DE2329492C3 - Organisches Halbleitermaterial - Google Patents
Organisches HalbleitermaterialInfo
- Publication number
- DE2329492C3 DE2329492C3 DE2329492A DE2329492A DE2329492C3 DE 2329492 C3 DE2329492 C3 DE 2329492C3 DE 2329492 A DE2329492 A DE 2329492A DE 2329492 A DE2329492 A DE 2329492A DE 2329492 C3 DE2329492 C3 DE 2329492C3
- Authority
- DE
- Germany
- Prior art keywords
- tcnc
- complex
- salt
- salts
- semiconductor material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000463 material Substances 0.000 title claims description 5
- 239000004065 semiconductor Substances 0.000 title claims description 4
- 239000013078 crystal Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- UWYFNFLURVSHSN-UHFFFAOYSA-N 1-tert-butylquinolin-1-ium Chemical compound C1=CC=C2[N+](C(C)(C)C)=CC=CC2=C1 UWYFNFLURVSHSN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 heterocyclic nitrogen compound Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- HSNJJEPLDNIQTM-UHFFFAOYSA-N 1-propan-2-yl-2h-quinoline Chemical compound C1=CC=C2N(C(C)C)CC=CC2=C1 HSNJJEPLDNIQTM-UHFFFAOYSA-N 0.000 description 1
- CUUHOLKEFUEQJE-UHFFFAOYSA-N 1-propan-2-ylquinolin-1-ium Chemical compound C1=CC=C2[N+](C(C)C)=CC=CC2=C1 CUUHOLKEFUEQJE-UHFFFAOYSA-N 0.000 description 1
- GMZLALYCWQSOQS-UHFFFAOYSA-N 2-butylquinoline Chemical compound C1=CC=CC2=NC(CCCC)=CC=C21 GMZLALYCWQSOQS-UHFFFAOYSA-N 0.000 description 1
- OSPRJZOKXPAEOT-UHFFFAOYSA-N 2-ethylpyridine;2-propylpyridine Chemical compound CCC1=CC=CC=N1.CCCC1=CC=CC=N1 OSPRJZOKXPAEOT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001663 electronic absorption spectrum Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/10—Quaternary compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01C—RESISTORS
- H01C7/00—Non-adjustable resistors formed as one or more layers or coatings; Non-adjustable resistors made from powdered conducting material or powdered semi-conducting material with or without insulating material
- H01C7/04—Non-adjustable resistors formed as one or more layers or coatings; Non-adjustable resistors made from powdered conducting material or powdered semi-conducting material with or without insulating material having negative temperature coefficient
- H01C7/049—Non-adjustable resistors formed as one or more layers or coatings; Non-adjustable resistors made from powdered conducting material or powdered semi-conducting material with or without insulating material having negative temperature coefficient mainly consisting of organic or organo-metal substances
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5750372A JPS5551283B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-08 | 1972-06-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2329492A1 DE2329492A1 (de) | 1974-01-03 |
| DE2329492B2 DE2329492B2 (de) | 1978-07-13 |
| DE2329492C3 true DE2329492C3 (de) | 1979-03-15 |
Family
ID=13057515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2329492A Expired DE2329492C3 (de) | 1972-06-08 | 1973-06-08 | Organisches Halbleitermaterial |
Country Status (7)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2755733A (en) * | 1952-03-14 | 1956-07-24 | Arosio Felice | Coffee making machine |
| US4206308A (en) * | 1976-06-11 | 1980-06-03 | Matsushita Electric Industrial Co., Ltd. | Organic heat-sensitive semiconductive materials |
| US4183006A (en) * | 1976-06-11 | 1980-01-08 | Matsushita Electric Industrial Company, Limited | Organic heat-sensitive semiconductive materials |
| US4157332A (en) * | 1976-06-11 | 1979-06-05 | Matsushita Electric Industrial Co., Ltd. | Heat-sensitive thiazolium-7,7,8,8-tetracyanoquinodimethane semiconductive materials |
| DE3335589A1 (de) * | 1983-09-30 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von tcnq-komplexen |
| DE3509070A1 (de) * | 1985-03-14 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Schmelzbare, elektrisch leitfaehige tcnq-komplexe |
| DE3628905A1 (de) * | 1986-08-26 | 1988-03-03 | Bayer Ag | Schmelzbare, elektrisch leitfaehige tcnq-komplexe, verfahren zu ihrer herstellung und ihre verwendung |
| JPS63126212A (ja) * | 1986-11-14 | 1988-05-30 | 松下電器産業株式会社 | 固体電解コンデンサ |
| DE3922852A1 (de) * | 1989-07-12 | 1991-01-24 | Roederstein Kondensatoren | Feststoffelektrolyte und diese enthaltende kondensatoren |
| EP1331482A1 (de) * | 2002-01-25 | 2003-07-30 | BMS Sensor Technology SA | Konjugat zur Bestimmung von Antigenen mittels Biosensoren |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833809A (en) * | 1955-10-21 | 1958-05-06 | Du Pont | Acyclic, polynitrile-containing, unsaturated compounds and preparation thereof |
| US2766135A (en) * | 1955-10-21 | 1956-10-09 | Du Pont | Method of preparing tricyanovinyl alcohol and heavy metal salts thereof, heavy metalsalts and hydrates of the alcohol and method of using the heavy metal salt as a heat recording coating composition |
| US2809972A (en) * | 1956-04-26 | 1957-10-15 | Du Pont | 1, 1, 2, 2,-tetracyanoethanesulfonic acid and salts thereof |
| US3115506A (en) * | 1960-03-28 | 1963-12-24 | Du Pont | Derivatives of 1, 4-bismethylene cyclohexane and 1, 4-bismethylene cyclohexadiene and processes of preparation |
| US3162641A (en) * | 1962-07-23 | 1964-12-22 | Du Pont | Charge-transfer compounds of 7, 7, 8, 8-tetracyano-p-quinodimethan and chydrocarbylsubstituted 7, 7, 8, 8-tetracyano-p-quinodimethans with lewis bases |
| US3334109A (en) * | 1964-08-07 | 1967-08-01 | Monsanto Res Corp | Charge transfer complexes |
| US3681353A (en) * | 1965-12-16 | 1972-08-01 | Du Pont | Charge-transfer complexes of fluoro-and cyano-substituted tetracyanquinodimethans |
-
1972
- 1972-06-08 JP JP5750372A patent/JPS5551283B2/ja not_active Expired
-
1973
- 1973-06-07 IT IT50517/73A patent/IT986124B/it active
- 1973-06-07 US US05/367,720 patent/US3941792A/en not_active Expired - Lifetime
- 1973-06-07 CA CA173,454A patent/CA1006874A/en not_active Expired
- 1973-06-07 FR FR7320809A patent/FR2187784B1/fr not_active Expired
- 1973-06-08 GB GB2743973A patent/GB1376556A/en not_active Expired
- 1973-06-08 DE DE2329492A patent/DE2329492C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5551283B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-12-23 |
| DE2329492A1 (de) | 1974-01-03 |
| FR2187784B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-29 |
| JPS4915995A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-12 |
| FR2187784A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-01-18 |
| US3941792A (en) | 1976-03-02 |
| GB1376556A (en) | 1974-12-04 |
| DE2329492B2 (de) | 1978-07-13 |
| CA1006874A (en) | 1977-03-15 |
| IT986124B (it) | 1975-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |