 3 Y " .
  • Specific examples of ligands Y; having the formula SO 3 Y " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Yi is CY 4 ⁇ .
  • CY 4 has the formula:
  • ligands Yi having the formula CY 4 " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Yi is SiY 4 ⁇ .
  • ligands Y; having the formula S1Y 4 " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Yi is OY 2 ⁇ .
  • OY 2 " has the formula:
  • ligands Yi having the formula OY 2 " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Y; is SY 2 ⁇ .
  • SY 2 " has the formula:
  • ligands Y having the formula S Y 2 ⁇ include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • the complex comprises two copper (I) centers.
  • complexes comprising two copper (I) centers include complexes selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • the carbene ligand is selected from the group consisting of:
  • each R includes a substituent independently selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, azacarbazole,
  • the carbene is . More preferably, the carbene is
  • R' i and R' 2 may represent mono, di, tri, or tetra substitutions.
  • R' i and R' 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • at least one of R' i and R' 2 is an alkyl having three or more carbon atoms.
  • the complex is selected from the group consisting of:
  • the complex is selected from the group consisting of:
  • Complex 3 Complex 4 ore preferably, the complex is:
  • the complex has the formula:
  • the complex is selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • the carbene ligand is bidentate.
  • the complex is selected from the group consisting of: .
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Z is a monodentate ligand.
  • the complex is included in a polymer.
  • the complex is included in the repeat unit of the polymer.
  • the complex is pendant on the polymer.
  • the polymer is selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • m is greater than 2.
  • n is 0-20.
  • the complex is included in a dendritic complex.
  • the dendritic complex is
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • m is greater than 1.
  • n is 0-20.
  • the complex is included in a small molecule.
  • a first device comprising an organic light emitting device further comprising an anode, a cathode; and an organic layer, disposed between the anode and the cathode.
  • the organic layer further comprising a phosphorescent complex itself comprising a three coordinate copper atom and a carbene ligand.
  • the first device is a consumer product.
  • the device may comprise a complex having Formula I, Formula II, Formula III, or Formula IV, as described above.
  • Selections for the substituents, ligands, and complexes described as preferred for the complexes having Formula I, Formula II, Formula III, or Formula IV are also preferred for use in a device that comprises a complex including a complex having Formula I, Formula II, Formula III, or Formula IV. These selections include those described for X ls X 2 , X'i, X' 2 ,
  • FIG. 1 shows an organic light emitting device.
  • FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
  • FIG. 3 shows complexes comprising a carbene ligand coordinated to a three coordinate copper atom.
  • FIG. 4 shows 1H-NMR spectrum of Complex 1.
  • FIG. 5 shows 1H-NMR spectrum of Complex 2.
  • FIG. 6 shows 1H-NMR spectrum of Complex 3.
  • FIG. 7 shows 1H-NMR spectrum of Complex 4.
  • FIG. 8 shows MALDI spectrum of Complex 1.
  • FIG. 9 shows MALDI spectrum of Complex 2.
  • FIG. 10 shows MALDI spectrum of Complex 3.
  • FIG. 11 shows MALDI spectrum of Complex 4.
  • FIG. 12 shows the absorption spectrum of Complex 1.
  • FIG. 13 shows the absorption spectrum of Complex 2.
  • FIG. 14 shows the absorption spectrum of Complex 3.
  • FIG. 15 shows the absorption spectrum of Complex 4.
  • FIG. 16A shows absorption spectrum of Complex 4
  • FIG. 16B shows the emission spectra of Complex 4.
  • FIG. 17A shows excitation and emission spectra of Complex 1
  • FIG. 17B shows excitation and emission spectra of Complex 2.
  • FIG. 18A shows excitation and emission spectra of Complex 3
  • FIG. 18B shows excitation and emission spectra of Complex 4.
  • FIG. 19A shows the x-ray structure of Complex 2
  • FIG. 19B shows the x-ray structure of Complex 4.
  • FIG. 20 shows the 31 P-NMR spectrum of Complex 1.
  • FIG 21. shows the ⁇ -NMR spectrum of Complex 5.
  • FIG. 22 shows the X-ray structure of Complex 5.
  • FIG. 23 shows LCMS spectrum of Complex 6.
  • FIG. 24A shows corrected emission and excitation spectra of Complex 5 in
  • FIG. 24B shows corrected emission and excitation spectra of Complex 6 in 2MeTHF at 77K.
  • FIG. 25 shows a corrected emission spectrum of Complex 4 in PMMA film at room temperature.
  • FIG. 26A shows a corrected emission spectrum of Complex 4 in CH 2 CI 2 at room temperature
  • FIG. 26B shows a corrected emission spectrum of Complex 2 in CH 2 CI 2 at room temperature.
  • FIG. 27 shows 1H-NMR spectrum of Complex 7.
  • FIG. 28A shows 1H-NMR spectrum of Complex 7
  • FIG. 28B shows the n B-NMR spectrum of Complex 7.
  • FIG. 29A shows excitation and emission spectra of Complex 7 in 2MeTHF at 77K
  • FIG. 29B shows excitation and emission spectra of Complex 8 in 2MeTHF at 77K.
  • FIG. 30A shows absorption spectrum of Complex 7
  • FIG. 30B shows the X-ray structure of Complex 7.
  • an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
  • the anode injects holes and the cathode injects electrons into the organic layer(s).
  • the injected holes and electrons each migrate toward the oppositely charged electrode.
  • an "exciton” which is a localized electron-hole pair having an excited energy state, is formed.
  • Light is emitted when the exciton relaxes via a photoemissive mechanism.
  • the exciton may be localized on an excimer or an exciplex. Non- radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
  • the initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
  • FIG. 1 shows an organic light emitting device 100.
  • Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160.
  • Cathode 160 is a complex cathode having a first conductive layer 162 and a second conductive layer 164.
  • Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in US 7,279,704 at cols. 6- 10, which are incorporated by reference.
  • each of these layers are available.
  • a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety.
  • An example of a p-doped hole transport layer is m- MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50: 1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
  • Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to
  • n- doped electron transport layer is BPhen doped with Li at a molar ratio of 1 : 1 , as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
  • FIG. 2 shows an inverted OLED 200.
  • the device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230.
  • Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200.
  • FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.
  • FIGS. 1 and 2 The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non- limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures.
  • the specific materials and structures described are exemplary in nature, and other materials and structures may be used.
  • Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers.
  • hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer.
  • an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.
  • OLEDs having a single organic layer may be used.
  • OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety.
  • the OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2.
  • the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al, which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent application Ser. No. 10/233,470, which is incorporated by reference in its entirety.
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
  • preferred methods include thermal evaporation.
  • Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. No
  • 6,294,398 and 6,468,819 which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used.
  • the materials to be deposited may be modified to make them compatible with a particular deposition method.
  • substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range.
  • Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize.
  • Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfmders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign.
  • PDAs personal digital assistants
  • Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C, and more preferably at room temperature (20-25 degrees C).
  • the materials and structures described herein may have applications in devices other than OLEDs.
  • other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
  • organic devices such as organic transistors, may employ the materials and structures.
  • halo halogen, alkyl, cycloalkyl, alkenyl, alkynyl, arylkyl, heterocyclic group, aryl, aromatic group, and heteroaryl are known to the art, and are defined in U.S. 7,279,704 at cols. 31-32, which are incorporated herein by reference.
  • the complexes include a monodentate or a bidentate carbene ligand coordinated to a three coordinate copper atom.
  • the complex can be either charged or neutral.
  • OLEDs organic light emitting diodes
  • the chelating anionic ligand is a high triplet energy ligand, capable of supporting metal-to-ligand charge transfer interactions.
  • the complexes in this class may provide high energy phosphorescence, which can be useful in the fabrication of doped OLEDs, in which the copper complex is an emissive dopant.
  • These materials may also be used as host materials to support an emissive dopant in an OLED structure.
  • a dipyridyl borate complex in this class of compounds has an emission maximum of 475 nm and a photoluminescence efficiency of 0.95 in the solid state. Suitable substitution of the pyridyl groups can red or blue shift this emission substantially.
  • the ability to tune emission energies may make these copper complexes excellent emitters and host materials for OLEDs. It is thought that the emission energy may be shifted high enough to make these compounds suitable host materials for deep blue to violet emissive dopants.
  • Phosphorescent OLEDs have relied largely on heavy metal complexes as emitters. In particular, devices often utilize emitters containing Ir or Pt to induce spin orbit coupling. Tetrahedral copper complexes have been reported, and are known to phosphoresce at room temperature. However, tetrahedral copper complexes may have certain limitations. In particular, flattening distortions may increase the non-radiative rate, which leads to a decrease in luminescence efficiency. Trigonal planar copper carbene complexes have now been found to give efficient phosphorescence at room temperature. We believe that this is the first observation of phosphorescence from trigonal planar copper complexes.
  • Trigonal planar copper complexes may also have several advantages for use in OLEDs.
  • the trigonal planar copper complexes have comparatively short lifetimes, in the tens of microsecond range (see Table 1).
  • Table 1 shows the lifetimes of several different trigonal planar copper carbene complexes.
  • the lifetime of the trigonal copper complex is longer than an Ir complex (i.e., 1-10 ⁇ ) but shorter than that of a platinum porphyrin complex.
  • Trigonal planar copper complexes may also be particularly useful in OLEDs used for certain applications.
  • copper complexes provide a broader line spectrum which is especially useful for lighting applications.
  • a device comprising a trigonal planar copper complex in combination with only one other complex may cover red, green, and blue colors.
  • a device comprising a trigonal planar copper complex and a blue emitter may cover all colors required for lighting.
  • Novel phosphorescent complexes are provided, the complexes comprising a carbene ligand coordinated to a three coordinate copper atom.
  • the carbene ligand has the formula:
  • *C is a divalent carbon atom coordinated to a monovalent copper atom Cu.
  • Xi and X 2 are substituents independently selected from alkyl, amine, phosphine, heteroalkyl, aryl and heteroaryl. Xi and X 2 may be further substituted, and Xi and X 2 are optionally linked to form a cycle.
  • the carbene ligand is monodentate.
  • each of Xi and X 2 independently forms a bond with *C.
  • a first bond is formed between *C and an atom ⁇ in substituent Xi
  • a second bond is formed between *C and an atom X' 2 in substituent X 2 .
  • ⁇ and X' 2 are independently selected from the group consisting of C, N, O, S and P.
  • the carbene ligand is monodentate.
  • Xi and X 2 are not joined to form a cycle. In another aspect, Xi and X 2 are joined to form a cycle.
  • the copper complex is neutral.
  • Neutral complexes may be
  • a neutral complex can be deposited via vapor deposition.
  • the copper complex is charged.
  • the complex has the formula:
  • Yi is independently selected from the group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl. Yi is a monodentate ligand or a bidentate ligand. n is 1 or 2. Preferably, n is 2.
  • the complex has the formula:
  • Yi and Y 2 are substituents that are independently selected from the group consisting of alkyl, heteroalkyl, aryl and heteroaryl. Yi and Y 2 may be further substituted. Yi and Y 2 are joined. Each of Yi and Y 2 form a bond with Cu. A first bond is formed between Cu and an atom ⁇ in substituent Y 1 and a second bond is formed between Cu and an atom Y' 2 in substituent Y 2 .
  • Y is selected from the group consisting of N, P, *C, O, and S.
  • Y' 2 is selected from the group consisting of N, P, *C, tetravalent carbon,
  • ⁇ is N.
  • the Cu atom, the ⁇ atom and the Y' 2 atom in the complex are included in a ring that can be, for example, a 4-membered, 5-membered, 6-membered, 7-membered, or 8- membered ring.
  • the ring comprising Cu, ⁇ and Y' 2 is a 5-membered or 6- membered ring.
  • Y 1 is selected from the group consisting of pyridyl, pyrazole, alkyl amine, imidazole, benzimidazole, triazole, tetrazole, pyridazine, pyrimidine, pyrazine, triazine, tetrazine, oxazole, thiazole, benzoxazole and benzothiazole.
  • Yi- Y 2 is selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Each ring is further substituted by a substituent selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • each R includes a substituent independently selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, azacarbazole, azadibenzofuran, and azadibenzothiophene.
  • Yi- Y 2 is selected from the group consisting of:
  • X is selected from the group consisting of NR, O, S, Se, CR 2 , and CO.
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Each ring is further substituted by a substituent selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • each R includes a substituent independently selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, azacarbazole, azadibenzofuran, and azadibenzothiophene.
  • Y is an unconjugated, monoanionic ligand containing BY 4 ⁇ , SO3Y “ , CY 4 " , Si0 4 " , OY 2 " , or SY 2 " .
  • Each Y is independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteralkyl and heteroaryl.
  • Y is BY 4 " .
  • the ligand Yi comprises two
  • the ligand Y has the formula:
  • the ligand Y that comprises two monodentate ligands, at least one of which is BY 4 " , is selected from the group consisting of:
  • Yi and Y 2 are independently selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxazolyl, thiszolyl, benzoxazolyl, benzothiazolyl and phosphine.
  • Yi and Y 2 may be extended by fusion, e.g., benzanulation. Additionally, Yi and Y 2 may be further substituted with alkyl, aryl, donor or acceptor groups.
  • Y 3 and Y 4 are independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteralkyl and heteroaryl. In one aspect, Y 3 and Y 4 are joined to form a cycle, may be extended by fusion, e.g., benzanulation.
  • Yi is a bidentate ligand having the formula BY 4 " .
  • the ligand Y is selected from the group consisting of:
  • Yi is a bidentate chelating ligand having the formula: .
  • Y'i-Y"i represents a neutral, i.e., uncharged, chelating ligand.
  • Y'i-Y"i are capable of coordinating to a metal center.
  • ⁇ - ⁇ ' ⁇ ligand examples include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Yi and Y 2 are independently selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxazolyl, thiszolyl, benzoxazolyl, benzothiazolyl and phosphine.
  • Yi and Y 2 may be extended by fusion, e.g., benzanulation. Additionally, Yi and Y 2 may be further substituted with alkyl, aryl, donor or acceptor groups.
  • Y 3 and Y 4 are independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteralkyl and heteroaryl. In one aspect, Y 3 and Y 4 are joined to form a cycle, which may be extended by fusion, e.g., benzanulation.
  • Yi and Y 2 are the same.
  • Specific examples of ligands where Yi and Y 2 are the same include, but are not limited to, ligands selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • C* is a divalent carbon atom, n is 0, 1, or 2.
  • m is 0, 1, or 2.
  • Y 1 and Y 2 are different.
  • Specific examples of ligands where Yi and Y 2 are different include, but are not limited to, ligands selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Yi is SO 3 Y " .
  • Specific examples of ligands Y; having the formula SO 3 Y " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Yi is CY 4 ⁇ .
  • CY 4 has the formula:
  • ligands Yi having the formula CY 4 " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Yi is SiY 4 ⁇ .
  • ligands Y; having the formula S1Y 4 " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Yi is OY 2 ⁇ .
  • OY 2 " has the formula:
  • ligands Yi having the formula OY 2 " include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Y 3 and Y 4 are selected from the group consisting of:
  • Y; is SY 2 ⁇ .
  • SY 2 " has the formula:
  • ligands Yi having the formula SY 2 ⁇ include, but are not limited to, ligands having the structure:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • the complex comprises two copper (I) centers.
  • complexes comprising two copper (I) centers include complexes selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • the carbene ligand is selected from the group consisting of:
  • the carbene is . More preferably, the carbene is
  • R' i and R' 2 may represent mono, di, tri, or tetra substitutions.
  • R' i and R' 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • at least one of R' i and R' 2 is an alkyl having three or more carbon atoms.
  • the complex is selected from the group consisting of:
  • the complex is selected from the group consisting of:
  • Complex 3 Complex 4 ore preferably, the complex is:
  • the complex has the formula:
  • the complex is selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • the carbene ligand is bidentate.
  • the complex is selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • Z is a monodentate ligand.
  • the complex is included in a polymer.
  • the complex is included in the repeat unit of the polymer.
  • the complex is pendant on the polymer.
  • the polymer is selected from the group consisting of:
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • m is greater than 2.
  • n is 0-20.
  • the complex is included in a dendritic complex.
  • the dendritic complex is
  • Each R is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, heteroalkyl, aryl and heteroaryl.
  • m is greater than 1.
  • n is 0-20.
  • the complex is included in a small molecule.
  • a first device comprising an organic light emitting device further comprising an anode, a cathode; and an organic layer, disposed between the anode and the cathode.
  • the organic layer further comprising a phosphorescent complex itself comprising a three coordinate copper atom and a carbene ligand.
  • the first device is a consumer product.
  • the device may comprise a complex having Formula I, Formula II, Formula III, or Formula IV, as described above.
  • Selections for the substituents, ligands, and complexes described as preferred for the complexes having Formula I, Formula II, Formula III, or Formula IV are also preferred for use in a device that comprises a complex including a complex having Formula I, Formula II, Formula III, or Formula IV. These selections include those described for X ls X 2 , X'i, X' 2 ,
  • Such devices may contain the trigonal copper complex as a neat thin film.
  • an OLED comprising a pure film of the complex may have a higher luminescent efficiency than an OLED that comprises the complex doped with another material.
  • the materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device.
  • emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present.
  • the materials described or referred to below are non-limiting examples of materials that may be useful in combination with the complexes disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

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EP2501707A4 (en) 2014-03-26
KR101822668B1 (ko) 2018-01-26
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US20140125221A1 (en) 2014-05-08
CN107793437B (zh) 2024-05-24
KR20120085917A (ko) 2012-08-01
JP6656858B2 (ja) 2020-03-04
EP2501707A1 (en) 2012-09-26
CN118561876A (zh) 2024-08-30
US8580394B2 (en) 2013-11-12
US9773986B2 (en) 2017-09-26
EP2501707B1 (en) 2017-08-02
JP2016040270A (ja) 2016-03-24
TW201134918A (en) 2011-10-16
CN107793437A (zh) 2018-03-13
CN102695711A (zh) 2012-09-26
TWI513796B (zh) 2015-12-21
IN2012DN05146A (https=) 2015-10-23
JP2013511532A (ja) 2013-04-04

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