JP5193218B2 - 新規の高導電性の有機電荷キャリア輸送材料 - Google Patents
新規の高導電性の有機電荷キャリア輸送材料 Download PDFInfo
- Publication number
- JP5193218B2 JP5193218B2 JP2009536713A JP2009536713A JP5193218B2 JP 5193218 B2 JP5193218 B2 JP 5193218B2 JP 2009536713 A JP2009536713 A JP 2009536713A JP 2009536713 A JP2009536713 A JP 2009536713A JP 5193218 B2 JP5193218 B2 JP 5193218B2
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- JP
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- Prior art keywords
- charge carrier
- organic
- carrier transport
- transport material
- materials
- 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 - Fee Related
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- 239000000463 material Substances 0.000 title claims abstract description 54
- 239000002800 charge carrier Substances 0.000 title claims description 11
- 239000004065 semiconductor Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000005838 radical anions Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000011532 electronic conductor Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SLWIPPZWFZGHEU-UHFFFAOYSA-N 2-[4-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(CC(O)=O)C=C1 SLWIPPZWFZGHEU-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- IONKMFGAXKCLMI-UHFFFAOYSA-N [amino(pyridin-4-yl)methylidene]azanium;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=NC=C1 IONKMFGAXKCLMI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Photovoltaic Devices (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Led Devices (AREA)
- Light Receiving Elements (AREA)
- Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006053644.4 | 2006-11-14 | ||
| DE102006053644A DE102006053644A1 (de) | 2006-11-14 | 2006-11-14 | Neuartiges hochleitfähiges organisches Ladungsträgertransportmaterial |
| PCT/EP2007/062210 WO2008058929A1 (de) | 2006-11-14 | 2007-11-12 | Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010509781A JP2010509781A (ja) | 2010-03-25 |
| JP2010509781A5 JP2010509781A5 (enExample) | 2011-07-21 |
| JP5193218B2 true JP5193218B2 (ja) | 2013-05-08 |
Family
ID=39034834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009536713A Expired - Fee Related JP5193218B2 (ja) | 2006-11-14 | 2007-11-12 | 新規の高導電性の有機電荷キャリア輸送材料 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8309284B2 (enExample) |
| EP (1) | EP2092041B9 (enExample) |
| JP (1) | JP5193218B2 (enExample) |
| KR (1) | KR101482512B1 (enExample) |
| CN (1) | CN101679850B (enExample) |
| AT (1) | ATE481463T1 (enExample) |
| DE (2) | DE102006053644A1 (enExample) |
| WO (1) | WO2008058929A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009047880A1 (de) * | 2009-09-30 | 2011-03-31 | Osram Opto Semiconductors Gmbh | Organische elektronische Vorrichtung und Verfahren zu dessen Herstellung |
| EP2395571B1 (en) | 2010-06-10 | 2013-12-04 | Novaled AG | Organic electronic device comprising an organic semiconducting material |
| DE102012205945A1 (de) | 2012-04-12 | 2013-10-17 | Siemens Aktiengesellschaft | Organische Superdonoren mit mindestens zwei gekoppelten Carben-Gruppen und deren Verwendung als n-Dotierstoffe |
| DE102012217574A1 (de) | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Phosphoroxo-Salze als n-Dotierstoffe für die organische Elektronik |
| DE102012217587A1 (de) | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik |
| DE102015210388A1 (de) | 2015-06-05 | 2016-12-08 | Siemens Aktiengesellschaft | Organische Heterozyklische Alkalimetallsalze als n-Dotierstoffe in der Organischen Elektronik |
| DE102016208298A1 (de) | 2016-05-13 | 2017-11-16 | Siemens Aktiengesellschaft | Organische elektronenleitende Schicht mit n-Dotierstoff |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6025973A (ja) * | 1983-07-20 | 1985-02-08 | Chisso Corp | ピリミジン類 |
| DE4423098A1 (de) * | 1994-07-01 | 1996-01-04 | Hoechst Ag | Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien |
| EP0753780B1 (en) | 1994-12-28 | 2005-03-02 | Seiko Epson Corporation | Polarized lighting apparatus and projection type display device |
| CN1064046C (zh) * | 1997-11-12 | 2001-04-04 | 南开大学戈德防伪技术公司 | 螺环类光致变色化合物及其制备方法 |
| GB0225244D0 (en) * | 2002-10-30 | 2002-12-11 | Ciba Sc Holding Ag | Electroluminescent device |
| KR100573137B1 (ko) * | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
-
2006
- 2006-11-14 DE DE102006053644A patent/DE102006053644A1/de not_active Withdrawn
-
2007
- 2007-11-12 US US12/514,986 patent/US8309284B2/en active Active
- 2007-11-12 KR KR20097012297A patent/KR101482512B1/ko not_active Expired - Fee Related
- 2007-11-12 CN CN2007800422590A patent/CN101679850B/zh active Active
- 2007-11-12 EP EP07822496A patent/EP2092041B9/de active Active
- 2007-11-12 AT AT07822496T patent/ATE481463T1/de active
- 2007-11-12 WO PCT/EP2007/062210 patent/WO2008058929A1/de not_active Ceased
- 2007-11-12 JP JP2009536713A patent/JP5193218B2/ja not_active Expired - Fee Related
- 2007-11-12 DE DE502007005097T patent/DE502007005097D1/de active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ATE481463T1 (de) | 2010-10-15 |
| US8309284B2 (en) | 2012-11-13 |
| EP2092041A1 (de) | 2009-08-26 |
| DE502007005097D1 (de) | 2010-10-28 |
| KR20090106472A (ko) | 2009-10-09 |
| JP2010509781A (ja) | 2010-03-25 |
| CN101679850A (zh) | 2010-03-24 |
| EP2092041B9 (de) | 2011-11-09 |
| CN101679850B (zh) | 2013-05-29 |
| US20100112471A1 (en) | 2010-05-06 |
| KR101482512B1 (ko) | 2015-01-13 |
| WO2008058929A1 (de) | 2008-05-22 |
| EP2092041B1 (de) | 2010-09-15 |
| DE102006053644A1 (de) | 2008-06-12 |
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