JP5760099B2 - 新規な絶縁膜用樹脂組成物及びその利用 - Google Patents
新規な絶縁膜用樹脂組成物及びその利用 Download PDFInfo
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- JP5760099B2 JP5760099B2 JP2013555154A JP2013555154A JP5760099B2 JP 5760099 B2 JP5760099 B2 JP 5760099B2 JP 2013555154 A JP2013555154 A JP 2013555154A JP 2013555154 A JP2013555154 A JP 2013555154A JP 5760099 B2 JP5760099 B2 JP 5760099B2
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 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
- 239000003223 protective agent Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 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
- 229910052712 strontium Inorganic materials 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CPOUUWYFNYIYLQ-UHFFFAOYSA-M tetra(propan-2-yl)azanium;hydroxide Chemical compound [OH-].CC(C)[N+](C(C)C)(C(C)C)C(C)C CPOUUWYFNYIYLQ-UHFFFAOYSA-M 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 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
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
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- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- DIHAURBCYGTGCV-UHFFFAOYSA-N xi-4,5-Dihydro-2,4(5)-dimethyl-1H-imidazole Chemical compound CC1CN=C(C)N1 DIHAURBCYGTGCV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
- PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
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- H05K3/34—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by soldering
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Description
本発明にかかる絶縁膜用樹脂組成物は、少なくとも(A)バインダーポリマー、及び(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子を含有している樹脂組成物であり、そして絶縁膜を形成するために用いられる樹脂組成物である。
本発明における(A)バインダーポリマーは、有機溶媒に対して可溶性であり、その重量平均分子量が、ポリエチレングリコール換算で1,000以上、1,000,000以下のポリマーである。
使用装置:東ソー HLC−8220GPC相当品
カラム:東ソー TSK gel Super AWM−H(6.0mmI.D.×15cm)×2本
ガードカラム:東ソー TSK guard column Super AW−H
溶離液:30mM LiBr+20mM H3PO4 in DMF
流速:0.6mL/min
カラム温度:40℃
検出条件:RI:ポラリティ(+)、レスポンス(0.5sec)
試料濃度:約5mg/mL
標準品:PEG(ポリエチレングリコール)。
本発明における(a1)ウレタン結合を含有する樹脂は、有機溶媒に対して可溶性であり、少なくとも1つのウレタン結合を含有する繰り返し単位を分子内に含んでいる、重量平均分子量が、ポリエチレングリコール換算で1,000以上、1,000,000以下のポリマーである。
本発明における(a2)カルボキシル基を含有する樹脂は、有機溶媒に対して可溶性であり、少なくとも1つのカルボキシル基を含有する繰り返し単位を分子内に含んでいる、重量平均分子量が、ポリエチレングリコール換算で1,000以上、1,000,000以下のポリマーである。
本発明における(a3)イミド基を含有する樹脂は、有機溶媒に対して可溶性であり、少なくとも1つのイミド基を含有する繰り返し単位を分子内に含んでいる、重量平均分子量が、ポリエチレングリコール換算で1,000以上、1,000,000以下のポリマーである。
本発明における(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子は、少なくとも1つのウレタン結合、カーボネート骨格、及び架橋構造を分子内に有している、平均粒子径が1μm以上、100μm以下の球状ポリマー粒子である。ここで、球状とは、真球状であってもよいし、楕円状であってもよい。平均粒子径が1μm未満の場合は、絶縁膜用樹脂組成物の粘度やチクソ性が高くなり、塗工時の塗膜の発泡やレベリング不足による外観不良が発生するおそれがあり、平均粒子径が100μmより大きい場合は、絶縁膜用樹脂組成物から得られる絶縁膜の表面に粒子が露出し絶縁膜の表面平滑性が不良になるおそれがある。
使用装置:株式会社堀場製作所製 LA−950V2相当品
測定方式:レーザー回折/散乱式。
で示されるポリカーボネートジオールを用いることにより、カーボネート骨格を(B)成分の分子内に導入することができる。これにより、絶縁膜用樹脂組成物から得られる絶縁膜は耐加水分解性に優れるので、柔軟性や耐折れ性を犠牲にすることなく高温・高湿環境下での電気絶縁信頼性に優れる絶縁膜が得られる。
本発明における(C)熱硬化性樹脂は、少なくとも1つの熱硬化性の有機基を分子内に含有している構造の化合物である。
本発明における(D)分子内にラジカル重合性基を有する化合物は、ラジカル重合開始剤により重合反応が進行するラジカル重合性基を分子内に少なくとも1つ含有する化合物である。上記化合物の中でも、上記ラジカル重合性基が、不飽和二重結合である化合物であることが好ましい。さらには、上記不飽和二重結合は、(メタ)アクリロイル基、またはビニル基であることが好ましい。上記(D)分子内にラジカル重合性基を有する化合物を用いることにより、本発明にかかる絶縁膜用樹脂組成物が絶縁膜用感光性樹脂組成物となるため、露光、現像によって当該絶縁膜用樹脂組成物に微細加工を行うことが可能となる。
本発明における(E)光重合開始剤は、UVなどのエネルギーによって活性化し、ラジカル重合性基の反応を開始・促進させる化合物である。上記(E)光重合開始剤を(D)分子内にラジカル重合性基を有する化合物と共に用いることにより、本発明にかかる絶縁膜用樹脂組成物が絶縁膜用感光性樹脂組成物となるため、露光、現像によって絶縁膜用樹脂組成物に微細加工を行うことが可能となる。
本発明における(F)リン系難燃剤は、分子内に少なくとも1つのリン元素を含有しており、有機物の燃焼を抑制する効果を有する化合物である。
本発明にかかる絶縁膜用樹脂組成物には、さらに必要に応じて充填剤、接着助剤、消泡剤、レベリング剤、着色剤、または重合禁止剤等の各種添加剤を加えることができる。
本発明にかかる絶縁膜用樹脂組成物は、上記(A)〜(F)成分及びその他の成分を粉砕・分散して混合することにより、得ることができる。粉砕・分散方法としては、特に限定されるものではないが、例えば、ビーズミル、ボールミル、または3本ロール等の一般的な混練装置を用いて行われる。粉砕・分散方法として、この中でも、特にビーズミルを用いて粉砕・分散して混合した場合、微粒子として存在する(B)成分の粒度分布が均一になるため好ましい。
本発明にかかる絶縁膜用樹脂組成物を直接的に用いて、又は、絶縁膜用樹脂組成物溶液を調製した後に、以下のようにして絶縁膜を形成することができる。先ず、上記絶縁膜用樹脂組成物、又は、絶縁膜用樹脂組成物溶液を基板に塗布し、乾燥させて有機溶媒を除去する。基板への塗布はスクリーン印刷、カーテンロール、リバースロール、スプレーコーティング、またはスピンナーを利用した回転塗布等により行うことができる。塗布膜(好ましくは厚さ:5μm以上、100μm以下、特に10μm以上、100μm以下)の乾燥は120℃以下、好ましくは40℃以上、100℃以下で行う。
<(A)バインダーポリマー1>
攪拌機、温度計、滴下漏斗、冷却管及び窒素導入管を備えた反応容器に、重合用溶媒としてメチルトリグライム(=1,2−ビス(2−メトキシエトキシ)エタン)25.00gを仕込み、これに、ノルボルネンジイソシアネート5.16g(0.024モル)を添加し、窒素気流下で攪拌しながら80℃に加温して溶解させた。得られた溶液に、ポリカーボネートジオール50.00g(0.025モル)(旭化成ケミカルズ株式会社製、製品名:PCDL T5652、重量平均分子量:2,000)をメチルトリグライム25.00gに溶解させた溶液を1時間かけて滴下漏斗から滴下した。滴下終了後、得られた溶液を5時間にわたって80℃で加熱攪拌を行い反応させた。上記反応を行うことで分子内にウレタン結合を含有する樹脂溶液を得た。得られた樹脂溶液の固形分濃度は53%、重量平均分子量は5,600であった。尚、固形分濃度、重量平均分子量は下記の方法で測定した。
JIS K 5601−1−2に従って測定を行った。尚、乾燥条件は170℃×1時間の条件を選択した。
下記条件で測定を行った。
使用装置:東ソー HLC−8220GPC相当品
カラム:東ソー TSK gel Super AWM−H(6.0mmI.D.×15cm)×2本
ガードカラム:東ソー TSK guard column Super AW−H
溶離液:30mM LiBr+20mM H3PO4 in DMF
流速:0.6mL/min
カラム温度:40℃
検出条件:RI:ポラリティ(+)、レスポンス(0.5sec)
試料濃度:約5mg/mL
標準品:PEG(ポリエチレングリコール)。
<(A)バインダーポリマー2>
攪拌機、温度計、滴下漏斗、冷却管及び窒素導入管を備えた反応容器に、重合用溶媒としてメチルトリグライム(=1,2−ビス(2−メトキシエトキシ)エタン)30.00gを仕込み、これに、ノルボルネンジイソシアネート10.31g(0.050モル)を添加し、窒素気流下で攪拌しながら80℃に加温して溶解させた。得られた溶液に、ポリカーボネートジオール50.00g(0.025モル)(旭化成ケミカルズ株式会社製、製品名:PCDL T5652、重量平均分子量:2,000)及び2,2−ビス(ヒドロキシメチル)ブタン酸3.70g(0.025モル)をメチルトリグライム30.00gに溶解させた溶液を1時間かけて滴下漏斗から滴下した。滴下終了後、得られた溶液を5時間にわたって80℃で加熱攪拌を行い反応させた。上記反応を行うことで分子内にウレタン結合及びカルボキシル基を含有する樹脂溶液を得た。得られた樹脂溶液の固形分濃度は52%、重量平均分子量は5,600、固形分の酸価は22mgKOH/gであった。尚、固形分濃度、重量平均分子量は上記合成例1と同様の方法で、酸価は下記の方法で測定した。
JIS K 5601−2−1に従って測定を行った。
<(A)バインダーポリマー3>
攪拌機、温度計、滴下漏斗、冷却管及び窒素導入管を備えた反応容器に、重合用溶媒としてメチルトリグライム(=1,2−ビス(2−メトキシエトキシ)エタン)100.00gを仕込み、窒素気流下で攪拌しながら80℃まで昇温した。これに、室温(23℃)で予め混合しておいた、メタクリル酸12.00g(0.14モル)、メタクリル酸ベンジル28.00g(0.16モル)、メタクリル酸ブチル60.00g(0.42モル)、ラジカル重合開始剤としてアゾビスイソブチロニトリル0.50gを80℃に保温した状態で3時間かけて滴下漏斗から滴下した。滴下終了後、反応溶液を攪拌しながら90℃まで昇温し、反応溶液の温度を90℃に保ちながら更に2時間、加熱攪拌を行い反応させた。上記反応を行うことで分子内にカルボキシル基を含有する樹脂溶液を得た。得られた樹脂溶液の固形分濃度は50%、重量平均分子量は48,000、固形分の酸価は78mgKOH/gであった。尚、固形分濃度、重量平均分子量は上記合成例1と同様の方法で、酸価は合成例2と同様の方法で測定した。
<(A)バインダーポリマー4>
攪拌機、温度計、冷却管及び窒素導入管を備えた反応容器に、重合用溶媒としてメチルトリグライム(=1,2−ビス(2−メトキシエトキシ)エタン)130.60gを仕込み、これに、3,3’,4,4’−オキシジフタル酸二無水物31.02g(0.100モル)、ビス[4−(3−アミノフェノキシ)フェニル]スルホン12.92g(0.030モル)、ポリ(テトラメチレン/3−メチルテトラメチレンエーテル)グリコールビス(4−アミノベンゾエート)86.66g(0.070モル)を添加し、窒素気流下で30分間攪拌し、ポリアミド酸溶液を得た。次いで、このポリアミド酸溶液を190℃に加温して2時間にわたって反応させた。上記反応を行うことで分子内にイミド基を含有する樹脂溶液を得た。得られた樹脂溶液の固形分濃度は49%、重量平均分子量は28,000であった。尚、固形分濃度、重量平均分子量は上記合成例1と同様の方法で測定した。
<(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子>
攪拌機、温度計、滴下漏斗、冷却管及び窒素導入管を備えた1Lのセパラブルフラスコにイオン交換水400.00gを仕込み、窒素気流下で攪拌しながら60℃まで昇温した。これに、室温(23℃)で予め混合しておいた、ポリカーボネートジオール94.00g(旭化成ケミカルズ株式会社製、製品名:PCDL T5652、重量平均分子量:2,000)、ヘキサメチレンジイソシアネート系イソシアヌレート型ポリイソシアネート56.00g(旭化成ケミカルズ株式会社製、製品名:デュラネートTPA−100、NCO含有量:23.1wt%)、溶媒としてメチルエチルケトン50.00g、及び重合触媒としてジブチルスズジラウリレート0.0015gの混合溶液を60℃に保温した状態で2時間かけて滴下漏斗から滴下した。滴下終了後、反応溶液を攪拌しながら60℃で4時間にわたって攪拌を行い反応させた。次いで、反応溶液を室温(23℃)まで冷却し、固体を分離した後、イオン交換水で3回洗浄し、70℃で20時間にわたって乾燥させて架橋ポリマー粒子を得た。得られた架橋ポリマー粒子の平均粒子径は6μm、吸油量は90ml/100gであった。尚、平均粒子径、吸油量は下記方法で測定した。
使用装置:株式会社堀場製作所製 LA−950V2
測定方式:レーザー回折/散乱式。
JIS K 5101−13−2に従って測定を行った。
<絶縁膜用樹脂組成物の調製>
合成例1〜4で得られた(A)バインダーポリマー1〜4に、合成例5で得られた(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子、(C)熱硬化性樹脂、(F)リン系難燃剤、その他の成分、及び有機溶媒を添加して、実施例1〜7にかかる絶縁膜用樹脂組成物を作製した。それぞれの絶縁膜用樹脂組成物における構成原料の樹脂固形分での配合量及び原料の種類を表1に記載する。なお、表1中の溶媒である1,2−ビス(2−メトキシエトキシ)エタンは上記合成した樹脂溶液に含まれる溶剤も含めた全溶剤量である。絶縁膜用樹脂組成物は、先ず、一般的な攪拌翼のついた攪拌装置にて混合し、その後、3本ロールミルに2回通して、均一な溶液とした。グラインドメーターにて混合溶液中の絶縁膜用樹脂組成物の粒子径を測定したところ、いずれも10μm以下であった。混合溶液中の泡を脱泡装置にて完全に脱泡した後、下記評価を実施した。
<1>日産化学株式会社製 多官能エポキシ樹脂(トリグリシジルイソシアヌレート)の製品名
<2>クラリアントジャパン株式会社製 ホスフィン酸塩の製品名
<3>日産化学株式会社製 メラミンの製品名
<4>共栄社化学株式会社製 ブタジエン系消泡剤の製品名。
実施例1〜7にかかる絶縁膜用樹脂組成物を、ベーカー式アプリケーターを用いて、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:25NPI)の表面に最終乾燥厚さが20μmになるように100mm×100mmの面積に流延・塗布し、80℃で20分間乾燥させた後、150℃のオーブン中で30分間、加熱硬化させた。これにより、ポリイミドフィルム上に絶縁膜用樹脂組成物の絶縁膜(硬化膜)を形成して、絶縁膜積層フィルム(絶縁膜用樹脂フィルム)を作製した。
以下の項目について、得られた絶縁膜積層フィルムの評価を行った。評価結果を表2に記載する。
実施例1〜7にかかる絶縁膜用樹脂組成物を、ベーカー式アプリケーターを用いて、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:25NPI)の表面に最終乾燥厚さが20μmになるように100mm×100mmの面積に流延・塗布し、80℃で20分間乾燥させ、溶媒乾燥後に塗膜を形成して、塗膜付きフィルムを作製した。塗膜のタック性の評価方法は、作製した溶媒乾燥後の塗膜付きフィルムを50mm×30mmの短冊に切り出して、塗膜を内側にして塗膜面同士を重ね合わせ、重ね合わせた部分に300gの荷重を3秒間のせた後、荷重を取り除き、塗膜面を引き剥がしたときの状態を観察した。観察結果を下記「○」、「△」または「×」で示す。
○:塗膜同士の貼り付きがなく、塗膜に貼り付き跡も残っていない
△:塗膜同士が少し貼り付き、塗膜に貼り付き跡が残っている
×:塗膜同士が完全に貼り付いて引き剥がせない。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル25NPI)の表面に最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。絶縁膜積層フィルムの耐折れ性の評価方法は、当該絶縁膜積層フィルムを50mm×10mmの短冊に切り出して、絶縁膜を外側にして25mmのところ(中央部)で180°に折り曲げ、折り曲げ部に5kgの荷重を3秒間のせた後、荷重を取り除き、折り曲げ部の頂点を顕微鏡で観察することによって行った。顕微鏡で観察した後、折り曲げ部を180°程度開いて、再度5kgの荷重を3秒間乗せた後、荷重を取り除き、完全に硬化膜積層フィルムを開いた。上記操作を繰り返し、折り曲げ部にクラックが発生する回数を折り曲げ回数とした。耐折れ性は5回以上であることが好ましい。
フレキシブル銅貼り積層板(電解銅箔の厚さ12μm、ポリイミドフィルムは株式会社カネカ製、商品名:アピカル25NPI、ポリイミド系接着剤で銅箔を接着している)上にライン幅/スペース幅=100μm/100μmの櫛形パターンを作製し、10容量%の硫酸水溶液中に1分間浸漬した後、純水で洗浄して銅箔の表面処理を行った。その後、上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で櫛形パターン上に、最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、試験片(絶縁膜付きプリント配線板)の作成を行った。そして、85℃、85%RHの環境試験機中で、試験片の両端子部分に100Vの直流電流を印加して、1,000時間後の試験片の絶縁抵抗値を測定した。絶縁膜の抵抗値は、1×108以上であることが好ましい。また、1,000時間後にマイグレーション、デンドライトなど外観変化の発生を目視にて観察した。観察結果を下記「○」、「△」または「×」で示す。
○:1,000時間後、マイグレーション、デンドライトなどの外観変化の発生がない
△:1,000時間後、僅かにマイグレーション、デンドライトなどの外観変化の発生がある
×:1,000時間後、顕著にマイグレーション、デンドライトなどの外観変化の発生がある。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さが75μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル75NPI)の表面に最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。得られた絶縁膜積層フィルムを、260℃で完全に溶解させた半田浴に、絶縁膜用樹脂組成物の絶縁膜が塗工してある面が接するように浮かべて10秒後に引き上げた。その操作を3回行い、フィルム表面の状態を観察した。観察結果を下記「○」または「×」で示す。
○:塗膜に異常がない
×:塗膜に膨れや剥がれなどの異常が発生する。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル25NPI)の表面に最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。フィルムの反りの高さの測定方法を説明するための模式図を図1に示す。図1に示すように、得られた絶縁膜積層フィルム(絶縁膜用樹脂組成物の絶縁膜を積層したポリイミドフィルム)1を面積50mm×50mmの正方形状に切り出して、平滑な台3の上に絶縁膜側が上面になるように置き、フィルム端部の反り高さ2を測定した。絶縁膜積層フィルム1の反り高さ2が小さい程、プリント配線板表面での応力が小さくなり、プリント配線板の反りも低下することになる。反り高さ2は、5mm以下であることが好ましい。尚、絶縁膜積層フィルム1が筒状に丸まる場合は「×」と判定した。
実施例1にて用いた合成例5の分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子に替えて、ポリメタクリル酸メチル系架橋ポリマー粒子(ガンツ化成株式会社製、商品名:ガンツパールGM−0801S、平均粒子径8μm)を用いて、実施例1〜7の方法と同様の方法で物性評価を行った。その結果を表2に記載する。
合成例2にて得られたバインダーポリマーである分子内にウレタン結合及びカルボキシル基を含有する樹脂60.0重量部、エポキシ樹脂22.5重量部(ジャパンエポキシレジン株式会社製、商品名:jER828)、メラミン2.5重量部(日産化学株式会社製、商品名:微粉メラミン)、コアシェル多層構造をもつ有機微粒子12.0重量部(ガンツ化成株式会社製、商品名:スタフィロイドAC−3816、平均粒子径0.5μm)を用いて、実施例1〜7の方法と同様の方法で物性評価を行った。その結果を表2に記載する。
<絶縁膜用樹脂組成物の調製>
合成例1〜4で得られた(A)バインダーポリマー1〜4に、合成例5で得られた(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子、(C)熱硬化性樹脂、(D)分子内にラジカル重合性基を有する化合物、(E)光重合開始剤、(F)リン系難燃剤、その他の成分、及び有機溶媒を添加して、実施例8〜13にかかる絶縁膜用樹脂組成物を作製した。それぞれの絶縁膜用樹脂組成物における構成原料の樹脂固形分での配合量及び原料の種類を表3に記載する。なお、表3中の溶媒である1,2−ビス(2−メトキシエトキシ)エタンは上記合成した樹脂溶液に含まれる溶剤も含めた全溶剤量である。絶縁膜用樹脂組成物は、先ず、一般的な攪拌翼のついた攪拌装置にて混合し、その後、3本ロールミルに2回通して、均一な溶液とした。グラインドメーターにて混合溶液中の絶縁膜用樹脂組成物の粒子径を測定したところ、いずれも10μm以下であった。混合溶液中の泡を脱泡装置にて完全に脱泡した後、下記評価を実施した。
<1>日産化学株式会社製 多官能エポキシ樹脂(トリグリシジルイソシアヌレート)の製品名
<2>クラリアントジャパン株式会社製 ホスフィン酸塩の製品名
<3>日産化学株式会社製 メラミンの製品名
<4>共栄社化学株式会社製 ブタジエン系消泡剤の製品名
<5>日立化成工業株式会社製 分子内にラジカル重合性基を有する化合物(EO変性ビスフェノールAジメタクリレート)の製品名
<6>日本化薬株式会社製 分子内にラジカル重合性基を有する化合物(カルボキシル基及び感光性基含有樹脂)の製品名 固形分濃度65%、固形分酸価98mgKOH/g
<7>BASFジャパン株式会社製 光重合開始剤の製品名。
実施例8〜13にかかる絶縁膜用樹脂組成物を、ベーカー式アプリケーターを用いて、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:25NPI)の表面に最終乾燥厚さが20μmになるように100mm×100mmの面積に流延・塗布し、80℃で20分間乾燥させた後、300mJ/cm2の積算露光量の紫外線を照射して露光した。次いで、30℃に加熱した1.0重量%の炭酸ナトリウム水溶液を用いて、1.0kgf/mm2の吐出圧で90秒間スプレー現像を行った。スプレー現像後、純水で十分洗浄して、150℃のオーブン中で30分間、加熱硬化させた。これにより、ポリイミドフィルム上に絶縁膜用樹脂組成物の絶縁膜(硬化膜)を形成して、絶縁膜積層フィルム(絶縁膜用樹脂フィルム)を作製した。
以下の項目について、得られた絶縁膜積層フィルムの評価を行った。評価結果を表4に記載する。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で得られた絶縁膜用樹脂組成物の絶縁膜の表面観察を行い、感光性を判定した。ただし、露光は、ライン幅/スペース幅=100μm/100μmのネガ型フォトマスクを置いて行った。判定結果を下記「○」または「×」で示す。
〇:ポリイミドフィルム表面に顕著な線太りまたは現像残渣が無く、ライン幅/スペース幅=100μm/100μmの感光パターンが描けている
×:ポリイミドフィルム表面にライン幅/スペース幅=100μm/100μmの感光パターンが描けていない。
実施例8〜13にかかる絶縁膜用樹脂組成物を、ベーカー式アプリケーターを用いて、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:25NPI)の表面に最終乾燥厚さが20μmになるように100mm×100mmの面積に流延・塗布し、80℃で20分間乾燥させ、溶媒乾燥後に塗膜を形成して、塗膜付きフィルムを作製した。塗膜のタック性の評価方法は、作製した溶媒乾燥後の塗膜付きフィルムを50mm×30mmの短冊に切り出して、塗膜を内側にして塗膜面同士を重ね合わせ、重ね合わせた部分に300gの荷重を3秒間のせた後、荷重を取り除き、塗膜面を引き剥がしたときの状態を観察した。観察結果を下記「○」、「△」または「×」で示す。
○:塗膜同士の貼り付きがなく、塗膜に貼り付き跡も残っていない
△:塗膜同士が少し貼り付き、塗膜に貼り付き跡が残っている
×:塗膜同士が完全に貼り付いて引き剥がせない。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル25NPI)の表面に最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。絶縁膜積層フィルムの耐折れ性の評価方法は、当該絶縁膜積層フィルムを50mm×10mmの短冊に切り出して、絶縁膜を外側にして25mmのところ(中央部)で180°に折り曲げ、折り曲げ部に5kgの荷重を3秒間のせた後、荷重を取り除き、折り曲げ部の頂点を顕微鏡で観察することによって行った。顕微鏡で観察した後、折り曲げ部を180°程度開いて、再度5kgの荷重を3秒間乗せた後、荷重を取り除き、完全に絶縁膜積層フィルムを開いた。上記操作を繰り返し、折り曲げ部にクラックが発生する回数を折り曲げ回数とした。耐折れ性は5回以上であることが好ましい。
フレキシブル銅貼り積層板(電解銅箔の厚さ12μm、ポリイミドフィルムは株式会社カネカ製、商品名:アピカル25NPI、ポリイミド系接着剤で銅箔を接着している)上にライン幅/スペース幅=100μm/100μmの櫛形パターンを作製し、10容量%の硫酸水溶液中に1分間浸漬した後、純水で洗浄して銅箔の表面処理を行った。その後、上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で櫛形パターン上に、最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、試験片(絶縁膜付きプリント配線板)の作成を行った。そして、85℃、85%RHの環境試験機中で、試験片の両端子部分に100Vの直流電流を印加して、1,000時間後の試験片の絶縁抵抗値を測定した。抵抗値は1×108以上であることが好ましい。また、1,000時間後にマイグレーション、デンドライトなど外観変化の発生を目視にて観察した。観察結果を下記「○」、「△」または「×」で示す。
○:1,000時間後、マイグレーション、デンドライトなどの外観変化の発生がない
△:1,000時間後、僅かにマイグレーション、デンドライトなどの外観変化の発生がある
×:1,000時間後、顕著にマイグレーション、デンドライトなどの外観変化の発生がある。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さが75μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル75NPI)の表面に最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。得られた絶縁膜積層フィルムを、260℃で完全に溶解させた半田浴に、絶縁膜用樹脂組成物の絶縁膜が塗工してある面が接するように浮かべて10秒後に引き上げた。その操作を3回行い、フィルム表面の状態を観察した。観察結果を下記「○」または「×」で示す。
○:塗膜に異常がない
×:塗膜に膨れや剥がれなどの異常が発生する。
上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さが25μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル25NPI)の表面に最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。フィルムの反りの高さの測定方法を説明するための模式図を図1に示す。図1に示すように、得られた絶縁膜積層フィルム(絶縁膜用樹脂組成物の絶縁膜を積層したポリイミドフィルム)1を面積50mm×50mmの正方形状に切り出して、平滑な台3の上に絶縁膜側が上面になるように置き、フィルム端部の反り高さ2を測定した。絶縁膜積層フィルム1の反り高さ2が小さい程、プリント配線板表面での応力が小さくなり、プリント配線板の反りも低下することになる。反り高さ2は5mm以下であることが好ましい。尚、絶縁膜積層フィルム1が筒状に丸まる場合は「×」と判定した。
プラスチック材料の燃焼性試験規格 UL94VTM に従い、以下のようにして燃焼性試験を行った。すなわち、上記<ポリイミドフィルム上への塗膜の作製>の項目に記載の方法と同様の方法で、基材としての厚さ25μmのポリイミドフィルム(株式会社カネカ製、商品名:アピカル25NPI)の両表面に、最終乾燥厚さが20μmの絶縁膜用樹脂組成物の絶縁膜を形成して、絶縁膜積層フィルムを作製した。作製した上記絶縁膜積層フィルムを幅50mm×長さ200mm×厚さ75μm(ポリイミドフィルムの厚さを含む)の寸法に20枚切り出し、それぞれフィルム端部から125mmの部分に標線を入れ、標線を外側にして直径約13mm×長さ200mmの筒状に丸めた。その後、標線よりも上の重ね合わせ部分(長さ(200−125=)75mmの部分)及びその上部(フィルム端部)に隙間が無いようにしてPI(ポリイミド)テープを貼って固定した。これにより、燃焼性試験用のサンプル(筒)を20本用意した。そのうちの10本は、(1)23℃/50%相対湿度で48時間処理し、残りの10本は、(2)70℃で168時間の処理後に、無水塩化カルシウム入りデシケーターで4時間以上冷却した。これらサンプルの上部(PIテープを貼った側)をクランプで止めて垂直に(吊り下げるようにして)固定し、サンプルの下部(PIテープを貼っていない側)にバーナーの炎を3秒間近づけて着火した。3秒間経過したらバーナーの炎を遠ざけて、着火したサンプルの炎や燃焼が何秒後に消えるかを測定した。測定結果を下記「○」または「×」で示す。
○:各条件((1),(2))につき、サンプルからバーナーの炎を遠ざけた後、10本とも最長で10秒以内に炎や燃焼が消えて自己消火し、かつ評線まで燃焼が達していない
×:各条件((1),(2))につき、サンプルからバーナーの炎を遠ざけた後、1本でも10秒以内に消火しない、または炎が評線以上のところまで達して燃焼する。
2 反り高さ
3 平滑な台
Claims (16)
- 少なくとも
(A)バインダーポリマー、及び
(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子
を含有することを特徴とする絶縁膜用樹脂組成物。 - 更に(C)熱硬化性樹脂を含有することを特徴とする請求項1に記載の絶縁膜用樹脂組成物。
- 更に(D)分子内にラジカル重合性基を有する化合物及び(E)光重合開始剤を含有することを特徴とする請求項1または2に記載の絶縁膜用樹脂組成物。
- 前記(A)バインダーポリマーが、下記(a1)〜(a3)からなる群から選ばれる少なくとも1種を有することを特徴とする請求項1〜3のいずれか1項に記載の絶縁膜用樹脂組成物。
(a1)ウレタン結合
(a2)カルボキシル基
(a3)イミド基 - 前記(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子の平均粒子径が、1μm以上、20μm以下であることを特徴とする請求項1〜4のいずれか1項に記載の絶縁膜用樹脂組成物。
- 前記(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子の吸油量が、50ml/100g以上であることを特徴とする請求項1〜5のいずれか1項に記載の絶縁膜用樹脂組成物。
- 前記(B)分子内にウレタン結合及びカーボネート骨格を有する架橋ポリマー粒子の配合量が、(A)バインダーポリマー100重量部に対して30重量部以上、100重量部以下であることを特徴とする請求項1〜6のいずれか1項に記載の絶縁膜用樹脂組成物。
- 更に(F)リン系難燃剤を含有することを特徴とする請求項1〜7のいずれか1項に記載の絶縁膜用樹脂組成物。
- 前記(F)リン系難燃剤が、ホスフィン酸塩であることを特徴とする請求項8に記載の絶縁膜用樹脂組成物。
- 前記(F)リン系難燃剤の配合量が、(A)バインダーポリマー100重量部に対して5重量部以上、100重量部以下であることを特徴とする請求項8または9に記載の絶縁膜用樹脂組成物。
- 請求項1〜10のいずれか1項に記載の絶縁膜用樹脂組成物を基材表面に塗布した後、乾燥して得られる絶縁膜用樹脂フィルム。
- 請求項11に記載の絶縁膜用樹脂フィルムを硬化させて得られる絶縁膜。
- 請求項12に記載の絶縁膜がプリント配線板に被覆してなる絶縁膜付きプリント配線板。
- 請求項1〜10のいずれか1項に記載の絶縁膜用樹脂組成物から得られることを特徴とする絶縁膜用樹脂フィルム。
- 請求項1〜10のいずれか1項に記載の絶縁膜用樹脂組成物から得られることを特徴とする絶縁膜。
- 請求項15に記載の絶縁膜がプリント配線板に被覆してなる絶縁膜付きプリント配線板。
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