JP2014527281A5 - - Google Patents
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- Publication number
- JP2014527281A5 JP2014527281A5 JP2014515963A JP2014515963A JP2014527281A5 JP 2014527281 A5 JP2014527281 A5 JP 2014527281A5 JP 2014515963 A JP2014515963 A JP 2014515963A JP 2014515963 A JP2014515963 A JP 2014515963A JP 2014527281 A5 JP2014527281 A5 JP 2014527281A5
- Authority
- JP
- Japan
- Prior art keywords
- organic semiconductor
- compound
- metal sandwich
- semiconductor composition
- integer
- 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.)
- Granted
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- 239000004065 semiconductor Substances 0.000 claims 43
- 239000000203 mixture Substances 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 30
- 229910052751 metal Inorganic materials 0.000 claims 23
- 239000002184 metal Substances 0.000 claims 23
- 238000000034 method Methods 0.000 claims 17
- -1 2-methylquinolyl Chemical group 0.000 claims 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 12
- 150000001768 cations Chemical class 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 6
- 229910052741 iridium Inorganic materials 0.000 claims 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 6
- 229910052742 iron Inorganic materials 0.000 claims 6
- 229910052762 osmium Inorganic materials 0.000 claims 6
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 6
- 229910052703 rhodium Inorganic materials 0.000 claims 6
- 239000010948 rhodium Substances 0.000 claims 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 6
- 229910052707 ruthenium Inorganic materials 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052702 rhenium Inorganic materials 0.000 claims 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052748 manganese Inorganic materials 0.000 claims 4
- 239000011572 manganese Substances 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 125000000058 cyclopentadienyl group Chemical class C1(=CC=CC1)* 0.000 claims 3
- 239000006185 dispersion Substances 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims 2
- 239000006193 liquid solution Substances 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- 150000003624 transition metals Chemical group 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 238000002484 cyclic voltammetry Methods 0.000 claims 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 claims 1
- 239000003792 electrolyte Substances 0.000 claims 1
- 229910003472 fullerene Inorganic materials 0.000 claims 1
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000013086 organic photovoltaic Methods 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims 1
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 239000010409 thin film Substances 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161496667P | 2011-06-14 | 2011-06-14 | |
| US61/496,667 | 2011-06-14 | ||
| PCT/US2012/042287 WO2013055410A1 (en) | 2011-06-14 | 2012-06-13 | N-doping of organic semiconductors by bis-metallosandwich compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014527281A JP2014527281A (ja) | 2014-10-09 |
| JP2014527281A5 true JP2014527281A5 (cg-RX-API-DMAC7.html) | 2015-07-30 |
| JP6129826B2 JP6129826B2 (ja) | 2017-05-17 |
Family
ID=47664399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014515963A Active JP6129826B2 (ja) | 2011-06-14 | 2012-06-13 | ビス−金属サンドイッチ化合物による有機半導体のｎ−ドーピング |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9231219B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2721658A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6129826B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20140053101A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2012321307B2 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2014DN00183A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013055410A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017059337A1 (en) * | 2015-10-02 | 2017-04-06 | Georgetown University | High-resolution in situ electrochemical nmr with interdigitated electrodes |
| WO2020130934A1 (en) * | 2018-12-21 | 2020-06-25 | National University Of Singapore | N-doped electrically conductive organic materials |
| JP7409215B2 (ja) * | 2020-04-28 | 2024-01-09 | 三菱ケミカル株式会社 | 光電変換素子及び発電デバイス |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10347856B8 (de) | 2003-10-10 | 2006-10-19 | Colorado State University Research Foundation, Fort Collins | Halbleiterdotierung |
| JP2007012359A (ja) | 2005-06-29 | 2007-01-18 | Hitachi Displays Ltd | 有機ｅｌ表示装置 |
| JP4928098B2 (ja) | 2005-08-03 | 2012-05-09 | セイコーエプソン株式会社 | 強誘電体キャパシタの製造方法 |
| US7981328B2 (en) * | 2006-06-22 | 2011-07-19 | Georgia Tech Research Corporation | N-type doping of an electron transport material and methods of use thereof |
-
2012
- 2012-06-13 EP EP12821209.9A patent/EP2721658A1/en not_active Withdrawn
- 2012-06-13 AU AU2012321307A patent/AU2012321307B2/en not_active Ceased
- 2012-06-13 WO PCT/US2012/042287 patent/WO2013055410A1/en not_active Ceased
- 2012-06-13 KR KR1020147001032A patent/KR20140053101A/ko not_active Withdrawn
- 2012-06-13 US US14/126,319 patent/US9231219B2/en not_active Expired - Fee Related
- 2012-06-13 IN IN183DEN2014 patent/IN2014DN00183A/en unknown
- 2012-06-13 JP JP2014515963A patent/JP6129826B2/ja active Active
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