JP5454578B2 - 接着剤組成物、接続構造体、接続構造体の製造方法及び接着剤組成物の応用 - Google Patents
接着剤組成物、接続構造体、接続構造体の製造方法及び接着剤組成物の応用 Download PDFInfo
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- JP5454578B2 JP5454578B2 JP2011525059A JP2011525059A JP5454578B2 JP 5454578 B2 JP5454578 B2 JP 5454578B2 JP 2011525059 A JP2011525059 A JP 2011525059A JP 2011525059 A JP2011525059 A JP 2011525059A JP 5454578 B2 JP5454578 B2 JP 5454578B2
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- acrylate
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- urethane
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- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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Description
破断伸び(%)=(L−L0)/L0×100 …(1)
本発明の第1の実施形態に係る接着剤組成物は、主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、接着剤組成物は、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、(c)ラジカル重合開始剤、及び、(d)リン酸基を有するビニル化合物を含有し、(b)ラジカル重合性化合物が20〜40mN/mの臨界表面張力を有するウレタン(メタ)アクリレートを含むことを特徴とするものである。
また、本発明の第2実施形態に係る接着剤組成物は、主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、及び、(c)ラジカル重合開始剤を含有し、(b)ラジカル重合性化合物がウレタン(メタ)アクリレートを含有し、破断伸びが300〜500%であることを特徴とするものである。
(ポリエステルウレタンの準備)
ポリエステルウレタン樹脂(東洋紡株式会社製、UR−8200(商品名))は、樹脂分30質量%のメチルエチルケトンとトルエンの1:1混合溶媒溶解品を用いた。
フェノキシ樹脂(東都化成株式会社製、YP−50(商品名))は樹脂40質量部を、メチルエチルケトン60質量部に溶解して、固形分40質量%の溶液とした。
エチレン−酢酸ビニル共重合体(三井デュポンポリケミカルズ製、EV40W(商品名))は樹脂分30質量%のトルエン溶解品を用いた。
(ウレタンアクリレート(UA1)の合成)
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2−ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリ(1,6−ヘキサンジオールカーボネート)(商品名:デュラノール T5652、旭化成ケミカルズ株式会社製)2000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70〜75℃に加熱し、水素添加ジフェルメタンジイソシアネート(商品名:VESTANAT H12MD、Degussa社製)787質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後11時間反応させ、IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA1)の臨界表面張力は24mN/m、重量平均分子量が13500、粘度2500Pa・sであった。
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2−ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリ(1,6−ヘキサンジオールカーボネート)(商品名:デュラノール T5652、旭化成ケミカルズ株式会社製)1000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70〜75℃に加熱し、水素添加ジフェルメタンジイソシアネート(商品名:VESTANAT H12MD、Degussa社製)787質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後13時間反応させ、IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA2)の臨界表面張力は23mN/m、重量平均分子量が15500、粘度4100Pa・sであった。
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2−ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量2000のポリカプロラクトンジオール(商品名:プラクセル220、ダイセル化学工業株式会社製)4000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70〜75℃に加熱し、イソホロンジイソシアネート(Aldrich株式会社製)666質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後12時間反応させ、IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA3)の臨界表面張力は27mN/m、重量平均分子量は13800、粘度650Pa・sであった。
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に、3−メチル−1,5−ペンタンジオール1650質量部(14モル)とセバシン酸2023質量部(10モル)を反応器に仕込み、常圧下、充分に窒素ガスを導入した後、約170℃で生成する水を系外に留去しながらエステル化反応を行った。ポリエステルの酸価が0.3mgKOH/g以下になった時点で真空ポンプにより徐々に真空度を上げ、反応を完結させた。このようにして得られたポリエステルジオールは数平均分子量1000を有していた。
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に2−ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリテトラメチレンエーテルグリコール(商品名:保土谷化学工業株式会社製、TG1000)2000質量部(2.00モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70〜75℃に加熱し、イソホロンジイソシアネート(Aldrich株式会社製)666質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後13時間反応させた。IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA5)の臨界表面張力は17mN/m、重量平均分子量が14500、粘度2900Pa・sであった。
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に、3−メチル−1,5−ペンタンジオール1650質量部(14モル)とセバシン酸2023質量部(10モル)を反応器に仕込み、常圧下、充分に窒素ガスを導入した後、約170℃で生成する水を系外に留去しながらエステル化反応を行った。ポリエステルの酸価が0.3mgKOH/g以下になった時点で真空ポンプにより徐々に真空度を上げ、反応を完結させた。このようにして得られたポリエステルジオールは数平均分子量1000を有していた。
攪拌機、温度計、塩化カルシウム乾燥管を備えた還流冷却管、窒素ガス導入管を備えた反応容器に、2−ヒドロキシエチルアクリレート(Aldrich株式会社製)238質量部(2.05モル)、ハイドロキノンモノメチルエーテル(Aldrich株式会社製)0.53質量部、数平均分子量1000のポリテトラメチレンエーテルグリコール(商品名:保土谷化学工業株式会社製、TG1000)2500質量部(2.50モル)、ジブチルスズジラウレート(Aldrich株式会社製)5.53質量部を投入した。充分に窒素ガスを導入した後、70〜75℃に加熱し、イソホロンジイソシアネート(Aldrich株式会社製)666質量部(3.00モル)を3時間で均一に滴下し、反応させた。滴下完了後15時間反応させた。IR測定によりイソシアネートが消失したことを確認して反応を終了し、ウレタンアクリレートを得た。得られたウレタンアクリレート(UA7)の臨界表面張力は16mN/m、重量平均分子量が20400、粘度3500Pa・sであった。
イソシアヌル酸変性2官能アクリレート(東亞合成株式会社製、M−215(商品名)を準備した。
2−(メタ)アクリロイロキシエチルホスフェート(商品名:ライトエステルP−2M、共栄社化学株式会社製)を準備した。
ラジカル重合開始剤としてジベンゾイルパーオキサイド(商品名:ナイパーBW、日油株式会社製)を準備した。
(導電性粒子の作製)
ポリスチレンを核とする粒子の表面に、厚み0.2μmのニッケル層を設け、このニッケル層の外側に、厚み0.02μmの金層を設け、平均粒径10μm、比重2.5の導電性粒子を作製した。
固形質量比で表2に示すように熱可塑性樹脂、ラジカル重合性化合物及びラジカル重合開始剤を配合し、さらに導電性粒子を1.5体積%配合分散させ、接着剤組成物を得た。得られた接着剤組成物を、塗工装置を用いて厚み80μmのフッ素樹脂フィルム上に塗布し、70℃、10分の熱風乾燥によって接着剤層の厚みが20μmのフィルム状接着剤組成物を得た。
実施例1〜12及び比較例1〜5のフィルム状接着剤組成物を、ポリイミドフィルム上にライン幅25μm、ピッチ50μm、厚み8μmの銅回路を500本有するフレキシブル回路板(FPC)と、0.2μmのITOの薄層を形成したガラス(厚み1.1mm、表面抵抗20Ω/□)との間に介在させた。これを、熱圧着装置(加熱方式:コンスタントヒート型、東レエンジニアリング社製)を用いて、160℃、3MPaで10秒間加熱加圧して幅2mmにわたり接続し、接続体を作製した。この接続体の隣接回路間の抵抗値を、接着直後と、85℃、85%RHの高温高湿槽中に240時間保持した後(試験後)にマルチメータで測定した。抵抗値は隣接回路間の抵抗37点の平均で示した。
Claims (12)
- 主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材とを接続するための接着剤組成物であって、
前記接着剤組成物は、(a)熱可塑性樹脂、(b)ラジカル重合性化合物、及び、(c)ラジカル重合開始剤を含有し、
前記(b)ラジカル重合性化合物がウレタン(メタ)アクリレートを含み、
破断伸びが300〜500%である、接着剤組成物。 - (d)リン酸基を有するビニル化合物をさらに含有する、請求項1記載の接着剤組成物。
- 前記ウレタン(メタ)アクリレートの重量平均分子量が10000以上25000未満である、請求項1又は2記載の接着剤組成物。
- 前記ウレタン(メタ)アクリレートは、脂肪族系ジイソシアネート及び脂肪族ジオールの縮合反応により得られるウレタン(メタ)アクリレートであり、前記脂肪族ジオールがポリカーボネートジオール類である、請求項1〜3のいずれか一項に記載の接着剤組成物。
- 200℃における貯蔵弾性率が0.5〜5MPaである、請求項1〜4のいずれか一項に記載の接着剤組成物。
- 前記(a)熱可塑性樹脂が、フェノキシ樹脂、ポリウレタン樹脂、ポリエステルウレタン樹脂、ブチラール樹脂、アクリル樹脂、及び、ポリイミド樹脂からなる群より選ばれる少なくとも1種を含有する、請求項1〜5のいずれか一項に記載の接着剤組成物。
- (e)導電性粒子をさらに含有する、請求項1〜6のいずれか一項に記載の接着剤組成物。
- 前記接着剤組成物がフィルム状である、請求項1〜7のいずれか一項に記載の接着剤組成物。
- 請求項7に記載の接着剤組成物を含有する、異方導電性接着剤。
- 主面上に第一の接続端子を有する第一の回路部材と、主面上に第二の接続端子を有する第二の回路部材と、接続部材と、を備える回路部材の接続構造体であって、
前記第一の接続端子及び前記第二の接続端子が対向するように、前記第一の回路部材及び前記第二の回路部材が前記接続部材を介して配置されるとともに、前記第一の接続端子及び前記第二の接続端子が電気的に接続されており、
前記接続部材は、請求項1〜8のいずれか一項に記載の接着剤組成物又は請求項9記載の異方導電性接着剤の硬化物であり、
前記第一の回路部材及び/又は前記第二の回路部材が、ガラス転移温度が200℃以下の熱可塑性樹脂を含む基材から構成されている、回路部材の接続構造体。 - 前記ガラス転移温度が200℃以下の熱可塑性樹脂は、ポリエチレンテレフタレート、ポリカーボネート及びポリエチレンナフタレートからなる群より選ばれる少なくとも1種である、請求項10記載の回路部材の接続構造体。
- 前記第一の回路部材又は前記第二の回路部材のうち一方の回路部材が、ポリエチレンテレフタレート、ポリカーボネート及びポリエチレンナフタレートからなる群より選ばれる少なくとも1種を含有する基材から構成され、
前記第一の回路部材又は第二の回路部材のうちもう一方の回路部材が、ポリイミド樹脂である、請求項10又は11記載の回路部材の接続構造体。
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JP2010153882A (ja) * | 2010-01-27 | 2010-07-08 | Hitachi Chem Co Ltd | 回路接続材料、回路部材の接続構造及び回路部材の接続方法。 |
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CN103351838A (zh) | 2013-10-16 |
WO2012014563A1 (ja) | 2012-02-02 |
TWI445789B (zh) | 2014-07-21 |
CN102449095B (zh) | 2016-06-01 |
KR20130042018A (ko) | 2013-04-25 |
TW201204797A (en) | 2012-02-01 |
KR20130143673A (ko) | 2013-12-31 |
KR20120068751A (ko) | 2012-06-27 |
JPWO2012014563A1 (ja) | 2013-09-12 |
CN102449095A (zh) | 2012-05-09 |
KR101385422B1 (ko) | 2014-04-14 |
CN105860910A (zh) | 2016-08-17 |
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