JPWO2017169914A1 - 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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- JPWO2017169914A1 JPWO2017169914A1 JP2018509057A JP2018509057A JPWO2017169914A1 JP WO2017169914 A1 JPWO2017169914 A1 JP WO2017169914A1 JP 2018509057 A JP2018509057 A JP 2018509057A JP 2018509057 A JP2018509057 A JP 2018509057A JP WO2017169914 A1 JPWO2017169914 A1 JP WO2017169914A1
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- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- VJKBQUJCCYLNCM-UHFFFAOYSA-N n-octyl-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(C(CC)CCCC)C1=O VJKBQUJCCYLNCM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- 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
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-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
- 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
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 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
- 238000012545 processing Methods 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003156 secondary amide group Chemical group 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- WUNGPAHZQWNPEL-UHFFFAOYSA-N st50032131 Chemical compound C1=CC2CC1C1C2C(=O)N(CCO)C1=O WUNGPAHZQWNPEL-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- GAONUEUNHBLHPP-UHFFFAOYSA-N stk246934 Chemical compound O=C1C2C(C=C3)CC3C2C(=O)N1C1=CC=CC=C1 GAONUEUNHBLHPP-UHFFFAOYSA-N 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
- 150000003512 tertiary amines Chemical class 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 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
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/508—Amines heterocyclic containing only nitrogen as a heteroatom having three nitrogen atoms in the ring
- C08G59/5086—Triazines; Melamines; Guanamines
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G—PHYSICS
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- G—PHYSICS
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- General Physics & Mathematics (AREA)
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
Abstract
Description
〔1〕プロトン性極性基を有する環状オレフィン重合体(A)、下記一般式(1)で表される2官能のエポキシ化合物(B)、及び感放射線化合物(C)を含有する感放射線樹脂組成物、
〔2〕前記エポキシ化合物(B)の含有量が、前記プロトン性極性基を有する環状オレフィン重合体(A)100重量部に対して、8〜150重量部である前記〔1〕に記載の感放射線樹脂組成物、
〔3〕前記エポキシ化合物(B)のエポキシ当量が100〜1000である前記〔1〕又は〔2〕に記載の感放射線樹脂組成物、
〔4〕前記エポキシ化合物(B)の軟化点が40℃以下である前記〔1〕〜〔3〕のいずれかに記載の感放射線樹脂組成物、
〔5〕分子内にアルコキシメチル基またはメチロール基を2以上含む化合物をさらに含有する前記〔1〕〜〔4〕のいずれかに記載の感放射線樹脂組成物、
〔6〕脂環構造を有するエポキシ化合物をさらに含有する前記〔1〕〜〔5〕のいずれかに記載の感放射線樹脂組成物、
〔7〕シランカップリング剤をさらに含有する前記〔1〕〜〔6〕のいずれかに記載の感放射線樹脂組成物、
〔8〕前記〔1〕〜〔7〕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、
が提供される。
本発明で用いるプロトン性極性基を有する環状オレフィン重合体(A)(以下、単に「環状オレフィン重合体(A)」とする。)としては、1又は2以上の環状オレフィン単量体の重合体、又は、1又は2以上の環状オレフィン単量体と、これと共重合可能な単量体との共重合体が挙げられるが、本発明においては、環状オレフィン重合体(A)を形成するための単量体として、少なくともプロトン性極性基を有する環状オレフィン単量体(a)を用いることが好ましい。
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。
また、環状オレフィン重合体(A)の分子量分布は、重量平均分子量/数平均分子量(Mw/Mn)比で、通常、4以下、好ましくは3以下、より好ましくは2.5以下である。
環状オレフィン重合体(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等の溶媒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。
本発明の感放射線樹脂組成物は、環状オレフィン重合体(A)に加えて、下記一般式(1)で表される2官能のエポキシ化合物(B)(以下、適宜、「2官能直鎖エポキシ化合物(B)」と略記する。)を含有する。
2官能直鎖エポキシ化合物(B)は、本発明の感放射線樹脂組成物において、環状オレフィン重合体(A)の架橋剤として作用するとともに、その直鎖状の構造により、樹脂膜とした場合における弾性率を低下させる効果を奏するものであり、これにより、本発明の感放射線樹脂組成物を用いて得られる樹脂膜の反りの発生を有効に効果的に防止できるものである。
また、本発明の感放射線樹脂組成物は、環状オレフィン重合体(A)及び2官能直鎖エポキシ化合物(B)に加えて、感放射線化合物(C)を含有する。感放射線化合物(C)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。
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。
また、本発明の感放射線樹脂組成物は、上述した2官能直鎖エポキシ化合物(B)以外の架橋剤をさらに含有していてもよい。このような架橋剤としては、加熱により架橋剤分子間に架橋構造を形成するものや、環状オレフィン重合体(A)と反応して樹脂分子間に架橋構造を形成するものであればよいが、例えば、2官能直鎖エポキシ化合物(B)以外のエポキシ基含有架橋剤や、オキセタン基含有架橋剤、イソシアネート基含有架橋剤、ブロックイソシアネート基含有架橋剤、オキサゾリン基含有架橋剤、マレイミド基含有架橋剤、(メタ)アクリレート基含有架橋剤、分子内にアルコキシメチル基またはメチロール基を2以上含む化合物などが挙げられる。これらの中でも、分子内にアルコキシメチル基またはメチロール基を2以上含む化合物が好ましい。2官能直鎖エポキシ化合物(B)以外の架橋剤をさらに含有させることで、得られる樹脂膜の耐熱衝撃性をより高めることができる。
これら、2官能直鎖エポキシ化合物(B)以外のエポキシ基含有架橋剤のなかでも、脂環構造を有するエポキシ化合物、すなわち、脂環式エポキシ化合物が好ましい。脂環構造を有するエポキシ化合物を使用することで、得られる樹脂膜の耐熱衝撃性の向上効果をより顕著なものとすることができる。
分子内に2つ以上のアルコキシメチル基、またはメチロール基を含む化合物は、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。
これらのなかでも、反応性が高いという点より、N,N,N’,N’,N’’,N’’−ヘキサメトキシメチルメラミンが好ましい。
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。
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(C)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を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。
スパッタリング装置を用いて、アルミニウム薄膜が100nmの膜厚で形成され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のち、ホットプレートを用いて120℃で2分間加熱し、次いで、窒素雰囲気下、230℃で60分間の条件で硬化させることで、膜厚10μmの樹脂膜を形成させ、積層体を得た。そして、得られた積層体を、所定の大きさに切断した後、アルミニウム薄膜を0.1mol/Lの塩酸水溶液にて溶解させて剥離させ、剥離したフィルムを乾燥させることで樹脂膜を得た。そして、得られた樹脂膜について、試験片(10mm×50mm)を切り出して、この試験片について以下の手順で引張試験を行うことで、引張弾性率を測定した。すなわち、オートグラフ(株式会社島津製作所製、AGS−5kNG)を用いて、チャック間距離20mm、引張速度10mm/分、測定温度23℃の条件にて引張試験を行うことで、試験片の引張弾性率(GPa)を測定した。なお、両特性ともに、上記各樹脂膜からそれぞれ5つの試験片を切り出し、各試験片について測定した値の平均値を以下の基準で評価した。なお、引張弾性率が低いほど、硬化後の反りの発生が抑制できるため、好ましい。
A:引張弾性率が2GPa未満
B:引張弾性率が2GPa以上、2.2GPa未満
C:引張弾性率が2.2GPa以上
シリコンウエハ上にパターン状の銅配線を有する熱衝撃用の評価基板の上に、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のち、120℃で2分間加熱して、次いで、窒素雰囲気下で230℃で60分間の条件で硬化させることにより、膜厚10μmの樹脂膜を形成することで、評価用サンプルを得た。そして、得られた評価用サンプルについて、熱衝撃試験器(タバイエスペックス社製)を用いて、−55℃/30分及び150℃/30分を1サイクルとして、熱衝撃試験を行い、樹脂膜にクラックが発生するまでのサイクル数を確認し、以下の基準にて、耐熱衝撃性を評価した。
AA:2000サイクル経過後もクラックの発生なし。
A:1500サイクル経過後にはクラックが発生しなかったが、2000サイクル到達前にクラックが発生。
B:1000サイクル経過後にはクラックが発生しなかったが、1500サイクル到達前にクラックが発生。
C:1000サイクル到達前にクラックが発生。
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120℃で2分間プリベークして、厚さ10μm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。樹脂膜の不溶解、あるいは膨潤が発生しないものが、ポジ型の樹脂膜としての現像性に優れると判断でき、しかも、現像時の残渣の発生が有効に抑えられるため、好ましい。
A:樹脂膜が完全に溶解していた。
B:樹脂膜が一部だけ溶解していた。
C:樹脂膜が全く溶解していない、あるいは、膨潤していた。
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の膜厚で形成され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のち、120℃で2分間加熱して、次いで、窒素雰囲気下230℃で60分間の条件で硬化させることにより、膜厚10μmの樹脂膜を形成することで、積層体を得た。このようにして得られた積層体の樹脂膜上に、スパッタリング法により銅箔膜を形成し、次いで、めっき浴として硫酸銅を含んだ酸性水溶液を用いた電気めっきにより、銅めっき層を厚さ10μmにて形成した後、180℃で60分間加熱処理をすることで、試験片を得た。そして、得られた試験片をはんだ温度260℃のハンダ浴に10秒間浮かべ、室温にて30秒間放置した後に、銅めっき層のふくれの有無を確認する試験を、銅めっき層のふくれが確認されるまで繰り返して行い、以下の基準にしたがって、はんだ耐熱性を評価した。銅めっき層のふくれが確認されるまでの試験の繰り返し回数が多いほど、はんだ耐熱性に優れると判断できる。
AA:上記試験を15回繰り返し行ったが、15回目の試験後も、銅めっき層のふくれが確認されなかった。
A:銅めっき層のふくれが確認されるまでの試験の繰り返し回数が、10回以上、14回以下であった。
B:銅めっき層のふくれが確認されるまでの試験の繰り返し回数が、7回以上、9回以下であった。
C:銅めっき層のふくれが確認されるまでの試験の繰り返し回数が、7回未満であった。
<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。
プロトン性極性基を有する環状オレフィン重合体(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)、2官能直鎖エポキシ化合物(B)として、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製、エポキシ当量:440、軟化点25℃以下(常温で液体)、上記一般式(1)において、R1=−C4H8−、k=約10である化合物)10部、感放射線化合物(C)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(2.0モル)との縮合物(商品名「TS200」、東洋合成社製)30部、2官能直鎖エポキシ化合物(B)以外の架橋剤として、N,N,N’,N’,N’’,N’’−ヘキサメトキシメチルメラミン(商品名「ニカラックMW−100LM」、三和ケミカル社製)10部、シランカップリング剤として、γ−グリシドキシプロピルトリメトキシシラン(商品名「Z6040」、東レ・ダウコーニング社製)2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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)の配合量を10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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)の配合量を10部から、50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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)の配合量を10部から、80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。
実施例3において、2官能直鎖エポキシ化合物(B)以外の架橋剤としての、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)20部をさらに配合した以外は、実施例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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)の配合量を10部から、130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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)10部に代えて、ナフタレン骨格を有するエポキシ化合物(商品名「エピクロンHP4700、DIC社製)50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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)10部に代えて、長鎖ビスフェノールA型エポキシ樹脂(商品名「EXA−4850−1000」、DIC社製)50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。
実施例1において、2官能直鎖エポキシ化合物(商品名「jER YX7400」、三菱化学社製)10部に代えて、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)50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。
実施例3において、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)に代えて、アクリル重合体(商品名「マルカリンカーCMM」、丸善石油化学社製、p−ヒドロキシスチレンとメチルメタクリレートとの共重合体)のジエチレングリコールエチルメチルエーテル溶液を、アクリル重合体として100部使用した以外は、実施例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。
また、プロトン性極性基を有する環状オレフィン重合体(A)の代わりに、アクリル重合体を使用した場合には、得られる樹脂膜は、耐熱衝撃性及び現像性に劣るものであった(比較例4)。
Claims (8)
- 前記エポキシ化合物(B)の含有量が、前記プロトン性極性基を有する環状オレフィン重合体(A)100重量部に対して、8〜150重量部である請求項1に記載の感放射線樹脂組成物。
- 前記エポキシ化合物(B)のエポキシ当量が100〜1000である請求項1又は2に記載の感放射線樹脂組成物。
- 前記エポキシ化合物(B)の軟化点が40℃以下である請求項1〜3のいずれかに記載の感放射線樹脂組成物。
- 分子内にアルコキシメチル基またはメチロール基を2以上含む化合物をさらに含有する請求項1〜4のいずれかに記載の感放射線樹脂組成物。
- 脂環構造を有するエポキシ化合物をさらに含有する請求項1〜5のいずれかに記載の感放射線樹脂組成物。
- シランカップリング剤をさらに含有する請求項1〜6のいずれかに記載の感放射線樹脂組成物。
- 請求項1〜7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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WO2012002028A1 (ja) * | 2010-06-28 | 2012-01-05 | 株式会社Adeka | 硬化性樹脂組成物 |
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SG11201501594UA (en) * | 2012-09-25 | 2015-05-28 | Toray Industries | Positive photosensitive resin composition, and method for producing semiconductor device containing a cured film using said composition |
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TW201802593A (zh) | 2018-01-16 |
KR102301534B1 (ko) | 2021-09-10 |
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WO2017169914A1 (ja) | 2017-10-05 |
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