Polyacene derivatives and production thereof

A polyacene derivative represented by general formula (I) below:

• 78
• (wherein:
• each of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, which may be the same or different, independently represents hydrogen atom;
• a C1-C40 hydrocarbon group which may optionally be substituted;
• a C1-C40 alkoxy group which may optionally be substituted;
• a C6-C40 aryloxy group which may optionally be substituted;
• an amino group which may optionally be substituted;
• a hydroxy group;
• or a silyl group which may optionally be substituted;
• provided that R6 and R7 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, and the saturated or unsaturated ring may be intervened by oxygen atom, sulfur atom or a group shown by formula:
• —N(R11)— (wherein R11 is hydrogen atom or a hydrocarbon group), or may optionally be substituted;
• each of A1 and A2, which may be the same or different, independently represents hydrogen atom;
• a halogen atom;
• a C1-C40 hydrocarbon group which may optionally be substituted;
• a C1-C40 alkoxy group which may optionally be substituted;
• a C6-C40 aryloxy group which may optionally be substituted;
• a C7-C40 alkylaryloxy group which may optionally be substituted;
• a C2-C40 alkoxycarbonyl group which may optionally be substituted;
• a C7-C40 aryloxycarbonyl group which may optionally be substituted;
• cyano group (—CN);
• carbamoyl group (—C(═O)NH2);
• a haloformyl group (—C(═O)—X, wherein X represents a halogen atom);
• formyl group (—C(═O)—H);
• isocyano group;
• isocyanate group;
• thiocyanate group or thioisocyanate group;
• provided that A1 and A2 may be cross-bridged with each other to form a ring shown by formula:
• —C(═O)—B—C(═O)— (wherein B is oxygen atom or a group shown by formula —N(B1)— (wherein B1 is hydrogen atom, a C1-C40 hydrocarbon group or a halogen atom));
• n is an integer of not less than 1;
• with proviso that, except for the case wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, A1 and A2 are all hydrogen atoms;
• when n is 1,
• at least R1, R2, R4 and R9 are groups other than hydrogen atom, or at least R3, R5, R8 and R10 are groups other than hydrogen atom;
• and,
• the cases of (a), (b), (c) and (d) below are excluded:
• (a) when R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, A1 and A2 are all methyl groups;
• (b) when R3, R4, R9 and R10 are all aryl groups that may optionally be substituted;
• (c) when R1, R2, R4 and R9 are all alkoxy or aryloxy groups, and R3, R5, R6, R7, R8, R10, A1 and A2 are all hydrogen atoms;
• (d) when R3, R5, R8 and R10 are all alkoxy or aryloxy groups, and R1, R2, R4, R6, R7, R9, A1 and A2 are all hydrogen atoms;
• and, when n is 2, the cases of (a′), (b′), (c′) and (d′) below are excluded:
• (a′) a pentacene derivative represented by formula (Ia) below:
• 79
• wherein R1, R2, R3, R4, R5a, R5b, R6, R7, R8a, R8b, R9, R10, A1 and A2 are all methyl groups;
• or R1, R2, R3, R4, R5a, R5b, R8a, R8b, R9 and R10 are all hydrogen atoms and at least one of R6, R7, A1 and A2 is an aryl group;
• or at least one of R1, R2, R3, R4, R5a, R5b, R6, R7, R8a, R8b, R9, R10, A1 and A2 is a diarylamine group;
• (b′) a pentacene derivative represented by formula (Ib) below:
• 80
• wherein R1, R2, R5b and R8b are all alkoxy or aryloxy groups;
• (c′) a pentacene derivative represented by formula (Ic) below:
• 81
• wherein at least 2 of R3, R5a, R8a and R10 are aryl or arylalkynyl groups;
• or at least one of R3, R5a, R8a and R10 is an arylalkenyl group;
• or R3, R5a, R8a and R10 are all alkoxy or aryloxy groups;
• (d′) a pentacene derivative represented by formula (Id) below:
• 82
• wherein R4 and R9 are hydrogen atom, a hydrocarbon group, an alkoxy group, an aryloxy group, a halogen atom or hydroxy group.