Patent US5514878A successfully refreshed from Google Patents.
US5514878A
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Polymers for electroluminescent devices
Assignee: Cambridge Display Technology Ltd
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Filing: 1994-03-18
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Granted: 1996-05-07
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Expires: 2014-03-18
Abstract
Abstract This invention provides semiconductive conjugated polymers incorporating electron-withdrawing groups for use in electroluminescent devices, methods for their manufacture, and electroluminescent devices incorporating the polymers. The electron-withdrawing group is conjugatively linked to the polymer chain and is selected so that the polymer exhibits electroluminesence upon application of an electric field to a layer thereof.
Inventors
- 👤 Andrew B. Holmes
- 👤 Richard H. Friend
- 👤 Stephen C. Moratti
- 👤 Derek R. Baigent
- 👤 Donald C. Bradley
- 👤 Raoul Cervini
- 👤 Neil C. Greenham
- 👤 Peter J. Hamer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:44
CPC Classifications
H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/128; C; C08; C08G; C08G61/00; C09; C09K; C09K11/00; C09K11/06; H01B1/127; H05; H05B; H05B33/00; H05B33/10; H05B33/12; H05B33/14; H05B33/26
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
78 words
A semiconductive conjugated polymer comprising arylene vinylene units forming at least part of the polymer main chain in which a solubilising group is present on at least some of the arylene moieties so as to render the polymer solution processible, and an electron-withdrawing group is conjugatively linked to the polymer main chain, wherein the solubilising group and the electron-withdrawing group are selected so that the polymer exhibits electroluminescence upon application of an electric field to a layer thereof.
Claim 2
Dependent Claim
78 words
A semiconductive conjugated polymer comprising arylene vinylene units forming at least part of the polymer main chain in which a solubilising group is present on at least some of the arylene moieties so as to render the polymer solution processible, and an electron-withdrawing group is conjugatively linked to the polymer main chain, wherein the solubilising group and the electron-withdrawing group are selected so that the polymer exhibits electroluminescence upon application of an electric field to a layer thereof.
Claim 3
Dependent Claim
23 words
A semiconductive conjugated polymer according to claim 1, wherein the electron-withdrawing group is conjugatively linked to at least some of the vinylene moieties.
Claim 4
Dependent Claim
22 words
A semiconductive conjugated polymer according to claim 1, wherein the electron-withdrawing group is selected to modulate the optical properties of the polymer.
Claim 5
Dependent Claim
23 words
A semiconductive conjugated polymer according to claim 3, wherein the electron-withdrawing group is selected to modulate the wavelength of radiation emitted in electroluminescence.
Claim 6
Dependent Claim
32 words
A semiconductive conjugated polymer according to claim 1, wherein the electron-withdrawing group comprises a nitrile group, an ester group, an acid amide, a sulfone, a sulfoxide, a trifluoromethyl or a ketone group.
Claim 7
Dependent Claim
24 words
A semiconductive conjugated polymer according to claim 1, wherein the solubilising group comprises an alkoxy or alkyl group with 4 or more carbon atoms.
Claim 8
Dependent Claim
19 words
A semiconductive conjugated polymer according to claim 1, wherein the polymer is a substantially fully conjugated poly(arylene vinylene) polymer.
Claim 9
Dependent Claim
45 words
A semiconductive conjugated polymer according to claim 7, having the following general formula: Ar-vinylene-Ar'-vinylene!.sub.n in which Ar and Ar' are the same or different and represent arylene groups, each vinylene is substituted with the electron withdrawing group X, and n represents the degree of polymerisation.
Claim 10
Dependent Claim
76 words
A semiconductive conjugated polymer, having the general formula: Ar--CX═CH--Ar'--CH═CX!.sub.n wherein Ar and Ar' are the same or different and represent arylene groups, each vinylene is substituted with an electron withdrawing group X, n represents the degree of polymerisation and a solubilising group is present on at least some of the arylene groups so as to render the polymer solution processible; and wherein the polymer exhibits electroluminscence upon application of an electric field to a layer thereof.
Claim 11
Dependent Claim
76 words
A semiconductive conjugated polymer, having the general formula: Ar--CX═CH--Ar'--CH═CX!.sub.n wherein Ar and Ar' are the same or different and represent arylene groups, each vinylene is substituted with an electron withdrawing group X, n represents the degree of polymerisation and a solubilising group is present on at least some of the arylene groups so as to render the polymer solution processible; and wherein the polymer exhibits electroluminscence upon application of an electric field to a layer thereof.
Claim 12
Dependent Claim
22 words
A semiconductive conjugated polymer according to claim 9, wherein Ar and Ar' are both 2,5 dihexyloxy phenylene moieties and X is CN.
Claim 13
Dependent Claim
22 words
A semiconductive conjugated polymer according to claim 9, wherein Ar is 2-dodecyloxy,5-methylthio phenylene, Ar' is 2,5 dihexyloxy phenylene, and X is CN.
Claim 14
Dependent Claim
19 words
A semiconductive conjugated polymer according to claim 9, wherein Ar is 2,6-dihexyloxy naphthalene and Ar' is 2,5 dihexyloxy phenylene.
Claim 15
Dependent Claim
21 words
A semiconductive conjugated polymer according to claim 9, wherein Ar is a 2,5 dihexyloxy phenylene and Ar' is a dodecyl-substituted thiophene.
Claim 16
Dependent Claim
84 words
A semiconductive conjugated polymer comprising: (i) conjugated regions incorporating arylene vinylene units forming part of the polymer main chain in which a solubilising group is present on at least some of the arylene moieties so as to render the polymer solution processible, and an electron-withdrawing group is conjugatively linked to the polymer main chain; and (ii) unconjugated regions, wherein the solubilising group and the electron-withdrawing group are selected so that the polymer exhibits electroluminescence upon application of an electric field to a layer thereof.
Claim 17
Dependent Claim
84 words
A semiconductive conjugated polymer comprising: (i) conjugated regions incorporating arylene vinylene units forming part of the polymer main chain in which a solubilising group is present on at least some of the arylene moieties so as to render the polymer solution processible, and an electron-withdrawing group is conjugatively linked to the polymer main chain; and (ii) unconjugated regions, wherein the solubilising group and the electron-withdrawing group are selected so that the polymer exhibits electroluminescence upon application of an electric field to a layer thereof.
Claim 18
Dependent Claim
21 words
A semiconductive conjugated polymer according to claim 14, wherein the conjugated regions comprise distyrylbenzene moieties which incorporate the arylene vinylene units.
Claim 19
Dependent Claim
38 words
A semiconductive conjugated polymer according claim 15, having the following general formula: ##STR15## in which at least one of R and R' is a solubilising group, X is the electron-withdrawing group, and R" is an aliphatic linker group.
Claim 20
Dependent Claim
27 words
A semiconductive conjugated polymer according to claim 16, wherein R and R' are both hexyloxy groups, X is CN and R" is --O--(CH 2 ) 8 --O--.
Claim 21
Dependent Claim
87 words
A method of making a semiconductive conjugated polymer according to claim 1, which method comprises reacting a first compound of general formula X--CH.sub.2 --Ar--CH.sub.2 --X with a second compound of general formula ORC--Ar'--CRO under conditions to produce a polymer comprising at least some regions of --Ar--CX═RC--Ar'--CR═CX-- in which Ar and Ar' are the same or different and represent arylene moieties or arylene containing moieties, at least some of which are substituted with a solubilising group, X is an electron-withdrawing group and R is alkyl, aryl or hydrogen.
Claim 22
Dependent Claim
14 words
A method according to claim 18, wherein the reaction is performed under base catalysis.
Claim 23
Dependent Claim
19 words
A method according to claim 19, wherein the base is selected from potassium t-butoxide, tetra-N-butylammonium hydroxide and mixtures thereof.
Claim 24
Dependent Claim
20 words
A method according to claim 18, which is performed in the presence of t-butyl alcohol, and/or THF as solvent components.
Claim 25
Dependent Claim
17 words
A method according to claim 18, which is performed in the temperature range 20° to 60° C.
Claim 26
Dependent Claim
10 words
A method according to claim 18, wherein R is hydrogen.
Claim 27
Dependent Claim
28 words
A method according to claim 18, wherein X comprises a nitrile group, an ester group, an acid amide, a sulfone, a sulfoxide, a trifluoromethyl or a ketone group.
Claim 28
Dependent Claim
22 words
A method according to claim 18, wherein the solubilising group comprises an alkoxy or alkyl group with 4 or more carbon atoms.
Claim 29
Dependent Claim
18 words
A method according to claim 18, wherein Ar and Ar' are both 2,5-dihexyloxyphenylene moieties and X is CN.
Claim 30
Dependent Claim
19 words
A method according to claim 18, wherein Ar 2-dodecyloxy,5-methylthio phenylene, Ar' is 2,5 dihexyloxy phenylene, and X is CN.
Claim 31
Dependent Claim
16 words
A method according to claim 18, wherein Ar is 2,6-dihexyloxynaphthylene and Ar' is 2,5 dihexyloxy phenylene.
Claim 32
Dependent Claim
19 words
A method according to claim 18, wherein Ar is a 2,5 dihexyloxy phenylene and Ar' is a dodecyl-substituted thiophene.
Claim 33
Dependent Claim
33 words
A method according to claim 18, wherein Ar' comprises the unit Ar"-R"-Ar"' in which Ar" and Ar"' are the same or different and represent arylene moieties, and R" represents an aliphatic linker group.
Claim 34
Dependent Claim
25 words
A method according to claim 30, wherein Ar" and Ar"' are both p phenylene, X is CN and R" is --O--(CH 2 ) 8 --O--.
Claim 35
Dependent Claim
117 words
An electroluminescent device comprising a semiconductive layer which comprises an emissive layer of semiconductive conjugated polymer, a first contact layer in contact with a first surface of the semiconductive layer, and a second contact layer in contact with a second surface of the semiconductor layer, wherein the polymer comprises arylene vinylene units forming at least part of the polymer main chain, on which is present a solubilising group so as to render the polymer solution processible, and an electron-withdrawing group is conJugatively linked to the polymer main chain, wherein the solubilising group and the electron-withdrawing group are selected so that the polymer emits radiation upon application of an electric field between the first and second contact layers.
Claim 36
Dependent Claim
117 words
An electroluminescent device comprising a semiconductive layer which comprises an emissive layer of semiconductive conjugated polymer, a first contact layer in contact with a first surface of the semiconductive layer, and a second contact layer in contact with a second surface of the semiconductor layer, wherein the polymer comprises arylene vinylene units forming at least part of the polymer main chain, on which is present a solubilising group so as to render the polymer solution processible, and an electron-withdrawing group is conJugatively linked to the polymer main chain, wherein the solubilising group and the electron-withdrawing group are selected so that the polymer emits radiation upon application of an electric field between the first and second contact layers.
Claim 37
Dependent Claim
18 words
An electroluminescent device according to claim 32, wherein the semiconductive conjugated polymer is as defined for claim 1.
Claim 38
Dependent Claim
18 words
An electroluminescent device according to claim 32, wherein the semiconductive conjugated polymer is as defined for claim 9.
Claim 39
Dependent Claim
18 words
An electroluminescent device according to claim 32, wherein the semiconductive conjugated polymer is as defined for claim 14.
Claim 40
Dependent Claim
38 words
An electroluminescent device according to claim 32, wherein the semiconductive layer further comprises a hole-transporting polymer layer between the emissive layer and the first contact layer, which hole-transporting polymer layer matches the first contact layer for hole injection.
Claim 41
Dependent Claim
25 words
An electroluminescent device according to claim 36, wherein the first contact layer comprises indium-tin oxide and the hole transporting polymer comprises poly(paraphenylenevinylene), polythiophene or polyphenylene.
Claim 42
Dependent Claim
21 words
An electroluminescent device according to claim 32, wherein the second contact layer comprises a metal selected from calcium, aluminium and gold.
Claim 43
Dependent Claim
14 words
An electroluminescent device according to claim 38, wherein the second contact layer comprises aluminum.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-05-07 | 1999-11-06 | 2000-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-05-07 | 2003-11-06 | 2004-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-05-07 | 2007-11-06 | 2008-05-07 | $7700.00 | Window Closed / Lapsed |