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US4046950A Expired / Lapsed US ⏱️ 0.0 years remaining

Chalcogenated tetracene organic metals

Assignee: Eastman Kodak Co
•
Filing: 1976-03-18
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Granted: 1977-09-06
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Expires: 1996-03-18
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Abstract

Abstract Organic ion-radical salts having the electrical properties of metals and elements having a layer containing these salts are disclosed. The salts are salts of a chalcogenated tetracene donor compound and an electron acceptor compound wherein the ratio of donor compound to acceptor compound is from about 3:1 to about 1.5:1. These salts have a resistivity less than about 10 -2 ohm-cm at 295° K. The salts are further characterized by a resistivity that decreases with decreasing temperature. A vapor phase process for preparing these organic metals is also disclosed. The process comprises the steps of: 1. forming a first vapor comprising the chalcogenated tetracene compound; 2. forming a second vapor comprising the electron acceptor compound; and 3. reacting the first vapor with the second vapor at a temperature of about 75° C to about 300° C in a substantially inert atmosphere.

Inventors

  • 👤 Lawrence Clair Isett

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 15:33
CPC Classifications
D; D06; D06M; D06M23/00; C; C09; C09K; C09K3/00; C09K3/16; G; G03; G03C; G03C1/00; G03C1/76; G03C1/85; G03G; G03G5/00; G03G5/10; G11; G11B; G11B5/00; G11B5/62; G11B5/68; G11B5/70; G11B5/72; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/121

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 215 words
A composition of matter comprising an ion-radical of the formula (D.sub.x).sup.n.spsp.+ (A).sup.n.spsp.- wherein (D x ) n .spsp.+ is a chalcogenated tetracene complex cation selected from the group consisting of complex cations of tetrathiotetracene, tetraselenotetracene and tetratellurotetracene and A is an anion selected from the group consisting of a. an inorganic anion selected from the group consisting of Br 3 - , I 3 - , F - , Cl - , Br - , I - , SCN - , nitrate, sulfate, phosphate, fluoroborate, ferricyanide, molybdate, tungstate; and b. an organic anion derived from an organic acid selected from the group consisting of: an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid, an aliphatic polycarboxylic acid, an unsaturated carboxylic acid, an aromatic carboxylic acid, a sulfonic acid, a heterocyclic acid containing from 5 to 6 atoms in the heterocyclic nucleus and having at least one hetero atom selected from the group consisting of a nitrogen, oxygen, or sulfur atom; a monohydric phenol, and a polyhydric phenol; and x represents the ratio of D to A and has a value between about 3 and about 1.5 and n is an integer between 1 and 5, said salt having an electrical resistivity less than about 10 -2 ohm-cm at 295° K said resistivity decreasing with decreasing temperature.
Claim 2
Dependent Claim 215 words
A composition of matter comprising an ion-radical of the formula (D.sub.x).sup.n.spsp.+ (A).sup.n.spsp.- wherein (D x ) n .spsp.+ is a chalcogenated tetracene complex cation selected from the group consisting of complex cations of tetrathiotetracene, tetraselenotetracene and tetratellurotetracene and A is an anion selected from the group consisting of a. an inorganic anion selected from the group consisting of Br 3 - , I 3 - , F - , Cl - , Br - , I - , SCN - , nitrate, sulfate, phosphate, fluoroborate, ferricyanide, molybdate, tungstate; and b. an organic anion derived from an organic acid selected from the group consisting of: an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid, an aliphatic polycarboxylic acid, an unsaturated carboxylic acid, an aromatic carboxylic acid, a sulfonic acid, a heterocyclic acid containing from 5 to 6 atoms in the heterocyclic nucleus and having at least one hetero atom selected from the group consisting of a nitrogen, oxygen, or sulfur atom; a monohydric phenol, and a polyhydric phenol; and x represents the ratio of D to A and has a value between about 3 and about 1.5 and n is an integer between 1 and 5, said salt having an electrical resistivity less than about 10 -2 ohm-cm at 295° K said resistivity decreasing with decreasing temperature.
Claim 3
Dependent Claim 15 words
The composition of matter of claim 1 wherein said chalcogenated tetracene complex cation is tetrathiotetracene.
Claim 4
Dependent Claim 13 words
The composition of matter of claim 2 wherein said anion is a halogen.
Claim 5
Dependent Claim 12 words
The composition of matter of claim 3 wherein said halogen is iodine.
Claim 6
Dependent Claim 13 words
The composition of matter (tetrathiotetracene 2 ) + (I 3 ) - .
Claim 7
Dependent Claim 13 words
The composition of matter (tetrathiotetracene 2 ) + (I 3 ) - .
Claim 8
Dependent Claim 16 words
An element comprising a support having thereon a layer containing the ion-radical salt of claim 2.
Claim 9
Dependent Claim 19 words
An element according to claim 6 wherein said chalcogenated tetracene complex cation of said ion radical salt is tetrathiotetracene.
Claim 10
Dependent Claim 16 words
An element according to claim 6 wherein said anion of said ion-radical salt is a halogen.
Claim 11
Dependent Claim 11 words
An element according to claim 8 wherein said halogen is iodine.
Claim 12
Dependent Claim 16 words
An element according to claim 6 wherein said layer comprises a binder and said ion-radical salt.
Claim 13
Dependent Claim 19 words
An element according to claim 6 wherein said ion-radical salt is in the form of a binderless thin film.
Claim 14
Dependent Claim 17 words
An element according to claim 11 having a thickness of about 0.05 μm to about 5 μm.
Claim 15
Dependent Claim 20 words
An element according to claim 6 wherein said ion-radical salt is (tetrathiotetracene 2 ) + (I 3 ) - .
Claim 16
Dependent Claim 249 words
A process for preparing an ion-radical salt wherein said ion-radical salt is represented by the formula (D.sub.x).sup.n.spsp.+ (A).sup.n.spsp.- wherein (D x ) n .spsp.+ is a chalcogenated tetracene complex cation selected from the group consisting of complex cations of tetrathiotetracene, tetraselenotetracene and tetratellurotetracene and A is an anion selected from the group consisting of a. an inorganic anion selected from the group consisting of Br 3 - , I 3 - , F - , Cl - , Br - , I - , SCN - , nitrate, sulfate, phosphate, fluoroborate, ferricyanide, molybdate, tungstate; and b. an organic anion derived from an organic acid selected from the group consisting of: an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid, an aliphatic polycarboxylic acid, an unsaturated carboxylic acid, an aromatic carboxylic acid, a sulfonic acid, a heterocyclic acid containing from 5 to 6 atoms in the heterocyclic nucleus and having at least one hetero atom selected from the group consisting of a nitrogen, oxygen, or sulfur atom; a monohydric phenol, and a polyhydric phenol; and x represents the ratio of D to A and has a value between about 3 and about 1.5 and n is an integer between 1 and 5 comprising the steps of 1. forming a first vapor comprising said chalcogenated tetracene complex cation; 2. forming a second vapor comprising said anion; and 3. reacting said first vapor with said second vapor at a temperature of about 75° C to about 300° C in a substantially inert atmosphere.
Claim 17
Dependent Claim 249 words
A process for preparing an ion-radical salt wherein said ion-radical salt is represented by the formula (D.sub.x).sup.n.spsp.+ (A).sup.n.spsp.- wherein (D x ) n .spsp.+ is a chalcogenated tetracene complex cation selected from the group consisting of complex cations of tetrathiotetracene, tetraselenotetracene and tetratellurotetracene and A is an anion selected from the group consisting of a. an inorganic anion selected from the group consisting of Br 3 - , I 3 - , F - , Cl - , Br - , I - , SCN - , nitrate, sulfate, phosphate, fluoroborate, ferricyanide, molybdate, tungstate; and b. an organic anion derived from an organic acid selected from the group consisting of: an aliphatic monocarboxylic acid, an aliphatic dicarboxylic acid, an aliphatic polycarboxylic acid, an unsaturated carboxylic acid, an aromatic carboxylic acid, a sulfonic acid, a heterocyclic acid containing from 5 to 6 atoms in the heterocyclic nucleus and having at least one hetero atom selected from the group consisting of a nitrogen, oxygen, or sulfur atom; a monohydric phenol, and a polyhydric phenol; and x represents the ratio of D to A and has a value between about 3 and about 1.5 and n is an integer between 1 and 5 comprising the steps of 1. forming a first vapor comprising said chalcogenated tetracene complex cation; 2. forming a second vapor comprising said anion; and 3. reacting said first vapor with said second vapor at a temperature of about 75° C to about 300° C in a substantially inert atmosphere.
Claim 18
Dependent Claim 27 words
A process according to claim 14 wherein said first vapor and said second vapor are reacted at a temperature of about 200° C to about 300° C.
Claim 19
Dependent Claim 24 words
A process according to claim 14 wherein said inert atmosphere comprises an inert gas selected from the group consisting of argon, nitrogen, and helium.
Claim 20
Dependent Claim 16 words
A process according to claim 14 wherein said reaction is carried out in a tube furnace.
Claim 21
Dependent Claim 16 words
A process according to claim 14 wherein said reaction is carried out in a flow reactor.
Claim 22
Dependent Claim 24 words
A process according to claim 14 wherein the total pressure during the reaction step is from about 10 -5 torr to about 150 torr.
Claim 23
Dependent Claim 48 words
A process for preparing (tetrathiotetracene 2 ) + (I 3 ) - comprising the steps of: 1. forming a vapor of tetrathiotetracene; 2. forming a vapor of iodine; and 3. reacting the tetrathiotetracene vapor with the iodine vapor at a temperature of about 225° C in a vacuum.
Claim 24
Dependent Claim 48 words
A process for preparing (tetrathiotetracene 2 ) + (I 3 ) - comprising the steps of: 1. forming a vapor of tetrathiotetracene; 2. forming a vapor of iodine; and 3. reacting the tetrathiotetracene vapor with the iodine vapor at a temperature of about 225° C in a vacuum.

References Cited (Backward Citations)

US3403165A Cited
US3629158A Cited
US3634336A Cited
US3627655A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-09-05 1981-03-07 1981-09-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-09-05 1985-03-07 1985-09-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-09-05 1989-03-07 1989-09-06 $7700.00 Window Closed / Lapsed

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