WO2010059837A2 - Composés de chrysène pour des applications de luminescence bleue ou verte - Google Patents

Composés de chrysène pour des applications de luminescence bleue ou verte Download PDF

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WO2010059837A2
WO2010059837A2 PCT/US2009/065163 US2009065163W WO2010059837A2 WO 2010059837 A2 WO2010059837 A2 WO 2010059837A2 US 2009065163 W US2009065163 W US 2009065163W WO 2010059837 A2 WO2010059837 A2 WO 2010059837A2
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group
compound
phenyl
groups
different
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PCT/US2009/065163
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WO2010059837A3 (fr
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Weishi Wu
Norman Herron
Vsevolod Rostovtsev
Jeffrey A. Merlo
Weiying Gao
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E. I. Du Pont De Nemours And Company
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Priority to CN2009801467738A priority Critical patent/CN102216417A/zh
Priority to JP2011537619A priority patent/JP5687628B2/ja
Priority to KR1020117013948A priority patent/KR101495396B1/ko
Priority to US13/120,001 priority patent/US20110215715A1/en
Priority to EP09828227A priority patent/EP2350230A4/fr
Publication of WO2010059837A2 publication Critical patent/WO2010059837A2/fr
Publication of WO2010059837A3 publication Critical patent/WO2010059837A3/fr

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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/38—Polycyclic condensed hydrocarbons containing four rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/001—Pyrene dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/701—Langmuir Blodgett films
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/86—Ring systems containing bridged rings containing four rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

Definitions

  • This invention relates to electroluminescent chrysene compounds which have blue or green emission. It also relates to electronic devices in which the active layer includes such a chrysene compound. Description of the Related Art
  • Organic electronic devices that emit light, such as light-emitting diodes that make up displays, are present in many different kinds of electronic equipment.
  • an organic active layer is sandwiched between two electrical contact layers. At least one of the electrical contact layers is light-transmitting so that light can pass through the electrical contact layer.
  • the organic active layer emits light through the light-transmitting electrical contact layer upon application of electricity across the electrical contact layers.
  • organic electroluminescent compounds As the active component in light-emitting diodes. Simple organic molecules such as anthracene, thiadiazole derivatives, and coumarin derivatives are known to show electroluminescence. Semiconductive conjugated polymers have also been used as electroluminescent components, as has been disclosed in, for example, U.S. Patent 5,247,190, U.S. Patent 5,408,109, and Published European Patent Application 443 861. However, there is a continuing need for electroluminescent compounds, especially compounds that are blue-emitting.
  • R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of H and alkyl, where R 1 and R 2 groups or
  • R 3 and R 4 groups may be joined together to form a 5- or 6- membered aliphatic ring;
  • R 5 and R 6 are the same or different and are selected from the group consisting of alkyl groups, m-phenyl, o-phenyl, p-phenyl, m-carbazolyl, and p-carbazolyl;
  • R 7 is the same or different at each occurrence and is selected from the group consisting of alkyl groups, phenyl, and biphenyl, or two adjacent R 7 groups can join together to form a naphthyl group;
  • a and b are the same or different and are an integer from 0-10;
  • c and d are the same or different and are an integer from 1 -3;
  • f, g, h, and i are the same or different at each occurrence and are an integer from 0-4; and
  • e and j are the same or different at each occurrence and are an integer from 0-5.
  • FIG. 1 includes an illustration of one example of an organic electronic device.
  • FIG. 2 includes a graph of relative device lifetimes. Skilled artisans appreciate that objects in the figures are illustrated for simplicity and clarity and have not necessarily been drawn to scale. For example, the dimensions of some of the objects in the figures may be exaggerated relative to other objects to help to improve understanding of embodiments.
  • aliphatic ring is intended to mean a cyclic group that does not have delocalized pi electrons. In some embodiments, the aliphatic ring has no unsaturation. In some embodiments, the ring has one double or triple bond.
  • alkyl is intended to mean a group derived from an aliphatic hydrocarbon having one point of attachment, and includes a linear, a branched, or a cyclic group. The term is intended to include heteroalkyls.
  • hydrocarbon alkyl refers to an alkyl group having no heteroatoms. In some embodiments, an alkyl group has from 1 -20 carbon atoms.
  • aryl is intended to mean a group derived from an aromatic hydrocarbon having one point of attachment. The term includes groups which have a single ring and those which have multiple rings which can be joined by a single bond or fused together. The term is intended to include heteroaryls.
  • arylene is intended to mean a group derived from an aromatic hydrocarbon having two points of attachment. In some embodiments, an aryl group has from 3-60 carbon atoms.
  • the term “blue” refers to radiation that has an emission maximum at a wavelength in a range of approximately 400-500 nm.
  • branched alkyl refers to an alkyl group having at least one secondary or tertiary carbon.
  • secondary alkyl refers to a branched alkyl group having a secondary carbon atom.
  • tertiary alkyl refers to a branched alkyl group having a tertiary carbon atom. In some embodiments, the branched alkyl group is attached via a secondary or tertiary carbon.
  • the term "compound” is intended to mean an electrically uncharged substance made up of molecules that further consist of atoms, wherein the atoms cannot be separated by physical means.
  • the phrase "adjacent to,” when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
  • the phrase “adjacent R groups,” is used to refer to R groups that are next to each other in a chemical formula (i.e., R groups that are on atoms joined by a bond).
  • photoactive refers to any material that exhibits electroluminescence and/or photosensitivity.
  • green refers to radiation that has an emission maximum at a wavelength in a range of approximately 500-600 nm.
  • the prefix "hetero” indicates that one or more carbon atoms have been replaced with a different atom.
  • the different atom is N, O, or S.
  • the term “layer” is used interchangeably with the term “film” and refers to a coating covering a desired area. The term is not limited by size. The area can be as large as an entire device or as small as a specific functional area such as the actual visual display, or as small as a single sub-pixel. Layers and films can be formed by any conventional deposition technique, including vapor deposition, liquid deposition (continuous and discontinuous techniques), and thermal transfer. Continuous deposition techniques, include but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot-die coating, spray coating, and continuous nozzle coating. Discontinuous deposition techniques include, but are not limited to, ink jet printing, gravure printing, and screen printing.
  • organic electronic device or sometimes just “electronic device” is intended to mean a device including one or more organic semiconductor layers or materials. All groups are unsubstituted unless otherwise indicated. In some embodiments, the substituents are selected from the group consisting of halide, alkyl, alkoxy, aryl, and cyano.
  • One aspect of the present invention is a composition of Formula I:
  • R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of H and alkyl, where R 1 and R 2 groups or
  • R 3 and R 4 groups may be joined together to form a 5- or 6- membered aliphatic ring;
  • R 5 and R 6 are the same or different and are selected from the group consisting of alkyl groups, m-phenyl, o-phenyl, p-phenyl, m-carbazolyl, and p-carbazolyl;
  • R 7 is the same or different at each occurrence and is selected from the group consisting of alkyl groups, phenyl, and biphenyl, or two adjacent R 7 groups can join together to form a naphthyl group; a and b are the same or different and are an integer from 0-10; c and d are the same or different and are an integer from 1 -3; f, g, h, and i, are the same or different at each occurrence and are an integer from 0-4; and e and j are the same or different at each occurrence and are an integer from 0-5.
  • R 1 through R 4 are hydrocarbon alkyl groups.
  • R 1 is a branched hydrocarbon alkyl group and R 2 through R 4 are H.
  • the branched hydrocarbon alkyl group has from 3-8 carbon atoms.
  • the branched hydrocarbon alkyl group is a secondary alkyl selected from the group consisting of isopropyl and 2-butyl.
  • the branched hydrocarbon alkyl group is a tertiary alkyl selected from the group consisting of t-butyl and 2-(2-methyl)-butyl.
  • R 1 and R 2 taken together and R 3 and R 4 taken together form a 5- or 6-membered aliphatic ring.
  • the aliphatic ring is selected from the group consisting of cyclohexyl and cyclopentyl.
  • the aliphatic ring has one or more alkyl substituents.
  • R 1 and R 2 taken together form a 5- or 6-membered aliphatic ring and R 3 and R 4 are H.
  • each of R 1 through R 4 is H.
  • R 5 and R 6 are aromatic groups selected from the group consisting of o-phenyl, m-phenyl, p-phenyl, m-carbazolyl, and p-carbazolyl groups.
  • m-carbazolyl is meant the group
  • R 7 is a hydrocarbon alkyl group having 1 -10 carbon atoms.
  • at least one of e through j is greater than 0.
  • a and b are 1-10. In some embodiments, a and b are 2-5.
  • the chrysene compound is selected from compounds E1 through E17:
  • the new chrysenes can be prepared by known coupling and substitution reactions. Exemplary preparations are given in the Examples.
  • the chrysene compounds described herein can be formed into films using liquid deposition techniques. Thin films of these materials dispersed in a host matrix exhibit good to excellent photoluminescent properties and blue or green emission.
  • the chrysene compounds described herein have a multi-phenyl substituent on the amino nitrogens.
  • the multi-phenyl group can be biphenyl, terphenyl, quaterphenyl, and above.
  • these compounds have greatly improved properties when compared to chrysene compounds having only single phenyl substituents on the amino nitrogens.
  • Electronic devices including an active layer with the chrysene compounds described herein have greatly improved lifetimes. It has been discovered that the lifetime increases with the number of repeat units on the nitrogen substituent. In addition, the lifetime increases are achieved in combination with high quantum efficiency and good color.
  • Electronic Device Organic electronic devices that may benefit from having one or more layers comprising the blue luminescent materials described herein include, but are not limited to, (1 ) devices that convert electrical energy into radiation (e.g., a light-emitting diode, light emitting diode display, or diode laser), (2) devices that detect signals through electronics processes (e.g., photodetectors, photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes, IR detectors), (3) devices that convert radiation into electrical energy, (e.g., a photovoltaic device or solar cell), and (4) devices that include one or more electronic components that include one or more organic semi-conductor layers (e.g., a transistor or diode).
  • (1 ) devices that convert electrical energy into radiation e.g., a light-emitting diode, light emitting diode display, or diode laser
  • devices that detect signals through electronics processes e.g., photodetectors, photoconductive cells, photoresis
  • the device 100 has a first electrical contact layer, an anode layer 110 and a second electrical contact layer, a cathode layer 160, and a photoactive layer 140 between them.
  • Adjacent to the anode is a buffer layer 120.
  • Adjacent to the buffer layer is a hole transport layer 130, comprising hole transport material.
  • Adjacent to the cathode may be an electron transport layer 150, comprising an electron transport material.
  • devices may use one or more additional hole injection or hole transport layers (not shown) next to the anode 110 and/or one or more additional electron injection or electron transport layers (not shown) next to the cathode 160.
  • Layers 120 through 150 are individually and collectively referred to as the active layers.
  • the different layers have the following range of thicknesses: anode 110, 500-5000 A, in one embodiment 1000-2000 A; buffer layer 120, 50-2000 A, in one embodiment 200-1000 A; hole transport layer 130, 50-2000 A, in one embodiment 200-1000 A; photoactive layer 140, 10-2000 A, in one embodiment 100-1000 A; layer 150, 50-2000 A, in one embodiment 100-1000 A; cathode 160, 200-10000 A, in one embodiment 300-5000 A.
  • the location of the electron-hole recombination zone in the device, and thus the emission spectrum of the device, can be affected by the relative thickness of each layer.
  • the desired ratio of layer thicknesses will depend on the exact nature of the materials used.
  • the photoactive layer 140 can be a light-emitting layer that is activated by an applied voltage (such as in a light-emitting diode or light-emitting electrochemical cell), or a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
  • an applied voltage such as in a light-emitting diode or light-emitting electrochemical cell
  • a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage
  • Examples of photodetectors include photoconductive cells, photoresistors, photoswitches, phototransistors, and phototubes, and photovoltaic cells, as these terms are described in Markus, John, Electronics and Nucleonics Dictionary, 470 and 476 (McGraw-Hill, Inc. 1966).
  • the chrysene compounds of Formula I are useful as photoactive materials in layer 140.
  • the compounds can be used alone, or in combination with a host material.
  • the host is a bis-condensed cyclic aromatic compound.
  • the host is an anthracene derivative compound.
  • the compound has the formula:
  • An is an anthracene moiety; L is a divalent connecting group.
  • L is a single bond, -O-, -S-, - N(R)-, or an aromatic group.
  • An is a mono- or diphenylanthryl moiety.
  • the host has the formula: A - An - A where:
  • An is an anthracene moiety; A is the same or different at each occurrence and is an aromatic group.
  • the A groups are attached at the 9- and 10- positions of the anthracene moiety.
  • A is selected from the group consisting naphthyl, naphthylphenylene, and naphthylnaphthylene.
  • the compound is symmetrical and in some embodiments the compound is non-symmetrical.
  • the host has the formula:
  • the host is selected from the group consisting of H1
  • the chrysene compounds of Formula I in addition to being useful as emissive dopants in the photoactive layer, can also act as charge carrying hosts for other emissive dopants in the photoactive layer 140. b. Other Device Layers
  • the other layers in the device can be made of any materials that are known to be useful in such layers.
  • the anode 110 is an electrode that is particularly efficient for injecting positive charge carriers. It can be made of, for example, materials containing a metal, mixed metal, alloy, metal oxide or mixed- metal oxide, or it can be a conducting polymer, or mixtures thereof. Suitable metals include the Group 11 metals, the metals in Groups 4-6, and the Group 8-10 transition metals. If the anode is to be light- transmitting, mixed-metal oxides of Groups 12, 13 and 14 metals, such as indium-tin-oxide, are generally used.
  • the anode 110 can also comprise an organic material such as polyaniline as described in "Flexible light- emitting diodes made from soluble conducting polymer," Nature vol. 357, pp 477-479 (11 June 1992). At least one of the anode and cathode is desirably at least partially transparent to allow the generated light to be observed.
  • the buffer layer 120 comprises buffer material and may have one or more functions in an organic electronic device, including but not limited to, planahzation of the underlying layer, charge transport and/or charge injection properties, scavenging of impurities such as oxygen or metal ions, and other aspects to facilitate or to improve the performance of the organic electronic device.
  • Buffer materials may be polymers, oligomers, or small molecules. They may be vapour deposited or deposited from liquids which may be in the form of solutions, dispersions, suspensions, emulsions, colloidal mixtures, or other compositions.
  • the buffer layer can be formed with polymeric materials, such as polyaniline (PANI) or polyethylenedioxythiophene (PEDOT), which are often doped with protonic acids.
  • the protonic acids can be, for example, poly(styrenesulfonic acid), poly(2-acrylamido-2-methyl-1 -propanesulfonic acid), and the like.
  • the buffer layer can comprise charge transfer compounds, and the like, such as copper phthalocyanine and the tetrathiafulvalene- tetracyanoquinodimethane system (TTF-TCNQ).
  • charge transfer compounds such as copper phthalocyanine and the tetrathiafulvalene- tetracyanoquinodimethane system (TTF-TCNQ).
  • the buffer layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer.
  • electrically conductive polymer and at least one fluorinated acid polymer.
  • fluorinated acid polymer Such materials have been described in, for example, published U.S. patent applications 2004-0102577, 2004-0127637, and 2005/205860 Examples of hole transport materials for layer 130 have been summarized for example, in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Vol. 18, p. 837-860, 1996, by Y. Wang. Both hole transporting molecules and polymers can be used.
  • hole transporting molecules are: N,N'-diphenyl-N,N'-bis(3-methylphenyl)- [1 ,1'-biphenyl]-4,4'-diamine (TPD), 1 ,1 -bis[(di-4-tolylamino) phenyl]cyclohexane (TAPC), N,N'-bis(4-methylphenyl)-N,N'-bis(4- ethylphenyl)-[1 ,1 '-(3,3'-dimethyl)biphenyl]-4,4'-diamine (ETPD), tetrakis-(3- methylphenyl)-N,N,N',N'-2,5-phenylenediamine (PDA), a-phenyl-4-N,N- diphenylaminostyrene (TPS), p-(diethylamino)benzaldehyde diphenylhydrazone (DEH),
  • hole transporting polymers are polyvinylcarbazole, (phenylmethyl)- polysilane, and polyaniline. It is also possible to obtain hole transporting polymers by doping hole transporting molecules such as those mentioned above into polymers such as polystyrene and polycarbonate. In some cases, triarylamine polymers are used, especially tharylamine-fluorene copolymers. In some cases, the polymers and copolymers are crosslinkable.
  • additional electron transport materials which can be used in layer 150 include metal chelated oxinoid compounds, such as tris(8-hydroxyquinolato)aluminum (Alq3); bis(2-methyl-8- quinolinolato)(para-phenyl-phenolato)aluminum(lll) (BAIQ); and azole compounds such as 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1 ,3,4-oxadiazole (PBD) and 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1 ,2,4-triazole (TAZ), and 1 ,3,5-th(phenyl-2-benzimidazole)benzene (TPBI); quinoxaline derivatives such as 2,3-bis(4-fluorophenyl)quinoxaline; phenanthroline derivatives such as 9,10-diphenylphenanthroline (DPA) and 2,9-
  • the cathode 160 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
  • the cathode can be any metal or nonmetal having a lower work function than the anode.
  • Materials for the cathode can be selected from alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, including the rare earth elements and lanthanides, and the actinides. Materials such as aluminum, indium, calcium, barium, samarium and magnesium, as well as combinations, can be used.
  • Li-containing organometallic compounds, LiF, and Li 2 O can also be deposited between the organic layer and the cathode layer to lower the operating voltage.
  • anode 110 there can be a layer (not shown) between the anode 110 and buffer layer 120 to control the amount of positive charge injected and/or to provide band-gap matching of the layers, or to function as a protective layer.
  • Layers that are known in the art can be used, such as copper phthalocyanine, silicon oxy-nitride, fluorocarbons, silanes, or an ultra-thin layer of a metal, such as Pt.
  • some or all of anode layer 110, active layers 120, 130, 140, and 150, or cathode layer 160 can be surface-treated to increase charge carrier transport efficiency.
  • the choice of materials for each of the component layers is preferably determined by balancing the positive and negative charges in the emitter layer to provide a device with high electroluminescence efficiency.
  • each functional layer can be made up of more than one layer.
  • the device can be prepared by a variety of techniques, including sequential vapor deposition of the individual layers on a suitable substrate. Substrates such as glass, plastics, and metals can be used. Conventional vapor deposition techniques can be used, such as thermal evaporation, chemical vapor deposition, and the like. Alternatively, the organic layers can be applied from solutions or dispersions in suitable solvents, using conventional coating or printing techniques, including but not limited to spin-coating, dip-coating, roll-to-roll techniques, ink-jet printing, screen- printing, gravure printing and the like.
  • the present invention also relates to an electronic device comprising at least one active layer positioned between two electrical contact layers, wherein the at least one active layer of the device includes the chrysene compound of Formula 1. Devices frequently have additional hole transport and electron transport layers.
  • the HOMO (highest occupied molecular orbital) of the hole transport material desirably aligns with the work function of the anode
  • the LUMO (lowest un-occupied molecular orbital) of the electron transport material desirably aligns with the work function of the cathode.
  • Chemical compatibility and sublimation temperature of the materials are also important considerations in selecting the electron and hole transport materials.
  • the efficiency of devices made with the chrysene compounds described herein can be further improved by optimizing the other layers in the device.
  • more efficient cathodes such as Ca, Ba or LiF can be used.
  • Shaped substrates and novel hole transport materials that result in a reduction in operating voltage or increase quantum efficiency are also applicable.
  • Additional layers can also be added to tailor the energy levels of the various layers and facilitate electroluminescence.
  • the chrysene compounds of the invention often are fluorescent and photoluminescent and can be useful in applications other than OLEDs, such as oxygen sensitive indicators and as fluorescent indicators in bioassays.
  • This example illustrates the preparation of Compound E1.
  • This example illustrates the preparation of Compound E2, N 6 ,N 12 -di(biphenyl-4-yl)-3-fe/t-butyl-N 6 ,N 12 -bis(4-fe/t-butylphenyl)chrysene- 6,12-diamine.
  • reaction mixture was added to the reaction mixture, stirred for 10 minutes and followed by sodium te/t-butoxide (0.782 g, 8.14 mmol) and 20 ml of dry toluene. After another 10 minutes, the reaction flask was brought out of the drybox, attached to a nitrogen line and stirred at 80 0 C overnight. Next day, reaction mixture was cooled to room temperature and filtered through a 4 inch plug of silica gel and one inch of celite, washing with one liter of chloroform and 300 ml of dichloromethane. Removal of volatiles under reduced pressure gave a yellow solid.
  • Example 3 This example illustrates the preparation of Compound E4.
  • This example illustrates the preparation of Compound E5.
  • Pd2(dba)3 () and P(te/t-Bu)3 () were dissolved in 3 ml of dry toluene and set aside for five minutes.
  • 6,12-Dibromochrysene () and N-(4- te/t-buyyl phenyl)- 4,4' terphenylamine () were combined in the reaction flask and dissolved in dry toluene (25 ml).
  • Pre-formed catalyst solution was added next, reaction mixture was stirred for three minutes, followed by the addition of sodium te/t-butoxide (). Reaction was stirred at 100 0 C for 16 hours.
  • This example illustrates the preparation of Compound E6. Take 0.39g of the dibromo-methylchrysene (1 mM) in glove box and add 0.75g (2.1 mM) sec amine and 0.22g t-BuONa (2.2mM) with 10mL toluene. Add 0.15g Pd2DBA3 (0.15mM), 0.06g P(t-Bu)3 (0.3OmM) dissolved in toluene. Mix and heat in glove box in mantle at 8OC under nitrogen for 1 hr. Solution immediately is dark purple but on reaching ⁇ 80C it is dark yellow brown with noticeable blue luminescence.
  • This example illustrates the preparation of Compound E7. Take 0.39g of the dibromochrysene (1 mM) in glove box and add 0.75g (2.1 mM) sec amine and 0.22g t-BuONa (2.2mM) with 10mL toluene. Add 0.15g Pd2DBA3 (0.15mM), 0.06g P(t-Bu)3 (0.3OmM) dissolved in xylenes. Mix and heat in glove box in mantle at 110C under nitrogen for 1 hr. Solution immediately is dark purple but on reaching ⁇ 80C it is dark yellow brown with noticeable blue luminescence. Warm at ⁇ 80C overnight.
  • This example illustrates the preparation of Compound E8. Take 0.39g of the dibromochrysene (1 mM) in glove box and add 0.75g (2.1 mM) sec amine and 0.22g t-BuONa (2.2mM) with 10mL toluene. Add 0.15g Pd2DBA3 (0.15mM), 0.06g P(t-Bu)3 (0.3OmM) dissolved in toluene. Mix and heat in glove box in mantle at 110C under nitrogen for 1 hr. Solution immediately is dark purple but on reaching ⁇ 80C it is dark yellow brown with noticeable blue luminescence. Warm at ⁇ 80C overnight.
  • This example illustrates the preparation of Compound E11. Take 0.386g of the dibromochrysene (1.0 mM) in glove box and add 1.35g (2.1 mM) sec amine and 0.22g t-BuONa (2.2mM) with 10mL xylene. Add 0.15g Pd2DBA3 (0.15mM), 0.06g P(t-Bu)3 (0.3OmM) dissolved in xylenes. Mix and heat in glove box in mantle at 110C under nitrogen for 1 hr. Solution immediately is dark purple but on reaching ⁇ 80C it is light yellow brown with noticeable blue luminescence. Warm at ⁇ 80C for 1 hr.
  • This example illustrates the preparation of Compound E12. Take 0.39g of the dibromochrysene (1 mM) in glove box and add 1.0Og (2.1 mM) sec amine (100555-202) and 0.22g t-BuONa (2.2mM) with 10mL xylenes. Add 0.15g Pd2DBA3 (0.15mM), 0.06g P(t-Bu)3 (0.3OmM) dissolved in xylenes. Mix and heat in glove box in mantle at 110C under nitrogen for 1 hr. Solution immediately is dark purple but on reaching ⁇ 80C it is dark yellow brown with noticeable blue luminescence.
  • This example illustrates the preparation of Compound E15, N6,N12-bis(4-(biphenyl-3-yl)phenyl-2-yl) -N6,N12-bis(2,4- dimethylphenyl)chrysene-6,12-diamine.
  • This example illustrates the preparation of Compound E16.
  • a round-bottom flask was charged with 6,12-dibromochrysene (220 mg, 1.0 eq), N-(2,4-dimethylphenyl)-3"'-/so-propyl-4,4',4"- quaterphenylamine (570 mg, 2.02 eq), Pd 2 (dba) 3 (11 mg, 0.02 eq), P(tert- Bu) 3 (10 mg, 0.08 eq), sodium terf-butoxide (174 mg, 3.0 eq) and m-xylene (15 ml_). Reaction mixture was heated at 120 0 C for 16 hours. Color of the mixture turned from reddish to yellowish.
  • ITO Indium Tin Oxide
  • buffer layer Buffer 1 (25 nm), which is an aqueous dispersion of an electrically conductive polymer and a polymeric fluohnated sulfonic acid.
  • hole transport layer polymer P1 (20 nm)
  • photoactive layer 13:1 host H2:dopant (48 nm)
  • electron transport layer a metal quinolate derivative (20 nm)
  • cathode LiF/AI (0.5/100 nm)
  • OLED devices were fabricated by a combination of solution processing and thermal evaporation techniques.
  • Patterned indium tin oxide (ITO) coated glass substrates from Thin Film Devices, lnc were used. These ITO substrates are based on Corning 1737 glass coated with ITO having a sheet resistance of 30 ohms/square and 80% light transmission.
  • the patterned ITO substrates were cleaned ultrasonically in aqueous detergent solution and rinsed with distilled water.
  • the patterned ITO was subsequently cleaned ultrasonically in acetone, rinsed with isopropanol, and dried in a stream of nitrogen.
  • ITO substrates were treated with UV ozone for 10 minutes.
  • an aqueous dispersion of Buffer 1 was spin-coated over the ITO surface and heated to remove solvent.
  • the substrates were then spin-coated with a solution of a hole transport material, and then heated to remove solvent.
  • the substrates were spin-coated with the emissive layer solution, and heated to remove solvent.
  • the substrates were masked and placed in a vacuum chamber.
  • the electron transport layer was deposited by thermal evaporation, followed by a layer of LiF.
  • Masks were then changed in vacuo and a layer of Al was deposited by thermal evaporation.
  • the chamber was vented, and the devices were encapsulated using a glass lid, dessicant, and UV curable epoxy.
  • Table 1 The different structures are summarized in Table 1.
  • the OLED samples were characterized by measuring their (1 ) current-voltage (I-V) curves, (2) electroluminescence radiance versus voltage, and (3) electroluminescence spectra versus voltage. All three measurements were performed at the same time and controlled by a computer.
  • the current efficiency of the device at a certain voltage is determined by dividing the electroluminescence radiance of the LED by the current density needed to run the device.
  • the unit is a cd/A.
  • the power efficiency is the current efficiency divided by the operating voltage.
  • the unit is Im/W.
  • Table 2 The following dopants were used:
  • the devices were made using the procedure of Example 15, except that the hole transport layer was P2.
  • Example 21 E6
  • Example 22 E7
  • Example 18 show the performance of a device made with a fourth structure having different layer thicknesses and a different hole transport layer.
  • the dopants used were:
  • Buffer layer Buffer 1 for all
  • HTL hole transport layer
  • ETL electron transport layer, which is the same metal quinolate compound for all
  • CE current efficiency
  • CIEx and CIEy are the x and y color coordinates according to the C. I. E. chromaticity scale (Commission Internationale de L'Eclairage, 1931 ).
  • Lum. /4 Life is defined as the time in hours for a device to reach one- half the initial luminance.
  • Relative lifetime is defined as (Lum Vi Life of Example X)/(Lum Vi Life of Comparative Example Y) where Comparative Example Y is the comparative example with the same device structure and materials (other than the dopant).
  • the relative lifetime for Example 23 would be (Lum. Vi Life of Example 23) divided by (Lum.

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  • Electroluminescent Light Sources (AREA)
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Abstract

Cette invention concerne des composés de chrysène qui sont utiles dans des applications d'électroluminescence et qui sont capables d'une émission de bleu ou de vert. L'invention concerne également des dispositifs électroniques dans lesquels la couche active comprend un tel composé de chrysène.
PCT/US2009/065163 2008-11-19 2009-11-19 Composés de chrysène pour des applications de luminescence bleue ou verte WO2010059837A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN2009801467738A CN102216417A (zh) 2008-11-19 2009-11-19 用于蓝色或绿色发光应用的*化合物
JP2011537619A JP5687628B2 (ja) 2008-11-19 2009-11-19 青色または緑色ルミネセンス用途のクリセン化合物
KR1020117013948A KR101495396B1 (ko) 2008-11-19 2009-11-19 청색 또는 녹색 발광 용도를 위한 크라이센 화합물
US13/120,001 US20110215715A1 (en) 2008-11-19 2009-11-19 Chrysene compounds for blue or green luminescent applications
EP09828227A EP2350230A4 (fr) 2008-11-19 2009-11-19 Composés de chrysène pour des applications de luminescence bleue ou verte

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US11598408P 2008-11-19 2008-11-19
US61/115,984 2008-11-19

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WO2010059837A2 true WO2010059837A2 (fr) 2010-05-27
WO2010059837A3 WO2010059837A3 (fr) 2010-07-22

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WO2013077141A1 (fr) 2011-11-25 2013-05-30 Jnc株式会社 Composé benzofluorène, matériau pour couche luminescente utilisant ledit composé et dispositif électroluminescent organique
US8531100B2 (en) 2008-12-22 2013-09-10 E I Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US9368728B2 (en) 2010-04-23 2016-06-14 Udc Ireland Limited Material for organic electroluminescence device, and organic electroluminescence device
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EP2449054A2 (fr) * 2009-07-01 2012-05-09 E. I. du Pont de Nemours and Company Composés de chrysène pour applications luminescentes
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US20110215715A1 (en) 2011-09-08
KR20110097847A (ko) 2011-08-31
JP2012509346A (ja) 2012-04-19
JP5687628B2 (ja) 2015-03-18
WO2010059837A3 (fr) 2010-07-22
CN102216417A (zh) 2011-10-12
EP2350230A4 (fr) 2012-08-22
EP2350230A2 (fr) 2011-08-03
KR101495396B1 (ko) 2015-02-24

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