WO2005055248A2 - Organic semiconducting layer formulations comprising polyacenes and organic binder polymers - Google Patents
Organic semiconducting layer formulations comprising polyacenes and organic binder polymers Download PDFInfo
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- WO2005055248A2 WO2005055248A2 PCT/GB2004/004973 GB2004004973W WO2005055248A2 WO 2005055248 A2 WO2005055248 A2 WO 2005055248A2 GB 2004004973 W GB2004004973 W GB 2004004973W WO 2005055248 A2 WO2005055248 A2 WO 2005055248A2
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- semiconducting layer
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- ZIPLKLQPLOWLTM-UHFFFAOYSA-N naphthalene-2,3-dicarbaldehyde Chemical compound C1=CC=C2C=C(C=O)C(C=O)=CC2=C1 ZIPLKLQPLOWLTM-UHFFFAOYSA-N 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- IGKLGCQYPZTEPK-UHFFFAOYSA-N pentacene-1,2-dione Chemical compound C1=CC=C2C=C(C=C3C(C=C4C=CC(C(C4=C3)=O)=O)=C3)C3=CC2=C1 IGKLGCQYPZTEPK-UHFFFAOYSA-N 0.000 description 1
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- 229920000307 polymer substrate Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 229920005604 random copolymer Polymers 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- WSEJZRIZDQWMKQ-UHFFFAOYSA-N thiophene-2,3-dicarbaldehyde Chemical compound O=CC=1C=CSC=1C=O WSEJZRIZDQWMKQ-UHFFFAOYSA-N 0.000 description 1
- YPWVHVMZAIEIPO-UHFFFAOYSA-N tri(propan-2-yl)-[2-[14-[2-tri(propan-2-yl)silylethynyl]pentacen-5-yl]ethynyl]silane Chemical compound C1=CC=C2C=C(C=C3C(C#C[Si](C(C)C)(C(C)C)C(C)C)=C4C(C=CC=C4)=C(C#C[Si](C(C)C)(C(C)C)C(C)C)C3=C3)C3=CC2=C1 YPWVHVMZAIEIPO-UHFFFAOYSA-N 0.000 description 1
- KIQLSDMNLNXOJK-UHFFFAOYSA-N triethoxy-[2-[13-(2-triethoxysilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC=C2C=C3C(C#C[Si](OCC)(OCC)OCC)=C(C=C4C(C=CC=C4)=C4)C4=C(C#C[Si](OCC)(OCC)OCC)C3=CC2=C1 KIQLSDMNLNXOJK-UHFFFAOYSA-N 0.000 description 1
- IULVRHOZBBTGEH-UHFFFAOYSA-N triethoxy-[2-[14-(2-triethoxysilylethynyl)pentacen-5-yl]ethynyl]silane Chemical compound C1=CC=C2C=C(C=C3C(C#C[Si](OCC)(OCC)OCC)=C4C(C=CC=C4)=C(C#C[Si](OCC)(OCC)OCC)C3=C3)C3=CC2=C1 IULVRHOZBBTGEH-UHFFFAOYSA-N 0.000 description 1
- FWSPXZXVNVQHIF-UHFFFAOYSA-N triethyl(ethynyl)silane Chemical group CC[Si](CC)(CC)C#C FWSPXZXVNVQHIF-UHFFFAOYSA-N 0.000 description 1
- WSBQAUOFFOKRMX-UHFFFAOYSA-N triethyl-[2-[13-(2-triethylsilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC=C2C=C3C(C#C[Si](CC)(CC)CC)=C(C=C4C(C=CC=C4)=C4)C4=C(C#C[Si](CC)(CC)CC)C3=CC2=C1 WSBQAUOFFOKRMX-UHFFFAOYSA-N 0.000 description 1
- MREZNCHLZZZEKL-UHFFFAOYSA-N trimethoxy-[2-[13-(2-trimethoxysilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC=C2C=C3C(C#C[Si](OC)(OC)OC)=C(C=C4C(C=CC=C4)=C4)C4=C(C#C[Si](OC)(OC)OC)C3=CC2=C1 MREZNCHLZZZEKL-UHFFFAOYSA-N 0.000 description 1
- ZZARUHXYSWUTAX-UHFFFAOYSA-N trimethoxy-[2-[14-(2-trimethoxysilylethynyl)pentacen-5-yl]ethynyl]silane Chemical compound C1=CC=C2C=C(C=C3C(C#C[Si](OC)(OC)OC)=C4C(C=CC=C4)=C(C#C[Si](OC)(OC)OC)C3=C3)C3=CC2=C1 ZZARUHXYSWUTAX-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- MYKQRRZJBVVBMU-UHFFFAOYSA-N trimethyl-[2-[13-(2-trimethylsilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC=C2C=C3C(C#C[Si](C)(C)C)=C(C=C4C(C=CC=C4)=C4)C4=C(C#C[Si](C)(C)C)C3=CC2=C1 MYKQRRZJBVVBMU-UHFFFAOYSA-N 0.000 description 1
- BGEOYXSPZHDONX-UHFFFAOYSA-N trimethyl-[2-[14-(2-trimethylsilylethynyl)pentacen-5-yl]ethynyl]silane Chemical compound C1=CC=C2C=C(C=C3C(C#C[Si](C)(C)C)=C4C(C=CC=C4)=C(C#C[Si](C)(C)C)C3=C3)C3=CC2=C1 BGEOYXSPZHDONX-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- JMGDZABHYJJVDH-UHFFFAOYSA-N tripropyl-[2-[13-(2-tripropylsilylethynyl)pentacen-6-yl]ethynyl]silane Chemical compound C1=CC=C2C=C3C(C#C[Si](CCC)(CCC)CCC)=C(C=C4C(C=CC=C4)=C4)C4=C(C#C[Si](CCC)(CCC)CCC)C3=CC2=C1 JMGDZABHYJJVDH-UHFFFAOYSA-N 0.000 description 1
- LBHLPJVCBIJJCI-UHFFFAOYSA-N tripropyl-[2-[14-(2-tripropylsilylethynyl)pentacen-5-yl]ethynyl]silane Chemical compound C1=CC=C2C=C(C=C3C(C#C[Si](CCC)(CCC)CCC)=C4C(C=CC=C4)=C(C#C[Si](CCC)(CCC)CCC)C3=C3)C3=CC2=C1 LBHLPJVCBIJJCI-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/06—Copolymers with vinyl aromatic monomers
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- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
- H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K85/115—Polyfluorene; Derivatives thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Thin Film Transistor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photovoltaic Devices (AREA)
- Light Receiving Elements (AREA)
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Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006540612A JP5089986B2 (ja) | 2003-11-28 | 2004-11-25 | 有機半導体層およびその改善 |
| AT04819715T ATE475971T1 (de) | 2003-11-28 | 2004-11-25 | Organische halbleiterschicht-formulierungen mit polyacenen und organischen binderpolymeren |
| DE602004028399T DE602004028399D1 (de) | 2003-11-28 | 2004-11-25 | Organische halbleiterschicht-formulierungen mit polyacenen und organischen binderpolymeren |
| EP04819715A EP1687830B1 (en) | 2003-11-28 | 2004-11-25 | Organic semiconducting layer formulations comprising polyacenes and organic binder polymers |
| US10/580,552 US7842942B2 (en) | 2003-11-28 | 2004-11-25 | Organic semiconducting layers |
| KR1020067010374A KR101217963B1 (ko) | 2003-11-28 | 2006-05-26 | 유기 반도체 층의 개선 및 이와 관련된 개선 |
| US11/671,877 US7807993B2 (en) | 2003-11-28 | 2007-02-06 | Organic pentacene semiconducting layers |
| US11/822,594 US7576208B2 (en) | 2003-11-28 | 2007-07-09 | Organic semiconductor layers |
| US12/719,545 US8119804B2 (en) | 2003-11-28 | 2010-03-08 | Organic semiconducting layers |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0327654A GB0327654D0 (en) | 2003-11-28 | 2003-11-28 | Improvements in and relating to organic semiconducting layers |
| GB0327654.0 | 2003-11-28 | ||
| GB0407852.3 | 2004-04-07 | ||
| GB0407852A GB0407852D0 (en) | 2004-04-07 | 2004-04-07 | Improvements in and relating to organic semi-conducting layers |
| GB0414347A GB0414347D0 (en) | 2004-06-26 | 2004-06-26 | Improvements in and relating to organic semiconducting layers |
| GB0414347.5 | 2004-06-26 |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/580,552 A-371-Of-International US7842942B2 (en) | 2003-11-28 | 2004-11-25 | Organic semiconducting layers |
| US11/671,877 Division US7807993B2 (en) | 2003-11-28 | 2007-02-06 | Organic pentacene semiconducting layers |
| US11/822,594 Division US7576208B2 (en) | 2003-11-28 | 2007-07-09 | Organic semiconductor layers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2005055248A2 true WO2005055248A2 (en) | 2005-06-16 |
| WO2005055248A3 WO2005055248A3 (en) | 2005-07-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB2004/004973 WO2005055248A2 (en) | 2003-11-28 | 2004-11-25 | Organic semiconducting layer formulations comprising polyacenes and organic binder polymers |
Country Status (8)
Cited By (175)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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Also Published As
| Publication number | Publication date |
|---|---|
| US20070102696A1 (en) | 2007-05-10 |
| DE602004028399D1 (de) | 2010-09-09 |
| EP1783781A3 (en) | 2007-10-03 |
| JP5089986B2 (ja) | 2012-12-05 |
| JP2007519227A (ja) | 2007-07-12 |
| KR101217963B1 (ko) | 2013-01-02 |
| JP2012246295A (ja) | 2012-12-13 |
| KR20060110309A (ko) | 2006-10-24 |
| US7807993B2 (en) | 2010-10-05 |
| TWI358144B (en) | 2012-02-11 |
| US7576208B2 (en) | 2009-08-18 |
| JP5667128B2 (ja) | 2015-02-12 |
| US8119804B2 (en) | 2012-02-21 |
| TW200529483A (en) | 2005-09-01 |
| US7842942B2 (en) | 2010-11-30 |
| EP1687830A2 (en) | 2006-08-09 |
| WO2005055248A3 (en) | 2005-07-28 |
| EP1808866A1 (en) | 2007-07-18 |
| US20080009625A1 (en) | 2008-01-10 |
| US20100227956A1 (en) | 2010-09-09 |
| EP1687830B1 (en) | 2010-07-28 |
| ATE475971T1 (de) | 2010-08-15 |
| EP1783781A2 (en) | 2007-05-09 |
| US20070137520A1 (en) | 2007-06-21 |
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