JP6825217B2 - 感放射線樹脂組成物及び電子部品 - Google Patents
感放射線樹脂組成物及び電子部品 Download PDFInfo
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- JP6825217B2 JP6825217B2 JP2016063919A JP2016063919A JP6825217B2 JP 6825217 B2 JP6825217 B2 JP 6825217B2 JP 2016063919 A JP2016063919 A JP 2016063919A JP 2016063919 A JP2016063919 A JP 2016063919A JP 6825217 B2 JP6825217 B2 JP 6825217B2
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- VMXAIJCDNKFKPO-UHFFFAOYSA-N n-ethynylaniline Chemical compound C#CNC1=CC=CC=C1 VMXAIJCDNKFKPO-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- WNBDFALPKHFDJO-UHFFFAOYSA-N pentadec-3-ene Chemical compound CCCCCCCCCCCC=CCC WNBDFALPKHFDJO-UHFFFAOYSA-N 0.000 description 1
- OHVKVVAUWQFKQY-UHFFFAOYSA-N pentadeca-2,7,9,11-tetraene Chemical compound CCCC=CC=CC=CCCCC=CC OHVKVVAUWQFKQY-UHFFFAOYSA-N 0.000 description 1
- LTBKJTHWKYUMTA-UHFFFAOYSA-N pentadeca-3,10-diene Chemical compound CCCCC=CCCCCCC=CCC LTBKJTHWKYUMTA-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- YGEZYTLOABCHSH-UHFFFAOYSA-N propyl 5-methylbicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCC)(C)CC1C=C2 YGEZYTLOABCHSH-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- LKKVMVMKNLULSL-UHFFFAOYSA-N propyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCC)CC1C=C2 LKKVMVMKNLULSL-UHFFFAOYSA-N 0.000 description 1
- QMTZQLNTTKDRKC-UHFFFAOYSA-N propyl tricyclo[5.2.1.02,6]dec-8-ene-2-carboxylate Chemical compound C(CC)OC(=O)C12C3C=CC(C2CCC1)C3 QMTZQLNTTKDRKC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003156 secondary amide group Chemical group 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- PVJHFVMRMWVWAX-UHFFFAOYSA-N tetradeca-2,7,9,11-tetraene Chemical compound CCC=CC=CC=CCCCC=CC PVJHFVMRMWVWAX-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- ZQJYXISBATZORI-UHFFFAOYSA-N tributyl(ethoxy)silane Chemical compound CCCC[Si](CCCC)(CCCC)OCC ZQJYXISBATZORI-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- YOKZJDRCZXTECO-UHFFFAOYSA-N tricyclo[5.2.1.02,6]deca-3,8-diene-2-carboxylic acid Chemical compound C1=CC2CC1C1(C(=O)O)C2CC=C1 YOKZJDRCZXTECO-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 1
- VNTPGSZQKARKHG-UHFFFAOYSA-N trimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C[Si](C)(C)CCCOCC1CO1 VNTPGSZQKARKHG-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Landscapes
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
Description
〔1〕重量平均分子量が3,000〜50,000であるバインダー樹脂(A)、感放射線化合物(B)、軟化点が30℃以下であり、かつ、4官能以下であるエポキシ系架橋剤(C)、及びトリアジン骨格含有クレゾールノボラック樹脂(D)を含有する感放射線樹脂組成物、
〔2〕前記バインダー樹脂(A)が、プロトン性極性基を有する重合体である前記〔1〕に記載の感放射線樹脂組成物、
〔3〕前記バインダー樹脂(A)が、カルボキシル基を含有する環状オレフィン重合体である前記〔1〕に記載の感放射線樹脂組成物、
〔4〕前記トリアジン骨格含有クレゾールノボラック樹脂(D)の重量平均分子量が3,000未満である前記〔1〕〜〔3〕のいずれかに記載の感放射線樹脂組成物、
〔5〕前記トリアジン骨格含有クレゾールノボラック樹脂(D)の含有量が、前記バインダー樹脂(A)100重量部に対して、1〜100重量部である前記〔1〕〜〔4〕のいずれかに記載の感放射線樹脂組成物、ならびに、
〔6〕前記〔1〕〜〔5〕のいずれかに記載の樹脂組成物からなる樹脂膜を備える電子部品、
が提供される。
本発明で用いるバインダー樹脂(A)としては、重量平均分子量(Mw)が3,000〜50,000の範囲にあるものであればよく、特に限定されないが、プロトン性極性基を有する重合体が好ましく、プロトン性極性基を有する環状オレフィン重合体(A1)、アクリル樹脂(A2)、ポリイミド(A3)、カルド樹脂(A4)又はポリシロキサン(A5)であることがより好ましく、これらの中でも、プロトン性極性基を有する環状オレフィン重合体(A1)が特に好ましい。
これらのバインダー樹脂(A)は、それぞれ単独で用いてもよく、又は2種以上を併用してもよい。
本発明において、プロトン性極性基を有する環状オレフィン樹脂に結合しているプロトン性極性基の数に特に限定はなく、また、相異なる種類のプロトン性極性基が含まれていてもよい。
これら単量体(b2)は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
これら単量体(b3)は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
プロトン性極性基を有しない重合体は、上述した単量体(b1)及び(b2)のうち少なくとも一種と、必要に応じて単量体(b3)とを任意に組み合わせて重合することによって得ることができる。
このような化合物の具体例としては、アクリル酸、メタクリル酸、アンゲリカ酸、チグリン酸、オレイン酸、エライジン酸、エルカ酸、ブラシジン酸、マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、アトロパ酸、ケイ皮酸等の不飽和カルボン酸;アリルアルコール、メチルビニルメタノール、クロチルアルコール、メタリルアルコール、1−フェニルエテン−1−オール、2−プロペン−1−オール、3−ブテン−1−オール、3−ブテン−2−オール、3−メチル−3−ブテン−1−オール、3−メチル−2−ブテン−1−オール、2−メチル−3−ブテン−2−オール、2−メチル−3−ブテン−1−オール、4−ペンテン−1−オール、4−メチル−4−ぺンテン−1−オール、2−ヘキセン−1−オール等の不飽和アルコール;等が挙げられる。
これら変性剤を用いた重合体の変性反応は、常法に従えばよく、通常、ラジカル発生剤の存在下で行われる。
アクリル基を有するカルボン酸無水物の具体例としては、無水マレイン酸、シトラコン酸無水物等が挙げられる。
エポキシ基含有アクリレート化合物の具体例としては、アクリル酸グリシジル、メタクリル酸グリシジル、α−エチルアクリル酸グリシジル、α−n−プロピルアクリル酸グリシジル、α−n−ブチルアクリル酸グリシジル、アクリル酸−3,4−エポキシブチル、メタクリル酸−3,4−エポキシブチル、アクリル酸−6,7−エポキシヘプチル、メタクリル酸−6,7−エポキシヘプチル、α−エチルアクリル酸−6,7−エポキシヘプチル、アクリル酸−3,4−エポキシシクロヘキシルメチル、メタクリル酸−3,4−エポキシシクロヘキシルメチル等が挙げられる。
オキセタン基含有アクリレート化合物の具体例としては、(メタ)アクリル酸(3−メチルオキセタン−3−イル)メチル、(メタ)アクリル酸(3−エチルオキセタン−3−イル)メチル、(メタ)アクリル酸(3−メチルオキセタン−3−イル)エチル、(メタ)アクリル酸(3−エチルオキセタン−3−イル)エチル、(メタ)アクリル酸(3−クロロメチルオキセタン−3−イル)メチル、(メタ)アクリル酸(オキセタン−2−イル)メチル、(メタ)アクリル酸(2−メチルオキセタン−2−イル)メチル、(メタ)アクリル酸(2−エチルオキセタン−2−イル)メチル、(1−メチル−1−オキセタニル−2−フェニル)−3−(メタ)アクリレート、(1−メチル−1−オキセタニル)−2−トリフロロメチル−3−(メタ)アクリレート、及び(1−メチル−1−オキセタニル)−4−トリフロロメチル−2−(メタ)アクリレート等が挙げられる。
これらのうち、(メタ)アクリル酸、無水マレイン酸、(メタ)アクリル酸グリシジル、メタクリル酸−6,7−エポキシヘプチル等が好ましい。
これらのなかでも、メチル(メタ)アクリレート、ブチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−メチルシクロヘキシル(メタ)アクリレート、ベンジル(メタ)アクリレート、トリシクロ[5.2.1.0 2 , 6 ]デカン−8−イル(メタ)アクリレート、N−フェニルマレイミド及びN−シクロヘキシルマレイミド等が好ましい。
これらの化合物は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
上記単量体の重合方法は、常法に従えばよく、例えば、懸濁重合法,乳化重合法,溶液重合法等が採用される。
環状構造を構成している4級炭素原子に二つの環状構造が結合した骨格構造の具体例としては、フルオレン骨格、ビスフェノールフルオレン骨格、ビスアミノフェニルフルオレン骨格、エポキシ基を有するフルオレン骨格、アクリル基を有するフルオレン骨格等が挙げられる。
本発明で用いるカルド樹脂(A4)は、このカルド構造を有する骨格がそれに結合している官能基間の反応等により重合して形成される。カルド樹脂(A4)は、主鎖と嵩高い側鎖が一つの元素で繋がれた構造(カルド構造)をもち、主鎖に対してほぼ垂直方向に環状構造を有している。
カルド樹脂(A4)は、カルド構造を有する単量体を重合して得られる重合体であるが、その他の共重合可能な単量体との共重合体であってもよい。
上記単量体の重合方法は、常法に従えばよく、例えば、開環重合法や付加重合法等が採用される。
(R4)p−Si−(OR5)4−p (4)
これらのオルガノシランのうち、得られる樹脂膜の耐クラック性や硬度の点から3官能性シランが好ましく用いられる。これらのオルガノシランは単独で使用しても、2種以上を組み合わせて使用してもよい。
バインダー樹脂(A)の重量平均分子量(Mw)や分子量分布(Mw/Mn)は、テトラヒドロフランを溶離液としたゲル・パーミエーション・クロマトグラフィー(GPC)により、ポリスチレン換算値として求められる値である。
感放射線化合物(B)は、紫外線や電子線等の放射線の照射により、化学反応を引き起こすことのできる化合物である。本発明において感放射線化合物(B)は、感放射線樹脂組成物から形成されてなる樹脂膜のアルカリ溶解性を制御できるものが好ましく、特に、光酸発生剤を使用することが好ましい。
これらの感放射線化合物は、それぞれ単独で、又は2種以上を組み合わせて用いることができる。
本発明の感放射線樹脂組成物は、上述したバインダー樹脂(A)及び感放射線化合物(B)に加えて、軟化点が30℃以下であり、かつ、4官能以下であるエポキシ系架橋剤(C)を含有する。
また、本発明の感放射線樹脂組成物は、上述したバインダー樹脂(A)、感放射線化合物(B)、及びエポキシ系架橋剤(C)に加えて、トリアジン骨格含有クレゾールノボラック樹脂(D)を含有する。上述したように、本発明においては、エポキシ系架橋剤(C)とともに、トリアジン骨格含有クレゾールノボラック樹脂(D)を配合することで、本発明の感放射線樹脂組成物を保存安定性に優れたものとすることができ、さらには、樹脂膜とした場合に、得られる樹脂膜を、金属層に対する密着性が高く、現像性に優れたものとすることができる。特に、本発明においては、トリアジン骨格含有クレゾールノボラック樹脂(D)を用いることにより、トリアジン骨格の作用により、金属層に対する密着性を高めることができ、しかも、フェノールよりもpKaの低いクレゾール構造の作用により、感放射線樹脂組成物中における反応性を適切なものとすることができ、これにより、樹脂組成物としての保存安定性、及び樹脂膜とした場合の現像性を良好なものとすることができるものである。
また、本発明の感放射線樹脂組成物には、さらに、溶剤が含有されていてもよい。溶剤としては、特に限定されず、樹脂組成物の溶剤として公知のもの、例えばアセトン、メチルエチルケトン、シクロペンタノン、2−ヘキサノン、3−ヘキサノン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、2−オクタノン、3−オクタノン、4−オクタノンなどの直鎖のケトン類;n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、シクロヘキサノールなどのアルコール類;エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジオキサンなどのエーテル類;エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテルなどのアルコールエーテル類;ギ酸プロピル、ギ酸ブチル、酢酸プロピル、酢酸ブチル、プロピオン酸メチル、プロピオン酸エチル、酪酸メチル、酪酸エチル、乳酸メチル、乳酸エチルなどのエステル類;セロソルブアセテート、メチルセロソルブアセテート、エチルセロソルブアセテート、プロピルセロソルブアセテート、ブチルセロソルブアセテートなどのセロソルブエステル類;プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテルなどのプロピレングリコール類;ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールメチルエチルエーテルなどのジエチレングリコール類;γ−ブチロラクトン、γ−バレロラクトン、γ−カプロラクトン、γ−カプリロラクトンなどの飽和γ−ラクトン類;トリクロロエチレンなどのハロゲン化炭化水素類;トルエン、キシレンなどの芳香族炭化水素類;ジメチルアセトアミド、ジメチルホルムアミド、N−メチルアセトアミドなどの極性溶媒などが挙げられる。これらの溶剤は、単独でも2種以上を組み合わせて用いてもよい。溶剤の含有量は、バインダー樹脂(A)100重量部に対して、好ましくは10〜10000重量部、より好ましくは50〜5000重量部、さらに好ましくは100〜1000重量部の範囲である。なお、感放射線樹脂組成物に溶剤を含有させる場合には、溶剤は、通常、硬化膜形成後に除去されることとなる。
混合の方法は特に限定されないが、感放射線樹脂組成物を構成する各成分を溶剤に溶解又は分散して得られる溶液又は分散液を混合するのが好ましい。これにより、感放射線樹脂組成物は、溶液又は分散液の形態で得られる。
次いで、本発明の電子部品について、説明する。本発明の電子部品は、上述した本発明の感放射線樹脂組成物からなる樹脂膜を有する。
潜像パターンを有する樹脂膜に現像液を接触させる方法としては、例えば、パドル法、スプレー法、ディッピング法等の方法が用いられる。現像は、通常、0〜100℃、好ましくは5〜55℃、より好ましくは10〜30℃の範囲で、通常、30〜180秒間の範囲で適宜選択される。
さらに、必要に応じて、感放射線樹脂組成物に含有させた感放射線化合物(B)を失活させるために、電子部品全面に、活性放射線を照射することもできる。活性放射線の照射には、上記潜像パターンの形成に例示した方法を利用できる。照射と同時に、又は照射後に樹脂膜を加熱してもよい。加熱方法としては、例えば、電子部品をホットプレートやオーブン内で加熱する方法が挙げられる。温度は、通常、80〜300℃、好ましくは100〜200℃の範囲である。
このようにして、パターン化された樹脂膜を備える電子部品は製造することができる。
なお、各特性の定義及び評価方法は、以下のとおりである。
各実施例及び各比較例において作製した感放射線樹脂組成物を25℃の恒温槽で1週間保存し、保存前後の感放射線樹脂組成物の粘度を測定し、保存前後における粘度の増加率を算出し、以下の基準にて評価した。保存前後における粘度の増加率が低いほど、保存安定性に優れていると評価できる。
○:保存前後における粘度の増加率が10%未満
△:保存前後における粘度の増加率が10%以上、30%未満
×:保存前後における粘度の増加率が30%以上
スパッタリング装置を用いて、50nm厚のチタン膜上に、銅を100nmの膜厚で形成したシリコンウエハ上に、各実施例及び各比較例において作製した感放射線樹脂組成物をスピンコートした後、ホットプレートを用いて135℃で2分間加熱乾燥して、樹脂膜を形成した。次いで、窒素中において230℃で1時間加熱することにより、3μm厚の樹脂膜が形成された樹脂膜付きシリコンウエハを得た。そして、得られた樹脂膜付きシリコンウエハを用いて、以下に説明する表面−界面切削法(SAICAS法)により、形成された樹脂膜の、銅に対する密着性の評価を行った。
◎:剥離強度Pが130N/m以上
○:剥離強度Pが100N/m以上、130N/m未満
△:剥離強度Pが70N/m以上、100N/m未満
×:剥離強度Pが70N/m未満
シリコンウエハ上に、各実施例及び各比較例において作製した感放射線樹脂組成物をスピンコートした後、ホットプレートを用いて135℃で2分間加熱乾燥して、厚さ3μmの樹脂膜を形成した。次いで、g線(436nm)、h線(405nm)、及びi線(365nm)の波長の光を発する高圧水銀ランプを用い、400mJ/cm2にて露光を行った。そして、露光後の試料を23℃の2.38%テトラメチルアンモニウムヒドロキシド水溶液(アルカリ現像液)にて3分間浸漬した後、超純水で30秒間リンスを行い、現像後の試料の表面状態を目視にて観察し、以下の基準にて現像性の評価を行った。現像残渣が少ないほど、現像性に優れるものと判断することができる。
○:樹脂膜が完全に溶解しており、現像残渣は確認できなかった。
△:ごく微量であるが現像残渣が確認された。
×:現像残渣が顕著に発生していた。
<環状オレフィン重合体(A−1)の調製>
N−フェニル−ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド(NBPI)40モル%、及び4−ヒドロキシカルボニルテトラシクロ[6.2.1.13,6.02,7]ドデカ−9−エン(TCDC)60モル%からなる単量体混合物100部、1,5−ヘキサジエン2.0部、(1,3−ジメシチルイミダゾリン−2−イリデン)(トリシクロヘキシルホスフィン)ベンジリデンルテニウムジクロリド(Org.Lett.,第1巻,953頁,1999年 に記載された方法で合成した)0.02部、及びジエチレングリコールエチルメチルエーテル200部を、窒素置換したガラス製耐圧反応器に仕込み、攪拌しつつ80℃にて4時間反応させて重合反応液を得た。
バインダー樹脂(A)として、合成例1で得られた環状オレフィン重合体(A−1)の重合体溶液291部(環状オレフィン重合体(A−1)として100部)、感放射線化合物(B)として、4,4’−[1−[4−[1−[4−ヒドロキシフェニル]−1−メチルエチル]フェニル]エチリデン]ビスフェノール(1モル)と1,2−ナフトキノンジアジド−5−スルホン酸クロライド(2.5モル)との縮合物)35部、エポキシ系架橋剤(C)として、エポキシ化ブタンテトラカルボン酸テトラキス(3−シクロヘキセニルメチル)修飾ε−カプロラクトン(商品名「エポリードGT401」、ダイセル化学工業社製、脂肪族環状4官能性のエポキシ樹脂、エポキシ当量:220、常温で液状)40部、トリアジン骨格含有クレゾールノボラック樹脂(D)として、トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製、重量平均分子量:830、窒素含有量:18重量%、不揮発分50重量%のプロピレングリコールモノメチルエーテル溶液)30部(トリアジン骨格含有クレゾールノボラック樹脂換算で15部)、及び、溶剤として、ジエチレングリコールエチルメチルエーテル160部を混合し、溶解させた後、孔径0.45μmのポリテトラフルオロエチレン製フィルターでろ過して感放射線樹脂組成物を調製した。
トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製、揮発分50重量%のプロピレングリコールモノメチルエーテル溶液)の配合量を、30部から90部(トリアジン骨格含有クレゾールノボラック樹脂換算で15部から45部)に変更した以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
エポキシ化ブタンテトラカルボン酸テトラキス(3−シクロヘキセニルメチル)修飾ε−カプロラクトン(商品名「エポリードGT401」、ダイセル化学工業社製)40部に代えて、ビスフェノールF型エポキシ化合物(商品名「jER YL983U」、三菱化学社製、2官能のエポキシ化合物、エポキシ当量:170、軟化点:常温で液状)31部を使用するとともに、トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製、不揮発分50重量%のプロピレングリコールモノメチルエーテル溶液)の配合量を、30部から60部(トリアジン骨格含有クレゾールノボラック樹脂換算で15部から30部)に変更した以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製、不揮発分50重量%のプロピレングリコールモノメチルエーテル溶液)の配合量を、30部から6部(トリアジン骨格含有クレゾールノボラック樹脂換算で15部から3部)に変更した以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製、不揮発分50重量%のプロピレングリコールモノメチルエーテル溶液)の配合量を、30部から200部(トリアジン骨格含有クレゾールノボラック樹脂換算で15部から100部)に変更した以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製、不揮発分50重量%のプロピレングリコールモノメチルエーテル溶液)を配合しなかった以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製)15部に代えて、トリアジン骨格含有フェノールノボラック樹脂(商品名「LA7052」、DIC社製、重量平均分子量:1720、窒素含有量:8重量%、不揮発分60重量%メチルエチルケトン溶液)66.7部(トリアジン骨格含有フェノールノボラック樹脂換算で40部)を使用した以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
トリアジン骨格含有クレゾールノボラック樹脂(商品名「LA3018−50P」、DIC社製)15部に代えて、トリアジン骨格含有フェノールノボラック樹脂(商品名「LA7054」、DIC社製、重量平均分子量:1330、窒素含有量:12重量%、不揮発分60重量%メチルエチルケトン溶液)66.7部(トリアジン骨格含有フェノールノボラック樹脂換算で40部)を使用した以外は、実施例1と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
エポキシ化ブタンテトラカルボン酸テトラキス(3−シクロヘキセニルメチル)修飾ε−カプロラクトン(商品名「エポリードGT401」、ダイセル化学工業社製)40部に代えて、グリシジルエーテル型エポキシ化合物(商品名「エピクロンHP7200HH」、DIC社製、多官能のエポキシ化合物、エポキシ当量:280、軟化点:92℃)51部を使用した以外は、比較例3と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
エポキシ化ブタンテトラカルボン酸テトラキス(3−シクロヘキセニルメチル)修飾ε−カプロラクトン(商品名「エポリードGT401」、ダイセル化学工業社製)40部に代えて、グリシジルエーテル型エポキシ化合物(商品名「エピクロンHP7200HH」、DIC社製、多官能のエポキシ化合物、エポキシ当量:280、軟化点:92℃)51部を使用した以外は、実施例2と同様にして、感放射線樹脂組成物を調製し、同様に測定・評価を行った。結果を表1に示す。
また、トリアジン骨格含有クレゾールノボラック樹脂(D)の代わりに、フェノール構造を有する、トリアジン骨格含有フェノールノボラック樹脂を使用した場合には、樹脂組成物としての保存安定性に劣り、また、現像性にも劣るものであった(比較例2,3)。なお、比較例2,3において、このような結果となったのは、トリアジン骨格含有フェノールノボラック樹脂の反応性が高すぎることによると推察される。
さらに、軟化点が30℃以下であり、かつ、4官能以下であるエポキシ系架橋剤(C)の代わりに、軟化点が30℃超であるエポキシ化合物を使用した場合には、得られる樹脂膜は、現像性に劣るものであった(比較例4,5)。
Claims (4)
- 重量平均分子量が3,000〜50,000であるバインダー樹脂(A)、感放射線化合物(B)、軟化点が30℃以下であり、かつ、4官能以下であるエポキシ系架橋剤(C)、及びトリアジン骨格含有クレゾールノボラック樹脂(D)を含有し、
前記バインダー樹脂(A)が、カルボキシル基を含有する環状オレフィン重合体であり、
前記トリアジン骨格含有クレゾールノボラック樹脂(D)の含有量が、前記バインダー樹脂(A)100重量部に対して、5〜80重量部である感放射線樹脂組成物。 - 前記バインダー樹脂(A)が、プロトン性極性基を有する重合体である請求項1に記載の感放射線樹脂組成物。
- 前記トリアジン骨格含有クレゾールノボラック樹脂(D)の重量平均分子量が3,000未満である請求項1または2に記載の感放射線樹脂組成物。
- 請求項1〜3のいずれかに記載の感放射線樹脂組成物からなる樹脂膜を備える電子部品。
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