JP2004115794A5 - - Google Patents
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- Publication number
- JP2004115794A5 JP2004115794A5 JP2003322784A JP2003322784A JP2004115794A5 JP 2004115794 A5 JP2004115794 A5 JP 2004115794A5 JP 2003322784 A JP2003322784 A JP 2003322784A JP 2003322784 A JP2003322784 A JP 2003322784A JP 2004115794 A5 JP2004115794 A5 JP 2004115794A5
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- independently
- oligomer
- monomer
- polymerizable
- 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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- 229920000642 polymer Polymers 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 19
- 239000004973 liquid crystal related substance Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229920006254 polymer film Polymers 0.000 claims 6
- 239000010408 film Substances 0.000 claims 2
- 239000010409 thin film Substances 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229920000106 Liquid crystal polymer Polymers 0.000 claims 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000007772 electrode material Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- -1 alkyl Fluorene Chemical compound 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000011532 electronic conductor Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005266 side chain polymer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02020711 | 2002-09-14 | ||
| EP02020711.4 | 2002-09-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004115794A JP2004115794A (ja) | 2004-04-15 |
| JP2004115794A5 true JP2004115794A5 (enExample) | 2006-11-02 |
| JP4942910B2 JP4942910B2 (ja) | 2012-05-30 |
Family
ID=32241245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003322784A Expired - Fee Related JP4942910B2 (ja) | 2002-09-14 | 2003-09-16 | モノマー、オリゴマーおよびポリ（３−アルキニルチオフェン）ならびにそれらの電荷移動材料としての使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7541425B2 (enExample) |
| JP (1) | JP4942910B2 (enExample) |
| AT (1) | ATE307840T1 (enExample) |
| DE (1) | DE60302025T2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7329896B2 (en) * | 2001-07-09 | 2008-02-12 | Merck Patent Gmbh | Polymerizable charge transport compounds |
| KR101120303B1 (ko) * | 2003-08-06 | 2012-03-07 | 메르크 파텐트 게엠베하 | 위치규칙적인 중합체의 제조방법 |
| US7294850B2 (en) * | 2004-06-10 | 2007-11-13 | Xerox Corporation | Device with small molecular thiophene compound having divalent linkage |
| US7102017B2 (en) * | 2004-06-10 | 2006-09-05 | Xerox Corporation | Processes to prepare small molecular thiophene compounds |
| US7838623B2 (en) * | 2004-09-14 | 2010-11-23 | Corning Incorporated | Fused thiophenes, methods for making fused thiophenes, and uses thereof |
| TW200621789A (en) * | 2004-09-14 | 2006-07-01 | Corning Inc | Fused thiophenes, methods for making fused thiophens, and uses thereof |
| US7893191B2 (en) * | 2007-02-28 | 2011-02-22 | Corning Incorporated | Fused thiophenes, methods for making fused thiophenes, and uses thereof |
| US20060131567A1 (en) * | 2004-12-20 | 2006-06-22 | Jie Liu | Surface modified electrodes and devices using reduced organic materials |
| WO2006087680A1 (en) * | 2005-02-18 | 2006-08-24 | Koninklijke Philips Electronics N.V. | Electronic device |
| JP4934995B2 (ja) * | 2005-06-03 | 2012-05-23 | 大日本印刷株式会社 | 有機半導体材料、有機半導体構造物及び有機半導体装置 |
| JP2007019086A (ja) * | 2005-07-05 | 2007-01-25 | Toyota Central Res & Dev Lab Inc | 有機半導体材料、それを用いた半導体装置及び電界効果トランジスタ |
| JP2007088222A (ja) * | 2005-09-22 | 2007-04-05 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| US7667230B2 (en) * | 2006-03-31 | 2010-02-23 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers |
| US8049205B2 (en) * | 2006-04-06 | 2011-11-01 | Xerox Corporation | Poly(alkynylthiophene)s and electronic devices generated therefrom |
| US7705111B2 (en) * | 2006-04-06 | 2010-04-27 | Xerox Corporation | Poly(alkynylthiophene)s |
| JP5157079B2 (ja) * | 2006-04-19 | 2013-03-06 | コニカミノルタホールディングス株式会社 | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| KR20090033909A (ko) * | 2006-07-26 | 2009-04-06 | 메르크 파텐트 게엠베하 | 치환 벤조디티오펜 및 벤조디셀레노펜 |
| KR100847987B1 (ko) * | 2007-02-27 | 2008-07-22 | 삼성전자주식회사 | 탄소나노튜브용 분산제 및 이를 포함하는 탄소나노튜브조성물 |
| KR101652533B1 (ko) * | 2008-03-31 | 2016-08-30 | 코닝 인코포레이티드 | 융합 티오펜 화합물, 이들을 제조하는 방법 및 이들의 용도 |
| US8815415B2 (en) * | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
| US8895693B2 (en) | 2010-06-25 | 2014-11-25 | Samsung Electronics Co., Ltd. | Electron-donating polymers and organic solar cells including the same |
| JP5838975B2 (ja) * | 2011-02-18 | 2016-01-06 | コニカミノルタ株式会社 | 有機光電変換素子および太陽電池 |
| KR101853395B1 (ko) | 2011-05-23 | 2018-04-30 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 태양 전지 |
| KR101777326B1 (ko) | 2011-10-05 | 2017-09-12 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 유기 태양 전지 |
| MX2022002816A (es) * | 2019-09-06 | 2022-08-25 | Michael John Arnold | Composiciones polimericas organicas. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2984103B2 (ja) * | 1991-09-02 | 1999-11-29 | 勝美 吉野 | 有機発光素子 |
| KR100207568B1 (ko) * | 1994-08-27 | 1999-07-15 | 손욱 | 전도성 측쇄형 액정화합물 및 이를 사용한 배향막 |
| WO1997032914A1 (de) * | 1996-03-06 | 1997-09-12 | Basf Aktiengesellschaft | Substituierte polythiophene, verfahren zu deren herstellung, und deren verwendung |
| JP2001196664A (ja) * | 2000-01-12 | 2001-07-19 | Japan Science & Technology Corp | 立体規則性ポリチオフェン誘導体から成る光電変換素子用光キャリアー生成および輸送材料薄膜 |
-
2003
- 2003-08-13 AT AT03018346T patent/ATE307840T1/de not_active IP Right Cessation
- 2003-08-13 DE DE60302025T patent/DE60302025T2/de not_active Expired - Lifetime
- 2003-09-15 US US10/661,812 patent/US7541425B2/en active Active
- 2003-09-16 JP JP2003322784A patent/JP4942910B2/ja not_active Expired - Fee Related
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