JP2021014577A - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
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- JP2021014577A JP2021014577A JP2020117010A JP2020117010A JP2021014577A JP 2021014577 A JP2021014577 A JP 2021014577A JP 2020117010 A JP2020117010 A JP 2020117010A JP 2020117010 A JP2020117010 A JP 2020117010A JP 2021014577 A JP2021014577 A JP 2021014577A
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy 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])C([H])([H])O* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- PRCNQQRRDGMPKS-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O.CC(=O)CC(C)=O PRCNQQRRDGMPKS-UHFFFAOYSA-N 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N pentane-3,3-diamine Chemical compound CCC(N)(N)CC GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002742 polystyrene-block-poly(ethylene/propylene) -block-polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical group N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical group C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- GHPYAGKTTCKKDF-UHFFFAOYSA-M tetraphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GHPYAGKTTCKKDF-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
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Abstract
Description
[1] (A)芳香族エステル骨格及び不飽和結合含有化合物、及び
(B)ラジカル重合性化合物、を含有する樹脂組成物であって、
(A)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、0.1質量%以上30質量%以下である、樹脂組成物。
[2] (A)成分が、下記一般式(A−1)で表される化合物、及び下記一般式(A−2)で表される化合物のいずれかである、[1]に記載の樹脂組成物。
[3] さらに、(C)無機充填材を含有する、[1]又は[2]に記載の樹脂組成物。
[4] (C)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、50質量%以上である、[3]に記載の樹脂組成物。
[5] さらに、(D)熱可塑性樹脂を含有する、[1]〜[4]のいずれかに記載の樹脂組成物。
[6] さらに、(E)熱硬化性樹脂を含有する、[1]〜[5]のいずれかに記載の樹脂組成物。
[7] (B)成分が、マレイミド基を含有するマレイミド系ラジカル重合性化合物、及びビニルフェニル基を含有するビニルフェニル系ラジカル重合性化合物のいずれかを含有する、[1]〜[6]のいずれかに記載の樹脂組成物。
[8] 絶縁層形成用である、[1]〜[7]のいずれかに記載の樹脂組成物。
[9] 導体層を形成するための絶縁層形成用である、[1]〜[8]のいずれかに記載の樹脂組成物。
[10] 支持体と、該支持体上に設けられた、[1]〜[9]のいずれかに記載の樹脂組成物を含む樹脂組成物層とを含む、樹脂シート。
[11] [1]〜[9]のいずれかに記載の樹脂組成物の硬化物により形成された絶縁層を含む、プリント配線板。
[12] [11]に記載のプリント配線板を含む、半導体装置。
本発明の樹脂組成物は、(A)芳香族エステル骨格及び不飽和結合含有化合物、及び(B)ラジカル重合性化合物、を含有する樹脂組成物であって、(A)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、0.1質量%以上30質量%以下である。本発明では、所定量の(A)成分を含有させ、さらに(B)成分を含有させることで、硬化基板に生じるムラを抑制でき、誘電特性、及びピール強度に優れる硬化物を得ることができる。また、通常は、破断点伸度も優れる硬化物を得ることができる。
樹脂組成物は、(A)成分として(A)芳香族エステル骨格及び不飽和結合含有化合物を含有する。(A)成分を樹脂組成物に含有させることで、硬化基板に生じるムラを抑制でき、誘電特性に優れる硬化物を得ることが可能となる。(A)成分は1種単独で用いてもよく、2種以上を併用してもよい。
樹脂組成物は、(B)成分として(B)ラジカル重合性化合物を含む。但し、(B)成分には、(A)成分に該当するものは除かれる。(B)成分を樹脂組成物に含有させることにより、硬化基板に生じるムラを抑制でき、誘電特性、及びピール強度に優れる硬化物を得ることが可能となる。(B)成分は1種単独で用いてもよく、2種以上を併用してもよい。
恒温水槽:
攪拌機、ヒーター、温度計、自動温度調節器(±0.1℃で温度制御が可能なもの)を備えたもので深さ150mm以上のものを用いる。
なお、液状、半固形状、及び固形状の判定では、いずれもヤマト科学社製の低温恒温水槽(型式BU300)と投入式恒温装置サーモメイト(型式BF500)の組み合わせを用い、水道水約22リットルを低温恒温水槽(型式BU300)に入れ、これに組み付けられたサーモメイト(型式BF500)の電源を入れて設定温度(20℃又は60℃)に設定し、水温を設定温度±0.1℃にサーモメイト(型式BF500)で微調整しうるが、同様の調整が可能な装置であればいずれも使用できる。
試験管としては、図1に示すように、内径30mm、高さ120mmの平底円筒型透明ガラス製のもので、管底から55mmおよび85mmの高さのところにそれぞれ標線11A、12Bが付され、試験管の口をゴム栓13aで密閉した液状判定用試験管10aと、同じサイズで同様に標線が付され、中央に温度計を挿入・支持するための孔があけられたゴム栓13bで試験管の口を密閉し、ゴム栓13bに温度計14を挿入した温度測定用試験管10bを用いる。以下、管底から55mmの高さの標線を「A線」、管底から85mmの高さの標線を「B線」という。
温度計14としては、JIS B7410(1982)「石油類試験用ガラス製温度計」に規定する凝固点測定用のもの(SOP−58目盛範囲0〜100℃)を用いるが、0〜100℃の温度範囲が測定できるものであればよい。
温度60±5℃の大気圧下で24時間以上放置した試料を、図1(a)に示す液状判定用試験管10aと図1(b)に示す温度測定用試験管10bにそれぞれ11A線まで入れる。2本の試験管10a、10bを低温恒温水槽に12B線が水面下になるように直立させて静置する。温度計は、その下端が11A線よりも30mm下となるようにする。
試料温度が設定温度±0.1℃に達してから10分間そのままの状態を保持する。10分後、液状判断用試験管10aを低温恒温水槽から取り出し、直ちに水平な試験台の上に水平に倒し、試験管内の液面の先端が11A線から12B線まで移動した時間をストップウォッチで測定し、記録する。
20℃において、測定された時間が90秒を超え、60℃において、測定された時間が90秒以内のものを半固形状と判定する。
60℃において、測定された時間が90秒を超えるものを固体状と判定する。
炭素原子数が5以上のアルキニレン基の炭素原子数は、好ましくは6以上、より好ましくは8以上、好ましくは50以下、より好ましくは45以下、さらに好ましくは40以下である。このアルキニレン基は、直鎖状、分岐鎖状、環状のいずれであってもよく、中でも直鎖状が好ましい。ここで、環状のアルキニレン基とは、環状のアルキニレン基のみからなる場合と、直鎖状のアルキニレン基と環状のアルキニレン基との両方を含む場合も含める概念である。このようなアルキニレン基としては、例えば、ペンチニレン基、ヘキシニレン基、ヘプチニレン基、オクチニレン基、ノニニレン基、デシニレン基、ウンデシニレン基、ドデシニレン基、トリデシニレン基、ヘプタデシニレン基、ヘキサトリアコンチニレン基、オクチニレン−シクロヘキシニレン構造を有する基、オクチニレン−シクロヘキシニレン−オクチニレン構造を有する基、プロピニレン−シクロヘキシニレン−オクチニレン構造を有する基等が挙げられる。
一般式(B−9)中、M4、M6及びM7はそれぞれ独立に置換基を有していてもよい炭素原子数が5以上の脂肪族基を表し、M5はそれぞれ独立に置換基を有していてもよい芳香環を有する2価の基を表し、R41及びR42はそれぞれ独立に炭素原子数が5以上のアルキル基を表す。t2は0〜10の整数を表し、u1及びu2はそれぞれ独立に0〜4の整数を表す。
樹脂組成物は、上述した成分以外に、任意の成分として、更に、(C)成分として無機充填材を含有していてもよい。
樹脂組成物は、上述した成分以外に、任意の成分として、更に、(D)成分として熱可塑性樹脂を含有していてもよい。但し、(B)成分に該当するものは除かれる。(D)成分を樹脂組成物に含有させることで、樹脂組成物の応力が緩和され、その結果、誘電特性に優れる硬化物を得ることが可能となる。(D)成分は1種単独で用いてもよく、2種以上を併用してもよい。
R201及びR202は、それぞれ独立して、ハロゲン原子、シアノ基、ニトロ基、又は−X330−R330を示し、
X330は、それぞれ独立して、単結合、−NR330’−、−O−、−S−、−CO−、−SO2−、−NR330’CO−、−CONR330’−、−OCO−、又は−COO−を示し、
R330は、それぞれ独立して、置換又は無置換のアルキル基、又は置換又は無置換のアルケニル基を示し、
R330’は、それぞれ独立して、水素原子、置換又は無置換のアルキル基、又は置換又は無置換のアルケニル基を示し、
Y1は、単結合、或いは炭素原子、酸素原子、硫黄原子及び窒素原子から選ばれる1〜100個の骨格原子を有するリンカー構造を示し、
n10及びn11は、それぞれ独立して、0〜3の整数を示す。]
で表される化合物が挙げられる。
の何れかで表される2価の基であり、特に好ましくは、式(X2−1)で表される2価の基である。
で表される繰り返し単位を含む化合物であり、より好ましくは、式(1A−1)〜(1B−3):
の何れかで表される繰り返し単位を含む化合物であり、特に好ましくは、式(1A−1)で表される繰り返し単位を含む化合物である。
樹脂組成物は、上述した成分以外に、任意の成分として、更に、(E)成分として熱硬化性樹脂を含有していてもよい。但し、(A)成分及び(B)成分に該当するものは除く。(E)熱硬化性樹脂としては、例えば、エポキシ樹脂、フェノール系樹脂、ナフトール系樹脂、ベンゾオキサジン系樹脂、活性エステル系樹脂、シアネートエステル系樹脂、カルボジイミド系樹脂、アミン系樹脂、酸無水物系樹脂等が挙げられる。(E)成分は、1種類単独で用いてもよく、2種類以上を任意の比率で組み合わせて用いてもよい。以下、フェノール系樹脂、ナフトール系樹脂、ベンゾオキサジン系樹脂、活性エステル系樹脂、シアネートエステル系樹脂、カルボジイミド系樹脂、アミン系樹脂、酸無水物系樹脂のように、エポキシ樹脂と反応して樹脂組成物を硬化させることができる樹脂を、まとめて「硬化剤」ということがある。
樹脂組成物は、上述した成分以外に、任意の成分として、更に、(F)成分として硬化促進剤を含有していてもよい。(F)成分を含有させることで、熱による重合をより促進させることが可能となる。
樹脂組成物は、上述した成分以外に、任意の成分として、更にその他の添加剤を含んでいてもよい。このような添加剤としては、例えば、増粘剤、消泡剤、レベリング剤、密着性付与剤等の樹脂添加剤などが挙げられる。これらの添加剤は、1種類単独で用いてもよく、2種類以上を組み合わせて用いてもよい。それぞれの含有量は当業者であれば適宜設定できる。
樹脂組成物は、所定量の(A)成分、及び(B)成分を含む。これにより、硬化基板に生じるムラを抑制でき、誘電特性、ピール強度、及び破断点伸度に優れる硬化物を得ることができる。通常、無機充填材の含有量を多くすると、硬化基板に生じるムラが発生しやすくなる傾向にある。しかし、所定量の(A)成分及び(B)成分を組み合わせて含有させることで、無機充填材の含有量が多くても、硬化基板に生じるムラの発生を抑制することが可能となる。さらに、誘電特性、ピール強度、及び破断点伸度に優れる硬化物を得ることが可能となる。
(1)基材に仮固定フィルムを積層する工程、
(2)半導体チップを、仮固定フィルム上に仮固定する工程、
(3)半導体チップ上に封止層を形成する工程、
(4)基材及び仮固定フィルムを半導体チップから剥離する工程、
(5)半導体チップの基材及び仮固定フィルムを剥離した面に、絶縁層としての再配線形成層を形成する工程、及び
(6)再配線形成層上に、導体層としての再配線層を形成する工程
本発明の樹脂シートは、支持体と、該支持体上に設けられた、本発明の樹脂組成物で形成された樹脂組成物層を含む。
本発明のプリント配線板は、本発明の樹脂組成物の硬化物により形成された絶縁層を含む。
(I)内層基板上に、樹脂シートの樹脂組成物層が内層基板と接合するように積層する工程
(II)樹脂組成物層を熱硬化して絶縁層を形成する工程
本発明の半導体装置は、本発明のプリント配線板を含む。本発明の半導体装置は、本発明のプリント配線板を用いて製造することができる。
反応容器にオルトアリルフェノール89質量部、ジシクロペンタジエン・フェノール共重合樹脂(軟化点85℃、水酸基当量約165g/eq.)110質量部、トルエン1000質量部を仕込み、容器内を減圧窒素置換させながら溶解させた。続いて、イソフタル酸クロライド135質量部を仕込み溶解させた。次いでテトラブチルアンモニウムブロミド0.5gを添加し、容器内を窒素パージしながら20%水酸化ナトリウム水溶液309gを3時間かけ滴下した。その際、系内の温度は60℃以下に制御した。その後、1時間攪拌させ反応させた。反応終了後、反応物を分液し水層を取り除いた。水層のpHが7になるまでこの操作を繰り返し、加熱減圧条件でトルエン等を留去させ、芳香族エステル骨格及び不飽和結合含有化合物Aを得た。得られた芳香族エステル骨格及び不飽和結合含有化合物Aの不飽和結合当量は仕込み比から算出すると428g/eq.であった。化合物Aは下記式で表され、sは0又は1以上の整数を表し、仕込み比から算出されたrの平均値は1である。また、波線は、イソフタル酸クロリド、並びにフェノールの重付加反応樹脂及び/又はオルトアリルフェノールが反応して得られる構造である。
反応容器にオルトアリルフェノール201質量部、トルエン1000質量部を仕込み、容器内を減圧窒素置換させながら溶解させた。続いて、イソフタル酸クロライド152質量部を仕込み溶解させた。容器内を窒素パージしながら20%水酸化ナトリウム水溶液309gを3時間かけ滴下した。その際、系内の温度は60℃以下に制御した。その後、1時間攪拌させ反応させた。反応終了後、反応物を分液し水層を取り除いた。水層のpHが7になるまでこの操作を繰り返し、加熱減圧条件でトルエン等を留去させ、芳香族エステル骨格及び不飽和結合含有化合物Bを得た。得られた芳香族エステル骨格及び不飽和結合含有化合物Bの不飽和結合当量は仕込み比から算出すると199g/eq.であった。化合物Bは下記式で表される構造である。
環流冷却器を連結した水分定量受器、窒素導入管、及び攪拌器を備えた、500mLのセパラブルフラスコを用意した。このフラスコに、4,4’−オキシジフタル酸無水物(ODPA)20.3g、γ−ブチロラクトン200g、トルエン20g、及び、5−(4−アミノフェノキシ)−3−[4−(4−アミノフェノキシ)フェニル]−1,1,3−トリメチルインダン29.6gを加えて、窒素気流下で45℃にて2時間攪拌して反応を行った。次いで、この反応溶液を昇温し、約160℃に保持しながら、窒素気流下で縮合水をトルエンとともに共沸除去した。水分定量受器に所定量の水がたまっていること、及び、水の流出が見られなくなっていることを確認した。確認後、反応溶液を更に昇温し、200℃で1時間攪拌した。その後、冷却して、1,1,3−トリメチルインダン骨格を有するポリイミド樹脂を含むポリイミド溶液(不揮発分20質量%)を得た。得られたポリイミド樹脂は、下記式(X1)で表される繰り返し単位及び下記式(X2)で示す繰り返し単位を有していた。また、前記のポリイミド樹脂の重量平均分子量は、12,000であった。
4つ口フラスコに、894.96mmolのジクロロピリミジン、900.00mmolの1,1−ビス(4−ヒドロキシフェニル)−3,3,5−トリメチルシクロヘキサン、1.2molの炭酸カリウム、N−メチル−2−ピロリドン(450g)を入れた。フラスコ内を窒素置換した後、フラスコの内容物を130℃で6時間加熱し、加熱の際に生成する水をDean−Stark管から随時取り除いた。フラスコの内容物を室温に冷却後、析出した固形物を濾別し、濾液にメタノールを加え、析出した固形物をメタノールで洗浄し、これらの固形物を乾燥し、ビスフェノールエーテル樹脂(重量平均分子量(Mw);87000(ポリスチレン換算値))を得た。得られたビスフェノールエーテル樹脂を13C−NMRで測定し、生成物を確認した。ビスフェノールエーテル樹脂は下記式で表される構造である。
発明協会公開技報公技番号2020−500211号に記載の合成例1に記載の方法で合成されたマレイミド化合物のMEK溶液(不揮発成分70質量%)を用意した。このマレイミド化合物は、下記式で表される構造を有する。
合成例1にて得た化合物A 10部をトルエン10部、MEK10部に撹拌しながら加熱溶解させた。得られた溶液を室温にまで冷却した後、ビフェニルアラルキル型マレイミド樹脂(日本化薬社製「MIR−3000−70MT」、マレイミド基当量:275g/eq.、不揮発分70%のMEK/トルエン混合溶液)80部、合成例3にて得たポリイミド樹脂20質量%含むワニス15部、硬化促進剤(日油社製「パーヘキシルD」)1部、無機充填材(アミン系シランカップリング剤(信越化学工業社製「KBM573」)で表面処理された球形シリカ(アドマテックス社製「SO−C2」、平均粒径0.5μm))130部を混合し、高速回転ミキサーで均一に分散して樹脂組成物1を得た。
実施例1において、
1)化合物Aの量を10部から50部に変え、
2)ビフェニルアラルキル型マレイミド樹脂(日本化薬社製「MIR−3000−70MT」、マレイミド基当量:275g/eq.、不揮発分70%のMEK/トルエン混合溶液)の量を80部から70部に変え、
3)液状ビスマレイミド(デザイナーモレキュールズ社製「BMI689」、マレイミド基当量345g/eq.)7部を用い、
4)合成例3にて得たポリイミド樹脂20質量%含むワニス15部を、ポリアミドイミド樹脂(DIC社製「ユニディックV−8000」、重量平均分子量11000、不揮発成分40質量%のエチルジグリコールアセテート溶液)12.5部に変えた。
以上の事項以外は実施例1と同様にして樹脂組成物2を調製した。
実施例1において、
1)化合物Aの量を10部から20部に変え、
2)ビフェニルアラルキル型マレイミド樹脂(日本化薬社製「MIR−3000−70MT」、マレイミド基当量:275g/eq.、不揮発分70%のMEK/トルエン混合溶液)80部を、三菱ガス化学社製のオリゴフェニレンエーテル・スチレン樹脂「OPE−2St 1200」、不揮発分65%のトルエン溶液)60部に変え、
3)2官能アクリレート((メタ)アクリル系ラジカル重合性化合物、新中村化学工業社製「NKエステルA−DOG」、分子量326)5部を用い、
4)合成例3にて得たポリイミド樹脂20質量%含むワニス15部を、ポリカーボネート樹脂(三菱ガス化学社製「FPC2136」、重量平均分子量30000)5部に変えた。
以上の事項以外は実施例1と同様にして樹脂組成物3を調製した。
実施例1において、
1)ビフェニルアラルキル型マレイミド樹脂(日本化薬社製「MIR−3000−70MT」、マレイミド基当量:275g/eq.、不揮発分70%のMEK/トルエン混合溶液)の量を80部から40部に変え、
2)合成例3にて得たポリイミド樹脂20質量%含むワニス15部を、フェノキシ樹脂(三菱ケミカル社製「YX7553BH30」、重量平均分子量35000、固形分30質量%のMEKとシクロヘキサノンの1:1溶液)10部に変え、
3)ナフタレン型エポキシ樹脂(DIC社製、「HP4032SS」)10部、カルボジイミド系樹脂(日清紡ケミカル社製「V−03」、活性基当量約216、固形分50質量%のトルエン溶液)10部、活性エステル系樹脂(DIC社製「HPC−8000−65T」、活性基当量223、固形分65質量%のトルエン溶液)20部、及び硬化促進剤(4−ジメチルアミノピリジン(DMAP)、固形分10質量%のMEK溶液)1部を用いた。
以上の事項以外は実施例1と同様にして樹脂組成物4を調製した。
実施例1において、合成例1にて得た化合物A 10部を、合成例2にて得た化合物B 10部に変えた。以上の事項以外は実施例1と同様にして樹脂組成物5を調製した。
実施例3において、合成例1にて得た化合物A 20部を、合成例2にて得た化合物B 20部に変えた。以上の事項以外は実施例3と同様にして樹脂組成物6を調製した。
実施例3において、合成例1にて得た化合物A 20部を、合成例2にて得た化合物B 50部に変えた。以上の事項以外は実施例3と同様にして樹脂組成物7を調製した。
実施例4において、
1)合成例1にて得た化合物A 10部を、合成例2にて得た化合物B 20部に変え、
2)ビフェニルアラルキル型マレイミド樹脂(日本化薬社製「MIR−3000−70MT」、マレイミド基当量:275g/eq.、不揮発分70%のMEK/トルエン混合溶液)40部を、オリゴフェニレンエーテル・スチレン樹脂(三菱ガス化学社製「OPE−2St 1200」、不揮発分65%のトルエン溶液)30部に変えた。
以上の事項以外は実施例4と同様にして樹脂組成物8を調製した。
実施例1において、合成例1にて得た化合物A 10部を用いなかった。以上の事項以外は実施例1と同様にして比較用樹脂組成物1を調製した。
実施例1において、合成例1にて得た化合物Aの量を10部から85部に変えた。以上の事項以外は実施例1と同様にして比較用樹脂組成物2を調製した。
実施例6において、合成例2にて得た化合物Bの量を20部から85部に変えた。以上の事項以外は実施例6と同様にして比較用樹脂組成物3を調製した。
実施例1において、合成例3のポリイミド樹脂15部を合成例4のビスフェノールエーテル樹脂の不揮発分20%のシクロヘキサノン溶液15部に変えた。以上の事項以外は実施例1と同様にして樹脂組成物9を調製した。
実施例1において、ビフェニルアラルキル型マレイミド樹脂(日本化薬社製「MIR−3000−70MT」、マレイミド基当量:275g/eq.、不揮発分70%のMEK/トルエン混合溶液)80部を、合成例5のマレイミド樹脂(不揮発成分70質量%のMEK溶液)80部に変えた。以上の事項以外は実施例1と同様にして樹脂組成物10を調製した。
実施例3において、合成例1にて得た化合物Aの量を20部から50部に変え、三菱ガス化学社製のオリゴフェニレンエーテル・スチレン樹脂「OPE−2St 1200」、不揮発分65%のトルエン溶液)60部を、日鉄ケミカル&マテリアル社製「ODV−XET−X04」(重量平均分子量3110、65質量%溶液)67.7部に変え、2官能アクリレート((メタ)アクリル系ラジカル重合性化合物、新中村化学工業社製「NKエステルA−DOG」、分子量326)を用いなかった。以上の事項以外は実施例3と同様にして樹脂組成物11を調製した。
実施例3において、三菱ガス化学社製のオリゴフェニレンエーテル・スチレン樹脂「OPE−2St 1200」、不揮発分65%のトルエン溶液)60部を、ベンゾシクロブテン樹脂(ダウ・ケミカル社製「CYCLOTENE 3022」)44部に変え、ポリカーボネート樹脂(三菱ガス化学社製「FPC2136」、重量平均分子量30000)5部を、フェノキシ樹脂(三菱ケミカル社製「YX7553BH30」、重量平均分子量35000、固形分30質量%のMEKとシクロヘキサノンの1:1溶液)16.7部に変えた。以上の事項以外は実施例3と同様にして樹脂組成物12を調製した。
実施例9において、合成例1にて得た化合物A 10部を、合成例2にて得た化合物B 10部に変えた。以上の事項以外は実施例9と同様にして樹脂組成物13を調製した。
実施例10において、合成例1にて得た化合物A 10部を、合成例2にて得た化合物B 10部に変えた。以上の事項以外は実施例10と同様にして樹脂組成物14を調製した。
実施例11において、合成例1にて得た化合物A 50部を、合成例2にて得た化合物B 20部に変えた。以上の事項以外は実施例11と同様にして樹脂組成物15を調製した。
実施例12において、合成例1にて得た化合物A 20部を、合成例2にて得た化合物B 50部に変えた。以上の事項以外は実施例12と同様にして樹脂組成物16を調製した。
支持体として、アルキド樹脂系離型剤(リンテック社製「AL−5」)で離型処理を施したポリエチレンテレフタレートフィルム(東レ社製「ルミラーR80」、厚み38μm、軟化点130℃)を用意した。
(1)内層基板の用意
内層回路を形成したガラス布基材エポキシ樹脂両面銅張積層板(銅箔の厚さ18μm、基板の厚さ0.4mm、パナソニック社製「R1515A」)の両面をマイクロエッチング剤(メック社製「CZ8101」)にて1μmエッチングして銅表面の粗化処理を行った。
樹脂シートから保護フィルムを剥がして、樹脂組成物層を露出させた。バッチ式真空加圧ラミネーター(ニッコー・マテリアルズ社製、2ステージビルドアップラミネーター「CVP700」)を用いて、樹脂組成物層が内層基板と接するように、内層基板の両面にラミネートした。ラミネートは、30秒間減圧して気圧を13hPa以下に調整した後、120℃、圧力0.74MPaにて30秒間圧着させることにより実施した。次いで、100℃、圧力0.5MPaにて60秒間熱プレスを行った。
その後、樹脂シートがラミネートされた内層基板を、130℃のオーブンに投入して30分間加熱し、次いで170℃のオーブンに移し替えて30分間加熱して、樹脂組成物層を熱硬化させて、絶縁層を形成した。その後、支持体を剥離して、絶縁層、内層基板及び絶縁層をこの順に有する硬化基板Aを得た。
硬化基板Aの両面について、樹脂シートがラミネートされた部分(積層板とは反対側の表面)の表面均一性の観察を目視にて行い、下記のように評価した。
◎:ムラが全く観察されず、完全に均一な表面である。
〇:樹脂シートがラミネートされた部分の外周から1cmの部分のみにムラが観察され、それより内側の部分は完全に均一な表面である。
×:樹脂シートがラミネートされた部分の外周から1cmより内側の部分に、不均一な部分が観察される。
硬化基板Aに、粗化処理としてのデスミア処理を行った。デスミア処理としては、下記の湿式デスミア処理を実施した。
(湿式デスミア処理)
硬化基板Aを、膨潤液(アトテックジャパン社製「スウェリング・ディップ・セキュリガントP」、ジエチレングリコールモノブチルエーテル及び水酸化ナトリウムの水溶液)に60℃で5分間浸漬し、次いで、酸化剤溶液(アトテックジャパン社製「コンセントレート・コンパクトCP」、過マンガン酸カリウム濃度約6%、水酸化ナトリウム濃度約4%の水溶液)に80℃で15分間浸漬し、次いで、中和液(アトテックジャパン社製「リダクションソリューション・セキュリガントP」、硫酸水溶液)に40℃で5分間浸漬した後、80℃で15分間乾燥した。
セミアディティブ法に従って、絶縁層の粗化面に導体層を形成した。すなわち、粗化処理後の基板を、PdCl2を含む無電解メッキ液に40℃で5分間浸漬した後、無電解銅メッキ液に25℃で20分間浸漬した。次いで、150℃にて30分間加熱してアニール処理を行った後に、エッチングレジストを形成し、エッチングによりパターン形成した。その後、硫酸銅電解メッキを行い、厚さ30μmの導体層を形成し、アニール処理を200℃にて60分間行った。得られた基板を「評価基板B」と称する。
絶縁層と導体層のピール強度の測定は、日本工業規格(JIS C6481)に準拠して行った。具体的には、評価基板Bの導体層に、幅10mm、長さ100mmの部分の切込みをいれ、この一端を剥がしてつかみ具で掴み、室温中にて、50mm/分の速度で垂直方向に35mmを引き剥がした時の荷重(kgf/cm)を測定し、剥離強度を求めた。測定には、引っ張り試験機(TSE社製「AC−50C−SL」)を使用した。
実施例及び比較例で作製した樹脂シートから保護フィルムを剥がして、200℃にて90分間加熱して樹脂組成物層を熱硬化させた後、支持体を剥離した。得られた硬化物を「評価用硬化物C」と称する。評価用硬化物Cを、幅2mm、長さ80mmの試験片に切断した。該試験片について、アジレントテクノロジーズ社製「HP8362B」を用いて、空洞共振摂動法により測定周波数5.8GHz、測定温度23℃にて誘電率、誘電正接を測定した。3本の試験片について測定を行い、平均値を算出した。
評価用硬化物Cについて、日本工業規格(JIS K7127)に準拠して、テンシロン万能試験機(オリエンテック社製「RTC−1250A」)により引っ張り試験を行い、破断点伸度(%)を測定した。
Claims (12)
- (A)芳香族エステル骨格及び不飽和結合含有化合物、及び
(B)ラジカル重合性化合物、を含有する樹脂組成物であって、
(A)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、0.1質量%以上30質量%以下である、樹脂組成物。 - (A)成分が、下記一般式(A−1)で表される化合物、及び下記一般式(A−2)で表される化合物のいずれかである、請求項1に記載の樹脂組成物。
- さらに、(C)無機充填材を含有する、請求項1又は2に記載の樹脂組成物。
- (C)成分の含有量が、樹脂組成物中の不揮発成分を100質量%とした場合、50質量%以上である、請求項3に記載の樹脂組成物。
- さらに、(D)熱可塑性樹脂を含有する、請求項1〜4のいずれか1項に記載の樹脂組成物。
- さらに、(E)熱硬化性樹脂を含有する、請求項1〜5のいずれか1項に記載の樹脂組成物。
- (B)成分が、マレイミド基を含有するマレイミド系ラジカル重合性化合物、及びビニルフェニル基を含有するビニルフェニル系ラジカル重合性化合物のいずれかを含有する、請求項1〜6のいずれか1項に記載の樹脂組成物。
- 絶縁層形成用である、請求項1〜7のいずれか1項に記載の樹脂組成物。
- 導体層を形成するための絶縁層形成用である、請求項1〜8のいずれか1項に記載の樹脂組成物。
- 支持体と、該支持体上に設けられた、請求項1〜9のいずれか1項に記載の樹脂組成物を含む樹脂組成物層とを含む、樹脂シート。
- 請求項1〜9のいずれか1項に記載の樹脂組成物の硬化物により形成された絶縁層を含む、プリント配線板。
- 請求項11に記載のプリント配線板を含む、半導体装置。
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