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US 8,709,299 B2Granted
Dye sensitised solar cell
AssigneeBASF SE
InventorsJunichi Tanabe, Hiroshi Yamamoto, Shinji Nakamichi, Ryuichi Takahashi
Life of this patent
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Abstract
The present invention pertains to an electrode layer comprising a porous film made of oxide semiconductor fine particles sensitized with certain methin dyes. Moreover the present invention pertains to a photoelectric conversion device comprising said electrode layer, a dye sensitized solar cell comprising said photoelectric conversion device and to novel methin dyes.
Claims16
An electrode layer, comprising:
- a porous film comprising oxide semiconductor fine particles sensitized with a dye of formula (I):
- wherein
- n is 1-6,
- R1 and R2 are each independently H, a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, or a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups, and additionally R1 is optionally D,
- A is a group of formula (II) or (III):
- wherein
- Y− is an inorganic anion or an organic anion,
- R29 is a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, O−, OR32, a C7-C20 aralkyl, a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups, or a C7-C20 aralkyl substituted at the aryl with a 1-3 C1-C8 alkyl groups,
- R30 is G, H, OR32, a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, or a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups,
- R31 is H or
- R32 is a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, or a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups,
- G is —R28—COOH, —R28—COO−Z+;
- —R28—SO3H, —R28—SO3−Z+;
- —R28—OP(O)(O−Z+)2, —R28—OP(O)(OH)2, or —R28—OP(O)(OH)O−Z+,
- wherein
- R28 is a direct bond, a C1-C20 alkylene, a C2-C4 alkenylene, or a C6-C10 arylene,
- Z+ is an organic or inorganic cation,
- each D is independently a group of formula (III) or (IV),
- wherein
- R17 and R18 are each independently an optionally substituted moiety selected from the group consisting of a C1-C20 alkyl, a C2-C20 alkenyl, a C2-C20 alkynyl, a C6-C20 aryl, a C4-C24 heteroaryl, a C7-C20 aralkyl, a C8-C20 aralkenyl, a C8-C20 aralkynyl, a C4-C20 cycloalkyl, a C5-C20 cycloalkenyl, and a C6-C20 cycloalkynyl, wherein the alkyl and cycloalkyl are optionally interrupted with at least one selected from the group consisting of O, S, and NR14, or
- at least one selected from the group consisting of (i) R17 and R18, (ii) R17 and R22, (iii) R17 and R20, and (iv) R18 and R19 form together an optionally substituted 5-, 6-, or 7-membered ring,
- R15, R16, R19, R20, R21, R22, R23, and R24 are each independently H, NR25R26, OR25, SR25, NR25—NR26R27, NR25—OR26, O—CO—R25, O—CO—OR25, O—CO—NR25R26, NR25—CO—R26, NR25—CO—OR26, NR25—CO—NR26R27, CO—R25, CO—OR25, CO—NR25R26, S—CO—R25, CO—SR25, CO—NR25—NR26R27, CO—NR25—OR26, CO—O—CO—R25, CO—O—O—CO—OR25, CO—O—CO—NR25R26, CO—NR25—CO—R26, CO—NR25—CO—OR26, or an optionally substitute moiety selected from the group consisting of a C1-C20 alkyl, a C6-C20 aryl, a C2-C20 alkenyl, a C2-C20 alkynyl, a C6-C20 aryl, a C4-C20 heteroaryl, a C7-C20 aralkyl, a C8-C20 aralkenyl, a C8-C20 aralkynyl, a C4-C20 cycloalkyl, a C8-C20 cycloalkenyl, and a C6-C20 cycloalkynyl, wherein the alkyl and cycloalkyl are optionally interrupted with at least one selected from the group consisting of O, S, and NR14,
- R25, R26, and R27 are each independently H or an optionally substituted moiety selected from the group consisting of a C1-C20 alkyl, a C6-C20 aryl, a C2-C20 alkenyl, a C2-C20 alkynyl, a C6-C20 aryl, a C4-C20 heteroaryl, a C7-C20 aralkyl, a C8-C20 aralkenyl, a C8-C20 aralkynyl, a C4-C20 cycloalkyl, a C5-C20 cycloalkenyl, and a C6-C20 cycloalkynyl, wherein the alkyl and cycloalkyl are optionally interrupted with at least one selected from the group consisting of O, S, and NR14, and
- R14 is H or a C1-C20 alkyl.
21 more elements
A compound, having a formula (I):
- wherein
- n is 1-6,
- R1 and R2 are each independently H, a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, or a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups, and additionally R1 is optionally D,
- A is a group of formula (II) or (III):
- wherein
- Y− is an inorganic anion or an organic anion,
- R29 is a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, O−, OR32, a C7-C20 aralkyl, a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups, or a C7-C20 aralkyl substituted at the aryl with a 1-3 C1-C8 alkyl groups,
- R30 is G, H, OR32, a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, or a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups,
- R31 is H or
- R32 is a C1-C20 alkyl optionally interrupted with at least one selected from the group consisting of O, S, and NR14, a C6-C20 aryl, a C4-C20 heteroaryl, or a C6-C20 aryl substituted with 1-3 C1-C8 alkyl groups,
- G is —R28—COOH, —R28—COO−Z+;
- —R28—SO3−H, —R28—SO3−Z+;
- —R28—OP(O)(O−Z+)2, —R28—OP(O)(OH)2, or —R28—OP(O)(OH)O−Z+,
- R28 is a direct bond, a C1-C20 alkylene, a C2-C4 alkenylene, or a C6-C10 arylene,
- Z+ is an organic or inorganic cation,
- each D is independently a group of formula (III) or (IV),
- wherein
- R17 and R18 are each independently an optionally substituted moiety selected from the group consisting of a C1-C20 alkyl, a C2-C20 alkenyl, a C2-C20 alkynyl, a C6-C20 aryl, a C4-C24 heteroaryl, a C7-C20 aralkyl, a C8-C20 aralkenyl, a C8-C20 aralkynyl, a C4-C20 cycloalkyl, a C5-C20 cycloalkenyl, and a C6-C20 cycloalkynyl, wherein the alkyl and cycloalkyl are optionally interrupted with at least one selected from the group consisting of O, S, and NR14, or
- at least one selected from the group consisting of (i) R17 and R18, (ii) R17 and R22, (iii) R17 and R20, and (iv) R18 and R19 form together an optionally substituted 5-, 6-, or 7-membered ring,
- R15, R16, R19, R20, R21, R22, R23, and R24 are each independently H, NR25R26, OR25, SR25, NR25—NR26R27, NR25−OR26, O—CO—R25, O—CO—OR25, O—CO—NR25R26, NR25—CO—R26, NR25—CO—OR26, NR25—CO—NR26R27, CO—R25, CO—OR25, CO—NR25R26, S—CO—R25, CO—SR25, CO—NR25—NR26R27, CO—NR25—OR26, CO—O—CO—R25, CO—O—CO—R25, CO—O—CO—NR25R26, CO—NR25—CO—R26, CO—NR25—CO—OR26, or an optionally substitute moiety selected from the group consisting of a C1-C20 alkyl, a C6-C20 aryl, a C2-C20 alkenyl, a C2-C20 alkynyl, a C6-C20 aryl, a C4-C20 heteroaryl, a C7-C20 aralkyl, a C8-C20 aralkenyl, a C8-C20 aralkynyl, a C4-C20 cycloalkyl, a C5-C20 cycloalkenyl, and a C6-C20 cycloalkynyl, wherein the alkyl and cycloalkyl are optionally interrupted with at least one selected from the group consisting of O, S, and NR14,
- R25, R26, and R27 are each independently H or an optionally substituted moiety selected from the group consisting of a C1-C20 alkyl, a C6-C20 aryl, a C2-C20 alkenyl, a C2-C20 alkynyl, a C6-C20 aryl, a C4-C20 heteroaryl, a C7-C20 aralkyl, a C8-C20 aralkenyl, a C8-C20 aralkynyl, a C4-C20 cycloalkyl, a C5-C20 cycloalkenyl, and a C6-C20 cycloalkynyl, wherein the alkyl and cycloalkyl are optionally interrupted with at least one selected from the group consisting of O, S, and NR14, and
- R14 is H or a C1-C20 alkyl.
19 more elements
Dependencies are inferred from the claim text.