Silver-(conjugated compound) composite

Patent metadata

Field	Value
Publication number	US-9412487-B2
Application number	US-201013496611-A
Country	US
Kind code	B2
Filing date	Sep 17, 2010
Priority date	Sep 18, 2009
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

A silver-(conjugated compound) composite comprising silver particles having a number-average Feret diameter of not more than 1,000 nm, and a conjugated compound having a weight-average molecular weight of not less than 3.0×10 2 adsorbed to the silver particles. The composite exhibits excellent conductivity and charge injection properties, and excellent dispersibility within non-polar solvents.

First claim

The invention claimed is:

1. A silver-(conjugated compound) composite, comprising silver particles having a number-average Feret diameter of not more than 1,000 nm, and a conjugated compound having a weight-average molecular weight of not less than 3.0×10 2 adsorbed to the silver particles,
wherein the conjugated compound has a monovalent group represented by a formula (I) shown below, a repeating unit represented by a formula (II) shown below, or a monovalent group represented by the formula (I) and a repeating unit represented by the formula (II):

wherein Ar 1 represents an aromatic group having a valency of (n 1 +1), each R 1 independently represents a single bond or a group having a valency of (m 1 +1), X 1 represents a pyrrolidonyl group, a group represented by the formula: —COOM, a group represented by the formula (p-1), or a group represented by the formula (p-2); as a monovalent group containing a hetero atom, and m 1 and n 1 are identical or different and each represents an integer of 1 or greater,
—O—(R′O) m —R″  (p-1)

wherein R′ represents a substituted or unsubstituted divalent hydrocarbon group or a group represented by a formula: —R d O—, wherein R d represents an alkylene group of 1 to 50 carbon atoms, R″ represents a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group, —CO 2 H, —SO 3 H, —OH, —SH, —NR c 2 , —CN or —C(═O)NR c 2 , wherein R c represents a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms or a substituted or unsubstituted aryl group of 6 to 50 carbon atoms, R′″ represents a substituted or unsubstituted trivalent hydrocarbon group, m represents an integer of 1 or greater, and in cases where there is a plurality of any one or more of R′, R″ and R′″ groups, in each case, the plurality of groups may be the same or different;
wherein Ar 2 represents an aromatic group having a valency of (n 2 +2), each R 2 independently represents a single bond or a group having a valency of (m 2 +1), X 2 represents a pyrrolidonyl group, a group represented by the formula: —COOM, a group represented by the formula (p-1), or a group represented by the formula (p-2); as a monovalent group containing a hetero atom, and m 2 and n 2 are identical or different and each represents an integer of 1 or greater; and
wherein the aromatic group having a valency of (n 1 +1) represented by Ar 1 and the aromatic group having a valency of (n 2 +2) represented by Ar 2 are residues in which (n 1 +1) aromatic ring-bonded hydrogen atoms and (n 2 +2) aromatic ring-bonded hydrogen atoms respectively have been removed from an aromatic compound represented by any one of formulas (2) to (26), (28) to (35), (37) and (39)-(57) shown below or a substituted aromatic compound thereof:

wherein R in the formula (55) represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group.

2. The silver-(conjugated compound) composite according to claim 1 , wherein the conjugated compound is an aromatic compound.

3. The silver-(conjugated compound) composite according to claim 1 , wherein a proportion of the conjugated compound within the silver-(conjugated compound) composite is not less than 1.0% by weight.

4. The silver-(conjugated compound) composite according to claim 1 , further comprising an unconjugated compound.

5. The silver-(conjugated compound) composite according to claim 1 , wherein the composite is in a particulate form having a number-average Feret diameter of not more than 1,100 nm.

6. The silver-(conjugated compound) composite according to claim 1 , wherein the conjugated compound is insoluble in water.

7. The silver-(conjugated compound) composite according to claim 1 , wherein a formula weight of the repeating unit represented by the formula (II) is not less than 3.0×10 2 .

8. The silver-(conjugated compound) composite according to claim 1 , wherein if a total number of atoms that exist within the composite, determined by X-ray photoelectron spectroscopy, is deemed to be 1, then a proportion of hetero atoms other than silver atoms is 0.01 or greater.

9. The silver-(conjugated compound) composite according to claim 1 , which when measured by X-ray photoelectron spectroscopy, exhibits a peak attributable to the conjugated compound that is not detected in pure metallic silver.

10. The silver-(conjugated compound) composite according to claim 1 , wherein a band gap of the conjugated compound, determined by measurement using an ultraviolet-visible-near infrared spectrometer, is 2.1 eV or greater.

11. The silver-(conjugated compound) composite according to claim 1 , wherein an ionization potential of the conjugated compound, determined by measurement in the atmosphere using a photoelectron spectrometer, is 5.2 eV or greater.

12. A method of producing the silver-(conjugated compound) composite defined in claim 1 , the method comprising the step of reducing a silver compound in presence of a conjugated compound having a weight-average molecular weight of not less than 3.0×10 2 ,
wherein the conjugated compound has a monovalent group represented by a formula (I) shown below, a repeating unit represented by a formula (II) shown below, or a monovalent group represented by the formula (I) and a repeating unit represented by the formula (II):

wherein Ar 1 represents an aromatic group having a valency of (n 1 +1), each R 1 independently represents a single bond or a group having a valency of (m 1 +1), X 1 represents a pyrrolidonyl group, a group represented by the formula: —COOM, a group represented by the formula (p-1), or a group represented by the formula (p-2); as a monovalent group containing a hetero atom, and m 1 and n 1 are identical or different and each represents an integer of 1 or greater,
—O—(R′O) m —R″  (p-1)

wherein R′ represents a substituted or unsubstituted divalent hydrocarbon group or a group represented by a formula: —R d O—, wherein R d represents an alkylene group of 1 to 50 carbon atoms, R″ represents a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group, —CO 2 H, —SO 3 H, —OH, —SH, —NR c 2 , —CN or —C(═O)NR c 2 , wherein R c represents a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms or a substituted or unsubstituted aryl group of 6 to 50 carbon atoms, R′″ represents a substituted or unsubstituted trivalent hydrocarbon group, m represents an integer of 1 or greater, and in cases where there is a plurality of any one or more of R′, R″ and R′″ groups, in each case, the plurality of groups may be the same or different;
wherein Ar 2 represents an aromatic group having a valency of (n 2 +2), each R 2 independently represents a single bond or a group having a valency of (m 2 +1), X 2 represents a pyrrolidonyl group,

Assignees

• Iijima Takayuki
• Fujioka Masahiro
• Higashimura Hideyuki
• Sumitomo Chemical Co

Inventors

• Iijima Takayuki
• Fujioka Masahiro
• Higashimura Hideyuki

Classifications

• B22F1/00

  Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties · CPC title

• B22F1/16

  Metallic particles coated with a non-metal (coated with lubricating or binding agents or with organic material B22F1/10) · CPC title

• B22F1/147

  Making a dispersion · CPC title

• B22F1/102

  Metallic powder coated with organic material · CPC title

• C08G79/00

  Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon {with or without the latter elements in the main chain of the macromolecule} · CPC title