JP6130980B1 - ポリアミドイミド樹脂を用いた接着剤組成物 - Google Patents
ポリアミドイミド樹脂を用いた接着剤組成物 Download PDFInfo
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- JP6130980B1 JP6130980B1 JP2016575603A JP2016575603A JP6130980B1 JP 6130980 B1 JP6130980 B1 JP 6130980B1 JP 2016575603 A JP2016575603 A JP 2016575603A JP 2016575603 A JP2016575603 A JP 2016575603A JP 6130980 B1 JP6130980 B1 JP 6130980B1
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- Prior art keywords
- resin
- mass
- copper foil
- adhesive composition
- epoxy resin
- Prior art date
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- 239000011347 resin Substances 0.000 title claims abstract description 96
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- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 83
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 83
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000011889 copper foil Substances 0.000 claims abstract description 46
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 20
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
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- 239000010949 copper Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
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Abstract
Description
(1)ポリアミドイミド樹脂、エポキシ樹脂及びリン系難燃剤が配合され、かつ以下の(A)〜(F)の特徴を有する接着剤組成物:
(A)ポリアミドイミド樹脂60〜85質量部に対して、エポキシ樹脂が15〜40質量部配合されていること;
(B)ポリアミドイミド樹脂のガラス転移温度が250℃以上であること;
(C)ポリアミドイミド樹脂の酸価が50〜150mgKOH/gであること;
(D)エポキシ樹脂の性状が25℃において液状であること;
(E)ポリアミドイミド樹脂とエポキシ樹脂の合計100質量部に対して、リン系難燃剤が15〜60質量部配合されていること;及び
(F)リン系難燃剤中の50質量%以上が、フェナントレン型のホスフィン酸誘導体であること。
(2)前記ポリアミドイミド樹脂が、酸成分としてトリメリット酸無水物を含有することを特徴とする(1)に記載の接着剤組成物。
(3)銅箔とポリイミドフィルムを貼り合せるために使用されることを特徴とする(1)または(2)に記載の接着剤組成物。
(4)(1)〜(3)のいずれかに記載の接着剤組成物からなる接着剤層を使用したことを特徴とする接着剤層付き銅箔。
(5)Bステージ状態における前記接着剤層付き銅箔の接着剤層中の残留溶剤量が5.0〜16.0質量%であることを特徴とする(4)に記載の接着剤層付き銅箔。
(6)150℃以下のラミネート温度で貼り合せ可能であることを特徴とする(4)または(5)に記載の接着剤層付き銅箔。
(7)ポリイミドフィルムの両面にそれぞれ銅箔を接着した両面銅張り積層板であって、(4)〜(6)のいずれかに記載の接着剤層付き銅箔を使用したことを特徴とする両面銅張り積層板。
(8)(7)に記載の両面銅張り積層板を使用したことを特徴とするフレキシブルプリント配線板。
(a)ポリアミドイミド樹脂のガラス転移温度が250℃以上、好ましくは255℃以上、更に好ましくは260℃以上であること;及び
(b)ポリアミドイミド樹脂の酸価が50〜150mgKOH/g、好ましくは50〜130mgKOH/g、更に好ましくは60〜120mgKOH/gであること。
また、芳香族を有するジイソシアネートは全ジイソシアネート中で80mol%以上であることが好ましく、90mol%以上であることが好ましく、100mol%であっても差し支えない。また、芳香族を有するジアミンは、全ジアミン中で80mol%以上であることが好ましく、90mol%以上であることがより好ましく、100mol%であっても差し支えない。
本発明の接着剤組成物は、柔軟性、低反りはやや劣るものの、低温加工性、接着性、耐熱性、難燃性、電気絶縁性を同時に高いレベルで満足するため、特に両面銅張り積層板において銅箔とポリイミドフィルムを貼り合わせるために好適に使用することができる。
本発明の接着剤組成物は、柔軟性、低反りはやや劣るため、カバーレイおよび接着フィルムに好適に使用することはできない。
構造内に構造[I]を有するホスフィン酸誘導体の好適な例としては、以下のものが挙げられる。
上記のホスフィン酸誘導体のほかに、難燃性、半田耐熱性、ブリードアウトを損なわない範囲で50質量%未満で必要に応じ、他のリン化合物を単独または複数を組み合わせて用いても構わない。
接着剤層中の残留溶剤量は、以下のように100℃を基準とした250℃での質量減少率(銅箔質量は含まない)より算出する。
接着剤層中の残留溶剤量(%)=(250℃での接着剤層付き銅箔の質量−銅箔質量)/(100℃での接着剤層付き銅箔の質量−銅箔質量)×100
固形化したポリアミドイミド樹脂を、ポリマー濃度が0.5g/dlとなるようにN−メチル−2−ピロリドンに溶解した。得られた溶液の溶液粘度及び溶媒粘度を30℃で、ウベローデ型粘度管により測定して、下記の式に従って対数粘度を計算した。
対数粘度(dl/g)=[ln(V1/V2)]/V3
上記式中、V1は、ウベローデ型粘度管により測定した溶液粘度を示し、V2は、ウベローデ型粘度管により測定した溶媒粘度を示す。V1及びV2は、ポリマー溶液及び溶媒(N−メチル−2−ピロリドン)が粘度管のキャピラリーを通過する時間から求めた。また、V3は、ポリマー濃度(g/dl)である。
固形化したポリアミドイミド樹脂0.1gを、20mlのN−メチル−2−ピロリドンに溶解し、チモールフタレインを指示薬にしてKOHで滴定し、樹脂106g当たりのカルボキシル基当量を測定して酸価とした。
ポリアミドイミド樹脂溶液を銅箔の光沢面に塗布し、140℃3分間熱風乾燥機で乾燥させた後、250℃30分間窒素雰囲気下で乾燥させることにより、樹脂付き銅箔を得た。その後、銅箔をエッチングすることにより、厚み20μmのポリアミドイミド樹脂フィルムを作成した。このようにして作成したポリアミドイミド樹脂フィルムのガラス転移点を、TMA(熱機械分析装置)針進入法により荷重5g、昇温速度10℃/分の条件で測定した。
接着剤組成物の溶液を銅箔(JX日鉱日石製BHY 厚み18μm)の非光沢面に乾燥後の厚みが5μmとなるように塗布し、110℃3分間熱風乾燥機で乾燥させ、Bステージ状態のサンプルを得た。このBステージサンプルの接着剤塗布面とポリイミドフイルム(東レデュポン製カプトン100EN)とを真空プレスラミネート機を用いて、130℃、3MPa、30秒間減圧下で熱圧着させた。熱圧着後のサンプルにおいて、浮きや剥がれ等の貼り合せ不良のないものを○、浮きもしくは剥がれ等の貼り合せ不良のあったものを×とした。
接着剤組成物の溶液を銅箔(JX日鉱日石製BHY 厚み18μm)の非光沢面に乾燥後の厚みが5μmとなるように塗布し、110℃3分間熱風乾燥機で乾燥させ、Bステージ状態のサンプルを得た。このBステージサンプルの接着剤塗布面とポリイミドフイルム(東レデュポン製カプトン100EN)とを真空プレスラミネート機を用いて、130℃、3MPa、30秒間減圧下で熱圧着させた。その後、200℃で3時間加熱硬化させた。硬化後のサンプルを、引っ張り試験機(島津製オートグラフAG−X plus)を用いて25℃の雰囲気下で銅箔を180°の方向に50mm/minの速度で引き剥がし、接着強度を測定した。接着強度が0.7N/mm以上のものを○、0.7N/mm未満のものを×とした。
接着性の評価と同様に加熱硬化させたサンプルを作製し、20mm角に切断し、300℃の半田浴にポリイミド面を上にしてフロートさせた。膨れや剥がれのないものを○、膨れもしくは剥がれのあったものを×とした。
接着剤組成物の溶液をポリイミドフイルム(カネカ製アピカル12.5NPI)に乾燥後の厚みが20μmとなるように塗布し、140℃3分間熱風乾燥機で乾燥させ、Bステージ状態のサンプルを得た。このBステージサンプルの接着剤塗布面とポリイミドフイルム(カネカ製アピカル12.5NPI)とを真空プレスラミネート機を用いて、130℃、3MPa、30秒間減圧下で熱圧着させた。その後、200℃で3時間加熱硬化させた。硬化後のサンプルをUL−94VTM規格に準拠して、難燃性を評価した。VTM−0相当のものを○、VTM−0を満足しないものを×とした。
接着剤組成物の溶液をポリイミドフイルム(カネカ製アピカル12.5NPI)に乾燥後の厚みが20μmとなるように塗布し、140℃3分間熱風乾燥機で乾燥させ、Bステージ状態のサンプルを得た。このBステージサンプルの接着剤塗布面とL/S=50/50μmのくし型パターンに真空プレスラミネート機を用いて、160℃、3MPa、30秒間減圧下で熱圧着させた。その後、200℃で3時間加熱硬化させた。温度121℃、湿度100%の環境下、100Vの電圧を250時間印加した。250時間後の抵抗値が1×109Ω以上でありデンドライトのないものを◎、250時間後の抵抗値が1×108Ω以上1×109Ω未満でありデンドライトのないものを○、250時間後の抵抗値が1×108Ω未満もしくはデンドライトが発生しているものを×とした。
表1に示す原料の樹脂組成(mol%)で、ポリアミドイミド樹脂の重合を行った。具体的には、以下のように重合を行った。
撹拌機、冷却管、窒素導入管および温度計を備えた4つ口のセパラブルフラスコに、無水トリメリット酸192.13g(1.00mol)、4,4′−ジフェニルメタンジイソシアネート217.73g(0.87mol)および脱炭酸後の樹脂分の濃度が40重量%となるようN−メチル−2−ピロリドン482.78gを加え、窒素下で100℃まで昇温して2時間反応させ、さらに150℃に昇温して5時間反応させた。その後、樹脂分の濃度が35重量%となるようN−メチル−2−ピロリドン114.95gを加えて希釈し、ポリアミドイミド樹脂1の溶液を得た。また、他のポリアミドイミド樹脂2〜4においても表1に示す原料の樹脂組成で上記と同様の手順で樹脂の重合を行い、溶液を得た。
撹拌機、冷却管、窒素導入管および温度計を備えた4つ口のセパラブルフラスコに、無水トリメリット酸192.13g(1.00mol)、4,4′−ジフェニルメタンジイソシアネート237.75g(0.95mol)および脱炭酸後の樹脂分の濃度が35重量%となるようN−メチル−2−ピロリドン634.91gを加え、窒素下で100℃まで昇温して2時間反応させ、さらに150℃に昇温して5時間反応させた。その後、樹脂分の濃度が30重量%となるようN−メチル−2−ピロリドン162.89gを加えて希釈し、ポリアミドイミド樹脂5の溶液を得た。
撹拌機、冷却管、窒素導入管および温度計を備えた4つ口のセパラブルフラスコに、無水トリメリット酸192.13g(1.00mol)、o−トリジンジイソシアネート211.42g(0.80mol)、トリレンジイソシアネート34.83g(0.20mol)、および脱炭酸後の樹脂分の濃度が35重量%となるようN−メチル−2−ピロリドン650.72gを加え、窒素下で100℃まで昇温して2時間反応させ、さらに150℃に昇温して5時間反応させた。その後、樹脂分の濃度が20重量%となるようN−メチル−2−ピロリドン750.83gを加えて希釈し、ポリアミドイミド樹脂6の溶液を得た。
撹拌機、冷却管、窒素導入管および温度計を備えた4つ口のセパラブルフラスコに、無水トリメリット酸180.60g(0.94mol)、4,4′−ジフェニルメタンジイソシアネート225.23g(0.90mol)、両末端カルボキシル基変性アクリロニトリルブタジエンゴム(分子量3500)210.00g(0.06mol)および脱炭酸後の樹脂分の濃度が40重量%となるようN,N−ジメチルアセトアミド804.95gを加え、窒素下で100℃まで昇温して2時間反応させ、さらに150℃に昇温して5時間反応させた。その後、樹脂分の濃度が30重量%となるようN,N−ジメチルアセトアミド447.20gを加えて希釈し、ポリアミドイミド樹脂7の溶液を得た。また、他のポリアミドイミド樹脂8においても表1に示す原料の樹脂組成で上記と同様の手順で樹脂の重合を行い、溶液を得た。
表2に示す接着剤配合(固形分(質量%))に従って実施例1〜11及び比較例1〜9の接着剤組成物のN−メチル−2−ピロリドン溶液及びN,N−ジメチルアセトアミド溶液を作製し、上記の特性の評価を行った。
Claims (8)
- ポリアミドイミド樹脂、エポキシ樹脂及びリン系難燃剤が配合され、かつ以下の(A)〜(F)の特徴を有する接着剤組成物:
(A)ポリアミドイミド樹脂60〜85質量部に対して、エポキシ樹脂が15〜40質量部配合されていること;
(B)ポリアミドイミド樹脂のガラス転移温度が250℃以上であること;
(C)ポリアミドイミド樹脂の酸価が50〜150mgKOH/gであること;
(D)エポキシ樹脂の性状が25℃において液状であること;
(E)ポリアミドイミド樹脂とエポキシ樹脂の合計100質量部に対して、リン系難燃剤が15〜60質量部配合されていること;及び
(F)リン系難燃剤中の50質量%以上が、フェナントレン型のホスフィン酸誘導体であること。 - 前記ポリアミドイミド樹脂が、酸成分としてトリメリット酸無水物を含有することを特徴とする請求項1に記載の接着剤組成物。
- 銅箔とポリイミドフィルムを貼り合せるために使用されることを特徴とする請求項1または2に記載の接着剤組成物。
- 請求項1〜3のいずれかに記載の接着剤組成物からなる接着剤層を使用したことを特徴とする接着剤層付き銅箔。
- Bステージ状態における前記接着剤層付き銅箔の接着剤層中の残留溶剤量が5.0〜16.0質量%であることを特徴とする請求項4に記載の接着剤層付き銅箔。
- 150℃以下のラミネート温度で貼り合せ可能であることを特徴とする請求項4または5に記載の接着剤層付き銅箔。
- ポリイミドフィルムの両面にそれぞれ銅箔を接着した両面銅張り積層板であって、請求項4〜6のいずれかに記載の接着剤層付き銅箔を使用したことを特徴とする両面銅張り積層板。
- 請求項7に記載の両面銅張り積層板を使用したことを特徴とするフレキシブルプリント配線板。
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JP2010116443A (ja) * | 2008-11-11 | 2010-05-27 | Kaneka Corp | 接着フィルムならびにフレキシブル金属張積層板 |
WO2012105558A1 (ja) * | 2011-02-01 | 2012-08-09 | Dic株式会社 | 熱硬化型樹脂組成物、その硬化物およびプリント配線板用層間接着フィルム |
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JP2010116443A (ja) * | 2008-11-11 | 2010-05-27 | Kaneka Corp | 接着フィルムならびにフレキシブル金属張積層板 |
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