JP2022063329A - 接着剤組成物及び接続構造体 - Google Patents
接着剤組成物及び接続構造体 Download PDFInfo
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical class C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
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- 239000010959 steel Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- VNJISVYSDHJQFR-UHFFFAOYSA-N tert-butyl 4,4-dimethylpentaneperoxoate Chemical compound CC(C)(C)CCC(=O)OOC(C)(C)C VNJISVYSDHJQFR-UHFFFAOYSA-N 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
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- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
Description
[式(A)中、R1、R5、R6、R7及びR8はそれぞれ独立に、水素原子又は炭素数1~18のアルキル基を示し、R2、R3及びR4はそれぞれ独立に、アリール基を示す。]
(測定条件)
装置:東ソー株式会社製 GPC-8020
検出器:東ソー株式会社製 RI-8020
カラム:日立化成株式会社製 Gelpack GL-A-160-S+GL-A150
試料濃度:120mg/3ml
溶媒:テトラヒドロフラン
注入量:60μl
圧力:30kgf/cm2
流量:1.00ml/min
(a)熱可塑性樹脂は、加熱により粘度の高い液状状態になって外力により自由に変形し、冷却し外力を取り除くとその形状を保ったままで硬くなり、この過程を繰り返し行える性質を持つ樹脂(高分子)をいう。また、(a)熱可塑性樹脂は、上記の性質を有する反応性官能基を有する樹脂(高分子)であってもよい。(a)熱可塑性樹脂のガラス転移温度(Tg)は、-30℃以上190℃以下が好ましく、-25℃以上170℃以下がより好ましく、-20℃以上150℃以下が更に好ましい。
(b)ラジカル重合性化合物は、ラジカル重合開始剤の作用でラジカル重合を生じる化合物をいうが、光又は熱等の活性化エネルギーを付与することでそれ自体ラジカルを生じる化合物であってもよい。(b)ラジカル重合性化合物としては、例えば、ビニル基、(メタ)アクリロイル基、アリル基、マレイミド基等の活性ラジカルによって重合する官能基を有する化合物を好適に使用可能である。
[式(N)中、R23及びR24はそれぞれ独立に水素原子又はメチル基を示し、R25はエチレン基又はプロピレン基を示し、R26は飽和脂肪族基又は飽和脂環式基を示し、R27は、エステル基を含有する飽和脂肪族基又は飽和脂環式基、若しくは、カーボネート基を含有する飽和脂肪族基又は飽和脂環式基を示し、kは1~40の整数を示す。なお、式(N)中、R25同士、R26同士はそれぞれ同一でも異なってもよい。]
[式(O)中、R28は(メタ)アクリロイルオキシ基を示し、R29は水素原子又はメチル基を示し、l及びmはそれぞれ独立に1~8の整数を示す。なお、式(O)中、R28同士、R29同士、l同士及びm同士はそれぞれ同一でも異なってもよい。]
(c)ラジカル重合開始剤としては、従来から知られている有機過酸化物及びアゾ化合物等、外部からのエネルギーの付与によりラジカルを発生する化合物を用いることができる。(c)ラジカル重合開始剤としては、安定性、反応性、相溶性の観点から、1分間半減期温度が90~175℃であり且つ重量平均分子量が180~1000の有機過酸化物が好ましい。1分間半減期温度がこの範囲にあることで、貯蔵安定性に更に優れ、ラジカル重合性も充分に高く、短時間で硬化できる。
(d)ホウ素を含有する塩(以下「(d)成分」という)は、下記一般式(A)で表される化合物である。(d)成分は、ボレート化合物と、ボレート化合物の対カチオンとしてアンモニウム化合物とを含んでいる。
[式(A)中、R1、R5、R6、R7及びR8はそれぞれ独立に、水素原子又は炭素数1~18のアルキル基を示し、R2、R3及びR4はそれぞれ独立に、アリール基を示す。R1、R5、R6、R7及びR8は、互いに同一であっても異なっていてもよい。R2、R3及びR4は、互いに同一であっても異なっていてもよい。]
(e)導電性粒子は、その全体又は表面に導電性を有する粒子であればよいが、接続端子を有する部材の接続に使用する場合は、接続端子間の距離よりも平均粒径が小さい粒子が好ましい。
本実施形態に係る接着剤組成物には、硬化速度の制御のため、及び、貯蔵安定性を更に向上させるために、安定化剤を添加することができる。このような安定化剤としては、特に制限なく公知の化合物を使用することができるが、ベンゾキノン及びハイドロキノン等のキノン誘導体;4-メトキシフェノール及び4-t-ブチルカテコール等のフェノール誘導体;2,2,6,6-テトラメチルピペリジン-1-オキシル及び4-ヒドロキシ-2,2,6,6-テトラメチルピペリジン-1-オキシル等のアミノキシル誘導体;テトラメチルピペリジルメタクリレート等のヒンダードアミン誘導体;などが好ましい。安定化剤は、1種を単独で又は2種以上を混合して用いることができる。
[式(R)中、R33、R34及びR35はそれぞれ独立に、水素原子、炭素数1~5のアルキル基、炭素数1~5のアルコキシ基、炭素数1~5のアルコキシカルボニル基又はアリール基を示し、R36は(メタ)アクリロイル基、ビニル基、イソシアナート基、イミダゾール基、メルカプト基、アミノ基、メチルアミノ基、ジメチルアミノ基、ベンジルアミノ基、フェニルアミノ基、シクロヘキシルアミノ基、モルホリノ基、ピペラジノ基、ウレイド基又はグリシジル基を示し、sは1~10の整数を示す。]
次に、上述した接着剤組成物を用いた接続構造体及びその製造方法について説明する。本実施形態によれば、第1の基板及び当該第1の基板の主面上に配置された第1の接続端子を有する第1の回路部材と、第2の基板及び当該第2の基板の主面上に配置された第2の接続端子を有する第2の回路部材との間に、接着剤組成物を介在させた状態で当該接着剤組成物を硬化させることにより、第1の接続端子及び第2の接続端子が電気的に接続した状態で第1の回路部材及び第2の回路部材を接着する、接続構造体の製造方法が提供される。また、本実施形態によれば、基板及び当該基板の主面上に配置された接続端子を有する太陽電池セルと、配線部材との間に、接着剤組成物を介在させた状態で当該接着剤組成物を硬化させることにより、接続端子及び配線部材が電気的に接続した状態で太陽電池セル及び配線部材を接着する、接続構造体の製造方法が提供される。
(ポリエステルウレタン樹脂の準備)
ポリエステルウレタン樹脂(東洋紡株式会社製、UR-4800(商品名)、重量平均分子量:32000、ガラス転移温度:106℃)をメチルエチルケトンとトルエンの1:1混合溶媒に溶解して樹脂分30質量%の混合溶媒溶解品を準備した。
フェノキシ樹脂(商品名:YP-50(新日鉄住金化学株式会社製)、重量平均分子量:60000、ガラス転移温度:80℃)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%の溶液を準備した。
(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有する還流冷却管、及び、窒素ガス導入管を備えた反応容器に、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)2500質量部(2.50mol)と、イソホロンジイソシアネート(シグマアルドリッチ社製)666質量部(3.00mol)とを3時間で均一に滴下し、反応容器に充分に窒素ガスを導入した後、70~75℃に加熱して反応させた。反応容器に、ハイドロキノンモノメチルエーテル(シグマアルドリッチ社製)0.53質量部と、ジブチルスズジラウレート(シグマアルドリッチ社製)5.53質量部とを添加した後、2-ヒドロキシエチルアクリレート(シグマアルドリッチ社製)238質量部(2.05mol)を加え、空気雰囲気下70℃で6時間反応させ、ウレタンアクリレート(UA1)を得た。ウレタンアクリレートの重量平均分子量は15000であった。
リン酸基を有するビニル化合物として、2-(メタ)アクリロイルオ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。
(テトラn-ブチルアンモニウムn-ブチルトリ(4-tert-ブチルフェニル)ボレート(TBA-BPB)の合成)
ホウ酸トリエチル4.38g(30.0mmol)をテトラヒドロフラン20mlに溶かした溶液に、窒素雰囲気下、n-ブチルリチウムの1.59Mヘキサン溶液18.8ml(30.0mmol)を-78~-70℃で加え、さらに室温で2時間撹拌させた。
上記反応液に、金属マグネシウム3.00g(123mmol)とヨウ素30mgとを加え、これに窒素雰囲気下、1-ブロモ-4-tert-ブチルベンゼン21.1g(100mmol)をテトラヒドロフラン60mlに溶かした溶液を、反応温度が67~72℃になるように滴下し、さらに30~50℃で2時間撹拌させることにより、反応を完結させた。
反応液が室温にまで下がった後、ジエチルエーテルを600ml加え、次いで水150mlを少しずつ加えていった。反応液を分液ロートに移液し、水240ml、0.2Mテトラn-ブチルアンモニウムブロマイド水溶液180ml、水240mlの順で洗浄後、濃縮した。残渣にジエチルエーテルを600ml加え、析出した固体を濾取し、白色固体の目的物(TBA-BPB、融点190℃)17.7g(収率83%)を得た。
金属マグネシウム1.00g(41.1mmol)にヨウ素10mgとテトラヒドロフラン10mlを加え、これに窒素雰囲気下、n-ブチルブロマイド4.11g(30mmol)をテトラヒドロフラン20mlに溶かした溶液を、反応温度が67~72℃になるように滴下し、さらに室温で2時間撹拌させた。これにホウ酸トリエチル4.38g(30.0mmol)を-78~-70℃で加え、さらに室温で2時間撹拌させた。
上記反応液に、金属マグネシウム3.00g(123mmol)とヨウ素30mgとを加え、これに窒素雰囲気下、1-ブロモ-4-メチルナフタレン22.1g(100mmol)をテトラヒドロフラン60mlに溶かした溶液を、反応温度が67~72℃になるように滴下し、さらに30~50℃で2時間撹拌させることにより、反応を完結させた。
反応液が室温にまで下がった後、酢酸エチルを600ml加え、次いで水150mlを少しずつ加えていった。反応液を分液ロートに移液し、水240ml、0.2Mテトラn-ブチルアンモニウムブロマイド水溶液180ml、水240mlの順で洗浄後、濃縮した。残渣にジエチルエーテルを600ml加え、析出した固体を濾取し、白色固体の目的物(TBA-MNB、融点175℃)17.0g(収率77%)を得た。
ホウ酸トリエチル4.38g(30.0mmol)をテトラヒドロフラン20mlに溶かした溶液に、窒素雰囲気下、n-ブチルリチウムの1.59Mヘキサン溶液18.8ml(30.0mmol)を-78~-70℃で加え、さらに室温で2時間撹拌させた。
上記反応液に、金属マグネシウム3.00g(123mmol)とヨウ素30mgとを加え、これに窒素雰囲気下、1-ブロモベンゼン15.7g(100mmol)をテトラヒドロフラン60mlに溶かした溶液を、反応温度が67~72℃になるように滴下し、さらに30~50℃で2時間撹拌させることにより、反応を完結させた。
反応液が室温にまで下がった後、ジエチルエーテルを600ml加え、次いで水150mlを少しずつ加えていった。反応液を分液ロートに移液し、水240ml、0.2Mテトラn-ブチルアンモニウムブロマイド水溶液180ml、水240mlの順で洗浄後、濃縮した。残渣にジエチルエーテルを600ml加え、析出した固体を濾取し、白色固体の目的物(TBA-PB、融点142℃)14.9g(収率89%)を得た。
アミン化合物として、N,N-ジメチルアニリン(略称:DMA、Aldrich社製)を準備した。
ジラウロイルパーオキサイド(商品名:パーロイルL、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た後、このニッケル層の外側に厚み0.02μmの金層を設けて、平均粒径10μm、比重2.5の導電性粒子を作製した。
(回路接続用接着剤の作製)
固形質量比で表1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、並びに、ホウ素化合物又はアミン化合物を配合し、さらに、接着剤成分(回路接続用接着剤における導電性粒子を除いた成分)の全体積を基準として導電性粒子を1.5体積%配合分散させて、回路接続用接着剤を得た。得られた回路接続用接着剤を、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のフィルム状回路接続用接着剤を得た。
実施例1~6及び比較例1~4のフィルム状回路接続用接着剤を、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の薄層を形成した厚み1.1mmのガラス(ITO、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、120℃、2MPaで10秒間加熱加圧して幅2mmにわたり接続し、接続構造体A(FPC/ITO)を作製した。この接続構造体Aの隣接回路間の抵抗値を、接続直後と、85℃、85%RHの恒温恒湿槽中に240時間保持した後(高温高湿試験後)とにおいて、マルチメータを用いて測定した。抵抗値は隣接回路間の抵抗37点の平均で示した。
実施例1~2及び比較例1~2のフィルム状回路接続用接着剤を、ガスバリア性容器内(旭化成パックス株式会社製、商品名:ポリフレックスバッグ飛竜、型番:N-9、材質:ナイロン・厚み15μm/PE・厚み60μm、サイズ:200mm×300mm)に入れ、ガスバリア性容器内の空気を除いた後、ヒートシーラーにて密封後、40℃雰囲気下に48時間放置した。上記雰囲気下に放置することによって、-10℃雰囲気下で5ヶ月間放置したことと同等とした。その後、実施例1~2及び比較例1~2のフィルム状回路接続用接着剤を、上記と同様のFPCとITOの薄層を形成したガラスとの間、及び、FPCとAgペーストの薄層を形成したPET基板との間にそれぞれ介在させた。これを、上記接続抵抗及び接着強度の測定の際と同じ方法及び条件で加熱圧着して接続構造体を作製した。この接続構造体の接続抵抗及び接着強度を上記と同様の方法で測定した。
Claims (15)
- R5、R6、R7及びR8はそれぞれ独立に、炭素数1~12のアルキル基を示す、請求項1に記載の接着剤組成物。
- R5、R6、R7及びR8はそれぞれ独立に、炭素数1~6のアルキル基を示す、請求項1に記載の接着剤組成物。
- 前記(b)ラジカル重合性化合物が、リン酸基を有するビニル化合物と、当該ビニル化合物以外のラジカル重合性化合物と、を含む、請求項1~3のいずれか一項に記載の接着剤組成物。
- 前記(d)ホウ素を含有する塩の融点が60℃以上300℃以下である、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、ブチラール樹脂、アクリル樹脂、ポリイミド樹脂及びポリアミド樹脂、並びに、酢酸ビニルを構造単位として有する共重合体からなる群より選ばれる少なくとも1種を含む、請求項1~5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、ポリエステルウレタン樹脂を含む、請求項1~5のいずれか一項に記載の接着剤組成物。
- (e)導電性粒子を更に含有する、請求項1~7のいずれか一項に記載の接着剤組成物。
- 第1の基板の主面上に配置された第1の接続端子と、第2の基板の主面上に配置された第2の接続端子とを電気的に接続するために用いられる、請求項1~8のいずれか一項に記載の接着剤組成物。
- 基板の主面上に配置された接続端子を有する太陽電池セルの当該接続端子と、配線部材とを電気的に接続するために用いられる、請求項1~8のいずれか一項に記載の接着剤組成物。
- 第1の基板及び当該第1の基板の主面上に配置された第1の接続端子を有する第1の回路部材と、
第2の基板及び当該第2の基板の主面上に配置された第2の接続端子を有する第2の回路部材と、
前記第1の回路部材及び前記第2の回路部材の間に配置された接続部材と、を備え、
前記接続部材が、請求項1~8のいずれか一項に記載の接着剤組成物の硬化物を含有し、
前記第1の接続端子及び前記第2の接続端子が電気的に接続されている、接続構造体。 - 前記第1の基板及び前記第2の基板の少なくとも一方が、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、請求項11に記載の接続構造体。
- 前記第1の基板及び前記第2の基板の少なくとも一方が、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種を含む基材から構成されている、請求項11又は12に記載の接続構造体。
- 前記第1の基板が、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種を含む基材から構成されており、
前記第2の基板が、ポリイミド樹脂及びポリエチレンテレフタレートからなる群より選ばれる少なくとも1種を含む基材から構成されている、請求項11又は12に記載の接続構造体。 - 基板及び当該基板の主面上に配置された接続端子を有する太陽電池セルと、
配線部材と、
前記太陽電池セル及び前記配線部材の間に配置された接続部材と、を備え、
前記接続部材が、請求項1~8のいずれか一項に記載の接着剤組成物の硬化物を含有し、
前記接続端子及び前記配線部材が電気的に接続されている、接続構造体。
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JP2011067950A (ja) * | 2008-01-25 | 2011-04-07 | Kyowa Hakko Chemical Co Ltd | 金属膜のパターン形成方法 |
JP2013057777A (ja) * | 2011-09-08 | 2013-03-28 | Tdk Corp | ホログラム記録用フォトポリマー組成物及びホログラム記録媒体 |
JP2013144793A (ja) * | 2011-12-16 | 2013-07-25 | Hitachi Chemical Co Ltd | 接着剤組成物、フィルム状接着剤、接着シート、接続構造体、及び、接続構造体の製造方法 |
JP2014133875A (ja) * | 2012-12-13 | 2014-07-24 | Three Bond Co Ltd | 硬化性組成物 |
JP2015117262A (ja) * | 2013-12-17 | 2015-06-25 | スリーボンドファインケミカル株式会社 | 一液硬化性組成物 |
US20150184032A1 (en) * | 2012-09-28 | 2015-07-02 | Fujifilm Corporation | Temporary adhesive for production of semiconductor device, and adhesive support and production method of semiconductor device using the same |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2011067950A (ja) * | 2008-01-25 | 2011-04-07 | Kyowa Hakko Chemical Co Ltd | 金属膜のパターン形成方法 |
JP2013057777A (ja) * | 2011-09-08 | 2013-03-28 | Tdk Corp | ホログラム記録用フォトポリマー組成物及びホログラム記録媒体 |
JP2013144793A (ja) * | 2011-12-16 | 2013-07-25 | Hitachi Chemical Co Ltd | 接着剤組成物、フィルム状接着剤、接着シート、接続構造体、及び、接続構造体の製造方法 |
US20150184032A1 (en) * | 2012-09-28 | 2015-07-02 | Fujifilm Corporation | Temporary adhesive for production of semiconductor device, and adhesive support and production method of semiconductor device using the same |
JP2014133875A (ja) * | 2012-12-13 | 2014-07-24 | Three Bond Co Ltd | 硬化性組成物 |
JP2015117262A (ja) * | 2013-12-17 | 2015-06-25 | スリーボンドファインケミカル株式会社 | 一液硬化性組成物 |
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