JP2018508824A5 - - Google Patents
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- JP2018508824A5 JP2018508824A5 JP2017542905A JP2017542905A JP2018508824A5 JP 2018508824 A5 JP2018508824 A5 JP 2018508824A5 JP 2017542905 A JP2017542905 A JP 2017542905A JP 2017542905 A JP2017542905 A JP 2017542905A JP 2018508824 A5 JP2018508824 A5 JP 2018508824A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- aryl
- branched
- formula
- 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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- 239000000203 mixture Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- -1 VIII Chemical compound 0.000 claims description 25
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 8
- DKYWVDODHFEZIM-UHFFFAOYSA-M 2-(3-benzoylphenyl)propanoate Chemical compound [O-]C(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-M 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- BEHBBKCBARHMJQ-UHFFFAOYSA-N 5-(2-phenylethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCC1=CC=CC=C1 BEHBBKCBARHMJQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 238000007142 ring opening reaction Methods 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 5
- FZNZZYVWAIIDEF-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-hydroxypiperidine-1-carboxylate Chemical compound C1CC(O)CCN1C(=O)OCC1=CC=CC=C1[N+]([O-])=O FZNZZYVWAIIDEF-UHFFFAOYSA-N 0.000 claims description 4
- GXPGUGRGRLIUPX-UHFFFAOYSA-N (4,5-dimethoxy-2-nitrophenyl)methyl 2,6-dimethylpiperidine-1-carboxylate Chemical compound C1=C(OC)C(OC)=CC(COC(=O)N2C(CCCC2C)C)=C1[N+]([O-])=O GXPGUGRGRLIUPX-UHFFFAOYSA-N 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 4
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 claims description 4
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical group C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 238000004377 microelectronic Methods 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000005693 optoelectronics Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- QECCQGLIYMMHCR-UHFFFAOYSA-N 2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane Chemical group C1OC1COCC(COCC1OC1)(CC)COCC1CO1 QECCQGLIYMMHCR-UHFFFAOYSA-N 0.000 claims description 3
- UCRXZJYCOMRCER-UHFFFAOYSA-N 2-[n,n'-di(propan-2-yl)carbamimidoyl]-1,1,3,3-tetramethylguanidine Chemical compound CC(C)NC(=NC(C)C)N=C(N(C)C)N(C)C UCRXZJYCOMRCER-UHFFFAOYSA-N 0.000 claims description 3
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 2
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 2
- RYRTYXMDSKQGDT-UHFFFAOYSA-N 5-(3-methoxybutoxy)-1-methylbicyclo[2.2.1]hept-2-ene Chemical compound COC(CCOC1C2C=CC(C1)(C2)C)C RYRTYXMDSKQGDT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005293 bicycloalkoxy group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 239000010979 ruby Substances 0.000 claims 1
- 229910001750 ruby Inorganic materials 0.000 claims 1
- NIQLOLNJWXWZHX-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound C1C2C(CC(O)(C(F)(F)F)C(F)(F)F)CC1C=C2 NIQLOLNJWXWZHX-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZSRIIBBLZOXFPK-UHFFFAOYSA-N 5-(3-methoxypropoxy)-1-methylbicyclo[2.2.1]hept-2-ene Chemical compound COCCCOC1C2C=CC(C1)(C2)C ZSRIIBBLZOXFPK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 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 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562117774P | 2015-02-18 | 2015-02-18 | |
| US62/117,774 | 2015-02-18 | ||
| PCT/US2016/017656 WO2016133795A1 (en) | 2015-02-18 | 2016-02-12 | Photoimageable polyolefin compositions containing photobase generators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018508824A JP2018508824A (ja) | 2018-03-29 |
| JP2018508824A5 true JP2018508824A5 (https=) | 2018-08-16 |
| JP6513208B2 JP6513208B2 (ja) | 2019-05-15 |
Family
ID=55487111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017542905A Active JP6513208B2 (ja) | 2015-02-18 | 2016-02-12 | 光塩基発生剤を含有する光イメージ化可能なポリオレフィン組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US9952507B2 (https=) |
| JP (1) | JP6513208B2 (https=) |
| KR (1) | KR101998338B1 (https=) |
| CN (1) | CN107407872B (https=) |
| TW (1) | TWI652281B (https=) |
| WO (1) | WO2016133795A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180088652A (ko) * | 2015-11-30 | 2018-08-06 | 프로메러스, 엘엘씨 | 광산발생제 및 염기 함유 영구유전체조성물 |
| TWI732111B (zh) * | 2017-03-28 | 2021-07-01 | 日商住友電木股份有限公司 | 感光性組成物、彩色濾光片及由其衍生之微透鏡 |
| TWI758525B (zh) | 2017-08-10 | 2022-03-21 | 日商住友電木股份有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
| WO2021076131A1 (en) * | 2019-10-17 | 2021-04-22 | Promerus, Llc | Photosensitive compositions and applications thereof |
| TWI834019B (zh) * | 2020-01-09 | 2024-03-01 | 日商住友電木股份有限公司 | 作為3d列印材料之穩定本體聚合型多環烯烴組成物及其製備方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5563011A (en) * | 1993-04-21 | 1996-10-08 | Shipley Company Inc. | Color filter assembly |
| JP4054477B2 (ja) * | 1998-04-08 | 2008-02-27 | キヤノン株式会社 | 同一相手に対して複数の通信チャネルを用いた通信を行なうことが可能な通信装置、及びその制御方法 |
| US6849377B2 (en) * | 1998-09-23 | 2005-02-01 | E. I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| KR100481601B1 (ko) * | 1999-09-21 | 2005-04-08 | 주식회사 하이닉스반도체 | 광산 발생제와 함께 광염기 발생제를 포함하는 포토레지스트 조성물 |
| AU1603101A (en) * | 1999-11-17 | 2001-05-30 | E.I. Du Pont De Nemours And Company | Nitrile/fluoroalcohol-containing photoresists and associated processes for microlithography |
| EP1246013A3 (en) * | 2001-03-30 | 2003-11-19 | E.I. Du Pont De Nemours And Company | Photoresists, polymers and processes for microlithography |
| US6737215B2 (en) * | 2001-05-11 | 2004-05-18 | Clariant Finance (Bvi) Ltd | Photoresist composition for deep ultraviolet lithography |
| US8030425B2 (en) * | 2002-07-03 | 2011-10-04 | Promerus Llc | Photosensitive compositions based on polycyclic polymers for low stress, high temperature films |
| CN101031595A (zh) * | 2003-10-31 | 2007-09-05 | 普罗米鲁斯有限责任公司 | 用于环烯烃潜聚合的单组分阳离子钯前引发剂 |
| KR101252321B1 (ko) * | 2005-06-30 | 2013-04-08 | 도레이 카부시키가이샤 | 감광성 수지 조성물 및 접착 개량제 |
| WO2010113813A1 (ja) * | 2009-03-31 | 2010-10-07 | 大日本印刷株式会社 | 塩基発生剤、感光性樹脂組成物、当該感光性樹脂組成物からなるパターン形成用材料、当該感光性樹脂組成物を用いたパターン形成方法並びに物品 |
| US20150007950A1 (en) * | 2011-12-27 | 2015-01-08 | Allure Home Creations Co., Inc. | Curtain hanging assembly |
| KR101572049B1 (ko) * | 2012-09-25 | 2015-11-26 | 프로메러스, 엘엘씨 | 사이클로올레핀성 중합체를 함유하는 말레이미드 및 그의 용도 |
| JP5803957B2 (ja) * | 2013-03-05 | 2015-11-04 | 信越化学工業株式会社 | パターン形成方法及びレジスト組成物 |
| WO2014176490A1 (en) * | 2013-04-26 | 2014-10-30 | Promerus, Llc | Photosensitive compositions and applications thereof |
| JP2015007770A (ja) * | 2013-05-29 | 2015-01-15 | 住友ベークライト株式会社 | 感光性樹脂組成物および電子装置 |
| JP6369132B2 (ja) * | 2013-06-28 | 2018-08-08 | 住友ベークライト株式会社 | ネガ型感光性樹脂組成物、硬化膜、電子装置およびポリマー |
| JP6306296B2 (ja) | 2013-07-09 | 2018-04-04 | 太陽インキ製造株式会社 | 感光性熱硬化性樹脂組成物およびフレキシブルプリント配線板 |
| WO2015038412A2 (en) * | 2013-09-16 | 2015-03-19 | Promerus, Llc | Amine treated maleic anhydride polymers with pendent silyl group, compositions and applications thereof |
| JP2015184325A (ja) * | 2014-03-20 | 2015-10-22 | 住友ベークライト株式会社 | 感光性樹脂組成物および電子装置 |
| KR20180088652A (ko) * | 2015-11-30 | 2018-08-06 | 프로메러스, 엘엘씨 | 광산발생제 및 염기 함유 영구유전체조성물 |
-
2016
- 2016-02-02 TW TW105103252A patent/TWI652281B/zh active
- 2016-02-12 CN CN201680018462.3A patent/CN107407872B/zh active Active
- 2016-02-12 WO PCT/US2016/017656 patent/WO2016133795A1/en not_active Ceased
- 2016-02-12 KR KR1020177025264A patent/KR101998338B1/ko active Active
- 2016-02-12 US US15/042,240 patent/US9952507B2/en active Active
- 2016-02-12 JP JP2017542905A patent/JP6513208B2/ja active Active
-
2018
- 2018-03-12 US US15/918,604 patent/US10409160B2/en active Active
-
2019
- 2019-07-22 US US16/517,927 patent/US10634998B2/en active Active
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