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Squarylium dye, dye-sensitized solar cell using the dye, and photoelectric conversion element using the dye

A technology of squarylium and pigment, applied in the field of pigment-sensitized solar cells, capable of solving problems such as undisclosed benzindole compounds

Inactive Publication Date: 2012-12-05
NIPPON STEEL CHEMICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Synthesis methods of substituted indoles are exemplified in Non-Patent Documents 5 and 6, but benzindole compounds having an ester group are not disclosed

Method used

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  • Squarylium dye, dye-sensitized solar cell using the dye, and photoelectric conversion element using the dye
  • Squarylium dye, dye-sensitized solar cell using the dye, and photoelectric conversion element using the dye
  • Squarylium dye, dye-sensitized solar cell using the dye, and photoelectric conversion element using the dye

Examples

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Embodiment

[0104] Hereinafter, the present invention will be described in more detail based on Examples and Comparative Examples. It should be noted that Synthesis Examples 1 to 9 and 13 can be understood as examples (excluding the dye D-6).

Synthetic example 1

[0106]

[0107] Ethoxycarbonylbenzoindolenine, using 1-bromo-4-ethoxycarbonylnaphthalene, benzophenone hydrazone, palladium acetate, BINAP, sodium butoxide, methyl isopropyl ketone, p-toluenesulfonic acid Commercially available reagents were used for synthesis. 78.87 mmol of 1-bromo-4-ethoxycarbonylnaphthalene was dissolved in a toluene solvent, palladium acetate and BINAP were added, and then 78.87 mol of benzohydrazone and sodium butoxide were added to react overnight at 80°C. Further, 123.46 mmol of methyl isopropyl ketone and p-toluenesulfonic acid monohydrate were added and reacted overnight in an ethanol solvent to obtain the target benzoindolenine ester in a yield of 30%.

Synthetic example 2

[0109] For the synthesis of N-n-alkylethoxycarbonylbenzoindolenine salt, dissolve 2,3,3-trimethyl-6-ethoxycarbonylbenzoindolenine 0.1mol and 1-Iodoethane was reacted for 7 hours under reflux. The solid content was filtered to obtain 1-n-ethyl-2,3,3-trimethyl-6-ethoxycarbonylbenzoindolenine iodide in a yield of 55%.

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Abstract

Disclosed are: a novel squarylium dye which is capable of improving the photoelectric conversion efficiency in the near infrared region,and a dye-sensitized solar cell and a photoelectric conversion element, each using the squarylium dye and having improved photoelectric conversion efficiency. Specifically disclosed is a squarylium dye represented by formula (1). In the formula, R1-R7 and R'1-R'7 each represents a hydrogen atom, an alkyl group, a sulfoalkyl group, a cycloalkyl group, an alkoxyl group, an aryl group, a halogen atom or the like,X and Y each represents a hydrogen atom or -COOR (wherein R represents a hydrogen atom or a C1-C12 alkyl group), with both or either of X and Y being -COOR,and R8 and / or R'8 represents a C3-C30 alkyl group, a C3-C30 halogen-substituted alkyl group, a C3-C30 hydroxycarbonylalkyl group, RCOO- or RSO3- (wherein R represents a C1-C30 alkyl group).

Description

technical field [0001] The present invention relates to squarylium dyes and semisquarylium dyes having an indole structure, photoelectric conversion elements and dye-sensitized solar cells using these dyes. Background technique [0002] Photoelectric conversion elements are used in photoelectric power generation devices such as photosensors and solar cells. A photoelectric conversion element using semiconductor fine particles sensitized by a dye is known in Patent Document 1 and the like. [0003] Solar cells using single crystal, polycrystalline, or amorphous silicon semiconductors are widely used in electrical appliances such as desktop computers, and in houses. However, in the manufacture of solar cells using such silicon semiconductors, since high-precision processes such as plasma CVD and high-temperature crystal growth processes are used, a lot of energy is required, and an expensive device requiring vacuum is required. The cost becomes higher. [0004] Therefore, d...

Claims

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Application Information

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IPC IPC(8): C09B23/00H01L31/04H01M14/00
CPCC09B57/007Y02E10/542H01G9/2059C09B23/0066H01G9/2031H01L51/0064Y02E10/549Y02P70/50H10K85/652C09B23/00H01L31/04H01M14/00
Inventor 早濑修二S·S·潘戴伊山口能弘
Owner NIPPON STEEL CHEMICAL CO LTD
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