Method of producing a metal phthalocyanine compound, and method of producing a phthalocyanine compound and an analogue thereof

A method of producing a phthalocyanine compound represented by formula (13) or (14), or a phthalocyanine analogue, comprising:

• conducting a reaction of a compound represented by formula (11), in the presence of a dehydrating agent and an ammonium salt compound in combination, thereby producing the phthalocyanine compound represented by formula (13) or (14), or the phthalocyanine analogue:
• wherein Z represents an organic moiety for forming a 6-membered aromatic ring structure together with the two carbon atoms bonded to the Z;
• wherein Z has the same meaning as defined in formulae (11);
• M1 and M2 each independently represent an atom in the Group 1 of the periodic table;
• and M3 represents a metal atom or a metal compound thereof, except an atom in the Group 1 of the periodic table.

A method of producing a phthalocyanine compound represented by formula (13) or (14), or a phthalocyanine analogue, comprising:

• conducting a reaction of a phthalonitrile compound represented by formula (15), in the presence of a dehydrating agent and an ammonium salt compound in combination, thereby producing the phthalocyanine compound represented by formula (13) or (14), or the phthalocyanine analogue:
• wherein R′ represents a hydrogen atom or a substituent;
• n′ represents an integer of 1 to 4;
• and when n′ is 2 to 4, a plurality of R′s may be the same or different from each other or may be bonded to each other to form a ring;
• wherein Z represents an organic moiety for forming a 6-membered aromatic ring structure together with the two carbon atoms bonded to the Z;
• M1 and M2 each independently represent an atom in the Group 1 of the periodic table;
• and M3 represents a metal atom or a metal compound thereof, except an atom in the Group 1 of the periodic table.