TWI793289B - 含有聚合性不飽和基的鹼可溶性樹脂的製造方法、含有聚合性不飽和基的鹼可溶性樹脂、以其作為必須成分的感光性樹脂組成物以及其硬化膜 - Google Patents

含有聚合性不飽和基的鹼可溶性樹脂的製造方法、含有聚合性不飽和基的鹼可溶性樹脂、以其作為必須成分的感光性樹脂組成物以及其硬化膜 Download PDF

Info

Publication number: TWI793289B
Authority: TW; Taiwan
Prior art keywords: acid; alkali; polymerizable unsaturated; general formula; soluble resin
Prior art date: 2018-03-28

Application number

TW108110742A

Other languages

English (en)

Chinese (zh)

Other versions

TW201942185A (zh

Inventor

滑川崇平

高野正臣

Original Assignee

日商日鐵化學材料股份有限公司

Priority date (The priority date 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 date listed.)

2018-03-28

Filing date

2019-03-27

Publication date

2023-02-21

2019-03-27 Application filed by 日商日鐵化學材料股份有限公司 filed Critical 日商日鐵化學材料股份有限公司

2019-11-01 Publication of TW201942185A publication Critical patent/TW201942185A/zh

2023-02-21 Application granted granted Critical

2023-02-21 Publication of TWI793289B publication Critical patent/TWI793289B/zh

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229920005989 resin Polymers 0.000 title claims abstract description 58
239000011347 resin Substances 0.000 title claims abstract description 58
239000011342 resin composition Substances 0.000 title claims description 37
238000000034 method Methods 0.000 title description 21
150000001875 compounds Chemical class 0.000 claims abstract description 46
239000004593 Epoxy Substances 0.000 claims abstract description 38
239000002253 acid Substances 0.000 claims abstract description 37
150000003628 tricarboxylic acids Chemical class 0.000 claims abstract description 17
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 16
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 14
238000004519 manufacturing process Methods 0.000 claims abstract description 14
150000000000 tetracarboxylic acids Chemical class 0.000 claims abstract description 12
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 11
239000007795 chemical reaction product Substances 0.000 claims abstract description 11
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 9
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 6
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
239000002904 solvent Substances 0.000 claims description 21
239000003999 initiator Substances 0.000 claims description 11
239000000178 monomer Substances 0.000 claims description 10
125000003700 epoxy group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000003822 epoxy resin Substances 0.000 claims description 6
229920000647 polyepoxide Polymers 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
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-1 boards Substances 0.000 description 52
239000010408 film Substances 0.000 description 52
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238000006243 chemical reaction Methods 0.000 description 21
239000003513 alkali Substances 0.000 description 17
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239000000243 solution Substances 0.000 description 16
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
239000011248 coating agent Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 10
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
238000011161 development Methods 0.000 description 9
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238000003786 synthesis reaction Methods 0.000 description 8
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239000003054 catalyst Substances 0.000 description 7
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239000011810 insulating material Substances 0.000 description 7
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239000007864 aqueous solution Substances 0.000 description 5
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 5
238000006735 epoxidation reaction Methods 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
238000000016 photochemical curing Methods 0.000 description 5
230000035945 sensitivity Effects 0.000 description 5
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HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 5
KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 4
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000013329 compounding Methods 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
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229930195733 hydrocarbon Natural products 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
238000000059 patterning Methods 0.000 description 4
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ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
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JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
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QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
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HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G

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Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
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Organic Chemistry (AREA)
Materials For Photolithography (AREA)
Epoxy Resins (AREA)
Macromonomer-Based Addition Polymer (AREA)

TW108110742A 2018-03-28 2019-03-27 含有聚合性不飽和基的鹼可溶性樹脂的製造方法、含有聚合性不飽和基的鹼可溶性樹脂、以其作為必須成分的感光性樹脂組成物以及其硬化膜 TWI793289B (zh)

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TW201612634A (en) *	2014-09-30	2016-04-01	Nippon Steel & Sumikin Chem Co	Photosensitive resin composition for touch panel, cured film using the same, and touch panel including such cured film as a component

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JP2018154738A (ja)	2017-03-17	2018-10-04	株式会社タムラ製作所	感光性樹脂及び感光性樹脂組成物

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TW200911865A (en) *	2007-03-28	2009-03-16	Toto Kasei Kk	Novel epoxy resin, epoxy resin composition containing the same, and cured matter therefrom
TW201612634A (en) *	2014-09-30	2016-04-01	Nippon Steel & Sumikin Chem Co	Photosensitive resin composition for touch panel, cured film using the same, and touch panel including such cured film as a component

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