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US5380807A Expired / Lapsed US ⏱️ 0.0 years remaining

Electrically conductive alternating copolymer and method of preparing such a copolymer

Assignee: US Philips Corp
•
Filing: 1993-01-08
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Granted: 1995-01-10
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Expires: 2013-01-08
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Abstract

Abstract Polycondensation of, for example, squaric acid with a benzodihydropyrrole, benzodithiazole, neocuproine, terthienyl or an aromatic diamine gives a semiconductive alternating copolymer having a small band gap. It is alternatively possible to use croconic acid or 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone instead of squaric acid. An alternating copolymer of croconic acid and a methyl-substituted benzodithiazole has the following repetititve unit: ##STR1##

Inventors

  • 👤 Edsko E. Havinga
  • 👤 Wolter ten Hoeve
  • 👤 Hans Wijnberg

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 10:05
CPC Classifications
C; C08; C08F; C08F234/00; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/127; C08G; C08G61/00; C08G61/12; C08G73/00; C08G73/06; C08G73/0683; C08G73/0688; H01B1/128

Claims Analysis

Total Claims: 31
Claim 1
Independent Claim 114 words
A (semi)conductive copolymer of alternating donor and acceptor monomer units, characterized in that the (semi)conductive copolymer is obtained by reacting an acceptor monomer unit A having an unsaturated ring structure which is substituted with at least two double-bonded oxygen atoms and at least one hydroxy group, with a donor monomer unit D formed by a homo or heterocyclic aromatic compound comprising at least two active hydrogen atoms, a polycondensation reaction taking place in the presence of a solvent, thereby forming said alternating (semi)conductive copolymer substantially free of doping, with the proviso that said monomer unit A is selected from the group consisting of croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone when said monomer unit D is p-phenylenediamine.
Claim 2
Dependent Claim 114 words
A (semi)conductive copolymer of alternating donor and acceptor monomer units, characterized in that the (semi)conductive copolymer is obtained by reacting an acceptor monomer unit A having an unsaturated ring structure which is substituted with at least two double-bonded oxygen atoms and at least one hydroxy group, with a donor monomer unit D formed by a homo or heterocyclic aromatic compound comprising at least two active hydrogen atoms, a polycondensation reaction taking place in the presence of a solvent, thereby forming said alternating (semi)conductive copolymer substantially free of doping, with the proviso that said monomer unit A is selected from the group consisting of croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone when said monomer unit D is p-phenylenediamine.
Claim 3
Dependent Claim 28 words
An alternating copolymer as claimed in claim 1, characterized in that the monomer unit A is selected from the group consisting of squaric acid, croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone.
Claim 4
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 2, wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 5
Dependent Claim 94 words
An alternating copolymer as claimed in claim 1, characterized in that the monomer unit D is selected from the group consisting of ##STR2## where: X 1 =--NR-- and X 2 =O, S, Se, --NR--, --CR═CH--, --CHR--CH 2 -- or --C(alkyl) 2 --, where the alkyl group contains 1-8 C-atoms and X 3 =--CR═ or --N═, where R is and H-atom or a C 1 -C 18 alkyl or alkoxy group; or X 1 =S or O and X 2 = or --CR═CH-- and X 3 =--CR═ or --N═, where R has the above-mentioned meaning.
Claim 6
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 4, wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 7
Dependent Claim 23 words
An alternating copolymer as claimed in claim 4, characterized in that the monomer unit D is selected from the group consisting of ##STR3##
Claim 8
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 3, wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 9
Dependent Claim 41 words
An alternating copolymer as claimed in claim 6, characterized in that the monomer unit A is croconic acid and the monomer unit D corresponds to formula VII, where R 3 represents a methyl group and R 4 represents a dodecyl group.
Claim 10
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 8, wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 11
Dependent Claim 124 words
An alternating copolymer as claimed in claim 1, characterized in that the monomer unit A is selected from the group consisting of croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone and the monomer unit D is an aromatic diamine of the general formula ##STR4## where R 6 and R 7 represent an H-atom or a C 1 -C 18 alkyl group and A is an aromatic core selected from the group consisting of ##STR5## where R 8 and R 9 represent an H-atom or a C 1 -C 18 alkyl group and X 1 =--N═ or --CR═, where R represents an H-atom or a C 1 -C 18 alkyl or alkoxy group, and X 2 =S, O, Se, --NH-- or --N(alkyl)--, where the alkyl group contains 1-18 C-atoms.
Claim 12
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 10, wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 13
Dependent Claim 27 words
An alternating copolymer as claimed in claim 10, characterized in that the monomer unit D is selected from the group consisting of p-phenylenediamine, thionine and 3,6-diamino acridine.
Claim 14
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 12, wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 15
Dependent Claim 13 words
An electronic circuit which comprises an alternating copolymer as claimed in claim 1.
Claim 16
Dependent Claim 18 words
An electronic circuit as claimed in claim 14 in which said copolymer is present as a semiconductor element.
Claim 17
Dependent Claim 13 words
An antistatic layer which comprises an alternating copolymer as claimed in claim 1.
Claim 18
Dependent Claim 14 words
An electromagnetic protective layer which comprises an alternating copolymer as claimed in claim 1.
Claim 19
Dependent Claim 112 words
An alternating copolymer as claimed in claim 1, wherein the monomer unit A is squaric acid and the monomer unit D is an aromatic diamine of the general formula ##STR6## where R 6 and R 7 represent a C 1 -C 18 alkyl group and Ar is an aromatic core selected from the group consisting of ##STR7## where R 8 and R 9 represent an H-atom or a C 1 -C 18 alkyl group and X 1 =--N═ or --CR═, where R represents an H-atom or a C 1 -C 18 alkyl or alkoxy group, and X 2 =S, O, Se, --NH-- or --N (alkyl)--, where the alkyl group contains 1-18 C-atoms.
Claim 20
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 18 wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 21
Dependent Claim 26 words
An alternating copolymer as claimed in claim 18, characterized in that the monomer unit D is selected from the group consisting of thionine and 3,6-diamino acridine.
Claim 22
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 20 wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 23
Dependent Claim 46 words
A method of preparing an alternating copolymer as claimed in claim 1, in which equimolar quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 24
Dependent Claim 142 words
A (semi)conductive copolymer of alternating donor and acceptor monomer units, characterized in that the (semi)conductive copolymer is obtained by reacting an acceptor monomer unit A selected from the group consisting of squaric acid, croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone with a donor monomer unit D selected from the group consisting of ##STR8## where: X 1 =--NR-- and X 2 =O, S, Se, --NR--, --CR═CH--, --CHR--CH 2 -- or --C(alkyl) 2 --, where the alkyl group contains 1-18 C-atoms and X 3 =--CR═ or --N═, where R is an H-atom or a C 1 -C 18 alkyl or alkoxy group; or X 1 =S or O and X 2 = or --CR═CH-- and X 3 =--CR═ or --N═, where R has the above-mentioned meaning, a polycondensation reaction taking place in the presence of a solvent, thereby forming said alternating (semi)conductive copolymer substantially free of doping.
Claim 25
Dependent Claim 142 words
A (semi)conductive copolymer of alternating donor and acceptor monomer units, characterized in that the (semi)conductive copolymer is obtained by reacting an acceptor monomer unit A selected from the group consisting of squaric acid, croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone with a donor monomer unit D selected from the group consisting of ##STR8## where: X 1 =--NR-- and X 2 =O, S, Se, --NR--, --CR═CH--, --CHR--CH 2 -- or --C(alkyl) 2 --, where the alkyl group contains 1-18 C-atoms and X 3 =--CR═ or --N═, where R is an H-atom or a C 1 -C 18 alkyl or alkoxy group; or X 1 =S or O and X 2 = or --CR═CH-- and X 3 =--CR═ or --N═, where R has the above-mentioned meaning, a polycondensation reaction taking place in the presence of a solvent, thereby forming said alternating (semi)conductive copolymer substantially free of doping.
Claim 26
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 23 wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 27
Dependent Claim 184 words
A (semi)conductive copolymer of alternating donor and acceptor monomer units, characterized in that the (semi)conductive copolymer is obtained by reacting an acceptor monomer unit A selected from the group of squaric acid, croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone with a donor monomer unit D selected from an aromatic diamine of the general formula ##STR9## where R 6 and R 7 represent an H-atom or a C 1 -C 18 alkyl group and Ar is an aromatic core selected from the group consisting of ##STR10## where R 8 and R 9 represent an H-atom or a C 1 -C 18 alkyl group and X 1 =--N═ or --CR═, where R represents an H-atom or a C 1 -C 18 alkyl or alkoxy group, and X 2 =S, O, Se, --NH-- or --N (alkyl)--, where the alkyl group contains 1-18 C-atoms, with the proviso that said monomer unit A is selected from the group consisting of croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetratone when said monomer unit D is p-phenylenediamine, a polycondensation reaction taking place in the presence of a solvent, thereby forming said alternating (semi)conductive copolymer substantially free of doping.
Claim 28
Dependent Claim 184 words
A (semi)conductive copolymer of alternating donor and acceptor monomer units, characterized in that the (semi)conductive copolymer is obtained by reacting an acceptor monomer unit A selected from the group of squaric acid, croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone with a donor monomer unit D selected from an aromatic diamine of the general formula ##STR9## where R 6 and R 7 represent an H-atom or a C 1 -C 18 alkyl group and Ar is an aromatic core selected from the group consisting of ##STR10## where R 8 and R 9 represent an H-atom or a C 1 -C 18 alkyl group and X 1 =--N═ or --CR═, where R represents an H-atom or a C 1 -C 18 alkyl or alkoxy group, and X 2 =S, O, Se, --NH-- or --N (alkyl)--, where the alkyl group contains 1-18 C-atoms, with the proviso that said monomer unit A is selected from the group consisting of croconic acid and 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetratone when said monomer unit D is p-phenylenediamine, a polycondensation reaction taking place in the presence of a solvent, thereby forming said alternating (semi)conductive copolymer substantially free of doping.
Claim 29
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 25 wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.
Claim 30
Dependent Claim 25 words
An alternating copolymer as claimed in claim 25 wherein the monomer unit D is selected from the group consisting of p-phenylenediamine, thionine and 3,6-diamino acridine.
Claim 31
Dependent Claim 45 words
A method of preparing an alternating copolymer as claimed in claim 27 wherein equimolor quantities of bifunctional acceptor monomer units A and bifunctional donor monomer units D are mixed in a solvent and polymerized by polycondensation, thereby forming the alternating copolymer comprising repeating unit AD.

References Cited (Backward Citations)

DE3246319A1 Cited

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