Silver ion carboxylate N-heteroaromatic complexes

Patent metadata

Field	Value
Publication number	US-9809606-B1
Application number	US-201615231804-A
Country	US
Kind code	B1
Filing date	Aug 9, 2016
Priority date	Aug 9, 2016
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

A non-hydroxylic-solvent soluble silver complex comprises a reducible silver ion complexed with an α-oxy carboxylate and a 5- or 6-membered N-heteroaromatic compound. The non-hydroxylic-solvent soluble silver complex can be represented by the following formula (I):

(Ag + ) a (L) b (P) c    (I)

wherein L represents the α-oxy carboxylate; P represents the 5- or 6-membered N-heteroaromatic compound; a is 1 or 2; b is 1 or 2; and c is 1, 2, 3, or 4, provided that when a is 1, b is 1, and when a is 2, b is 2. Such complexes can be incorporated into photosensitive compositions for thin films or patterns in various articles to provide electrically-conductive silver metal.

First claim

The invention claimed is:

1. A non-hydroxylic-solvent soluble silver complex comprising a reducible silver ion complexed with an α-oxy carboxylate and a 5- or 6-membered N-heteroaromatic compound,
the non-hydroxylic-solvent soluble silver complex being represented by the following formula (I):
(Ag + ) a (L) b (P) c    (I)

wherein L represents the α-oxy carboxylate; P represents the 5- or 6-membered N-heteroaromatic compound; a is 1 or 2; b is 1 or 2; and c is 1, 2, 3, or 4, provided that when a is 1, b is 1, and when a is 2, b is 2,
wherein L is represented by either of the following formula (II) or formula (III), and P is selected from the group consisting of pyridine, 2-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, 2,3-dimethylpyridine, 3,4-dimethylpyridine, 4-pyridylacetone, 3-chloropyridine, 3-fluoropyridine, oxazole, 4-methyloxazole, isoxazole, 3-methylisoxazole, pyrimidine, 2-methyl pyrimidine, pyrazine, 4-methyl pyrimidine, pyridazine, and thiazole;

wherein R 1 , R 2 , and R 3 are independently hydrogen or branched or linear alkyl groups; and

wherein R 4 is a branched or linear alkyl group having 1 to 8 carbon atoms and optionally, any of the hydrogen atoms in the R 4 branched or linear alkyl group optionally can be substituted with a fluorine atom.

2. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein R 1 is hydrogen or a branched or linear alkyl group having 1 to 3 carbon atoms, and R 2 and R 3 are independently branched or linear alkyl groups having 1 to 8 carbon atoms, wherein any of the hydrogen atoms in the R 1 , R 2 , and R 3 branched or linear alkyl groups optionally can be replaced with a fluorine atom.

3. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the α-oxy carboxylate has a molecular weight of 250 or less.

4. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the α-oxy carboxylate is selected from the group consisting of lactate, 2-hydroxybutyric acid, 2-hydroxy-3-methylbutyric acid, 2-hydroxy-3,3-dimethylbutyric acid, 2-hydroxy-isobutyric acid, 2-methoxy-isobutyric acid, 2-hydroxy-2-methylbutyric acid, 2-ethyl-2-hydroxybutyric acid, 2-hydroxy-2,3-dimethylbutyric acid, 2-ethyl-2-methoxybutyric acid, 2-methoxy-2-methylpropanoic acid, 1-hydroxycyclopentane-1-carboxylic acid, 2,3-dihydroxy-2,3-dimethylsuccinic acid, and 2,4-dihydroxy-2,4-dimethylpentanedioic acid, or
selected from the group consisting of pyruvic acid, 3-methylpyruvic acid, 3,3-dimethylpyruvic acid, 3,3-dimethyl-2-oxobutanoic acid, 3,3-dimethyl-2-oxopentanoic acid, 3-methyl-2-oxobutanoic acid, and 2,3-dioxosuccinic acid.

5. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein P is a pyridine.

6. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has an oxidation potential of at least 1.0 V vs. SCE; the α-oxy carboxylate has a first oxidation potential of at least 1.2 V vs. SCE; and upon decarboxylation of the α-oxy carboxylate, a second radical is generated that has an oxidation potential of less than 1.0 V vs. SCE.

7. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has an oxidation potential of at least 1.5 V vs. SCE.

8. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has an oxidation potential of at least 2.0 V vs. SCE.

9. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has a molecular weight of 200 or less.

10. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has a molecular weight of at least 80 and up to and including 150.

11. The non-hydroxylic-solvent soluble silver complex of claim 1 , which meets a silver ion stability test such that when the non-hydroxylic-solvent soluble silver complex is held for 24 hours at ambient temperature and under yellow safelight, less than 0.1 mol % of its original silver ion content is reduced to silver metal.

12. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein:
(i) a and b are both 1 and c is 1 or 2;
(ii) a and b are both 2 and c is 2; or
(iii) a and b are both 2 and c is 4.

Assignees

• Eastman Kodak Co

Inventors

• Shukla Deepak

Classifications

• G03F7/063

  Additives or means to improve the lithographic properties; Processing solutions characterised by such additives; Treatment after development or transfer, e.g. finishing, washing; Correction or deletion fluids · CPC title

• C07F1/005 Primary

  without C-Metal linkages · CPC title

• G03F7/06

  Silver salts (G03F7/075 takes precedence) · CPC title