KR20060076277A - 아센-티오펜 반도체 - Google Patents
아센-티오펜 반도체 Download PDFInfo
- Publication number
- KR20060076277A KR20060076277A KR1020067003058A KR20067003058A KR20060076277A KR 20060076277 A KR20060076277 A KR 20060076277A KR 1020067003058 A KR1020067003058 A KR 1020067003058A KR 20067003058 A KR20067003058 A KR 20067003058A KR 20060076277 A KR20060076277 A KR 20060076277A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- acene
- thiophene
- groups
- layer
- 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.)
- Ceased
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000010409 thin film Substances 0.000 claims abstract description 26
- 239000010410 layer Substances 0.000 claims description 86
- 229920000642 polymer Polymers 0.000 claims description 75
- -1 2-anthracenyl Chemical group 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 36
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000002335 surface treatment layer Substances 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 26
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000000151 deposition Methods 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000013545 self-assembled monolayer Substances 0.000 claims description 12
- 239000002094 self assembled monolayer Substances 0.000 claims description 11
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- 125000005309 thioalkoxy group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 5
- 239000007772 electrode material Substances 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 abstract description 17
- 239000002800 charge carrier Substances 0.000 abstract description 10
- 239000000463 material Substances 0.000 description 65
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- 239000002243 precursor Substances 0.000 description 24
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- 125000001931 aliphatic group Chemical group 0.000 description 20
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- 230000015572 biosynthetic process Effects 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 238000000113 differential scanning calorimetry Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000859 sublimation Methods 0.000 description 14
- 230000008022 sublimation Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
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- 125000000524 functional group Chemical group 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- 125000005842 heteroatom Chemical group 0.000 description 8
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- 125000004122 cyclic group Chemical group 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- CPEOCXYBTJPYIA-UHFFFAOYSA-N 2-chlorotetracene Chemical compound C1=CC=CC2=CC3=CC4=CC(Cl)=CC=C4C=C3C=C21 CPEOCXYBTJPYIA-UHFFFAOYSA-N 0.000 description 5
- ISKXWVTWFWNJCL-UHFFFAOYSA-N 3,7,11,15-tetramethylhexadecylphosphonic acid Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CCP(O)(O)=O ISKXWVTWFWNJCL-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 229920006395 saturated elastomer Polymers 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- BPRGLVVFWRNXEP-UHFFFAOYSA-N 2,6-dibromoanthracene Chemical compound C1=C(Br)C=CC2=CC3=CC(Br)=CC=C3C=C21 BPRGLVVFWRNXEP-UHFFFAOYSA-N 0.000 description 4
- PYXBCVWIECUMDW-UHFFFAOYSA-N 2-bromoanthracene Chemical compound C1=CC=CC2=CC3=CC(Br)=CC=C3C=C21 PYXBCVWIECUMDW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
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- 230000008901 benefit Effects 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
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- 150000003577 thiophenes Chemical class 0.000 description 4
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 3
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 3
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 125000004054 acenaphthylenyl group Chemical class C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Chemical class C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
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- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000005577 anthracene group Chemical group 0.000 description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- B32B37/153—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the properties of the layers with at least one layer being manufactured and immediately laminated before reaching its stable state, e.g. in which a layer is extruded and laminated while in semi-molten state at least one layer is extruded and immediately laminated while in semi-molten state
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
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- Health & Medical Sciences (AREA)
- Theoretical Computer Science (AREA)
- Medicinal Chemistry (AREA)
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- Mathematical Physics (AREA)
- Thin Film Transistor (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/641,730 US6998068B2 (en) | 2003-08-15 | 2003-08-15 | Acene-thiophene semiconductors |
| US10/641,730 | 2003-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060076277A true KR20060076277A (ko) | 2006-07-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067003058A Ceased KR20060076277A (ko) | 2003-08-15 | 2004-06-25 | 아센-티오펜 반도체 |
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| Country | Link |
|---|---|
| US (3) | US6998068B2 (https=) |
| EP (1) | EP1654248A1 (https=) |
| JP (1) | JP4733033B2 (https=) |
| KR (1) | KR20060076277A (https=) |
| CN (1) | CN1835941B (https=) |
| WO (1) | WO2005019198A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100901856B1 (ko) * | 2008-06-25 | 2009-06-09 | 경상대학교산학협력단 | 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20030097010A1 (en) * | 2001-09-27 | 2003-05-22 | Vogel Dennis E. | Process for preparing pentacene derivatives |
| DE10321851A1 (de) * | 2003-05-15 | 2004-12-02 | Creavis Gesellschaft Für Technologie Und Innovation Mbh | Verwendung von mit Fluorsilanen hydrophobierten Partikeln zur Herstellung von selbstreinigenden Oberflächen mit lipophoben, oleophoben, laktophoben und hydrophoben Eigenschaften |
| US20110139386A1 (en) * | 2003-06-19 | 2011-06-16 | Eastman Chemical Company | Wet lap composition and related processes |
| US8513147B2 (en) | 2003-06-19 | 2013-08-20 | Eastman Chemical Company | Nonwovens produced from multicomponent fibers |
| US20040260034A1 (en) * | 2003-06-19 | 2004-12-23 | Haile William Alston | Water-dispersible fibers and fibrous articles |
| US7892993B2 (en) | 2003-06-19 | 2011-02-22 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US7078937B2 (en) | 2003-12-17 | 2006-07-18 | 3M Innovative Properties Company | Logic circuitry powered by partially rectified ac waveform |
| US20060074166A1 (en) * | 2003-12-19 | 2006-04-06 | Tpl, Inc. Title And Interest In An Application | Moldable high dielectric constant nano-composites |
| US20080128961A1 (en) * | 2003-12-19 | 2008-06-05 | Tpl, Inc. | Moldable high dielectric constant nano-composites |
| US20060074164A1 (en) * | 2003-12-19 | 2006-04-06 | Tpl, Inc. | Structured composite dielectrics |
| JP2006005036A (ja) * | 2004-06-16 | 2006-01-05 | Sony Corp | 有機化合物結晶及び電界効果型トランジスタ |
| JP2006028055A (ja) * | 2004-06-17 | 2006-02-02 | Konica Minolta Holdings Inc | 有機半導体材料、有機トランジスタ、電界効果トランジスタ及びスイッチング素子 |
| JP2006028054A (ja) * | 2004-07-14 | 2006-02-02 | Konica Minolta Holdings Inc | 有機薄膜トランジスタ材料、有機薄膜トランジスタ、電界効果トランジスタ及びスイッチング素子 |
| WO2007050049A1 (en) * | 2004-09-14 | 2007-05-03 | Northwestern University | Carbonyl-functionalized thiophene compounds and related device structures |
| US7399668B2 (en) * | 2004-09-30 | 2008-07-15 | 3M Innovative Properties Company | Method for making electronic devices having a dielectric layer surface treatment |
| JP5992133B2 (ja) * | 2004-10-01 | 2016-09-14 | メルク パテント ゲーエムベーハー | 有機半導体を含む電子デバイス |
| WO2006050496A1 (en) | 2004-11-02 | 2006-05-11 | E.I. Dupont De Nemours And Company | Substituted anthracenes and electronic devices containing the substituted anthracenes |
| US7315042B2 (en) * | 2004-11-18 | 2008-01-01 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compounds |
| US20060128165A1 (en) * | 2004-12-13 | 2006-06-15 | 3M Innovative Properties Company | Method for patterning surface modification |
| JPWO2006064776A1 (ja) * | 2004-12-17 | 2008-06-12 | コニカミノルタホールディングス株式会社 | 有機薄膜トランジスタの製造方法 |
| EP1684365A3 (en) * | 2005-01-20 | 2008-08-13 | Fuji Electric Holdings Co., Ltd. | Transistor |
| US7985353B2 (en) * | 2005-05-21 | 2011-07-26 | Merck Patent Gmbh | Oligomeric is polyacene and semiconductor formulations |
| DE102005029574A1 (de) | 2005-06-25 | 2006-12-28 | Technische Universität Darmstadt | Oligo-Tetracene, ihre Herstellung und ihre Anwendung |
| US8414962B2 (en) | 2005-10-28 | 2013-04-09 | The Penn State Research Foundation | Microcontact printed thin film capacitors |
| CN100443483C (zh) * | 2005-12-08 | 2008-12-17 | 中国科学院长春应用化学研究所 | 稠环单元封端的齐聚噻吩类高迁移率有机半导体材料及用途 |
| US7524373B2 (en) * | 2006-01-30 | 2009-04-28 | University Of Iowa Research Foundation | Apparatus and semiconductor co-crystal |
| US7635745B2 (en) * | 2006-01-31 | 2009-12-22 | Eastman Chemical Company | Sulfopolyester recovery |
| US8138075B1 (en) | 2006-02-06 | 2012-03-20 | Eberlein Dietmar C | Systems and methods for the manufacture of flat panel devices |
| US7667230B2 (en) * | 2006-03-31 | 2010-02-23 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers |
| US7608679B2 (en) * | 2006-03-31 | 2009-10-27 | 3M Innovative Properties Company | Acene-thiophene copolymers |
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| US20070247317A1 (en) * | 2006-04-21 | 2007-10-25 | Rick Farrell | Apparatus and method for fine art authentication |
| US7495251B2 (en) * | 2006-04-21 | 2009-02-24 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
| US7666968B2 (en) * | 2006-04-21 | 2010-02-23 | 3M Innovative Properties Company | Acene-thiophene copolymers with silethynly groups |
| KR100790761B1 (ko) * | 2006-09-29 | 2008-01-03 | 한국전자통신연구원 | 인버터 |
| KR100816498B1 (ko) * | 2006-12-07 | 2008-03-24 | 한국전자통신연구원 | 표면 처리된 층을 포함하는 유기 인버터 및 그 제조 방법 |
| JP5200377B2 (ja) * | 2006-12-28 | 2013-06-05 | 大日本印刷株式会社 | 有機半導体素子 |
| WO2008097300A2 (en) * | 2007-02-08 | 2008-08-14 | Regents Of The University Of Minnesota | Ion gels and electronic devices utilizing ion gels |
| US20090114618A1 (en) * | 2007-06-21 | 2009-05-07 | 3M Innovative Properties Company | Method of making hierarchical articles |
| US20090041986A1 (en) * | 2007-06-21 | 2009-02-12 | 3M Innovative Properties Company | Method of making hierarchical articles |
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- 2004-06-25 CN CN2004800234102A patent/CN1835941B/zh not_active Expired - Fee Related
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- 2004-06-25 EP EP04756064A patent/EP1654248A1/en not_active Withdrawn
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- 2005-10-20 US US11/256,281 patent/US7276395B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100901856B1 (ko) * | 2008-06-25 | 2009-06-09 | 경상대학교산학협력단 | 전자주게 치환기를 갖는 나프탈렌으로 말단 기능화된새로운 올리고머 반도체 화합물과 이를 이용한유기박막트랜지스터 |
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| US20050035333A1 (en) | 2005-02-17 |
| US20060049386A1 (en) | 2006-03-09 |
| WO2005019198A1 (en) | 2005-03-03 |
| EP1654248A1 (en) | 2006-05-10 |
| US7276395B2 (en) | 2007-10-02 |
| CN1835941B (zh) | 2012-03-28 |
| US6998068B2 (en) | 2006-02-14 |
| JP2007502812A (ja) | 2007-02-15 |
| JP4733033B2 (ja) | 2011-07-27 |
| CN1835941A (zh) | 2006-09-20 |
| US20060033086A1 (en) | 2006-02-16 |
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