Photoelectric conversion device and photoelectric conversion device dye, and compound

A compound of the structure represented by the following formula (IX):

• wherein:
• A is selected from the group consisting of the following formulas (IV) to (VII):
• wherein:
• S1 is an aromatic ring which may have a substituent, or a heterocyclic ring which may have a substituent;
• R17 to R20 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a halogen atom, or a cyano group;
• q is 0 or 1, and the substituent —Y1—COOH substitutes S1;
• wherein:
• S2 is an aromatic ring which may have a substituent, or a heterocyclic ring which may have a substituent;
• S3 is a sulfur atom or a structure represented by the following formula (Va);
• R21 to R23 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a halogen atom, or a cyano group;
• R24 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an anchor group;
• u is 0 or 1;
• and
• the substituent —Y1—COOH substitutes S2 and/or S3:
• wherein:
• R25 to R26 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a halogen atom, or a cyano group;
• R27 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an anchor group;
• R28 to R31 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, where R28 and R30 may each be eliminated to form an unsaturated bond, or R29 and R31 may be linked to form a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, or a phenanthrene ring which may have a substituent;
• t is 0 or 1;
• and
• the substituent —Y1—COOH substitutes S3;
• and
• wherein:
• R32 to R33 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms;
• and
• R34 to R41 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms;
• Z1 is any one divalent linking group selected from —CONR—, —NRCO—, —SO2NR—, and —NRSO2—;
• R in Z1 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms;
• D1 is a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, or a phenanthrene ring which may have a substituent;
• R1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkynyl group having 2 to 8 carbon atoms, each of which may be substituted by a halogen atom, a nitro group, a cyano group, an amino group, a hydroxyl group, an ether group, a carbonyl group, an aromatic ring, a heterocyclic ring, or a metallocenyl group;
• R42 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, a halogen atom, or a cyano group;
• X1 is an oxygen atom, a sulfur atom, a selenium atom, CR3R4, or NR5;
• R3 to R5 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkynyl group having 2 to 8 carbon atoms;
• R3 to R5 may each be independently substituted by a halogen atom, a nitro group, a cyano group, an amino group, a hydroxyl group, an ether group, a carbonyl group, an aromatic ring, a heterocyclic ring, or a metallocenyl group, and R3 and R4 may be linked to form an alicyclic group having a 3- to 6-membered ring;
• Y1 is an alkylene group having 1 to 8 carbon atoms, or a single bond;
• m is 0 to 2;
• Anb− is a b-valent anion;
• a is 1 or 2, and is a coefficient for keeping a charge of the entire dye neutral;
• and
• b is 1 or 2.

A photoelectric conversion device comprising a working electrode comprising a dye supported on a metal oxide layer, the dye being a compound of the structure represented by the following general formula (I):

• wherein:
• A is selected from the group consisting of the following formulas (IV) to (VII):
• wherein:
• S1 is an aromatic ring which may have a substituent, or a heterocyclic ring which may have a substituent;
• R17 to R20 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a halogen atom, or a cyano group;
• q is 0 or 1, and the substituent —Y1—COOH substitutes S1;
• wherein:
• S2 is an aromatic ring which may have a substituent, or a heterocyclic ring which may have a substituent;
• S3 is a sulfur atom or a structure represented by the following formula (Va);
• R21 to R23 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a halogen atom, or a cyano group;
• R24 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an anchor group;
• u is 0 or 1;
• and
• the substituent —Y1—COOH substitutes S2 and/or S3:
• wherein:
• R25 to R26 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a halogen atom, or a cyano group;
• R27 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an anchor group;
• R28 to R31 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, where R28 and R39 may each be eliminated to form an unsaturated bond, or R29 and R31 may be linked to form a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, or a phenanthrene ring which may have a substituent;
• t is 0 or 1;
• and
• the substituent —Y1—COOH substitutes S3;
• and
• wherein:
• R32 to R33 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms;
• and
• R34 to R41 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms;
• B comprises a cyanine skeleton having a maximum absorption wavelength λmax of 500 to 700 nm in a methanol solution;
• Z1 is a divalent linking group selected from —CONR—, —NRCO—, —SO2NR—, and —NRSO2—;
• R in Z1 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms;
• Y1 and Y2 are each independently an alkylene group having 1 to 8 carbon atoms, or a single bond;
• r is 1 or 2;
• m and n are each independently an integer of 0 to 2;
• and
• (m+n) is 1 or more.