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    • 6. 发明申请
    • CATHODE COATING
    • WO2008012581A3
    • 2008-01-31
    • PCT/GB2007/050447
    • 2007-07-26
    • OLED-T LIMITEDGANESHAMURUGAN, SubramaniamKATHIRGAMANATHAN, PoopathySURENDRAKUMAR, SivagnanasundramRAVICHANDRAN, SeenivasagamCHAN, Yun, Fu
    • GANESHAMURUGAN, SubramaniamKATHIRGAMANATHAN, PoopathySURENDRAKUMAR, SivagnanasundramRAVICHANDRAN, SeenivasagamCHAN, Yun, Fu
    • H01L51/54
    • Embodiments of electroluminescent devices of the invention are preferably formed of a transparent anode; a layer of a hole transporting material; a layer of an electroluminescent material; a layer of an electron transporting material; a layer of lithium quinolate or of a substituted lithium quinolate e.g. of thickness less than 7 nm; and a metal cathode. The layer of the metal quinolate is preferably about 0.3-0.5 nm in thickness. In an embodiment there is provided an organic light-emitting diode having a cathode, an electron injection layer in contact with the cathode and an electron transport layer in contact with the electron injection layer and comprising aluminium, zirconium or hafnium quinolate or a mixture thereof or a mixture of any of them with a quinolate of a metal of group 1, 2, 3, 13 or 14 of the periodic table, wherein the electron injection layer comprises lithium quinolate or a substituted lithium quinolate having one or more substituents selected from C 1 -C 4 alkyl, monocyclic aryl or aralk-(C 1 -C 4 )-yl, aryloxy or fluoro subject to the proviso that not more than one substituent is C 2 -C 4 alkyl, aralkyl or aryloxy or an oligomer thereof, and wherein the electrode is of aluminium. Such devices may be made by a method including the steps of forming lithium quinolate or a substituted lithium quinolate having one or more substituents selected from C 1 -C 4 alkyl, monocyclic aryl or aralk-(C 1 -C 4 )-yl, aryloxy or fluoro subject to the proviso that not more than one substituent is C 2 -C 4 alkyl, aralkyl or aryloxy by reacting a lithium alkyl or alkoxide with 8-hydroxyquinoline or a derivative thereof in a solvent comprising acetonitrile, and depositing lithium quinolate or a substituted lithium quinolate formed as described above on a cathode of the device to provide an electron injection layer.
    • 8. 发明申请
    • COMPOUNDS HAVING ELECTROLUMINESCENT OR ELECTRON TRANSPORT PROPERTIES
    • 具有电致发光或电子传输特性的化合物
    • WO2009112854A1
    • 2009-09-17
    • PCT/GB2009/050180
    • 2009-02-24
    • MERCK PATENT GMBHKATHIRGAMANATHAN, PoopathySURENDRAKUMAR, Sivagnanasundram
    • KATHIRGAMANATHAN, PoopathySURENDRAKUMAR, Sivagnanasundram
    • C07D215/04C07D215/12C07D409/14C09K11/00H01L51/00
    • C07D215/12C07D215/04C07D409/14C09K11/06C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/185H01L51/0035H01L51/0036H01L51/0038H01L51/0042H01L51/005H01L51/0052H01L51/0053H01L51/0059H01L51/0078H01L51/0079H01L51/0085H01L51/5048H01L51/5088H05B33/14
    • A compound of the formula R 1 (CR 3 =CR 4 ) nAr(CR 4 =CR 3 ) n R 2 wherein: n is 0 or 1; Ar represents aryl or heteroaryl having 1-5 aromatic rings which may be chain or fused or a combination of chain and fused, which may be substituted withalkoxy, fluoro, fluoroalkyl or cyano and which in the case of a 5-memnered ring nitrogen heteroatom may be N-substituted with aryl or substituted aryl optionally further substituted with alkoxy, fluoro, fluoroalkyl or cyano; R 1 and R 2 independently represent aryl or nitrogen, oxygen or sulphur-containing heteroaryl having two to four fused aromatic rings one of which may be 5-membered and optionally substituted by aryl or heteroaryl having 1-5 chain or fused aromatic rings which may be further substituted withalkoxy, fluoro, fluoroalkyl or cyano; and R 3 and R 4 independently represent hydrogen, methyl, ethyl or benzyl. Alsoprovided is a method of making a compound having electroluminescent and/or electroconductive properties, which comprises condensing an aromatic dialdehyde with a methyl-substituted heteroaryl compound having two to four fused rings which maybe unsubstituted ormay be further substituted by aryl or heteroaryl having from one to fouraromatic rings, said aryl or heteroaryl substituent or substituents optionally being substituted with one or more fluoro, fluoroalkyl orcyano substituents.The condensation may be carried out in acetic anhydride under reflux. The compounds may be incorporatede.g. as an electron transport layer into an optical light emitting diode,where embodiments can provide high electron mobility, low turn-on voltage and good lifetime,or into an electrostatic imaging member. Acompositionis provided comprising a compound as above and a second host or electron transport material and/or at leastone dopant.
    • 式R1(CR3 = CR4)nAr(CR4 = CR3)nR2的化合物其中:n为0或1; Ar表示可以是链或稠合的具有1-5个芳环或芳基或稠合的芳基或杂芳基,其可以被烷氧基,氟,氟代烷基或氰基取代,并且在5-烯键环氮杂原子的情况下 被任选进一步被烷氧基,氟,氟烷基或氰基取代的芳基或取代芳基取代; R 1和R 2独立地表示芳基或氮,具有2至4个稠合芳环的氧或含硫杂芳基,其中一个可以是5元并且任选地被具有1-5个链或稠合芳环的芳基或杂芳基取代, 被烷氧基,氟,氟烷基或氰基取代; 并且R 3和R 4独立地表示氢,甲基,乙基或苄基。 还提供了制备具有电致发光和/或导电性质的化合物的方法,其包括将芳族二醛与具有2-4个稠合环的甲基取代的杂芳基化合物缩合,所述稠环可以是未取代的或可以进一步被芳基或杂芳基取代, 四芳环,所述芳基或杂芳基取代基或任选被一个或多个氟,氟代烷基氰基取代基取代的取代基。缩合可以在乙酸酐中回流进行。 可以混合化合物。 作为电子传输层进入光发射二极管,其中实施例可以提供高电子迁移率,低导通电压和良好的寿命,或者进入静电成像构件。 提供的组合物包含如上所述的化合物和第二主体或电子传输材料和/或至少一种掺杂剂。