JP2011215377A - 光硬化性熱硬化性樹脂組成物 - Google Patents
光硬化性熱硬化性樹脂組成物 Download PDFInfo
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- JP2011215377A JP2011215377A JP2010083422A JP2010083422A JP2011215377A JP 2011215377 A JP2011215377 A JP 2011215377A JP 2010083422 A JP2010083422 A JP 2010083422A JP 2010083422 A JP2010083422 A JP 2010083422A JP 2011215377 A JP2011215377 A JP 2011215377A
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
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- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
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- 150000004692 metal hydroxides Chemical class 0.000 description 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 238000013508 migration Methods 0.000 description 1
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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Landscapes
- Materials For Photolithography (AREA)
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- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Abstract
Description
まず、本実施形態の光硬化性熱硬化性樹脂組成物を構成する一般式(1)〜(4)に示す構造を有するカルボキシル基含有感光性樹脂は、下記の方法により容易に得ることができる。
[1]フェノール樹脂とアルキレンオキサイドとを反応させて得られる反応生成物に不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られるカルボキシル基含有感光性樹脂。
[2]フェノール樹脂とシクロカーボネート化合物とを反応させて得られる反応生成物に不飽和基含有モノカルボン酸を反応させ、得られる反応生成物に多塩基酸無水物を反応させて得られるカルボキシル基含有感光性樹脂。
このように、カルボキシル基含有感光性樹脂における塩素イオン不純物を抑え、実質的に水酸基を含まないことにより、優れた絶縁信頼性、PCT耐性を発現することが可能となる。
アルキレンオキサイド又はシクロカーボネート化合物の付加量としては、フェノール性水酸基1当量当たり、0.3〜10モルの範囲であることが好ましい。付加量が上記範囲より少ない場合、後述する不飽和基含有モノカルボン酸や多塩基酸無水物との反応が起こり難くなり、感光性及び希アルカリ水溶液に対する溶解性が低下する。一方、付加量が上記範囲を超えた場合、生成するエーテル結合により、耐水性が低下し、電気絶縁性、HAST耐性等が低下する。より好ましくは0.8〜5モルの範囲であり、またさらに好ましくは1.0〜3モルの範囲である。
特に式中、X、Yが、それぞれ、メチル基又はエチル基であり、Zはメチル又はフェニルであり、nは0であり、Arは、フェニレン、ナフチレン、又はチエニレンであることが好ましい。
これら熱硬化性成分は単独又は2種以上を併用することができる。
これら1分子中に複数のイソシアネート基又はブロック化イソシアネート基を有する化合物は、1種を単独で又は2種以上を組み合わせて用いることができる。
金属塩化物としては、Cr、Mn、Co、Ni、Fe、Cu又はAlからなる金属の塩化物で、例えば、塩化第二コバルト、塩化第一ニッケル、塩化第二鉄などが挙げられる。
金属アセチルアセトネート塩としては、Cr、Mn、Co、Ni、Fe、Cu又はAlからなる金属のアセチルアセトネート塩であり、例えば、コバルトアセチルアセトネート、ニッケルアセチルアセトネート、鉄アセチルアセトネートなどが挙げられる。
金属硫酸塩としては、Cr、Mn、Co、Ni、Fe、Cu又はAlからなる金属の硫酸塩で、例えば、硫酸銅などが挙げられる。
ウレタン化触媒の配合量は、通常の量的割合で充分であり、例えばカルボキシル基含有樹脂100質量部に対して、好ましくは0.1〜20質量部、より好ましくは0.5〜10.0質量部である。
ジスアゾ系:Pigment Red 37, 38, 41。
モノアゾレーキ系:Pigment Red 48:1, 48:2, 48:3, 48:4, 49:1, 49:2, 50:1, 52:1, 52:2, 53:1, 53:2, 57:1, 58:4, 63:1, 63:2, 64:1,68。
ぺリレン系:Solvent Red 135, 179, Pigment Red 123, 149, 166, 178, 179, 190, 194, 224。
ジケトピロロピロール系:Pigment Red 254, 255, 264, 270, 272。
縮合アゾ系:Pigment Red 220, 144, 166, 214, 220, 221, 242。
アンスラキノン系:Pigment Red 168, 177, 216、Solvent Red 149, 150, 52, 207。
キナクリドン系:Pigment Red 122, 202, 206, 207, 209。
青色着色剤としてはフタロシアニン系、アントラキノン系があり、顔料系はピグメント(Pigment)に分類されている化合物、具体的には、下記のようなものを挙げることができる:Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60。染料系としては、Solvent Blue 35, 63, 68, 70, 83, 87, 94, 97, 122, 136, 67, 70等を使用することができる。上記以外にも、金属置換もしくは無置換のフタロシアニン化合物も使用することができる。
緑色着色剤としては、同様にフタロシアニン系、アントラキノン系、ペリレン系があり、具体的にはPigment Green 7, 36、Solvent Green 3, 5, 20, 28等を使用することができる。上記以外にも、金属置換もしくは無置換のフタロシアニン化合物も使用することができる。
黄色着色剤としてはモノアゾ系、ジスアゾ系、縮合アゾ系、ベンズイミダゾロン系、イソインドリノン系、アントラキノン系等があり、具体的には以下のものが挙げられる。
アントラキノン系:Solvent Yellow 163, Pigment Yellow 24, 108, 193, 147, 199, 202。
イソインドリノン系:Pigment Yellow 110, 109, 139, 179, 185。
縮合アゾ系:Pigment Yellow 93, 94, 95, 128, 155, 166, 180。
モノアゾ系:Pigment Yellow 1, 2, 3, 4, 5, 6, 9, 10, 12, 61, 62, 62:1, 65, 73, 74, 75, 97, 100, 104, 105, 111, 116, 167, 168, 169, 182, 183。
ジスアゾ系:Pigment Yellow 12, 13, 14, 16, 17, 55, 63, 81, 83, 87, 126, 127, 152, 170, 172, 174, 176, 188, 198。
具体的に例示すれば、Pigment Violet 19、23、29、32、36、38、42、Solvent Violet 13, 36、C.I. Pigment Orange 1, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73、Pigment Brown 23, 25, Pigment Black 1, 7等がある。
これら着色剤の配合割合は、特に制限はないが、前記カルボキシル基含有樹脂100質量部に対して、好ましくは10質量部以下、特に好ましくは0.1〜5質量部の割合で充分である。
また一般に、高分子材料は光を吸収し、それにより分解・劣化を起こすことから、本実施形態の光硬化性熱硬化性樹脂組成物には、紫外線に対する安定化対策を行うために、上記酸化防止剤の他に、紫外線吸収剤を使用することができる。
1Lオートクレーブに、オルソクレゾールと4,4−ビス(クロロメチル)ビフェニルの縮合反応により得られるビフェニルアラルキル樹脂(水酸基当量232g/eq)313.2g、水酸化カリウム3.13g、トルエン344.1gを仕込み130℃まで昇温しながら攪拌し溶解した。次にプロピレンオキサイド87.8gを徐々に滴下し、125〜130℃、0.15〜0.40MPaで10時間反応させた。その後、室温まで冷却し、反応溶液に85%リン酸を4.11g添加して水酸化カリウムを中和した。水酸基当量296g/eq、樹脂分54.8%のプロピレンオキサイド付加物溶液を得た。
1Lオートクレーブに、オルソクレゾールと4,4−ビス(クロロメチル)ビフェニル、4,4−ビス(クロロメチル)ベンゼンの共縮合反応により得られるビフェニル・フェニレン共縮合樹脂(水酸基当量215g/eq、平均3.7核体)370.0g、水酸化カリウム3.70g、トルエン370.0gを仕込み130℃まで昇温しながら攪拌し溶解した。次にプロピレンオキサイド111.9gを徐々に滴下し、125〜130℃、0.15〜0.40MPaで10時間反応させた。その後、室温まで冷却し、反応溶液に85%リン酸を4.85g添加して水酸化カリウムを中和した。水酸基当量278g/eq、樹脂分56.9%のプロピレンオキサイド付加物溶液を得た。
1Lオートクレーブに、クレゾールとハイドロキノン、4,4−ビス(クロロメチル)ビフェニルの共縮合反応から得られるビフェニルアラルキル樹脂(水酸基当量197g/eq、平均核体数3.1)400.3g、水酸化カリウム4.01g、トルエン402.3gを仕込み130℃まで昇温しながら攪拌し溶解した。次にプロピレンオキサイド132.1gを徐々に滴下し、125〜130℃、0.15〜0.40MPaで10時間反応させた。その後、室温まで冷却し、反応溶液に85%リン酸を5.26g添加して水酸化カリウムを中和した。水酸基当量261g/eq、樹脂分56.5%のプロピレンオキサイド付加物溶液を得た。
1Lオートクレーブに、クレゾールと1,4−ビスクロロメチルベンゼンから得られるクレゾールアラルキル樹脂(水酸基当量188g/eq、平均核体数4.6)400.0g、水酸化カリウム4.00g、トルエン399.9gを仕込み130℃まで昇温しながら攪拌し溶解した。次にプロピレンオキサイド138.4gを徐々に滴下し、125〜130℃、0.15〜0.40MPaで10時間反応させた。その後、室温まで冷却し、反応溶液に85%リン酸を5.24g添加して水酸化カリウムを中和した。水酸基当量252g/eq、樹脂分56.8%のプロピレンオキサイド付加物溶液を得た。
1Lオートクレーブに、クレゾールと1,4−ビスクロロメチルベンゼンから得られるクレゾールアラルキル樹脂(水酸基当量180g/eq、平均核体数3.3)400.0g、水酸化カリウム4.00g、トルエン402.1gを仕込み130℃まで昇温しながら攪拌し溶解した。次にプロピレンオキサイド144.6gを徐々に滴下し、125〜130℃、0.15〜0.40MPaで10時間反応させた。その後、室温まで冷却し、反応溶液に85%リン酸を5.24g添加して水酸化カリウムを中和した。水酸基当量243g/eq、樹脂分57.5%のプロピレンオキサイド付加物溶液を得た。
1Lオートクレーブに、クレゾールと1,4−ビスクロロメチルベンゼンから得られるクレゾールアラルキル樹脂(水酸基当量190g/eq、平均核体数5.4)400.0g、水酸化カリウム4.00g、トルエン400.0gを仕込み130℃まで昇温しながら攪拌し溶解した。次にプロピレンオキサイド137.0gを徐々に滴下し、125〜130℃、0.15〜0.40MPaで10時間反応させた。その後、室温まで冷却し、反応溶液に85%リン酸を5.24g添加して水酸化カリウムを中和した。水酸基当量254g/eq、樹脂分57.5%のプロピレンオキサイド付加物溶液を得た。
温度計、窒素導入装置兼アルキレンオキサイド導入装置及び撹拌装置を備えたオートクレーブに、ノボラック型クレゾール樹脂(昭和高分子社製、商品名「ショーノールC RG951」、OH当量:119.4)119.4g 、水酸化カリウム1.19g及びトルエン119.4gを仕込み、撹拌しつつ系内を窒素置換し、加熱昇温した。次に、プロピレンオキサイド63.8gを徐々に滴下し、125〜132℃ 、0〜4.8kg/cm2で16時間反応させた。その後、室温まで冷却し、この反応溶液に89%リン酸1.56gを添加混合して水酸化カリウムを中和し、不揮発分62.1%、水酸基価が182.2g/eq.であるノボラック型クレゾール樹脂のプロピレンオキサイド反応溶液を得た。これは、フェノール性水酸基1当量当りアルキレンオキサイドが平均1.08モル付加しているものであった。
ジエチレングリコールモノエチルエーテルアセテート600gにオルソクレゾールノボラック型エポキシ樹脂(DIC社製、EPICLON N−695、軟化点95℃、エポキシ当量214、平均官能基数7.6)1070g(グリシジル基数(芳香環総数):5.0モル)、アクリル酸360g(5.0モル)、及びハイドロキノン1.5gを仕込み、100℃に加熱攪拌し、均一溶解した。次いで、トリフェニルホスフィン4.3gを仕込み、110℃に加熱して2時間反応後、120℃に昇温してさらに12時間反応を行った。得られた反応液に芳香族系炭化水素(ソルベッソ150)415g、テトラヒドロ無水フタル酸456.0g(3.0モル)を仕込み、110℃で4時間反応を行い、冷却後、固形分酸価89mgKOH/g、固形分65%の樹脂溶液を得た。以下、これを樹脂溶液R−3と称す。
*2:ビスフェノール型エポキシ樹脂(YSLV-80XY:東都化成社製)
*3: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) (イルガキュア OXE 02:チバ・ジャパン社製)
*4:2-メルカプトベンゾチアゾール
*5:酸化防止剤(チバ・ジャパン社製)
*6:B-30 (堺化学社製)
*7:SO-E3(アドマテックス社製)
*8:ハイドロタルサイト(協和化学工業社製)
*9:C.I.Pigment Blue 15:3
*10:C.I.Pigment Yellow147
*11:ジエチレングリコールモノエチルエーテールアセテート
*12:ジペンタエリスリトールヘキサアクリレート
表1に示す実施例及び比較例の組成物について、以下に示す評価方法にて性能評価及び特性評価を行った。評価結果を表2に示す。
性能評価:
<最適露光量>
銅厚18μmの回路パターン基板を銅表面粗化処理(メック社製メックエッチボンドCZ−8100)後、水洗し、乾燥した後、表1に示す実施例及び比較例の光硬化性熱硬化性樹脂組成物をスクリーン印刷法により全面に塗布し、80℃の熱風循環式乾燥炉で60分間乾燥させ、約20μmの乾燥塗膜を得た。その後、高圧水銀灯搭載の露光装置を用いてステップタブレット(Kodak No.2)を介して露光し、現像(30℃、0.2MPa、1%炭酸ナトリウム水溶液)を90秒で行った際残存するステップタブレットのパターンが7段の時を最適露光量とした。
それぞれの光硬化性樹脂組成物をパターン形成された銅箔基板上にスクリーン印刷で前面塗布し、80℃の熱風循環式乾燥炉で30分間乾燥させ、室温まで放冷した。この基板にPET製ネガフィルムを当て、ORC社製(HMW−GW20)で1分間減圧条件下で圧着させ、その後、ネガフィルムを剥がしたときのフィルムの張り付き状態を評価した。
○:フィルムを剥がすときに、僅かに抵抗があり、塗膜に僅かに跡が確認できる
△:フィルムを剥がすときに、僅かに抵抗があり、塗膜にはっきり跡がついている
×:フィルムを剥がすときに、大きな抵抗があり、塗膜にはっきり跡がついている
表1に示す実施例及び比較例の組成物を、パターン形成された銅箔基板上にスクリーン印刷で乾燥膜厚約20μmになるように全面塗布し、80℃で乾燥し20分から80分まで5分おきに基板を取り出し、室温まで放冷した。この基板に30℃の1%炭酸ナトリウム水溶液をスプレー圧0.2MPaの条件で90秒間現像を行い、乾燥塗膜が残らない最大許容乾燥時間を最大現像ライフとして判断した。また、現像処理後、銅上に現像残渣が僅かに確認されるものについては現像残渣有りと記載した。
表1に示す実施例及び比較例の組成物を、パターン形成された銅箔基板上にスクリーン印刷で乾燥膜厚約20μmになるように全面塗布し、80℃で30分乾燥し、室温まで放冷した。この基板に高圧水銀灯を搭載した露光装置を用いて最適露光量でソルダーレジストパターンを露光し、30℃の1%炭酸ナトリウム水溶液をスプレー圧0.2MPaの条件で90秒間現像を行い、レジストパターンを得た。この基板を、UVコンベア炉にて積算露光量1000mJ/cm2の条件で紫外線照射した後、150℃で60分加熱して硬化した。得られたプリント基板(評価基板)に対して以下のように特性を評価した。
評価基板を10体積%H2SO4水溶液に室温で30分間浸漬し、染み込みや塗膜の溶け出しを目視にて確認し、さらにテープピールによる剥がれを確認した。
○:変化が認められないもの
△:ほんの僅か変化しているもの
×:塗膜に膨れあるいは膨潤脱落があるもの
評価基板を10体積%NaOH水溶液に室温で30分間浸漬し、染み込みや塗膜の溶け出しを目視にて確認し、さらにテープピールによる剥がれを確認した。
○:変化が認められないもの
△:ほんの僅か変化しているもの
×:塗膜に膨れあるいは膨潤脱落があるもの
ロジン系フラックスを塗布した評価基板を、予め260℃に設定したはんだ槽に浸漬し、変性アルコールでフラックスを洗浄した後、目視によるレジスト層の膨れ・剥がれについて評価した。判定基準は以下のとおりである。
○:10秒間浸漬を3回以上繰り返しても剥がれが認められない
△:10秒間浸漬を3回以上繰り返すと少し剥がれる
×:10秒間浸漬を3回以内にレジスト層に膨れ、剥がれがある
評価基板について、市販品の無電解ニッケルめっき浴及び無電解金めっき浴を用いて、ニッケル5μm、金0.05μmの条件で開口80μmのボールパットにめっき処理を行った。メッキされた評価基板において、テープピーリングにより、レジスト層の剥がれの有無やめっきのしみ込みの有無を評価した後、テープピーリングによりレジスト層の剥がれの有無を評価した。判定基準は以下のとおりである。
○:めっき後にしみ込みが見られず、テープピーリング後に剥がれはない
△:めっき後に白化が確認されるが、テープピーリング後の剥がれはない
×:現像残渣の影響により無電解金メッキ未着
耐無電解金めっき性の評価と同様に無電解金めっきを施した評価基板を、PCT装置(エスペック社製HAST SYSTEM TPC−412MD)を用いて、121℃、飽和、0.2MPaの条件で種々の時間処理し、塗膜の状態によりPCT耐性を評価した。判定基準は以下のとおりである。
○:300時間試験経過後、膨れ、剥がれ、変色、溶出のないもの
△:168時間試験経過時、膨れ、剥がれ、変色、溶出のないもの
×:168時間試験経過時、膨れ、剥がれ、変色、溶出が見られるもの
□抜き、○抜きパターンを形成したソルダーレジスト硬化塗膜を有する評価基板を作製した。得られた評価基板を冷熱衝撃試験器(エタック社製)で−55℃/30分〜150℃/30分を1サイクルとして1000サイクルの耐性試験を行った。試験後、処理後の硬化膜を目視により観察し、クラックの発生状況を下記の基準にて判断した。
○:クラック発生率30%未満
△:クラック発生率30〜50%
×:クラック発生率50%以上
クシ型電極(ライン/スペース=30ミクロン/30ミクロン)が形成されたBT基板に、ソルダーレジスト硬化塗膜を形成し、評価基板を作成した。この評価基板を、130℃、湿度85%の雰囲気下の高温高湿槽に入れ、電圧12Vを荷電し、種々の時間、槽内HAST試験を行った。種々の時間経過時の槽内絶縁抵抗値を下記の判断基準に従い評価した。
○:300時間経過後、108Ω以上
△:168時間経過時、108Ω以上
×:168時間経過時、108Ω以下
表1に示す配合割合で調製した実施例1〜8の各組成物をメチルエチルケトンにて希釈し、PETフィルム上に塗布して80℃で30分乾燥し、厚さ20μmの感光性樹脂組成物層を形成した。さらにその上にカバーフィルムを貼り合わせてドライフィルムを作製し、それぞれを実施例9〜16とした。
上記のようにして得られたドライフィルムからカバーフィルムを剥がし、パターン形成された銅箔基板に、フィルムを熱ラミネートし、次いで、上記の塗膜特性評価に用いた基板と同様の条件で露光した。露光後、キャリアフィルムを剥がし、30℃の1%炭酸ナトリウム水溶液をスプレー圧0.2MPaの条件で90秒間現像を行い、レジストパターンを得た。この基板を、UVコンベア炉にて積算露光量1000mJ/cm2の条件で紫外線照射した後、150℃で60分加熱して硬化した。得られた硬化皮膜を有する試験基板について、上記の評価方法にて性能評価及び特性評価を行った。評価結果を表3に示す。
Claims (4)
- 請求項1に記載の光硬化性熱硬化性樹脂組成物を、フィルム上に塗布乾燥して得られることを特徴とする光硬化性熱硬化性のフィルム。
- 請求項1に記載の光硬化性熱硬化性樹脂組成物、又は請求項2に記載のフィルムを、活性エネルギー線照射及び/又は加熱により硬化して得られることを特徴とする硬化物。
- 請求項1に記載の光硬化性熱硬化性樹脂組成物、又は請求項2に記載のフィルムを、活性エネルギー線照射及び/又は加熱により硬化して得られることを特徴とする硬化物を具備するプリント配線板。
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JP5572737B1 (ja) * | 2013-06-04 | 2014-08-13 | 太陽インキ製造株式会社 | 光硬化熱硬化性樹脂組成物、硬化物、及びプリント配線板 |
JP2017120395A (ja) * | 2015-12-25 | 2017-07-06 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
JP2018049220A (ja) * | 2016-09-23 | 2018-03-29 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
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JP2011208108A (ja) * | 2010-03-31 | 2011-10-20 | Air Water Inc | 感光性樹脂の製造方法 |
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WO2014196502A1 (ja) * | 2013-06-04 | 2014-12-11 | 太陽インキ製造株式会社 | 光硬化熱硬化性樹脂組成物、硬化物、及びプリント配線板 |
KR20160016817A (ko) * | 2013-06-04 | 2016-02-15 | 다이요 잉키 세이조 가부시키가이샤 | 광경화 열경화성 수지 조성물, 경화물, 및 프린트 배선판 |
KR102167483B1 (ko) * | 2013-06-04 | 2020-10-19 | 다이요 잉키 세이조 가부시키가이샤 | 광경화 열경화성 수지 조성물, 경화물, 및 프린트 배선판 |
JP2017120395A (ja) * | 2015-12-25 | 2017-07-06 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
JP2018049220A (ja) * | 2016-09-23 | 2018-03-29 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
TWI742150B (zh) * | 2016-09-23 | 2021-10-11 | 日商田村製作所股份有限公司 | 感光性樹脂組成物 |
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