Isodiketopyrrolopyrrole dye and use thereof

Patent metadata

Field	Value
Publication number	US-11056287-B2
Application number	US-201515747766-A
Country	US
Kind code	B2
Filing date	Dec 31, 2015
Priority date	Jul 28, 2015
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

The present invention discloses an isodiketopyrrolopyrrole dye and use thereof. A series of pure organic dye based on isodiketopyrrolopyrrole are synthesized in the present invention, using 4,4′-dihexyloxytriphenylamine as an electron donor, isodiketopyrrolopyrrole as a π-bridge, and cyanoacetic acid as an electron acceptor and an anchoring group, and with a alkyl chain introduced on an isodiketopyrrolopyrrole group. The types of dyes have a relatively good light-harvesting performance as well as a relatively large steric hindrance, and they are not easy to gather while being absorbed on a semiconducting film. The pure organic dye with isodiketopyrrolopyrrole as an electronic π-bridge, which is used in a dye-sensitized solar cell, has a good ability of inhibiting the recombination of electrons, and the dye-sensitized solar cells have a high photoelectric conversion efficiency.

First claim

What is claimed:

1. A pure organic dye with an isodiketopyrrolopyrrole group introduced in a π-bridge, comprising a general structural formula as follows:

wherein, R 1 is C 6 H 13 O, R 2 is 2-ethylhexyl; and A 1 and A 2 are each a benzene ring.

2. A dye-sensitized solar cell comprising the pure organic dye with the isodiketopyrrolopyrrole group introduced in the π-bridge according to claim 1 , consisting essentially of:
a conductive glass substrate, a photoanode, a sensitizer, an electrolyte and a counter electrode;
wherein a nano-porous TiO 2 film that can be used to absorb the sensitizer is provided in the middle of the conductive glass substrate on one side of a substrate work zone of the photoanode; the counter electrode is also called a photocathode, a catalyst layer is provided in the middle of the conductive glass substrate on one side of a substrate work zone of the photocathode,
wherein a catalyst of the catalyst layer is Pt; the photoanode and the photocathode are alternately configured opposite, the nano-porous TiO 2 film is sealed peripherally with a sealing material to form an airtight cavity, and the airtight cavity is filled with the electrolyte and the sensitizer, wherein the sensitizer is the pure organic dye with the isodiketopyrrolopyrrole group introduced in the π-bridge.

3. A method for preparing a dye-sensitized solar cell of claim 2 , comprising preparation steps of:
(1) pretreatment of a conductive glass of FTO: ultrasonic cleaning a cut FTO and washing for 3-6 times with deionized water, and then soaking in a saturated ethanol solution of KOH for 16-36 h, followed by ultrasonic cleaning sequentially with deionized water, acetone, deionized water and ethanol, and keeping for use after drying;
(2) preparation of a photoanode: at room temperature, adding 35-80 mL of acetic acid and deionized water under intensive stirring to a mixed solution of 10-25 mL of Ti(OBu) 2 and 15-30 mL of EtOH, and continue to stir for 30 min to 2 h, transferring the mixed solution into an autoclave which is lined with polytetrafluoroethylene, treating at 200-280° C. for 8-20 h followed by natural cooling to room temperature, filtering an obtained suspension, sequentially washing for 3-6 times with deionized water and ethanol, drying in an oven at 40-60° C. for 4-8 h until dry to obtain TiO 2 nanocrystalline particles, respectively adding ethanol, acetic acid, terpilenol and ethyl cellulose into the prepared TiO 2 nanocrystalline particles, grinding the mixture thoroughly to obtain a muddy substance, and obtaining a white sticky TiO 2 nanocrystalline slurry as required through ultrasonic processing;
making a conductive plane of the treated conductive glass upward, placing a screen mesh sheet above the glass, controlling an off-contact distance to be 0.5-3 cm, placing the prepared TiO 2 nanocrystalline slurry on the screen mesh sheet to perform printing; putting the prepared photoanode into an oven for drying at 100-150° C., and then putting into a muffle furnace for sequential treatment at different temperatures: baking at 300-350° C. for 3-10 min, baking at 300-400° C. for 3-10 min, baking at 400-500° C. for 10-20 min, and baking at 450-550° C. for 10-20 min to fully remove an organic substance on the film, and subsequently soaking into a prepared 0.1-0.3 M TiCl 4 aqueous solution to treat for 30 min to 1.5 h, washing clean with deionized water and ethanol after the treatment is finished, putting into the muffle furnace and heating up to 450-550° C. to bake again for 25-40 min, and cooling to 60-80° C. for use;
(3) preparation of a dye solution: dissolving the isodiketopyrrolopyrrole dye into a mixed solvent of chloroform/methanol to formulate a dye solution of 1×10 −4 mol·L −1 to 3×10 −4 mol·L −1 , with a volume ratio of chloroform/methanol of 4/1-1/4;
(4) preparation of an electrolyte solution: dissolving 0.5-0.7 M 1-methyl-3-propylimidazolium iodide (PMII), 0.03-0.07 M guanidine thiocyanate, 0.03-0.07 M LiI, 0.01-0.04 M 12 and 0.15-0.40 M tert-butyl pyridine (TBP) into acetonitrile, and mixing uniformly to obtain a clear solution;
(5) sensitization of the photoanode: soaking the photoanode prepared in step (2) into the dye solution prepared in step (3), taking the photoanode out and washing with the mixed solvent of chloroform/methanol to remove the residual on the surface or the dye on a film surface after performing a dye bath in a dark environment for 10-20 hours, and blow-drying followed by keeping the photoanode in a dry and dark environment for packaging and use; with the volume ratio of chloroform/methanol of 4/1-1/4; and
(6) making an adhesive tape into a suitable inner hole plastic by using a hole puncher, putting an insulative thin film on the sensitized photoanode to enable the photoanode to be exactly inside an inner hole of the insulative thin film, dropping 1-2 drops of the electrolyte solution prepared in step (4) onto a surface of the TiO 2 film, and covering a platinum counter electrode on the photoanode with two sides being fixed with clamps, and then an open dye-sensitized solar cell to be tested is formed.

Assignees

• Univ South China Tech

Inventors

• Cao Derong
• Zang Xufeng

Classifications

• H01G9/2031

  comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence) · CPC title

• H01G9/2004

  characterised by the electrolyte, e.g. comprising an organic electrolyte · CPC title

• H01G9/2059 Primary

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title

• Y02P70/50

  Manufacturing or production processes characterised by the final manufactured product · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title