TW202348638A

TW202348638A - 感光性樹脂組合物、硬化物及圖像顯示裝置

感光性樹脂組合物、硬化物及圖像顯示裝置 Download PDF

Info

Publication number: TW202348638A
Authority: TW; Taiwan
Prior art keywords: ring; group; mass; resin composition; photosensitive resin
Prior art date: 2022-03-24

Application number

TW112109731A

Other languages

English (en)

Chinese (zh)

Inventor

小泉裕貴

三島康太郎

沢井良尚

Original Assignee

日商三菱化學股份有限公司

Priority date

2022-03-24

Filing date

2023-03-16

Publication date

2023-12-16

2023-03-16 Application filed by 日商三菱化學股份有限公司 filed Critical 日商三菱化學股份有限公司

2023-12-16 Publication of TW202348638A publication Critical patent/TW202348638A/zh

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239000011342 resin composition Substances 0.000 title claims abstract description 122
150000001875 compounds Chemical class 0.000 claims abstract description 127
125000003118 aryl group Chemical group 0.000 claims abstract description 80
229920005989 resin Polymers 0.000 claims abstract description 74
239000011347 resin Substances 0.000 claims abstract description 74
239000004593 Epoxy Substances 0.000 claims abstract description 57
239000004925 Acrylic resin Substances 0.000 claims abstract description 45
229910052717 sulfur Inorganic materials 0.000 claims abstract description 43
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 36
239000011593 sulfur Substances 0.000 claims abstract description 36
239000003999 initiator Substances 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims description 68
239000000126 substance Substances 0.000 claims description 62
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
239000007787 solid Substances 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000002947 alkylene group Chemical group 0.000 claims description 14
150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
239000003513 alkali Substances 0.000 abstract description 11
239000010408 film Substances 0.000 description 92
-1 methylene, ethylidene, methylmethylene Chemical group 0.000 description 75
125000001931 aliphatic group Chemical group 0.000 description 68
239000000758 substrate Substances 0.000 description 65
239000003822 epoxy resin Substances 0.000 description 32
229920000647 polyepoxide Polymers 0.000 description 32
239000002904 solvent Substances 0.000 description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 description 31
239000004094 surface-active agent Substances 0.000 description 31
238000011156 evaluation Methods 0.000 description 26
125000000217 alkyl group Chemical group 0.000 description 25
239000011148 porous material Substances 0.000 description 25
238000011161 development Methods 0.000 description 24
125000000753 cycloalkyl group Chemical group 0.000 description 23
239000002253 acid Substances 0.000 description 22
238000000034 method Methods 0.000 description 22
239000000047 product Substances 0.000 description 22
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
239000006185 dispersion Substances 0.000 description 19
239000000463 material Substances 0.000 description 19
239000002245 particle Substances 0.000 description 19
239000011248 coating agent Substances 0.000 description 18
238000000576 coating method Methods 0.000 description 18
239000003086 colorant Substances 0.000 description 18
150000007519 polyprotic acids Polymers 0.000 description 18
230000035945 sensitivity Effects 0.000 description 17
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
150000002430 hydrocarbons Chemical group 0.000 description 15
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239000000049 pigment Substances 0.000 description 15
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
150000004945 aromatic hydrocarbons Chemical group 0.000 description 14
229910052731 fluorine Inorganic materials 0.000 description 14
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 14
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YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
239000011737 fluorine Substances 0.000 description 13
239000011521 glass Substances 0.000 description 13
239000003112 inhibitor Substances 0.000 description 13
239000010410 layer Substances 0.000 description 13
238000006116 polymerization reaction Methods 0.000 description 13
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
230000000052 comparative effect Effects 0.000 description 12
239000000178 monomer Substances 0.000 description 12
125000001624 naphthyl group Chemical group 0.000 description 12
125000004434 sulfur atom Chemical group 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
125000004122 cyclic group Chemical group 0.000 description 11
239000011976 maleic acid Substances 0.000 description 11
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JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 10
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239000002585 base Substances 0.000 description 10
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 10
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UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 10
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125000003545 alkoxy group Chemical group 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
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150000004706 metal oxides Chemical class 0.000 description 9
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 9
238000002156 mixing Methods 0.000 description 9
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
229910000147 aluminium phosphate Inorganic materials 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
150000001735 carboxylic acids Chemical class 0.000 description 8
PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000005842 heteroatom Chemical group 0.000 description 8
239000007788 liquid Substances 0.000 description 8
238000012719 thermal polymerization Methods 0.000 description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
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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 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
239000006087 Silane Coupling Agent Substances 0.000 description 7
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
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125000005843 halogen group Chemical group 0.000 description 7
238000005259 measurement Methods 0.000 description 7
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LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical group C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 6
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125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 6
239000002270 dispersing agent Substances 0.000 description 6
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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229920000642 polymer Polymers 0.000 description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
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238000005227 gel permeation chromatography Methods 0.000 description 5
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QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 5
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239000003505 polymerization initiator Substances 0.000 description 5
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230000001235 sensitizing effect Effects 0.000 description 5
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UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 4
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150000001252 acrylic acid derivatives Chemical class 0.000 description 4
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125000002883 imidazolyl group Chemical group 0.000 description 4
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BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 4
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PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 3
ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 3
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
JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 3
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1