Light emitting devices and compositions

Abstract

A light emitting composition includes a light-emitting lumophore-functionalized nanoparticle, such as an organic-inorganic light-emitting lumophore-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 a compound of formula (I): 
     
       
         
         
             
             
         
       
       wherein: 
       core is a nanoparticle core; 
       A is a phosphorescent emitting lumophore; 
       B is a host; 
       L 1  and L 2  are each a linking group; 
       m is 0 or 1; 
       n is 0 or 1; 
       p is an integer in the range of 1 to 50; 
       q is an integer in the range of 1 to 50; 
       x is 0 or an integer in the range of 1 to 100, wherein for x≧2 each L 1  can be the same or different, and each A can be the same or different, and each p can be the same or different; and 
       y is an integer in the range of 1 to 100, wherein for y≧2 each L 2  can be the same or different, and each B can be the same or different, and each q can be the same or different. 
     
   
   
       2 . The light-emitting composition of  claim 1 , wherein the core is selected from the group consisting of a silsesquioxane, a cyclophosphazene, a triazine, a cyclodextrin, a calixarene, a phthalocyanine, and a silica particle. 
   
   
       3 . The light-emitting composition of  claim 2 , 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. 
   
   
       4 . The light-emitting composition of  claim 1 , wherein the phosphorescent emitter comprises a metal. 
   
   
       5 . The light-emitting composition of  claim 4 , wherein the metal is platinum. 
   
   
       6 . The light-emitting composition of  claim 4  wherein the phosphorescent emitter comprises an organometallic complex. 
   
   
       7 . The light-emitting composition of  claim 6 , wherein the organometallic complex comprises platinum. 
   
   
       8 . The lighting-emitting composition of  claim 7 , wherein the organometallic complex comprising platinum has the following structure: 
     
       
         
         
             
             
         
       
       wherein: 
       each R 1  is hydrogen or C 1-6  alkyl; 
       each R 2  is hydrogen or an electron-withdrawing group; 
       R 3 , R 4  and R 5  are each independently selected from the group consisting of hydrogen, an optionally substituted C 1-20  alkyl, optionally substituted C 2-20  alkenyl, optionally substituted C 2-20  alkynyl, optionally substituted C 5-30  aryl, and optionally substituted C 5-30  heteroaryl; 
       c is an integer in the range of 1 to 4; and 
       d is an integer in the range of 1 to 4; 
       provided that when m is 0 in Formula (I), at least one of R 1 , R 3 , R 4  and R 5  is a point of attachment to the core; or when m in Formula (I) is 1, at least one of R 1 , R 3 , R 4  and R 5  is a point of attachment to L 1 . 
     
   
   
       9 . The light-emitting composition of  claim 8 , wherein the phosphorescent emitter is selected from: 
     
       
         
         
             
             
         
       
     
     wherein * indicate the point of attachment to L 1  or the core. 
   
   
       10 . The light-emitting composition of  claim 1 , wherein the light emitting composition is a mixture comprising:
 an amount of a first compound of formula (I), wherein m=0, n=0, p=1, q=1, x=1 and y=7;   an amount of a second compound of formula (I), wherein m=0, n=0, p=1, q=1, x=2and y=6; and   an amount of a third compound having the structure:   
     
       
         
         
             
             
         
       
     
     wherein the core and B are as defined in formula (I). 
   
   
       11 . The light-emitting composition of  claim 10 , wherein the amount of the first compound of formula (I) is in the range of about 40 mole/mole % to about 60 mole/mole %; and the amount of the second compound of formula (I) is in the range of about 10 mole/mole % to about 30 mole/mole %. 
   
   
       12 . The light-emitting composition of  claim 1 , wherein the light emitting composition consisting essentially of a compound of formula (I), wherein m=0, n=0, p=1, q=1, x=1 and y=7. 
   
   
       13 . The light-emitting composition of  claim 1 , wherein the light emitting composition consisting essentially of a compound of formula (I), wherein m=0, n=0, p=1, q=1, x=2 and y=6. 
   
   
       14 . The light-emitting composition of  claim 1 , wherein the host is a group with a molecular weight (MW)<1000 g/mol. 
   
   
       15 . The light-emitting composition of  claim 14 , wherein the host comprises an optionally substituted moiety selected from the following group: aromatic-substituted amine, aromatic-substituted phosphine, carbazole, 3,6-disubstituted carbazole, thiophene, 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), 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, aromatic phenanthroline, 2,9-dimethyl-4,7-diphenyl-phenanthroline (bathocuproine or BCP), 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline, benzoxazole, benzothiazole, quinoline, aluminum tris(8-hydroxyquinolate) (Alq3), pyridine, 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, carbazole, 4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(9-vinylcarbazole) (PVK), N,N′N″-1,3,5-tricarbazoloylbenzene (tCP), polythiophene, benzidine, N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine, triphenylamine, 4,4′,4″-Tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), phenylenediamine, polyacetylene, and phthalocyanine metal complex. 
   
   
       16 . The lighting-emitting composition of  claim 14 , wherein the host is selected from: 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein R 1  is H or C 1-6  alkyl. 
   
   
       17 . The light-emitting composition of  claim 1 , wherein the host is an electron transport material. 
   
   
       18 . The light-emitting composition of  claim 17 , wherein the electron transport material is an optionally substituted compound selected from the following: 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). 
   
   
       19 . The light-emitting composition of  claim 1 , wherein the host is a hole transport material. 
   
   
       20 . The light-emitting composition of  claim 19 , wherein the hole transport material is an optionally substituted compound selected from the following: carbazole, 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, N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine, 4,4′,4″-Tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, and copper phthalocyanine. 
   
   
       21 . The light-emitting composition of  claim 1 , wherein L 1  and L 2  are each independently selected from C 1-30  alkyl, C 1-30  alkoxy, and 
     
       
         
         
             
             
         
       
     
   
   
       22 . The light-emitting composition of  claim 1 , wherein L 1  and L 2  each independently comprise a monovalent, divalent, a trivalent, a tetravalent, or a pentavalent moiety. 
   
   
       23 . The light-emitting composition of  claim 22 , wherein the divalent moiety is selected from the group consisting of: 
     
       
         
         
             
             
         
       
     
   
   
       24 . The light-emitting composition of  claim 22 , wherein the trivalent moiety is selected from the group consisting of: 
     
       
         
         
             
             
         
       
     
   
   
       25 . The light-emitting composition of  claim 22 , wherein the tetravalent moiety is: 
     
       
         
         
             
             
         
       
     
   
   
       26 . The light-emitting composition of  claim 22 , wherein the pentavalent moiety is selected from the group consisting of: 
     
       
         
         
             
             
         
       
     
   
   
       27 . The light-emitting composition of  claim 1 , wherein:
 the core is 1,3,5,7,9,11,13,15-octakis(dimethylsilyloxy)pentacyclo-[9.5.1.13,9.15,15.17,13]-octasiloxane;   A is   
     
       
         
         
             
             
         
       
     
     or 
     
       
         
         
             
             
         
       
     
     wherein * indicates the point of attachment to L 1  or the core;
 B is 
 
     
       
         
         
             
             
         
       
     
     or 
     
       
         
         
             
             
         
       
     
     wherein * indicates the point of attachment to L 2  or the core;
 L 1  is selected from C 1-6  alkyl; 
 L 2  is selected from C 1-6  alkyl and 
 
     
       
         
         
             
             
         
       
       m is 1; 
       n is 1; 
       p is 1; 
       q is 1 or 3; 
       x is 1, 2, 3 or 4; and 
       y is4, 5, 6 or 7. 
     
   
   
       28 . 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.   
   
   
       29 . The light-emitting device of  claim 28 , wherein the light-emitting layer is configured to emit white light. 
   
   
       30 . The light-emitting device of  claim 28 , wherein the light-emitting layer further comprises a second compound. 
   
   
       31 . The light-emitting device of  claim 30 , wherein the second compound is an electron transport material. 
   
   
       32 . The light-emitting device of  claim 31 , wherein the electron transport material is OXD-7. 
   
   
       33 . The light-emitting device of  claim 30 , wherein the second compound is an hole transport material. 
   
   
       34 . The light-emitting device of  claim 28 , wherein the light-emitting layer emits light having a CIE x-coordinate in the range of about 0.28 to about 0.50 and a CIE y-coordinate in the range of about 0.28 to about 0.50. 
   
   
       35 . The light-emitting device of  claim 28 , wherein the light-emitting layer emits light have a CRI value in the range of about 60 to about 100. 
   
   
       36 . The light-emitting device of  claim 28 , wherein the light-emitting layer emits light have a CRI value in the range of about 80 to about 100. 
   
   
       37 . The light-emitting device of  claim 28 , wherein the light-emitting layer emits light have a CRI value greater than 70. 
   
   
       38 . The light-emitting device of  claim 28 , wherein the high work function metal is selected from the group consisting of Au, Pt, indium-tin-oxide (ITO), and alloys thereof 
   
   
       39 . The light-emitting device of  claim 28 , 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. 
   
   
       40 . The light-emitting device of  claim 28 , wherein the anode layer has a thickness in the range of about 1 nm to about 1000 nm. 
   
   
       41 . The light-emitting device of  claim 28 , wherein the cathode layer has a thickness in the range of about 1 nm to about 1000 nm. 
   
   
       42 . The light-emitting device of  claim 28 , wherein the light-emitting layer has a thickness in the range of about 30 nm to about 250 nm. 
   
   
       43 . The light-emitting device of  claim 28 , further comprising an electron injection layer. 
   
   
       44 . The light-emitting device of  claim 43 , wherein the electron injection layer comprises an optionally substituted compound selected from: aluminum quinolate (Alq3), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), phenanthroline, quinoxaline, and 1,3,5-tris[N-phenylbenzimidazol-z-yl] benzene (TPBI). 
   
   
       45 . The light emitting device of  claim 28 , further comprising an electron transport layer. 
   
   
       46 . The light-emitting device of  claim 45 , 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). 
   
   
       47 . The light-emitting device of  claim 28 , further comprising a hole-blocking layer. 
   
   
       48 . The light-emitting device of  claim 47 , 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. 
   
   
       49 . The light-emitting device of  claim 28 , further comprising an exciton blocking layer. 
   
   
       50 . The light-emitting device of  claim 49 , wherein the exciton blocking layer comprises an optionally substituted compound selected from: aluminum quinolate (Alq3), 4,4′-bis[N-(naphthyl)-N-phenyl-amino]biphenyl (α-NPD), 4,4′-N,N′-dicarbazole-biphenyl (CBP), and bathocuproine (BCP). 
   
   
       51 . The light emitting device of  claim 28 , further comprising an hole transport layer. 
   
   
       52 . The light-emitting device of  claim 51 , 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, carbazole, polythiophene, benzidine, N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine, triphenylamine, phenylenediamine, 4,4′,4″-Tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, oxadiazole, polyacetylene and phthalocyanine metal complex. 
   
   
       53 . The light-emitting device of  claim 28 , further comprising a hole injection layer. 
   
   
       54 . The light-emitting device of  claim 53 , wherein the hole injection layer comprises an optionally substituted compound selected from: polythiophene. polytheylenedioxythiophene (PEDOT)/polystyrene sulphonic acid (PSS), benzidine, N,N,N′,N′-tetraphenylbenzidine, poly(N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine), triphenylamine, phenylenediamine. N′-bis(4-methylphenyl)-N,N′-bis(phenyl)-1,4-phenylenediamine, 4,4′,4″-tris(N-(naphthylen-2-yl)-N-phenylamino)triphenylamine, oxadiazole, 3-bis(5-(4-diphenylamino)phenyl-1,3,4-oxadiazol-2-yl)benzene, polyacetylene, ly(1,2-bis-benzylthio-acetylene), and phthalocyanine metal complex. 
   
   
       55 . A process of making the light-emitting device of  claim 28  comprising forming the light-emitting layer by a wet process. 
   
   
       56 . The process of  claim 55 , wherein the wet process is selected from the group consisting of spraying, spin coating, drop casting, inkjet printing, and screen printing.