JP6528776B2 - 凹パターンを有する構造体の製造方法、樹脂組成物、導電膜の形成方法、電子回路及び電子デバイス - Google Patents
凹パターンを有する構造体の製造方法、樹脂組成物、導電膜の形成方法、電子回路及び電子デバイス Download PDFInfo
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- JP6528776B2 JP6528776B2 JP2016547445A JP2016547445A JP6528776B2 JP 6528776 B2 JP6528776 B2 JP 6528776B2 JP 2016547445 A JP2016547445 A JP 2016547445A JP 2016547445 A JP2016547445 A JP 2016547445A JP 6528776 B2 JP6528776 B2 JP 6528776B2
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Description
本発明の構成例は以下のとおりである。
(i)酸解離性基を有する重合体及び酸発生剤を含む樹脂組成物を用いて、構造体の非平坦面に塗膜を形成する工程
(ii)前記塗膜の一部の所定部分に放射線照射を行うことにより凹部を形成する工程
[7] 前記酸解離性基が、下記式(1−1)及び(1−2)で示される基からなる群より選ばれる少なくとも1つの基を有する、[1]〜[6]のいずれかに記載の製造方法。
[9] 前記樹脂組成物が、下記式(2)〜(5)で示される構成単位の群から選ばれる少なくとも1つを有する、[1]〜[8]のいずれかに記載の製造方法。
[11] フッ素原子を含む酸解離性基を有する重合体、及び酸発生剤を含有する樹脂組成物。
[12] アセタール結合及びヘミアセタールエステル結合からなる群より選ばれる少なくとも1つの結合を含む酸解離性基を有する重合体、並びに、酸発生剤を含有する樹脂組成物。
[15] [14]に記載の電子回路を有する、電子デバイス。
本発明に係る凹パターンを有する構造体の製造方法は、下記工程(i)及び(ii)を含み、該凹パターンが、下記工程(i)で得られる塗膜の膜厚に対して、5%以上90%未満薄い膜厚であることを特徴とする。
(i)酸解離性基を有する重合体及び酸発生剤を含む樹脂組成物を用いて、構造体の非平坦面に塗膜を形成する工程
(ii)前記塗膜の一部の所定部分に放射線照射を行うことにより凹部を形成する工程
従って、本発明の製造方法は、所望の凹パターンを有する構造体を、容易に、安価に、大幅な工程の簡略化及びプロセス上の負荷を低減しながら製造できる等の点から、現像工程を含まないことが好ましい。
本発明によれば、放射線照射を経て凹パターンを形成するため、現像工程を行わず、放射線の当たりにくい箇所に集中的に放射線照射したり、過剰に放射線を照射することで、それほどバラツキがなく均一な凹パターンを形成することができる。
得られる凹パターンがこのような形状を有していると、該塗膜に導電膜形成用組成物を塗布等する際に、塗膜表面の凹凸の段差により、凹パターンから該組成物が溢れ出にくく、また、凹パターン以外の箇所に該組成物が残りにくくなるため、多量の導電膜形成用組成物を塗布等することができ、多量の導電膜形成用組成物を用いても高精細な導電膜(膜幅50μm以下の導電膜(パターン))を得ることができる。
放射線未照射部及び凹パターンの膜厚は、具体的には、下記実施例に記載の方法で測定することができる。
前記接触角差は、具体的には、下記実施例に記載の方法で測定することができる。
また、接触角を測定する際に、テトラデカンを用いたのは、テトラデカンが導電膜形成用組成物に一般的に使用され、かつ揮発しにくく、接触角を測定することに適しているためである。
工程(i)は、酸解離性基を有する重合体及び酸発生剤を含む樹脂組成物を用いて、構造体の非平坦面に塗膜を形成する工程であり、好ましくは樹脂組成物を構造体の非平坦面に設け、次いで、該組成物を加熱(プレベーク)することにより、塗膜を形成する工程である。
工程(i)において、前記樹脂組成物を用いることにより下記工程(ii)等において現像工程を行うことなく、構造体上に凹部を形成することができる。
尚、前記樹脂組成物については、以下で具体的に説明する。
このような構造体としては、例えば、瓦状の構造体、凸部及び/又は凹部を有する構造体、筒状の構造体、球状の構造体が挙げられる。
尚、本発明では、立方体や直方体などの角柱体の少なくとも2面に前記樹脂組成物を塗布等する場合、該塗布等する面は非平坦面であるため、本発明では、このような角柱体も、その少なくとも2面に前記樹脂組成物が塗布等される場合には、工程(i)における、非平坦面を有する構造体とする。
本発明によれば、これら立体構造物に簡便に凹パターンを形成することができ、更に、該凹パターン上に導電膜を形成することで、省スペースによる小型化、スリム化及び軽量化された導電膜付構造体を得ることができ、また、得られる導電膜付構造体は、高機能化が期待される。
尚、本発明において、例えば、立方体や直方体である構造体表面にこのような前処理をすることにより、表面が粗面化されたり、微小な凹凸が形成された表面は、前記「非平坦面」ではなく、非平坦面か否かは、表面を巨視的にみて判断する。
工程(ii)は、工程(i)で形成した塗膜の一部の所定部分に放射線照射を行うことにより凹部を形成する工程である。
工程(ii)では、構造体上の塗膜の一部に放射線が照射され、放射線照射部と放射線未照射部とを有する塗膜が形成される。
この時、酸解離性基がフッ素原子を含んでいれば、工程(i)で得られた塗膜及び放射線未照射部は撥液性を示すが、放射線照射部(凹部)は酸解離性基の消失に伴い、放射線未照射部に比べ親液性となる。
また、放射線照射は、線幅の狭い凹部を形成できる等の点から、工程(i)で形成した塗膜側から放射線を照射することが好ましい。
本発明では、前記工程(ii)で形成された凹部が、構造体上に形成された凹パターンであってもよいが、前記凹部のくぼみを更に深化させる(凹部の膜厚を更に薄くする)等の点から、本発明の製造方法は、工程(ii)で得られた放射線照射後の塗膜を加熱する工程(iii)を含むことが好ましい。
この工程(iii)を行う場合には、この工程により、凹パターンを有する構造体が製造される。
本発明の導電膜の形成方法は、前記凹パターンを有する構造体の製造方法で形成された凹パターン上に、導電膜形成用組成物を用いて導電膜を形成する工程を含むことを特徴とする。
この導電膜の形成方法によれば、高精細な導電膜(配線)を容易に、非平坦面を有する構造体上に形成することができ、従来の方法では容易に形成することができなかった、幅10μm以下、例えば、1μm程度の導電膜(配線)も非平坦面を有する構造体上に容易に形成することができる。
尚、導電膜形成用組成物については、以下で具体的に説明する。
また、加熱時間も特に制限されないが、1〜120分間が好ましく、3〜60分間がより好ましい。
本発明の電子回路は、前記導電膜の形成方法で形成された導電膜を有し、好ましくは、前記導電膜の形成方法で形成された導電膜と前記構造体との積層体を有する。つまり、本発明の電子回路は、非平坦面に、5%以上90%未満薄い膜厚の部分(凹パターン部)を有する塗膜が形成された構造体と、該凹パターン部上に形成された導電膜とを有する。
また、本発明の電子回路は、前記導電膜の形成方法で形成された導電膜と構造体との積層体に、従来公知の層、例えば、導電膜を保護する保護膜や絶縁膜をさらに積層したものであってもよい。
前記電子デバイスとしては、例えば、タッチパネル、液晶ディスプレイ、携帯電話等の携帯情報機器、デジタルカメラ、有機ディスプレイ、有機EL照明、各種センサーやウェアラブルデバイスが挙げられる。
前記樹脂組成物は、酸解離性基を有する重合体(以下「[A]重合体」ともいう。)及び酸発生剤(以下「[C]酸発生剤」ともいう。)を含有する組成物である。
このような組成物によれば、該組成物から形成される塗膜が、放射線の照射及び必要により行われる加熱により、揮発、分解するため好ましい。
このような樹脂組成物は、前記構造体上で導電膜形成用組成物の滲みを抑え、高精細なパターンを形成するための下地層形成用組成物として、また、導電膜(配線)と前記構造体との密着性を向上させる下地層形成用組成物として、好適に使用することができる。
前記樹脂組成物は、[C]酸発生剤の補助材料として、更に、増感剤(以下「[D]増感剤」ともいう。)を含んでもよく、[C]酸発生剤からの酸の拡散抑制材料としてクエンチャー(以下「[E]クエンチャー」ともいう。)を含んでもよい。
また、前記樹脂組成物は、[A]重合体以外のエチレン性不飽和結合を有する重合性化合物(以下「[F]重合性化合物」ともいう。)を含んでもよく、感放射線性重合開始剤(以下「[G]感放射線性重合開始剤」ともいう。)を含んでもよい。
さらに、前記樹脂組成物には、本発明の効果を損なわない限り、その他の任意成分を配合することができる。
前記[A]重合体は、酸により、解離する性質を有する基を含有する重合体であれば特に制限されない。
これらの化合物(以下「化合物(a)」ともいう。)、特に水酸基を有する化合物の水酸基に保護基が導入された化合物は、熱による保護基の脱離が生じ難いという性質を備え、一方で、放射線照射による保護基の脱離の制御ができるという性質を備えるため、[A]重合体として好適に使用できる。さらに、化合物(a)は、後述する[C]酸発生剤との組み合わせによって、放射線照射による、より高精度の保護基の脱離の制御が可能となるため好ましい。
また、前駆体となる化合物としてモノマーを用いる方法では、前駆体となるモノマーが分子内に水酸基又はカルボキシル基を含有し、前駆体となるモノマーの水酸基又はカルボキシル基に前記化合物(1)を反応させた後、得られたモノマーを重合させることで[A]重合体を得ることができる。
以下、[A]重合体を得るための2つの方法について、より具体的に説明する。
この方法では、水酸基又はカルボキシル基を有するモノマーを重合して水酸基又はカルボキシル基を有する重合体(前駆体)を得て、その後、前駆体となる重合体の水酸基又はカルボキシル基に前記化合物(1)を反応させて、[A]重合体を得ることができる。また、従来公知の方法、例えば、フェノールとホルムアルデヒドとを反応させる方法で水酸基又はカルボキシル基を有する重合体(前駆体)を得て、その後、前駆体となる重合体の水酸基又はカルボキシル基に前記化合物(1)を反応させて、[A]重合体を得ることができる。
例えば、水酸基又はカルボキシル基を有する重合体を適宜の有機溶媒中に溶解した後、重合体の有する水酸基又はカルボキシル基に対して等モル又は過剰量の前記化合物(1)を加え、得られた反応混合物を0℃から室温(25℃)程度の温度に冷却した後、前記有機溶媒と同じ溶媒に溶解させた酸(例えば、シュウ酸溶液)を触媒として滴下し、滴下終了後、室温下で1時間〜24時間攪拌し、反応させる。反応終了後、有機溶剤を除去することにより、目的の[A]重合体を得ることができる。
この方法では、水酸基又はカルボキシル基を有するモノマーの水酸基又はカルボキシル基に前記化合物(1)を反応させて付加物を得て、該付加物を重合させることで、[A]重合体を得る。このような[A]重合体を得る方法は、公知の方法を参考にすることができる。例えば、特開2005−187609号公報に記載されているように、水酸基を有するモノマーの水酸基と化合物(1)のビニルエーテル基によってアセタール結合を生成して、又は、カルボキシル基を有するモノマーのカルボキシル基と前記化合物(1)のビニルエーテル基によってヘミアセタールエステル結合を生成して、付加物を形成する。次いで、得られた付加物を用いて、前記水酸基又はカルボキシル基を有する重合体の製造方法と同様にして、[A]重合体を得ることができる。
前記R5としては、前記RBで例示した基と同様の基等が挙げられる。
前記nとしては、0〜9の整数が好ましい。
[B]溶剤としては特に限定されないが、[A]重合体の他、後述する[C]酸発生剤及び[F]重合性化合物等の各成分を均一に溶解又は分散することができる溶剤が好ましい。
ベンジルアルコール等の芳香族アルコール類;
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル等のエチレングリコールモノアルキルエーテル類;
プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル等のプロピレングリコールモノアルキルエーテル類;
ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノブチルエーテル等のジプロピレングリコールモノアルキルエーテル類などを挙げることができる。
これらのアルコール系溶剤は、単独で又は2種以上を使用することができる。
[C]酸発生剤は、少なくとも放射線の照射によって酸を発生する化合物である。樹脂組成物が、[C]酸発生剤を含有することで、[A]重合体から酸解離性基を脱離させることができる。
[C]酸発生剤は、単独で用いてもよく、2種類以上を用いてもよい。
前記オキシムスルホネート化合物としては、下記式(5)で表されるオキシムスルホネート基を含む化合物が好ましい。
式(5−3)中、Xは、アルキル基、アルコキシ基又はハロゲン原子である。mは、0〜3の整数である。但し、Xが複数の場合、複数のXは同一であっても異なっていてもよい。
オニウム塩としては、例えば、ジフェニルヨードニウム塩、トリフェニルスルホニウム塩、アルキルスルホニウム塩、ベンジルスルホニウム塩、ジベンジルスルホニウム塩、置換ベンジルスルホニウム塩、ベンゾチアゾニウム塩、テトラヒドロチオフェニウム塩が挙げられる。
[C]酸発生剤として好ましいスルホンイミド化合物としては、例えば、N−(トリフルオロメチルスルホニルオキシ)スクシンイミド、N−(カンファスルホニルオキシ)スクシンイミド、N−(4−メチルフェニルスルホニルオキシ)スクシンイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)スクシンイミド、N−(4−フルオロフェニルスルホニルオキシ)スクシンイミド、N−(トリフルオロメチルスルホニルオキシ)フタルイミド、N−(カンファスルホニルオキシ)フタルイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)フタルイミド、N−(2−フルオロフェニルスルホニルオキシ)フタルイミド、N−(トリフルオロメチルスルホニルオキシ)ジフェニルマレイミド、N−(カンファスルホニルオキシ)ジフェニルマレイミド、4−メチルフェニルスルホニルオキシ)ジフェニルマレイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ジフェニルマレイミド、N−(4−フルオロフェニルスルホニルオキシ)ジフェニルマレイミド、N−(4−フルオロフェニルスルホニルオキシ)ジフェニルマレイミド、N−(フェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(ノナフルオロブタンスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(カンファスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(カンファスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)−7−オキサビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(カンファスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)ビシクロ[2.2.1]ヘプタン−5,6−オキシ−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(カンファスルホニルオキシ)ナフチルジカルボキシイミド、N−(4−メチルフェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(フェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(2−トリフルオロメチルフェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(4−フルオロフェニルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ペンタフルオロエチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ヘプタフルオロプロピルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ノナフルオロブチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(エチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(プロピルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ブチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ペンチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ヘキシルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ヘプチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(オクチルスルホニルオキシ)ナフチルジカルボキシイミド、N−(ノニルスルホニルオキシ)ナフチルジカルボキシイミド等が挙げられる
[C]酸発生剤として好ましいハロゲン含有化合物としては、例えば、ハロアルキル基含有炭化水素化合物、ハロアルキル基含有ヘテロ環状化合物が挙げられる。
[C]酸発生剤として好ましいジアゾメタン化合物としては、例えば、ビス(トリフルオロメチルスルホニル)ジアゾメタン、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(フェニルスルホニル)ジアゾメタン、ビス(p−トリルスルホニル)ジアゾメタン、ビス(2,4−キシリルスルホニル)ジアゾメタン、ビス(p−クロロフェニルスルホニル)ジアゾメタン、メチルスルホニル−p−トルエンスルホニルジアゾメタン、シクロヘキシルスルホニル(1,1−ジメチルエチルスルホニル)ジアゾメタン、ビス(1,1−ジメチルエチルスルホニル)ジアゾメタン、フェニルスルホニル(ベンゾイル)ジアゾメタン等が挙げられる。
[C]酸発生剤として好ましいスルホン化合物としては、例えば、β−ケトスルホン化合物、β−スルホニルスルホン化合物、ジアリールジスルホン化合物が挙げられる。
[C]酸発生剤として好ましいスルホン酸エステル化合物としては、例えば、アルキルスルホン酸エステル、ハロアルキルスルホン酸エステル、アリールスルホン酸エステル、イミノスルホネートが挙げられる。
[C]酸発生剤として好ましいカルボン酸エステル化合物としては、例えば、カルボン酸o−ニトロベンジルエステルが挙げられる。
前記樹脂組成物は、[D]増感剤を含有することができる。
フルオレセイン、エオシン、エリスロシン、ローダミンB、ローズベンガル等のキサンテン類;
キサントン、チオキサントン、ジメチルチオキサントン、ジエチルチオキサントン、イソプロピルチオキサントン、2,4−ジエチルチオキサンテン−9−オン等のキサントン類;
チアカルボシアニン、オキサカルボシアニン等のシアニン類;
メロシアニン、カルボメロシアニン等のメロシアニン類;
ローダシアニン類;
オキソノール類;
チオニン、メチレンブルー、トルイジンブルー等のチアジン類;
アクリジンオレンジ、クロロフラビン、アクリフラビン等のアクリジン類;
アクリドン、10−ブチル−2−クロロアクリドン等のアクリドン類;
アントラキノン等のアントラキノン類;
スクアリリウム等のスクアリリウム類;
スチリル類;
2−[2−[4−(ジメチルアミノ)フェニル]エテニル]ベンゾオキサゾール等のベーススチリル類;
7−ジエチルアミノ4−メチルクマリン、7−ヒドロキシ4−メチルクマリン、2,3,6,7−テトラヒドロ−9−メチル−1H,5H,11H[1]ベンゾピラノ[6,7,8−ij]キノリジン−11−オン等のクマリン類等が挙げられる。
前記樹脂組成物は、[E]クエンチャーを含有することができる。
[E]クエンチャーの含有量としては、[A]重合体100質量部に対して、0.001〜5質量部が好ましく、0.005〜3質量部がより好ましい。[D]増感剤の含有量を前記範囲にすることで、樹脂組成物の反応性を最適化できるため、前記工程(i)〜(ii)を経ることで高解像度な凹パターンを形成できる。
樹脂組成物は、[F]重合性化合物を含有することで、該組成物を硬化させることができる。
このような[F]重合性化合物としては、重合性が良好であり、樹脂組成物から得られる膜の強度が向上するという観点から、単官能、2官能又は3官能以上の(メタ)アクリル酸エステルが好ましい。
尚、単官能化合物とは、(メタ)アクリロイル基を1つ有する化合物のことをいい、2官能又は3官能以上の化合物とは、それぞれ、(メタ)アクリロイル基を2つ又は3つ以上有する化合物のことをいう。
[G]感放射線性重合開始剤は、放射線の照射を受けて、[F]重合性化合物の重合を促進する化合物である。したがって、樹脂組成物が[F]重合性化合物を含有する場合、[G]感放射線性重合開始剤を用いることが好ましい。
以上のアセトフェノン化合物は、単独で又は2種以上を使用することができる。
3−メルカプトプロピオン酸、3−メルカプトプロピオン酸メチル等の脂肪族モノチオール化合物;
ペンタエリストールテトラ(メルカプトアセテート)、ペンタエリストールテトラ(3−メルカプトプロピオネート)等の2官能以上の脂肪族チオール化合物を挙げることができる。
これらのチオール化合物は、単独で又は2種以上を使用することができる。
これらのチオール化合物の中でも、2−メルカプトベンゾチアゾールが特に好ましい。
[G]感放射線性重合開始剤の使用量は、[A]重合体100質量部に対して、好ましくは0.05〜50質量部、より好ましくは0.1〜20質量部である。[G]感放射線性重合開始剤の使用量を前記範囲内とすることによって、低露光量でも、高い放射線感度で塗膜の硬化を行うことができる。
前記樹脂組成物は、さらに、本発明の効果を損なわない限りその他の任意成分を含有することができる。
その他の任意成分としては、界面活性剤、保存安定剤、接着助剤、耐熱性向上剤等を挙げることができる。
その他の任意成分は、1種を単独で使用してもよいし、2種以上を使用してもよい。
前記導電膜形成用組成物は特に限定されるものではなく、導電膜を形成できるような組成物であればよく、流動性を持った液状のインク、ペーストであることが好ましい。
例えば、導電膜形成インク、導電膜形成ペースト、顔料や染料を含む着色性インク、着色性ペースト、有機半導体溶液や酸化物半導体分散体、有機EL発光体溶液や量子ドット、カーボンナノチューブ、グラフェン、カーボンブラック等のナノカーボンを含むインクが挙げられる。
これらのインク又はペーストは各種の印刷法、塗布法、浸漬法などにより塗膜の形成が可能であり、またその塗膜は、加熱されて導電性の導通性膜(導電膜)となる。
一方、本発明では、前記凹パターン上に導電膜を形成するため、前記低粘度の導電膜形成用組成物を用いても、該組成物の濡れ広がりや滲みが抑制され、高精細な導電膜を製造できる。
このため、本発明の効果がより発揮されるという点からは、前記低粘度の導電膜形成用組成物を用いることが好ましい。
前記金属塩は、その金属塩に含まれる金属イオンが前記還元剤により還元されて金属単体となる。そして、形成される導電膜において、導電性を発現させる役割を果たす。例えば、金属塩が銅塩である場合、銅塩に含まれる銅イオンは還元剤により還元され、銅単体となり、導電膜が形成される。
前記金属塩としては銅塩、銀塩が好ましい。
前記金属塩は、1種を単独で使用してもよいし、2種以上を使用してもよい。
例えば、硝酸銀、酢酸銀、酸化銀、アセチルアセトン銀、安息香酸銀、臭素酸銀、臭化銀、炭酸銀、塩化銀、クエン酸銀、フッ化銀、ヨウ素酸銀、ヨウ化銀、乳酸銀、亜硝酸銀、過塩素酸銀、リン酸銀、硫酸銀、硫化銀、及びトリフルオロ酢酸銀を挙げることができる。
前記導電膜形成用組成物は、金属塩に含まれる金属イオンを還元して金属単体とすることを目的として、前記金属塩とともに、還元剤を含有することが好ましい。還元剤は、用いられる金属塩に含まれる金属イオンに対し還元性を有していれば特に限定するものではない。
前記導電膜形成用組成物は、金属塩の還元析出速度を向上させる目的、又は、該組成物の粘度を調節する目的で、金属微粒子を含有することができる。
透過型電子顕微鏡(TEM)、電界放射型透過電子顕微鏡(FE−TEM)、電界放射型走査電子顕微鏡(FE−SEM)等の顕微鏡を用いて観測された視野の中から、任意の3箇所選択し、粒径測定に最も適した倍率で撮影する。得られた各々の写真から、任意に粒子を100個選択し、粒子の長軸をTEM、FE−TEM、FE−SEM等で測定し、測定倍率を除して粒子径を算出し、これらの値を算術平均することにより求めることができる。また、標準偏差については、前記観察時に個々の金属微粒子の粒子径と数により求めることができる。
前記導電膜形成用組成物は、該組成物の粘度を調節して導電膜の生産性を向上させる観点や、低抵抗で均一な導電膜を得る観点から、溶剤を含有することが好ましい。
以下の合成例で得られた重合体のポリスチレン換算の重量平均分子量(Mw)及び分子量分布(Mw/Mn)は、以下の条件で測定した。
・測定方法:ゲルパーミエーションクロマトグラフィー(GPC)法
・標準物質:ポリスチレン換算
・装置 :東ソー(株)製、商品名:HLC−8220
・カラム :東ソー(株)製ガードカラムHXL−H、TSK gel G7000HXL、TSK gel GMHXL 2本、TSK gel G2000HXLを順次連結したもの
・溶媒 :テトラヒドロフラン
・サンプル濃度:0.7質量%
・注入量 :70μL
・流速 :1mL/min
1H−NMRは、溶媒としてCDCl3を用い、核磁気共鳴装置(Bruker製、AVANCEIII AV400N)を用い、温度25℃の条件下で測定した。
[合成例1]
冷却管及び撹拌機を備えたフラスコに、ジメチル2,2’−アゾビス(2−メチルプロピオネート)8質量部、2,4−ジフェニル−4−メチル−1−ペンテン2質量部、及び、ジエチレングリコールジメチルエーテル200質量部を仕込んだ。引き続きメタクリル酸2−ヒドロキシエチル42質量部及びメタクリル酸ベンジル58質量部を仕込み、窒素雰囲気下で緩やかに攪拌しつつ、溶液の温度を80℃に上昇させ、この温度を4時間保持して重合することにより、共重合体である重合体(A−1)を含む溶液を得た(固形分濃度=34.6質量%、Mw=26000、Mw/Mn=2.2)。尚、固形分濃度は共重合体溶液の全質量に占める共重合体質量の割合を意味する。
冷却管及び撹拌機を備えたフラスコに、ジメチル2,2’−アゾビス(2−メチルプロピオネート)8質量部、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)2質量部、及び、プロピレングリコールモノメチルエーテル200質量部を仕込んだ。引き続きメタクリル酸2−ヒドロキシエチル75質量部及びメタクリル酸ベンジル25質量部を仕込み、窒素置換した後、緩やかに攪拌しつつ、溶液の温度を80℃に上昇させ、この温度を4時間保持して重合することにより、共重合体である重合体(A−2)を含有する溶液を得た。得られた溶液を大過剰のヘキサンに滴下し、沈殿物を乾燥させることで白色固体状の重合体(A−2)を得た(Mw=28000、Mw/Mn=2.3)。
冷却管及び撹拌機を備えたフラスコに、ジメチル2,2’−アゾビス(2−メチルプロピオネート)8質量部、2,4−ジフェニル−4−メチル−1−ペンテン2質量部、及び、プロピレングリコールモノメチルエーテル200質量部を仕込んだ。引き続きメタクリル酸30質量部及びメタクリル酸ベンジル70質量部を仕込み、窒素置換した後、緩やかに攪拌しつつ、溶液の温度を80℃に上昇させ、この温度を4時間保持して重合することにより、共重合体である重合体(A−3)を含有する溶液を得た。得られた溶液を大過剰のヘキサンに滴下し、沈殿物を乾燥させることで白色固体状の重合体(A−3)を得た(Mw=24000、Mw/Mn=2.2)。
冷却管及び撹拌機を備えたフラスコに、ジメチル2,2’−アゾビス(2−メチルプロピオネート)8質量部、2,4−ジフェニル−4−メチル−1−ペンテン2質量部、及び、プロピレングリコールモノメチルエーテル200質量部を仕込んだ。引き続き2−メタクリロイルオキシエチルコハク酸60質量部及びメタクリル酸ベンジル40質量部を仕込み、窒素置換した後、緩やかに攪拌しつつ、溶液の温度を80℃に上昇させ、この温度を4時間保持して重合することにより、共重合体である重合体(A−4)を含有する溶液を得た。得られた溶液を大過剰のヘキサンに滴下し、沈殿物を乾燥させることで白色固体状の重合体(A−4)を得た(Mw=23400、Mw/Mn=2.2)。
冷却管及び撹拌機を備えたフラスコに、ポリビニルフェノール(マルカリンカーS−4P 丸善石油化学(株))5質量部を加え、テトラヒドロフラン50質量部で溶かし、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン16質量部を加え、十分に攪拌した後にトリフルオロ酢酸0.50質量部を加え、窒素雰囲気下、60℃で9時間反応させた。続いて反応溶液を室温まで冷却し、ピリジン0.5質量部を加え、反応をクエンチした。得られた反応溶液を過剰量のメタノールに滴下することにより再沈殿精製を行い、続いて沈殿物を再度30質量部のテトラヒドロフランに溶解させた後、ヘキサンに滴下することにより再沈殿精製を行い、沈殿物を乾燥させることで白色固形状の共重合体として[A]重合体(P−5)を得た。得られた[A]重合体(P−5)について1H−NMRを用いて分析を行い、アセタール化が進行していることを確認した(化学シフト:5.48ppm、アセタール基C−H)。
冷却管及び撹拌機を備えたフラスコに、下記式で表されるフェノールノボラック樹脂P−200(荒川化学工業(株)製)5質量部を加え、テトラヒドロフラン60質量部で溶かし、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10−ヘプタデカフルオロ−1−ビニルオキシデカン20質量部を加え、十分に攪拌した後にトリフルオロ酢酸0.50質量部を加え、窒素雰囲気下、60℃で9時間反応させた。続いて反応溶液を室温まで冷却し、ピリジン0.5質量部を加え、反応をクエンチした。得られた反応溶液を過剰量のメタノールに滴下することにより再沈殿精製を行い、続いて沈殿物を再度30質量部のテトラヒドロフランに溶解させた後、ヘキサンに滴下することにより再沈殿精製を行い、沈殿物を乾燥させることで白色固形状の共重合体として[A]重合体(P−6)12.1質量部を得た。得られた[A]重合体(P−6)について1H−NMRを用いて分析を行い、アセタール化が進行していることを確認した(化学シフト:5.49ppm、アセタール基C−H)。
冷却管及び撹拌機を備えたフラスコに、メタクリル酸2−ヒドロキシエチル25質量部、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン101質量部、トリフルオロ酢酸(TFA)2.0質量部及びテトラヒドロフラン(THF)200質量部を仕込み、窒素雰囲気下、60℃で9時間保持して反応させた。冷却後、反応液にピリジン2.1質量部を加え、クエンチした。得られた反応液を水洗、分液し、ロータリーエバポレーターで溶剤を除去し、減圧蒸留により未反応成分を除去することによりアセタール化生成物(M−1)を得た。
冷却管及び撹拌機を備えたフラスコに、ヒドロキシフェニルメタクリレート25質量部、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン82質量部、トリフルオロ酢酸(TFA)1.6質量部及びテトラヒドロフラン(THF)200質量部を仕込み、窒素雰囲気下、60℃で9時間保持して反応させた。冷却後、反応液にピリジン1.7質量部を加え、反応をクエンチした。得られた反応液を水洗、分液し、ロータリーエバポレーターで溶剤を除去し、減圧蒸留により未反応成分を除去することによりアセタール化生成物(M−2)を得た。
冷却管及び撹拌機を備えたフラスコに、メタクリル酸2−(2−ビニロキシエトキシ)エチル(VEEM、(株)日本触媒製)25質量部、3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロオクタノール45質量部、パラトルエンスルホン酸ピリジニウム(PPTSA)1.6質量部及びテトラヒドロフラン(THF)200質量部を仕込み、窒素雰囲気下、室温で8時間保持して反応させた。反応終了後、反応液にピリジン0.7質量部を加え、反応をクエンチした。得られた反応液を水洗、分液し、ロータリーエバポレーターで溶剤を除去し、減圧蒸留により未反応成分を除去することによりアセタール化生成物(M−3)を得た。
実施例及び比較例で用いた各成分の詳細を以下に示す。
C−1:N−ヒドロキシナフタルイミド−トリフルオロメタンスルホン酸エステル
C−2:4,7−ジ−n−ブトキシ−1−ナフチルテトラヒドロチオフェニウム トリフルオロメタンスルホネート
C−3:CGI725 (BASF社製)
D−1:2−イソプロピルチオキサントン
D−2:2,4−ジエチルチオキサンテン−9−オン
E−1:2−フェニルベンゾイミダゾール
E−2:4−(ジメチルアミノ)ピリジン
F−1:ジペンタエリスリトールヘキサアクリレート
F−2:1,9−ノナンジオールジアクリレート
G−1:2−メチル−1−(4−メチルチオフェニル)−2−モルフォリノプロパン−1−オン(イルガキュア(登録商標)907、BASF社製)
G−2:2−ジメチルアミノ−2−(4−メチルベンジル)−1−(4−モルフォリン−4−イル−フェニル)−ブタン−1−オン(イルガキュア(登録商標)379、BASF社製)
G−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(登録商標)OXE02、BASF社製)
表1に示す種類、含有量の各成分を混合し、固形分濃度が10質量%となるように、それぞれ[B]溶剤として、プロピレングリコールモノメチルエーテルを加えた後、孔径0.5μmのメンブレンフィルター(メルクミリポア社製)でろ過することにより、各樹脂組成物を調製した。尚、表1中の「−」は該当する成分を使用しなかったことを表す。
実施例1〜9及び比較例1〜2で調製した各樹脂組成物を用いて膜形成を行い、以下の評価を実施した。結果を表2又は3に示す。
ポリカーボネート/AES(アクリロニトリル・エチレン−プロピレン−ジエン・スチレン)樹脂(CW50:テクノポリマー社製)からなる平板上に、実施例1〜9又は比較例1〜2で調製した樹脂組成物をそれぞれスピンナーで塗布した後、90℃のクリーンオーブン上で5分間プレベークすることにより0.5μm厚の塗膜を形成した。次いで、得られた塗膜に石英マスク(コンタクト)を介して高圧水銀ランプを用い(露光機:大日本科研社製MA−1400)、露光量を500mJ/cm2として放射線照射を行った。その後、クリーンオーブンを用い100℃で10分ベークすることにより、塗膜を形成した。
実施例1〜9で調製した樹脂組成物を用いた場合には、露光部(凹部)が親液部となり、露光部分以外(凸部)が撥液部となった、親液部と撥液部とによりパターニングされた膜(以下、「親撥パターニング膜」と称することがある。)が得られた。
前記[接触角]と同様の方法で得られた膜に関して、露光部(凹部)と未露光部(凸部)の膜厚を接触式膜厚計((株)キーエンス製:アルファステップIQ)で測定した。そして、未露光部(撥液部)の膜厚と露光部(親液部)の膜厚との差を算出し、下記式からの膜厚減少率(%)を算出することにより凹パターニング形成性を確認した。
膜厚減少率(%)=(撥液部の膜厚−親液部の膜厚)×100/撥液部の膜厚
実施例1〜9及び比較例1〜2で調製した樹脂組成物を用いて、立体構造物上での膜形成を行い、以下の評価を実施した。結果を表2に示す。
図1(A)〜(C)に示す形状の立体構造物a〜c上に、実施例1〜9又は比較例1〜2で調製した樹脂組成物をそれぞれスプレーコートした後、90℃のクリーンオーブン上で5分間ベークして溶剤を乾燥させ0.5μm厚の塗膜を形成した。次いで、得られた塗膜に、図2(A)〜(C)に示す形状の凹パターンを有する構造体が形成されるように、所望の遮光部と500μm幅の直線状の透過部を有するフィルムシールを貼った。該フィルムシールを貼った立体構造物に高圧水銀ランプ(露光機:(株)大日本科研製、MA−1400)を用い、塗膜の露光量が500mJ/cm2になるように放射線照射を行った。その後、フィルムシールを剥離し、クリーンオーブンを用い100℃で10分ベークすることにより、塗膜を形成した。
立体構造物bは、ポリカーボネート/AES樹脂(「CW50」:テクノポリマー社製)からなる立体構造物であり、この立体構造物の図1(B)における上面全体に樹脂組成物をスプレーコートした。
立体構造物cは、ポリカーボネート/ABS(アクリロニトリル・ブタジエン・スチレン)樹脂(「CK50」:テクノポリマー社製)からなる立体構造物であり、この立体構造物の表面全体に樹脂組成物をスプレーコートした。
[立体構造物への凹パターン形成]の評価と同様の方法で塗膜付立体構造物を作成した。この塗膜付立体構造物について、立体構造物が劣化しておらず、目視で確認可能な凹パターンが形成されていれば良好(○)、目視で確認可能な凹パターンが形成できていない場合や立体構造物に目視で膜荒れ、白化等が起こっていれば不良(×)として目視での外観の評価を行った。
[立体構造物への凹パターン形成]の評価と同様の方法で塗膜付立体構造物を作成した。この塗膜付立体構造物について、凹パターンを含む1cm角の四角状の塗膜部分にカッターナイフを用いて切り込みを入れ、該部分でテープ剥離試験(CT−18セロテープ、ニチバン(株)製)を実施し、塗膜と立体構造物との密着性を評価した。
剥離が生じなければ良好(○)と評価し、剥離が生じた場合を不良(×)として評価を行った。
前記[立体構造物への凹パターン形成]で得られた直線状の凹パターンを有する塗膜の凹パターン上に、銀ナノインクNPS−JL(ハリマ化成(株)製)を滴下し、該インクが流動し終わった後にクリーンオーブンで100℃で60分焼成することで銀配線を形成した。形成された銀配線について、500μm幅の直線状の銀配線が得られ、銀配線部の長さ10cm間隔の2点で2000型デジタルマルチメーター(ケースレー社製)を用いた抵抗を測定し、断線無く導通が確認できれば(○)、500μm幅の直線状の銀配線が得られなければ(×)として評価した。
尚、直線状の銀配線が得られているか否かは、光学顕微鏡(エクリプスL200D、(株)ニコン製)を用いて確認した。
前記[立体構造物への凹パターン形成]で得られた直線状の凹パターンを有する立体構造物を、銀ナノインクNPS−JL(ハリマ化成(株)製)中に3秒浸漬し、その後立体構造物を引き上げ、立体構造体a及びbを用いた場合には傾斜をつけて静置し(例えば、図2の(A)及び(B)において上面が床面に対し60°以上となるような角度で静置し)、立体構造体cを用いた場合には図2の(C)の向きで静置した。その後クリーンオーブンで100℃で60分焼成することで銀配線を形成した。形成された銀配線について、500μm幅の直線状の銀配線が得られ、銀配線部の長さ10cm間隔の2点で2000型デジタルマルチメーター(ケースレー社製)を用いた抵抗を測定し、断線無く導通が確認できれば(○)、500μm幅の直線状の銀配線が得られなければ(×)として評価した。
尚、直線状の銀配線が得られているか否かは、光学顕微鏡(エクリプスL200D、(株)ニコン製)を用いて確認した。
[金属配線形成:滴下法]及び[金属配線形成:ディップ法]の評価と同様の方法で銀配線付立体構造物を作成した。この銀配線付立体構造物について、銀配線が孤立した1cm長になるようカッターナイフで切り込みを入れ、該部分でテープ剥離試験(CT−18セロテープ、ニチバン(株)製)を実施し、銀配線と塗膜との密着性を評価した。
剥離が生じなければ良好(○)と評価し、剥離が生じた場合を不良(×)として評価を行った。
表2の結果から、塗布面が非平坦面である構造体に対し、実施例1〜9で調製された樹脂組成物を用いて形成された親撥パターニング膜は、比較例1〜2で調製された樹脂組成物を用いて形成された塗膜と比べ、良好な親撥性能、外観及び密着性を有し、所望の凹パターンを有することがわかった。すなわち、実施例1〜9で調製された樹脂組成物は、凹パターンを有する立体構造物の製造に好適に使用できることがわかった。
尚、立体構造物a〜c上に形成された塗膜の凹パターン部と放射線未照射部の膜厚及び接触角は、前記平板上の基板に形成した塗膜と同程度であると考えられる。
すなわち、実施例1〜9で調製された樹脂組成物は、凹パターンを有する立体構造物の凹パターン上に導電膜を形成するのに好適に使用できることがわかった。
20:立体構造物b
30:立体構造物c
12:塗膜付立体構造物a
14:凹パターン又は銀配線
22:塗膜付立体構造物b
24:凹パターン又は銀配線
32:塗膜付立体構造物c
34:凹パターン又は銀配線
Claims (12)
- 下記工程(i)及び(ii)を含み、下記工程(i)で得られる塗膜の膜厚に対して
、5%以上90%未満薄い膜厚の凹パターンを有する、構造体の製造方法。
(i)酸解離性基および下記式(2)〜(5)で示される構成単位の群から選ばれる
少なくとも1つを有する重合体、並びに、酸発生剤を含む樹脂組成物を用いて、構造体の非平坦面に塗膜を形成する工程
(ii)前記塗膜の一部の所定部分に放射線照射を行うことにより凹部を形成する工
程
- さらに、(iii)放射線照射後の塗膜を加熱する工程を含む、請求項1に記載の製
造方法。 - 前記非平坦面が、曲面及び凹凸面からなる群より選ばれる少なくとも1種の面を含む、請求項1又は2に記載の製造方法。
- 前記酸解離性基がフッ素原子を含む、請求項1〜3のいずれか一項に記載の製造方法。
- 凹パターン部と放射線未照射部とのテトラデカンに対する接触角差が30°以上である、請求項1〜4のいずれか一項に記載の製造方法。
- 前記酸解離性基が、アセタール結合及びヘミアセタールエステル結合からなる群より選ばれる少なくとも1つの結合を含む基である、請求項1〜5のいずれか一項に記載の製造方法。
- 前記樹脂組成物が、エチレン性不飽和結合を有する重合性化合物を含む、請求項1〜7のいずれか一項に記載の製造方法。
- 酸解離性基および下記式(2)〜(5)で示される構成単位の群から選ばれる少なくとも1つを有する重合体、並びに、酸発生剤を含む樹脂組成物。
- 請求項1〜8のいずれか一項に記載の製造方法で形成された凹パターン上に、導電膜形成用組成物を用いて導電膜を形成する工程を含む、導電膜の形成方法。
- 請求項10に記載の導電膜の形成方法で形成された導電膜を有する電子回路の製造方法。
- 請求項11に記載の電子回路の製造方法で得られた電子回路を有する電子デバイスの製造方法。
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