JP2020524722A5 - - Google Patents
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- JP2020524722A5 JP2020524722A5 JP2019536124A JP2019536124A JP2020524722A5 JP 2020524722 A5 JP2020524722 A5 JP 2020524722A5 JP 2019536124 A JP2019536124 A JP 2019536124A JP 2019536124 A JP2019536124 A JP 2019536124A JP 2020524722 A5 JP2020524722 A5 JP 2020524722A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- monomer
- aryl
- alkyl
- group
- 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.)
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- 239000000178 monomer Substances 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 16
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 16
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- -1 perfluoro Chemical group 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 125000005293 bicycloalkoxy group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims description 6
- 238000002834 transmittance Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- ZTGFJAPGVDKJEB-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1 Chemical compound C(C)(=O)O.C(C)(=O)O.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1 ZTGFJAPGVDKJEB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- XUTKEXDOVRWFEM-UHFFFAOYSA-N C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.Br.Br Chemical compound C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.Br.Br XUTKEXDOVRWFEM-UHFFFAOYSA-N 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- AZLJPAXHKBYMPD-UHFFFAOYSA-N [Cl-].[Cl-].C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1.C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1 Chemical compound [Cl-].[Cl-].C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1.C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1 AZLJPAXHKBYMPD-UHFFFAOYSA-N 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 1
- 239000010979 ruby Substances 0.000 claims 1
- 229910001750 ruby Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- 0 C*C1(*)C(*)(*C2(*)C(*)(*)C3C=CC2C3)C2C=CC1C2 Chemical compound C*C1(*)C(*)(*C2(*)C(*)(*)C3C=CC2C3)C2C=CC1C2 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- JSQDUFHOLSQWEG-UHFFFAOYSA-N 5-[2-(2-phenylphenoxy)ethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C(CC1CC2CC1C=C2)OC1=C(C=CC=C1)C1=CC=CC=C1 JSQDUFHOLSQWEG-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762443143P | 2017-01-06 | 2017-01-06 | |
| US62/443,143 | 2017-01-06 | ||
| US201762518967P | 2017-06-13 | 2017-06-13 | |
| US62/518,967 | 2017-06-13 | ||
| PCT/US2018/012293 WO2018129121A1 (en) | 2017-01-06 | 2018-01-04 | Polycycloolefin polymer compositions as optical materials |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020524722A JP2020524722A (ja) | 2020-08-20 |
| JP2020524722A5 true JP2020524722A5 (https=) | 2020-10-01 |
| JP6864101B2 JP6864101B2 (ja) | 2021-04-21 |
Family
ID=61193014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019536124A Active JP6864101B2 (ja) | 2017-01-06 | 2018-01-04 | 光学材料としてのポリシクロオレフィン重合体組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10626198B2 (https=) |
| EP (1) | EP3565850B1 (https=) |
| JP (1) | JP6864101B2 (https=) |
| KR (1) | KR102298455B1 (https=) |
| CN (1) | CN110191903B (https=) |
| TW (1) | TWI723243B (https=) |
| WO (1) | WO2018129121A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102513170B1 (ko) * | 2018-12-21 | 2023-03-24 | 스미토모 베이클리트 컴퍼니 리미티드 | 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료 |
| WO2020243381A1 (en) * | 2019-05-31 | 2020-12-03 | Promerus, Llc | Fast photocurable polycycloolefin compositions as optical or 3d printing materials |
| TWI850512B (zh) * | 2019-12-30 | 2024-08-01 | 日商住友電木股份有限公司 | 作為光學材料之uv活性鈀催化多環烯烴聚合物組成物 |
| US11760817B2 (en) * | 2020-06-08 | 2023-09-19 | Promerus, Llc | Mass polymerizable polycycloolefin compositions containing soluble photoacid generators |
| TWI867226B (zh) * | 2020-06-24 | 2024-12-21 | 日商住友電木股份有限公司 | 作為光學材料之受阻胺穩定型ｕｖ活性有機鈀催化聚環烯烴組成物 |
| TWI878633B (zh) * | 2020-10-30 | 2025-04-01 | 日商住友電木股份有限公司 | 熱特性改良型低損耗膜用聚環烯烴組成物 |
| KR20230095975A (ko) * | 2020-10-30 | 2023-06-29 | 프로메러스, 엘엘씨 | 저장수명이 안정적이고 덩이중합이 가능한 개선된 폴리시클로올레핀 조성물 |
| US20240279251A1 (en) * | 2021-05-14 | 2024-08-22 | 3M Innovative Properties Company | Monomer, Polymerizable Composition, and Polymers Derived Therefrom |
| TW202440749A (zh) * | 2022-12-20 | 2024-10-16 | 美商普羅梅勒斯有限公司 | 藉由熱和uv引發塊狀聚合之支撐膜 |
| JPWO2025013726A1 (https=) * | 2023-07-07 | 2025-01-16 | ||
| TW202530282A (zh) * | 2023-09-11 | 2025-08-01 | 美商普羅梅勒斯有限公司 | 微流體裝置用多環烯烴聚合物製ｕｖ－奈米壓印微影裝置 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6903171B2 (en) | 1998-10-05 | 2005-06-07 | Promerus, Llc | Polymerized cycloolefins using transition metal catalyst and end products thereof |
| EP1034196B1 (en) * | 1998-10-05 | 2005-01-12 | Promerus LLC | Catalyst and methods for polymerizing cycloolefins |
| CN101308228B (zh) * | 2003-11-21 | 2016-04-06 | 住友电木株式会社 | 光波导及其形成方法 |
| KR101230512B1 (ko) * | 2003-11-21 | 2013-02-18 | 스미토모 베이클리트 컴퍼니 리미티드 | 광-유도 열 현상형 막 및 광도파로 형성 방법 |
| US7875686B2 (en) * | 2004-08-18 | 2011-01-25 | Promerus Llc | Polycycloolefin polymeric compositions for semiconductor applications |
| JP5153227B2 (ja) | 2007-06-26 | 2013-02-27 | キヤノン株式会社 | 有機発光素子 |
| DE102009013710A1 (de) | 2009-03-20 | 2010-09-23 | Merck Patent Gmbh | Polymere aus Mischungen mit Vinylether-Monomeren |
| KR20130114120A (ko) * | 2010-09-02 | 2013-10-16 | 메르크 파텐트 게엠베하 | 전자 디바이스용 중간층 |
| JP2012121956A (ja) * | 2010-12-07 | 2012-06-28 | Sumitomo Bakelite Co Ltd | 付加型ノルボルネン系樹脂、その製造方法、該樹脂を含む樹脂組成物、ならびに該樹脂を含む成形体および該成形体を含む複合部材 |
| EP2898551B1 (en) * | 2012-09-21 | 2020-04-22 | Merck Patent GmbH | Organic semiconductor formulations |
| JP6225294B2 (ja) * | 2014-08-15 | 2017-11-01 | プロメラス， エルエルシー | ポリシクロオレフィンブロックポリマー、その製造方法、および重合組成物 |
| TWI675059B (zh) * | 2015-09-01 | 2019-10-21 | 日商住友電木股份有限公司 | 作爲光學材料的聚環烯烴聚合物組成物 |
-
2018
- 2018-01-03 TW TW107100205A patent/TWI723243B/zh active
- 2018-01-04 CN CN201880006158.6A patent/CN110191903B/zh active Active
- 2018-01-04 WO PCT/US2018/012293 patent/WO2018129121A1/en not_active Ceased
- 2018-01-04 US US15/861,801 patent/US10626198B2/en active Active
- 2018-01-04 EP EP18704633.9A patent/EP3565850B1/en active Active
- 2018-01-04 KR KR1020197021093A patent/KR102298455B1/ko active Active
- 2018-01-04 JP JP2019536124A patent/JP6864101B2/ja active Active
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