JP2007051289A5 - - Google Patents
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- Publication number
- JP2007051289A5 JP2007051289A5 JP2006221386A JP2006221386A JP2007051289A5 JP 2007051289 A5 JP2007051289 A5 JP 2007051289A5 JP 2006221386 A JP2006221386 A JP 2006221386A JP 2006221386 A JP2006221386 A JP 2006221386A JP 2007051289 A5 JP2007051289 A5 JP 2007051289A5
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- JP
- Japan
- Prior art keywords
- groups
- independently
- aryl
- functional group
- sir
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 150000004820 halides Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052740 iodine Inorganic materials 0.000 claims 7
- -1 phosphonium compound Chemical class 0.000 claims 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 5
- 239000002585 base Substances 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 101150003085 Pdcl gene Proteins 0.000 claims 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- 125000000732 arylene group Chemical group 0.000 claims 4
- 150000003003 phosphines Chemical class 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 150000004714 phosphonium salts Chemical class 0.000 claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 2
- 150000002390 heteroarenes Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910018286 SbF 6 Inorganic materials 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- WBMJFMFJCWPAIT-UHFFFAOYSA-N ditert-butyl(ditert-butylphosphanylmethyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CP(C(C)(C)C)C(C)(C)C WBMJFMFJCWPAIT-UHFFFAOYSA-N 0.000 claims 1
- 150000002222 fluorine compounds Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05017718 | 2005-08-16 | ||
| EP05017718.7 | 2005-08-16 | ||
| EP06002595.4 | 2006-02-09 | ||
| EP06002595 | 2006-02-09 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014000657A Division JP2014129533A (ja) | 2005-08-16 | 2014-01-06 | チオフェンまたはセレノフェン化合物の重合方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007051289A JP2007051289A (ja) | 2007-03-01 |
| JP2007051289A5 true JP2007051289A5 (enExample) | 2012-07-12 |
| JP5739598B2 JP5739598B2 (ja) | 2015-06-24 |
Family
ID=37802786
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006221386A Expired - Fee Related JP5739598B2 (ja) | 2005-08-16 | 2006-08-15 | チオフェンまたはセレノフェン化合物の重合方法 |
| JP2014000657A Pending JP2014129533A (ja) | 2005-08-16 | 2014-01-06 | チオフェンまたはセレノフェン化合物の重合方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014000657A Pending JP2014129533A (ja) | 2005-08-16 | 2014-01-06 | チオフェンまたはセレノフェン化合物の重合方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8501902B2 (enExample) |
| JP (2) | JP5739598B2 (enExample) |
| KR (1) | KR101314902B1 (enExample) |
| AT (1) | ATE509055T1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE509055T1 (de) * | 2005-08-16 | 2011-05-15 | Merck Patent Gmbh | Verfahren zur polymerisation von thiophen- oder selenophenderivaten |
| JP5545383B2 (ja) * | 2006-07-18 | 2014-07-09 | 日立化成株式会社 | 有機エレクトロニクス素子の製造方法及び有機エレクトロルミネッセンス素子の製造方法 |
| CN101563389B (zh) * | 2006-12-22 | 2013-07-17 | 默克专利股份有限公司 | 包含稠合硒吩的聚合物 |
| US8723163B2 (en) * | 2008-03-12 | 2014-05-13 | Sumitomo Chemical Company, Limited | Organic photoelectric converter |
| DE112010002086B4 (de) * | 2009-05-27 | 2020-07-09 | Basf Se | Verfahren zum Polymerisieren von (hetero)aromatischen Verbindungen |
| WO2012143081A1 (en) * | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Conjugated polymers |
| KR101424978B1 (ko) * | 2012-05-24 | 2014-07-31 | 경상대학교산학협력단 | 길만시약 화합물을 이용한 헤테로 융합고리 화합물의 신규한 제조방법 |
| JP6103585B2 (ja) * | 2013-03-27 | 2017-03-29 | オリヱント化学工業株式会社 | チエノチオフェン−ベンゾジチオフェン共重合体の製造方法 |
| WO2015108360A1 (ko) * | 2014-01-17 | 2015-07-23 | 경상대학교산학협력단 | 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체 |
| CN105482082B (zh) * | 2014-09-19 | 2018-11-06 | 中国科学院苏州纳米技术与纳米仿生研究所 | 结构规整聚噻吩及其合成方法 |
| WO2018220785A1 (ja) * | 2017-06-01 | 2018-12-06 | 住友化学株式会社 | 高分子化合物の製造方法 |
| KR102631550B1 (ko) * | 2018-09-20 | 2024-01-30 | 주식회사 엘지화학 | 중합체 제조방법 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5892244A (en) * | 1989-01-10 | 1999-04-06 | Mitsubishi Denki Kabushiki Kaisha | Field effect transistor including πconjugate polymer and liquid crystal display including the field effect transistor |
| US5198153A (en) * | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
| WO1996021659A1 (en) | 1995-01-10 | 1996-07-18 | University Of Technology, Sydney | Organic semiconductor |
| US5998804A (en) * | 1997-07-03 | 1999-12-07 | Hna Holdings, Inc. | Transistors incorporating substrates comprising liquid crystal polymers |
| EP0889350A1 (en) | 1997-07-03 | 1999-01-07 | ETHZ Institut für Polymere | Photoluminescent display devices (I) |
| DE19739774A1 (de) * | 1997-09-10 | 1999-03-11 | Basf Ag | Polyselenophene als Materialien mit nichtlinear optischen Eigenschaften |
| EP0902043A3 (de) * | 1997-09-10 | 1999-08-11 | Basf Aktiengesellschaft | Polyselenophene, Verfahren zu deren Herstellung, und deren Verwendung |
| US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| US7223879B2 (en) * | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| DE60035970T2 (de) | 1999-03-05 | 2008-05-15 | Cambridge Display Technology Ltd. | Polymerherstellung |
| CN100461486C (zh) | 1999-06-21 | 2009-02-11 | 剑桥企业有限公司 | 用于有机薄膜晶体管的取向聚合物 |
| US6824706B2 (en) * | 2001-07-25 | 2004-11-30 | Merck Patent Gesellschaft Mit Beschrank Haftung | Mono-, Oligo- and poly-difluorovinyl-(hetero)arylenes, their synthesis and their use as charge transport materials |
| GB0125621D0 (en) | 2001-10-25 | 2001-12-19 | Cambridge Display Technology | Polymer preparation |
| GB0125622D0 (en) * | 2001-10-25 | 2001-12-19 | Cambridge Display Tech Ltd | Method of polymerisation |
| DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
| US6849348B2 (en) * | 2002-12-31 | 2005-02-01 | Eastman Kodak Company | Complex fluorene-containing compounds |
| US8242235B2 (en) * | 2003-06-05 | 2012-08-14 | Hitachi Chemical Co., Ltd. | Purification process of electroluminescent material, electroluminescent material and electroluminescent device |
| FR2858222A1 (fr) | 2003-07-16 | 2005-02-04 | Oreal | Composition comprenant un polymere conducteur et un agent oxydant,procede de deformation permanente la mettant en oeuvre |
| EP1510535B1 (en) * | 2003-08-28 | 2008-11-05 | MERCK PATENT GmbH | Mono-, Oligo- and Polythieno(2,3-b)thiophenes |
| EP1688424B1 (en) * | 2003-11-28 | 2016-01-13 | Hokko Chemical Industry Co., Ltd. | Phosphonium borate compound and method of using the same |
| EP1751166B1 (en) | 2004-05-18 | 2009-10-28 | MERCK PATENT GmbH | Mono-, oligo- and polythieno[3,2-b]thiophenes |
| JP5474299B2 (ja) * | 2004-08-21 | 2014-04-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | チエノ［２，３−ｂ］チオフェンのモノマー、オリゴマーおよびポリマー |
| WO2006094645A1 (en) | 2005-03-11 | 2006-09-14 | Merck Patent Gmbh | Monomers, oligomers and polymers comprising thiophene and selenophene |
| ATE509055T1 (de) * | 2005-08-16 | 2011-05-15 | Merck Patent Gmbh | Verfahren zur polymerisation von thiophen- oder selenophenderivaten |
-
2006
- 2006-07-18 AT AT06014918T patent/ATE509055T1/de not_active IP Right Cessation
- 2006-08-14 KR KR1020060076595A patent/KR101314902B1/ko not_active Expired - Fee Related
- 2006-08-15 JP JP2006221386A patent/JP5739598B2/ja not_active Expired - Fee Related
- 2006-08-15 US US11/504,114 patent/US8501902B2/en not_active Expired - Fee Related
-
2014
- 2014-01-06 JP JP2014000657A patent/JP2014129533A/ja active Pending
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