JP2011508967A - アントラセンを主成分とする溶液加工性有機半導体 - Google Patents
アントラセンを主成分とする溶液加工性有機半導体 Download PDFInfo
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- JP2011508967A JP2011508967A JP2010539572A JP2010539572A JP2011508967A JP 2011508967 A JP2011508967 A JP 2011508967A JP 2010539572 A JP2010539572 A JP 2010539572A JP 2010539572 A JP2010539572 A JP 2010539572A JP 2011508967 A JP2011508967 A JP 2011508967A
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- semiconductor
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- insulating polymer
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 189
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title abstract description 10
- 239000008199 coating composition Substances 0.000 claims abstract description 70
- 229920000642 polymer Polymers 0.000 claims abstract description 62
- 150000003384 small molecules Chemical class 0.000 claims abstract description 51
- 239000003960 organic solvent Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 29
- -1 anthracene compound Chemical class 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 239000010409 thin film Substances 0.000 claims description 36
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
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- 125000000304 alkynyl group Chemical group 0.000 claims description 12
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- 125000004001 thioalkyl group Chemical group 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
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- 125000005842 heteroatom Chemical group 0.000 claims description 8
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
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- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
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- 229920001218 Pullulan Polymers 0.000 claims description 4
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 4
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- 238000000576 coating method Methods 0.000 claims description 4
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- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
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- 239000010408 film Substances 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 21
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 238000004440 column chromatography Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 11
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000002207 thermal evaporation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000007605 air drying Methods 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000002335 surface treatment layer Substances 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000012043 crude product Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
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- 238000000859 sublimation Methods 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- JUFYHUWBLXKCJM-UHFFFAOYSA-N 2,6-dibromoanthracene-9,10-dione Chemical compound BrC1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 JUFYHUWBLXKCJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
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- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 4
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- ZLWDQLLYCNFCNH-UHFFFAOYSA-N 2-[2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10-[2-tri(propan-2-yl)silylethynyl]anthracen-9-yl]ethynyl-tri(propan-2-yl)silane Chemical compound C1=C2C(C#C[Si](C(C)C)(C(C)C)C(C)C)=C3C=CC(B4OC(C)(C)C(C)(C)O4)=CC3=C(C#C[Si](C(C)C)(C(C)C)C(C)C)C2=CC=C1B1OC(C)(C)C(C)(C)O1 ZLWDQLLYCNFCNH-UHFFFAOYSA-N 0.000 description 3
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
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- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002094 self assembled monolayer Substances 0.000 description 1
- 239000013545 self-assembled monolayer Substances 0.000 description 1
- 238000005389 semiconductor device fabrication Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- RTYNRTUKJVYEIE-UHFFFAOYSA-N tert-butyl-ethynyl-dimethylsilane Chemical group CC(C)(C)[Si](C)(C)C#C RTYNRTUKJVYEIE-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Thin Film Transistor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1410107P | 2007-12-17 | 2007-12-17 | |
| PCT/US2008/084122 WO2009079150A1 (en) | 2007-12-17 | 2008-11-20 | Solution processable organic semiconductors based on anthracene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011508967A true JP2011508967A (ja) | 2011-03-17 |
| JP2011508967A5 JP2011508967A5 (enExample) | 2012-01-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010539572A Pending JP2011508967A (ja) | 2007-12-17 | 2008-11-20 | アントラセンを主成分とする溶液加工性有機半導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8178873B2 (enExample) |
| EP (1) | EP2232606A1 (enExample) |
| JP (1) | JP2011508967A (enExample) |
| CN (1) | CN101926017B (enExample) |
| WO (1) | WO2009079150A1 (enExample) |
Cited By (6)
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|---|---|---|---|---|
| JP2013004965A (ja) * | 2011-06-13 | 2013-01-07 | Xerox Corp | 電子デバイス |
| WO2014189116A1 (ja) * | 2013-05-23 | 2014-11-27 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
| WO2014189114A1 (ja) * | 2013-05-23 | 2014-11-27 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
| WO2015076171A1 (ja) * | 2013-11-21 | 2015-05-28 | 株式会社ダイセル | 有機トランジスタ製造用溶剤 |
| WO2015133375A1 (ja) * | 2014-03-03 | 2015-09-11 | 富士フイルム株式会社 | 有機薄膜トランジスタ及びその製造方法 |
| JP2016178274A (ja) * | 2015-03-19 | 2016-10-06 | 三菱化学株式会社 | 半導体デバイス、太陽電池、太陽電池モジュール、及び組成物 |
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|---|---|---|---|---|
| JP2011508967A (ja) | 2007-12-17 | 2011-03-17 | スリーエム イノベイティブ プロパティズ カンパニー | アントラセンを主成分とする溶液加工性有機半導体 |
| JP5658145B2 (ja) * | 2008-05-30 | 2015-01-21 | スリーエム イノベイティブ プロパティズ カンパニー | シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 |
| EP2318420A1 (en) * | 2008-06-19 | 2011-05-11 | 3M Innovative Properties Company | Solution processable organic semiconductors |
| US8154080B2 (en) * | 2008-12-05 | 2012-04-10 | Xerox Corporation | Dielectric structure having lower-k and higher-k materials |
| WO2010138807A1 (en) | 2009-05-29 | 2010-12-02 | 3M Innovative Properties Company | Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same |
| KR101736920B1 (ko) * | 2009-12-15 | 2017-05-18 | 엘지디스플레이 주식회사 | 아릴기가 치환된 안트라센 화합물, 그 제조 방법 및 이를 이용한 유기 박막 트랜지스터 |
| WO2011149735A1 (en) | 2010-05-28 | 2011-12-01 | 3M Innovative Properties Company | Synthesis of silyl acetylenes |
| WO2011150020A1 (en) | 2010-05-28 | 2011-12-01 | 3M Innovative Properties Company | Synthesis of silyl acetylenes |
| CN103159919B (zh) * | 2011-12-09 | 2016-01-13 | 海洋王照明科技股份有限公司 | 氰基蒽醌基共聚物太阳能电池材料及其制备方法和应用 |
| JP6116018B2 (ja) * | 2015-01-29 | 2017-04-19 | 国立大学法人 東京大学 | 有機半導体素子 |
| US10703692B2 (en) * | 2017-02-06 | 2020-07-07 | Raytheon Company | Solid state materials with tunable dielectric response and rotational anisotropy |
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- 2008-11-20 WO PCT/US2008/084122 patent/WO2009079150A1/en not_active Ceased
- 2008-11-20 US US12/808,003 patent/US8178873B2/en not_active Expired - Fee Related
- 2008-11-20 EP EP08862829A patent/EP2232606A1/en not_active Withdrawn
- 2008-11-20 CN CN2008801253556A patent/CN101926017B/zh not_active Expired - Fee Related
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013004965A (ja) * | 2011-06-13 | 2013-01-07 | Xerox Corp | 電子デバイス |
| JPWO2014189114A1 (ja) * | 2013-05-23 | 2017-02-23 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
| WO2014189116A1 (ja) * | 2013-05-23 | 2014-11-27 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
| WO2014189114A1 (ja) * | 2013-05-23 | 2014-11-27 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
| US9929348B2 (en) | 2013-05-23 | 2018-03-27 | Fujifilm Corporation | Organic semiconductor composition comprising organic semiconductor material and polymer compound |
| JPWO2014189116A1 (ja) * | 2013-05-23 | 2017-02-23 | 富士フイルム株式会社 | 有機半導体組成物および有機薄膜トランジスタならびに電子ペーパーおよびディスプレイデバイス |
| WO2015076171A1 (ja) * | 2013-11-21 | 2015-05-28 | 株式会社ダイセル | 有機トランジスタ製造用溶剤 |
| KR20160088328A (ko) * | 2013-11-21 | 2016-07-25 | 주식회사 다이셀 | 유기 트랜지스터 제조용 용제 |
| JPWO2015076171A1 (ja) * | 2013-11-21 | 2017-03-16 | 株式会社ダイセル | 有機トランジスタ製造用溶剤 |
| US10693080B2 (en) | 2013-11-21 | 2020-06-23 | Daicel Corporation | Solvent for producing organic transistor |
| KR102237757B1 (ko) * | 2013-11-21 | 2021-04-09 | 주식회사 다이셀 | 유기 트랜지스터 제조용 용제 |
| JP2015167164A (ja) * | 2014-03-03 | 2015-09-24 | 富士フイルム株式会社 | 有機薄膜トランジスタ及びその製造方法 |
| US9799832B2 (en) | 2014-03-03 | 2017-10-24 | Fujifilm Corporation | Organic thin-film transistor and method for manufacturing same |
| WO2015133375A1 (ja) * | 2014-03-03 | 2015-09-11 | 富士フイルム株式会社 | 有機薄膜トランジスタ及びその製造方法 |
| JP2016178274A (ja) * | 2015-03-19 | 2016-10-06 | 三菱化学株式会社 | 半導体デバイス、太陽電池、太陽電池モジュール、及び組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101926017B (zh) | 2013-09-25 |
| WO2009079150A1 (en) | 2009-06-25 |
| CN101926017A (zh) | 2010-12-22 |
| US8178873B2 (en) | 2012-05-15 |
| US20100270542A1 (en) | 2010-10-28 |
| EP2232606A1 (en) | 2010-09-29 |
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