JP7142453B2 - 放熱絶縁性樹脂組成物、及びそれを用いたプリント配線板 - Google Patents
放熱絶縁性樹脂組成物、及びそれを用いたプリント配線板 Download PDFInfo
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- JP7142453B2 JP7142453B2 JP2018070150A JP2018070150A JP7142453B2 JP 7142453 B2 JP7142453 B2 JP 7142453B2 JP 2018070150 A JP2018070150 A JP 2018070150A JP 2018070150 A JP2018070150 A JP 2018070150A JP 7142453 B2 JP7142453 B2 JP 7142453B2
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011163 secondary particle Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
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- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
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- H05K3/22—Secondary treatment of printed circuits
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
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Description
しかしながら、かかる金属ベース基板では、電気絶縁層の熱伝導性が低いために絶縁層を薄くする必要があり、その結果として、電気絶縁層の絶縁耐力が低下するといった問題が生じることがあった。
この点、比較的微粒で製造されるβ-炭化ケイ素は、丸みを帯びた形状であり、組成物中への高充填や最密充填が可能であり、これを放熱性無機粒子として用いた本発明の放熱絶縁性樹脂組成物では、この放熱無機粒子の沈降が生じにくく、印刷性を悪化させることなく、熱伝導率の向上を図ることができる。
なお、本明細書において、遠赤外線とは、一般的な概念である波長4~1000μmの電磁波を示す。また、遠赤外線を放射するセラミックス粒子とは、例えば、特開2003-136618号公報に記載してあるような、理想黒体に対して、好ましくは80%以上の高い遠赤外線放射率を持つセラミック粒子である。
また、本発明の(A)放熱性無機粒子は、最密充填となるような粒度分布を持つ2種類以上の平均粒子径のものを配合することにより、更に高充填にすることができ、保存安定性、熱伝導率の両側面から好ましい。
これらのカップリング剤は、表面未処理の(A)放熱性無機粒子とカップリング剤とを別々に配合して、組成物中で(A)放熱性無機粒子が表面処理されてもよいが、予め(A)放熱性無機粒子の表面にカップリング剤を吸着あるいは反応により固定化することが好ましい。この場合、表面処理に用いるカップリング剤量および表面処理方法については特に制限されない。
オキセタン環を含有する化合物であり、具体的な化合物としては、3-エチル-3-ヒドロキシメチルオキセタン(東亞合成(株)製の商品名 OXT-101)、3-エチル-3-(フェノキシメチル)オキセタン(東亞合成(株)製の商品名 OXT-211)、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン(東亞合成社製の商品名 OXT-212)、1,4-ビス{[(3-エチル-3-オキセタニル)メトキシ]メチル}ベンゼン(東亞合成社製の商品名 OXT-121)、ビス(3-エチル-3-オキセタニルメチル)エーテル(東亞合成社製の商品名 OXT-221)などが挙げられる。さらに、フェノールノボラックタイプのオキセタン化合物なども挙げられる。
攪拌機、温度計、還流冷却管、滴下ロートおよび窒素導入管を備えた2リットル容セパラブルフラスコに、ジエチレングリコールジメチルエーテル900g、およびt-ブチルパーオキシ2-エチルヘキサノエート(日本油脂(株)製パーブチルO)21.4gを仕込み、90℃に昇温後、メタクリル酸309.9g、メタクリル酸メチル116.4g、及び一般式(I)で示されるラクトン変性2-ヒドロキシエチルメタクリレート(ダイセル化学工業(株)製プラクセルFM1)109.8gをビス(4-t-ブチルシクロヘキシル)パーオキシジカーボネート(日本油脂(株)製パーロイルTCP)21.4gと共にジエチレングリコールジメチルエーテル中に3時間かけて滴下し、さらに6時間熟成することによってカルボキシル基含有共重合樹脂溶液を得た。反応は、窒素雰囲気下で行った。
次に上記カルボキシル基含有共重合樹脂溶液に、3,4-エポキシシクロヘキシルメチルアクリレート(ダイセル化学(株)製サイクロマーA200)363.9g、ジメチルベンジルアミン3.6g、ハイドロキノンモノメチルエーテル1.80gを加え、100℃に昇温し、撹拌することによってエポキシの開環付加反応を行った。16時間後、固形分酸価=108.9mgKOH/g、重量平均分子量=25,000(スチレン換算)のカルボキシル基含有共重合樹脂を、53.8%(不揮発分)含む溶液を得た。
下記表1に示す実施例1~4及び比較例1~5の配合成分を、3本ロールミルで混練し、放熱絶縁性樹脂組成物を得た。
「炭化ケイ素の体積占有率(%)」=(V1-V0)/V1×100
注2.同様に、「酸化アルミニウムの体積占有率(%)」も、酸化アルミニウムと溶剤以外の体積V0と、溶剤以外の成分の体積V1から、以下のように求めた。
「酸化アルミニウムの体積占有率(%)」=(V1-V0)/V1×100
*1:信濃電気製錬(株)製平均粒子径約9.5μmのα-炭化ケイ素
*2:信濃電気製錬(株)製平均粒子径約1.2μmのα-炭化ケイ素
*3:スーペリアグラファイト社製平均粒径約7.8μmのβ-炭化ケイ素
*4:スーペリアグラファイト社製平均粒径約1.3μmのβ-炭化ケイ素
*5:電気化学工業(株)製の平均粒子径約8μmの球状酸化アルミニウム
*6:電気化学工業(株)製の平均粒子径約0.3μmの球状酸化アルミニウム
*7:DIC(株)製フェノールノボラック型エポキシ樹脂
*8:三菱ケミカル(株)製ビスフェノールA型エポキシ樹脂
*9:2,4-ジアミノ-6-[2’-メチルイミダゾリル-(1’)]-エチル-s-トリアジン
*10:上記で合成した光重合性オリゴマー(b-2)
*11:トリメチロールプロパントリアクリレート
*12:BASF社製の光重合開始剤
*13:ビック・ケミー・ジャパン(株)製の湿潤剤
*14:信越化学工業(株)製シリコーン系消泡剤
*15:ウイルバー・エリス(株)製有機ベントナイト
実施例1、2および比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を、ポリエチレン製の密封黒色容器に入れて5℃にて保存した。1日後、2日後、7日後、30日後、90日後の沈降状態を評価した。
また、実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を、ポリエチレン製の密封黒色容器に入れて20℃の暗所にて保存した。1日後、2日後、7日後、30日後、90日後の沈降状態を評価した。
◎:沈降なし。
○:若干沈降しているが凝集はなく、攪拌することにより使用に問題なし。
×:沈降し凝集している。攪拌してもダマとなり、使用不能である。
実施例1、2および比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を、回路形成されたFR-4基板上にスクリーン印刷で乾燥塗膜が約30μmとなるようにパターン印刷し、150℃で60分間硬化させた。
また、実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を回路形成されたFR-4基板上にスクリーン印刷で乾燥塗膜が約30μmとなるようにパターン印刷し、メタルハライドランプにて350nmの波長で2J/cm2の積算光量を照射した後、150℃60分間熱硬化させた。得られた基板をプロピレングリコールモノメチルエーテルアセテートに30分間浸漬し、乾燥後、セロハン粘着テープによるピールテストを行い、塗膜の剥がれ・変色について評価した。
○:剥がれや変色がない。
×:剥がれや変色がある。
実施例1、2および比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物と実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を用いて、耐溶剤性と同様の方法で硬化した。得られた基板にロジン系フラックスを塗布して、260℃のはんだ槽で10秒間フローさせて、プロピレングリコールモノメチルエーテルアセテートで洗浄・乾燥後、セロハン粘着テープによるピールテストを行い、塗膜の剥がれについて評価した。
○:剥がれがない。
×:剥がれがある。
実施例1、2および比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物と実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を用いて、耐溶剤性と同様の方法で硬化した。得られた基板に、Bから9Hの鉛筆の芯を先が平らになるように研ぎ、約45°の角度で押しつけて塗膜が剥がれない鉛筆の硬さを記録した。
実施例1、2及び比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を回路形成されたFR-4基板上にスクリーン印刷で乾燥塗膜が約30μmとなるようにパターン印刷し、150℃60分間硬化させた。
また、実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を回路形成されたFR-4基板上にスクリーン印刷で乾燥塗膜が約30μmとなるようにパターン印刷し、メタルハライドランプにて350nmの波長で2J/cm2の積算光量を照射した後、150℃60分間熱硬化させた。
得られた基板をJISK5400に準拠して、各サンプルの皮膜に、1mmの碁盤目100個(10×10)を作り、碁盤目上に透明粘着テープ(ニチバン社製、幅:18mm)を完全に付着させ、直ちにテープの一端をガラス基板に対して直角に保ちながら瞬間的に引き離し、碁盤目に剥がれが生じたかを調べた。評価基準は以下のとおりである。
○:碁盤目に剥がれが生じなかった。
×:碁盤目に剥がれが生じた。
実施例1、2および比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物をIPC規格Bパターンのくし形電極が形成されたFR-4基板上にスクリーン印刷で乾燥塗膜が約30μmとなるようにパターン印刷し、150℃で60分間硬化させた。また、実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物をIPC規格Bパターンのくし形電極が形成されたFR-4基板上にスクリーン印刷で乾燥塗膜が約30μmとなるようにパターン印刷し、メタルハライドランプにて350nmの波長で2J/cm2の積算光量を照射して硬化させた。得られた基板の電極間の絶縁抵抗値を印加電圧500Vにて測定した。
実施例1、2および比較例1、2の、熱硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を圧延銅箔上にスクリーン印刷で乾燥塗膜が約50μmとなるように印刷し、150℃60分間硬化させた。また、実施例3、4および比較例3、4、5の、熱硬化性樹脂組成物および光硬化性樹脂組成物を含有する放熱絶縁性樹脂組成物を圧延銅箔上にスクリーン印刷で乾燥塗膜が約50μmとなるように印刷し、メタルハライドランプにて350nmの波長で2J/cm2の積算光量を照射した後、150℃60分間熱硬化させた。
その後、圧延銅箔を剥がして得られたフィルム状硬化物を、京都電子工業株式会社製QTM500を用いて熱伝導率の測定を行い、n=3の平均値を求めた。
Claims (6)
- (A)放熱性無機粒子、(B)硬化性樹脂組成物を含有してなる放熱絶縁性樹脂組成物であって、前記(A)放熱性無機粒子が少なくとも(A-1)β-炭化ケイ素と球状の酸化アルミニウムを含有し、かつ、前記(A)放熱性無機粒子の体積占有率が、前記放熱絶縁性樹脂組成物の硬化物全容量に対して60容量%以上であり、
前記(A-1)β-炭化ケイ素粒子の前記(A)放熱性無機粒子中の含有比率が20容量%以上であり、
前記(B)硬化性樹脂組成物が、(B-1)熱硬化性樹脂組成物であることを特徴とする放熱絶縁性樹脂組成物。 - (A)放熱性無機粒子、(B)硬化性樹脂組成物を含有してなる放熱絶縁性樹脂組成物であって、前記(A)放熱性無機粒子が少なくとも(A-1)β-炭化ケイ素と球状の酸化アルミニウムを含有し、かつ、前記(A)放熱性無機粒子の体積占有率が、前記放熱絶縁性樹脂組成物の硬化物全容量に対して60容量%以上であり、
前記(A-1)β-炭化ケイ素粒子の前記(A)放熱性無機粒子中の含有比率が20容量%以上60容量%未満であり、
前記(B)硬化性樹脂組成物が、(B-2)光硬化性樹脂組成物であることを特徴とする放熱絶縁性樹脂組成物。 - (A)放熱性無機粒子、(B)硬化性樹脂組成物を含有してなる放熱絶縁性樹脂組成物であって、前記(A)放熱性無機粒子が少なくとも(A-1)β-炭化ケイ素と球状の酸化アルミニウムを含有し、かつ、前記(A)放熱性無機粒子の体積占有率が、前記放熱絶縁性樹脂組成物の硬化物全容量に対して60容量%以上であり、
前記(A-1)β-炭化ケイ素粒子の前記(A)放熱性無機粒子中の含有比率が20容量%以上60容量%未満であり、
前記(B)硬化性樹脂組成物が、(B-1)熱硬化性樹脂組成物と(B-2)光硬化性樹脂組成物の混合物であることを特徴とする放熱絶縁性樹脂組成物。 - 前記(B-1)熱硬化性樹脂組成物が、エポキシ化合物および/またはオキセタン化合物と、硬化剤および/または硬化触媒を含有することを特徴とする請求項1または3に記載の放熱絶縁性樹脂組成物。
- 前記(B-2)光硬化性樹脂組成物が、一分子中に1個以上のエチレン性不飽和結合を有する化合物と、光重合開始剤を含有することを特徴とする請求項2または3に記載の放熱絶縁性樹脂組成物。
- 前記請求項1~5のいずれか一項に記載の放熱絶縁性樹脂組成物を、熱硬化および/または光硬化して得られる硬化物により、絶縁層および/またはソルダーレジスト層が形成されてなることを特徴とするプリント配線板。
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