Wavelength conversion perylene diester chromophores and luminescent films

• US 9,287,419 B2
• Filed: 01/04/2012
• Issued: 03/15/2016
• Est. Priority Date: 01/05/2011
• Status: Active Grant

• Current Assignee: Choshu Industry Co., Ltd.
• Original Assignee: Nitto Denko Corporation
• Inventors: Jiang, Zongcheng, Wang, Peng, Yamamoto, Michiharu, Wang, Shuangxi, Rachwal, Bogumila, Zhang, Hongxi
• Primary Examiner(s): Pillay, Devina
• Application Number:
  US13/978,370
• Publication Number:
  US 20130284265A1
• Time in Patent Office: 1,532 Days
• Field of Search: 136/263
• US Class Current: 1/1
• CPC Class Codes: C09B 3/14 Perylene derivatives
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: H01L 31/02168 the coatings being antireflective or having enhancing optical properties for the solar cells
• CPC Class Codes: H10K 85/623 containing five rings, e.g. pentacene
• CPC Class Codes: Y02E 10/52 PV systems with concentrators

Abstract

This invention is related to novel perylene diester derivatives represented by the general formula (I) or general formula (II) as described herein. The derivatives are useful in various applications, such as luminescent dyes for optical light collection systems, fluorescence-based solar collectors, fluorescence-activated displays, and/or single-molecule spectroscopy. The invention also relates to a luminescent medium, such as a luminescent film, that can significantly enhance the solar harvesting efficiency of thin film CdS/CdTe or CIGS solar cells. The luminescent medium comprises an optically transparent polymer matrix and at least one luminescent dye that comprises a perylene diester derivative. Over 16% of an efficiency enhancement to a CdS/CdTe solar cell and over 12% of an efficiency enhancement to a CIGS solar cell can be achieved.

Claims

1. A perylene diester derivative represented by the following general formula (I) or general formula (II):

2. The perylene diester derivative of claim 1, wherein R₁ and R₁′

are independently selected from the group consisting of hydrogen, C₁-C₆ alkyl, C₂-C₆ alkoxyalkyl, and C₆-C₁₈ aryl.

3. The perylene diester derivative of claim 1, wherein R₁ and R₁′

are each independently selected from the group consisting of isopropyl, isobutyl, isohexyl, isooctyl, 2-ethyl-hexyl, diphenylmethyl, trityl, and diphenyl.

4. The perylene diester derivative of claim 1, wherein R₂ and R₂′

are each independently selected from the group consisting of diphenylmethyl, trityl, and diphenyl.

5. An organic down-shifting luminescent medium comprising an optically transparent polymer matrix and at least one luminescent dye;

wherein the organic down-shifting luminescent medium receives as input at least one photon having a first wavelength, and provides as output at least one photon having a second wavelength, wherein the second wavelength is longer than the first wavelength;

wherein the luminescent dye comprises the perylene diester derivative of claims 1.

6. The organic down-shifting luminescent medium of claim 5, wherein the polymer matrix comprises a polymer selected from the group consisting of polymethyl methacrylate, polyvinyl butyral, ethylene vinyl acetate, ethylene tetrafluoroethylene, polyimide, amorphous polycarbonate, polystyrene, siloxane sol-gel, polyurethane, polyacrylate, and combinations thereof.

7. The organic down-shifting luminescent medium of claim 5, wherein the refractive index of the polymer matrix is in the range of about 1.400 to about 1.700.

8. The organic down-shifting luminescent medium of claim 5, wherein the luminescent dye is present in the polymer matrix in an amount in the range of about 0.01 wt % to about 3.0 wt %.

9. A photovoltaic module for the conversion of solar light energy into electricity, comprising at least one photovoltaic device or solar cell, and an organic down-shifting luminescent medium according to claims 5;

wherein the at least one photovoltaic device or solar cell is adapted to convert incident solar light energy into electricity;

wherein the at least one photovoltaic device or solar cell comprises a light incident surface substrate; and

wherein the organic down-shifting luminescent medium is incorporated on top of, or into, the photovoltaic device or solar cell, such that the incident light passes through the organic down-shifting luminescent medium prior to reaching an area of the photovoltaic module where solar light energy is converted into electricity.

10. The photovoltaic module of claim 9, wherein the organic down-shifting luminescent medium is in the form of a film having a thickness in the range of about 0.1 μ

m to about 1 mm.

11. The photovoltaic module of claim 9, wherein the organic down-shifting luminescent medium is in the form of a film with a thickness in the range of about 0.5 μ

m to about 0.5 mm.

12. The photovoltaic module of claim 9, wherein the photovoltaic device or solar cell comprises a Cadmium Sulfide/Cadmium Telluride solar cell or a Copper Indium Gallium Diselenide solar cell.

13. The photovoltaic module of claim 9, further comprising a refractive index matching liquid or optical adhesive that is used to attach the organic down-shifting luminescent medium to the light incident surface substrate of the photovoltaic device or solar cell.

14. A method for improving the performance of a photovoltaic device or a solar cell, comprising:

applying an organic down-shifting luminescent medium according to claim 5 directly onto the light incident side of the photovoltaic device or solar cell.

15. The method of claim 14, wherein the organic down-shifting luminescent medium is applied as a film with a thickness in the range of about 0.1 μ

m to about 1 mm.

16. The method of claim 14, wherein the photovoltaic device or solar cell device comprises a Cadmium Sulfide/Cadmium Telluride solar cell or a Copper Indium Gallium Diselenide solar cell.

17. The method of claim 14, further comprising applying a refractive index matching liquid or optical adhesive to the organic down-shifting luminescent medium or the light incident surface substrate of the photovoltaic device or solar cell.

18. A method for improving the performance of a photovoltaic device or solar cell, comprising:

incorporating an organic down-shifting luminescent medium according to claim 5 directly into the photovoltaic device or solar cell during its fabrication, such that the organic down-shifting luminescent medium is between the photovoltaic device or solar cell and a cover substrate on the light incident side.

19. The method of claim 18, wherein the organic down-shifting luminescent medium is a film with a thickness in the range of about 0.1 μ

m to about 1 mm.

20. The method of claim 18, wherein the photovoltaic device or solar cell device comprises a Cadmium Sulfide/Cadmium Telluride solar cell or a Copper Indium Gallium Diselenide solar cell.