IP Library Granted Patent US 10,186,342
Granted Patent B2
US 10,186,342 · App. 15/231,811 · Granted Jan 22, 2019

Photosensitive reducible silver ion-containing compositions

Inventor: Deepak Shukla (Webster, NY)
Assignee: Eastman Kodak Company
H01B1/02G03F7/06
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Quick Facts
Patent No.
US 10,186,342
App. No.
15/231,811
Granted
Jan 22, 2019
Kind
B2
Abstract

A photosensitive reducible silver ion-containing composition can be used to provide electrically-conductive silver metal in thin films or patterns. This composition comprises: a) a non-hydroxylic-solvent soluble silver complex represented by the following formula (I): (Ag + ) a (L) b (P) c    (I) wherein L represents an α-oxy carboxylate; P represents a 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; b) optionally, a photosensitizer that can either reduce the reducible silver ion or oxidize the α-oxy carboxylate; and c) a solvent medium comprising at least one non-hydroxylic solvent. Electrically-conductive silver can be provided by photochemical conversion of the reducible silver ions in the complex.

Claims (20)

1. A photosensitive reducible silver ion-containing composition comprising:

a) 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;

b) optionally, a photosensitizer that can either reduce the reducible silver ion or oxidize the α-oxy carboxylate; and

c) a solvent medium comprising at least one non-hydroxylic solvent,

wherein L is represented by the following formula (II):

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.

2. The photosensitive reducible silver ion-containing composition of claim 1 , wherein one or more non-hydroxylic-solvent soluble silver complexes are present in an amount of at least 5 weight % and up to and including 90 weight % based on the total weight of the photosensitive reducible silver ion-containing composition.

3. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the solvent medium comprises one or more non-hydroxylic solvents selected from the group consisting of acetonitrile, benzonitrile, acetone, methyl ethyl ketone, butyronitrile, propylene carbonate, propionitrile, isovaleronitrile, valeronitrile, and a mixture of two or more of these organic solvents.

4. The photosensitive reducible silver ion-containing composition of claim 1 that meets a silver ion stability test such that when the photosensitive reducible silver ion-containing composition is held for 24 hours at ambient temperature and in yellow safelight, less than 0.1 mol % of its original silver ion content is reduced to silver metal.

5. The photosensitive reducible silver ion-containing composition of claim 1 , wherein P is a 6-membered N-heteroaromatic compound.

6. The photosensitive reducible silver ion-containing composition of claim 1 , wherein P is a 5- or 6-membered N-heteroaromatic compound selected from the group consisting of pyridine, 2-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine, 2,3-dimethylpyridine, 3,4-dimethylpyridine, 4-pyridylacetone, 3-chloropyridine, 3-fluoropyridine, oxazole, 4-methyloxazole, isoxazole, 3-methylisoxazole, pyrimidine, pyrazine, pyridazine, and thiazole.

7. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has an oxidation potential of at least 1.0 V vs. saturated calomel electrode (SCE); the α-oxy carboxylate has a first oxidation potential of at least 1.2 V vs. saturated calomel electrode (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. saturated calomel electrode (SCE).

8. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the 5- or 6-membered N-heteroaromatic compound has an oxidation potential of at least 1.5 V vs. saturated calomel electrode (SCE).

9. The photosensitive reducible silver ion-containing composition 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.

Assignments (9)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0233 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 30, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; PFC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049901/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
SECURITY INTEREST Recorded Nov 16, 2016
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA N.A.
Reel/Frame 040340/0193 →
SECURITY INTEREST Recorded Nov 16, 2016
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: JP MORGAN CHASE BANK, N.A.
Reel/Frame 040340/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 9, 2016
From: SHUKLA, DEEPAK
To: EASTMAN KODAK COMPANY
Reel/Frame 039377/0347 →
Continuity (1)
Related Publication 20180047476A1 · Feb 15, 2018