CN1698137B - 掺杂的有机半导体材料以及其制备方法 - Google Patents
掺杂的有机半导体材料以及其制备方法 Download PDFInfo
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- CN1698137B CN1698137B CN038009951A CN03800995A CN1698137B CN 1698137 B CN1698137 B CN 1698137B CN 038009951 A CN038009951 A CN 038009951A CN 03800995 A CN03800995 A CN 03800995A CN 1698137 B CN1698137 B CN 1698137B
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- semiconductor material
- organic semiconductor
- doped organic
- oneself
- compound
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 147
- 239000000463 material Substances 0.000 title claims abstract description 145
- 238000004519 manufacturing process Methods 0.000 title description 2
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- 230000000694 effects Effects 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 47
- -1 methoxyl groups Chemical group 0.000 claims description 43
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- 150000003254 radicals Chemical class 0.000 claims description 32
- 239000000975 dye Substances 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 238000005336 cracking Methods 0.000 claims description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
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- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
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- 235000010290 biphenyl Nutrition 0.000 claims description 18
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- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
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- 239000011737 fluorine Substances 0.000 claims description 18
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- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
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- CXZRDVVUVDYSCQ-UHFFFAOYSA-M pyronin B Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3C=C21 CXZRDVVUVDYSCQ-UHFFFAOYSA-M 0.000 claims description 11
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
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- 239000001018 xanthene dye Substances 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 2
- 239000001016 thiazine dye Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 229910052710 silicon Inorganic materials 0.000 claims 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 3
- 239000005864 Sulphur Substances 0.000 claims 3
- 229910052796 boron Inorganic materials 0.000 claims 3
- 150000004985 diamines Chemical class 0.000 claims 3
- 230000005284 excitation Effects 0.000 claims 3
- 229910052745 lead Inorganic materials 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 229910052718 tin Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 claims 1
- KKAJSJJFBSOMGS-UHFFFAOYSA-N 3,6-diamino-10-methylacridinium chloride Chemical compound [Cl-].C1=C(N)C=C2[N+](C)=C(C=C(N)C=C3)C3=CC2=C1 KKAJSJJFBSOMGS-UHFFFAOYSA-N 0.000 claims 1
- LQVYCDPEZPBOMT-UHFFFAOYSA-N 4-[4-(diethylamino)benzenecarboximidoyl]-n,n-diethylaniline;hydrochloride Chemical compound Cl.C1=CC(N(CC)CC)=CC=C1C(=N)C1=CC=C(N(CC)CC)C=C1 LQVYCDPEZPBOMT-UHFFFAOYSA-N 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- XWHUQXFERLNWEQ-UHFFFAOYSA-N Rosamine Natural products CCC1=CC2CN3CCC4(Nc5ccccc5C4=O)C(C2)(C13)C(=O)OC XWHUQXFERLNWEQ-UHFFFAOYSA-N 0.000 claims 1
- 229940023020 acriflavine Drugs 0.000 claims 1
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- KMHJKRGRIJONSV-UHFFFAOYSA-N dioxygen(.1+) Chemical compound [O+]=O KMHJKRGRIJONSV-UHFFFAOYSA-N 0.000 claims 1
- 238000002848 electrochemical method Methods 0.000 claims 1
- KEUKAQNPUBYCIC-UHFFFAOYSA-N ethaneperoxoic acid;hydrogen peroxide Chemical compound OO.CC(=O)OO KEUKAQNPUBYCIC-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims 1
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
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- 239000000376 reactant Substances 0.000 claims 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- KXVADGBQPMPMIQ-UHFFFAOYSA-M tetramethylrosamine chloride Chemical compound [Cl-].C=12C=CC(=[N+](C)C)C=C2OC2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1 KXVADGBQPMPMIQ-UHFFFAOYSA-M 0.000 claims 1
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- 239000002800 charge carrier Substances 0.000 abstract description 11
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- 125000000382 plumbyl group Chemical group [H][Pb]([H])([H])* 0.000 description 1
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- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 1
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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| DE10207859A DE10207859A1 (de) | 2002-02-20 | 2002-02-20 | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
| DE10207859.9 | 2002-02-20 | ||
| PCT/DE2003/000558 WO2003070822A2 (de) | 2002-02-20 | 2003-02-20 | Dotiertes organisches halbleitermaterial sowie verfahren zu dessen herstellung |
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| US5922396A (en) * | 1996-12-23 | 1999-07-13 | The University Of Southern California | Electron transporting and light emitting layers based on organic free radicals |
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| DE10207859A1 (de) | 2003-09-04 |
| US7858967B2 (en) | 2010-12-28 |
| KR100679384B1 (ko) | 2007-02-05 |
| AU2003229476A1 (en) | 2003-09-09 |
| AU2003229476A8 (en) | 2003-09-09 |
| CA2463377C (en) | 2015-01-06 |
| CN1698137A (zh) | 2005-11-16 |
| EP1476881A2 (de) | 2004-11-17 |
| US20050040390A1 (en) | 2005-02-24 |
| CA2463377A1 (en) | 2003-08-28 |
| KR20050004768A (ko) | 2005-01-12 |
| DE10307125B4 (de) | 2017-06-22 |
| DE10307125A1 (de) | 2004-01-08 |
| WO2003070822A2 (de) | 2003-08-28 |
| JP2005525696A (ja) | 2005-08-25 |
| WO2003070822A3 (de) | 2004-06-10 |
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