JP7431050B2

JP7431050B2 - 樹脂組成物、硬化膜、積層体、硬化膜の製造方法、及び、半導体デバイス

樹脂組成物、硬化膜、積層体、硬化膜の製造方法、及び、半導体デバイス Download PDF

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Publication number: JP7431050B2
Authority: JP; Japan
Prior art keywords: group; resin composition; film; surfactant; acid
Prior art date: 2020-02-05
Legal status : Active

Application number

JP2020017972A

Other languages

English (en)

Japanese (ja)

Other versions

JP2021123652A (ja

Inventor

雄一郎榎本

健太山▲ざき▼

Current Assignee

Fujifilm Corp

Original Assignee

Fujifilm Corp

Priority date

2020-02-05

Filing date

2020-02-05

Publication date

2024-02-14

2020-02-05 Application filed by Fujifilm Corp filed Critical Fujifilm Corp

2020-02-05 Priority to JP2020017972A priority Critical patent/JP7431050B2/ja

2021-01-21 Priority to TW110102234A priority patent/TW202130707A/zh

2021-08-30 Publication of JP2021123652A publication Critical patent/JP2021123652A/ja

2024-02-14 Application granted granted Critical

2024-02-14 Publication of JP7431050B2 publication Critical patent/JP7431050B2/ja

Status Active legal-status Critical Current

2040-02-05 Anticipated expiration legal-status Critical

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239000011342 resin composition Substances 0.000 title claims description 207
238000004519 manufacturing process Methods 0.000 title claims description 48
239000004065 semiconductor Substances 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 claims description 228
239000010410 layer Substances 0.000 claims description 142
229920001721 polyimide Polymers 0.000 claims description 135
239000004642 Polyimide Substances 0.000 claims description 134
229920005989 resin Polymers 0.000 claims description 116
239000011347 resin Substances 0.000 claims description 116
239000000203 mixture Substances 0.000 claims description 106
239000004094 surface-active agent Substances 0.000 claims description 96
239000002243 precursor Substances 0.000 claims description 89
238000000034 method Methods 0.000 claims description 85
238000010438 heat treatment Methods 0.000 claims description 70
229910052751 metal Inorganic materials 0.000 claims description 59
239000002184 metal Substances 0.000 claims description 58
229920002577 polybenzoxazole Polymers 0.000 claims description 46
239000002904 solvent Substances 0.000 claims description 44
238000011161 development Methods 0.000 claims description 31
230000008569 process Effects 0.000 claims description 28
229910052731 fluorine Inorganic materials 0.000 claims description 27
125000001153 fluoro group Chemical group F* 0.000 claims description 27
239000003960 organic solvent Substances 0.000 claims description 26
239000000758 substrate Substances 0.000 claims description 25
239000011229 interlayer Substances 0.000 claims description 12
239000007870 radical polymerization initiator Substances 0.000 claims description 11
239000002736 nonionic surfactant Substances 0.000 claims description 9
150000002596 lactones Chemical class 0.000 claims description 6
239000010408 film Substances 0.000 description 210
125000004432 carbon atom Chemical group C* 0.000 description 173
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239000003431 cross linking reagent Substances 0.000 description 73
125000000217 alkyl group Chemical group 0.000 description 60
125000003118 aryl group Chemical group 0.000 description 60
239000002253 acid Substances 0.000 description 59
125000000962 organic group Chemical group 0.000 description 58
150000003254 radicals Chemical class 0.000 description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 description 43
125000001931 aliphatic group Chemical group 0.000 description 38
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 37
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150000003839 salts Chemical class 0.000 description 35
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239000007787 solid Substances 0.000 description 29
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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 description 27
238000006243 chemical reaction Methods 0.000 description 26
230000000052 comparative effect Effects 0.000 description 25
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125000001424 substituent group Chemical group 0.000 description 23
ORMSTDJYMPIZAO-UHFFFAOYSA-N 1,1,2-trichloro-2-fluoroethane Chemical compound FC(Cl)C(Cl)Cl ORMSTDJYMPIZAO-UHFFFAOYSA-N 0.000 description 22
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239000003795 chemical substances by application Substances 0.000 description 21
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239000003505 polymerization initiator Substances 0.000 description 19
239000000126 substance Substances 0.000 description 19
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238000003786 synthesis reaction Methods 0.000 description 16
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238000000576 coating method Methods 0.000 description 15
125000000753 cycloalkyl group Chemical group 0.000 description 15
238000006116 polymerization reaction Methods 0.000 description 15
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 15
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238000001914 filtration Methods 0.000 description 14
125000004430 oxygen atom Chemical group O* 0.000 description 14
239000000243 solution Substances 0.000 description 14
238000001723 curing Methods 0.000 description 13
238000005755 formation reaction Methods 0.000 description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
239000011248 coating agent Substances 0.000 description 12
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
238000003475 lamination Methods 0.000 description 11
NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical class OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 10
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
125000005370 alkoxysilyl group Chemical group 0.000 description 10
125000003710 aryl alkyl group Chemical group 0.000 description 10
239000004202 carbamide Substances 0.000 description 10
238000004132 cross linking Methods 0.000 description 10
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 10
230000007547 defect Effects 0.000 description 10
238000001035 drying Methods 0.000 description 10
238000011156 evaluation Methods 0.000 description 10
230000005012 migration Effects 0.000 description 10
238000013508 migration Methods 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
125000000565 sulfonamide group Chemical group 0.000 description 10
125000006158 tetracarboxylic acid group Chemical group 0.000 description 10
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
239000004593 Epoxy Substances 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
125000004849 alkoxymethyl group Chemical group 0.000 description 9
125000005529 alkyleneoxy group Chemical group 0.000 description 9
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
125000003342 alkenyl group Chemical group 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
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125000004122 cyclic group Chemical group 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
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125000005843 halogen group Chemical group 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
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YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 8
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230000035945 sensitivity Effects 0.000 description 8
238000004528 spin coating Methods 0.000 description 8
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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 7
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JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
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OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
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239000012535 impurity Substances 0.000 description 5
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230000009471 action Effects 0.000 description 4
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125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 4
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