CN1806206A - 光敏树脂组合物 - Google Patents
光敏树脂组合物 Download PDFInfo
- Publication number
- CN1806206A CN1806206A CNA2004800169298A CN200480016929A CN1806206A CN 1806206 A CN1806206 A CN 1806206A CN A2004800169298 A CNA2004800169298 A CN A2004800169298A CN 200480016929 A CN200480016929 A CN 200480016929A CN 1806206 A CN1806206 A CN 1806206A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- photosensitive resin
- azo
- polymerization initiator
- cyano
- 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
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 85
- -1 naphthoquinonediazide compound Chemical class 0.000 claims abstract description 54
- 229920005989 resin Polymers 0.000 claims abstract description 52
- 239000011347 resin Substances 0.000 claims abstract description 50
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 18
- 239000011229 interlayer Substances 0.000 claims abstract description 14
- 150000002989 phenols Chemical class 0.000 claims abstract description 14
- 239000004065 semiconductor Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000010408 film Substances 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 239000007869 azo polymerization initiator Substances 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 26
- 239000003513 alkali Substances 0.000 claims description 25
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229930192627 Naphthoquinone Natural products 0.000 claims description 7
- 150000002791 naphthoquinones Chemical class 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- 238000000059 patterning Methods 0.000 claims description 3
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- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 abstract 2
- 239000004848 polyfunctional curative Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 24
- 238000005886 esterification reaction Methods 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 230000032050 esterification Effects 0.000 description 16
- 238000011156 evaluation Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
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- 238000010438 heat treatment Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical class C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 5
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001259 photo etching Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- VPSLGSSVPWVZFG-UHFFFAOYSA-N butan-2-yl propanoate Chemical compound CCC(C)OC(=O)CC VPSLGSSVPWVZFG-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
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Classifications
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- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
耐溶剂性评价 | 耐热性评价 | 时间稳定性评价 | |
实施例1 | ○ | ○ | ○ |
实施例2 | ○ | ○ | ○ |
实施例3 | ○ | ○ | ○ |
对比例1 | × | × | ○ |
对比例2 | ○ | ○ | × |
Claims (14)
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JP2003182087A JP4099114B2 (ja) | 2003-06-26 | 2003-06-26 | 感光性樹脂組成物 |
JP182087/2003 | 2003-06-26 |
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CN1806206A true CN1806206A (zh) | 2006-07-19 |
CN100547485C CN100547485C (zh) | 2009-10-07 |
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CNB2004800169298A Expired - Fee Related CN100547485C (zh) | 2003-06-26 | 2004-06-17 | 光敏树脂组合物 |
Country Status (5)
Country | Link |
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JP (1) | JP4099114B2 (zh) |
KR (1) | KR100983210B1 (zh) |
CN (1) | CN100547485C (zh) |
TW (1) | TWI332121B (zh) |
WO (1) | WO2005001575A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102096319A (zh) * | 2009-10-27 | 2011-06-15 | 三星电子株式会社 | 光刻胶组合物和使用其制造显示基板的方法 |
CN105814488A (zh) * | 2013-12-11 | 2016-07-27 | 富士胶片株式会社 | 感光性树脂组合物、固化膜的制造方法、固化膜、液晶显示装置及有机el 显示装置 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5338352B2 (ja) * | 2009-02-09 | 2013-11-13 | 日油株式会社 | ポジ型感光性樹脂組成物 |
KR101930975B1 (ko) * | 2011-06-20 | 2018-12-19 | 닛뽄 가야쿠 가부시키가이샤 | 네거티브형 감광성 수지 조성물 및 그 경화물 |
JP2013130816A (ja) * | 2011-12-22 | 2013-07-04 | Nippon Zeon Co Ltd | 永久膜用樹脂組成物及び電子部品 |
KR20160111805A (ko) * | 2015-03-17 | 2016-09-27 | 동우 화인켐 주식회사 | 감광성 수지 조성물, 이로부터 형성된 광경화 패턴 및 이를 포함하는 화상 표시 장치 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05297582A (ja) * | 1992-04-23 | 1993-11-12 | Fuji Photo Film Co Ltd | ポジ型フオトレジスト組成物 |
JPH08301990A (ja) * | 1995-05-09 | 1996-11-19 | Nippon Kayaku Co Ltd | 樹脂組成物、レジストインキ組成物及びその硬化物 |
JP3901266B2 (ja) * | 1996-11-15 | 2007-04-04 | 東京応化工業株式会社 | 感光性樹脂組成物 |
JP3873263B2 (ja) * | 1997-09-22 | 2007-01-24 | Jsr株式会社 | 感放射線性樹脂組成物、保護膜、層間絶縁膜およびこれらの膜の形成法 |
JP4221819B2 (ja) * | 1999-06-01 | 2009-02-12 | 東レ株式会社 | 感光性樹脂前駆体組成物 |
US6524764B1 (en) * | 1999-06-01 | 2003-02-25 | Toray Industries, Inc. | Positive-type photosensitive polyimide precursor composition |
JP2000347397A (ja) * | 1999-06-04 | 2000-12-15 | Jsr Corp | 感放射線性樹脂組成物およびその層間絶縁膜への使用 |
JP2002116536A (ja) * | 2000-10-06 | 2002-04-19 | Jsr Corp | 感放射線性樹脂組成物、その硬化物および素子。 |
JP2003029407A (ja) * | 2001-05-07 | 2003-01-29 | Sumitomo Bakelite Co Ltd | ポジ型感光性樹脂組成物及び半導体装置 |
JP3848653B2 (ja) | 2001-09-27 | 2006-11-22 | Azエレクトロニックマテリアルズ株式会社 | 感光性樹脂組成物 |
-
2003
- 2003-06-26 JP JP2003182087A patent/JP4099114B2/ja not_active Expired - Fee Related
-
2004
- 2004-06-17 CN CNB2004800169298A patent/CN100547485C/zh not_active Expired - Fee Related
- 2004-06-17 KR KR1020057024971A patent/KR100983210B1/ko not_active IP Right Cessation
- 2004-06-17 WO PCT/JP2004/008531 patent/WO2005001575A1/ja active Application Filing
- 2004-06-25 TW TW093118414A patent/TWI332121B/zh not_active IP Right Cessation
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102096319A (zh) * | 2009-10-27 | 2011-06-15 | 三星电子株式会社 | 光刻胶组合物和使用其制造显示基板的方法 |
CN102096319B (zh) * | 2009-10-27 | 2014-12-17 | 三星显示有限公司 | 光刻胶组合物和使用其制造显示基板的方法 |
CN105814488A (zh) * | 2013-12-11 | 2016-07-27 | 富士胶片株式会社 | 感光性树脂组合物、固化膜的制造方法、固化膜、液晶显示装置及有机el 显示装置 |
CN105814488B (zh) * | 2013-12-11 | 2019-11-05 | 富士胶片株式会社 | 感光性树脂组合物、固化膜的制造方法、固化膜、液晶显示装置及有机el显示装置 |
Also Published As
Publication number | Publication date |
---|---|
TWI332121B (en) | 2010-10-21 |
JP2005017666A (ja) | 2005-01-20 |
WO2005001575A1 (ja) | 2005-01-06 |
TW200504461A (en) | 2005-02-01 |
KR20060027817A (ko) | 2006-03-28 |
JP4099114B2 (ja) | 2008-06-11 |
KR100983210B1 (ko) | 2010-09-20 |
CN100547485C (zh) | 2009-10-07 |
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