Doped conjugated polymers, devices, and methods of making devices

Abstract

Use of certain materials in hole injection or hole transport layers can improve the operational lifetimes in organic electronic devices. Compositions comprising a doped conjugated polymer, doped with a redox dopant, including iodonium salt, can increase lifetimes. Inks can be formulated and cast as films in organic electronic devices including OLEDs, PHOLEDs, and OPVs. One embodiment provides a composition with a conjugated polymer doped with a redox dopant. Non-aqueous based inks can be formulated. Iodonium salts can be used.

1 .- 72 . (canceled) 
     
     
         73 . A composition comprising (i) poly(3,4-di-polyether)-thiophene doped with at least one redox dopant, wherein the two polyether moieties are each an independent substitution and do not form a ring together, and each polyether moiety includes three, four, five, or six oxygen atoms in the moiety, and wherein the polyether moieties are branched moieties, and (ii) a non-aqueous solvent. 
     
     
         74 . The composition of  claim 73 , wherein the composition further comprises a synthetic polymer different from the poly(3,4-di-polyether)-thiophene. 
     
     
         75 . The composition of  claim 73 , wherein the composition further comprises a planarizing agent. 
     
     
         76 . The composition of  claim 73 , wherein the composition further comprises a planarizing agent, wherein the planarizing agent comprises a polymer comprising optionally substituted fused aromatic rings or optionally substituted polycyclic aromatic hydrocarbon side groups. 
     
     
         77 . The composition of  claim 73 , wherein the composition comprises about 25 wt. % to about 99 wt. % of poly(3,4-di-polyether)-thiophene and about 1 wt. % to about 75 wt. % redox dopant, wherein wt. % is with respect to the total amount of poly(3,4-di-polyether)-thiophene and the redox dopant. 
     
     
         78 . The composition of  claim 73 , wherein the amount of redox dopant is about 0.01 m/ru to about 1 m/ru, wherein m is the molar amount of the redox dopant and ru is the molar amount of poly(3,4-di-polyether)-thiophene repeat unit. 
     
     
         79 . The composition of  claim 73 , wherein the non-aqueous solvent is an aprotic organic solvent. 
     
     
         80 . The composition of  claim 73 , wherein the non-aqueous solvent is a non-halogenated solvent. 
     
     
         81 . The composition of  claim 73 , wherein the non-aqueous solvent is selected from ethers, ethylene glycol monoether acetates, propylene glycol monoether acetates, aliphatic ketones, and aromatic ketones. 
     
     
         82 . The composition of  claim 73 , wherein the poly(3,4-di-polyether)-thiophene is soluble in tetrahydrofuran, chloroform, alkylated benzenes, halogenated benzenes, NMP, DMF, DMAc, DMSO, methyl ethyl ketone, cyclohexanone, chloroform, dichloromethane, acetone, THF, dioxanes, ethyl acetate, ethyl benzoate, ethylene carbonate, propylene carbonate, 1,2-dimethoxy ethane, tetrahydropyran, or anisole. 
     
     
         83 . The composition of  claim 73 , wherein the composition is formulated for use as a hole injection or hole transport layer in an organic electronic device. 
     
     
         84 . The composition of  claim 73 , wherein the composition is heated after mixing the poly(3,4-di-polyether)-thiophene and redox dopant. 
     
     
         85 . The composition of  claim 73 , wherein the dopant comprises an anion which comprises fluorine, and the composition is substantially free of any additional perfluorinated material. 
     
     
         86 . The composition of  claim 73 , wherein each polyether moiety includes three oxygen atoms in the moiety. 
     
     
         87 . A device comprising at least one layer prepared with the composition of  claim 73 . 
     
     
         88 . The device of  claim 87  wherein the layer is a hole injection layer or a hole transport layer or hole extraction layer. 
     
     
         89 . The device of  claim 87 , wherein the device is an organic electronic device. 
     
     
         90 . The device of  claim 87 , wherein the device is an OLED, a PHOLED, or a photovoltaic device. 
     
     
         91 . The device of  claim 87 , wherein the composition is a coating on an electrode. 
     
     
         92 . The device of  claim 87 , wherein the device is a PHOLED device with a lifetime at t50 of at least 1400 hours.