TW201109360A - A process for polymerising (hetero) aromatic compounds - Google Patents
A process for polymerising (hetero) aromatic compounds Download PDFInfo
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- TW201109360A TW201109360A TW099117069A TW99117069A TW201109360A TW 201109360 A TW201109360 A TW 201109360A TW 099117069 A TW099117069 A TW 099117069A TW 99117069 A TW99117069 A TW 99117069A TW 201109360 A TW201109360 A TW 201109360A
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- 238000000034 method Methods 0.000 title claims abstract description 32
- 125000005842 heteroatom Chemical group 0.000 title claims abstract description 26
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 10
- 125000005418 aryl aryl group Chemical group 0.000 claims abstract description 7
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- -1 deutero Chemical group 0.000 claims description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 31
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
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- 125000000524 functional group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
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- 125000001424 substituent group Chemical group 0.000 claims description 11
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
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- 125000003342 alkenyl group Chemical group 0.000 claims description 5
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- 238000006467 substitution reaction Methods 0.000 claims description 4
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- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
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- 238000001514 detection method Methods 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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| DE112010002086B4 (de) * | 2009-05-27 | 2020-07-09 | Basf Se | Verfahren zum Polymerisieren von (hetero)aromatischen Verbindungen |
| WO2011144566A2 (en) | 2010-05-19 | 2011-11-24 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| KR20130094773A (ko) | 2010-06-24 | 2013-08-26 | 바스프 에스이 | 온/오프 전류비가 개선되고 임계 이동이 제어가능한 유기 전계 효과 트랜지스터 |
| WO2012017005A2 (en) | 2010-08-05 | 2012-02-09 | Basf Se | Polymers based on benzodiones |
| US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| CN103189971B (zh) | 2010-11-01 | 2016-02-17 | 巴斯夫欧洲公司 | 作为电介质的聚酰亚胺 |
| US9187600B2 (en) | 2010-11-01 | 2015-11-17 | Basf Se | Polyimides as dielectric |
| US20130228771A1 (en) | 2010-12-22 | 2013-09-05 | Basf Se | Semiconductor structure and method for its production |
| WO2012165128A1 (ja) * | 2011-05-27 | 2012-12-06 | 住友化学株式会社 | 高分子化合物及び有機光電変換素子 |
| CN103619855B (zh) | 2011-06-22 | 2017-08-08 | 巴斯夫欧洲公司 | 用于有机半导体器件的二酮基吡咯并吡咯低聚物 |
| US9209412B2 (en) | 2011-09-02 | 2015-12-08 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
| EP2764034B1 (en) | 2011-10-04 | 2023-08-30 | CLAP Co., Ltd. | Polymers based on benzodiones |
| KR20140101788A (ko) | 2011-11-15 | 2014-08-20 | 바스프 에스이 | 유기 반도체 소자 및 이의 제조 방법 |
| WO2013083506A1 (en) | 2011-12-07 | 2013-06-13 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| CN103975453B (zh) | 2011-12-07 | 2018-01-30 | 巴斯夫欧洲公司 | 有机场效应晶体管 |
| CN104185648A (zh) | 2012-04-02 | 2014-12-03 | 巴斯夫欧洲公司 | 用于电子应用的菲并[9,10-b]呋喃聚合物及小分子 |
| JP6395702B2 (ja) | 2012-04-04 | 2018-09-26 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ジケトピロロピロールポリマーおよび小分子 |
| CN104470932A (zh) | 2012-07-23 | 2015-03-25 | 巴斯夫欧洲公司 | 用于电子应用的二噻吩并苯并呋喃聚合物和小分子 |
| WO2014072292A2 (en) | 2012-11-07 | 2014-05-15 | Basf Se | Polymers based on naphthodiones |
| EP2928940B1 (en) | 2012-12-04 | 2021-03-03 | CLAP Co., Ltd. | Functionalized benzodithiophene polymers for electronic application |
| WO2014180704A1 (en) | 2013-05-06 | 2014-11-13 | Basf Se | Soluble cyclic imides containing polymers as dielectrics in organic electronic applications |
| EP3013906B1 (en) | 2013-06-24 | 2020-03-25 | Basf Se | Polymers based on fused diketopyrrolopyrroles |
| EP2818493A1 (en) | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| KR101961985B1 (ko) | 2013-06-27 | 2019-03-25 | 바스프 에스이 | 유전체로서의 복분해 중합체 |
| KR101754044B1 (ko) | 2013-07-08 | 2017-07-04 | 바스프 에스이 | 아지드계 가교제 |
| JP5962844B2 (ja) * | 2013-09-11 | 2016-08-03 | 住友化学株式会社 | 高分子化合物およびそれを用いた発光素子 |
| WO2016046659A1 (en) | 2014-09-25 | 2016-03-31 | Basf Se | Ether-based polymers as photo-crosslinkable dielectrics |
| KR20170100552A (ko) | 2014-12-29 | 2017-09-04 | 다우 글로벌 테크놀로지스 엘엘씨 | 전하 수송 물질로서의 2,3-이치환된 인돌을 갖는 조성물, 및 이 조성물로부터 제작된 디스플레이 장치 |
| KR102570660B1 (ko) | 2015-10-21 | 2023-08-25 | 주식회사 클랩 | 디피롤로[1,2-b:1',2'-g][2,6]나프티리딘-5,11-디온 기재 중합체 및 화합물 |
| US11384197B2 (en) | 2016-05-25 | 2022-07-12 | Clap Co., Ltd. | Semiconductors |
| US11319396B2 (en) | 2016-09-27 | 2022-05-03 | Basf Se | Star-shaped and triblock polymers with enhanced crosslinkability |
| WO2018060015A1 (en) | 2016-09-27 | 2018-04-05 | Basf Se | Star-shaped styrene polymers with enhanced glass transition temperature |
| WO2019170481A1 (en) | 2018-03-07 | 2019-09-12 | Basf Se | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
| US20200411781A1 (en) | 2018-03-08 | 2020-12-31 | Clap Co., Ltd. | Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material |
| KR102457044B1 (ko) | 2018-06-26 | 2022-10-21 | 주식회사 클랩 | 유전체로서의 비닐에테르계 고분자 |
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| TWI290164B (en) * | 1999-08-26 | 2007-11-21 | Ciba Sc Holding Ag | DPP-containing conjugated polymers and electroluminescent devices |
| EP1078970B1 (en) | 1999-08-26 | 2004-03-17 | Ciba SC Holding AG | DPP-containing conjugated polymers and electroluminescent devices |
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| WO2005049695A1 (en) | 2003-10-28 | 2005-06-02 | Ciba Specialty Chemicals Holding Inc. | Novel diketopyrrolopyrrole polymers |
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| JP5432458B2 (ja) * | 2007-02-01 | 2014-03-05 | 学校法人神奈川大学 | 基材に芳香族ポリマーが結合した構造体の製造方法、並びに、導電性基材に結合した芳香族ポリマー鎖を有してなる構造体、及び該構造体を含む電子素子 |
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| CN107099023B (zh) | 2008-10-31 | 2019-10-22 | 巴斯夫欧洲公司 | 用于有机场效应晶体管的二酮吡咯并吡咯聚合物 |
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| WO2010136352A1 (en) | 2010-12-02 |
| JP5623512B2 (ja) | 2014-11-12 |
| DE112010002086A5 (de) | 2012-04-19 |
| US20120142872A1 (en) | 2012-06-07 |
| JP2012528214A (ja) | 2012-11-12 |
| US8835579B2 (en) | 2014-09-16 |
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