WO2004006352A2 - Electronic devices made with electron transport and/or anti-quenching layers - Google Patents

Electronic devices made with electron transport and/or anti-quenching layers Download PDF

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Publication number
WO2004006352A2
WO2004006352A2 PCT/US2003/021617 US0321617W WO2004006352A2 WO 2004006352 A2 WO2004006352 A2 WO 2004006352A2 US 0321617 W US0321617 W US 0321617W WO 2004006352 A2 WO2004006352 A2 WO 2004006352A2
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English (en)
French (fr)
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WO2004006352A3 (en
Inventor
Daniel David Lecloux
Ying Wang
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to EP03763462A priority Critical patent/EP1520452A2/en
Priority to AU2003247964A priority patent/AU2003247964A1/en
Priority to JP2004520124A priority patent/JP2005533342A/ja
Priority to CA002492689A priority patent/CA2492689A1/en
Publication of WO2004006352A2 publication Critical patent/WO2004006352A2/en
Publication of WO2004006352A3 publication Critical patent/WO2004006352A3/en
Anticipated expiration legal-status Critical
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    • 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
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • Devices which use photoactive materials frequently include one or more charge transport layers, which are positioned between the photoactive (e.g., light-emitting) layer and one of the contact layers.
  • a hole transport layer may be positioned between the photoactive layer and the hole-injecting contact layer, also called the anode.
  • An electron transport layer may be positioned between the photoactive layer and the electron-injecting contact layer, also called the cathode.
  • organometallic compounds such as Ir and Pt complexes
  • a blocking layer inserted next to the luminescent layer on the cathode side can enhance the device efficiency.
  • US 6,097,147 claims a light emitting device comprising: a substantially transparent anode; a hole transporting layer over said anode; an emission layer over said hole transporting layer; a blocking layer over said emission layer; an electron transporting layer over said blocking layer; and a cathode in electrical contact with said electron transporting layer. It further claims a device wherein said blocking layer is characterized by a band gap greater than the energy level of excitons formed in said emission layer.
  • a photoactive layer positioned between said anode and said cathode, said photoactive layer comprising a cyclometallated complex of a transition metal, said cyclometalated complex having a LUMO energy level E2 and a HOMO energy level E4;
  • HOMO refers to the highest occupied molecular orbital of a compound.
  • LUMO refers to the lowest unoccupied molecular orbital of a compound.
  • group is intended to mean a part of a compound, such as a substituent in an organic compound. The prefix “hetero” indicates that one or more carbon atoms has been replaced with a different atom.
  • alkyl is intended to mean a group derived from an aliphatic hydrocarbon having one point of attachment, which group may be unsubstituted or substituted.
  • heteroalkyl is intended to mean a group derived from an aliphatic hydrocarbon having at least one heteroatom and having one point of attachment, which group may be unsubstituted or substituted.
  • alkylene is intended to mean a group derived from an aliphatic hydrocarbon and having two or more points of attachment.
  • heteroalkylene is intended to mean a group derived from an aliphatic hydrocarbon having at least one heteroatom and having two or more points of attachment.
  • alkenyl is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon double bonds and having one point of attachment, which group may be unsubstituted or substituted.
  • alkynyl is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon triple bonds and having one point of attachment, which group may be unsubstituted or substituted.
  • alkenylene is intended to mean a group derived from a hydrocarbon having one or more carbon-carbon double bonds and having two or more points of attachment, which group may be unsubstituted or substituted.
  • alkynylene is intended to mean a group derived from a hydrocarbon having one or more carbon- carbon triple bonds and having two or more points of attachment, which group may be unsubstituted or substituted.
  • heteroarylalkylene is intended to mean a group derived from an alkyl group having a heteroaryl substituent, which group may be further unsubstituted or substituted.
  • arylene is intended to mean a group derived from an aromatic hydrocarbon having two points of attachment, which group may be unsubstituted or substituted.
  • heteroarylene is intended to mean a group derived from an aromatic group having at least one heteroatom and having two points of attachment, which group may be unsubstituted or substituted.
  • arylenealkylene is intended to mean a group having both aryl and alkyl groups and having one point of attachment on an aryl group and one point of attachment on an alkyl group.
  • heteroarylenealkylene is intended to mean a group having both aryl and alkyl groups and having one point of attachment on an aryl group and one point of attachment on an alkyl group, and in which there is at least one heteroatom. Unless otherwise indicated, all groups can be unsubstituted or substituted.
  • adjacent to when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
  • adjacent R groups is used to refer to R groups that are next to each other in a chemical formula (i.e., R groups that are on atoms joined by a bond).
  • the term "compound” is intended to mean an electrically uncharged substance made up of molecules that further consist of atoms, wherein the atoms cannot be separated by physical means.
  • ligand is intended to mean a molecule, ion, or atom that is attached to the coordination sphere of a metallic ion.
  • complex when used as a noun, is intended to mean a compound having at least one metallic ion and at least one ligand.
  • the term “cyclometallated complex” is intended to mean a complex in which an organic ligand is bound to a metal in at least two positions to form a cyclic metal ligand structure, and in which at least one point of attachment is a metal-carbon bond.
  • the IUPAC numbering system is used throughout, where the groups from the Periodic Table are numbered from left to right as 1 through 18 (CRC Handbook of Chemistry and Physics, 81 st Edition, 2000).
  • Figure 4 shows Formula II for an electron transport composition.
  • Figure 5 shows Formulae ll(a) through ll(i) for an electron transport composition.
  • Figure 6 shows Formulae lll(a) and lll(b) for an electron transport composition.
  • Figure 7 shows Formulae IV(a) through IV(h) for a multidentate linking group.
  • Figure 18 is a plot of the LUMO of the iridium complex emitters vs the LUMO of ET/AQ compositions.
  • the photoactive layer 130 can be a light-emitting layer that is activated by an applied voltage (such as in a light-emitting diode or light-emitting electrochemical cell), a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
  • an applied voltage such as in a light-emitting diode or light-emitting electrochemical cell
  • a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage
  • Examples of photodetectors include photoconductive cells, photoresistors, photoswitches, phototransistors, and phototubes, and photovoltaic cells, as these terms are described in Markus, John, Electronics and Nucleonics Dictionary, 470 and 476 (McGraw-Hill, Inc. 1966).
  • a device within the scope of this invention shall mean a light-emitting diode, light-emitting electroluminescent device, or a photodete
  • the material has to be able to transport electrons efficiently, preferably with a mobility of > 10-7 cm 2 /(V*sec).
  • the energy difference between the LUMO of the ET/AQ material and the work function of the cathode has to be small enough to allow efficient electron injection from the cathode.
  • the energy barrier is preferred to be less than 1 V, that is , E-i-E 3 ⁇ 1 V
  • the LUMO level of ET/AQ has to be high enough to prevent it from receiving an electron from the photoactive layer. This usually requires E E 2 >-1V. Preferably, E E 2 >0.
  • Optimal energy level of ET/AQ in criteria 3 and 4 described above can be determined by the application of electron transfer theory.
  • the rate of electron transfer reaction as a function of the energy difference is described by the Marcus theory. (R. A. Marcus, P. Siders, J. Phys. Chem., 86, 622(1982). In its simplest form, it is written as
  • k is the rate constant
  • k ⁇ the Boltzman constant
  • T the temperature
  • E j and Ef are the energies of the initial and final states
  • ⁇ called the reorganization energy
  • the pre-factor v involves wave function overlap integrals, ⁇ , and is phenomenologically characterized as depending on the charge separation distance r via
  • the prefactor v 0 tends to be universally about 10 l o sec " ' .
  • hole transporting polymers are polyvinylcarbazole, (phenylmethyl)polysilane, and polyaniline and mixtures thereof. It is also possible to obtain hole transporting polymers by doping hole transporting molecules such as those mentioned above into polymers such as polystyrene and polycarbonate.
  • Examples of the photoactive layer 130 include all known electroluminescent materials. Organometallic electroluminescent compounds are preferred. The most preferred compounds include cyclometalated iridium and platinum electroluminescent compounds and mixtures thereof. Complexes of Iridium with phenylpyridine, phenylquinoline, or phenylpyrimidine ligands have been disclosed as electroluminescent compounds in Petrov et al., Published PCT Application WO 02/02714. Other organometallic complexes have been described in, for example, published applications US 2001/0019782, EP 1191612, WO 02/15645, and EP 1191614.
  • Electroluminescent devices with an active layer of polyvinyl carbazole (PVK) doped with metallic complexes of iridium have been described by Burrows and Thompson in published PCT applications WO 00/70655 and WO 01/41512.
  • Electroluminescent emissive layers comprising a charge carrying host material and a phosphorescent platinum complex have been described by Thompson et al., in U.S. Patent 6,303,238, Bradley et al., in Synth. Met. (2001 ), 116 (1- 3), 379-383, and Campbell et al., in Phys. Rev. B, Vol. 65 085210.
  • iridium complexes as have been Examples of a few suitable iridium complexes are given in Figure 3, as Formulae l(a) through l(e). Analogous tetradentate platinum complexes can also be used. These electroluminescent complexes can be used alone, or doped into charge-carrying hosts, as noted above.
  • One type of ET/AQ material is a phenanthroline derivative.
  • R1 and R2 are the same or different at each occurrence and are selected from H,
  • the phenanthroline derivative can have Formulae lll(a) or ll(b), shown in Figure 6, wherein: R1 , R2, a through d, n and x are as defined above;
  • the cathode 160 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
  • the cathode can be any metal or nonmetal having a lower work function than the anode.
  • Materials for the cathode can be selected from alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, including the rare earth elements and lanthanides, and the actinides. Materials such as aluminum, indium, calcium, barium, samarium and magnesium, as well as combinations, can be used.
  • Li-containing organometallic compounds, LiF, and Li 2 0 can also be deposited between the organic layer and the cathode layer to lower the operating voltage.
  • EXAMPLE 10 This example illustrates the preparation of Compound V(i) in Figure 9.
  • a mixture of 2,3-diaminotoluene (5.05 g, .041 mol) and phenanthrenequinone (7.84 g, ..038 mol) were refluxed in 112 ml chloroform for 29 hours.
  • the resultant solution was chromatographed down a silica column with chloroform eluant. Evaporated product from solvent to yield about 10 grams before vacuum oven drying. Material appeared crystalline
  • EXAMPLE 18 This example illustrates the preparation of an iridium electroluminescent complex, shown as Formula l(a) in Figure 3. Phenylpyridine li ⁇ and. 2-(4-fluorophenv0-5-trifluoromethylpyridine
  • Iridium complex l(c) was made using an analogous procedure.

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EP03763462A EP1520452A2 (en) 2002-07-10 2003-07-09 Electronic devices made with electron transport and/or anti-quenching layers
AU2003247964A AU2003247964A1 (en) 2002-07-10 2003-07-09 Electronic devices made with electron transport and/or anti-quenching layers
JP2004520124A JP2005533342A (ja) 2002-07-10 2003-07-09 電子輸送層および／またはアンチクエンチング層を用いて製造された電子デバイス
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PCT/US2003/021610 Ceased WO2004005288A2 (en) 2002-07-10 2003-07-09 Charge transport compositions comprising fluorinated phenanthroline derivatives
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