JP2011116977A - 熱重合系開始剤システム及び接着剤組成物 - Google Patents
熱重合系開始剤システム及び接着剤組成物 Download PDFInfo
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- JP2011116977A JP2011116977A JP2010248599A JP2010248599A JP2011116977A JP 2011116977 A JP2011116977 A JP 2011116977A JP 2010248599 A JP2010248599 A JP 2010248599A JP 2010248599 A JP2010248599 A JP 2010248599A JP 2011116977 A JP2011116977 A JP 2011116977A
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- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- DCVWZWOEQMSMLR-UHFFFAOYSA-N silylperoxysilane Chemical compound [SiH3]OO[SiH3] DCVWZWOEQMSMLR-UHFFFAOYSA-N 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
[式(II)中、Raは水素、メチル基、アセチル基、メトキシカルボニル基、エトキシカルボニル基、ベンジルオキシカルボニル基、ベンゾイル基、フェノキシカルボニル基、9−フルオレニルメトキシカルボニル基のいずれかを、Rb、Rcは独立して水素、ハロゲン、C1〜C4のアルキル基のいずれかを、RdはC1〜C4のアルキル基を、Qはo−ニトロベンジル基、m−ニトロベンジル基、ジニトロベンジル基、トリニトロベンジル基、α−ナフチルメチル基、β−ナフチルメチル基のいずれかを示す。XはSbF6、AsF6、PF6、BF4のいずれかである。]
[式(III)中、Reは、水素原子、アルキル基、ハロゲン原子、カルボキシル基又はアルコキシカルボニル基を表し、Rfはアルキル基を表し、Rgは置換されていてもよいフェニル基又は置換されていてもよいナフチル基を表し、Xは、SbF6、AsF6、PF6又はBF6を表す。]
[式中、R1及びR2はそれぞれ独立に置換又は未置換のアリール基を示し、Y−はアニオン残基を示す。]
(2)上記Y−が、SbF6 −、[P(R6)a(F)6−a]−(式中、R6は水素原子の少なくとも一部がフッ素原子で置換されているアルキル基を示し、aは0〜5の整数を示す。aが2以上の整数である場合、複数存在するR6は、互いに同一であっても異なっていてもよい。)、B(C6F5)4 −又はC(CF3SO2)3 −である、上記(1)に記載の熱重合系開始剤システム。
(3)上記ラジカル重合開始剤が、有機過酸化物である、上記(1)又は(2)に記載の熱重合系開始剤システム。
(4)上記有機過酸化物の1分間半減期温度が、80〜170℃である、上記(3)に記載の熱重合系開始剤システム。
(5)カチオン重合性物質の硬化に使用される、上記(1)〜(4)のいずれかに記載の熱重合系開始剤システム。
(6)加熱による硬化に使用される、上記(1)〜(5)のいずれかに記載の熱重合系開始剤システム。
[式中、R1及びR2はそれぞれ独立に置換又は未置換のアリール基を示し、Y−はアニオン残基を示す。]
(8)上記Y−が、SbF6 −、[P(R6)a(F)6−a]−(式中、R6は水素原子の少なくとも一部がフッ素原子で置換されているアルキル基を示し、aは0〜5の整数を示す。aが2以上の整数である場合、複数存在するR6は、互いに同一であっても異なっていてもよい。)、B(C6F5)4 −又はC(CF3SO2)3 −である、上記(8)に記載の接着剤組成物。
(9)上記ラジカル重合開始剤が有機過酸化物である、上記(7)又は(8)に記載の接着剤組成物。
(10)上記有機過酸化物の1分間半減期温度が、80〜170℃である、上記(9)に記載の接着剤組成物。
(11)上記カチオン重合性物質は、エポキシ化合物、オキセタン化合物及びビニルエーテル化合物からなる群より選ばれる少なくとも一種を含有する、上記(7)〜(10)のいずれかに記載の接着剤組成物。
(12)(D)フィルム形成性ポリマーを更に含有する、上記(7)〜(11)のいずれかに記載の接着剤組成物。
(13)(E)導電性粒子を更に含有する、上記(7)〜(12)のいずれかに記載の接着剤組成物。
(14)異方導電性を有する、上記(13)に記載の接着剤組成物。
(15)回路接続用接着剤組成物として使用される、上記(7)〜(14)のいずれかに記載の接着剤組成物。
(16)加熱により硬化される、上記(7)〜(15)のいずれかに記載の接着剤組成物。
(17)上記(7)〜(16)のいずれかに記載の接着剤組成物をフィルム状にしてなる、フィルム状接着剤組成物。
本実施形態に係る開始剤システムは、(A)一般式(I)で表されるヨードニウム塩化合物(以下、場合により「(A)成分」という。)と、(B)ラジカル重合開始剤(以下、場合により「(B)成分」という。)と、を含有する。
本実施形態に係る接着剤組成物は、(A)一般式(I)で表されるヨードニウム塩化合物と、(B)ラジカル重合開始剤と、(C)カチオン重合性物質(以下、場合により「(C)成分」という。)と、を含有してなる。
(A)成分としてPhotoinitiator2074(ローディア社製品名、4−メチルフェニル[4−(1−メチルエチル)フェニル]ヨウドニウムテトラキス(ペンタフルオロフェニル)ボレート、(B)成分としてパーヘキサ25O(日油株式会社製品名、2,5−ジメチル−2,5−ジ(エチルヘキサノイルパーオキシ)ヘキサン、純度50%、1分間半減期温度119℃)、(C)成分としてグリシジルエーテル型エポキシ化合物YL980(ジャパンエポキシレジン株式会社製品名、ビスフェノールF型エポキシ樹脂)を用いた。バインダーとしてフェノキシ樹脂(YP−70、東都化成(株)製商品名)を用いた。また、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の金属を設けた平均粒径3μm、比重2.5の導電粒子を作成して用いた。
(B)成分として、パーヘキサ25OにかえてパーロイルL(日油株式会社製品名、ジラウロイルパーオキシド、純度98%、1分間半減期温度116℃)を用いた以外は、実施例1と同様な方法でフィルム状接着剤組成物を得た。表1に各成分の混合比を示す。
(C)成分として、YL980にかえて脂環式エポキシ化合物セキサロイドGT401(ダイセル化学工業株式会社製品名、エポキシ化ブタンテトラカルボン酸テトラキス−(3−シクロヘキセニルメチル)修飾ε−カプロラクトン)を用いた以外は、実施例2と同様な方法でフィルム状接着剤組成物を得た。表1に各成分の混合比を示す。
(C)成分として、YL980にかえてオキセタン化合物OXT−121(東亞合成株式会社製品名、1,4−ジ[(3−オキセタニル−n−ブトキシ)メチル]ベンゼン)を用いた以外は、実施例2と同様な方法でフィルム状接着剤組成物を得た。表1に各成分の混合比を示す。
(C)成分として、YL980とビニルエーテル化合物CHDVE(日本カーバイド工業株式会社製品名、シクロヘキサンジメタノールジビニルエーテル)とを併用した以外は実施例2と同様な方法でフィルム状接着剤組成物を得た。表1に各成分の混合比を示す。
(B)成分を使用しなかったこと以外は実施例2と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980にかえて脂環式エポキシ化合物セキサロイドGT401(ダイセル化学工業株式会社製品名、エポキシ化ブタンテトラカルボン酸テトラキス−(3−シクロヘキセニルメチル)修飾ε−カプロラクトン)を用いた以外は比較例1と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980にかえてオキセタン化合物OXT−121(東亞合成株式会社製品名、1,4−ジ[(3−オキセタニル−n−ブトキシ)メチル]ベンゼン)を用いた以外は比較例1と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980とビニルエーテル化合物CHDVE(日本カーバイド工業株式会社製品名、シクロヘキサンジメタノールジビニルエーテル)とを併用した以外は比較例1と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(A)成分を使用しなかったこと以外は実施例2と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980にかえて脂環式エポキシ化合物セキサロイドGT401(ダイセル化学工業株式会社製品名、エポキシ化ブタンテトラカルボン酸テトラキス−(3−シクロヘキセニルメチル)修飾ε−カプロラクトン)を用いた以外は比較例5と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980にかえてオキセタン化合物OXT−121(東亞合成株式会社製品名、1,4−ジ[(3−オキセタニル−n−ブトキシ)メチル]ベンゼン)を用いた以外は比較例5と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980とビニルエーテル化合物CHDVE(日本カーバイド工業株式会社製品名)とを併用した以外は比較例5と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(A)成分のPhotoinitiator2074にかえてサンエイドSI−60(三新化学工業株式会社製品名、4−ヒドロキシフェニルメチル−α−ナフチルメチルスルホニウムヘキサフルオロアンチモネート)を使用し、(B)成分を使用しなかったこと以外は、実施例2と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980にかえて脂環式エポキシ化合物セキサロイドGT401(ダイセル化学工業株式会社製品名、エポキシ化ブタンテトラカルボン酸テトラキス−(3−シクロヘキセニルメチル)修飾ε−カプロラクトン)を用いた以外は比較例9と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
(C)成分として、YL980にかえてオキセタン化合物OXT−121(東亞合成株式会社製品名、1,4−ジ[(3−オキセタニル−n−ブトキシ)メチル]ベンゼン)を用いた以外は比較例9と同様な方法でフィルム状接着剤組成物を得た。表2に各成分の混合比を示す。
成分Cとしてグリシジルエーテル型エポキシであるYL980を用いた実施例1、2および比較例1の示差走査熱量測定結果を図1に、成分Cとして脂環式エポキシであるGT401を用いた実施例3および比較例2の示差走査熱量測定結果を図2に、成分CとしてオキセタンであるOXT−121を用いた実施例4および比較例3の示差走査熱量測定結果を図3に、成分Cとしてグリシジルエーテル型エポキシであるYL980とビニルエーテルであるCHDVEを用いた実施例5および比較例4の示差走査熱量測定結果を図4に示す。
実施例1〜5、比較例1〜11のフィルム状接着剤組成物をホットプレート上で10秒間110〜160℃に加熱して硬化させた。赤外線吸収スペクトルにより、加熱前のエポキシ基、オキセタニル基、ビニル基のシグナル強度の面積と、加熱後のそれぞれのシグナル強度の面積との商を硬化率として求めた。実施例1〜5の結果を図5に、比較例1〜8の結果を図6に、比較例9〜11の結果を図7に、それぞれ示す。
実施例1〜5、比較例1〜11のフィルム状接着剤組成物を40℃の恒温装置に1〜5日間放置した。赤外線吸収スペクトルにより、放置後の硬化率を求めた。実施例1〜5の結果を図8に、比較例1〜8の結果を図9に,比較例9〜11の結果を図10に、それぞれ示す。
実施例1〜5及び比較例1〜11の各フィルム状接着剤組成物を、ガラス基板(コーニング#1737、外形38mm×28mm、厚さ0.5mm、表面にITO(酸化インジウム錫)配線パターン(パターン幅50μm、ピッチ50μm)を有するもの)に2×20mmの大きさでPET樹脂フィルムから転写した。ICチップ(外形1.7mm×17.2mm、厚さ0.55mm、バンプの大きさ50μm×50μm、バンプのピッチ50μm)を表3に示す実装条件(温度と時間)で、80MPa(バンプ面積換算)荷重をかけて加熱加圧して実装した。また、保存安定性試験後のフィルム状接着剤組成物も同様に実装した。
上記のようにして作製した接続体の隣接回路間の抵抗値(14端子測定した中の最大値)を測定した。得られた結果を表3に示す。
Claims (17)
- 前記Y−が、SbF6 −、[P(R6)a(F)6−a]−(式中、R6は水素原子の少なくとも一部がフッ素原子で置換されているアルキル基を示し、aは0〜5の整数を示す。aが2以上の整数である場合、複数存在するR6は、互いに同一であっても異なっていてもよい。)、B(C6F5)4 −又はC(CF3SO2)3 −である、請求項1に記載の熱重合系開始剤システム。
- 前記ラジカル重合開始剤が、有機過酸化物である、請求項1又は2に記載の熱重合系開始剤システム。
- 前記有機過酸化物の1分間半減期温度が、80〜170℃である、請求項3に記載の熱重合系開始剤システム。
- カチオン重合性物質の硬化に使用される、請求項1〜4のいずれか一項に記載の熱重合系開始剤システム。
- 加熱による硬化に使用される、請求項1〜5のいずれか一項に記載の熱重合系開始剤システム。
- 前記Y−が、SbF6 −、[P(R6)a(F)6−a]−(式中、R6は水素原子の少なくとも一部がフッ素原子で置換されているアルキル基を示し、aは0〜5の整数を示す。aが2以上の整数である場合、複数存在するR6は、互いに同一であっても異なっていてもよい。)、B(C6F5)4 −又はC(CF3SO2)3 −である、請求項7に記載の接着剤組成物。
- 前記ラジカル重合開始剤が、有機過酸化物である、請求項7又は8に記載の接着剤組成物。
- 前記有機過酸化物の1分間半減期温度が、80〜170℃である、請求項9に記載の接着剤組成物。
- 前記カチオン重合性物質は、エポキシ化合物、オキセタン化合物及びビニルエーテル化合物からなる群より選ばれる少なくとも一種を含有する、請求項7〜10のいずれか一項に記載の接着剤組成物。
- (D)フィルム形成性ポリマーを更に含有する、請求項7〜11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7〜12のいずれか一項に記載の接着剤組成物。
- 異方導電性を有する、請求項13に記載の接着剤組成物。
- 回路接続用接着剤組成物として使用される、請求項7〜14のいずれか一項に記載の接着剤組成物。
- 加熱により硬化される、請求項7〜15のいずれか一項に記載の接着剤組成物。
- 請求項7〜16のいずれか一項に記載の接着剤組成物をフィルム状にしてなる、フィルム状接着剤組成物。
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