CN104956508B - 溶液工艺用有机半导体材料和有机半导体设备 - Google Patents
溶液工艺用有机半导体材料和有机半导体设备 Download PDFInfo
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- CN104956508B CN104956508B CN201480005535.6A CN201480005535A CN104956508B CN 104956508 B CN104956508 B CN 104956508B CN 201480005535 A CN201480005535 A CN 201480005535A CN 104956508 B CN104956508 B CN 104956508B
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052798 chalcogen Inorganic materials 0.000 claims abstract description 4
- 150000001787 chalcogens Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 56
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 239000000126 substance Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
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- 239000000203 mixture Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 9
- 238000011049 filling Methods 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
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- CZWHMRTTWFJMBC-UHFFFAOYSA-N dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene Chemical compound C1=CC=C2C=C(SC=3C4=CC5=CC=CC=C5C=C4SC=33)C3=CC2=C1 CZWHMRTTWFJMBC-UHFFFAOYSA-N 0.000 description 7
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- 101000800646 Homo sapiens DNA nucleotidylexotransferase Proteins 0.000 description 6
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- 238000002441 X-ray diffraction Methods 0.000 description 3
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 3
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- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
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- 239000013078 crystal Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
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- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
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- VIFIHLXNOOCGLJ-UHFFFAOYSA-N trichloro(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CC[Si](Cl)(Cl)Cl VIFIHLXNOOCGLJ-UHFFFAOYSA-N 0.000 description 1
- HLWCOIUDOLYBGD-UHFFFAOYSA-N trichloro(decyl)silane Chemical class CCCCCCCCCC[Si](Cl)(Cl)Cl HLWCOIUDOLYBGD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thin Film Transistor (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013009153 | 2013-01-22 | ||
| JP2013-009153 | 2013-01-22 | ||
| JP2013175678 | 2013-08-27 | ||
| JP2013-175678 | 2013-08-27 | ||
| PCT/JP2014/051213 WO2014115749A1 (ja) | 2013-01-22 | 2014-01-22 | 溶液プロセス用有機半導体材料及び有機半導体デバイス |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104956508A CN104956508A (zh) | 2015-09-30 |
| CN104956508B true CN104956508B (zh) | 2017-07-21 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480005535.6A Expired - Fee Related CN104956508B (zh) | 2013-01-22 | 2014-01-22 | 溶液工艺用有机半导体材料和有机半导体设备 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6080870B2 (ko) |
| KR (1) | KR102101242B1 (ko) |
| CN (1) | CN104956508B (ko) |
| TW (1) | TW201444852A (ko) |
| WO (1) | WO2014115749A1 (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101703599B1 (ko) | 2015-07-31 | 2017-02-07 | 현대자동차 주식회사 | 루프 레이저 브레이징 시스템 |
| JP6654517B2 (ja) * | 2016-06-21 | 2020-02-26 | 山本化成株式会社 | 有機トランジスタ |
| JP6910880B2 (ja) * | 2016-08-03 | 2021-07-28 | 日本化薬株式会社 | 有機光電変換素子、有機光電変換素子用材料及びこれらを用いた有機撮像素子 |
| JP2018190755A (ja) * | 2017-04-28 | 2018-11-29 | 日本化薬株式会社 | 撮像素子用光電変換素子 |
| JP6906357B2 (ja) * | 2017-04-28 | 2021-07-21 | 日本化薬株式会社 | 撮像素子用光電変換素子 |
| EP3697780B1 (en) | 2017-10-19 | 2022-07-27 | Clap Co., Ltd. | New substituted benzonaphthathiophene compounds for organic electronics |
| WO2019101569A1 (en) * | 2017-11-21 | 2019-05-31 | Basf Se | Sulfonium salts of dntt and related compounds as soluble photocleavable precursors for organic semiconductors for use in organic field-effect transistors |
| US11296290B2 (en) | 2018-03-07 | 2022-04-05 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
| JP7241346B2 (ja) * | 2019-05-21 | 2023-03-17 | 国立大学法人東北大学 | 芳香族化合物の製造方法 |
| KR20220063189A (ko) | 2019-09-17 | 2022-05-17 | 닛뽄 가야쿠 가부시키가이샤 | 축합 다환 방향족 화합물 |
| JP7317301B2 (ja) * | 2019-11-13 | 2023-07-31 | 日本化薬株式会社 | 有機半導体化合物及びその用途 |
| CN110849252B (zh) * | 2019-11-14 | 2021-06-18 | 东北师范大学 | 一种制备大面积可贴合半导体型接近传感器的方法 |
| TW202136272A (zh) * | 2019-12-10 | 2021-10-01 | 日商日本化藥股份有限公司 | 縮合多環芳香族化合物 |
| WO2023189381A1 (ja) * | 2022-03-30 | 2023-10-05 | ソニーグループ株式会社 | 発光素子および電子機器 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101528753A (zh) * | 2006-10-25 | 2009-09-09 | 国立大学法人广岛大学 | 新型缩合多环芳香族化合物及其制造方法和用途 |
| CN101529609A (zh) * | 2006-10-20 | 2009-09-09 | 日本化药株式会社 | 场效应晶体管 |
| CN102333780A (zh) * | 2009-02-27 | 2012-01-25 | 国立大学法人广岛大学 | 场效应晶体管 |
| CN103958520A (zh) * | 2011-09-12 | 2014-07-30 | 破立纪元有限公司 | 具有半导体特性的化合物及相关组合物和装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5428104B2 (ja) * | 2008-05-23 | 2014-02-26 | 日本化薬株式会社 | 有機半導体組成物 |
| WO2012115236A1 (ja) * | 2011-02-25 | 2012-08-30 | 国立大学法人広島大学 | 新規複素環式化合物及びその中間体の製造方法並びにその用途 |
-
2014
- 2014-01-22 WO PCT/JP2014/051213 patent/WO2014115749A1/ja active Application Filing
- 2014-01-22 KR KR1020157022803A patent/KR102101242B1/ko active IP Right Grant
- 2014-01-22 JP JP2014558587A patent/JP6080870B2/ja active Active
- 2014-01-22 TW TW103102269A patent/TW201444852A/zh unknown
- 2014-01-22 CN CN201480005535.6A patent/CN104956508B/zh not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101529609A (zh) * | 2006-10-20 | 2009-09-09 | 日本化药株式会社 | 场效应晶体管 |
| CN101528753A (zh) * | 2006-10-25 | 2009-09-09 | 国立大学法人广岛大学 | 新型缩合多环芳香族化合物及其制造方法和用途 |
| CN102333780A (zh) * | 2009-02-27 | 2012-01-25 | 国立大学法人广岛大学 | 场效应晶体管 |
| CN103958520A (zh) * | 2011-09-12 | 2014-07-30 | 破立纪元有限公司 | 具有半导体特性的化合物及相关组合物和装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2014115749A1 (ja) | 2017-01-26 |
| KR102101242B1 (ko) | 2020-04-17 |
| JP6080870B2 (ja) | 2017-02-15 |
| TW201444852A (zh) | 2014-12-01 |
| WO2014115749A1 (ja) | 2014-07-31 |
| KR20150108918A (ko) | 2015-09-30 |
| CN104956508A (zh) | 2015-09-30 |
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