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US 9,806,266 B2Granted
Salts of phosphorus oxide as N-dopants for organic electronics
AssigneeSiemens Aktiengesellschaft
InventorsAndreas Kanitz, Günter Schmid, Jan Hauke Wemken
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Abstract
An organic electronic component contains a substrate, a first electrode, a second electrode and at least one electron transport layer between the first and second electrode. The electron transport layer is a salt-like derivative of a phosphorus oxo compound as n-dopant.
Claims5
An organic electronic component comprising:
- a substrate;
- first and second electrodes;
- and at least one electron-conducting layer, disposed between the first and second electrodes, including a salt-type derivative of a phosphorus oxo compound having an n-dopant as follows
- where X, Y are greater than 0 and not greater than 3;
- n, m are integers greater than 0 and less than 4;
- M is a metal and R1=O1, S, Se, O—R, S—R, Se—R and R2=R, O—R, S—R, Se—R, and R is selected from the group consisting of substituted and unsubstituted alkyl, long-chain alkyl, cycloalkyl, haloalkyl, aryl, arylene, haloaryl, heteroaryl, heteroarylene, heterocycloalkylene, heterocycloalkyl, haloheteroaryl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl;
- and
- wherein the salt-type derivative of a phosphorus oxo salt is one of a cesium salt and a rubidium salt of a compound selected from the group consisting of:
- 6,7,11,12,19,20,24,25-octahydrodibenzo[g,r]-[1,3,6,9,12,14,17,20,2,13]-octaoxadiphosphacyclodocosine-9,22-diol 9,22-dioxide:
- (4R)-22-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide;
- 8,9-diphenyldiphenanthro[4,3-d:3,4-f][1,3,2]dioxaphosphepin-18-ol 18-oxide;
- 2,6-bis(triphenylsiyl)dinaphtho[2,1-d:1,2-f][1,3,2]dioxaphosphepin-4-ol 4-oxide;
- 1-butyl-3-methylimidazolium dibutylphosphate and corresponding di(C1-C10)alkyl derivatives;
- diphenyl hydrogenphosphate;
- bis(4-nitrophenyl) hydrogenphosphate;
- 2-naphthyl 4-[(E)-phenyldiazenyl]phenylhydrogenphosphate;
- dinaphtho[2,1-d:1,2-f][1,3,2]dioxaphosphepin-4-ol 4-oxide;
- (R)-3,3′-bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diylhydrogenphosphate;
- (S)-3,3′-bis(2,4,6-triisopropyl-phenyl)-1,1′-binaphthyl-2,2′-diylhydrogenphosphate;
- 18-hydroxy-8,9-diphenyldiphenanthro[4,3-d:3′,4′-f][1,3,2]-dioxaphosphepin 18-oxide;
- (IIbR)-4-hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d:1′,2′f]-1,3,2-dioxaphosphepin 4-oxide;
- (R)-(−)-3,3′-bis(triphenylsilyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate;
- lithium carbamoylphosphate;
- D-myo-inositol 1-monophosphate;
- 6-benzoyl-2-naphthyl phosphate;
- 4-nitrophenyl phosphate bis(cyclohexylammonium) salt;
- Naphthol AS phosphate;
- Naphthol AS-X phosphate;
- 4-tert-pentyl)phenyl phosphate;
- geranylgeranyl pyrophosphate;
- Naphthol AS phosphate;
- methyl phosphonate;
- trichloromethyl phosphonate;
- heptane-1,7-diyldiphosphonate;
- (heptylsulfanyl)methyl phosphonate;
- 1-hydroxybutyl phosphonate;
- 2-phenylethyl phosphonate;
- butylhydrogentrichloromethyl phosphonate;
- 4-methoxyphenyl phosphonate;
- 3-phenylpropyl phosphonate;
- dimethylallyl phosphonate;
- 1-aminopentane-1,1-diyl diphosphonate;
- 4-iodobenzyl phosphonate;
- ((2-cyanoethyl)-phosphonomethylamino)acetate;
- 4-ethoxyphenyl phosphonate;
- (+−)-2-amino-4-phosphonobutanate;
- glyphosate 3-13C[(phosphonomethyl)amino]acetate;
- amino(phenyl)methyl phosphonate;
- 3-(carboxymethylphosphonomethylamino)-propionate;
- D-(−)-2-amino-5-phosphonopentanate;
- 2-amino-7-phosphonoheptanate;
- tetramethyl 2-oxopropane-1,3-diyl diphosphonate;
- 2-methoxybenzyl phosphonate;
- tetraethylmethylene diphosphonate;
- diethyl methoxymethyl-phosphonate;
- methyl 6-[hydroxy(isopropoxy)phosphoryl]-hexanoate;
- ((2-cyanoethyl)(hydroxymethoxyphosphoryl-methyl)amino)acetate;
- dipropylchloromethylphosphonate;
- amino[4-(trifluoromethyl)phenyl]methylphosphonate;
- and [(4-chlorobenzyl)amino]methylphosphonate.
57 more elements
Dependencies are inferred from the claim text.