US4349664A
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Doped acetylene polymer and process for production thereof
Assignee: JSR Corp
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Filing: 1980-07-09
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Granted: 1982-09-14
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Expires: 2000-07-09
Abstract
Abstract Doped acetylene polymers are produced by immersing an acetylene polymer under an inert gas atmosphere in an organic solvent solution of a dopant selected from the group consisting of a platinum group metal complex, a carbonium salt, an oxonium salt and a parabenzoquinone derivative. According to this process, a doped acetylene polymer having any desired electrical conductivity can be produced and the doped acetylene polymer thus obtained has excellent properties as an organic semiconductor material for solar batteries, various sensors, etc.
Inventors
- 👤 Yoshio Matsumura
- 👤 Ikuo Nozue
- 👤 Takashi Ukachi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:58
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/0008; C08K5/56; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/125; H10; H10K; H10K85/00; H10K85/10; H10K85/141; H10K85/143; H10K99/00; Y; Y02; Y02E; Y02E10/00; Y02E10/50; Y02E10/549
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
28 words
An acetylene polymer doped with a dopant selected from the group consisting of a platinum group metal complex, a carbonium salt, an oxonium salt and a parabenzoquinone derivative.
Claim 2
Dependent Claim
28 words
An acetylene polymer doped with a dopant selected from the group consisting of a platinum group metal complex, a carbonium salt, an oxonium salt and a parabenzoquinone derivative.
Claim 3
Dependent Claim
93 words
A doped acetylene polymer according to claim 1, wherein the dopant is a platinum group metal complex selected from the group consisting of (PhCN) 2 PdCl 4 ,(COD)PdCl 2 , [(C 2 H 4 )PdCl 2 ] 2 , (Ph 4 C 4 )PdCl 2 , (COD)PtCl 2 , K[PtCl 3 (C 2 H 4 )]H 2 O, [Pt(C 2 H 4 )Cl 2 ] 2 , (PhCN) 2 PtCl 2 , [(C 2 H 4 )RhCl] 2 and Ru(COD)Cl 2 wherein COD stands for 1,5-cyclooctadiene and Ph 4 C 4 for tetraphenylcyclobutadiene.
Claim 4
Dependent Claim
15 words
A doped acetylene polymer according to claim 1, wherein the dopant is a palladium complex.
Claim 5
Dependent Claim
26 words
A doped acetylene polymer according to claim 3, wherein the dopant is (PhCN) 2 PdCl 2 or [(C 2 H 4 )PdCl 2 ] 2 .
Claim 6
Dependent Claim
130 words
A doped acetylene polymer according to claim 1, wherein the dopant is a combination of an anion selected from the group consisting of BF 4 - , AlCl 4 - , FeCl 4 - , SnCl 5 - , PF 6 - , PCl 6 - , SbCl 6 - , SbF 6 - , ClO 4 - , CF 3 SO 3 - and CF 3 CO 2 - with a cation selected from the group consisting of triphenylmethyl ion [(C 6 H 5 ) 3 C + ], tropylium ion (C 7 H 7 + ), acyl ion (RCO + ), triethyloxonium ion [(C 2 H 5 ) 3 O + ], and dialkoxycarbonium ion [RC(OR')(OR") + ] in which R, R' and R" stand for organic groups.
Claim 7
Dependent Claim
62 words
A doped acetylene polymer according to claim 1, wherein the dopant is a combination of an anion selected from the group consisting of BF 4 - and ClO 4 - with a cation selected from the group consisting of triphehylmethyl ion [(C 6 H 5 ) 3 C + ] and triethyloxonium ion [(C 2 H 5 ) 3 O + ].
Claim 8
Dependent Claim
27 words
A doped acetylene polymer according to claim 1, wherein the dopant is a parabenzoquinone derivative selected from the group consisting of 2,3-dicyano-5-chloroparabenzoquinone, 2,3-dichlorodicyanoparabenzoquinone, 2,3-dicyano-5-phenylsulfonylparabenzoquinone, 2,3-dicyano-5-chloro-6-phenylparabenzoquinone and 2,3,5,6-tetracyanoparabenzoquinone.
Claim 9
Dependent Claim
46 words
A doped acetylene polymer according to claim 1, wherein the parabenzoquinone derivative has a first half wave reduction potential (-E1/2) of less than -0.2 V as measured at 25° C. by means of a saturated calomel electrode using LiClO 4 in acetonitrile as the supporting electrolyte.
Claim 10
Dependent Claim
24 words
A doped acetylene polymer according to any one of claims 1 or 2, wherein the starting acetylene polymer is in the form of film.
Claim 11
Dependent Claim
48 words
A process for producing a doped acetylene polymer which comprises immersing an acetylene polymer under an inert gas atmosphere in an organic solvent solution of a dopant selected from the group consisting of a platinum group metal complex, a carbonium salt, an oxonium salt and a parabenzoquinone derivative.
Claim 12
Dependent Claim
48 words
A process for producing a doped acetylene polymer which comprises immersing an acetylene polymer under an inert gas atmosphere in an organic solvent solution of a dopant selected from the group consisting of a platinum group metal complex, a carbonium salt, an oxonium salt and a parabenzoquinone derivative.
Claim 13
Dependent Claim
17 words
A process according to claim 1, wherein the immersion is carried out at 10° to 70° C.
Claim 14
Dependent Claim
96 words
A process according to claim 10, wherein the dopant is a platinum group metal complex selected from the group consisting of (PhCN) 2 PdCl 2 , (COD)PdCl 2 , [(C 2 H 4 )PdCl 2 ] 2 , (Ph 4 C 4 )PdCl 2 , (COD)PtCl 2 , K[PtCl 3 (C 2 H 4 )]H 2 O, [Pt(C 2 H 4 )Cl 2 ] 2 , (PhCN) 2 PtCl 2 , [(C 2 H 4 ) 2 RhCl] 2 , and Ru(COD)Cl 2 , wherein COD stands for 1,5-cyclooctadiene and Ph 4 C 4 for tetraphenylcyclobutadiene.
Claim 15
Dependent Claim
13 words
A process according to claim 10, wherein the dopant is a palladium complex.
Claim 16
Dependent Claim
25 words
A process according to claim 13, wherein the palladium complex is (PhCN) 2 PdCl 2 or [(C 2 H 4 )PdCl 2 ] 2 .
Claim 17
Dependent Claim
116 words
A process according to claim 1, wherein the dopant is a combination of a cation selected from the group consisting of triphenylmethyl ion [(C 6 H 5 ) 3 C + ], tropylium ion (C 7 H 7 + ), acyl ion (RCO + ), dialkoxycarbonium ion [RC(OR') 2 + ], and triethyloxonium ion [(C 2 H 5 ) 3 O + ] with an anion selected from the group consisting of BF 4 - , AlCl 4 - , FeCl 4 - , SnCl 5 - , PF 6 - , SbClhd 6 - , SbF 6 - , ClO 4 - , CF 3 SO 3 - and CF 3 CO 2 - .
Claim 18
Dependent Claim
25 words
A process according to claim 1, wherein the dopant is a parabenzoquinone derivative selected from the group consisting of 2,3-dicyano-5-chloroparabenzoquinone, 2,3-dichloro-5,6-dicyanoparabenzoquinone, 2,3-dicyano-5-phenylsulfonylparabenzoquinone, 2,3-dicyano-5-chloro-6-phenylsulfonylparabenzoquinone and 2,3,5,6-tetracyanoparabenzoquinone.
Claim 19
Dependent Claim
44 words
A process according to claim 1, wherein the parabenzoquinone derivative has a first half wave reduction potential (-E1/2) of less than -0.2 V as measured at 25° C. by means of a saturated calomel electrode using LiClO 4 as a supporting electrolyte in acetonitrile.
Claim 20
Dependent Claim
42 words
A process according to claim 1, wherein the organic solvent is selected from the group consisting of aromatic hydrocarbons, nitrile compounds, nitro compounds, ether compounds, lower alcohols, halogeno compounds, ester compounds, ketone compounds, sulfoxide compounds and lower organic acids and their anhydrides.
Claim 21
Dependent Claim
55 words
A process according to claim 10, wherein the organic solvent is a compound selected from the group consisting of benzene, toluene, xylene, nitromethane, nitroethane, nitrobenzene, acetonitrile, benzonitrile, diethyl ether, tetrahydrofuran, dioxane, anisole, methanol, ethanol, propanol, dichloromethane, chloroform, chlorobenzene, methylene chloride, trifluoroacetic acid, methyl acetate, ethyl acetate, acetone, acetophenone, dimethylsulfoxide, N,N-dimethylformamide, acetic acid and acetic anhydride.
Claim 22
Dependent Claim
28 words
A doped acetylene polymer according to claim 1, wherein the dopant is selected from the group consisting of a carbonium salt, an oxonium salt and a parabenzoquinone derivative.
Claim 23
Dependent Claim
26 words
A process according to claim 10, wherein the dopant is selected from the group consisting of a carbonium salt, an oxonium salt and a parabenzoquinone derivative.
References Cited (Backward Citations)
US3622367A
Cited
US3684534A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-13 | 1986-03-15 | 1986-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-13 | 1990-03-15 | 1990-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-13 | 1994-03-15 | 1994-09-14 | $7700.00 | Window Closed / Lapsed |