JP2014101412A - 導電回路形成用導電性樹脂組成物及び導電回路 - Google Patents
導電回路形成用導電性樹脂組成物及び導電回路 Download PDFInfo
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- JP2014101412A JP2014101412A JP2012252617A JP2012252617A JP2014101412A JP 2014101412 A JP2014101412 A JP 2014101412A JP 2012252617 A JP2012252617 A JP 2012252617A JP 2012252617 A JP2012252617 A JP 2012252617A JP 2014101412 A JP2014101412 A JP 2014101412A
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/09—Use of materials for the conductive, e.g. metallic pattern
- H05K1/092—Dispersed materials, e.g. conductive pastes or inks
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/16—Printed circuits incorporating printed electric components, e.g. printed resistor, capacitor, inductor
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- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Conductive Materials (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacturing Of Electric Cables (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
【解決手段】カルボキシル基含有樹脂、導電性粉末、多官能(メタ)アクリレートモノマー、光重合開始剤、及び、ブロックイソシアネート化合物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、(メタ)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。
(メタ)アクリレートモノマーとして、多官能(メタ)アクリレートモノマー(2官能以上の(メタ)アクリレートモノマー)を用いる。多官能(メタ)アクリレートモノマーを用いる理由は、官能基の数が1つの場合よりも、光反応性が向上して解像性が優れるためである。
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。
(ブロックイソシアネート化合物)
導電性樹脂組成物から得られる硬化膜の強靭性及び下地基材との密着性を向上させるために1分子内にブロック化イソシアネート基を有する化合物、すなわちブロックイソシアネート化合物などが挙げられる。
上記の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。
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(メタ)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、アセトアミジンアセテート、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、レゾルジン、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環状チオエーテル基の少なくとも何れか1種(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。
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オキセタニル基の少なくとも何れか1種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。
これらの工程では、500℃という高温で焼成しないので、基材として、耐熱性のない樹脂製の基材を使用することができる。具体的には、樹脂製の基材としては、例えば、ポリイミド、ポリエチレンテレフタレート(PET)、ポリブチレンテレフタレート(PBT)、ポリエチレンナフタレート(PEN)のようなポリエステル系樹脂、ポリエーテルサルフォン(PES)、ポリスチレン(PS)、ポリメチルメタクリレート(PMMA)、ポリカーボネート(PC)、ポリアミド(PA)、ポリプロピレン(PP)、ポリフェニレンオキサイド(PPO)等を挙げることができ、好適には、ポリエステル系樹脂を用いることができる。なお、ガラス基板等でもよい。
(配合成分)
[二重結合を含まない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)))
[アクリレートモノマー]
2官能(メタ)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(メタ)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(メタ)アクリレートモノマー:商品名;NKオリゴU-4HA(新中村化学社製)
6官能(メタ)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(日本化薬社製)
[光重合開始剤]
商品名 :IRGACURE 379EG(BASFジャパン社製),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
[ブロックイソシアネート]
商品名 7982(Baxenden社製)イソシアネートHDI3量体 ブロック剤 Dimethylpyrazole
[有機酸]
2,2‘−チオ二酢酸
[分散剤]
商品名 DISPERBYK-111(ビックケミー・ジャパン社製)
(評価方法)
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80℃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、140℃×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。
で、優れた導電性を確保し得る導電回路形成用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ことにある。
Claims (9)
- カルボキシル基含有樹脂、導電性粉末、多官能アクリレートモノマー、光重合開始剤、及び、ブロックイソシアネートを含むことを特徴とする導電性樹脂組成物。
- 前記多官能アクリレートモノマーは、4官能アクリレートモノマーであることを特徴とする請求項1に記載の導電性樹脂組成物。
- 前記光重合開始剤は、オキシムエステル系であることを特徴とする請求項1〜5のいずれかに記載の導電性樹脂組成物。
- 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1〜6のいずれかに記載の導電性樹脂組成物。
- 前記二重結合を含まないカルボキシル基含有樹脂は、さらに、芳香環を含まないことを特徴とする請求項7に記載の導電性樹脂組成物。
- 基材上に、請求項1〜8のいずれかに記載の導電性樹脂組成物を、塗布、乾燥して形成されてなる導電回路。
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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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JPWO2015040908A1 (ja) * | 2013-09-20 | 2017-03-02 | 東洋紡株式会社 | 感光性導電ペースト、導電性薄膜、電気回路、及びタッチパネル |
TW201539483A (zh) * | 2014-04-02 | 2015-10-16 | Toyo Boseki | 感光性導電糊劑、導電性薄膜、電路及觸控面板 |
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