KR20170117103A - 광염기 발생제를 함유하는 광이미지화 가능한 조성물 - Google Patents
광염기 발생제를 함유하는 광이미지화 가능한 조성물 Download PDFInfo
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- KR20170117103A KR20170117103A KR1020177024736A KR20177024736A KR20170117103A KR 20170117103 A KR20170117103 A KR 20170117103A KR 1020177024736 A KR1020177024736 A KR 1020177024736A KR 20177024736 A KR20177024736 A KR 20177024736A KR 20170117103 A KR20170117103 A KR 20170117103A
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- South Korea
- Prior art keywords
- hept
- ene
- bicyclo
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- 239000000203 mixture Substances 0.000 title claims abstract description 77
- 229920000642 polymer Polymers 0.000 claims abstract description 69
- 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 29
- 239000000178 monomer Substances 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 22
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- UDOJACSDSIHAAT-UHFFFAOYSA-N 5-benzylbicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CC1=CC=CC=C1 UDOJACSDSIHAAT-UHFFFAOYSA-N 0.000 claims description 10
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003504 photosensitizing agent Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 5
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims description 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 239000002318 adhesion promoter Substances 0.000 claims description 5
- KELKBCPSSMHFNT-UHFFFAOYSA-N 1-(1-phenylethyl)-3,4,6,7,8,8a-hexahydro-2H-pyrrolo[1,2-a]pyrimidine Chemical compound C1(=CC=CC=C1)C(C)N1C2N(CCC1)CCC2 KELKBCPSSMHFNT-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- HYQWHUCTTYCIAU-UHFFFAOYSA-N 1-benzyl-3,4,6,7,8,8a-hexahydro-2h-pyrrolo[1,2-a]pyrimidine Chemical compound C1CCN2CCCC2N1CC1=CC=CC=C1 HYQWHUCTTYCIAU-UHFFFAOYSA-N 0.000 claims description 3
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 claims description 3
- GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 claims description 3
- PZHUETTVRMNXHJ-UHFFFAOYSA-N 1-(1-phenylpropyl)-3,4,6,7,8,8a-hexahydro-2H-pyrrolo[1,2-a]pyrimidine Chemical compound C1(=CC=CC=C1)C(CC)N1C2N(CCC1)CCC2 PZHUETTVRMNXHJ-UHFFFAOYSA-N 0.000 claims description 2
- OKLGIAVJZXLGPC-UHFFFAOYSA-N 1-[1-(2-methylphenyl)ethyl]-3,4,6,7,8,8a-hexahydro-2H-pyrrolo[1,2-a]pyrimidine Chemical compound C1(=C(C=CC=C1)C(C)N1C2N(CCC1)CCC2)C OKLGIAVJZXLGPC-UHFFFAOYSA-N 0.000 claims description 2
- PHZLMBVFCJEBDN-UHFFFAOYSA-N 1-[1-(4-methylphenyl)ethyl]-3,4,6,7,8,8a-hexahydro-2H-pyrrolo[1,2-a]pyrimidine Chemical compound C1(=CC=C(C=C1)C(C)N1C2N(CCC1)CCC2)C PHZLMBVFCJEBDN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 claims 1
- 238000004377 microelectronic Methods 0.000 abstract description 9
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- 239000010410 layer Substances 0.000 description 31
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 10
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 9
- 230000005855 radiation Effects 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 235000012431 wafers Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229920001897 terpolymer Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
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- HHBBIOLEJRWIGU-UHFFFAOYSA-N 4-ethoxy-1,1,1,2,2,3,3,4,5,6,6,6-dodecafluoro-5-(trifluoromethyl)hexane Chemical compound CCOC(F)(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F HHBBIOLEJRWIGU-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 101000692872 Homo sapiens Regulator of microtubule dynamics protein 1 Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 102100026432 Regulator of microtubule dynamics protein 1 Human genes 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
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- 238000011161 development Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- KYOZIVFRHLSSKN-UHFFFAOYSA-N 2-[[2-hydroxy-3-[(2-hydroxy-5-methylphenyl)methyl]-5-methylphenyl]methyl]-6-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=C(CC=3C(=C(CC=4C(=CC=C(C)C=4)O)C=C(C)C=3)O)C=C(C)C=2)O)=C1 KYOZIVFRHLSSKN-UHFFFAOYSA-N 0.000 description 2
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- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
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- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical group CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 1
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- STAXVPTUONLACL-UHFFFAOYSA-N 3-(5-bicyclo[2.2.1]hept-2-enyl)propanoic acid Chemical compound C1C2C(CCC(=O)O)CC1C=C2 STAXVPTUONLACL-UHFFFAOYSA-N 0.000 description 1
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562117769P | 2015-02-18 | 2015-02-18 | |
| US62/117,769 | 2015-02-18 | ||
| PCT/US2016/017654 WO2016133794A1 (en) | 2015-02-18 | 2016-02-12 | Photoimageable compositions containing photobase generators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20170117103A true KR20170117103A (ko) | 2017-10-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177024736A Withdrawn KR20170117103A (ko) | 2015-02-18 | 2016-02-12 | 광염기 발생제를 함유하는 광이미지화 가능한 조성물 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9823565B2 (https=) |
| JP (1) | JP6442618B2 (https=) |
| KR (1) | KR20170117103A (https=) |
| TW (1) | TWI649620B (https=) |
| WO (1) | WO2016133794A1 (https=) |
Families Citing this family (2)
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| TWI649620B (zh) * | 2015-02-18 | 2019-02-01 | 日商住友電木股份有限公司 | 含有光產鹼劑的光可成像組成物 |
| CN111788246B (zh) * | 2018-03-16 | 2022-06-10 | 3M创新有限公司 | 组合物、粘结方法和粘结组件 |
Family Cites Families (11)
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| US6849377B2 (en) * | 1998-09-23 | 2005-02-01 | E. I. Du Pont De Nemours And Company | Photoresists, polymers and 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 |
| US20060020068A1 (en) * | 2004-07-07 | 2006-01-26 | Edmund Elce | Photosensitive compositions based on polycyclic polymers for low stress, high temperature films |
| US8030425B2 (en) | 2002-07-03 | 2011-10-04 | Promerus Llc | Photosensitive compositions based on polycyclic polymers for low stress, high temperature films |
| WO2006008251A2 (en) * | 2004-07-21 | 2006-01-26 | Ciba Specialty Chemicals Holding Inc. | Process for the photoactivation and use of a catalyst by an inverted two-stage procedure |
| JP5521999B2 (ja) * | 2009-11-26 | 2014-06-18 | 住友化学株式会社 | 化学増幅型フォトレジスト組成物及びレジストパターンの製造方法 |
| JPWO2012053052A1 (ja) * | 2010-10-19 | 2014-02-24 | 住友ベークライト株式会社 | 感光性樹脂組成物および半導体装置 |
| CN104221176B (zh) * | 2012-01-16 | 2017-03-01 | 住友电木株式会社 | 用于微电子和光电子器件及其组件的热氧化稳定的、侧链聚醚官能化的聚降冰片烯 |
| KR101572049B1 (ko) * | 2012-09-25 | 2015-11-26 | 프로메러스, 엘엘씨 | 사이클로올레핀성 중합체를 함유하는 말레이미드 및 그의 용도 |
| TWI649620B (zh) * | 2015-02-18 | 2019-02-01 | 日商住友電木股份有限公司 | 含有光產鹼劑的光可成像組成物 |
-
2016
- 2016-02-02 TW TW105103253A patent/TWI649620B/zh not_active IP Right Cessation
- 2016-02-12 KR KR1020177024736A patent/KR20170117103A/ko not_active Withdrawn
- 2016-02-12 JP JP2017542867A patent/JP6442618B2/ja active Active
- 2016-02-12 WO PCT/US2016/017654 patent/WO2016133794A1/en not_active Ceased
- 2016-02-12 US US15/042,220 patent/US9823565B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016133794A1 (en) | 2016-08-25 |
| US20160238931A1 (en) | 2016-08-18 |
| US9823565B2 (en) | 2017-11-21 |
| TWI649620B (zh) | 2019-02-01 |
| JP2018511819A (ja) | 2018-04-26 |
| TW201636734A (zh) | 2016-10-16 |
| JP6442618B2 (ja) | 2018-12-19 |
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| PA0105 | International application |
Patent event date: 20170901 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination |