JP2014196284A - 感光性ガス発生剤、光硬化性組成物 - Google Patents
感光性ガス発生剤、光硬化性組成物 Download PDFInfo
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- JP2014196284A JP2014196284A JP2013272409A JP2013272409A JP2014196284A JP 2014196284 A JP2014196284 A JP 2014196284A JP 2013272409 A JP2013272409 A JP 2013272409A JP 2013272409 A JP2013272409 A JP 2013272409A JP 2014196284 A JP2014196284 A JP 2014196284A
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- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
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Abstract
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
パーフルオロアルキル基と、
前記光刺激応答性ガス発生基と、前記パーフルオロアルキル基とを連結するポリアルキレンオキシ基と、を有する化合物であることを特徴とする。
まず本発明の感光性ガス発生剤について説明する。本発明の感光性ガス発生剤は、下記(1A)乃至(1C)に示される置換基を有する化合物である。
(1A)光刺激によりガスを発生する光刺激応答性ガス発生基
(1B)パーフルオロアルキル基
(1C)光刺激応答性ガス発生基と、前記パーフルオロアルキル基とを連結するポリアルキレンオキシ基
光刺激応答性ガス発生基は、紫外線等の特定の波長の光を吸収することにより化学反応(光分解)が起こり、この化学反応(光分解)の結果として気体が発生する官能基を有する置換基である。光分解により発生する気体として、具体的には、二酸化炭素、一酸化炭素、窒素、酸素、水素等が挙げられるが、好ましくは、二酸化炭素又は窒素である。
パーフルオロアルキル基は、炭素原子及びフッ素原子を含むアルキル基であるが、フッ素原子の数を超えないことを条件として、置換基中に水素原子を一定の数含ませてもよい。ただし、パーフルオロアルキル基は、炭素原子、フッ素原子及び水素原子以外の原子は含まれない。パーフルオロアルキル基に水素原子が含まれる場合、水素原子の数は、好ましくは、フッ素原子の数の半分以下であり、より好ましくは、フッ素原子の数の3分の1以下である。この範囲にすることで、パーフルオロアルキル基が備える疎水性が有効に作用する傾向にある。
ポリアルキレンオキシ基として、具体的には、ポリエチレンオキシ基、ポリプロピレンオキシ基、ポリトリメチレンオキシ基、ポリテトラメチレンオキシ基等が挙げられる。これらは、混合でもよい。
次に、本発明の光硬化性組成物について説明する。本発明の光硬化性組成物は、少なくとも下記に示される成分(A)乃至成分(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
重合性化合物としては、例えば、ラジカル重合性化合物又はカチオン重合性化合物が挙げられる。
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。
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、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。
次に、成分(B)である光重合開始剤について説明する。光重合開始剤とは、光刺激により、重合性化合物(成分(A))の重合反応を引き起こす反応種を発生させる物質である。具体的には、光刺激によりラジカルが発生する光ラジカル発生剤、光刺激によりプロトン(H+)が発生する光酸発生剤等が挙げられる。
上記3成分に加えて界面活性剤(成分(D))を光硬化性組成物に含ませると、モールドとレジストとの間の界面結合力を低減することができるので、感光性ガス発生剤(成分(C))による離型力低減効果をさらに高めることができる。
添加剤としては、増感剤、酸化防止剤、溶剤、ポリマー成分等が含まれる。
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。作業性等の観点から、好ましくは、10℃乃至50℃である。
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、5cP乃至50cPであり、さらに好ましくは、6cP乃至20cPである。光硬化性組成物の粘度が100cPより高いと、ナノインプリントリソグラフィーに用いた場合、光硬化性組成物が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る場合がある。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する場合がある。
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、できる限りパーティクル等の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、本発明の膜の形成方法について説明する。尚、本発明でいう膜の形成方法には、光インプリント方法が含まれている。光インプリント方法とは、好ましくは、1nm乃至10mmのサイズのパターン形成方法であると定義される。より好ましくは、およそ10nm乃至100μmのサイズのパターン形成方法を意味する。一方、一般にナノサイズ(1nm乃至100nm)のパターン(凹凸構造)を有するパターン形成技術は、光ナノインプリントと呼ばれるが、本発明の膜の形成方法には光ナノインプリント法も当然に含まれる。
[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))。
(i)型接触工程で光硬化性組成物1(被形状転写層)とモールド3とが接触する前(図1(b1))は雰囲気中に気体として存在すること
(ii)光硬化性組成物1(被形状転写層)とモールド3とが接触して、モールド3上に形成された微細パターンの凹部、又はモールドと基板との間隙に塗布膜(の一部)11と一緒に雰囲気中のガスが充填されたときに、毛細管圧力で凝縮して液化すること
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。
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。
反応容器内を窒素雰囲気にした後、室温にて、反応容器内に以下に示す試薬、溶媒を投入した。
1H,1H,2H,2H−パーフルオロオクチルアルコールエチレンオキシド5モル付加物(DIC製):50部
トリエチルアミン:23.7部
ジクロロメタン:500部
次に、反応溶液を攪拌しながら、パラトルエンスルホニルクロライド21.2部をさらに加えた後、さらに18時間攪拌した。次に、懸濁液状態の反応溶液に水500mlに加えた後、有機層をクロロホルムで抽出し、乾燥した。次に、この有機層を減圧濃縮することで粗生成物を得た。次に、この粗生成物を、シリカゲルカラムクロマトグラフィーで精製することにより、反応中間体X1を、63.5部得た。
反応容器内を窒素雰囲気にした後、室温にて、反応容器内に以下に示す試薬、溶媒を投入した。
反応中間体X1:63.5部
エチルアミン:500部
反応容器内を窒素雰囲気にした後、室温にて、反応容器内に以下に示す試薬、溶媒を投入した。
2−ジアゾ−1,2−ナフトキノン−5−スルホニルクロライド:46.2部
ジクロロメタン:1L
下記に示される試薬を混合した。
(2−1)重合性化合物(A1):94重量部
(尚、重合性化合物(A1)として、下記に示される試薬及び溶媒を混合させてなる混合物を用いた。
(2−1−1)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
(2−1−2)(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
(2−1−3)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)
(2−2)光重合開始剤(B1):1重量部
(尚、光重合開始剤(B1)として、Irgacure369(チバ・ジャパン製)を用いた。)
(2−3)実施例1で合成した感光性ガス発生剤(C1):12重量部
得られた光硬化性組成物(a−1)を用いて、以下の方法で膜を作製することで光硬化性組成物(a−1)の評価を行った。また膜を作製することで、実施例1で合成した感光性ガス発生剤(C1)がもたらす離型性も評価した。
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シリコン基板(縦50mm、横25mm)上に、光硬化性組成物(a−1)を2μl滴下した。
次に、上記シリコン基板上に、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基板(縦50mm、横25mm)を、各基板の中央で交差するようにして載せて、シリコン基板と石英基板とが重なった部分(縦25mm、横25mm)に光硬化性組成物(a−1)を充填した。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、約3.2μmであった。
次に、UV光源(EX−250、HOYA CANDEO OPTRONICS CORPORATION製)を用いて、石英基板越しにUV光を光硬化性組成物(a−1)に40秒間照射して、光硬化性組成物(a−1)の硬化物からなる膜を作製した。
次に、シリコン基板と石英基板とを手で引き離した。
実施例2において、感光性ガス発生剤(C1)を、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)2重量部としたこと以外は、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。そして調製した光硬化性組成物(b−1)を用いて、実施例2と同様の方法により膜を作成し、膜作製の過程における感光性ガス発生剤の離型性を評価した。
実施例2において、感光性ガス発生剤(C1)を、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)15重量部としたこと以外は、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。そして調製した光硬化性組成物(b−2)を用いて、実施例2と同様の方法により膜を作成し、膜作製の過程における感光性ガス発生剤の離型性を評価した。
以上より、実施例1の感光性ガス発生剤を有する実施例2の光硬化性組成物は、比較例の光硬化性組成物と比較して、短い露光時間(40秒)でモールドを弱い力で引き離すことができることが判明した。即ち、本発明の感光性ガス発生剤を含む光硬化性組成物は、少ない露光量であっても離型力低減効果が優れる光硬化性組成物であることが示された。また、実施例2と比較例2との比較から、本発明の光硬化性組成物は、ガスによる離型の後でシリコン基板上に形成された膜と石英基板との界面からガスが抜けても、シリコン基板と石英基板との再付着を抑制する効果も奏することが分かる。これは、本発明の光硬化性組成物をナノインプリントリソグラフィーに用いた場合に、離型力低減という優れた効果を奏することを示している。
Claims (12)
- 光刺激によりガスを発生する光刺激応答性ガス発生基と、
パーフルオロアルキル基と、
前記光刺激応答性ガス発生基と、前記パーフルオロアルキル基とを連結するポリアルキレンオキシ基と、を有する化合物であることを特徴とする、感光性ガス発生剤。 - 前記RG1が、ジアゾナフトキノンスルホニル基であることを特徴とする、請求項2に記載の感光性ガス発生剤。
- 重合性化合物と、
光重合開始剤と、
請求項1乃至3のいずれか一項に記載の感光性ガス発生剤と、を有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の含有量が、前記重合性化合物の重量に対して1重量%以上であることを特徴とする、請求項4に記載の光硬化性組成物。
- ナノインプリントリソグラフィーで用いられることを特徴とする、請求項4又は5に記載の光硬化性組成物。
- 基板上に、請求項4乃至6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、
前記基板上に、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。 - 型接触工程が、凝縮性ガスを含む雰囲気下で行われることを特徴とする、請求項7に記載の膜の製造方法。
- 凝縮性ガスが、1,1,1,3,3−ペンタフルオロプロパンであることを特徴とする、請求項8に記載の膜の製造方法。
- 凝縮性ガスを含む雰囲気が、ヘリウムと凝縮性ガスとの混合気体であることを特徴とする、請求項8又は9に記載の膜の製造方法。
- 請求項7乃至10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い、前記パターン形状に基づいて前記基板に回路構造を形成することを特徴とする、回路付基板の製造方法。
- 基板と、前記基板の上に配置される膜と、を有し、
前記膜が、請求項7乃至10のいずれか一項に記載の膜の製造方法によって製造される膜であることを特徴とする、光学部材。
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