JP5504824B2

JP5504824B2 - ポジ型感放射線性樹脂組成物、層間絶縁膜及びその形成方法

ポジ型感放射線性樹脂組成物、層間絶縁膜及びその形成方法 Download PDF

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Publication number: JP5504824B2
Authority: JP; Japan
Prior art keywords: resin composition; mass; sensitive resin; compound; interlayer insulating
Prior art date: 2009-10-28
Legal status : Active

Application number

JP2009248332A

Other languages

English (en)

Japanese (ja)

Other versions

JP2011095433A (ja

Inventor

政暁花村

めぐみ村田

雅史荒井

Current Assignee

JSR Corp

Original Assignee

JSR Corp

Priority date

2009-10-28

Filing date

2009-10-28

Publication date

2014-05-28

2009-10-28 Application filed by JSR Corp filed Critical JSR Corp

2009-10-28 Priority to JP2009248332A priority Critical patent/JP5504824B2/ja

2010-10-26 Priority to CN2010105314079A priority patent/CN102053497B/zh

2010-10-28 Priority to TW99136838A priority patent/TW201122728A/zh

2011-05-12 Publication of JP2011095433A publication Critical patent/JP2011095433A/ja

2014-05-28 Application granted granted Critical

2014-05-28 Publication of JP5504824B2 publication Critical patent/JP5504824B2/ja

Status Active legal-status Critical Current

2029-10-28 Anticipated expiration legal-status Critical

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230000005855 radiation Effects 0.000 title claims description 97
239000011229 interlayer Substances 0.000 title claims description 67
239000011342 resin composition Substances 0.000 title claims description 67
238000000034 method Methods 0.000 title claims description 46
150000001875 compounds Chemical class 0.000 claims description 102
229920001577 copolymer Polymers 0.000 claims description 54
238000000576 coating method Methods 0.000 claims description 41
239000011248 coating agent Substances 0.000 claims description 39
239000000758 substrate Substances 0.000 claims description 30
239000011347 resin Substances 0.000 claims description 24
229920005989 resin Polymers 0.000 claims description 24
230000008569 process Effects 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
238000010438 heat treatment Methods 0.000 claims description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
238000009413 insulation Methods 0.000 claims description 12
239000000178 monomer Substances 0.000 claims description 12
150000001412 amines Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
125000003700 epoxy group Chemical group 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 5
230000001678 irradiating effect Effects 0.000 claims description 5
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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238000011161 development Methods 0.000 description 38
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239000007983 Tris buffer Substances 0.000 description 5
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FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 5
239000002516 radical scavenger Substances 0.000 description 5
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YWZLWZLDKOMDSD-UHFFFAOYSA-N 2,5-ditert-butyl-4-prop-1-enylphenol Chemical compound C(C)(C)(C)C1=C(C=C(C(=C1)C=CC)C(C)(C)C)O YWZLWZLDKOMDSD-UHFFFAOYSA-N 0.000 description 4
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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230000001588 bifunctional effect Effects 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 4
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
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238000004519 manufacturing process Methods 0.000 description 4
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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229910019142 PO4 Inorganic materials 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 3
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 3
230000001476 alcoholic effect Effects 0.000 description 3
150000001491 aromatic compounds Chemical class 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
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
230000006872 improvement Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 3
125000000466 oxiranyl group Chemical group 0.000 description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
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239000003505 polymerization initiator Substances 0.000 description 3
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 3
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150000003527 tetrahydropyrans Chemical group 0.000 description 3
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 3
WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 3
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NJMCHQONLVUNAM-UHFFFAOYSA-N (2-nitrophenyl)methyl n-cyclohexylcarbamate Chemical compound [O-][N+](=O)C1=CC=CC=C1COC(=O)NC1CCCCC1 NJMCHQONLVUNAM-UHFFFAOYSA-N 0.000 description 2
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KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
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ZYVXFNCWRJNIQJ-UHFFFAOYSA-M 1-(4,7-dibutoxynaphthalen-1-yl)thiolan-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC(OCCCC)=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 ZYVXFNCWRJNIQJ-UHFFFAOYSA-M 0.000 description 2
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RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-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
HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
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CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 description 2
VTFXHGBOGGGYDO-UHFFFAOYSA-N 2,4-bis(dodecylsulfanylmethyl)-6-methylphenol Chemical compound CCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCC)=C1 VTFXHGBOGGGYDO-UHFFFAOYSA-N 0.000 description 2
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