Semiconductor particle sensitized with methine dye

Details Semiconductor particle sensitized with methine dye Semiconductor particle sensitized with methine dye

1999-09-29

2002-01-01

Chapman, Mark (Department: 1753)

Batteries: thermoelectric and photoelectric

Photoelectric

Cells

C257S436000

Reexamination Certificate

active

06335481

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a semiconductor particle having a surface on which a methine dye is adsorbed. The invention also relates to a photoelectric material using the particles and a photoelectric conversion device using the material.
BACKGROUND OF THE INVENTION
A photoelectric material (photovoltaic element) is used in various photosensors, copying machines and photovoltaic devices. The photoelectric materials are constructed according to a method using a metal as a photosensor, a method using a semiconductor as a photosensor, a method using an organic pigment or a dye as a photosensor or a complex method.
The semiconductor photosensor method uses semiconductor particles spectrally sensitized with a dye. U.S. Pat. Nos. 4,684,537, 4,927,721, 5,084,365, 5,350644, 5,463,057, 5,525,440 and Japanese Patent Provisional Publication No. 7(1995)-249790 disclose the semiconductor particles spectrally sensitized with a dye. The spectral sensitizing dyes used in the publications are usually ruthenium complexes, which are rather expensive.
Japanese Patent Provisional Publication No. 7(1995)-249790 further describes that a methine dye such as a cyanine dye or a merocyanine dye can be used as a spectral sensitizing dye for the semiconductor particles. The methine dye has been researched and developed as a spectral sensitizing dye for silver halide grains of a silver halide photo graphic material. Various methine dyes are practically used in a large scale in the technical field of the silver halide photography. Therefore, many methine dyes, which are inexpensive and excellent in optical characteristics are known in the silver halide photography.
SUMMARY OF THE INVENTION
In a silver halide photographic material, a methine dye is used as a spectral sensitizing dye, a filter dye, an antiirradiation dye or an antihalation dye. The silver halide photographic material is usually sensitive to a visible light to form a visible image. Therefore, the photographic methine dye usually has the maximum absorption within the visible wavelength region. However, the visible, light has a low photoelectric conversion efficiency.
An object of the present invention is to improve the photoelectric conversion efficiency.
Another object of the invention is to provide a semiconductor particle sensitized with an infrared wavelength. region.
A further object of the invention is to provide a photoelectric material and a photoelectric conversion device having a high photovoltaic effect.
A furthermore object of the invention is to provide a new methine dye having the maximum absorption within the infrared region.
The present invention provides a semiconductor particle having a surface on which a methine dye is adsorbed, wherein the methine dye is represented by the formula (I):
in which Q
1
is a tetravalent aromatic group; each of X
1
and X
2
independently is a single bond or —CR
3
═CR
4
—; when X
1
is a single bond, Y
1
is —O—, —S—, —Se—, —NR
5
—, —CR
6
R
7
— or —CR
8
═CR
9
—; when X
1
is —CR
3
═CR
4
—, Y
1
is a single bond; when X
2
is a single bond, Y
2
is —O—, —S—, —Se—, —NR
5
—, —CR
6
R
7
— or —CR
8
═CR
9
—; when X
2
is —CR
3
═CR
4
—, Y
2
is a single bond; each of R
1
and R
2
independently is an aliphatic group or an aromatic group; each of R
3
, R
4
, R
5
, R
6
, R
7
, R
8
and R
9
independently is hydrogen or an alkyl group; each of P
1
and P
2
independently is ═L
1
—Bo, ═L
2
═Ak or ═L
3
—Ar; L
1
is a methine chain having an odd number of methines; Bo is an onium form of a basic nucleus; L
2
is a methine chain having an even number of methines; Ak is an acidic nucleus of a keto type; L
3
is a methine chain having an odd number of methines; and Ar is an aromatic nucleus.
The invention also provides a photoelectric material comprising a conductive support and a light-sensitive layer containing semiconductor particles spectrally sensitized with a methine dye, wherein the methine dye is represented by the formula (I).
The invention further provides a photoelectric conversion device comprising a photoelectric material, a charge transfer layer and a counter electrode, said photoelectric material comprising a conductive support and a light-sensitive layer containing semiconductor particles spectrally sensitized with a methine dye, wherein the methine dye is represented by the formula (I).
The invention furthermore provides a methine compound represented by the formula (Va):
in which each of X
101
and X
102
independently is a single bond or —CR
103
═CR
104
—; when X
101
is a single bond, Y
101
is —O—, —S—, —Se—, —NR
105
—, —CR
106
R
107
— or —CR
108
═CR
109
—; when X
101
is —CR
103
═CR
104
—, Y
101
is a single bond; when X
102
is a single bond, Y
102
is —O—, —S—, —Se—, —NR
105
—, —CR
106
R
107
— or —CR
108
═CR
109
—; when X
102
is —CR
103
═CR
104
—, Y
102
is a single bond; each of R
101
and R
102
independently is an aliphatic group or an aromatic group; each of R
103
, R
104
, R
105
, R
106
, R
107
, R
108
and R
109
independently is hydrogen or an alkyl group; each of X
103
and X
104
independently is a double bond or ═CR
113
—CR
114
═; when X
103
is a double bond, Y
103
is —O—, —S—, —Se—, —NR
115
—, —CR
116
R
117
— or —CR
118
═CR
119
—; when X
103
is ═CR
113
—CR
114
═, Y
103
is a single bond; when X
104
is a double bond, Y
104
is —O—, —S—, —Se—, —NR
115
—, —CR
116
R
117
— or —CR
118
═CR
119
—; when X
104
is ═CR
113
—CR
114
═, Y
104
is a single bond; each of R
111
and R
112
independently is an aliphatic group or an aromatic group; each of R
113
, R
114
, R
115
, R
116
, R
117
, R
118
and R
119
independently is hydrogen or an alkyl group; each of the benzene rings A and B may be condensed with another benzene ring; and the benzene rings A, B and the condensed benzene rings may have a substituent group.
The invention still furthermore provides a methine compound represented by the formula (Vb):
in which each of X
121
and X
122
independently is a single bond or —CR
123
═CR
124
—; when X
121
is a single bond, Y
121
is —O—, —S—, —Se—, —NR
125
—, —CR
126
R
127
— or —CR
128
═CR
129
—; when X
121
is —CR
123
═CR
124
—, Y
121
is a single bond; when X
122
is a single bond, Y
122
is —O—, —S—, —Se—, —NR
125
—, —CR
126
R
127
— or —CR
128
═CR
129
—; when X
122
is —CR
123
═CR
124
—, Y
122
is a single bond; each of R
121
and R
122
independently is an aliphatic group or an aromatic group; each of R
123
, R
124
, R
125
, R
126
, R
127
, R
128
and R
129
independently is hydrogen or an alkyl group; each of X
123
and X
124
independently is a double bond or ═CR
133
—CR
134
═; when X
123
is a double bond, Y
123
is —O—, —S—, —Se—, —NR
135
—, —CR
136
R
137
— or —CR
138
═CR
139
—; when X
123
is ═CR
133
—CR
134
═, Y
123
is a single bond; when X
124
is a double bond, Y
124
is —O—, —S—, —Se—, —NR
135
—, —CR
136
R
137
— or —CR
138
═CR
139
—; when X
124
is ═CR
133
—CR
134
═, Y
124
is a single bond; each of R
131
and R
132
independently is an aliphatic group or an aromatic group; each of R
133
, R
134
, R
135
, R
136
, R
137
, R
138
and R
139
independently is hydrogen or an alkyl group; each of the benzene rings C and D may be condensed with another benzene ring; and the benzene rings C, D and the condensed benzene rings may have a substituent group.
The present inventors have found that the methine dye represented by the formula (I) has a large absorption within the infrared region. An infrared ray has a high photoelectric conversion efficiency, compared with the visible light.
The semiconductor particles can be strongly sensitized to the infrared ray by using adsorbing the methine dye represented by the formula (I) on the surface of the particles. A photovoltaic effect of a photoelectric material and a photoelectric conversion device are improved by using the semiconductor particles sensitized to the infrared ray. As a result, an inexpensive and excellent photoelectric mat

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