JP5598373B2 - 硬化性樹脂組成物、その硬化物、プリント配線基板用樹脂組成物、プリント配線基板、フレキシブル配線基板用樹脂組成物、半導体封止材料用樹脂組成物、及びビルドアップ基板用層間絶縁材料用樹脂組成物 - Google Patents
硬化性樹脂組成物、その硬化物、プリント配線基板用樹脂組成物、プリント配線基板、フレキシブル配線基板用樹脂組成物、半導体封止材料用樹脂組成物、及びビルドアップ基板用層間絶縁材料用樹脂組成物 Download PDFInfo
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- JP5598373B2 JP5598373B2 JP2011035769A JP2011035769A JP5598373B2 JP 5598373 B2 JP5598373 B2 JP 5598373B2 JP 2011035769 A JP2011035769 A JP 2011035769A JP 2011035769 A JP2011035769 A JP 2011035769A JP 5598373 B2 JP5598373 B2 JP 5598373B2
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- 238000005476 soldering Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 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
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-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
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- Reinforced Plastic Materials (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Description
(式中、X1及びX2は、それぞれ独立的に水素原子、又は炭素原子数1〜4のアルキル基であり、Aは水素原子又は水酸基である。)で表されるリン原子含有化合物(C)を必須成分とすることを特徴とする硬化性樹脂組成物に関する。
無水メチルナジック酸、ヘキサヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸等が挙げられ、フェノール系化合物としては、フェノールノボラック樹脂、クレゾールノボラック樹脂、芳香族炭化水素ホルムアルデヒド樹脂変性フェノール樹脂、ジシクロペンタジエンフェノール付加型樹脂、フェノールアラルキル樹脂(ザイロック樹脂)、ナフトールアラルキル樹脂、トリメチロールメタン樹脂、テトラフェニロールエタン樹脂、ナフトールノボラック樹脂、ナフトール−フェノール共縮ノボラック樹脂、ナフトール−クレゾール共縮ノボラック樹脂、ビフェニル変性フェノール樹脂(ビスメチレン基でフェノール核が連結された多価フェノール化合物)、ビフェニル変性ナフトール樹脂(ビスメチレン基でフェノール核が連結された多価ナフトール化合物)、アルコキシ基含有芳香環変性ノボラック樹脂(ホルムアルデヒドでフェノール核及びアルコキシ基含有芳香環が連結された多価フェノール化合物)、アミノトリアジン変性フェノール樹脂(フェノール骨格、トリアジン環及び1級アミノ基を分子構造中に有する化合物)等の多価フェノール化合物が挙げられる。
(式中、R’1、R’2、R’3は、アミノ基、アルキル基、フェニル基、ヒドロキシル基、ヒドロキシルアルキル基、エーテル基、エステル基、酸基、不飽和基、シアノ基のいずれかを表わす。)
で表される化合物又はイソシアヌル酸が好ましい。
(下記構造式で表される中間体Aの合成)
コンデンサー、窒素導入管つきの乾燥したフラスコにリチウムワイヤー3.0g(0.432mol)とジエチルエーテル75mlを仕込み、撹拌する。この溶液にブロモベンゼン31.4g(0.200mol)を滴下ポンプで1時間かけて連続的に添加し、リチウムワイヤーが完全に溶解するまで反応させた。さらに24時間撹拌を継続した後、乾燥THF25mlを添加してフィルターを通過させ残留するリチウムを除去し、目的の化合物(フェニルリチウム)を得た。ヨウ素化したサンプルのGC測定にて目的物へのフルコンバージョン及びビフェニルが存在していないことを確認した。
MS(EI):260 M+(C18H13P+,ベースピーク),288,183(C12H8P+).31P NMR(CDClCl3):δ=−10.1ppm(Lit. value −11.6)
続いてコンデンサー、窒素導入管つきの乾燥したフラスコに上記中間体A17.86g(68.7mmol)と乾燥THF40mlを仕込み、25℃の水浴中で撹拌する。この溶液に金属リチウム1.1g(158mmol,2.3当量)を3分割して添加し、金属リチウムが完全に溶解したことを確認した後、更に10時間反応させた。GC測定にて目的物である中間体Bへのフルコンバージョンを確認した。
(下記構造式で表される中間体Cの合成)
得られた中間体Bに−10℃で乾燥THFと水の1:1混合溶液15mlを加え冷却し、更に、酢酸を無色透明の混合物が発生するまで添加した。水層を棄却した後、有機層を10mlのNa2SO4にて洗浄、乾燥させた。得られた化合物をろ過、10-2mbar/120℃で乾燥させ、無色透明の中間体C7.5g(40.7mmol,収率59%)を得た。
(下記構造式で表されるリン原子含有化合物(P1)の合成)
コンデンサー、撹拌子、滴下漏斗つきの乾燥したフラスコに水50mlと30%過酸化水素水溶液20mlを仕込み均一化した。さらに、この溶液中に前記中間体Cを添加し、酸化反応させた。反応完結後、この混合物を30分かけて100℃に昇温し、その後25℃に冷却し、NaOH8gを添加した。30分間撹拌した後、氷浴中で0℃に冷却し、化合物のNa塩の白色小板状結晶をろ過して分取した。この固体を50℃、50mlの水に溶解させ、10%塩酸水溶液40mlを60℃で添加し、pHが酸性サイドになっていることを確認した。固形分をろ過し、20mlの冷水で洗浄し、24時間空気乾燥させ、目的とするリン原子含有化合物(P1)6.5g(30.1mmol、収率74質量%)を得た。リン原子含有化合物(P1)のリン含有量は14.4質量%であった。得られたリン原子含有化合物(P1)のNMR分析結果を下記に示す。
δ(1H)=7.42−7.80(m, 6H), 8.0−8.1 (m, 2H);
δ(13C)=221.8(d),228.1 (d), 129.8 (d), 131.6 (d), 133.5, 139.5 (d);
δ(31P)=36.6ppm,
表1に示した配合に従い、下記の方法でエポキシ樹脂組成物を調整し、次いで、下記の条件で硬化させて、積層板を試作し、各種評価を行った。結果を表2に示す。
下記表2記載の組成に従い、エポキシ樹脂、硬化剤及びその他の各成分を配合した後、最終的に組成物の不揮発分(N.V.)を58質量%となるように調整した。
基材:100μm;日東紡績株式会社製ガラスクロス「#2116」
プライ数:6
プリプレグ化条件:160℃/2分
銅箔:18μm;日鉱金属株式会社製 JTC箔
硬化条件:200℃、40kg/cm2で1.5時間
成型後板厚:0.8mm
ガラス転移温度:エッチング処理を施し銅箔除去した後、TMA法(圧縮荷重法)にて測定。昇温スピード10℃/分。
N−690:クレゾールノボラック型エポキシ樹脂(DIC(株)製「エピクロンN−690」、エポキシ当量:214g/eq.)
HP−7200H:ジシクロペンタジエン型エポキシ樹脂(DIC(株)製「エピクロンHP−7200H」、エポキシ当量:279g/eq.)
P1:合成例1で得られたリン原子含有化合物(P1)
HCA:9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキサイド
TD−2090:フェノールノボラック型フェノール樹脂(DIC(株)製「TD−2090」、水酸基当量105g/eq)
2E4MZ:2−エチル−4−メチルイミダゾール
Claims (11)
- 前記硬化剤(B)が、活性水素又は酸無水物基を有するものであって、かつ、エポキシ樹脂(A)と硬化剤(B)との配合比率が、エポキシ樹脂(A)のエポキシ基の合計1当量に対して、硬化剤(B)中の活性水素又は酸無水物基が0.7〜1.5当量となる割合である請求項1記載の硬化性樹脂組成物。
- 前記リン原子含有化合物(C)が、前記(A)、(B)、及び(C)の合計質量中のリン原子の質量割合が1.0〜4.0質量%となる割合で配合されている請求項1又は2記載の硬化性樹脂組成物。
- 前記(A)〜(C)の各成分に加え、更に硬化促進剤(D)を配合する請求項1記載の硬化性樹脂組成物。
- 前記(A)〜(D)の各成分に加え、更に、有機溶剤(E)を含有する請求項4記載の硬化性樹脂組成物。
- 請求項1〜5の何れか1つに記載の硬化性樹脂組成物を硬化させてなる硬化物。
- 請求項5記載の組成物からなるプリント配線基板用樹脂組成物。
- 請求項5記載の組成物からなるフレキシブル配線基板用樹脂組成物。
- 請求項5記載の組成物をガラス基材に含浸、次いで硬化させてなるプリント配線基板。
- 請求項4記載の組成物に加え、更に無機充填剤を含有する半導体封止材料用樹脂組成物。
- 請求項4記載の組成物からなるビルドアップ基板用層間絶縁材料用樹脂組成物。
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