6,13-dihalogen-5,14-dihydropentacene derivative and method for producing 6,13-substituted-5,14-dihydropentacene derivative using same

A method for producing a 6,13-substituted 5,14-dihydropentacene derivative represented by the following formula (II):

• [wherein A1 and A2, which may be the same or different, are each independently an optionally substituted C1-C20 hydrocarbon group;
• an optionally substituted heteroaryl group;
• an optionally substituted C1-C20 alkoxy group;
• an optionally substituted C6-C20 aryloxy group;
• an optionally substituted C1-C20 alkoxycarbonyl group;
• an optionally substituted C6-C20 aryloxycarbonyl group;
• an optionally substituted carbamoyl group;
• an optionally substituted amino group or an optionally substituted silyl group, wherein if the hydrocarbon group, the heteroaryl group, the alkoxy group, the aryloxy group, the alkoxycarbonyl group, the aryloxycarbonyl group, the carbamoyl group, the amino group or the silyl group has a substituent(s), the substituent(s) is/are selected from the group consisting of a C1-C10 hydrocarbon group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a hydroxyl group, a halogen atom and a silyl group, and
• R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, which may be the same or different, are each independently a hydrogen atom;
• an optionally substituted C1-C20 hydrocarbon group;
• an optionally substituted C1-C20 alkoxy group;
• an optionally substituted C6-C20 aryloxy group;
• an optionally substituted C1-C20 alkoxycarbonyl group;
• an optionally substituted C6-C20 aryloxycarbonyl group;
• an optionally substituted carbamoyl group;
• an optionally substituted amino group or an optionally substituted silyl group, wherein if the hydrocarbon group, the alkoxy group, the aryloxy group, the alkoxycarbonyl group, the aryloxycarbonyl group, the carbamoyl group, the amino group or the silyl group has a substituent(s), the substituent(s) is/are selected from the group consisting of a C1-C10 hydrocarbon group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a hydroxyl group, a halogen atom and a silyl group],
• said method comprising the step of reacting a 6,13-dihalogen-5,14-dihydropentacene derivative represented by the following formula (I):
• [wherein X1 and X2, which may be the same or different, are each independently a halogen atom, and R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are the same as defined in formula (II)] with an organometallic compound comprising A1 or A2 as defined in formula (II) in the presence of a transition metal catalyst.

A complex compound represented by the following formula (IV):

• [wherein X1 and X2, which may be the same or different, are each independently a halogen atom, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, which may be the same or different, are each independently a hydrogen atom;
• an optionally substituted C1-C20 hydrocarbon group;
• an optionally substituted C1-C20 alkoxy group;
• an optionally substituted C6-C20 aryloxy group;
• an optionally substituted C1-C20 alkoxycarbonyl group;
• an optionally substituted C6-C20 aryloxycarbonyl group;
• an optionally substituted carbamoyl group;
• an optionally substituted amino group or an optionally substituted silyl group, wherein if the hydrocarbon group, the alkoxy group, the aryloxy group, the alkoxycarbonyl group, the aryloxycarbonyl group, the carbamoyl group, the amino group or the silyl group has a substituent(s), the substituent(s) is/are selected from the group consisting of a C1-C10 hydrocarbon group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a hydroxyl group, a halogen atom and a silyl group, and Ra and Rb, which may be the same or different, are each independently an optionally substituted C1-C20 alkyl group or an optionally substituted C6-C20 aryl group].

A method for producing a 6,13-substituted 5,14-dihydropentacene derivative represented by the following formula (II):

• [wherein A1 and A2, which may be the same or different, are each independently an optionally substituted C1-C20 hydrocarbon group;
• an optionally substituted heteroaryl group;
• an optionally substituted C1-C20 alkoxy group;
• an optionally substituted C6-C20 aryloxy group;
• an optionally substituted C1-C20 alkoxycarbonyl group;
• an optionally substituted C6-C20 aryloxycarbonyl group;
• an optionally substituted carbamoyl group;
• an optionally substituted amino group or an optionally substituted silyl group, wherein if the hydrocarbon group, the heteroaryl group, the alkoxy group, the aryloxy group, the alkoxycarbonyl group, the aryloxycarbonyl group, the carbamoyl group, the amino group or the silyl group has a substituent(s), the substituent(s) is/are selected from the group consisting of a C1-C10 hydrocarbon group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a hydroxyl group, a halogen atom and a silyl group, and
• R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, which may be the same or different, are each independently a hydrogen atom;
• an optionally substituted C1-C20 hydrocarbon group;
• an optionally substituted C1-C20 alkoxy group;
• an optionally substituted C6-C20 aryloxy group;
• an optionally substituted C1-C20 alkoxycarbonyl group;
• an optionally substituted C6-C20 aryloxycarbonyl group;
• an optionally substituted carbamoyl group;
• an optionally substituted amino group or an optionally substituted silyl group, wherein if the hydrocarbon group, the alkoxy group, the aryloxy group, the alkoxycarbonyl group, the aryloxycarbonyl group, the carbamoyl group, the amino group or the silyl group has a substituent(s), the substituent(s) is/are selected from the group consisting of a C1-C10 hydrocarbon group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a hydroxyl group, a halogen atom and a silyl group],
• said method comprising the step of reacting a complex compound represented by the following formula (IV):
• [wherein X1 and X2, which may be the same or different, are each independently a halogen atom, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are the same as defined in formula (II), and Ra and Rb, which may be the same or different, are each independently an optionally substituted C1-C20 alkyl group or an optionally substituted C6-C20 aryl group] with an organometallic compound comprising A1 or A2 as defined in formula (II).