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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
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
  • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• • 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
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  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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  • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
  • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
  • H05B33/14—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
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  • 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
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  • 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
  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
• • 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
  • H10K85/30—Coordination compounds
  • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
  • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
• • 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

Definitions

• Ichinosawa et al. in JP 2003/146951 and JP 2004/091334, describe anthracene materials substituted with phenylene diamine groups in the 2,6 positions that are useful as hole-transporting materials for EL devices and provide examples of their use in a layer adjacent to the LEL.
• Toshio et al. in JP 1995/109449, provides examples of anthracene- type materials substituted with tertiary amine groups and their use as light- emitting materials without being incorporated into an LEL host material. It is known that having a single component LEL generally results in low efficiencies and short lifetimes.
• an OLED device having high luminous efficiency, excellent operational lifetime and also having excellent color purity.
• an OLED device comprising a cathode, an anode, and having therebetween a light-emitting layer wherein the light-emitting layer comprises (a) a 2-arylanthracene compound and (b) a light- emitting second anthracene compound having amino substitution at a minimum of two positions, wherein at least one amine is substituted at the 2 position.
• FIG. 1 shows a cross-section of an OLED device of this invention.
• the OLED device of this invention is typically provided over a supporting substrate where either the cathode or anode can be in contact with the substrate.
• the electrode in contact with the substrate is conveniently referred to as the bottom electrode.
• the bottom electrode is the anode, but this invention is not limited to that configuration.
• Hole-Iniecting Layer While not always necessary, it is often useful that a hole-injecting layer 105 be provided between anode 103 and hole-transporting layer 107.
• the hole-injecting layer can be formed of a single or a mixture of organic or inorganic materials.
• the hole-injecting layer may be divided into several layers, with each layer being composed of either the same or different materials.
• the hole-injecting material can serve to improve the film formation property of subsequent organic layers and to facilitate injection of holes into the hole-transporting layer.
• Suitable materials for use in the hole-injecting layer include, but are not limited to porphyrin and phthalocyanine compounds as described in U.S.
• the HIL may include an inorganic compound(s), such as metal oxide, metal nitride, metal carbide, a complex of a metal ion and organic ligands, and a complex of a transition metal ion and organic ligands.
• an inorganic compound(s) such as metal oxide, metal nitride, metal carbide, a complex of a metal ion and organic ligands, and a complex of a transition metal ion and organic ligands.
• N,N'-Bis(N",N"-diphenylaminonaphthalen-5-yl)-N,N'-diphenyl-l,5- diaminonaphthalene (CAS 503624-47-3);
• N,N'-Bis(4-(2,2-diphenylethen- 1 -yl)phenyl)-N,N'-bis(4- methylphenyl)benzidine (CAS 263746-29-8); N,N t -Bis(phenyl)-N,N'-bis(4'-(N,N-bis(naphth-l-yl)amino)biphenyl-4- yl)benzidine;
• An important relationship for choosing an emitting material is a comparison of the bandgap potential which is defined as the energy difference between the highest occupied molecular orbital and the lowest unoccupied molecular orbital of the molecule.
• the band gap of the dopant is smaller than that of the host material.
• di and d 3 -d 8 may be the same or different and each represents hydrogen or an independently selected substituent and each g may be the same or different and each represents an independently selected substituent, provided that two substituents may combine to form a ring group and p, r, and s are independently 0-
• di, d 3 -d 5 and d 7 -d 8 may be the same or different and each represents hydrogen or an independently selected substituent and each h may be the same or different and each represents an independently selected substituent, provided that two substituents may combine to form a ring group and a-f, and j are independently 0-5.
• the light-emitting second anthracene compound (b) is represented by formula [7],
• the substituent may be, for example, halogen, such as chloro, bromo or fluoro; nitro; hydroxyl; cyano; carboxyl; or groups which may be further substituted, such as alkyl, including straight or branched chain or cyclic alkyl, such as methyl, trifluoromethyl, ethyl, t-butyl, 3-(2,4-di-t-pentylphenoxy) propyl, and tetradecyl; alkenyl, such as ethylene, 2-butene; alkoxy, such as methoxy, ethoxy, propoxy, butoxy, 2-methoxyethoxy, sec-butoxy, hexyloxy, 2-ethylhexyloxy, tetradecyloxy, 2-(2,4-di-t-pentylphenoxy)ethoxy, and 2-dodecyloxyethoxy; aryl such as phenyl, 4-t-butylphenyl
• CO-2 Magnesium bisoxine [alias, bis(8-quinolinolato)magnesium(II)]
• CO-3 Bis[benzo ⁇ f ⁇ -8-quinolinolato]zinc (II)
• CO-4 Bis(2-methyl-8-quinolinolato)aluminum(III)- ⁇ -oxo-bis(2-methyl-8- quinolinolato) aluminum(III)
• CO-5 Indium trisoxine [alias, tris(8-quinolinolato)indium]
• CO-6 Aluminum tris(5-methyloxine) [alias, tris(5-methyl-8-quinolinolato) aluminum(III)]
• Patent Application 11/289,856 by Klubek et al. wherein the electron-transporting layer includes a compound comprising one and only one anthracene nucleus and including no more than two phenanthroline-containing substituents and wherein said nucleus is substituted in the 2-, 3-, 6-, or 7-position with a phenanthroline-containing substituent.
• Useful phenanthroline compounds are also more fully described in U.S.
• the mixed electron-transporting layer includes a 1 :1 mixture of Bphen, (also known as 4,7-diphenyl-l,10-phenanthroline) and AlQ 3 .
• Useful mixed electron-transporting layers are further described by commonly assigned U.S. Serial Nos. 11/076,821 ; 11/077,218; and 11/116,096 wherein the electron-transporting layer is formed by mixing a first compound with a second compound that is a low voltage electron-transporting material, to form a layer on the cathode side of the emitting layer in an OLED device, which gives an OLED device that has a drive voltage even lower than that of the device with only the low voltage electron-transporting material.
• a metallic material based on a metal having a work function less than 4.2 eV is included in the layer.
• the electron-transporting layer can be doped with low work-function alkaline metals or alkaline earth metals, such as Li, Cs, Ca, or Mg.
• the alkali metal is Li.
• the alkali metal is Cs.
• the electron-transporting layer can be doped with electron-injecting materials that are described below.
• the ETL contains a hydrocarbon material, that is, a material composed of only carbon and hydrogen atoms, for example, 9,10-di-2- naphthalenyl-2-phenylanthracene, it is often beneficial to incorporate an electron- injecting-layer (EIL) as described below.
• EIL electron- injecting-layer
• Electron-Injecting Layer (EIL)
• the LUMO energy level of the EIL compound is equal to or nearly the same as the LUMO energy level of the material contained in the ETL.
• the LUMO energy level of the EIL compound is equal to or more positive than the LUMO energy level of the ETL material.
• the difference in LUMO energy levels of the EIL compound and the ETL material is 0.50 or less, 0.40 or less, 0.30 or less, 0.20 or less or even 0.10 eV or less.
• the compound in the EIL has a LUMO energy value equal to or more positive than the LUMO energy value of the compound in the ETL.
• the relative thickness of the EIL to that of the LEL is important.
• the ratio of the thickness of the EIL to LEL should be greater than 0.125. Desirably this ratio is 0.25 or greater, or even 0.50 or greater. In one embodiment, the ratio of the thickness of the EIL to LEL is in the range of 0.125 to 1.50 or desirably in the range of 0.125 to 1.25.
• the EIL includes a heterocyclic compound.
• Metal chelates Li chelates in particular, are useful electron- injecting materials as more fully described in U.S. Patent Applications, 11/258,671; 1 1/259,586; 11/259,290; 11/501,336; 11/258,740; 11/258,719.
• Metal chelates that do not contain the 8-hydroxyquinolate ligand are also useful as electron-injecting layers, such as described in U.S. Patent Application 11/259,290 and 11/501,336 by Begley et al., wherein the electron- injecting layer contains a cyclometallated complex represented by formula (C)
• Z and the dashed arc represent two or three atoms and the bonds necessary to complete a 5- or 6-membered ring with M; each A represents H or a substituent and each B represents an independently selected substituent on the Z atoms, provided that two or more substituents may combine to form a fused ring or a fused ring system; j is 0-3 and k is 1 or 2;
• the cathode When light emission is viewed through the cathode, the cathode must be transparent or nearly transparent. For such applications, metals must be thin or one must use transparent conductive oxides, or a combination of these materials.
• Optically transparent cathodes have been described in more detail in US 4,885,211, US 5,247,190, JP 3,234,963, US 5,703,436, US 5,608,287, US 5,837,391, US 5,677,572, US 5,776,622, US 5,776,623, US 5,714,838, US 5,969,474, US 5,739,545, US 5,981,306, US 6,137,223, US 6,140,763, US
• Example 4 The synthesis of N,N'-di-2-naphthalenyl-N,N',9,10-tetraphenyl-2,6- anthracenediamine (Inv-BlO).
• Ehomo is the HOMO energy taken from a B3LYP/MIDI! geometry optimization using the PQS computer code (PQS v3.2, Parallel Quantum Solutions, Fayetteville, Arkansas).
• the calculated oxidation potential of Inv-B122 was found to be 0.1 V less than that of Inv-Bl and is estimated to be 0.58 V vs. SCE.
• Comparative Device 1 -2 was prepared in the same manner as Device 1-1 except that Inv-A5 was replaced with CX-I, and Inv-Bl was present at 5.9% by volume.
• a ⁇ 1.1 mm thick glass substrate coated with a transparent ITO conductive layer was cleaned and dried using a commercial glass scrubber tool.
• the thickness of ITO is about 25 ran and the sheet resistance of the ITO is about 68 ⁇ /square.
• the ITO surface was subsequently treated with oxidative plasma to condition the surface as an anode.
• a layer of CFx, 1 ran thick, was deposited on the clean ITO surface by decomposing CHF 3 gas in an RF plasma treatment chamber. The substrate was then transferred into a vacuum deposition chamber for deposition of all other layers on top of the substrate.
• the following layers were deposited in the following sequence by sublimation from heated boats under a vacuum of approximately 10 6 Torn a) a 110 nm hole-transporting layer including NPB; b) a 40 nm light-emitting layer including Inv-A5 as host and Inv-Bl as the light-emitting dopant (5.9% by volume); c) a 25 nm electron-transporting layer OfAlQ 3 ; d) a 0.5 nm electron-injecting layer of lithium fluoride; e) a 100 nm cathode of aluminum.
• Inventive Device 2-2 was prepared in the same manner as Device
• Inventive Device 2-3 was prepared in the same manner as Device
• Devices 2-1, 2-2, and 2-3 were tested for luminance and chromaticity (CIE x, y ) at a constant current of 20 mA/cm 2 .
• Device lifetime which is the time required for the initial luminance to drop by 50%, was measured at room temperature using a DC current of 80 mA/cm 2 and device performance results are reported in Table 3.
• the device was encapsulated in a nitrogen atmosphere along with calcium sulfate as a desiccant.
• Example 10 Fabrication of Devices 4-1, 4-2, and 4-3.
• Inventive EL device 2- 1 satisfying the requirements of the invention, was constructed in the following manner:
• Devices 4-1, 4-2, and 4-3 were tested for luminance and chromaticity (CIE x, y ) at a constant current of 20 mA/cm 2 .
• Device lifetime which is the time required for the initial luminance to drop by 50%, was measured at room temperature using an initial luminance of 10,000 cd/m 2 and device performance results are reported in Table 5.
• Comparative Device 5-2 was prepared in the same manner as Device 5-1 except that the following layers were deposited in the following sequence by sublimation from heated boats under a vacuum of approximately 10 ⁇ 6 Torn a) a 110 nm hole-transporting layer including NPB; b) a 20 nm light-emitting layer including Inv-A5 as host and Inv-Bl as the light-emitting dopant (6% by volume); c) a 35 nm electron-transporting layer of In v- A5; d) a 10 nm electron-injecting layer of PH-I (EIL); e) a 0.5 nm further electron-injecting layer of MC-3 (EIL-2); f) a 100 nm cathode of aluminum.
• EIL PH-I
• EIL-2 a 0.5 nm further electron-injecting layer of MC-3
• layer d) was omitted and the following layers were deposited in the following sequence by sublimation from heated boats under a vacuum of approximately 10 "6 Torn a) a 110 nm hole-transporting layer including NPB; b) a 20 nm light-emitting layer including Inv-A5 as host and Inv-Bl as the light-emitting dopant (6% by volume); c) a 45 nm electron-transporting layer of Inv-A5; e) a 2.0 nm further electron-injecting layer of MC-3 (EIL-2); f) a 100 nm cathode of aluminum.
• Comparative Device 5-6 was prepared in the same manner as Device 5-5 except that layer e) was omitted.

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