Solvent vapor infiltration of organic materials into nanostructures

• US 6,987,071 B1
• Filed: 11/21/2003
• Issued: 01/17/2006
• Est. Priority Date: 11/21/2003
• Status: Expired due to Fees

• Current Assignee: Aeris Capital Sustainable IP, Ltd.
• Original Assignee: Nanosolar Incorporated
• Inventors: Robinson, Matthew R., Bollman, Brent J., Petritsch, Klaus
• Primary Examiner(s): Whitehead, Jr., Carl
• Assistant Examiner(s): DOTY, HEATHER ANNE
• Application Number:
  US10/719,041
• Time in Patent Office: 788 Days
• Field of Search: 438/82, 438/99, 438/623, 438/780, 438/60, 438/75, 257/40, 257/642
• US Class Current: 438/780
• CPC Class Codes: B82Y 10/00 Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• CPC Class Codes: H10K 30/151 the wide bandgap semiconductor comprising titanium oxide, e.g. TiO2
• CPC Class Codes: H10K 30/30 comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
• CPC Class Codes: H10K 30/352 the inorganic nanostructures being nanotubes or nanowires, e.g. CdTe nanotubes in P3HT polymer
• CPC Class Codes: H10K 71/10 Deposition of organic active material
• CPC Class Codes: H10K 71/441 in the presence of solvent vapors, e.g. solvent vapour annealing
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: H10K 85/221 Carbon nanotubes
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product
• CPC Class Codes: Y10S 977/753 with polymeric or organic binder
• CPC Class Codes: Y10S 977/895 having step or means utilizing chemical property

Abstract

Spaces in a nanostructure can be filled with an organic material while in the solid state below T_m (without heating) by exposing the organic material to solvent vapor while on or mixed with the nanostructured material. The exposure to solvent vapor results in intimate contact between the organic material and the nanostructured material without having to expose them to possibly detrimental heat to melt in the organic material. Solution processing methods need only to be employed to create bulk films while organic material infiltration can take place in the solid state after depositing the film.

Claims

1. A method for infiltrating an organic material into spaces in one or more nanostructures, comprising:

disposing the organic material proximate the nanostructures; and

infiltrating the organic material into the spaces in the nanostructures by exposing the organic material to a solvent vapor.

2. The method of claim 1 wherein disposing the organic material proximate the nanostructures includes disposing a layer of a polymer process solution on a nanostructured template.

3. The method of claim 2 wherein the nanostructured template has spaces between about 5 nm and about 1000 nm wide.

4. The method of claim 2 wherein the spaces in the nanostructured template include tubes between about 1 nm and about 1000 nm in diameter with a tube density between about 10¹² tubes/m² and about 10¹⁶ tubes/m².

5. The method of claim 1, wherein the nanostructures include one or more nanopores, cavities, or interstitial spaces between pores, tubes or rods.

6. The method of claim 5 wherein disposing the organic material proximate the nanostructures includes mixing the nanotubes into a polymer process solution.

7. The method of claim 1 wherein the organic material is a small molecule.

8. The method of claim 1 wherein the organic material is a pigment, dye or fullerene.

9. The method of claim 1 wherein the organic material is a polymer.

10. The method of claim 9 wherein the polymer includes one or more polymers selected from the group of poly(phenylene) and derivatives thereof, poly(phenylene vinylene) and derivatives thereof (e.g., poly(2-methoxy-5-(2-ethyl-hexyloxy)-1,4-phenylene vinylene (MEH—

PPV), poly(para-phenylene vinylene), (PPV)), PPV copolymers, poly(thiophene) and derivatives thereof (e.g., regioregular poly(3-octylthiophene-2,5,-diyl), regiorandom poly(3-octylthiophene-2,5,-diyl), poly(3-hexylthiophene) (P3HT), regioregular poly(3-hexylthiophene-2,5-diyl), regiorandom poly(3-hexylthiophene-2,5-diyl)), MDMO, poly(thienylenevinylene) and derivatives thereof, and poly(isothianaphthene) and derivatives thereof, tetra-hydro-thiophene precursors and derivatives thereof, poly-phenylene-vinylene and derivatives organometallic polymers, polymers containing perylene units, poly(squaraines) and their derivatives, discotic liquid crystals polyfluorenes, polyfluorene copolymers, polyfluorene-based copolymers and blends, polyfluorene-based copolymers co-polymerized and/or blended with charge transporting compounds and/or light absorbing compounds, polyfluorene-based copolymers co-polymerized and/or blended with tri-phenyl-amines and derivatives, polyfluorene-based copolymers co-polymerized and/or blended with fused thiophene rings and derivatives, generally hetero-atom ring compounds with or without substituents, and/or fullerenes, dyes or pigments.

11. The method of claim 10 wherein the solvent vapor is selected from the group of acetone, chloroform, benzene, cyclohexane, dichloromethane, ethanol, diethyl ether, ethyl acetate, hexane, methanol, toluene, xylene, mixtures of two or more of these, and derivatives of one or more of these.

12. A method for making an optoelectronic device, comprising:

providing a nanostructured template having spaces between one or more nanostructures;

infiltrating an organic material into the spaces by disposing the organic material proximate the nanostructures and exposing the organic material to a solvent vapor; and

placing the nanostructured template and or organic material in electrical contact with an electrode.

13. The method of claim 12 wherein disposing the organic material proximate the nanostructures includes disposing a layer of an organic process solution on a nanostructured template.

14. The method of claim 12 wherein the spaces in the nanostructured template include tubes between about 1 nm and about 1000 nm in diameter with a tube density between about 10¹² tubes/m² and about 10¹⁶ tubes/m².

15. The method of claim 12 wherein the organic material includes small molecules.

16. The method of claim 15 wherein the small molecules include pentacene or pentacene precursors.

17. The method of claim 12 wherein the organic material is a pigment, dye or fullerene.

18. The method of claim 12 wherein the organic material is a polymer.

19. The method of claim 18 wherein the polymer includes one or more polymers selected from the group of poly(phenylene) and derivatives thereof, poly(phenylene vinylene) and derivatives thereof (e.g., poly(2-methoxy-5-(2-ethyl-hexyloxy)-1,4-phenylene vinylene (MEH—

PPV), poly(para-phenylene vinylene), (PPV)), PPV copolymers, poly(thiophene) and derivatives thereof regioregular poly(3-octylthiophene-2,5,-diyl), regiorandom poly(3-octylthiophene-2,5,-diyl), poly(3-hexylthiophene) (P3HT), regioregular poly(3-hexylthiophene-2,5-diyl), regiorandom poly(3-hexylthiophene-2,5-diyl), MDMO, poly(thienylenevinylene) and derivatives thereof, and poly(isothianaphthene) and derivatives thereof, tetra-hydro-thiophene precursors and derivatives thereof, poly-phenylene-vinylene and derivatives organometallic polymers, polymers containing perylene units, poly(squaraines) and their derivatives, discotic liquid crystals polyfluorenes, polyfluorene copolymers, polyfluorene-based copolymers and blends, polyfluorene-based copolymers co-polymerized and/or blended with charge transporting compounds and/or light absorbing compounds, polyfluorene-based copolymers co-polymerized and/or blended with tri-phenyl-amines and derivatives, polyfluorene-based copolymers co-polymerized and/or blended with fused thiophene rings and derivatives, generally hetero-atom ring compounds with or without substituents, and/or fullerenes, dyes or pigments.

20. The method of claim 12 wherein solvent vapor is selected from the group of acetone, chloroform, benzene, cyclohexane, dichloromethane, ethanol, diethyl ether, ethyl acetate, hexane, methanol, toluene, xylene, mixtures of two or more of these, and derivatives of one or more of these.