WO2013096918A1 - Polymères transporteurs de trous à base de triscarbazole réticulables - Google Patents

Polymères transporteurs de trous à base de triscarbazole réticulables Download PDF

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WO2013096918A1
WO2013096918A1 PCT/US2012/071506 US2012071506W WO2013096918A1 WO 2013096918 A1 WO2013096918 A1 WO 2013096918A1 US 2012071506 W US2012071506 W US 2012071506W WO 2013096918 A1 WO2013096918 A1 WO 2013096918A1
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group
optionally substituted
polymer
composition
subunits
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PCT/US2012/071506
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English (en)
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Carlos Zuniga
Seth Marder
Wojciech HASKE
Bernard Kippelen
Roland Martin
Jessem ABDALLAH
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Georgia Tech Research Corporation
Solvay Sa
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Publication of WO2013096918A1 publication Critical patent/WO2013096918A1/fr

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    • 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 radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/16—Halogens
    • C08F12/20—Fluorine
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/22—Oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/26—Nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • C08F212/26—Nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
    • 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 radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • 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
    • H10K85/341—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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
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    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • OLED organic light-emitting diodes
  • phosphorescent transition-metal-based emitters enabling emission from both singlet and triplet excited states, was first reported in 1995 and has since become common. Continuing progress in increasing the performance and development of OLED devices has commonly been the result of new material and new complex architectures employing a variety of multilayers with different functions including: hole and electron injection and transport; hole, electron, and exciton blocking; and acting as a host for phosphorescent emitters.
  • the highest efficiency devices in the prior art are generally those fabricated using high-vacuum vapor deposition.
  • This approach permits the fabrication of well-defined multilayers with relative ease.
  • vacuum-processing is time-consuming and expensive, while fabrication on large-area substrates can also be problematic.
  • solution-based approaches have the potential to facilitate rapid and low-cost processing and can be extended to large area substrates, and to high-throughput reel-to-reel processing.
  • higher molecular- weight materials that are difficult to be vapor-deposited, such as polymers or oligomers can show good morphological stability.
  • polymers that are highly processable in solution and capable of crosslinking by the application of heat and/or light. These polymers allow for solvent resistant and allow solution processing of subsequent layers while maintaining good hole transport abilities and device efficiencies.
  • Embodiments described herein include, for example, compositions, articles, devices, and methods for making.
  • composition comprising at least one polymer with crosslinking groups, said polymer comprising one or more type (I) subunits represented by formula (I) and optionally one or more type (II) subunits represented by formula (II):
  • X, Y, and Z are each independently H, alkyl, F or fluoroalkyl; XL is a crosslinking group; and TCz is an organic group comprising at least one optionally substituted triscarbazole group linked to a linker group, said triscarbazole group optionally comprises one or more crosslinking groups.
  • the TCz group is represented by formula (III) or formula (IV):
  • L is an linker group
  • Rl, R2, R3, and R4 are each independently a hydrogen, a halogen, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heteroalkyl group, or an optionally substituted heteroaryl group
  • XL, XLl, XL2, XL3, and XL4 are each independently a crosslinking group
  • kl, k2, k3, and k4 are each 0, 1 or 2.
  • composition comprising at least one polymer with crosslinking groups, said polymer comprising at least one type (I) subunit represented by formula (XII) or formula (XIII) and optionally at least one type (II) subunit represented by formula (XIV):
  • R16, R17, and R18 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroalkyl, optionally substituted heteroaryl, and crosslinking group; wherein XL is a crosslinking group; and wherein said crosslinking group comprises a reactive group optionally linked to a linker group selected from the group consisting of optionally substituted alkylene, optionally substituted arylene, optionally substituted heteroalkylene, and optionally substituted heteroarylene.
  • a hole transport layer comprising the composition discussed above, as well as an electroluminescence device comprising the hole transport layer.
  • the electroluminescence device can additionally comprise an anode, a hole injection layer, an emissive layer and a cathode.
  • the hole transport layer is solution deposited on the anode.
  • the polymer in the hole transport layer is thermally and/or photochemically crosslinked.
  • a hole injection layer is obtained by p-doping the crosslinked hole transport layer.
  • the emissive layer of the electroluminescence device comprises phosphorescent emitters, and the external quantum efficiency of the electroluminescence device at 1,000 cd/m is at least 5% or least 10%.
  • a method for making en electroluminescence device comprising: providing an anode layer; depositing the hole transport layer discussed above from solution onto the anode layer; and crosslinking the polymer to produce a crosslinked hole transport layer, wherein the crosslinked hole transport layer is substantially
  • the method further comprises depositing an emissive layer from solution onto the crosslinked hole transporting layer.
  • an electroluminescence device comprising: (i)providing a substrate; (ii) depositing the composition discussed above onto the substrate to form a layer; and (iii) rapidly heating said layer at a temperature of 150 °C or more for 60 minutes or less, wherein the polymer is crosslinked after said heating step.
  • the deposited layer is heated at a temperature of 200 °C or more.
  • the deposited layer is heated at a rate of 100 °C/minute or more.
  • the deposited layer is heated at a temperature of 150 °C or more for 40 minutes or less.
  • FIG. 1 shows schematically how crosslinking permits solution processing of multiplayer OLED devices.
  • the process can be used to fabricate either devices in which the active layers are entirely processed from solution, or hybrid devices containing both solution and vacuum-deposited layers.
  • Crosslinking can also improve morphological stability of OLED active layers, for example, by suppressing phase segregation or crystallization.
  • FIG. 2 shows three exemplary embodiments of the crosslinking triscarbazole hole transport polymer described herein.
  • FIG. 3 shows performance of OLED devices with spin-coated Polymer 5.38 hole transport layer and evaporation-deposited CBP:Ir(ppy)3 emitting layer.
  • FIG. 4 shows performance of an exemplary OLED device with spin-coated Polymer 5.38 hole transport layer and spin-coated PolymerA:PolymerB:Ir(pppy)3 emitting layer.
  • FIG. 5 shows temperature profile and performance of an exemplary OLED device with spin-coated Polymer 5.38 hole transport layer cured by rapid thermal processing and evaporation-deposited CBP:Ir(ppy)3 emitting layer.
  • FIG. 6 shows temperature profile and performance of an exemplary OLED device with spin-coated Polymer 5.38 hole transport layer cured by rapid thermal processing and spin-coated PolymerA:PolymerB:Ir(pppy)3 emitting layer.
  • FIG. 7 shows performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer and evaporation-deposited CBP:Ir(ppy)3 emitting layer.
  • FIG. 8 shows performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer and spin-coated PolymerA:PolymerB:Ir(pppy)3 emitting layer.
  • FIG. 9 shows temperature profile and performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer cured by rapid thermal processing and evaporation-deposited CBP:Ir(ppy)3 emitting layer.
  • FIG. 10 shows temperature profile and performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer cured by rapid thermal processing and PolymerA:PolymerB:Ir(pppy)3 spin-coated emitting layer.
  • FIG. 11 shows performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer and spin-coated Compound XI :Ir(pppy)3 emitting layer.
  • FIG. 12 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Xl :Ir(pppy)3 emitting layer.
  • FIG. 13 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound X2:Ir(pppy)3 emitting layer.
  • FIG. 14 shows performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer and spin-coated Compound X2:Ir(pppy)3 emitting layer.
  • FIG. 15 shows performance of an exemplary OLED device with spin-coated Polymer 5.40 hole transport layer and spin-coated Compound X3:Ir(pppy)3 emitting layer.
  • FIG. 16 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound X3:Ir(pppy)3 emitting layer.
  • FIG. 17 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Yl :Ir(pppy)3 emitting layer.
  • FIG. 18 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Y2:Ir(pppy)3 emitting layer.
  • FIG. 19 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Y3:Ir(pppy)3 emitting layer.
  • FIG. 20 shows performance of an exemplary OLED device with spin-coated
  • PEDOT:PSS hole injection layer spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Y4:Ir(pppy)3 emitting layer.
  • FIG. 21 shows performance of an exemplary OLED device with evaporation- deposited M0O 3 hole injection layer, spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Y4:Ir(pppy)3 emitting layer.
  • FIG. 22 shows performance of an exemplary OLED device with spin-coated
  • FIG. 23 shows performance of an exemplary OLED device with evaporation- deposited M0O 3 hole injection layer, spin-coated Polymer 5.40 hole transport layer and spin- coated Compound Y5:Ir(pppy)3 emitting layer.
  • Optionally substituted groups refers to, for example, functional groups that may be substituted or unsubstituted by additional functional groups.
  • groups that may be substituted or unsubstituted by additional functional groups.
  • groups name for example alkyl or aryl.
  • substituted alkyl or substituted aryl when a group is substituted with additional functional groups it may more generically be referred to as substituted alkyl or substituted aryl.
  • Alkyl refers to, for example, straight chain and branched alkyl groups having from 1 to 20 carbon atoms, or from 1 to 15 carbon atoms, or from 1 to 10, or from 1 to 5, or from 1 to 3 carbon atoms. This term is exemplified by groups such as for example methyl, ethyl, n- propyl, iso-propyl, n-butyl, t-butyl, n-pentyl, ethylhexyl, dodecyl, isopentyl, and the like.
  • Aryl refers to, for example, an aromatic carbocyclic group of from 6 to 14 carbon atoms having a single ring (e.g., phenyl) or multiple condensed rings (e.g., naphthyl or anthryl) which condensed rings may or may not be aromatic provided that the point of attachment is at an aromatic carbon atom.
  • Preferred aryls include phenyl, naphthyl, and the like.
  • Heteroalkyl refers to, for example, an alkyl group wherein one or more carbon atom is substituted with a heteroatom.
  • the heteroatom can be, for example, O, S, N, P, etc.
  • Heteroaryl refers to, for example, an aryl group wherein one or more carbon atom is substituted with a heteroatom.
  • the heteroatom can be, for example, O, S, N, P, etc.
  • One example of heteroaryl is carbazole.
  • Alkoxy refers to, for example, the group “alkyl-O-” which includes, by way of example, methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy, t-butyloxy, n-pentyloxy, 1-ethylhex-l-yloxy, dodecyloxy, isopentyloxy, and the like.
  • Aryloxy can refer, for example, to the group “aryl-O-” which includes, by way of example, phenoxy, naphthoxy, and the like.
  • Alkylene refers to, for example, straight chain and branched alkylene groups having from 1 to 20 carbon atoms, or from 1 to 15 carbon atoms, or from 1 to 10, or from 1 to 5, or from 1 to 3 carbon atoms. This term is exemplified by groups such as methylene, ethylene, n-propylene, z ' so-propylene, n-butylene, t-butylene, n-pentylene, ethylhexylene, dodecylene, isopentylene, and the like.
  • Arylene refers to, for example, an aromatic carbocyclic group of from 6 to 14 carbon atoms having a single ring (e.g., phenylene) or multiple condensed rings (e.g., naphthylene or anthrylene) which condensed rings may or may not be aromatic provided that the point of attachment is at an aromatic carbon atom.
  • Preferred arylenes include phenylene, naphthylene, and the like.
  • Heteroalkylene refers to, for example, an alkylene group wherein one or more carbon atom is substituted with a heteroatom.
  • the heteroatom can be, for example, O, S, N, P, etc.
  • Heteroarylene refers to, for example, an arylene group wherein one or more carbon atom is substituted with a heteroatom.
  • the heteroatom can be, for example, O, S, N, P, etc.
  • Olyalkylene refers to, for example, the group “-alkylene-O-”.
  • Oxyarylene refers to, for example, the group “-arylene-O-”.
  • Carbonyl alkylene refers to, for example, the group “-alkylene-C(O)-”.
  • Carbonyl arylene refers to, for example, the group “-arylene-C(O)-”.
  • Carboxyl alkylene refers to, for example, the group “-alkylene-C(0)-0-".
  • Carboxyl arylene refers to, for example, the group “-arylene-C(0)-0-”.
  • Ether refers to, for example, the group -alkylene-O-alkylene-, -arylene-O-alkylene-, -arylene-O-arylene-, wherein the alkylene and arylene can be optionally substituted.
  • “Ester” refers to, for example, the group -alkylene-C(0)-0-alkylene-, -arylene-C(O)- O-alkylene-, -arylene-C(0)-0-arylene-, wherein the alkylene and arylene can be optionally substituted.
  • Ketone refers to, for example, the group -alkylene-C(0)-alkylene-, -arylene-C(O)- alkylene-, -arylene-C(0)-arylene-, wherein the alkylene and arylene can be optionally substituted.
  • Triscarbazole refers to, for example, three or more carbazole groups connected to each other through aryl carbon-nitrogen bond and/or aryl carbon-carbon bond.
  • X, Y, and Z are each independently H, alkyl, F or fluoroalkyl; XL is a crosslinking group; TCz is an organic group comprising at least one optionally substituted triscarbazole group and an optional linker group; and wherein said triscarbazole group of the type (I) subunit optionally comprises one or more crosslinking groups.
  • Rl, R2, R3, R4, R5, R6, R7, R8, R9, RIO, Rl l, R12, R13, R14, R15, R16, R17, and R18 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroalkyl, optionally substituted heteroaryl, and crosslinking group;
  • XL is a crosslinking group
  • crosslinking group comprises a reactive group optionally linked to a linker group selected from the group consisting of optionally substituted alkylene, optionally substituted arylene, optionally substituted heteroalkylene, and optionally substituted heteroarylene.
  • the type (I) subunits are selected from one or several groups of
  • substituted alkyl group an optionally substituted aryl group, an optionally substituted heteroalkyl group, or an optionally substituted heteroaryl group.
  • the type (I) subunits may comprise one or more moieties from electron transporter, solubilizing groups, and compatibilizing groups.
  • the type (II) subunits may comprise one or more moieties from electron transporter, solubilizing groups, and compatibilizing groups.
  • the type (I) subunits do not comprise any 2-phenyl-5-phenyl- 1,3,4-oxadiazole moeity. In another embodiment, the type (I) subunits comprise no oxadiazole moeity.
  • the TZ group described herein comprises at least one optionally substituted triscarbazole group.
  • the TCz group can be represented by, for example, formula (III) or formula (IV):
  • L is an linker group
  • Rl, R2, R3, and R4 are each independently a hydrogen, a halogen, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heteroalkyl group, or an optionally substituted heteroaryl group
  • XL, XLl, XL2, XL3, and XL4 are each independently a crosslinking group
  • kl, k2, k3, and k4 are each 0, 1 or 2.
  • the TCz group can be represented by, for example, formula (V), formula (VI), formula (VII), or formula (VIII):
  • the TCz group does not comprise any crosslinking group, i.e., kl, k2, k3, and k4 are each 0. In other embodiments, the TCz group comprises at least one crosslinking group, i.e., at least one of kl, k2, k3, and k4 is not 0.
  • Rl, R2, R3, and R4 are each a hydrogen. In other embodiments, at least one of Rl, R2, R3, and R4 comprises an optionally substituted carbazole group. In further embodiments, Rl, R2, R3, and R4 each comprises an optionally substituted carbazole group.
  • Crosslinking groups are known in the art and described in, for example, Zunga et ah, Chem. Mater., 23:658-681 (2011), which is incorporated herein by reference in its entirety.
  • the crosslinking group can be, for example, a reactive group optionally linked to a linker group.
  • Reactive groups are known in the art. Any reactive groups that are crosslinking by heat, light, chemical treatment or a combination thereof are within the scope of this application.
  • the reactive group can be, for example, styrenic, acrylate, oxetane, cinnamate, chalcone, trifluorovinylether (TFVE), benzocyclobutane, silane, etc.
  • Examples of the reactive group include the following:
  • R' can be, for example, a hydrogen, a halogen, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heteroalkyl group, or an optionally substituted heteroaryl group
  • R" is a hydrogen, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heteroalkyl group, or an optionally substituted heteroaryl group.
  • Linker groups are known in the art and described in, for example, WO 2010149618, WO 2010149620, and WO 2010149622, all of which are incorporated herein by reference in their entireties.
  • the linker group can be, for example, an optionally substituted alkylene group, an optionally substituted arylene group, an optionally substituted heteroalkylene group, or an optionally substituted heteroaryl ene group.
  • the linker group can be, for example, an alkylene group, an oxyalkylene group, an oligo-alkylene group, an oxyarylene group, a carbonyl alkylene group, a carbonyl arylene group, a carboxyl alkylene group, a carboxyl arylene group, an ether group, an ester group, or a ketone group.
  • the linker group is resistant to oxidative, reductive, or thermal destruction under normal operating conditions of OLED devices.
  • the linker group does not comprise any 2-phenyl-5-phenyl- 1,3,4-oxadiazole group. In other embodiments, the linker group comprise no oxadiazole group.
  • Polymers described herein are solution-processable and capable of crosslinking, and possess good hole transport ability.
  • the weight average molecular weight (Mw) of the polymer can be, for example, 5,000 Da or more, 10,000 Da or more, 15,000 Da or more, or 20,000 Da or more.
  • the polymer can comprise, for example, 3 or more crosslinking groups per macromolecule, or 5 or more crosslinking groups per macromolecule, or 10 or more crosslinking groups per macromolecule.
  • the polymer can be a homopolymer. In such homopolymer, the type (II) subunits are absent, and the type (I) subunits each comprises at least one crosslinking group.
  • the polymer can be a copolymer of the type (I) subunits and the type (II) subunits.
  • the copolymer can be, for example, a block copolymer, an alternating copolymer, or a random copolymer.
  • the type (I) subunits may or may not comprise a crosslinking group.
  • the molar fraction of the type (I) subunits can be, for example, between about 0.5 to about 0.99.
  • the molar fraction of the type (I) subunits can be, for example, between about 0.7 to about 0.9.
  • the molar fraction of the type (I) subunits and the type (II) subunits can be varied to modify polymer properties such as conductivity, mechanical strength, solvent resistance, etc.
  • the polymer can also be a copolymer that further comprises one or more type (III) subunits.
  • the type (II) subunits may or may not be present. If the type (II) subunits are absent, then the type (I) subunits must comprise at least one crosslinking group.
  • the type (III) subunits can comprise one or more moieties selected from the group consisting of electron transporters, solubilizing groups,
  • the type (III) subunits can comprise at least one crosslinking group comprising at least one reactive group having similar reactivity to the reactive groups of the type (II) subunits.
  • the polymer does not comprise any 2-phenyl-5 -phenyl- 1,3,4- oxadiazole group. In other embodiments, the polymer comprises no oxadiazole group.
  • polystyrene resin examples include the following:
  • the type (I) subunits do not comprise any crosslinking groups, and the type (I) subunits and the type (II) subunits are arranged as a block copolymer.
  • This architecture enables separated phases, including a non-crosslinked (continuous) phase concentrating the triscarbazole groups (optimizing hole transport) chemically connected to a (dispersed) phase which concentrates the crosslinking groups, with possible tuning to allow for high mobility (low Tg) of the reacting groups.
  • Methods for producing styrenic block copolymers are known in the art.
  • Polymers described herein can be unexpectedly effective as hole transport material, and can be used to make highly efficient and stable OLED devices. Moreover, polymers described herein can have unexpectedly superior physical properties, such as high solubility and processability, and/or high resistance to crystallization and/or thermal degradation during OLED operation.
  • polymers described herein can be readily soluble in common organic solvents. These polymers can be readily processed to form compositions useful in organic electronic devices, especially in the hole transport layer of OLED devices.
  • the hole transport layer can comprise, for example, the solution-processable crosslinking polymer described herein.
  • the hole transport layer can further comprise, for example, a different crosslinking material.
  • the hole transport layer can be fabricated from a solution comprising the solution- processable crosslinking polymer described herein.
  • the solution can further comprise, for example, an organic solvent such as chlorobenzene, a photoacid generator such as PAG: 4- ((2-Hydroxytetradecyl)oxy)-phenyl)phenyliodonium hexafluoroantimonate, and/or a thermoacid generator such as TAG: 4-isopropyl-4'-methyldiphenyl iodonium
  • the solution can comprise, for example, between 0.1-50 wt.% of the polymer, or between 0.2-25 wt.% of the polymer, or between 0.5-10 wt.% of the polymer, or between 1-5 wt.% of the polymer.
  • the hole transport layer can be fabricated by methods known in the art, such as spin coating from solution. If the hole transport layer is a film deposited from a solution, following solution processing, the film can be dried on a hotplate and subjected to crosslinking. The film can be crosslinked by heating at a temperature of, for example, 100- 200 °C, or 150-250 °C, or 200-300 °C, or 250-350 °C, or 300-400 °C. The film can also be crosslinked photochemically by, for example, UV.
  • a hole injection layer can be formed from the solution-processable crosslinking polymer described herein modified by soluble molecular p-dopants known in the prior art.
  • useful dopants are dithiol complexes of Cr(VI) and Mo(VI) described in Qi et al, J. Am. Chem. Soc. 131 : 12530-12531 (2009), incorporated herein by reference in its entirely. Other examples are described in WO 2008/061517, incorporated herein by reference in its entirety.
  • Electroluminescence devices such as OLED are well known in the art.
  • the electroluminescence device can comprise at least an anode, a cathode, an emissive layer, and a hole transport layer comprising the solution-processable crosslinking polymer described herein.
  • the electroluminescence device may also comprise en electron transport layer.
  • ITO inert and transparent substrate
  • cathode in electroluminescence devices include, for example, a combination of LiF as electron injecting material coated with a vacuum deposited layer of Al.
  • Suitable materials for electron transport layer in electroluminescence devices include, for example, 2,9-Dimethyl-4,7-diphenyl-l,10- phenanthroline (BCP) and 3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-l,2,4-triazole (TAZ), as well as those described in WO 2009080796 and WO 2009080797, both of which are incorporated herein by reference in their entireties.
  • BCP 2,9-Dimethyl-4,7-diphenyl-l,10- phenanthroline
  • TEZ 3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-l,2,4-triazole
  • Host materials for the emissive layer include, for example, 4,4'-Bis(carbazol-9- yl)biphenyl (CBP) and ambipolar materials described in WO 2010149618, WO 2010149620, and WO 2010149622, all of which are incorporated herein by reference in their entireties.
  • CBP 4,4'-Bis(carbazol-9- yl)biphenyl
  • Guest materials for the emissive layer include, for example, Iridium complexes such as Tris(2-phenylpyridine)iridium(III) (Ir(ppy) 3 ), Tris(5 -phenyl- 10,10-dimethyl-4-aza- tricycloundeca-2,4,6-triene)Iridium(III) (Ir(pppy) 3 ) and Bis(3,5-difiuoro-2-(2-pyridyl)phenyl- (2-carboxypyridyl)iridium (III) (Flr(pic)), as well as Platinum complexes such as
  • the hole transport layer can be deposited on the anode from a solution.
  • the hole transport layer can be formed from solution on a hole injection layer.
  • the emissive layer can be deposited on the hole transport layer from a solution.
  • the emissive layer can be vacuum vapor deposited on the hole transport layer.
  • the electroluminescence device can comprise a crosslinked hole transport layer, wherein the polymer in the hole transport layer can be, for example, thermally crosslinked or photochemically crosslinked.
  • the crosslinking of the polymer of the hole transport layer can result in, for example, an insoluble organic layer resistant to degradation by solution processing of a subsequent layer from solution.
  • the electroluminescence device comprises an emissive layer that comprises Ir(ppy) 3 .
  • the external quantum efficiency of such electroluminescence device at 1,000 cd/m can be, for example, at least 5%, or at least 8%, or at least 10%, or at least 12%, or at least 15%, or at least 18%, or at least 20%.
  • RTP enables the fast curing of films.
  • a film of the solution- processable crosslinking polymer described herein is solution deposited, said film can be heated at a temperature of 150 °C or more for 60 minutes or less, wherein the crosslinking polymer is crosslinked during the heating step.
  • the RTP heating step can comprise, for example, heating the film at a temperature of 150 °C or more, or 200 °C or more, or 250 °C or more, or 300 °C or more, or 350 °C or more, or 400 °C or more.
  • the RTP heating step can comprise, for example, ramping the temperature at a rate of 50 °C/minute or more, or 100 °C/minute or more, or 150 °C/minute or more, or 200 °C/minute or more, or 250 °C/minute or more. Further, the film can be cured by RTP at a temperature of 150 °C or more for, for example, 60 minutes or less, or 50 minutes or less, or 40 minutes or less, or 30 minutes or less, or 20 minutes or less.
  • RTP includes, for example, increasing throughput and minimizing the time that the material is subjected to high temperature.
  • RTP has been described in, for example, Hisashi Fukuda, Rapid Thermal Processing for Future Semiconductor Devices 1-9 (2003).
  • RTP allowed the films to be cured in only a few minutes.
  • films cured via the RTP process may only require about 10 minutes of heating time. Even when both the ambient purge and the cooling steps are taken into account, the total processing time for the process may be under 20 minutes, which is much faster than the four- hour hotplate bakes done previously.
  • the RTP cured films have adequate solvent resistance to withstand typical spin coating conditions of upper layers ⁇ e.g., layers deposited directly on top of the RTP processed layer) of organic electronic devices.
  • the RTP process includes the following steps: 1) the polymer was spun-coated and dried on 90 °C hotplate for 5 min; 2) the RTP sample area was purged with N 2 for 3 min; 3) the temperature was ramped at 150 °C/min for 1.57 min; 4) the temperature was ramped at 50 °C/min. for 0.87 min; 5) the sample was maintained at 300 °C for 5 min; and 6) the sample was cooled from 300 °C to 180 °C for 2.25 min and from 180 °C to 100 °C for 9 min.
  • the total processing time in said embodiment is 19.43 minutes.
  • a polystyrene polymer is provided with a multicarbazole pendant group like structure I, wherein P is the polymer backbone and R can be other carbazole units, and the polymer also has thermally crosslinking groups.
  • the crosslinking groups may be attached to one or more of the carbazoles of the multicarbazole pendant group or may be attached to another subunit of the polymer backbone.
  • Each carbazole ring can be further substituted with halogens, alkyl, heteroalkyl groups (e.g., functional groups), aryl, or heteroaryl groups. Examples include a "triscarbazole” such as structure II or a "heptakiscarbazole” such as such as structure III.
  • the multicarbazole pendant groups can sometimes be referred to as "dendrimers," where, for example, structure II would be a second generation dendrimer and structure III would be a third generation dendrimer.
  • Each carbazole substituent may be substituted in the ortho, either meta, and/or para position relative to the nitrogen of the parent carbazole.
  • Each dendrimer generation maybe have different ortho, meta, and/or para substitutions relative to the nitrogens of their parent compared to the substitution pattern of carbazoles in previous generations (e.g., the second generation carbazoles are substituted para to the first carbazole 's nitrogen and the third generation's carbazoles are substituted meta to the second generation's nitrogens).
  • the ratio of multicarbazole pendant groups to crosslinking groups can be varied in the polymer to effect properties such as hole transport ability, processibility, mechanical stability, rate of crosslinking, etc.
  • the polystyrene may also contain other groups such as electron
  • the styrene polymers may also be a copolymer with other backbone subunits.
  • Triscarbazole monomer (6-(9H-carbazol-9-yl)-9-(4-vinylbenzyl)-9H-3,9'-bicarbazole):
  • Poly(triscarbazole) Polymer A, Poly(6-(9H-carbazol-9-yl)-9-(4-vinylbenzyl)-9H-3,9'- bicarbazole): A Schlenk flask was charged with tris-carbazole monomer 6-(9H-carbazol-9- yl)-9-(4-vinylbenzyl)-9H-3,9'-bicarbazole (1.0 g, 1.6 mmol), AIBN (7.0 mg, 0.042 mmol) and dry THF (20.0 ml). The polymerization mixture was purged with nitrogen (removal of oxygen), securely sealed under nitrogen, and heated to 60°C.
  • the polymerization was carried out at 60°C with stirring for 7 days. After cooling to room temperature, the polymer was precipitated with acetone. The white polymer precipitate was collected by filtration, dissolved in dichloromethane, and precipitated with acetone again. This dissolution/precipitation procedure was repeated three more times. The collected polymer was dried under vacuum. After vacuum dry, the polymer as white solid in 0.93 g (93.0 %) was obtained.
  • ITO substrates Indium tin oxide (ITO)-coated glass slides (Colorado Concept Coatings LLC) with a sheet resistivity of -15 ⁇ /sq were used as substrates for the OLEDs fabrication.
  • the ITO substrates were masked with kapton tape and the exposed ITO was etched in acid vapor (1 :3 by volume, HNO 3 : HC1) for 5 min at 60 °C.
  • the substrates were cleaned in an ultrasonic bath in the following solutions: detergent water, distilled water, acetone, and isopropanol for 20 min in each step. At the end the substrates were blown dry with nitrogen. Subsequently, ITO substrates were 0 2 plasma treated for 2 min.
  • Polymer 5.38 was processed in the glove box under nitrogen. 10 mg of Polymer 5.38 was dissolved in 1ml of anhydrous chlorobenzene (Aldrich). 35 nm thick films of the hole- transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing at 300 °C for 10 min. A watch glass was used during the curing process over the samples in order to avoid excessive heat loses.
  • anhydrous chlorobenzene Aldrich
  • Emissive layer consisting of a host - CBP (Aldrich) and an emitter - Ir(ppy)3 (Lumtec) was deposited by co-evaporation of the two components at 0.94 A/s and 0.06 A/s respectively.
  • the electron transport layer, BCP (Aldrich), the electron-injection layer, LiF (Aldrich),aluminum and silver were thermally evaporated at 1 A/s, 0.2 A/s, 2 A/s and 2 A/s respectively.
  • the pressure in the vacuum chamber was l x lO "7 Torr.
  • the active area of the tested devices was about 0.1 cm . The devices were tested in a glove box under nitrogen.
  • OLED devices with Polymer 5.38 spin-coated as the hole transport layer, as well as evaporation-deposited CBP: Ir(ppy)3 emitting layer, are capable of achieving high external quantum efficiencies.
  • ITO substrates Indium tin oxide (ITO)-coated glass slides (Colorado Concept Coatings LLC) with a sheet resistivity of -15 ⁇ /sq were used as substrates for the OLEDs fabrication.
  • the ITO substrates were masked with kapton tape and the exposed ITO was etched in acid vapor (1 :3 by volume, HNO3: HC1) for 5 min at 60 °C.
  • the substrates were cleaned in an ultrasonic bath in the following solutions: detergent water, distilled water, acetone, and isopropanol for 20 min in each step. At the end the substrates were blown dry with nitrogen. Subsequently, ITO substrates were 0 2 plasma treated for 2 min.
  • Polymer 5.38 was processed in the glove box under nitrogen. 10 mg of Polymer 5.38 was dissolved in 1ml of anhydrous chlorobenzene (Aldrich). 35 nm thick films of the hole- transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing at 300 °C for 10 min. A watch glass was used during the curing process over the samples in order to avoid excessive heat loses.
  • anhydrous chlorobenzene Aldrich
  • Emissive layer consisting of a polymer blend and emitter was prepared in the following way in the glove box: 10 mg of Polymer A in 1 ml chlorobenzene, 10 mg of Polymer B in 1 ml of chlorobenzene and 10 mg of Ir(pppy) 3 (Solvay) in 1 ml of chlorobenzne.
  • the solutions of the polymers were then mixed together (1ml of each) to which 128 ⁇ of Ir(pppy) 3 was added.
  • the mixture was spin-coated at 2000 rpm, 1000 rpm / sec, 60 sec and dried on hot plate at 120 °C for 10-15 min.
  • the electron transport layer, BCP (Aldrich), the electron-injection layer, LiF (Aldrich), aluminum and silver were thermally evaporated at 1 A/s, 0.2 A/s, 2 A/s and 2 A/s respectively.
  • the pressure in the vacuum chamber was l x lO "7 Torr.
  • OLED devices with Polymer 5.38 spin-coated as the hole transport layer, as well as spinning-coated emitting layer, are capable of achieving high external quantum efficiencies.
  • devices having hole transport layers comprising the crosslinking hole transport polymers with triscarbazole pendant groups are suitable as HTLs for solution processing of subsequent layers.
  • various polymers can be suitable in different device architectures and/or with different materials in the other devices layers to modify the balance of charge and increase efficiency.
  • ITO substrates Indium tin oxide (ITO)-coated glass slides (Colorado Concept Coatings LLC) with a sheet resistivity of -15 ⁇ /sq were used as substrates for the OLEDs fabrication.
  • the ITO substrates were masked with kapton tape and the exposed ITO was etched in acid vapor (1 :3 by volume, HNO 3 : HC1) for 5 min at 60 °C.
  • the substrates were cleaned in an ultrasonic bath in the following solutions: detergent water, distilled water, acetone, and isopropanol for 20 min in each step. At the end the substrates were blown dry with nitrogen. Subsequently, ITO substrates were 0 2 plasma treated for 2 min.
  • Polymer 5.38 was processed in the glove box under nitrogen. 10 mg of Polymer 5.38 was dissolved in 1ml of anhydrous chlorobenzene (Aldrich). 35 nm thick films of the hole- transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing by RTP at 300 °C for 5 min. The RTP procedure temperature profile is presented in Figure 5(A).
  • Emissive layer consisting of a host - CBP (Aldrich) and an emitter - Ir(ppy)3 (Lumtec) was deposited by co -evaporation of the two components at 0.94 A/s and 0.06 A/s respectively.
  • the electron transport layer, BCP (Aldrich), the electron-injection layer, LiF (Aldrich), aluminum and silver were thermally evaporated at 1 A/s, 0.2 A/s, 2 A/s and 2 A/s respectively.
  • the pressure in the vacuum chamber was 1 x 10 "7 Torr.
  • the active area of the tested devices was about 0.1 cm .
  • the devices were tested in a glove box under nitrogen. The performance of the device is shown in Figure 5(B)-(C).
  • ITO substrates Indium tin oxide (ITO)-coated glass slides (Colorado Concept Coatings LLC) with a sheet resistivity of -15 ⁇ /sq were used as substrates for the OLEDs fabrication.
  • the ITO substrates were masked with kapton tape and the exposed ITO was etched in acid vapor (1 :3 by volume, HNO3: HC1) for 5 min at 60 °C.
  • the substrates were cleaned in an ultrasonic bath in the following solutions: detergent water, distilled water, acetone, and isopropanol for 20 min in each step. At the end the substrates were blown dry with nitrogen. Subsequently, ITO substrates were 0 2 plasma treated for 2 min.
  • Polymer 5.38 was processed in the glove box under nitrogen. 10 mg of Polymer 5.38 was dissolved in 1ml of anhydrous chlorobenzene (Aldrich). 35 nm thick films of the hole- transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing by RTP at 300 °C for 5 min. The RTP procedure temperature profile is presented in Figure 6(A).
  • Emissive layer consisting of a polymer blend and emitter was prepared in the following way in the glove box: 10 mg of Polymer A in 1 ml chlorobenzene, 10 mg of Polymer B in 1 ml of chlorobenzene and 10 mg of Ir(pppy) 3 (Solvay) in 1 ml of
  • the electron transport layer BCP (Aldrich)
  • the electron-injection layer LiF
  • a device is fabricated in substantially the same way as in Example 2, except that the hole transport layer comprises Polymer 5.40 instead of Polymer 5.38.
  • the performance of the device is shown in Figure 7.
  • Polymer 5.40 was processed in the glove box under nitrogen. 5 mg of TAG (4- isopropyl-4'-methyldiphenyl iodonium tetrakis(pentafluorophenyl)borate) (DPI-TPFPB) (Aldrich) was dissolve in 10 ml of anhydrous chlorobenzene (Aldrich) then 10 mg of Polymer 5.40 was dissolved in 1ml of previously prepared TAG solution. Around 35 nm thick films of the hole-transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing at 200 °C for 30 min. A watch glass was used during the curing process over the samples in order to avoid excessive heat loses.
  • TAG 4- isopropyl-4'-methyldiphenyl iodonium tetrakis(pentafluorophenyl)borate
  • LiF/AI/Ag (2.5/60 nm/100 nm)
  • a device is fabricated in substantially the same way as in Example 3, except that the hole transport layer comprises Polymer 5.40 instead of Polymer 5.38.
  • the performance of the device is shown in Figure 8.
  • Polymer 5.40 was processed in the glove box under nitrogen. 5 mg of TAG (DPI- TPFPB) (Aldrich) was dissolve in 10 ml of anhydrous chlorobenzene (Aldrich) then 10 mg of Polymer 5.40 was dissolved in 1ml of previously prepared TAG solution. Around 35 nm thick films of the hole-transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing at 200 °C for 30 min. A watch glass was used during the curing process over the samples in order to avoid excessive heat loses.
  • TAG DPI- TPFPB
  • Aldrich anhydrous chlorobenzene
  • a device is fabricated in substantially the same way as in Example 4, except that the hole transport layer comprises Polymer 5.40 instead of Polymer 5.38.
  • the performance of the device is shown in Figure 9(B)-(C).
  • Polymer 5.40 was processed in the glove box under nitrogen. 5 mg of TAG (DPI- TPFPB) (Aldrich) was dissolved in 10 ml of anhydrous chlorobenzene (Aldrich) then 10 mg of Polymer 5.40 was dissolved in 1 ml of previously prepared TAG solution. Around 35 nm thick films of the hole-transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing by RTP at 200 °C for 30 min. The RTP procedure temperature profile is presented in Figure 9(A).
  • a device is fabricated in substantially the same way as in Example 5, except that the hole transport layer comprises Polymer 5.40 instead of Polymer 5.38.
  • the performance of the device is shown in Figure 10(B)-(C).
  • Polymer 5.40 was processed in the glove box under nitrogen. 5 mg of TAG (DPI- TPFPB) (Aldrich) was dissolve in 10 ml of anhydrous chlorobenzene (Aldrich) then 10 mg of Polymer 5.40 was dissolved in 1 ml of previously prepared TAG solution. Around 35 nm thick films of the hole-transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 30 minutes followed by thermal curing by RTP at 200 °C for 30 min. The RTP procedure temperature profile is presented in Figure 10(A).
  • TAG DPI- TPFPB
  • Aldrich anhydrous chlorobenzene
  • Polymer 5.40 was dissolved in 1 ml of previously prepared TAG solution. Around 35 nm thick films of the hole-transport material were spin-coated at 1000 rpm, acceleration 1540 rpm/sec for 60 sec. The films were then dried on a hot plate at 110
  • a device is fabricated in substantially the same way as in Example 7, except that the emissive layer host comprises Compound XI instead of Polymer A:Polymer B blend.
  • the performance of the device is shown in Figure 11.
  • Emissive layer consisting of the Compound XI host and emitter was prepared in the following way in the glove box: 10 mg of Compound XI was dissolved in 1 ml
  • G ass A device is fabricated in substantially the same way as in Example 10, except that a PEDOT:PSS hole injection layer was deposited between the ITO substrate and the Polymer 5.40 hole transport layer. The performance of the device is shown in Figure 12.
  • PEDOT:PSS AI4083 (Clevios) was spin-coated at 5000 rpm, acceleration - 928 rpm/s for 60 sec. Subsequently, the films were heated on a hot plate at 140°C for 15 min. PEDOT:PSS was deposited in air.
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound X2 instead of Compound XI .
  • the performance of the device is shown in Figure 13.
  • LiF/AI/Ag (2.5/60 nm/100 nm)
  • a device is fabricated in substantially the same way as in Example 10, except that the emissive layer host comprises Compound X2 instead of Compound XI .
  • the performance of the device is shown in Figure 14.
  • a device is fabricated in substantially the same way as in Example 10, except that the emissive layer host comprises Compound X3 instead of Compound XI .
  • the performance of the device is shown in Figure 15.
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound X3 instead of Compound XI .
  • the performance of the device is shown in Figure 16.
  • LiF/Al/Ag (2.5/60 nm/100 nm)
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound Yl instead of Compound XI .
  • the performance of the device is shown in Figure 17.
  • Emissive layer consisting of the Compound Yl host and emitter was prepared in the following way in the glove box: 10 mg of Compound Yl was dissolved in 1 ml
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound Y2 instead of Compound XI .
  • the performance of the device is shown in Figure 18.
  • Emissive layer consisting of the Compound Y2 host and emitter was prepared in the following way in the glove box: 10 mg of Compound Y2 was dissolved in 1.5 ml toluene and 10 mg of Ir(pppy) 3 (Solvay) in 1.0 ml of toluene. 60 ⁇ of Ir(pppy) 3 was added to 1 ml of the solution of Compound Y2. The solution was then spin-coated onto the HTL at 2000 rpm, 1000 rpm / sec, 60 sec. The films were dried at 100 °C for 5 minutes.
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound Y3 instead of Compound XI .
  • the performance of the device is shown in Figure 19.
  • Emissive layer, consisting of the Compound Y3 host and emitter was prepared in the following way in the glove box: 10 mg of Compound Y3 was dissolved in a mixture of 1 ml chlorobenzene and 1 ml of DMF, 10 mg of Ir(pppy) 3 (Solvay) was dissolved in 1 ml of chlorobenzne. 64 ⁇ of Ir(pppy) 3 was added to 1 ml of the solution of Compound Y3. The solution was then spin-coated onto the HTL at 2000 rpm, 3000 rpm / sec, 60 sec. The films were dried at 100 °C for 5 minutes.
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound Y4 instead of Compound XI .
  • the performance of the device is shown in Figure 20.
  • Emissive layer consisting of the Compound Y4 host and emitter was prepared in the following way in the glove box: 10 mg of Compound Y4 was dissolved in mixture of 1 ml toluene and 0.5 ml of acetonitrile, and 10 mg of Ir(pppy) 3 (Solvay) in 1 ml of toluene. 60 ⁇ of Ir(pppy) 3 was added to 1 ml of the solution of Compound Y4. The solution was then spin- coated onto the HTL at 2000 rpm, 1000 rpm / sec, 60 sec. The films were dried at 100 °C for 5 minutes.
  • a device is fabricated in substantially the same way as in Example 19, except that the hole injection layer host comprises M0O3 instead of PEDOT:PSS.
  • the hole injection layer, M0O3 (Aldrich) was thermally evaporated at 0.2 A/s.
  • the pressure in the vacuum chamber was 1 x 10 "7 Torr.
  • the performance of the device is shown in Figure 21.
  • a device is fabricated in substantially the same way as in Example 11 , except that the emissive layer host comprises Compound Y5 instead of Compound XI .
  • the performance of the device is shown in Figure 22.
  • Emissive layer consisting of the Compound Y5 host and emitter was prepared in the following way in the glove box: 10 mg of Compound Y5 was dissolved in 1.5 ml toluene and 10 mg of Ir(pppy) 3 (Solvay) in 1.0 ml of toluene. 60 ⁇ of Ir(pppy) 3 was added to 1 ml of the solution of Compound Y5. The solution was then spin-coated onto the HTL at 2000 rpm, 1000 rpm / sec, 60 sec. The films were dried at 100 °C for 5 minutes.
  • Example 22 Example 22
  • a device is fabricated in substantially the same way as in Example 21, except that the hole injection layer host comprises M0O 3 instead of PEDOT:PSS.
  • the hole injection layer, M0O 3 (Aldrich), was thermally evaporated at 0.2 A/s.
  • the pressure in the vacuum chamber was 1 x 10 "7 Torr.
  • the performance of the device is shown in Figure 23.

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Abstract

L'invention concerne des polymères à transport de trous à base de triscarbazole étant hautement traitables en solution et capables d'une réticulation par l'application de chaleur et/ou de lumière. Ces polymères permettent une résistance aux solvants et permettent un traitement en solution de couches ultérieures tout en conservant de bonnes propriétés de transport de trous et d'efficacités de dispositif.
PCT/US2012/071506 2011-12-22 2012-12-21 Polymères transporteurs de trous à base de triscarbazole réticulables WO2013096918A1 (fr)

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WO2015030469A1 (fr) * 2013-08-26 2015-03-05 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique contenant ledit composé, et dispositif électronique associé
WO2016159293A1 (fr) * 2015-03-31 2016-10-06 出光興産株式会社 Copolymère, matériau pour élément électronique, matériau pour élément électroluminescent organique et élément électroluminescent organique
CN106397085A (zh) * 2016-09-18 2017-02-15 绵阳高新区达高特科技有限公司 4‑乙烯基苯并环丁烯的合成方法
CN106397085B (zh) * 2016-09-18 2019-02-15 绵阳高新区达高特科技有限公司 4-乙烯基苯并环丁烯的合成方法
WO2018104180A1 (fr) * 2016-12-05 2018-06-14 Thales Polymere pour interface thermique de faible resistance thermique et interface thermique
WO2018228041A1 (fr) * 2017-06-16 2018-12-20 湖北固润科技股份有限公司 Procédé de préparation d'un composé tpo et de co-production d'un composé oxétane à substitution en 3-hydroxyalkyle
CN109134537A (zh) * 2017-06-16 2019-01-04 湖北固润科技股份有限公司 制备tpo系化合物并联产3-羟烷基取代的氧杂环丁烷系化合物的方法
EP3680261A4 (fr) * 2018-02-28 2020-12-16 Lg Chem, Ltd. Polymère, composition de revêtement le comprenant, et élément électroluminescent organique l'utilisant
US11498987B2 (en) 2018-02-28 2022-11-15 Lg Chem, Ltd. Polymer, coating composition comprising same, and organic light emitting element using same

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