JP5524525B2 - 樹脂付銅箔、積層板およびプリント配線板 - Google Patents
樹脂付銅箔、積層板およびプリント配線板 Download PDFInfo
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- JP5524525B2 JP5524525B2 JP2009167658A JP2009167658A JP5524525B2 JP 5524525 B2 JP5524525 B2 JP 5524525B2 JP 2009167658 A JP2009167658 A JP 2009167658A JP 2009167658 A JP2009167658 A JP 2009167658A JP 5524525 B2 JP5524525 B2 JP 5524525B2
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- Prior art keywords
- resin
- epoxy resin
- copper foil
- layer
- resin layer
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- 229920005989 resin Polymers 0.000 title claims description 117
- 239000011347 resin Substances 0.000 title claims description 117
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 51
- 239000011889 copper foil Substances 0.000 title claims description 51
- 239000003822 epoxy resin Substances 0.000 claims description 91
- 229920000647 polyepoxide Polymers 0.000 claims description 91
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 239000011256 inorganic filler Substances 0.000 claims description 25
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 230000001588 bifunctional effect Effects 0.000 claims description 19
- 238000002844 melting Methods 0.000 claims description 14
- 230000008018 melting Effects 0.000 claims description 14
- 239000005011 phenolic resin Substances 0.000 claims description 13
- 229920001568 phenolic resin Polymers 0.000 claims description 12
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000000465 moulding Methods 0.000 claims description 10
- 239000002648 laminated material Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 238000004455 differential thermal analysis Methods 0.000 claims description 8
- 239000011342 resin composition Substances 0.000 claims description 8
- 229920006038 crystalline resin Polymers 0.000 claims description 3
- 238000001723 curing Methods 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 10
- -1 3-hydroxyphenoxy Chemical group 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000003700 epoxy group Chemical group 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
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- 230000000694 effects Effects 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
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- 238000004132 cross linking Methods 0.000 description 5
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229920006026 co-polymeric resin Polymers 0.000 description 4
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- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
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- 239000002585 base Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 3
- 229910002026 crystalline silica Inorganic materials 0.000 description 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 3
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- IXCOKTMGCRJMDR-UHFFFAOYSA-N 9h-fluorene;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 IXCOKTMGCRJMDR-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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Description
4,4’−ジヒドロキシジフェニルエーテル1010gをエピクロルヒドリン6475gに溶解し、減圧下(約120mmHg、60℃にて48%水酸化ナトリウム水溶液808gを4時間かけて滴下した。この間、生成する水はエピクロルヒドリンとの共沸により系外に除き、溜出したエピクロルヒドリンは系内に戻した。滴下終了後、さらに1時間反応を継続した。その後、エピクロルヒドリンを減圧留去し、メチルイソブチルケトン3660gに溶解した後、濾過により生成した塩を除いた。その後、20%水酸化ナトリウム水溶液119.4gを加え、80℃で2時間反応させた。反応後、濾過、水洗を行った後、溶媒であるメチルイソブチルケトンを減圧留去し、淡黄色結晶のエポキシ樹脂(エポキシ樹脂A)1440gを得た。得られたエポキシ樹脂のエポキシ当量は163g/eq.、加水分解性塩素は280ppm、融点は78から84℃、150℃での粘度は6.2mPa・sであった。得られた樹脂のGPC測定より求められた一般式(1)における各成分比は、n=0が92.2%、n=1が7.8%であった。ここで、加水分解性塩素とは、試料0.5gをジオキサン30mlに溶解後、1N−KOH、10mlを加え30分間煮沸還流した後、室温まで冷却し、さらに80%アセトン水100mlを加えたものを、0.002N−AgNO3水溶液で電位差滴定を行うことにより測定された値である。また融点とは、キャピラリー法により昇温速度2℃/分で得られる値である。粘度はBROOKFIELD製、CAP2000Hで測定し、軟化点はJIS K−6911に従い環球法で測定した。また、GPC測定は、装置;日本ウォーターズ(株)製、515A型、カラム;TSK−GEL2000×3本およびTSK−GEL4000×1本(いずれも東ソー(株)製)、溶媒;テトラヒドロフラン、流量;1 ml/min、温度;38℃、検出器;RIの条件に従った。
4,4'−ジヒドロキシジフェニルメタン100g、エピクロルヒドリン925g、48%水酸化ナトリウム水溶液80.8gを用いて、合成例1と同様に反応を行い、淡黄色液状の粗製エポキシ樹脂(エポキシ樹脂B)152gを得た。エポキシ当量は167であり、結晶化後の融点は58〜65℃であった。また、加水分解性塩素は280ppm、得られた樹脂のGPC測定より求められた一般式(1)における各成分比は、n=0が92.5%、n=1が6.0%であった。
エポキシ樹脂成分として、合成例1、2のエポキシ樹脂(エポキシ樹脂A、B)、ビフェニル系エポキシ樹脂(エポキシ樹脂C:ジャパンエポキシレジン製、YL−6121(4,4’−ジヒドロキシビフェニルのエポキシ化物と3,3’,5,5’−テトラメチル−4,4’−ジヒドロキシビフェニルのエポキシ化物との1:1の混合物)、エポキシ当量183)、o-クレゾールノボラック型エポキシ樹脂(エポキシ樹脂D:日本化薬製、EOCN-1020、エポキシ当量 197、軟化点54℃)、を使用し、硬化剤として4,4’−ジヒドロキシジフェニルエーテル(硬化剤A、平均粒径4.8μm)、4,4’−ジヒドロキシジフェニルメタン(硬化剤B、平均粒径6.5μm)、4,4’−ジヒドロキシビフェニル(硬化剤C、平均粒径2.3μm)、又はフェノールノボラック(硬化剤D:群栄化学製、PSM−4261;OH当量103、軟化点 82℃)を使用した。また、硬化促進剤としてトリフェニルホスフィン、無機充填材として球状アルミナ(平均粒径12.2μm)、溶剤としてシクロペンタノンを使用した。表1に示す成分を配合し、プラネタリーミキサーで十分混合して樹脂ワニス溶液を調整した。なお、表1中の各配合物の数字は重量部を表す。
熱伝導率は、NETZSCH製LFA447型熱伝導率計を用いて非定常熱線法により測定した。
(2)融点、融解熱の測定(DSC法)
示差走査熱量分析装置(セイコーインスツル製DSC6200型)を用い、昇温速度10℃/分で測定した。
(3)線膨張係数、ガラス転移点
線膨張係数およびガラス転移点は、セイコーインスツル製TMA120C型熱機械測定装置を用いて、昇温速度10℃/分にて測定した。
(4)吸水率
直径50mm、厚さ3mmの円盤を成形し、ポストキュア後、85℃、相対湿度85%の条件で100時間吸湿させた後の重量変化率とした。
Claims (4)
- エポキシ樹脂と硬化剤を含むエポキシ樹脂組成物をBステージ状態にした樹脂組成物の樹脂層を銅箔の片面に備えてなる樹脂付銅箔を全層ないしは一部の層として有する積層材料を、加熱加圧成形してなる積層板を製造するにあたり、当該エポキシ樹脂として二官能成分が90wt%以上であるエポキシ樹脂を用い、当該硬化剤として二官能成分が90wt%以上であるフェノール性樹脂を用いること、当該Bステージ状態にした樹脂組成物の樹脂層が走査示差熱分析における融点のピークが150℃から300℃の範囲にある結晶性の樹脂層であること、及び加熱加圧成形を樹脂層の融点のピーク温度から±15℃の温度でおこなうこと、示差熱分析における吸熱ピーク温度よりも5℃から50℃低い温度で、1時間から24時間かけてポストキュアを行うことを特徴とするプリント配線板用の積層板の製造方法。
- エポキシ樹脂組成物が無機充填材を50から96wt%含有したものであることを特徴とする請求項1〜3のいずれかに記載の積層板の製造方法。
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