Salts of phosphorus oxide as N-dopants for organic electronics

Patent metadata

Field	Value
Publication number	US-9806266-B2
Application number	US-201314431238-A
Country	US
Kind code	B2
Filing date	Sep 11, 2013
Priority date	Sep 27, 2012
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

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.

First claim

The invention claimed is:

1. 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 R 1 =O 1 , 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.

2. The organic electronic component as claimed in claim 1 , wherein the salt-type derivative of the phosphorus oxo compounds is present in the electron-conducting layer in a layer thickness concentration of at least 0.01% and not greater than 50%.

3. The organic electronic component as claimed in claim 1 , wherein the salt-type derivative of the phosphorus oxo compound has a molecular weight of at least 70 g/mol and not greater than 1000 g/mol, and a sublimation temperature of at least 120° C. and not greater than 1200° C.

4. The organic electronic component as claimed in claim 1 , wherein the salt-type derivative of the phosphorus oxo compounds is present in the electron-conducting layer in a layer thickness concentration of at least 0.01% and not greater than 50%.

5. The organic electronic component as claimed in claim 1 , wherein the organic electronic component is disposed within one of an organic solar cell, an organic transistor, a light-emitting organic component, an organic light-emitting diode and an organic light-emitting electrochemical cell.

Assignees

• Siemens Ag

Inventors

• Kanitz Andreas
• Schmid Günter
• Wemken Jan Hauke

Classifications

• H01L51/5076

  Electricity · mapped topic

• H01L51/0558

  Electricity · mapped topic

• H01L51/441

  Electricity · mapped topic

• H01L51/0022

  Electricity · mapped topic

• H01L51/5203

  Electricity · mapped topic