Platinum complex for use as sensitizer for semiconductor...

Details Platinum complex for use as sensitizer for semiconductor... Platinum complex for use as sensitizer for semiconductor...

2000-03-27

2001-08-14

Diamond, Alan (Department: 1753)

Batteries: thermoelectric and photoelectric

Photoelectric

Cells

C136S252000, C429S111000, C429S212000, C429S213000, C257S040000, C257S428000, C257S431000, C257S439000, C556S136000, C556S137000, C544S225000, C546S002000, C546S008000, C546S010000

Reexamination Certificate

active

06274806

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a platinum complex useful for sensitizing an oxide semiconductor electrode of a solar cell. The present invention is also directed to an electrode using the above platinum complex sensitizer and to a solar cell using such an electrode.
With a view toward improving efficiency in conversion of photoenergy into electric energy, many attempts have been hitherto made to expand sensible region of a semiconductor electrode. One known method is dye sensitization. Known sensitizers which are generally ruthenium complexes, however, are not fully satisfactory from the standpoint of practical use.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a novel platinum complex useful as a sensitizer for an oxide semiconductor electrode of a solar cell.
Another object of the present invention is to provide a platinum complex sensitizer which can absorb light of a visible region and which has a high efficiency of conversion of photo energy to electric energy.
It is a further object of the present invention to provide a dye-sensitized oxide semiconductor electrode useful for a solar cell.
It is a further object of the present invention to provide a solar cell using the above solar cell.
In accomplishing the foregoing object there is provided in accordance with the present invention a platinum complex represented by the following formula (1):
PtL
1
L
2
  (1)
wherein
L
1
represents a ligand selected from the group consisting of 2,2′-bipyridine compounds having at least one anionic group and 1,10-phenanthroline compounds having at least one anionic group and
L
2
represents a dithiolate selected from the group consisting of those represented by the following formulas (a) through (d):
wherein R represents an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an aminoalkyl group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a cyano group or a hydrogen atom,
wherein R represents an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an aminoalkyl group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a cyano group or a hydrogen atom,
wherein R and R
1
represent, independently from each other, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an aminoalkyl group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a cyano group or a hydrogen atom,
wherein R and R
1
represent, independently from each other, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an aminoalkyl group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a cyano group or a hydrogen atom.
The present invention also provides a platinum complex represented by the following formula (2):
PtLX
1
X
2
  (2)
wherein
L represents a ligand selected from the group consisting of 2,2′-bipyridine compounds having at least one anionic group and 1,10-phenanthroline compounds having at least one anionic group and
X
1
and X
2
represent, independently from each other, a thiolate selected from the group consisting of those represented by the following formulas (e) and (f):
.S—R  (e)
wherein R represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an aminoalkyl group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a cyano group or a hydrogen atom,
.S—Ar  (f)
wherein Ar represents a substituted or non-substituted aryl group having 6 to 10 carbon atoms.
The present invention further provides a dye-sensitized electrode comprising a substrate having an electrically conductive surface, an oxide superconductor film formed on said conductive surface, and the above platinum complex supported on said film.
The present invention further provides a solar cell comprising the above electrode, a counter electrode, and an electrolyte disposed therebetween.
Other objects, features and advantages of the present invention will become apparent from the detailed description of the preferred embodiments of the invention to follow.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS OF THE INVENTION
In the platinum complex of the formula (1), L
1
represents a ligand selected from 2,2′-bipyridine compounds having at least one anionic group and 1,10-phenanthroline compounds having at least one anionic group. The anionic group may be, for example, a carboxyl group, a sulfonic acid group or phosphoric acid group. The anionic group may be a free acid group or its neutral salt group neutralized with a salt forming anion such as an alkali metal ion (e.g. Na or K ion) or ammonium ion. The number of the anionic groups contained in the ligand L
1
is at least one, preferably at least two. The number of the anionic groups is generally 4 (four) at maximum.
Examples of 2,2′-bipyridine compounds having at least one anionic group may be those represented by the following formula (3):
wherein Y
1
and Y
2
stands, independently from each other, for an anionic group, R
1
and R
2
stands, independently from each other, for a substituent which may be, for example, an alkyl group having 1 to 4 carbon atoms, a halogen atom such as chlorine, bromine, iodine or fluorine or a halogenated alkyl group having 1 to 4 carbon atoms, m and n are integers of 0 to 4, preferably 1 to 2, and p and q are integers of 0 to 6, preferably 0 to 2. A total of m and n is preferably 1 to 6, more preferably 2.
Illustrative of the bipyridine compounds are 2,2′-bipyridine-4,4′-dicarboxylic acid, 2,2′-bipyridine-4,4′-disulfonic acid, 2,2′-bipyridine-4,4′-diphosphoric acid, 2,2′-bipyridine-5,5′-dimethyl-4,4′-dicarboxylic acid, 2,2′-bipyridine-5,5′-dimethyl-4,4′-disulfonic acid and 2,2′-bipyridine-5,5′-dimethyl-4,4′-diphosphoric acid.
Examples of 1,10-phenanthroline compounds having at least one anionic group may be those represented by the following formula (4):
wherein Y
1
and Y
2
stands, independently from each other, for an anionic group, R
1
, R
2
and R
3
stand, independently from each other, for a substituent which may be, for example, an alkyl group having 1 to 4 carbon atoms, a halogen atom such as chlorine, bromine, iodine or fluorine or a halogenated alkyl group having 1 to 4 carbon atoms, m and n are integers of 0 to 4, preferably 1 to 2, and p, q and r are integers of 0 to 6, preferably 0 to 2. A total of m and n is preferably 1 to 4, more preferably 2.
Illustrative of suitable 1,10-phenanthroline compounds are 1,10-phenanthroline-4,7-dicarboxylic acid, 1,10-phenanthroline-4,7-disulfonic acid, 1,10-phenanthroline-4,7-diphosphoric acid, 1,10-phenanthroline-3,8-dimethyl-4,7-dicarboxylic acid, 1,10-phenanthroline-3,8-dimethyl-4,7-disulfonic acid and 1,10-phenanthroline-3,8-dimethyl-4,7-diphosphoric acid.
In the platinum complex of the formula (1), L
2
represents a dithiolate selected from those represented by the formulas (a) through (d) above.
In the dithiolates of the formulas (a) through (d), the alkyl group represented by R and R
1
has 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and may be, for example, methyl, ethyl, propyl or butyl.
The alkoxyalkyl group represented by R and R
1
has 2 to 12 carbon atoms, preferably 3 to 6 carbon atoms, and is preferably represented by the following formula (5):
R
4
OR
5
—  (5)
in which R
4
represents an alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and R
5
represents an alkylene group having 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Illustrative of suitable alkoxyalkyl groups are methoxyethyl, methoxybutyl and methoxypropyl.
The aminoalkyl group represented by R and R
1
has 1 to 12 carbon atoms and is preferably represented by the following formula (6):
wherein R
6

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