Light emitting devices and compositions

Abstract

A light emitting composition includes a light-emitting iridium-functionalized nanoparticle, such as an organic-inorganic light-emitting iridium-functionalized nanoparticle. A light emitting device includes an anode, a cathode, and a layer containing such a light-emitting composition. In an embodiment, the light emitting device can emit white light.

1 . A light emitting composition comprising one or more compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein: 
         core is a nanoparticle core; 
         n is 2; 
         X is a single bond or 
       
       
         
           
           
               
               
           
         
         each 
       
       
         
           
           
               
               
           
         
          is independently a first optionally substituted bidentate ligand; 
       
       
         
           
           
               
               
           
         
          is a second optionally substituted bidentate ligand selected from: 
       
       
         
           
           
               
               
           
         
       
       wherein m is an integer in the range of 1 to 9, p is an integer in the range or 1 to 20, z is 0, 1 or 2, R 1  is selected from alkyl, substituted alkyl, aryl and substituted aryl, R 2  is selected from: alkyl, substituted alkyl, aryl and substituted aryl, and * indicates a point of attachment of the second optionally substituted bidentate ligand to the core or X. 
     
     
         2 . The light-emitting composition of  claim 1 , the one or more compound of formula (I) further comprising at least one host attached to the core, wherein the at least one host comprises a hole transport material, an electron transport material or a mixture thereof. 
     
     
         3 . The light-emitting composition of  claim 2 , wherein the at least one host comprises 
       
         
           
           
               
               
           
         
       
       wherein k is 0 or an integer selected from 1 to 20 and each R 5  is independently selected from the following: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R is independently selected from H or alkyl, and * indicates a point of attachment. 
     
     
         4 . The light-emitting composition of  claim 1 , wherein the core comprises a moiety selected from the group consisting of a silsesquioxane, a cyclophosphazene, a triazine, a cyclodextrin, a calizarene, a phthalocyanine, and a silica particle. 
     
     
         5 . The light-emitting composition of  claim 4 , wherein the silsesquioxane comprises a 1,3,5,7,9,11,13,15-octakis(dimethylsilyloxy)pentacyclo-[9.5.1.13,9.15,15.17,13]-octasiloxane. 
     
     
         6 . The light-emitting composition of  claim 1 , wherein the first optionally substituted bidentate ligand is selected from: 
       
         
           
           
               
               
           
         
       
       and optionally substituted derivatives thereof, wherein indicates a point of attachment to the Ir. 
     
     
         7 . The light-emitting composition of  claim 6 , wherein the first optionally substituted bidentate ligand is a substituted derivative selected from: 
       
         
           
           
               
               
           
         
       
       wherein ‡ indicates a point of attachment to the Ir. 
     
     
         8 . The light emitting composition of  claim 1 , wherein the first bidentate ligand is selected from: 
       
         
           
           
               
               
           
         
       
       wherein ‡ indicates a point of attachment to the Ir. 
     
     
         9 . The light emitting composition of  claim 1 , wherein the first bidentate ligands are the same. 
     
     
         10 . The light emitting composition of  claim 1 , wherein the compound of formula (I) is selected from: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R 3  is the host having one of the following formulas 
       
         
           
           
               
               
           
         
       
       wherein k is 0 or an integer selected from 1 to 20, and R 5  can be selected from the following: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R is independently selected from H or alkyl, and * indicates a point of attachment. 
     
     
         11 . A light-emitting device comprising:
 an anode layer comprising a high work function metal;   a cathode layer comprising a low work function metal; and   a light-emitting layer comprising the light-emitting composition of  claim 1 , wherein the light-emitting layer is positioned between, and electrically connected to, the anode layer and the cathode layer.   
     
     
         12 . The light-emitting device of  claim 11 , wherein the light-emitting layer is configured to emit light selected from blue, green, orange, red and white. 
     
     
         13 . The light-emitting device of  claim 11 , wherein the light-emitting layer emits light having a CIE x-coordinate in the range of about 0.27 to about 0.30 and a CIE y-coordinate in the range of about 0.60 to about 0.65. 
     
     
         14 . The light-emitting device of  claim 11 , wherein the amount of the light-emitting composition in the light-emitting layer is in the range of from about 1% to about 99% by weight based on total weight of the light-emitting layer. 
     
     
         15 . The light-emitting device of  claim 11 , wherein the amount of the light-emitting composition in the light-emitting layer is in the range of from about 30% to about 70% by weight based on total weight of the light-emitting layer. 
     
     
         16 . The light-emitting device of  claim 11 , wherein the light-emitting layer further comprises a host material. 
     
     
         17 . The light-emitting device of  claim 16 , wherein the host material comprises an optionally substituted compound selected from: an aromatic-substituted amine, an aromatic-substituted phosphine, a thiophene, an oxadiazole, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), a triazole, 3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ), 3,4,5-Triphenyl-1,2,3-triazole, 3,5-Bis(4-tert-butyl-phenyl)-4-phenyl[1,2,4]triazole, an aromatic phenanthroline, 2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproine or BCP), 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline, a benzoxazole, a benzothiazole, a quinoline, aluminum tris(8-hydroxyquinolate) (Alq3), a pyridine, a dicyanoimidazole, cyano-substituted aromatic, 1,3,5-tris(2-N-phenylbenzimidazolyl)benzene (TPBI), 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), N,N′-bis(3-methylphenyl)N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (M14), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 1,1-Bis(4-bis(4-methylphenyl)aminophenyl)cyclohexane, a carbazole, 4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(9-vinylcarbazole) (PVK), N,N′N″-1,3,5-tricarbazoloylbenzene (tCP), a polythiophene, a benzidine, N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine, a triphenylamine, 4,4′,4″-Tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), a phenylenediamine, a polyacetylene, and a phthalocyanine metal complex. 
     
     
         18 . The light-emitting device of  claim 11 , wherein the high work function metal is selected from the group consisting of Au, Pt, indium-tin-oxide (ITO), and alloys thereof. 
     
     
         19 . The light-emitting device of  claim 11 , wherein the low work function metal is selected from the group consisting of Al, Ag, Mg, Ca, Cu, Mg/Ag, LiF/Al, CsF, CsF/Al, and alloys thereof. 
     
     
         20 . The light-emitting device of  claim 11 , wherein the anode layer has a thickness in the range of about 1 nm to about 1000 nm. 
     
     
         21 . The light-emitting device of  claim 11 , wherein the cathode layer has a thickness in the range of about 1 nm to about 1000 nm. 
     
     
         22 . The light-emitting device of  claim 11 , wherein the light-emitting layer has a thickness in the range of about 20 to about 150 nm. 
     
     
         23 . The light-emitting device of  claim 11 , further comprising an electron injection layer. 
     
     
         24 . The light-emitting device of  claim 23 , wherein the electron injection layer comprises an optionally substituted compound selected from: aluminum quinolate (Alq 3 ), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), phenanthroline, quinoxaline, 1,3,5-tris[N-phenylbenzimidazol-z-yl]benzene (TPBI) a triazine, a metal chelate of 8-hydroxyquinoline, tris(8-hydroxyquinoliate) aluminum, and a metal thioxinoid and bis(8-quinolinethiolato) zinc. 
     
     
         25 . The light-emitting device of  claim 11 , further comprising an electron transport layer. 
     
     
         26 . The light-emitting device of  claim 25 , wherein the electron transport layer comprises an optionally substituted compound selected from: aluminum tris(8-hydroxyquinolate) (Alq3), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis(N,N-t-butyl-phenyl)-1,3,4-oxadiazole (OXD-7), 3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole (TAZ), 2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproine or BCP), and 1,3,5-tris[2-N-phenylbenzimidazol-z-yl]benzene (TPBI). 
     
     
         27 . The light-emitting device of  claim 11 , further comprising a hole-blocking layer. 
     
     
         28 . The light-emitting device of  claim 27 , wherein the hole-blocking layer comprises an optionally substituted compound selected from: bathocuproine (BCP), 3,4,5-triphenyl-1,2,4-triazole, 3,5-bis(4-tert-butyl-phenyl)-4-phenyl-[1,2,4]triazole, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, and 1,1-bis(4-bis(4-methylphenyl)aminophenyl)cyclohexane. 
     
     
         29 . The light-emitting device of  claim 11 , further comprising an exciton blocking layer. 
     
     
         30 . The light-emitting device of  claim 29 , wherein the exciton blocking layer comprises an optionally substituted compound selected from: aluminum quinolate (Alq 3 ), 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), 4,4′-N,N′-dicarbazole-biphenyl (CBP), and bathocuproine (BCP). 
     
     
         31 . The light emitting device of  claim 11 , further comprising an hole transport layer. 
     
     
         32 . The light-emitting device of  claim 31 , wherein the hole transport layer comprises an optionally substituted compound selected from: 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), N,N′-bis(3-methylphenyl)N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (M14), 4,4′,4′-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), N,N′N″-1,3,5-tricarbazoloylbenzene (tCP), 4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(9-vinylcarbazole) (PVK), 3,4,5-Triphenyl-1,2,3-triazole, 3,5-Bis(4-tert-butyl-phenyl)-4-phenyl[1,2,4]triazole, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline, 1,1-Bis(4-bis(4-methylphenyl)aminophenyl)cyclohexane, a carbazole, a polythiophene, a benzidine, N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine, a triphenylamine, a phenylenediamine, 4,4′,4″-Tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, an oxadiazole, a polyacetylene and a phthalocyanine metal complex. 
     
     
         33 . The light-emitting device of  claim 11 , further comprising a hole injection layer. 
     
     
         34 . The light-emitting device of  claim 33 , wherein the hole injection layer comprises an optionally substituted compound selected from: a polythiophene. Poly(3,4-ethylenedioxythiophene (PEDOT)/polystyrene sulphonic acid (PSS), a benzidine, N,N,N′,N′-tetraphenylbenzidine, poly(N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine), a triphenylamine, a phenylenediamine. N′-bis(4-methylphenyl)-N,N′-bis(phenyl)-1,4-phenylenediamine, 4,4′,4″-tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, an oxadiazole, 3-bis(5-(4-diphenylamino)phenyl-1,3,4-oxadiazol-2-yl)benzene, a polyacetylene, poly(1,2-bis-benzylthio-acetylene), and phthalocyanine metal complex. 
     
     
         35 . A process of making the light-emitting device of  claim 11  comprising forming the light-emitting layer by a wet process. 
     
     
         36 . The process of  claim 35 , wherein the wet process is selected from the group consisting of spraying, spin coating, drop casting, inkjet printing, and screen printing. 
     
     
         37 . An iridium-functionalized nanoparticle represented by one of the following formulas: 
       
         
           
           
               
               
           
         
         wherein R′ is represented by 
       
       
         
           
           
               
               
           
         
          and R″ is represented by 
       
       
         
           
           
               
               
           
         
          wherein each 
       
       
         
           
           
               
               
           
         
          is independently a first optionally substituted bidentate ligand, and 
       
       
         
           
           
               
               
           
         
          is a second optionally substituted bidentate ligand; 
         R 3  is 
       
       
         
           
           
               
               
           
         
          wherein k is 0 or an integer selected from 1 to 20, and R 5  is independently selected from the following: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R is independently selected from H or alkyl, and * indicates a point of attachment in R 3 . 
     
     
         38 . The iridium-functionalized nanoparticle of  claim 37 , wherein 
       
         
           
           
               
               
           
         
       
       is selected from: 
       
         
           
           
               
               
           
         
       
       and optionally substituted derivatives thereof, wherein m is an integer in the range of 1 to 9, p is an integer in the range or 1 to 20, z is 0, 1 or 2, R 1  is selected from alkyl, substituted alkyl, aryl and substituted aryl, R 2  is selected from alkyl, substituted alkyl, aryl and substituted aryl, and * indicates a point of attachment to the Si. 
     
     
         39 . The iridium-functionalized nanoparticle of  claim 37 , wherein 
       
         
           
           
               
               
           
         
       
       is selected from 
       
         
           
           
               
               
           
         
       
       and optionally substituted derivatives thereof, wherein ‡ indicates a point of attachment to the Ir.