Phthalocyanine nanorod and photoelectric conversion device

• US 8,895,850 B2
• Filed: 05/19/2011
• Issued: 11/25/2014
• Est. Priority Date: 05/19/2011
• Status: Expired due to Fees

• Current Assignee: DIC Corporation
• Original Assignee: DIC Corporation
• Inventors: Etori, Hideki, Murata, Hideyuki, Fukazawa, Norimasa, Inagaki, Shou
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Branch, Catherine S
• Application Number:
  US13/979,999
• Publication Number:
  US 20140158203A1
• Time in Patent Office: 1,286 Days
• Field of Search: None
• US Class Current: 136/263
• CPC Class Codes: B82Y 20/00 Nanooptics, e.g. quantum optics or photonic crystals
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 40/00 Manufacture or treatment of nanostructures
• CPC Class Codes: C09B 47/04 Phthalocyanines abbreviation: Pc
• CPC Class Codes: C09B 47/0673 having alkyl radicals linked directly to the Pc skeleton; having carbocyclic groups linked directly to the skeleton
• CPC Class Codes: C09B 47/0675 having oxygen or sulfur linked directly to the skeleton
• CPC Class Codes: C09B 47/0678 having-COOH or -SO3H radicals or derivatives thereof directly linked to the skeleton
• CPC Class Codes: C09B 67/0019 of phthalocyanines
• CPC Class Codes: C09B 67/0097 Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
• CPC Class Codes: C09B 69/00 Dyes not provided for by a single group of this subclass
• CPC Class Codes: C09D 11/52 Electrically conductive inks
• CPC Class Codes: H10K 10/484 characterised by the channel regions
• CPC Class Codes: H10K 30/00 Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20
• CPC Class Codes: H10K 30/30 comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
• CPC Class Codes: H10K 30/50 Photovoltaic [PV] devices
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/371 Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
• CPC Class Codes: H10K 85/381 Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
• 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: Y10T 428/298 : Physical dimension

Abstract

The present invention provides a phthalocyanine nanorod; an ink composition containing the phthalocyanine nanorod; a transistor containing the phthalocyanine nanorod; a material for a photoelectric conversion device, the material containing the phthalocyanine nanorod; and a photoelectric conversion device containing the phthalocyanine nanorod between the positive electrode and the negative electrode. Since an ink composition containing a nanorod according to the present invention can be formed into a film by a wet process such as a coating method or a printing method, an electronic device that is less likely to fail and is lightweight and inexpensive can be produced on a flexible plastic substrate.

Claims

1. A phthalocyanine nanorod comprising an unsubstituted phthalocyanine and a substituted phthalocyanine,

the phthalocyanine nanorod having a breadth of 100 nm or less and a ratio (length/breadth) of a length to the breadth, the ratio being less than 10,

the unsubstituted phthalocyanine being represented by a general formula (1) or (2)

2. The phthalocyanine nanorod according to claim 1, wherein the substituted phthalocyanine is represented by a general formula (5) or (6)

3. The phthalocyanine nanorod according to claim 1, wherein the substituted phthalocyanine is represented by a general formula (7) or (8)

4. An ink composition comprising, as essential components, the phthalocyanine nanorod according to claim 1 and N-methylpyrrolidone, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, toluene, xylene, ethylbenzene, chlorobenzene, dichlorobenzene, chloroform, methylene chloride, or dichloroethane.

5. The ink composition according to claim 4, wherein a content of the phthalocyanine nanorod is 0.05 to 20 mass %.

6. The ink composition according to claim 4, further comprising polythiophene, poly-p-phenylenevinylene, poly-p-phenylene, polyfluorene, polypyrrole, polyaniline, polyacetylene, polythienylenevinylene, polyvinylcarbazole, polymethyl methacrylate, polystyrene, or polycarbonate.

7. A transistor comprising a channel region containing the phthalocyanine nanorod according to claim 1.

8. A method for producing a transistor that is the transistor comprising a channel region containing the phthalocyanine nanorod, the method comprising

forming a film from the ink composition according to claim 4 to form a channel region.

9. A material for a photoelectric conversion device, the material comprising the phthalocyanine nanorod according to claim 1.

10. The material for a photoelectric conversion device according to claim 9, further comprising 1,4,5,8-naphthalenetetracarboxylic diimide (NTCDI), 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTCDA), 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA), 3,4,9,10-perylenetetracarboxylic bisbenzimidazole (PTCBI), 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD), 2,5-di(1-naphthyl)-1,3,4-oxadiazole (BND), 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1,2,4-triazole (TAZ), phenanthroline, phosphine oxide, C60 fullerene, C70 fullerene, C76 fullerene, C78 fullerene, C82 fullerene, C84 fullerene, C90 fullerene, C94 fullerene, [6,6]-phenyl-C61-butyric acid methyl ester, [6,6]-phenyl-C61-butyric acid hexyl ester, [6,6]-phenyl-C61-butyric acid dodecyl ester, phenyl-C71-butyric acid methyl ester, phenyl-C85-butyric acid methyl ester, carbon nanotube (CNT), poly-p-phenylenevinylene having a cyano group, poly[(1,4-divinylenephenylene)(2,4,6-triisopropylphenylborane)], or poly[(2,5-didecyloxy-1,4-phenylene)(2,4,6-triisopropylphenylborane)], diphenyl terminated.

11. A photoelectric conversion device comprising a positive electrode, a negative electrode, and a film containing the phthalocyanine nanorod according to claim 1, the film being disposed between the positive electrode and the negative electrode.

12. A method for producing a photoelectric conversion device comprising a positive electrode, a negative electrode, and a film containing the phthalocyanine nanorod, the method comprising

a step of forming a film from the material for a photoelectric conversion device according to claim 9 such that the film is disposed between a positive electrode and a negative electrode.

13. A method for producing a phthalocyanine nanorod that is the phthalocyanine nanorod according to claim 1, the method comprising:

(1) a step of dissolving an unsubstituted phthalocyanine and a substituted phthalocyanine in sulfuric acid, chlorosulfuric acid, methanesulfonic acid, or trifluoroacetic acid and subsequently precipitating the phthalocyanines in water or an aqueous solution mainly containing water, to provide a composite;

(2) a step of forming the composite provided in the step (1), into a nanowire by subjecting the composite to stirring or standing still in a temperature range of 5°

C. to 250°

C. in N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, toluene, xylene, ethylbenzene, chlorobenzene, or dichlorobenzene; and

(3) a step of forming the nanowire provided in the step (2), into a nanorod in the organic solvent described in (2) above by a stirring process, a dispersion-stirring process, a dispersion-homogenization process, an ultrasonic radiation process, an ultrasonic stirring process, an ultrasonic homogenization process, an ultrasonic dispersion process, or a laser radiation process,

the unsubstituted phthalocyanine being represented by a general formula (1) or (2)

14. The method for producing a phthalocyanine nanorod according to claim 13, wherein the nanowire provided in the step (2) has a breadth of 100 nm or less and a ratio (length/breadth) of a length to the breadth, the ratio being 10 or more.

15. The method for producing a phthalocyanine nanorod according to claim 13, wherein the step of forming the composite into the nanowire by subjecting the composite to stirring or standing still in a temperature range of 5°

C. to 250°

C. in N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, toluene, xylene, ethylbenzene, chlorobenzene, or dichlorobenzene, is a step of dispersing the composite in N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, toluene, xylene, ethylbenzene, chlorobenzene, or dichlorobenzene and subsequently forming the composite into the nanowire by stirring or standing still in a temperature range of 5°

C. to 250°

C.