WO2013096832A2 - Matières de transport de trous à base de triscarbazole réticulables à petites molécules - Google Patents

Matières de transport de trous à base de triscarbazole réticulables à petites molécules Download PDF

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WO2013096832A2
WO2013096832A2 PCT/US2012/071363 US2012071363W WO2013096832A2 WO 2013096832 A2 WO2013096832 A2 WO 2013096832A2 US 2012071363 W US2012071363 W US 2012071363W WO 2013096832 A2 WO2013096832 A2 WO 2013096832A2
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group
optionally substituted
composition
crosslinking
compounds
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PCT/US2012/071363
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WO2013096832A3 (fr
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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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    • 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
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • 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
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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
    • H10K85/657—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.
  • small molecules that are solution processable and are capable of crosslinking by the application of heat and/or light. These small molecules allow for solvent resistant and allow solution processing of subsequent layers while maintaining good hole transport abilities and device efficiencies. Using small molecule materials obviate the need for polymerization and polymer purification prior to device fabrication.
  • Embodiments described herein include, for example, compositions, articles, devices, and methods for making.
  • composition comprising one or more first compounds represented by formula (I) or formula (II):
  • 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;
  • XL1, XL2, XL3, and XL4 are each independently a crosslinking group;
  • kl, k2, k3, and k4 are each 0, 1 or 2;
  • R is an organic group optionally comprising at least one crosslinking group; and wherein at least one of the first compounds comprises at least two crosslinking groups.
  • composition comprising one or more first compounds represented by formula (XIII) or formula (XIV):
  • Rl, R2, R3, R4, R5, R6, R7, R8, R9, RIO, Rl l, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, and R23 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 said crosslinking group comprises a reactive group RG optionally linked to a linker group L selected from the group consisting of optionally substituted alkylene, optionally substituted arylene, optionally substituted heteroalkylene, oxyalkylene, oligo-oxyalkylene and optionally substituted heteroarylene; and wherein at least one of the first compounds comprises at least two crosslinking groups.
  • 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 one or more first compounds 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 at least one phosphorescent emitter, and the external quantum efficiency of the electroluminescence device at 1,000 cd/m is at least 5% or least 10%.
  • an electroluminescence device comprising: providing an anode layer; depositing the hole transport layer discussed above from solution onto the anode layer; and crosslinking the one or more first compounds to produce a crosslinked hole transport layer, wherein the crosslinked hole transport layer is substantially insolubilized.
  • 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 one or more first compounds are 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 small molecule crosslinking triscarbazole hole transport material described herein.
  • FIG. 3 shows performance of an exemplary OLED device with spin-coated
  • FIG. 4 shows performance of an exemplary OLED device with spin-coated
  • FIG. 5 shows temperature profile and performance of an exemplary OLED device with spin-coated Compound 5.42 hole transport layer cured by rapid thermal processing and evaporation-deposited emitting layer.
  • FIG. 6 shows temperature profile and performance of an exemplary OLED device with spin-coated Compound 5.42 hole transport layer cured by rapid thermal processing and spin-coated emitting layer.
  • FIG. 7 shows temperature profile and performance of an exemplary OLED device with spin-coated hole injection layer, spin-coated Compound 5.42 hole transport layer cured by rapid thermal processing and spin-coated emitting layer.
  • FIG. 8 shows performance of an exemplary OLED device with evaporation-deposited hole injection layer, spin-coated Compound J hole transport layer and spin-coated emitting layer.
  • FIG. 9 shows performance of an exemplary OLED device with spin-coated hole injection layer, spin-coated Compound J hole transport layer and spin-coated emitting layer.
  • FIG. 10 shows performance of an exemplary OLED device with spin-coated hole injection layer, spin-coated Compound J hole transport layer and spin-coated emitting layer.
  • FIG. 11 shows performance of an exemplary OLED device with spin-coated hole injection layer, spin-coated Compound J hole transport layer and spin-coated emitting layer.
  • Optionally substituted groups refers to, for example, functional groups that may be substituted or unsubstituted by additional functional groups.
  • groups for example, when a group is unsubstituted by an additional group it can be referred to as the group name, for example alkyl or aryl.
  • groups 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 refers, 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-", wherein the alkylene can be optionally substituted.
  • Oxyarylene refers to, for example, the group “-arylene-O-", wherein the arylene can be optionally substituted.
  • Carbonyl alkylene refers to, for example, the group “-alkylene-C(O)-", wherein the alkylene can be optionally substituted.
  • Carbonyl arylene refers to, for example, the group “-arylene-C(O)-", wherein the arylene can be optionally substituted.
  • Carboxyl alkylene refers to, for example, the group “-alkylene-C(0)-0-", wherein the alkylene can be optionally substituted.
  • Carboxyl arylene refers to, for example, the group “-arylene-C(0)-0-", wherein the arylene can be optionally substituted.
  • “Ether” refers to, for example, the groups “-alkylene-O-alkylene-", “-arylene-O- alkylene-", and “-arylene-O-arylene-", wherein the alkylene and arylene can be optionally substituted.
  • Ester refers to, for example, the groups “-alkylene-C(0)-0-alkylene-", “-arylene - C(0)-0-alkylene-”, “-arylene-C(0)-0-arylene-”, wherein the alkylene and arylene can be optionally substituted.
  • Ketone refers to, for example, the groups “-alkylene-C(0)-alkylene-", “-arylene- C(0)-alkylene-”, and “-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.
  • compositions comprising one or more first compounds represented by formula (I) or formula (II):
  • the first compound comprises at least two crosslinking groups; XL1, XL2, XL3, and XL4 are each independently a crosslinking group; kl, k2, k3, and k4 are each 0, 1 or 2; R is an organic group optionally comprising at least one crosslinking group; and wherein 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.
  • only the R group of the first compound comprises crosslinking groups, i.e., kl, k2, k3, and k4 are each 0.
  • the R group can comprise, for example, two crosslinking styrene groups.
  • the R group does not comprise any crosslinking group, while the optionally substituted triscarbazole group comprises one or more crosslinking groups.
  • the optionally substituted triscarbazole group can comprise, for example, two vinyl groups each directly linked to a carbocyclic ring of the optionally substituted triscarbazole group.
  • the first compound can be represented by, for example, formula (VII), formula (VIII), formula (IX), or formula (X):
  • Rl, R2, R3, and R4 are each a hydrogen.
  • At least one of Rl, R2, R3, and R4 comprises an optionally substituted carbazole group.
  • Rl, R2, R3, and R4 each comprises an optionally substituted carbazole group.
  • the first compound can be represented by, for example, formula (XI):
  • the one or more first compounds do not comprise any 2- phenyl-5 -phenyl- 1, 3, 4-oxadiazole group. In other embodiments, the one or more first compounds comprise no oxadiazole group.
  • the one or more first compounds can comprise, for example, one or more moieties such as electron transporters, solubilizing groups, and compatibilizing groups.
  • Rl, R2, R3, R4, R5, R6, R7, R8, R9, RIO, Rl l, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, and R23 are each independently a hydrogen, a halogen, an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted heteroalkyl, an optionally substituted heteroaryl, or a crosslinking group; wherein said crosslinking group comprises a reactive group optionally linked to a linker group; and at least one of the first compounds comprises at least two crosslinking groups.
  • the one or more first compounds include both compounds with only one crosslinking group and compounds with two or more crosslinking groups. In another embodiment, the one or more first compounds are a mixture of mono-vinyl compounds and di-vinyl compounds.
  • the R group of the first compound can be represented by, for example, formula (III): ; wherein XL5 is a crosslinking group; k5 is 0, 1, 2 or 3; and wherein R5 is 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 group of the first compound can be represented by, for example, formula (IV):
  • R group of the first compound can be represented by, for example, formula (V):
  • LI and L2 are each independently a linker group.
  • R group of the first compound can be represented by, ample, formula (VI):
  • LI and L2 are each independently a linker group.
  • the R group can be an alkyl group and can be linear or branched.
  • R can be, for example, a C3 - C20 alkyl group.
  • R can be, for example, ethylhexyl.
  • Crosslinking groups are known in the art and described in, for example, Zuniga 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 RG optionally linked to a linker group L.
  • Reactive groups are known in the art. Any reactive group that is capable of crosslinking by heat, light, chemical treatment or a combination thereof are within the scope of this application.
  • the reactive group can be, for example, styrene, acrylate, oxetane, cinnamate, chalcone, trifluorovinylether (TFVE), benzocyclobutane, silane, etc.
  • Examples of the reactive group include the following:
  • X, Y and Z are each independently H, alkyl, F or fluoroalkyl;
  • R' is 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. More specifically, the linker group can be, for example, an alkylene group, an oxyalkylene group, an oligo-oxyalkylene 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 comprises no oxadiazole group.
  • compositions comprising the one or more first compounds described herein are solution-processable and capable of crosslinking, and possess good hole transport ability.
  • the composition can optionally comprise one or more second compounds.
  • the second compounds can comprise, for example, one or more moieties such as electron transporters, solubilizing groups, compatibilizing groups, or crosslinking groups.
  • the second compounds comprise at least one crosslinking group that comprises at least one reactive group having similar reactivity to the reactive group of the first compounds.
  • the composition does not comprise any 2-phenyl-5-phenyl- 1,3,4-oxadiazole group. In other embodiments, the composition comprises no oxadiazole group.
  • compositions and compounds described herein can be unexpectedly effective as hole transport material, and can be used to make highly efficient and stable OLED devices.
  • compositions and compounds 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 normal OLED operation.
  • compositions and compounds described herein can be readily soluble in common organic solvents. Optionally, they may be sublimable under high vacuum. These compositions and compounds 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 first crosslinking compounds described herein.
  • the hole transport layer can further comprise, for example, one or more second crosslinking compounds.
  • the hole transport layer can be fabricated from a solution comprising the solution- processable crosslinking compounds described herein.
  • the solution can further comprise, for example, an organic solvent such as cholorobenzene, 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 crosslinking compound, or between 0.2-25 wt.% of the crosslinking compound, or between 0.5-10 wt.% of crosslinking compound, or between 1-5 wt.% of the crosslinking compound.
  • the hole transport layer can be fabricated by methods known in the art. Examples include spin coating from solution and vacuum vapor deposition. 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 material described herein modified by soluble molecular p-dopants known in the art.
  • Examples of 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. Particularly useful are "Mo(tfd)3" and “Cr(tfd)3" as dopants:
  • 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 compounds described herein.
  • the electroluminescence device may also comprise an electron transport layer.
  • ITO inert and transparent substrate
  • suitable materials for anode in electroluminescence devices include, for example, ITO, which can be applied by vacuum deposition in a layer over an inert and transparent substrate such as glass.
  • 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-difluoro-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 comprises a crosslinked hole transport layer, wherein the first compound in the hole transport layer can be, for example, thermally crosslinked or photochemically crosslinked.
  • the crosslinking of the first compound in the hole transport layer can result in, for example, an insoluble organic layer resistant to degradation by solution processing of a subsequent layer.
  • the electroluminescence device comprises an emissive layer comprising 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 compounds 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 compound 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.
  • Advantages of RTP include, for example, increasing throughput and minimizing the time that the material is subjected to high temperature.
  • 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 compounds 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 small molecule is provided with a multicarbazole like structure I, where R is a moiety having at least two reactive groups that can form a
  • R can be other carbazole units.
  • the R group may have two styrene groups that can form a crosslinked matrix.
  • Each carbazole ring can be further substituted with halogens, alkyl, heteroalkyl groups (e.g., functional groups), aryl, or heteroaryl groups. Examples are 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 size of the multicarbazoles may be varied to change properties such as solubility, processability, viscosity of deposition solvents, mechanical strength, etc.
  • the multicarbazoles can be combined with other molecules such as electron transporters, solubilizing groups, compatibilizing groups, crosslinker groups, etc.
  • the other molecules may have reactive groups that are the same or similar in reactivity to the reactive groups on multicarbazole so that they are incorporated into the multicarbazole matrix.
  • Devices having multicarbazoles with crosslinking groups show good efficiency and can have solution deposition of subsequent devices layers.
  • 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, ⁇ 0 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.
  • Compound 5.42 was processed in the glove box under nitrogen. 10 mg of Compound 5.42 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 200 °C for 30 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 Compound 5.42 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, FINOs: 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.
  • Compound 5.42 was processed in the glove box under nitrogen. 10 mg of Compound 5.42 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 1 10 °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.
  • 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 the Compound 5.42 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 small molecule crosslinking hole transport material with triscarbazole like groups are suitable as HTLs for solution processing of subsequent layers.
  • various small molecules 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, ⁇ 0 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.
  • Compound 5.42 was processed in the glove box under nitrogen. 10 mg of Compound 5.42 was dissolved in 1 ml 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 200 °C for 30 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 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. 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, 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.
  • Compound 5.42 was processed in the glove box under nitrogen. 10 mg of Compound 5.42 was dissolved in 1 ml 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 200 °C for 30 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 chlorobenzene.
  • the solutions of the polymers were then mixed together (1 ml 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.
  • 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 6(B)-(C).
  • a device is fabricated in substantially the same way as in Example 5, except that a PEDOT:PSS hole injection layer was deposited between the ITO substrate and the
  • 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.
  • the RTP procedure temperature profile is presented in Figure 7(A).
  • the performance of the device is shown in Figure 7(B)-(C).
  • Triscarbazole compound J was prepared by organic synthetic and purification methods.
  • the compound has a branched R group and two vinyl crosslinking groups.
  • 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.
  • the hole injection layer, M0O 3 (Aldirch) was thermally evaporated at 0.2 A/s.
  • the pressure in the vacuum chamber was 1 x 10 "7 Torr.
  • Compound J was processed in the glove box under nitrogen. 10 mg of Compound J was dissolved in 1.5 ml of toluene. Around 35 nm thick films of the hole-transport material were spin-coated at 2000 rpm, acceleration 1000 rpm/sec for 60 sec. The films were then dried on a hot plate at 110 °C for 3 minutes followed by thermal curing at 150 °C for 15 min. A watch glass was used during the curing process over the samples in order to avoid excessive heat loses.
  • Emissive layer consisting of a Compound F host (an oxadiazole compound) and emitter was prepared in the following way in the glove box: 10 mg of Compound F was dissolved in 1.5 ml toluene and 10 mg of Ir(pppy) 3 (Solvay) in 1.5 ml of toluene. 64 ⁇ of Ir(pppy) 3 was added to 1 ml of the solution of XH-I-163a. 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 2 min.
  • a device is fabricated in substantially the same way as in Example 8, except that the hole injection layer comprises PEDOT:PSS instead of M0O 3 .
  • the hole injection layer comprises PEDOT:PSS instead of M0O 3 .
  • 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.
  • LiF/Al/Ag (2.5/60 nm/100 nm)
  • a device is fabricated in substantially the same way as in Example 9, except that the electron transport layer comprises TmPyPB instead of BCP.
  • LiF/Al/Ag (2.5/60 nm/100 nm)
  • PEDOT PSS AI 4083 (50 nm)
  • a device is fabricated in substantially the same way as in Example 9, except that the electron transport layer comprises TpPyPB instead of BCP.
  • TpPyPB the electron transport layer

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

La présente invention concerne des petites molécules qui sont aptes à être traitées en solution et aptes à être réticulées par l'application de chaleur et/ou de lumière. Ces petites molécules permettent une résistance au solvant et permettent un traitement en solution de couches ultérieures tout en maintenant de bonnes capacités de transport de trous et de bons rendements de dispositif. Ces matières à petites molécules pallient le besoin de polymérisation et de purification de polymère avant la fabrication de dispositif.
PCT/US2012/071363 2011-12-22 2012-12-21 Matières de transport de trous à base de triscarbazole réticulables à petites molécules WO2013096832A2 (fr)

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KR20130105459A (ko) * 2012-03-15 2013-09-25 유니버셜 디스플레이 코포레이션 트리카르바졸 화합물을 가진 제2 정공 수송층
KR102141720B1 (ko) 2012-03-15 2020-08-06 유니버셜 디스플레이 코포레이션 트리카르바졸 화합물을 가진 제2 정공 수송층
WO2014193215A1 (fr) * 2013-05-27 2014-12-04 Universiti Malaya (Um) Diode électroluminescente organique et son procédé de fabrication
WO2016105161A3 (fr) * 2014-12-26 2016-11-24 주식회사 두산 Composé organique et élément électroluminescent organique comprenant ce composé
JP6187847B1 (ja) * 2015-10-21 2017-08-30 Dic株式会社 活性エネルギー線硬化型組成物及びプラスチックレンズ
JP6187846B1 (ja) * 2015-10-21 2017-08-30 Dic株式会社 活性エネルギー線硬化型組成物及びプラスチックレンズ
WO2017068988A1 (fr) * 2015-10-21 2017-04-27 Dic株式会社 Composition active durcissable au rayonnement d'énergie et lentille en plastique
KR20180073587A (ko) * 2015-10-21 2018-07-02 디아이씨 가부시끼가이샤 활성 에너지선 경화형 조성물 및 플라스틱 렌즈
WO2017068989A1 (fr) * 2015-10-21 2017-04-27 Dic株式会社 Composition durcissable par un rayonnement d'énergie active et lentille en plastique
TWI708809B (zh) * 2015-10-21 2020-11-01 日商迪愛生股份有限公司 活性能量線硬化型組成物及塑膠透鏡
TWI722029B (zh) * 2015-10-21 2021-03-21 日商迪愛生股份有限公司 活性能量線硬化型組成物及塑膠透鏡
KR102588912B1 (ko) 2015-10-21 2023-10-16 디아이씨 가부시끼가이샤 활성 에너지선 경화형 조성물 및 플라스틱 렌즈
US11629126B2 (en) 2016-10-06 2023-04-18 Merck Patent Gmbh Materials for organic electroluminescent devices

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