Unlock instant, AI-driven research and patent intelligence for your innovation.

Organic dyes having rigid donor, process for producing the same, and dye-sensitized solar cell

a solar cell and organic dye technology, applied in the field of organic dyes with rigid donors and processes for producing the same, can solve the problems of poor efficiency, low power conversion efficiency of devices made from purely organic dyes, and sharp increase in environmental problems accompanied by ore-based energy consumption, and achieve the effect of high power conversion efficiency

Active Publication Date: 2016-06-30
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008]In view of above, the object of the present invention is to provide an organic dye having a rigid donor, and a process for producing the same, and a dye-sensitized solar cell. The dye-sensitized solar cell made from the organic dye provided by the present invention has relatively high power conversion efficiency.
[0033]As compared with the prior art, the organic dye provided by the present invention have the structure of formula (I) or formula (II). The dye has a rigid coplanar donor unit, and the relative energy level of the molecule is adjusted by various acceptor units and modifying groups, so that the dye-sensitized solar cell made from the dye molecule has improved power conversion efficiency. The results of experiments show that the power conversion efficiency of the dye-sensitized solar cell made from the organic dye provided by the present invention may be up to 12.5%, which is currently in a global leading position.

Problems solved by technology

Furthermore, environmental problems accompanied with consumption of the ore-based energy, such as fog and haze, are increasing sharply.
However, only a few devices made from purely organic dyes can achieve a power conversion efficiency over 10% currently.
The poor efficiency has become a crucial obstacle that puzzles the development of purely organic dyes for a long time.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Organic dyes having rigid donor, process for producing the same, and dye-sensitized solar cell
  • Organic dyes having rigid donor, process for producing the same, and dye-sensitized solar cell
  • Organic dyes having rigid donor, process for producing the same, and dye-sensitized solar cell

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0094]The reaction scheme is shown as follows:

[0095]wherein R1′ is

R2′ is hexyl. Also, in the following Examples, they are the same as in this Example.

1.1 Synthesis of the Intermediate 2

[0096]In a three-necked round-bottom flask, 2.00 g of the compound 1 was dissolved in 20 mL N,N-dimethyl formamide. 4.33 g 2-hexyldecyl-4-methylbenzenesulfonate and 2.13 g potassium hydroxide were added to the reaction system, and then the mixture is heated to 100° C. and reacted under stirring, and the reaction is kept overnight.

[0097]After the reaction was finished, the reaction system was cooled to room temperature, and 20 mL water was added thereto. The resultant mixture solution was extracted with chloroform three times. The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated, and then was separated by column chromatography with petroleum ether (boiling point: 60-90° C.) as the eluent to give 3.91 g of the in...

example 2

[0143]The reaction scheme is shown as follows:

2.1 Synthesis of the Intermediate 14

[0144]In a three-necked round-bottom flask, 1.00 g of the intermediate 10 from Example 1, 184 mg of the compound 13 and 871 mg potassium phosphate were dissolved in a mixed solvent of 20 mL 1,4-dioxane and 4 mL water. 4 mg Pd(OAc)2 as the catalyst and 8 mg 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos) as the organophosphine ligand were added under the protection of argon. The reaction system was heated to 45° C., and the reaction is kept for 12 hours.

[0145]After the reaction was finished, the reaction system was cooled to room temperature, and 20 mL water was added thereto. The resultant mixture solution was extracted with chloroform three times. The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated, and then was separated by column chromatography with ethyl acetate / petroleum ether (volume ratio: 1 / 50) ...

example 3

[0161]The reaction scheme is shown as follows:

3.1 Synthesis of the Intermediate 18

[0162]In a three-necked round-bottom flask, 1.00 g of the intermediate 10 from Example 1, 399 mg of the compound 17 and 871 mg potassium phosphate were dissolved in a mixed solvent of 20 mL 1,4-dioxane and 4 mL water. 4 mg Pd(OAc)2 as the catalyst and 8 mg 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos) as the organophosphine ligand were added under the protection of argon. The reaction system was heated to reflux, and the reaction is kept for 12 hours.

[0163]After the reaction was finished, the reaction system was cooled to room temperature, and 20 mL water was added thereto. The resultant mixture solution was extracted with chloroform three times. The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated, and then was separated by column chromatography with ethyl acetate / petroleum ether (volume ratio: 1 / 50) ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
reaction timeaaaaaaaaaa
reaction timeaaaaaaaaaa
temperatureaaaaaaaaaa
Login to View More

Abstract

The present invention provides organic dyes having a rigid donor and the process for producing the same. The organic dye has the structure of formula (i) or formula (ii), wherein r1 is selected from h or c1-c18 alkyl; r5 is selected from h, c1-c18 alkyl or c1-c18 alkoxy; r6 and r7 are independently selected from h, c1-c18 alkyl, c1-c18 alkoxyphenyl or c1-c18 alkylphenyl; x is selected from any one of the groups represented by formulae (a) to (d); y is selected from a group represented by formula (e) or formula (f); in the formula (e), r2 and r3 are independently selected from h, f, c1-c18 alkyl or c1-c18 alkoxyphenyl; r4 is selected from any one of the groups represented by formulae (g) to (i). The present invention also provides a dye-sensitized solar cell which has a dye layer made from said organic dyes and has a relatively high power conversion efficiency.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of Chinese Application No. 201410817172.8, filed on Dec. 25, 2014, the content of which is hereby incorporated by reference in its entirety.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present invention relates to the technical field of dye-sensitized solar cells, in particular, to an organic dye having a rigid donor and a process for producing the same, and a dye-sensitized solar cell.[0004]2. Background Information[0005]Stepping into the 21th century, the energy demand increases dramatically with the fast economic development in China. At present, China has become the largest energy-importing country in the world. Furthermore, environmental problems accompanied with consumption of the ore-based energy, such as fog and haze, are increasing sharply. Therefore, starving for a clean and sustainable energy has continued to prompt the intensive research on the development and utilizat...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): C09B5/02H01G9/20H01L51/00
CPCC09B5/028H01G9/2059H01L51/0068H01L51/0072Y02E10/542Y02E10/549H10K85/655H10K85/6572
Inventor WANG, PENGYAO, ZHAOYANG
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI