P-doping cross-linking of organic hole transporters

A method for producing hole-transporting electrical layers, the method comprising:

• providing a substrate;
• providing at least one crosslinking reagent;
• and
• reacting a functionalized organic matrix compound with the at least one crosslinking reagent on the substrate to form compounds of relatively high molecular mass,
• wherein the functionalized organic matrix compound conforms to formula 1:
• where:
• L is a bond or is selected from the group consisting of substituted or nonsubstituted, saturated or unsaturated C1-C50 alkyl, aryl, polyethylene glycol, polyethylenediamine, polyester, polyurethane, polyvinylidenephenyl chains, and mixtures thereof;
• E1, E2 independently of one another may be oxygen, sulfur, selenium, NH or NE3,
• optionally E3, wherein E3 is selected from the group consisting of substituted or nonsubstituted alkyl and aryl, and E3 is bound to R as follows:
• R is selected from the group consisting of H, D, C1-C10 alkyl-silyl or aryl-silyl esters, fluorinated or nonfluorinated branched or unbranched C1-C10 alkyl, aryl, and heteroaryl,
• RHTL is selected from the group consisting of C20-C200 triarylamine-based hole transporters, thiophene-containing derivatives thereof, and mixtures thereof, and
• the crosslinking reagent comprises at least one metal atom from groups 13-15 and at least one organic ligand.

A method for producing hole-transporting electrical layers, the method comprising:

• providing a substrate;
• providing at least one crosslinking reagent;
• and
• reacting a functionalized organic matrix compound with the at least one crosslinking reagent on the substrate to form compounds of relatively high molecular mass,
• wherein the functionalized organic matrix compound conforms to formula 1:
• where:
• L is a bond or is selected from the group consisting of substituted or nonsubstituted, saturated or unsaturated C1-C50 alkyl, aryl, polyethylene glycol, polyethylenediamine, polyester, polyurethane, polyvinylidenephenyl chains, and mixtures thereof;
• E1, E2 independently of one another may be oxygen, sulfur, selenium, NH or NE3,
• optionally E3, wherein E3 is selected from the group consisting of substituted or nonsubstituted alkyl and aryl, and E3 is bound to R as follows:
• R is selected from the group consisting of H, D, C1-C10 alkyl-silyl or aryl-silyl esters, fluorinated or nonfluorinated branched or unbranched C1-C10 alkyl, aryl, and heteroaryl,
• RHTL is a substituted compound functionalized with at least one compound selected from the group consisting of
• NPB (N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)benzidine),
• β-NPB (N,N′-bis(naphthalen-2-yl)-N,N′-bis(phenyl)benzidine),
• TPD (N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine),
• Spiro TPD (N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine),
• Spiro-NPB (N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-spiro),
• DMFL-TPD (N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-dimethylfluorene),
• DMFL-NPB (N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-dimethylfluorene),
• DPFL-TPD (N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-diphenylfluorene),
• DPFL-NPB (N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-diphenylfluorene),
• Spiro-TAD (2,2′,7,7′-tetrakis(N,N-diphenylamino)-9,9′-spirobifluorene),
• 9,9-bis[4-(N,N-bisbiphenyl-4-ylamino)phenyl]-9H-fluorene,
• 9,9-bis[4-(N,N-bisnaphthalen-2-ylamino)phenyl]-9H-fluorene,
• 9,9-bis[4-(N,N′-bisnaphthalen-2-yl-N,N′-bisphenylamino)phenyl]-9H-fluorene,
• N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)benzidine,
• 2,7-bis[N,N-bis(9,9-spirobifluoren-2-yl)amino]-9,9-spirobifluorene,
• 2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spirobifluorene,
• 2,2′-bis(N,N-diphenylamino)-9,9-spirobifluorene,
• di[4-(N,N-ditolylamino)phenyl]cyclohexane,
• 2,2′,7,7′-tetra(N,N-ditolyl)aminospirobifluorene,
• N,N,N′,N′-tetranaphthalen-2-ylbenzidine and mixtures thereof, and
• the crosslinking reagent comprises at least one metal atom from groups 13-15 and at least one organic ligand;
• wherein the crosslinking reagent and the organic matrix compound are reacted on the substrate using a temperature treatment in a range of greater than or equal to 50° C. and less than or equal to 300° C.