Patent ID: 8101776
Filing Date: 2012-01-24
Classification: C07D,C09B,H01L

Abstract:
1. A semiconductor device comprising a bis(substituted ethynyl) compound with a tri- or polycyclic aromatic hydrocarbon backbone with heteroatoms wherein the rings that constitute the backbone are annealed to each other via not more than two commonly shared ring atoms, respectively, and the number of the common atoms of the vicinal rings is twice the number of the common side areas, with the proviso that the backbone together with the ethynyl groups have a point symmetry selected from the group consisting of the C 2h , the D 2h and the C s point symmetry group, which have the formula I wherein the ring labelled with A is an aromatic ring with 6 atoms, the ring marked B is a mono- or polycyclic unsaturated ring or ring system or annealed ferrocenobenzo of the subformula I(i) wherein the dotted bond marks the side of the benzo ring annealed to the central ring A in formula I, each annealed to ring A and the ring marked C is a mono- or polycyclic unsaturated ring or ring system or ferrocenobenzo of the subformula I(i) shown above, each annealed to ring A, each of rings or ring systems B and C may also carry a group ═S, ═O or ═C(NQ and wherein in at least one of the rings or ring systems B and C at least one ring atom is a heteroatom selected from N, NQ, O and S, if the first ring forming or forming part of ring or ring system B and C directly annealed to ring A has six ring atoms in both rings or ring systems B and C; where the rings or ring systems marked B and C in the compound of the formula I each contain at least one heteroatom, where the heteroatom or heteroatoms are selected from N, NQ, S and O; and each of the rings B and C is selected from the group consisting of the following moieties where the dotted bond marks the side of the ring or ring system annealed to the rest of the molecule: or ring C is selected from the preceding moieties, while ring B is of the formula Q is, for each occurrence of Q and each ring independently of the other, hydrogen or an unsubstituted or substituted hydrocarbyl, unsubstituted or substituted hydrocarbylcarbonyl or heteroaryl as defined below for X or Z; or Q is selected from hydrogen, C Z* and Z** are independently of each other selected from the group consisting of H, unsubstituted or substituted C two of the substitutents X, Y and Z present in formula I are substituted ethynyl wherein the substitutents are selected from the group consisting of unsubstituted or substituted hydrocarbyl with up to 40 carbon atoms, unsubstituted or substituted hydrocarbyloxy with up to 40 carbon atoms, hydrocarbylthio with up to 40 carbon atoms, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryloxy, unsubstituted or substituted heteroarylthio, cyano, carbamoyl, substituted amino, halo-C while the remaining substituents X, Y and/or Z, as far as present, are substitutents selected from the group consisting of unsubstituted or substituted C and each of n and p is 0 to 4 and m is 0 to 2, with the proviso that the sum of m, n and p is at least 2; or the bis(substituted ethynyl) compound is a compound selected from those of the formulae V or VI or is a compound of the formula I* or I**, wherein each R′ independently is selected from C R* is hydrogen or R′; and X and Z are substituted ethynyl as defined above.