JP7418343B2 - 樹脂組成物、硬化膜、硬化膜付きプリント配線板およびその製造方法 - Google Patents
樹脂組成物、硬化膜、硬化膜付きプリント配線板およびその製造方法 Download PDFInfo
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- JP7418343B2 JP7418343B2 JP2020553189A JP2020553189A JP7418343B2 JP 7418343 B2 JP7418343 B2 JP 7418343B2 JP 2020553189 A JP2020553189 A JP 2020553189A JP 2020553189 A JP2020553189 A JP 2020553189A JP 7418343 B2 JP7418343 B2 JP 7418343B2
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- wiring board
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
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Description
バインダー樹脂は、有機溶媒に対して可溶性であり、ポリエチレングリコール換算の重量平均分子量が1,000以上、1,000,000以下のポリマーである。バインダー樹脂の重量平均分子量は、2,000~200,000がより好ましく、3,000~100,000がさらに好ましく、4,000~50,000が特に好ましい。バインダー樹脂の重量平均分子量が上記範囲内であれば、耐熱性と柔軟性に優れる硬化膜が得られやすい。
熱硬化性樹脂は、分子内に少なくとも1つの熱硬化性官能基を有する化合物である。熱硬化性樹脂としては、エポキシ樹脂、オキセタン樹脂、イソシアネート樹脂、ブロックイソシアネート樹脂、ビスマレイミド樹脂、ビスアリルナジイミド樹脂、ポリエステル樹脂(例えば不飽和ポリエステル樹脂等)、ジアリルフタレート樹脂、珪素樹脂、ビニルエステル樹脂、メラミン樹脂、ポリビスマレイミドトリアジン樹脂(BT樹脂)、シアネート樹脂(例えばシアネートエステル樹脂等)、ユリア樹脂、グアナミン樹脂、スルホアミド樹脂、アニリン樹脂、ポリウレア樹脂、チオウレタン樹脂、ポリアゾメチン樹脂、エピスルフィド樹脂、エン-チオール樹脂、ベンゾオキサジン樹脂等が挙げられる。硬化膜に耐熱性を付与できると共に、金属箔等の導体や回路基板に対する接着性を付与できることから、1分子中に2以上のエポキシ基を有する多官能エポキシ樹脂が好ましい。
樹脂組成物は、難燃剤として下記の一般式で表される有機リン系化合物(スピロ環ジホスホネート化合物)を含む。
樹脂組成物は、光硬化性化合物を含んでいてもよい。光硬化性化合物を含むことにより、樹脂組成物は感光性を有する。(a)バインダー樹脂が光硬化性官能基を有する場合、光硬化性化合物は(a)成分とも反応するため、光硬化膜の架橋密度が高められ、耐熱性や耐薬品性が向上する傾向がある。
(a)成分が光重合性官能基を有する場合、および/または樹脂組成物が(d)成分を含む場合、樹脂組成物は、(e)光重合開始剤を含有することが好ましい。光重合開始剤は、UV(紫外光)等の光エネルギーを吸収して活性化し、ラジカル重合性基の反応を開始・促進させる化合物である。樹脂組成物が光重合開始剤を含有することにより、樹脂組成物を感光性樹脂組成物として利用することができる。
樹脂組成物が(f)着色剤を含有することにより、樹脂組成物により形成される絶縁膜を任意に着色することができる。着色剤は、染料または顔料のいずれかである。着色剤としては、青色着色剤、赤色着色剤、黄色着色剤、橙色着色剤、紫色着色剤等が挙げられる。複数の着色剤を組み合わせることにより様々な色の絶縁膜を形成できる。例えば、青色顔料と橙色顔料と紫色顔料とを組み合わせることにより、黒色着色剤黒色着色剤とすることもできる。
樹脂組成物は、上記(a)~(f)成分の他に溶媒を含んでいてもよい。溶媒としては、バインダーポリマー等の樹脂成分を溶解できるものであれば特に限定されず、スルホキシド類、ホルムアミド類、アセトアミド類、ピロリドン類、アセテート類、エーテル類、ヘキサメチルホスホルアミド、γ-ブチロラクトン等の極性有機溶媒が好適に用いられる。これらの極性有機溶媒と、キシレン、トルエン等の芳香族炭化水素とを組み合わせて用いることもできる。
上記の各成分を混合することにより、樹脂組成物を調製する。上記の各成分は、混合前および/または混合後に、必要に応じて、粉砕・分散や、脱泡等の操作を行ってもよい。粉砕・分散は、例えば、ビーズミル、ボールミル、3本ロール等の混練装置を用いて実施すればよい。
樹脂組成物(溶液)を基板上に塗布し、必要に応じて溶媒を乾燥することにより絶縁膜を形成できる。基板としては、例えばプリント配線板が用いられる。プリント配線板の金属配線上に絶縁膜を形成することにより、絶縁信頼性が高められる。プリント配線板は、ポリイミドフィルム等の可撓性基板を用いたフレキシブルプリント配線板であってもよい。
以下の合成例では、分子内にカルボキシ基を有するポリマーを重合した。合成例1,2で得られたポリマーの特性は、以下の方法により評価した。
JIS K 5601-1-2に従って測定を行った。乾燥条件は170℃×1時間とした。
ゲルパーミエーションクロマトグラフィー(GPC)により、下記条件で測定を行った。
使用装置:東ソー HLC-8220GPC相当品
カラム:東ソー TSK gel Super AWM-H(6.0mm I.D.×15cm)×2本
ガードカラム:東ソー TSK guard column Super AW-H
溶離液:30mM LiBr + 20mM H3PO4 in DMF
流速:0.6mL/min
カラム温度:40℃
検出条件:RI:ポラリティ(+)、レスポンス(0.5sec)
試料濃度:約5mg/mL
分子量標準品:PEG(ポリエチレングリコール)
JIS K 5601-2-1に従って測定を行った。
攪拌機、温度計、滴下漏斗、および窒素導入管を備えた反応容器に、重合用溶媒として1,2-ビス(2-メトキシエトキシ)エタン(メチルトリグライム)40.00gおよびノルボルネンジイソシアネート20.62g(0.100モル)を仕込み、窒素気流下で攪拌しながら80℃に加温して溶解させた。この溶液に、ポリカーボネートジオール(旭化成株式会社製、商品名:PCDL T5652、重量平均分子量2000):50.00g(0.025モル)、2,2-ビス(ヒドロキシメチル)ブタン酸:3.70g(0.025モル)、および2-ヒドロキシエチルメタクリレート:13.02g(0.100モル)をメチルトリグライム:40.00gに溶解した溶液を1時間かけて添加した。この溶液を80℃で5時間加熱攪拌して、分子内にカルボキシ基を含有し、末端にメタクリロイル基を有するウレタンポリマー(a1)の溶液を得た。溶液の固形分濃度は52%、ポリマーの重量平均分子量は8,600、酸価は18mgKOH/gであった。
攪拌機、温度計、滴下漏斗、および窒素導入管を備えた反応容器に、重合用溶媒としてメチルトリグライム100.0gを仕込み、窒素気流下で攪拌しながら80℃に昇温した。これに、室温で予め混合しておいた、メタクリル酸12.0g(0.14モル)、メタクリル酸ベンジル28.0g(0.16モル)、メタクリル酸ブチル60.0g(0.42モル)、およびラジカル重合開始剤としてアゾビスイソブチロニトリル0.5gを、80℃に保温した状態で3時間かけて滴下漏斗から滴下した。滴下終了後、反応溶液を攪拌しながら90℃に昇温し、反応溶液の温度を90℃に保ちながらさらに2時間攪拌を行い、分子内にカルボキシ基を含有するアクリル系ポリマー(a2)の溶液を得た。溶液の固形分濃度は50%、ポリマーの重量平均分子量は48,000、酸価は78mgKOH/gであった。
表1に示す配合の組成物(単位は重量部)をメチルトリグライムに溶解させ、攪拌装置により撹拌した後、3本ロールミルで分散した。その後、脱泡装置で脱泡を行い、均一な溶液を調製した。溶媒としてのメチルトリグライムの量(上記合成例のポリマー溶液に含まれる溶媒も含めた全溶媒量)は、30重量部とした。各樹脂組成物には、表1に示す成分の他に、1.0重量部の光重合開始剤(エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(o-アセチルオキシム;BASF製「イルガキュア OXE02」)および0.1重量部のブタジエン系消泡剤(共栄社化学製「フローレン AC-2000」)を添加した。
<ポリイミドフィルム上への硬化膜の形成>
厚み25μmのポリイミドフィルム(カネカ製「アピカル25NPI」)上に、樹脂組成物を、スクリーン印刷により最終乾燥厚みが20μmになるように塗布し、80℃で20分乾燥した後、100mJ/cm2の積算露光量の紫外線を照射して露光した。次いで、30℃の1.0重量%炭酸ナトリウム水溶液を、1.0kgf/mm2の吐出圧で60秒スプレーして現像を行った。現像後、純水で十分洗浄した後、140℃のオーブン中で60分加熱して、ポリイミドフィルム上に硬化膜(現像後)を形成した。
硬化膜(現像前および現像後)を形成したポリイミドフィルムを試料として、難燃性UL94規格に従い、以下のように難燃性試験を行った。
硬化膜付きポリイミドフィルムを、幅50mm×長さ200mmに切り出し、長さ方向の中央部分(125mmの箇所)に標線を入れ、硬化膜側が外側となるように筒状に丸め、標線よりも上の重ね合わせ部分(長さ方向75mmの箇所)および上部に、隙間がないようにテープを貼り、難燃性試験用の筒を作製した。
A:5本全てがOKであったもの
B:5本中1~4本がOKであったもの
C:5本全てがNGであったもの
硬化膜(現像前および現像後)を形成したポリイミドフィルムを試料として、JIS K5400の碁盤目テープ法に準じて、硬化膜の密着性を評価した。1つの試料に対してテープ剥離試験を5回繰り返して行い、試験後の試料における硬化膜の残存面積率(残膜率)から、下記の基準で評価を行った。
A:剥がれがみられなかったもの(残存面積率100%)
B:剥離がみられたが、残存面積率が95%以上であったもの
C:残存面積率が80%以上95未満であったもの
D:残存面積率が80%未満であったもの
A:折り曲げ10回でもクラックが発生しなかったもの
B:折り曲げ2回以上9回以下でクラックが発生したもの
C:折り曲げ1回でクラックが発生したもの
上記と同様にして、ポリイミドフィルム上に樹脂組成物を塗布し、80℃で20分乾燥し、塗膜(Bステージ膜)が形成されたポリイミドフィルムを作製した。塗膜同士が接するように2枚のフィルムを重ね合わせ、引き剥がしたときの状態を観察し、下記の基準により評価した。
A:塗膜同士の貼り付きがなく、塗膜に貼り付き跡も残っていなかったもの
B:塗膜同士が貼り付き剥がした後に跡が残っていたもの、または塗膜同士が完全に貼り付いて引き剥がせなかったもの
厚み25μmのポリイミドフィルム(カネカ製「アピカル25NPI」)と厚み12μmの電解銅箔とをポリイミド系接着剤により張り合わせたフレキシブル銅張積層板の銅箔を、ライン幅/スペース幅=100μm/100μmの櫛形パターンにエッチングし、10容量%の硫酸水溶液中に1分間浸漬して銅箔の表面処理を行った後、純水で洗浄してフレキシブルプリント配線板を作製した。このフレキシブルプリント配線板の配線形成面に、脂組成物を、スクリーン印刷により最終乾燥厚みが20μmになるように塗布し、上記と同様に、乾燥、露光、現像、洗浄および加熱を行い、硬化膜付きフレキシブルプリント配線板を得た。この試料の配線の端子を電源に接続し、85℃、85%RHの環境試験機中で100Vの直流電流を1000時間印加した後、試料を目視にて観察し、下記の基準により評価した。
A:試験片表面および銅配線上に、膨れ、染み出し等の異常がみられなかったもの
B:試験片表面および/または銅配線上に、膨れ、染み出し等の異常が見られたもの
実施例および比較例の樹脂組成物の組成(配合、および固形分全量に対するP原子含有量)、ならびに評価結果を、表1に一覧で示す。なお、表1の斜線の項目は未評価である。各成分の詳細は以下に示す通りである。
<2>日立化成製「ファンクリル FA-321M」;EO変性ビスフェノールAジメタクリレート(平均分子量804)
<3>帝人製「ファイヤガード FCX-210」;スピロ環ジホスホネート系難燃剤
<4>クラリアント製「Exolit OP-935」;ホスフィン酸金属塩系難燃剤
<5>大塚化学製「SPB-100L」;ホスファゼン系難燃剤
<6>ナバルテック製「APYRAL AOH60」;水酸化アルミニウム系難燃剤
<7>大八木化学工業製「CR-733S」;リン酸エステル系難燃剤
<8>下記の青色顔料、橙色顔料および紫色顔料を、重量比1:1:1で混合した黒色顔料
青色顔料:BASF製 Pigment Blue 15:4
橙色顔料:クラリアント製 Pigment Orange 43
紫色顔料:クラリアント製 Pigment Violet 19
Claims (11)
- (a)分子内にウレタン結合を有するポリマーであるバインダー樹脂、(b)熱硬化性樹脂、(c)難燃剤、および(e)光重合開始剤を含む硬化性樹脂組成物であって、
前記(a)バインダー樹脂が、分子内にエチレン性不飽和基を有すること;および
硬化性樹脂組成物が、さらに、(d)エチレン性不飽和基を有する光硬化性化合物を含むこと
のうち、少なくともいずれか一方を満たし、
前記光重合開始剤の含有量が、前記(a)バインダー樹脂および前記(d)光硬化性化合物の合計100重量部に対して、0.1~10重量部であり、
前記(c)難燃剤が、下記一般式で表される有機リン系化合物である、樹脂組成物:
- 前記(a)バインダー樹脂が、分子内にカルボキシ基を有する、請求項1に記載の樹脂組成物。
- 前記(a)バインダー樹脂の酸価が5~200mgKOH/gである、請求項2に記載の樹脂組成物。
- さらに、(f)着色剤を含有する、請求項1~3のいずれか1項に記載の樹脂組成物。
- 前記(b)熱硬化性樹脂が多官能エポキシ樹脂である、請求項1~4のいずれか1項に記載の樹脂組成物。
- 全固形分100重量部に対する前記(c)難燃剤の含有量が、10~30重量部である、請求項1~5のいずれか1項に記載の樹脂組成物。
- 請求項1~6のいずれか1項に記載の樹脂組成物の硬化物からなる硬化膜。
- プリント配線板上に、請求項7に記載の硬化膜を備える硬化膜付きプリント配線板。
- 前記プリント配線板が可撓性を有する、請求項8に記載の硬化膜付きプリント配線板。
- 請求項1~6のいずれか1項に記載の樹脂組成物をプリント配線板の金属配線形成面に塗布して塗布膜を形成し、
前記塗布膜を加熱および/または露光することにより硬化する、硬化膜付きプリント配線板の製造方法。 - 請求項1~6のいずれか1項に記載の樹脂組成物をプリント配線板の金属配線形成面に塗布して塗布膜を形成し、
前記塗布膜の面内の少なくとも一部に活性光線を照射して光硬化を行い、
アルカリにより現像を行い、未硬化の前記塗布膜を溶解除去することにより、パターニングされた硬化膜を形成する、
硬化膜付きプリント配線板の製造方法。
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