JP2014096575A - 光硬化性組成物及び膜の製造方法 - Google Patents
光硬化性組成物及び膜の製造方法 Download PDFInfo
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- JP2014096575A JP2014096575A JP2013199376A JP2013199376A JP2014096575A JP 2014096575 A JP2014096575 A JP 2014096575A JP 2013199376 A JP2013199376 A JP 2013199376A JP 2013199376 A JP2013199376 A JP 2013199376A JP 2014096575 A JP2014096575 A JP 2014096575A
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- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
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Abstract
【解決手段】表面に凹凸を有するモールドと接触させた状態で光を用いて硬化することにより、凹凸を有する膜を製造するための光硬化性組成物であって、重合性化合物と、光重合開始剤と、光刺激応答部位を有する感光性ガス発生剤と、を有し、前記感光性ガス発生剤が、少なくとも1以上のアルキレンオキサイド鎖の繰り返し構造を有し、かつ光照射により前記光刺激応答部位からガスが発生することを特徴とする、光硬化性組成物。
【選択図】なし
Description
(a)レジスト(光硬化性組成物)を配置する配置工程
(b)光硬化性組成物と表面に微細凹凸パターンが形成された型(モールド)とを接触させる型接触工程
(c)光硬化性組成物に光を照射する光照射工程
(d)光照射工程の後、光硬化性組成物とモールドとを引き離す離型工程
重合性化合物と、
光重合開始剤と、
光刺激応答部位を有する感光性ガス発生剤と、を有し、
前記感光性ガス発生剤が、少なくとも1以上のアルキレンオキサイド鎖の繰り返し構造を有し、かつ光照射により前記光刺激応答部位からガスが発生することを特徴とする。
本発明の光硬化性組成物は、表面に凹凸を有するモールドと接触させた状態で光を用いて硬化することにより、凹凸を有する膜を製造するための光硬化性組成物である。そして、本発明の光硬化性組成物は、少なくとも下記成分(A)から成分(C)を有している。(A)重合性化合物
(B)光重合開始剤
(C)感光性ガス発生剤
本発明の光硬化性組成物を構成する重合性化合物としては、ラジカル重合性化合物又はカチオン重合性化合物が例として挙げられる。
アクリロイル基又はメタクリロイル基を1つ有する単官能(メタ)アクリル化合物としては、例えば、フェノキシエチル(メタ)アクリレート、フェノキシ−2−メチルエチル(メタ)アクリレート、フェノキシエトキシエチル(メタ)アクリレート、3−フェノキシ−2−ヒドロキシプロピル(メタ)アクリレート、2ーフェニルフェノキシエチル(メタ)アクリレート、4−フェニルフェノキシエチル(メタ)アクリレート、3−(2−フェニルフェニル)−2−ヒドロキシプロピル(メタ)アクリレート、EO変性p−クミルフェノールの(メタ)アクリレート、2−ブロモフェノキシエチル(メタ)アクリレート、2,4−ジブロモフェノキシエチル(メタ)アクリレート、2,4,6−トリブロモフェノキシエチル(メタ)アクリレート、EO変性フェノキシ(メタ)アクリレート、PO変性フェノキシ(メタ)アクリレート、ポリオキシエチレンノニルフェニルエーテル(メタ)アクリレート、イソボルニル(メタ)アクリレート、1−アダマンチル(メタ)アクリレート、2−メチル−2−アダマンチル(メタ)アクリレート、2−エチル−2−アダマンチル(メタ)アクリレート、ボルニル(メタ)アクリレート、トリシクロデカニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、4−ブチルシクロヘキシル(メタ)アクリレート、アクリロイルモルホリン、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、メチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、ブチル(メタ)アクリレート、アミル(メタ)アクリレート、イソブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、ペンチル(メタ)アクリレート、イソアミル(メタ)アクリレート、へキシル(メタ)アクリレート、ヘプチル(メタ)アクリレート、オクチル(メタ)アクリレート、イソオクチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ノニル(メタ)アクリレート、デシル(メタ)アクリレート、イソデシル(メタ)アクリレート、ウンデシル(メタ)アクリレート、ドデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、イソステアリル(メタ)アクリレート、ベンジル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、エトキシジエチレングリコール(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、ポリプロピレングリコールモノ(メタ)アクリレート、メトキシエチレングリコール(メタ)アクリレート、エトキシエチル(メタ)アクリレート、メトキシポリエチレングリコール(メタ)アクリレート、メトキシポリプロピレングリコール(メタ)アクリレート、ジアセトン(メタ)アクリルアミド、イソブトキシメチル(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、t−オクチル(メタ)アクリルアミド、ジメチルアミノエチル(メタ)アクリレート、ジエチルアミノエチル(メタ)アクリレート、7−アミノ−3,7−ジメチルオクチル(メタ)アクリレート、N,N−ジエチル(メタ)アクリルアミド、N,N−ジメチルアミノプロピル(メタ)アクリルアミド等が挙げられるが、これらに限定されない。
ビニルエーテル基を1つ有する化合物としては、例えば、メチルビニルエーテル、エチルビニルエーテル、プロピルビニルエーテル、n−ブチルビニルエーテル、t−ブチルビニルエーテル、2−エチルヘキシルビニルエーテル、n−ノニルビニルエーテル、ラウリルビニルエーテル、シクロヘキシルビニルエーテル、シクロヘキシルメチルビニルエーテル、4−メチルシクロヘキシルメチルビニルエーテル、ベンジルビニルエーテル、ジシクロペンテニルビニルエーテル、2−ジシクロペンテノキシエチルビニルエーテル、メトキシエチルビニルエーテル、エトキシエチルビニルエーテル、ブトキシエチルビニルエーテル、メトキシエトキシエチルビニルエーテル、エトキシエトキシエチルビニルエーテル、メトキシポリエチレングリコールビニルエーテル、テトラヒドロフリフリルビニルエーテル、2−ヒドロキシエチルビニルエーテル、2−ヒドロキシプロピルビニルエーテル、4−ヒドロキシブチルビニルエーテル、4−ヒドロキシメチルシクロヘキシルメチルビニルエーテル、ジエチレングリコールモノビニルエーテル、ポリエチレングリコールビニルエーテル、クロルエチルビニルエーテル、クロルブチルビニルエーテル、クロルエトキシエチルビニルエーテル、フェニルエチルビニルエーテル、フェノキシポリエチレングリコールビニルエーテル等が挙げられるが、これらに限定されない。
本発明において、光重合開始剤(成分(B))は、所定の波長の光を感知して上記重合因子(ラジカル、カチオン等)を発生させるための化合物である。具体的には、光重合開始剤(成分(B))は、成分(A)である重合性化合物がラジカル重合性化合物の場合では、光(赤外線、可視光線、紫外線、遠紫外線、X線、電子線等の荷電粒子線等、放射線)によりラジカルを発生する重合開始剤である。一方、成分(A)である重合性化合物がカチオン重合性化合物の場合では、光により酸を発生する重合開始剤である。
感光性ガス発生剤とは、紫外線等の光を受けることにより化学反応(脱離反応)を起こしこの化学反応の際に気体が発生する物質をいう。感光性ガス発生剤としては、例えば、アゾ系化合物、アゾビス系化合物、ジアゾニウム塩系化合物、アジド系化合物、ジアゾナフトキノン系化合物、スルホヒドラジド系化合物、ヒドラゾ系化合物、ニトロベンジルカルバメート系化合物、ベンゾインカルバメート系化合物、ジアゾメタンスルホン酸系化合物等がある。
RG1−XA−(O−RA−)nYA (1)
RG1−XA−(O−RA−)n−XB−RG1’ (2)
YA(−RA−O)n−XA−RG2−XB−(O−RB−)mYB (3)
本発明の光硬化性組成物は、上述した成分(A)乃至(C)に加えて、さらにフッ素系界面活性剤(成分(D))を含ませるのが好ましい。
Rf1−Rc−X (6)
また本発明の光硬化性組成物は、上述した成分(A)乃至成分(C)(あるいは成分(A)乃至成分(D))の他にさらに添加成分を含有していてもよい。即ち、本発明の光硬化性組成物は、重合性化合物(成分(A))、重合開始剤(成分(B))、感光性ガス発生剤(成分(C))の他に、種々の目的に応じ、本発明の効果を損なわない範囲で、増感剤、酸化防止剤、溶剤、ポリマー成分等の添加成分を含ませてもよい。
試薬、溶媒を混合・溶解させることによって光硬化性組成物を調製する際には所定の温度条件下で行う。具体的には、0℃乃至100℃の範囲で行う。
本発明の光硬化性組成物の粘度は、溶剤を除く成分の混合物について23℃での粘度が、好ましくは、1cP乃至100cPであり、より好ましくは、3cP乃至50cPであり、さらに好ましくは、3cP乃至20cPである。光硬化性組成物の粘度が100cPより高いと、光硬化性組成物をモールドに接触する際にモールド上の微細パターンのうち凹部に組成物が充填するのに長い時間が必要となったり、充填不良によるパターン欠陥が生じたりすることがある。一方、粘度が1cPより低いと、光硬化性組成物を塗布する際に塗りムラを生じたり、光硬化性組成物をモールドに接触する際に、モールドの端部から光硬化性組成物が流出したりする恐れがある。
本発明の光硬化性組成物の表面張力は、溶剤を除く成分の混合物について23℃での表面張力が、好ましくは、5mN/m乃至70mN/mであり、より好ましくは、7mN/m乃至35mN/mであり、さらに好ましくは、10mN/m乃至32mN/mである。ここで表面張力が5mN/mより低いと、光硬化性組成物をモールドに接触する際にモールド上の微細パターンのうち凹部に組成物が充填するのに長い時間が必要となる。一方、表面張力が70mN/mより高いと、表面平滑性が低くなる。
本発明の光硬化性組成物は、できる限り不純物を取り除くのが望ましい。例えば、光硬化性組成物に混入したパーティクルによって光硬化物に不用意に凹凸が生じてパターンの欠陥が発生するのを防止するためにパーティクル等の不純物を取り除くのが望ましい。具体的には、光硬化性組成物に含まれる各成分を混合した後、例えば、孔径0.001μm乃至5.0μmのフィルタで濾過することが好ましい。フィルタを用いた濾過を行う際には、多段階で行ったり、多数回繰り返したりすることがさらに好ましい。また、濾過した液を再度濾過してもよい。濾過に使用するフィルタとしては、ポリエチレン樹脂製、ポリプロピレン樹脂製、フッ素樹脂製、ナイロン樹脂製等のフィルタを使用することができるが、特に限定されるものではない。
次に、本発明の膜の製造方法について説明する。図3は、本発明の膜の製造方法における実施形態の例を示す断面模式図である。図3に示される製造プロセスは、下記[1]乃至[5]あるいは[6]に示される工程からなる製造プロセスである。
[1]配置工程(塗布工程、図1(a))
[2]型接触工程(図1(b1)、(b2))
[3]光照射工程(図1(c))
[4]離型工程(図1(d))
[5]残膜除去工程(図1(e))
[6]基板加工工程(図1(f))
まず光硬化性組成物1を基板2上に配置(塗布)して塗布膜を形成する(図1(a))。ここでいう光硬化性組成物とは、本発明の光硬化性組成物である。
次に、前工程(配置工程)で形成された光硬化性組成物1からなる塗布膜にモールドを接触させる工程(型接触工程、図1(b1)、図1(b2))を行う。尚、モールド3は印章と見立てることができるので、この工程は、押印工程とも呼ばれる。本工程で、光硬化性組成物1(被形状転写層)にモールド3を接触させる(図1(b1))と、モールド3上に形成された微細パターンの凹部に塗布膜(の一部)11が充填される(図1(b2))。
室温で蒸気圧が0.1MPa乃至0.4MPaのガスであれば、光硬化性組成物1が基板2とモールド3との間隙やモールド3上の凹部に侵入する際に発生する毛細管圧力で容易に凝縮し、液化されて気泡が消滅する。
フロン類の中でも、特に、1,1,1,3,3−ペンタフルオロプロパン(CHF2CH2CF3、HFC−245fa、PFP)が好ましい。尚、PFPは、室温付近である23℃での蒸気圧が0.14MPaで、沸点が15℃である。
次に、モールド3を介して塗布膜11に光を照射する(図1(c))。この工程において、塗布膜11は、照射される光によって硬化して光硬化物12を形成する。本工程において、本発明の光硬化性組成物は、まず成分(A)である重合性化合物が硬化し、引き続いて、成分(C)である感光性ガス発生剤からガスが発生する。これらの反応を順番よく行うようにするためには、光硬化性組成物1に含まれる成分(A)である重合性化合物の重合反応速度を、成分(C)である感光性ガス発生剤のガス発生反応速度よりも速くするように反応条件と適宜制御することが好ましい。重合反応速度がガス発生反応速度より速ければ、重合性化合物が硬化した後にモールドと光硬化性組成物との界面で集中的にガスが凝集し、結果として、離型力低減効果を得ることができる。しかし、逆に、ガス発生反応速度が重合反応速度よりの速い場合は、硬化膜12内で発泡が生じたり、離型力の低減効果が得られなかったりする問題が生じる。
次に、光硬化物12からモールド3を離し、基板2上に所定のパターン形状を有する硬化膜を形成する工程(離型工程、図1(d))を行う。この工程(離型工程)は、光硬化物12からモールド3を剥離する工程であり、前の工程(光照射工程)において、モールド3上に形成された微細パターンの反転パターンが、光硬化物12のパターンとして得られる。
上記離型工程を行ったときに得られる硬化膜は、特定のパターン形状を有するものの、このパターン形状が形成される領域以外の領域においても膜の一部が残膜として存在することがある。そこで上記パターン形状のうち、光硬化物を除去すべき領域について残存する光硬化膜(残膜)を除去する工程(残膜除去工程、図1(e))を行う。
本発明の製造方法によって得られる所望の凹凸パターン形状を有する光硬化物12は、例えば、LSI、システムLSI、DRAM、SDRAM、RDRAM、D−RDRAM等の半導体素子に代表される電子部品に含まれる層間絶縁膜用膜として利用可能である。一方、この光硬化物12は、半導体素子製造時におけるレジスト膜として利用することもできる。
非特許文献2に開示されている合成方法を用いて、下記式に示されるヘキサ(エチレンオキサイド)モノメチルエーテル 12−(2−ジアゾ−1,2−ナフトキノン−5−スルホニルアミノ)ドデカノエイト(NIT−29)を合成した。収率は86%だった。
(1)光硬化性組成物
まず下記に示される成分(A)、成分(B)、成分(C)及び成分(D)を配合することで混合溶液を得た。
<A−1>イソボルニルアクリレート(共栄社化学製、商品名:IB−XA):61.6重量部
<A−2>(2−メチル−2−エチル−1,3−ジオキソラン−4−イル)メチルアクリレート(大阪有機化学工業製、商品名:MEDOL−10):10重量部
<A−3>ヘキサンジオールジアクリレート(大阪有機化学工業製、商品名:ビスコート#230):22.4重量部
(1−2)成分(B):1重量部
Irgacure369(チバ・ジャパン製)
(1−3)成分(C):10重量部
NIT−29:10重量部
(1−4)成分(D):1.1重量部
ペンタデカエチレングリコールモノ1H,1H,2H,2H−パーフルオロオクチルエーテル(F(CF2)6CH2CH2(OCH2CH2)15OH、DIC製)1.1重量部
マイクロピペットを用いて、密着層として厚さ60nmの密着促進層が形成された34インチシリコンウエハ上に、光硬化性組成物(a−1)を16μl滴下した。
次に、上記シリコンウエハ上に、表面処理がされておらず、パターンも形成されていない石英モールド(縦40mm、横40mm)を接触させた。このとき形成される光硬化性組成物(a−1)の液膜の膜厚は、厚さ約10μmであった。
次に、石英モールドを、0.5mm/sの条件で引き上げて光硬化物からモールドを離した。
次に、得られた光硬化物について以下に説明する測定を行い、その物性を評価した。
ロードセル(引張圧縮両用型小型ロードセルLUR−A−200NSA1(共和電業製))を用いて、離型工程において、光硬化物からモールドを離したときに要した力を測定した。測定の結果、離型力は大きくても20N以下(ノイズレベル)であり、後述する比較例2にて光硬化性組成物(b−2)から作製した光硬化物よりも低い値であった。また本実施例では、光照射工程の際にマスク前面において生じた干渉縞が後述する比較例2より短い時間で観察された。これにより、本発明の膜の製造方法は、光照射工程の時間を短縮できるので生産性が高いことが示された。
実施例1において、成分(C)を、NIT−29の代わりに下記式に示されるNIT−40を用いたこと以外は、実施例1と同様の方法により光硬化性組成物(a−2)を調製した。尚、本実施例では、NIT−40を9.28重量部用いた。
実施例1において、成分(C)を、NIT−29の代わりに下記式に示されるNIT−42を用いたこと以外は、実施例1と同様の方法により光硬化性組成物(a−3)を調製した。尚、本実施例では、NIT−42を6.44重量部用いた。
実施例1において、成分(C)を、NIT−29の代わりに2−ジアゾ−1,2−ナフトキノン−5−スルホン酸p−クレゾールエステル(PC−5、東洋合成製)を用いたこと以外は、実施例1と同様の方法により光硬化性組成物(b−1)を調製した。尚、本比較例では、PC−5を2重量部用いた。
実施例1において、成分(C)を、NIT−29の代わりに2,2’−アゾビス−(N−ブチル−2−メチルプロピオンアミド)(VAm−110、和光純薬製)を用いたこと以外は、実施例1と同様の方法により光硬化性組成物(b−2)を調製した。尚、本比較例では、VAm−110を15重量部用いた。
比較例2において、実施例1と同様の方法によりUV光を光硬化性組成物に240秒間照射した。その結果、実施例1のような干渉縞は観察されなかった。本比較例において、光照射開始後240秒後に、実施例1と同様の方法により離型力の測定を行ったところ、離型力は111Nであった。
実施例1において、成分(D)を添加しなかったこと以外は、実施例1と同様の方法により光硬化性組成物(b−4)を調製した。
Claims (17)
- 表面に凹凸を有するモールドと接触させた状態で光を用いて硬化することにより、凹凸を有する膜を製造するための光硬化性組成物であって、
重合性化合物と、
光重合開始剤と、
光刺激応答部位を有する感光性ガス発生剤と、を有し、
前記感光性ガス発生剤が、少なくとも1以上のアルキレンオキサイド鎖の繰り返し構造を有し、かつ光照射により前記光刺激応答部位からガスが発生することを特徴とする、光硬化性組成物。 - 前記感光性ガス発生剤が、下記一般式(1)に示される化合物であることを特徴とする、請求項1に記載の光硬化性組成物。
RG1−XA−(O−RA−)nYA (1)
(式(1)において、RG1は、光刺激応答部位となる一価の置換基を表す。XAは、二価の連結基を表す。RAは、二価のアルキレン基を表す。nは、1以上の整数を表す。YAは一価の官能基を表す。) - 前記感光性ガス発生剤が、下記一般式(2)に示される化合物であることを特徴とする、請求項1に記載の光硬化性組成物。
RG1−XA−(O−RA−)n−XB−RG1’ (2)
(式(2)において、RG1及びRG1’は、光刺激応答部位となる一価の官能基である。RG1及びRG1’は、同じであってもよいし異なっていてもよい。XA及びXBは、それぞれ二価の連結基である。XA及びXBは、互いに同じであっても異なっていてもよい。RAは二価のアルキレン基である。nは1以上の整数である。) - 前記感光性ガス発生剤が、下記一般式(3)に示される化合物であることを特徴とする、請求項1に記載の光硬化性組成物。
YA(−RA−O)n−XA−RG2−XB−(O−RB−)mYB (3)
(式(3)において、RG2は、光刺激応答部位となる二価の官能基を表す。RA及びRBは、それぞれ二価のアルキレン基を表す。RA及びRBは、同じであってもよいし異なっていてもよい。m及びnは1以上の整数を表す。XA及びXBは、それぞれ二価の連結基を表す。XA及びXBは、互いに同じであっても異なっていてもよい。YA及びYBは、それぞれ一価の置換基を表す。YA及びYBは、同じであってもよいし異なっていてもよい。 - 前記アルキレンオキサイド鎖がエチレンオキサイド鎖であることを特徴とする、請求項1に記載の光硬化性組成物。
- 前記光刺激応答部位が、2−ジアゾ−1,2−ナフトキノン基であることを特徴とする、請求項1乃至3及び5のいずれか一項に記載の光硬化性組成物。
- さらにフッ素系界面活性剤が含まれることを特徴とする、請求項1乃至8のいずれか一項に記載の光硬化性組成物。
- 前記感光性ガス発生剤の配合割合が、前記重合性化合物の全量に対して10重量%以上であり、
前記フッ素系界面活性剤の配合割合が、前記重合性化合物の全量に対して0.005重量%乃至3重量%であることを特徴とする、請求項8に記載の光硬化性組成物。 - 被加工基材の上に、請求項1乃至10のいずれか一項に記載の光硬化性組成物を配置する配置工程と、
前記光硬化性組成物とモールドとを接触させる型接触工程と、
前記光硬化性組成物に光を照射する光照射工程と、
前記光照射工程の後、前記光硬化性組成物と前記モールドとを引き離す離型工程と、
を有し、
前記被加工基材の上に、所定のパターン形状を有する膜を得ることを特徴とする、膜の製造方法。 - 前記膜の厚さが10μm以下であることを特徴とする、請求項11に記載の膜の製造方法。
- 前記光硬化性組成物と接する前記モールドの表面が石英であることを特徴とする、請求項11又は12に記載のパターン形成方法。
- 前記型接触工程が、凝縮性ガスを含むガス雰囲気中で行われることを特徴とする、請求項11に記載の膜の製造方法。
- 前記光照射工程が、前記モールドを介して前記光硬化性組成物に光を照射する工程であることを特徴とする、請求項11乃至14のいずれか一項に記載のパターン形成方法。
- 請求項11乃至15のいずれか一項に記載の膜の製造方法により得られた膜のパターン形状に基づいてエッチング又はイオン注入を行う工程と、
前記膜のパターン形状に基づいて被加工基板に回路構造を形成する工程と、を有することを特徴とする、回路付基板の製造方法。 - 基材と、
前記基材の上に配置され所定のパターン形状を有する膜と、を有し、
前記膜が、請求項1乃至10のいずれか一項に記載の光硬化性組成物を硬化させてなる膜であることを特徴とする、光学部品。
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