JP2013137511A - 導電性樹脂組成物及び導電回路 - Google Patents
導電性樹脂組成物及び導電回路 Download PDFInfo
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- JP2013137511A JP2013137511A JP2012237783A JP2012237783A JP2013137511A JP 2013137511 A JP2013137511 A JP 2013137511A JP 2012237783 A JP2012237783 A JP 2012237783A JP 2012237783 A JP2012237783 A JP 2012237783A JP 2013137511 A JP2013137511 A JP 2013137511A
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Abstract
【解決手段】カルボキシル基含有樹脂、導電性粉末、4官能基のアクリレートモノマーのうちの少なくともいずれか1種、及び、光重合開始剤を含む導電性樹脂組成物及びこの導電性樹脂組成物を用いて形成される導電回路を提供する。
【選択図】なし
Description
(カルボキシル基含有樹脂)
カルボキシル基含有樹脂としては、分子中にカルボキシル基を含有している公知慣用の樹脂化合物を使用できる。
カルボキシル基含有樹脂としては、二重結合を含むカルボキシル基含有感光性樹脂でもよいが、二重結合を含まないカルボキシル基含有樹脂が好ましい。二重結合を含まないカルボキシル基含有樹脂は、アクリレートモノマーと反応しないため、分子間結合が形成されない。そのため、カルボキシル基含有樹脂は、分子量が大きくならないので、現像時に容易に除去される。その結果、導電性粉末が密になり、導電パターン膜の比抵抗値を下げることができる。
(2)無水マレイン酸などの不飽和二重結合を有する酸無水物と、それ以外の不飽和二重結合を有する化合物とを共重合することにより得られるカルボキシル基含有樹脂、
(3)不飽和二重結合を有する酸無水物と、それ以外の不飽和二重結合を有する化合物の共重合体に、水酸基を有する化合物を反応させて得られるカルボキシル基含有樹脂、
(4)エポキシ基と不飽和二重結合を有する化合物と不飽和二重結合を有する化合物の共重合体に、飽和カルボン酸を反応させ、生成した2級の水酸基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樹脂。
(5)水酸基含有ポリマー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樹脂、
が挙げられるが、これらに限定されるものではない。
なお、本明細書において、(メタ)アクリル酸とは、アクリル酸、メタクリル酸及びそれらの混合物を総称する用語で、他の類似の表現についても同様である。
また、上記カルボキシル基含有樹脂の酸価は、40〜200mgKOH/gの範囲であることが好ましく、より好ましくは45〜120mgKOH/gの範囲である。カルボキシル基含有樹脂の酸価が40mgKOH/g未満であるとアルカリ現像が困難となり、一方、200mgKOH/gを超えると現像液による露光部の溶解が進むために、必要以上にラインが痩せたり、場合によっては、露光部と未露光部の区別なく現像液で溶解剥離してしまい、正常な導電パターンの描画が困難となるので好ましくない。
まず、導電性粉末の材質は、導電性樹脂組成物において導電性を付与するものであればいかなるものでも用いることができる。このような導電性粉末としては、Ag、Au、Pt、Pd、Ni、Cu、Al、Sn、Pb、Zn、Fe、Ir、Os、Rh、W、Mo、Ru等を挙げることができ、これらの中でもAgが好ましい。これらの導電性粉末は、上記成分単体の形態で用いてもよいが、合金や、酸化物の形態で用いてもよい。さらに、酸化錫(SnO2)、酸化インジウム(In2O3)、ITO(Indium Tin Oxide)などを用いることもできる。なお、導電性粉末としては、カーボンブラック、グラファイト、カーボンナノチューブなどの炭素粉でもよい。ただし、光透過性が低下するため、注意を要する。
4官能基のアクリレートモノマーとして、ペンタエリスリトールテトラアクリレート、ペンタエリスリトールテトラメタクリレート等が挙げられる。
X1は、アクリロイルオキシ基を含む基を表す。
Z1はアルキレン基を表す。
光重合開始剤としては、特に限定されず、ベンゾイン系、フォスフィンオキサイド系でもよいが、下記一般式(V)で表される基を有するオキシムエステル系、又は、下記一般式(VI)で表される基を有するアセトフェノン系光重合開始剤を使用することが好ましい。
本発明の導電性樹脂組成物は、本発明の効果を更に向上させるために、或いは本発明の効果を阻害しない範囲で更に別の効果を発揮させるために、上述したカルボキシル基含有樹脂、導電性粉末、4官能基のアクリレートモノマー、及び、光重合開始剤とともに、以下に例示する他の成分を含むことができる。
有機酸としては、芳香環を持たない有機酸が好ましい。芳香環を持たない有機酸を配合することにより、有機酸自体の光吸収性が抑制され、相対的に4官能基のアクリレートモノマーの光反応性が向上し、優れた解像性を得ることができる。
分散剤を配合することで、導電性樹脂組成物の分散性、沈降性を改善することができる。
光重合禁止剤を添加することで、露光による導電性樹脂組成物内部でおこるラジカル重合の内、重合禁止剤の種類およびその添加量に応じた一定量のラジカル重合を抑制できる。これにより散乱光のような弱い光に対しての光反応を抑制することができる。よって、より微細な導電パターン膜のラインをシャープに形成することができるため、好ましく用いることができる。光重合禁止剤は、光重合禁止剤として使用できるものであれば特に制限はなく、例えば、p−ベンゾキノン、ナフトキノン、ジ−t−ブチル・パラクレゾール、ヒドロキノンモノメチルエーテル、α−ナフトール、アセトアニジンアセテート、ヒドラジン塩酸塩、トリメチルベンジルアンモニウムクロリド、ジニトロベンゼン、ピクリン酸、キノンジオキシム、ピロガロール、タンニン酸、レゾルミン、クペロン、フェノチアジン、などが挙げられる。
本発明の導電性樹脂組成物には、その塗膜の物理的強度等を上げるために、必要に応じて、フィラーを配合することができる。このようなフィラーとしては、公知慣用の無機又は有機フィラーが使用できるが、特に硫酸バリウム、シリカ、ハイドロタルサイト及びタルクが好ましく用いられる。
本発明の導電性樹脂組成物には、耐熱性を付与するために、熱硬化性成分を加えることができる。本発明に用いられる熱硬化性成分としては、メラミン樹脂、ベンゾグアナミン樹脂などのアミン樹脂、ブロックイソシアネート化合物、シクロカーボネート化合物、多官能エポキシ化合物、多官能オキセタン化合物、エピスルフィド樹脂、メラミン誘導体などの公知慣用の熱硬化性樹脂が使用できる。特に好ましいのは分子中に2個以上の環状エーテル基及び/又は環状チオエーテル基(以下、環状(チオ)エーテル基と略す)を有する熱硬化性成分である。
た場合、保存安定性が低下して、好ましくない。
本発明の導電性樹脂組成物に、上記分子中に2つ以上の環状(チオ)エーテル基を有する熱硬化性成分を使用する場合、熱硬化触媒を含有することが好ましい。そのような熱硬化触媒としては、例えば、イミダゾール、2−メチルイミダゾール、2−エチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、4−フェニルイミダゾール、1−シアノエチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾール等のイミダゾール誘導体;ジシアンジアミド、ベンジルジメチルアミン、4−(ジメチルアミノ)−N,N−ジメチルベンジルアミン、4−メトキシ−N,N−ジメチルベンジルアミン、4−メチル−N,N−ジメチルベンジルアミン等のアミン化合物、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド等のヒドラジン化合物;トリフェニルホスフィン等のリン化合物などが挙げられる。また、市販されているものとしては、例えば四国化成工業社製の2MZ−A、2MZ−OK、2PHZ、2P4BHZ、2P4MHZ(いずれもイミダゾール系化合物の商品名)、サンアプロ社製のU−CAT(登録商標)3503N、U−CAT3502T(いずれもジメチルアミンのブロックイソシアネート化合物の商品名)、DBU、DBN、U−CATSA102、U−CAT5002(いずれも二環式アミジン化合物及びその塩)などが挙げられる。特に、これらに限られるものではなく、エポキシ樹脂やオキセタン化合物の熱硬化触媒、もしくはエポキシ基及び/又はオキセタニル基とカルボキシル基の反応を促進するものであればよく、単独で又は2種以上を混合して使用してもかまわない。また、グアナミン、アセトグアナミン、ベンゾグアナミン、メラミン、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン、2−ビニル−2,4−ジアミノ−S−トリアジン、2−ビニル−4,6−ジアミノ−S−トリアジン・イソシアヌル酸付加物、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン・イソシアヌル酸付加物等のS−トリアジン誘導体を用いることもでき、好ましくはこれら密着性付与剤としても機能する化合物を前記熱硬化触媒と併用する。
熱重合禁止剤は、本発明の導電性樹脂組成物の熱的な重合または経時的な重合を防止するために用いることができる。熱重合禁止剤としては例えば、4−メトキシフェノール、ハイドロキノン、アルキルまたはアリール置換ハイドロキノン、t−ブチルカテコール、ピロガロール、2−ヒドロキシベンゾフェノン、4−メトキシ−2−ヒドロキシベンゾフェノン、塩化第一銅、フェノチアジン、クロラニル、ナフチルアミン、β−ナフトール、2,6−ジ−t−ブチル−4−クレゾール、2,2’−メチレンビス(4−メチル−6−t−ブチルフェノール)、ピリジン、ニトロベンゼン、ジニトロベンゼン、ピクリン酸、4−トルイジン、メチレンブルー、銅と有機キレート剤反応物、サリチル酸メチル、及びフェノチアジン、ニトロソ化合物、ニトロソ化合物とAlとのキレートなどが挙げられる。
本発明の導電性樹脂組成物において、感度を向上するために、連鎖移動剤として公知のNフェニルグリシン類、フェノキシ酢酸類、チオフェノキシ酢酸類、メルカプトチアゾール等を用いることができる。連鎖移動剤の具体例を挙げると、例えば、メルカプト琥珀酸、メルカプト酢酸、メルカプトプロピオン酸、メチオニン、システイン、チオサリチル酸及びその誘導体等のカルボキシル基を有する連鎖移動剤;メルカプトエタノール、メルカプトプロパノール、メルカプトブタノール、メルカプトプロパンジオール、メルカプトブタンジオール、ヒドロキシベンゼンチオール及びその誘導体等の水酸基を有する連鎖移動剤;1−ブタンチオール、ブチル−3−メルカプトプロピオネート、メチル−3−メルカプトプロピオネート、2,2−(エチレンジオキシ)ジエタンチオール、エタンチオール、4−メチルベンゼンチオール、ドデシルメルカプタン、プロパンチオール、ブタンチオール、ペンタンチオール、1−オクタンチオール、シクロペンタンチオール、シクロヘキサンチオール、チオグリセロール、4,4−チオビスベンゼンチオール等である。
本発明の導電性樹脂組成物には、公知慣用の成分、例えば増粘剤、消泡・レベリング剤、カップリング剤、酸化防止剤、防錆剤等を、必要に応じて適宜配合することができることは勿論である。
次に、本発明に係る導電性樹脂組成物を用いて導電回路を形成する方法の一例について説明する。
本発明の導電性樹脂組成物に関し、上述した各必須成分、ならびに任意成分との混練分散は、三本ロールやブレンダー等の機械が用いられる。
こうして分散された導電性樹脂組成物は、スクリーン印刷法、バーコーター、ブレードコーターなど適宜の塗布方法で基材上に塗布される。次いで指触乾燥性を得るために熱風循環式乾燥炉、遠赤外線乾燥炉等で、カルボキシル基含有樹脂が熱分解しない温度、例えば約60〜120℃で5〜40分程度乾燥させて有機溶剤を蒸発させ、タックフリーの塗膜を得る。
(配合成分)
[カルボキシル基含有樹脂]
合成例1
温度計、攪拌機、滴下ロート、及び還流冷却器を備えたフラスコに、メチルメタクリレートとメタアクリル酸を0.87:0.13のモル比で仕込み、溶媒としてジプロピレングリコールモノメチルエーテル、触媒としてアゾビスイソブチロニトリルを入れ、窒素雰囲気下、80℃で6時間攪拌し、カルボキシル基含有樹脂溶液を得た。このカルボキシル基含有樹脂は、質量平均分子量が約10,000、酸価が74mgKOH/gであった。なお、得られたカルボキシル基含有樹脂の質量平均分子量は、(株)島津製作所製ポンプLC−6ADと昭和電工(株)製カラムShodex(登録商標)KF−804,KF−803,KF−802を三本つないだ高速液体クロマトグラフィーにより測定した。以下、このカルボキシル基含有樹脂溶液を、A−1ワニスと称す。なお、このカルボキシル基含有樹脂は、二重結合を含まず、かつ、芳香環を含んでいない。
球状の導電性粉末:Ag粉末(最大粒径30μm以下、平均粒径2μm(SEM)))
針状の導電性粉末:Ag粉末(最大粒径30μm以下、平均粒径2μm(SEM)))
[アクリレートモノマー]
単官能アクリレートモノマー:商品名;フェノールEO変性アクリレート
2官能基のアクリレートモノマー:商品名;KAYARAD HX-220(日本化薬社製)
3官能基のアクリレートモノマー:商品名;アロニックス M-350(東亜合成社製)
4官能基のアクリレートモノマー:商品名;NKオリゴU-4HA(新中村社製)
6官能アクリレートモノマー:ジペンタエリスリトールヘキサアクリレート(日本化薬株式会社製)
[光重合開始剤]
商品名 :IRGACURE 379EG(BASFジャパン株式会社製),2-(ジメチルアミノ)-2-[(4-メチルフェニル)メチル]-1-[4-(4-モルホリニル)フェニル]-1-ブタノン
[有機酸]
2,2‘−チオ二酢酸
[分散剤]
商品名 DISPERBYK-111(ビックケミー・ジャパン株式会社製)
[実施例、参考例および比較例の説明]
以下の表1に示すように、実施例1〜12は4官能基アクリレートモノマーを配合したものであり、参考例1、3、5は、2官能基アクリレートモノマーを配合したものであり、参考例2、4、6は、3官能基アクリレートモノマーを配合したものである。これら実施例、参考例のうち、実施例1〜3、8〜10、参考例1,2は、球状の導電性粉末(Ag)の配合量を変えて添加したものである。実施例4〜6、11、参考例3、4は、針状の導電性粉末(Ag)の配合量を変えて添加したものである。実施例7、12、参考例5、6は、球状及び針状の導電性粉末を混合して配合したものである。
このようにして得られた実施例1〜12、参考例1〜6、比較例1〜8の各導電性樹脂組成物について、解像性、比抵抗値を評価した。その評価方法は以下のとおりである。
試験片作成:
ポリエステル樹脂製の基材上に、評価用の各導電性樹脂組成物を300メッシュのポリエステルスクリーンを用いて全面に塗布し、次いで、熱風循環式乾燥炉に90℃で30分間乾燥して指触乾燥性の良好な塗膜を形成した。その後、光源として高圧水銀灯を用い、ネガマスクを介して、導電性樹脂組成物上の積算光量が200mJ/cm2となるようにパターン露光した後、液温30℃の0.4質量%Na2CO3水溶液を用いて現像を行い、水洗した。最後に、130℃×30分で乾燥し、導電パターン膜を形成した試験片を作成した。
Claims (6)
- カルボキシル基含有樹脂、導電性粉末、4官能基のアクリレートモノマー、及び、光重合開始剤を含むことを特徴とする導電性樹脂組成物。
- 前記カルボキシル基含有樹脂は、二重結合を含まないことを特徴とする請求項1〜4のいずれかに記載の導電性樹脂組成物。
- 基材上に、請求項1〜5のいずれかに記載の導電性樹脂組成物を用いて形成されてなる導電回路。
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JP2013136727A (ja) * | 2011-11-29 | 2013-07-11 | Taiyo Ink Mfg Ltd | 導電性樹脂組成物及び導電回路 |
JP2013210498A (ja) * | 2012-03-30 | 2013-10-10 | Taiyo Holdings Co Ltd | 感光性導電ペーストおよび導電回路 |
JP5409954B1 (ja) * | 2013-07-29 | 2014-02-05 | 太陽インキ製造株式会社 | 導電性樹脂組成物及びその硬化物 |
JP2014163987A (ja) * | 2013-02-21 | 2014-09-08 | Taiyo Ink Mfg Ltd | 導電性樹脂組成物及び導電回路 |
JP2015184626A (ja) * | 2014-03-26 | 2015-10-22 | 東レ株式会社 | 感光性樹脂組成物、それからなる感光性樹脂ペーストならびにそれらを硬化させて得られる硬化膜およびそれを有する電極回路 |
KR20160117135A (ko) | 2015-03-31 | 2016-10-10 | 다이요 잉키 세이조 가부시키가이샤 | 도전성 수지 조성물 및 도전 회로 |
KR20190061024A (ko) | 2016-09-30 | 2019-06-04 | 다이요 잉키 세이조 가부시키가이샤 | 광경화성 수지 조성물, 드라이 필름, 경화물 및 프린트 배선판 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2013136727A (ja) * | 2011-11-29 | 2013-07-11 | Taiyo Ink Mfg Ltd | 導電性樹脂組成物及び導電回路 |
JP2013210498A (ja) * | 2012-03-30 | 2013-10-10 | Taiyo Holdings Co Ltd | 感光性導電ペーストおよび導電回路 |
JP2014163987A (ja) * | 2013-02-21 | 2014-09-08 | Taiyo Ink Mfg Ltd | 導電性樹脂組成物及び導電回路 |
JP5409954B1 (ja) * | 2013-07-29 | 2014-02-05 | 太陽インキ製造株式会社 | 導電性樹脂組成物及びその硬化物 |
JP2015184626A (ja) * | 2014-03-26 | 2015-10-22 | 東レ株式会社 | 感光性樹脂組成物、それからなる感光性樹脂ペーストならびにそれらを硬化させて得られる硬化膜およびそれを有する電極回路 |
KR20160117135A (ko) | 2015-03-31 | 2016-10-10 | 다이요 잉키 세이조 가부시키가이샤 | 도전성 수지 조성물 및 도전 회로 |
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