Hydroxygallium porphyrazine derivative mixture and electrophotographic photoconductor
A hydroxygallium porphyrazine derivative mixture including: a plurality of different hydroxygallium porphyrazine derivatives each represented by the following General Formula (A-2): where A 1 , A 2 , A 3 , A 4 , B 1 , B 2 , B 3 and B 4 each independently represent a nitrogen atom or a carbon atom bonded to hydrogen, with the proviso that both of A 1 and B 1 are carbon atoms each bonded to hydrogen or only one of A 1 and B 1 is a nitrogen atom, both of A 2 and B 2 are carbon atoms each bonded to hydrogen or only one of A 2 and B 2 is a nitrogen atom, both of A 3 and B 3 are carbon atoms each bonded to hydrogen or only one of A 3 and B 3 is a nitrogen atom, and both of A 4 and B 4 are carbon atoms each bonded to hydrogen or only one of A 4 and B 4 is a nitrogen atom.
1. A hydroxygallium porphyrazine derivative mixture comprising:
a plurality of different hydroxygallium porphyrazine derivatives each represented by the following General Formula (B-21):
where A, B, C and D each independently represent a group selected from the group consisting of: an unsubstituted benzo group; a benzo group which may have as a substituent a halogen atom, an alkyl group, a hydroxyl group or a benzo group; an unsubstituted pyrido group; and a pyrido group which may have a substituent a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group.
2. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein the hydroxygallium porphyrazine derivative mixture is obtained by treating with an acid a gallium porphyrazine derivative mixture containing a plurality of gallium porphyrazine derivatives each represented by the following General Formula (B-20), the gallium porphyrazine derivative mixture being obtained by reacting together at least one selected from the group consisting of compounds represented by the following General Formulas (B-1) to (B-6), at least one selected from the group consisting of compounds represented by the following General Formulas (B-7) to (B-18), and a gallium compound represented by the following General Formula (B-19):
in each of the General Formulas (B-1) to (B-6), R 1 represents a halogen atom, an alkyl group, a hydroxyl group or a benzo group, and m is an integer of 0 to 4, where when m is an integer of 2 or greater, R 1 s may be identical or different,
in each of the General Formulas (B-7) to (B-18), R 2 represents a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group, and n is an integer of 0 to 3, where when n is an integer of 2 or greater, R 2 s may be identical or different,
Ga (R 3 ) 3 General Formula (B-19)
where R 3 represents a halogen atom or an alkoxy group,
where A, B, C and D each independently represent a group selected from the group consisting of: an unsubstituted benzo group; a benzo group which may have as a substituent a halogen atom, an alkyl group, a hydroxyl group or a benzo group; an unsubstituted pyrido group; and a pyrido group which may have a substituent a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group, and R 3 represents an halogen atom or an alkoxy group.
3. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein the hydroxygallium porphyrazine derivative mixture comprises: a hydroxygallium phthalocyanine derivative represented by General Formula (B-21) where A, B, C and D each represent a benzo group which may have a substituent; and a plurality of different hydroxygallium porphyrazine derivatives each represented by General Formula (B-21) where at least one of A, B, C and D represents a pyrido group which may have a substituent.
4. The hydroxygallium porphyrazine derivative mixture of claim 3 , wherein the hydroxygallium porphyrazine derivative mixture is obtained by treating with an acid a gallium porphyrazine derivative mixture containing: a gallium phthalocyanine derivative represented by the following General Formula (B-20) where A, B, C and D each represent a benzo group which may have a substituent; and a plurality of different gallium porphyrazine derivatives each represented by the following General Formula (B-20) where at least one of A, B, C and D represents a pyrido group which may have a substituent, the gallium porphyrazine derivative mixture being obtained by reacting together at least one selected from the group consisting of compounds represented by the following General Formulas (B-1) to (B-6), at least one selected from the group consisting of compounds represented by the following General Formulas (B-7) to (B-18), and a gallium compound represented by the following General Formula (B-19):
in each of the General Formulas (B-1) to (B-6), R 1 represents a halogen atom, an alkyl group, a hydroxyl group or a benzo group, and m is an integer of 0 to 4, where when m is an integer of 2 or greater, Ws may be identical or different,
in each of the General Formulas (B-7) to (B-18), R 2 represents a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group, and n is an integer of 0 to 3, where when n is an integer of 2 or greater, R 2 s may be identical or different,
Ga(R 3 ) 3 General Formula (B-19)
where R 3 represents a halogen atom or an alkoxy group,
where A, B, C and D each independently represent a group selected from the group consisting of: an unsubstituted benzo group; a benzo group which may have as a substituent a halogen atom, an alkyl group, a hydroxyl group or a benzo group; an unsubstituted pyrido group; and a pyrido group which may have a substituent a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group, and R 3 represents an halogen atom or an alkoxy group.
5. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein the hydroxygallium porphyrazine derivative mixture has diffraction peaks at Bragg angles (2θ±0.2°) of at least 7.4°, 16.2°, 25.2° and 28.3° in an X ray diffraction spectrum obtained using CuKα rays.
6. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein in General Formula (B-21), the unsubstituted benzo group or the benzo group which may have as a substituent a halogen atom, an alkyl group, a hydroxyl group or a benzo group is a benzo group having a hydroxyl group.
7. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein in General Formula (B-21), the unsubstituted pyrido group or the pyrido group which may have as a substituent a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group is a pyrido group having an alkyl group.
8. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein in General Formula (B-21), the unsubstituted pyrido group or the pyrido group which may have as a substituent a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group is a pyrido group having a halogen atom.
9. The hydroxygallium porphyrazine derivative mixture of claim 1 , wherein in General Formula (B-21), the unsubstituted pyrido group or the pyrido group which may have as a substituent a nitro group, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group or a benzo group is a pyrido group having a benzo group.