Asymmetric phenanthrolins, method for their manufacture and doped organic semiconductor material containing them

Asymmetrically substituted phenanthroline compounds (I), are new. Asymmetrically substituted phenanthroline compounds of formula (I), are new. R 1>, R 2>optionally substituted (hetero)aryl, alkyl of formula CH(R) 2or C(R) 3; R : 1-20C-alkyl; R 3>H, optionally substituted (hetero)aryl, or 1-20C-alkyl; R 4>H, optionally substituted (hetero)aryl, 1-20C-alkyl, 3-20C-cycloalkyl, NH 2, NHR 0>or N(R 0>) 2; R 0>optionally substituted (hetero)aryl, 1-20C-alkyl, cycloalkyl, cyclic amine, carbazolyl, dibenzazepinyl, O-alkyl or O-aryl; and R 5>optionally substituted 1-20C-alkyl, 3-20C-cycloalkyl, optionally substituted (hetero)aryl, CN, COOalkyl, COaryl or COalkyl. Independent claims are included for: (1) the preparation of (I); (2) a doped organic semiconductor comprising at least an organic matrix material, which is doped with a dopant and the matrix material contains (I); and (3) a 5,6-dihydrophene anthroline compound of formula (V). [Image] [Image].