JP7471724B2 - 光硬化型組成物、その硬化物を含むコーティング層および半導体工程用基材 - Google Patents
光硬化型組成物、その硬化物を含むコーティング層および半導体工程用基材 Download PDFInfo
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- JP7471724B2 JP7471724B2 JP2022551727A JP2022551727A JP7471724B2 JP 7471724 B2 JP7471724 B2 JP 7471724B2 JP 2022551727 A JP2022551727 A JP 2022551727A JP 2022551727 A JP2022551727 A JP 2022551727A JP 7471724 B2 JP7471724 B2 JP 7471724B2
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- acrylate
- urethane
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Description
本発明は、光硬化型組成物、その硬化物を含むコーティング層および半導体工程用基材に関する。
さらに、本発明の一実施態様は、基材フィルムと、前記コーティング層と、を含む半導体工程用基材を提供する。
本願明細書全体において、ある部材が他の部材の「上に」位置しているとする時、これは、ある部材が他の部材に接している場合のみならず、2つの部材の間にさらに他の部材が存在する場合も含む。
本願明細書全体において、単位「重量部」は、各成分間の重量の比率を意味する。
本願明細書全体において、「第1」および「第2」のように序数を含む用語は、1つの構成要素を他の構成要素から区別する目的で使われ、前記序数によって限定されない。例えば、発明の権利範囲内において、第1構成要素は第2構成要素と名付けられてもよく、同様に、第2構成要素は第1構成要素と名付けられてもよい。
本発明の一実施態様は、イソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマーと反応性基含有(メタ)アクリレート系化合物との反応生成物であるウレタン(メタ)アクリレート系樹脂および(メタ)アクリレート系単量体混合物を含むウレタン(メタ)アクリレート系樹脂シロップ;多官能ウレタン(メタ)アクリレート系化合物;および多官能(メタ)アクリレート系化合物;を含み、前記ウレタン(メタ)アクリレート系樹脂は、炭素数1~3の側鎖が少なくとも1つ結合した炭素数1~10のアルキレンを含有するカーボネート繰り返し単位を含む光硬化型組成物を提供する。
本発明の一実施態様によれば、20℃における前記ウレタン(メタ)アクリレート系樹脂シロップの粘度は、550cP以上3,250cP以下、600cP以上3,200cP以下、700cP以上3,150cP以下、750cP以上3,100cP以下、500cP以上2,500cP以下、550cP以上2,300cP以下、600cP以上2,100cP以下、650cP以上2,000cP以下、700cP以上1,900cP以下、750cP以上1,850cP以下、1,000cP以上3,300cP以下、1,200cP以上3,250cP以下、1,500cP以上3,200cP以下、1,700cP以上3,150cP以下、または1,800cP以上3,100cP以下であってもよい。
本発明の一実施態様に係るコーティング層は、低いTTVを有することにより、表面品質に優れる。前述のように、前記光硬化型組成物は、ウェッティング性およびコーティング性に優れ、前記光硬化型組成物のコーティング膜は、表面品質と厚さ均一性に優れる。そのため、前記光硬化型組成物のコーティング膜を硬化させて形成した前記コーティング層も、表面品質と厚さ均一性に優れる。また、前記コーティング層は、応力緩和性能および機械的物性に優れる。
図1aを参照すれば、本発明の一実施態様に係る半導体工程用基材100は、基材フィルム10と、前記基材フィルム10の一面上に備えられるコーティング層20とを含むことができる。この時、前記コーティング層は、前述した光硬化型組成物の硬化物を含む。
以下、本発明を具体的に説明するために、実施例を挙げて詳細に説明する。
製造例1
5口の2L反応器に、メチル基が側鎖に結合したペンチレンを含有するカーボネート繰り返し単位を含むポリアルキレンカーボネート系ポリオールとしてNippollan963(Tosoh社)、ジイソシアネート系化合物としてイソホロンジイソシアネート(IPDI;Evonik社)とヘキサメチレンジイソシアネート(50M-HDI、旭化成社)、イソボルニルアクリレート(IBOA、Solay社)を投入し、混合して第1混合物を製造した。この時、Nippollan963を100重量部基準として、IPDIの含有量は約13.8重量部、50M-HDIの含有量は約2.0重量部であった。
前記製造例1において、Nippollan963を100重量部基準として、IPDIの含有量は約12.9重量部、50M-HDIの含有量は約1.4重量部に調節したことを除き、前記製造例1と同様の方法でイソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマーを製造した。
前記製造例1において、Nippollan963を100重量部基準として、IPDIの含有量は約12.0重量部、50M-HDIの含有量は約0.9重量部に調節したことを除き、前記製造例1と同様の方法でイソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマーを製造した。
前記製造例2において、ポリアルキレンカーボネート系ポリオールとしてNippollan963の代わりにT5652(旭化成社)を用いたことを除き、前記製造例2と同様の方法でイソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマー、ウレタン(メタ)アクリレート系樹脂、およびウレタン(メタ)アクリレート系樹脂シロップを製造した。
この時、T5652は、側鎖がないアルキレンを含有するカーボネート繰り返し単位を含むポリアルキレンカーボネート系ポリオールに相当する。
前記製造例3において、ポリアルキレンカーボネート系ポリオールとしてNippollan963の代わりにT5652(旭化成社)を用いたことを除き、前記製造例3と同様の方法でイソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマー、ウレタン(メタ)アクリレート系樹脂、およびウレタン(メタ)アクリレート系樹脂シロップを製造した。
前記製造例2において、ポリアルキレンカーボネート系ポリオールとしてNippollan963の代わりにG3452(旭化成社)を用いたことを除き、前記製造例2と同様の方法でイソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマー、ウレタン(メタ)アクリレート系樹脂、およびウレタン(メタ)アクリレート系樹脂シロップを製造した。
この時、G3452は、側鎖がないアルキレンを含有するカーボネート繰り返し単位を含むポリアルキレンカーボネート系ポリオールに相当する。
前記製造例2において、ポリアルキレンカーボネート系ポリオールとしてNippollan963の代わりにT4672(旭化成社)を用いたことを除き、前記製造例2と同様の方法でイソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマー、ウレタン(メタ)アクリレート系樹脂、およびウレタン(メタ)アクリレート系樹脂シロップを製造した。
この時、T4672は、側鎖がないアルキレンを含有するカーボネート繰り返し単位を含むポリアルキレンカーボネート系ポリオールに相当する。
実施例1
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップに、重量平均分子量が3,500g/molの前記化学式1-1(R7~R9は水素)で表される3官能ウレタン(メタ)アクリレート系化合物(GD301、LG化学)、多官能(メタ)アクリレート系化合物として1,6-ヘキサンジオールジアクリレート(HDDA;M200、ミウォンスペシャルティ社)、光開始剤としてIrgacure#651(BASF社)を混合して、光硬化型組成物を製造した。
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップの代わりに製造例2で製造されたウレタン(メタ)アクリレート系樹脂シロップを用いたことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップの代わりに製造例3で製造されたウレタン(メタ)アクリレート系樹脂シロップを用いたことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップの代わりに製造例4で製造されたウレタン(メタ)アクリレート系樹脂シロップを用いたことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップの代わりに製造例5で製造されたウレタン(メタ)アクリレート系樹脂シロップを用いたことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップの代わりに製造例6で製造されたウレタン(メタ)アクリレート系樹脂シロップを用いたことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例1で製造されたウレタン(メタ)アクリレート系樹脂シロップの代わりに製造例7で製造されたウレタン(メタ)アクリレート系樹脂シロップを用いたことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例2で製造されたウレタン(メタ)アクリレート系樹脂シロップを用い、ウレタン(メタ)アクリレート系樹脂シロップに含まれたウレタン(メタ)アクリレート系樹脂100重量部を基準として3官能ウレタン(メタ)アクリレート系化合物の含有量を1.0重量部に調節したことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例2で製造されたウレタン(メタ)アクリレート系樹脂シロップを用い、ウレタン(メタ)アクリレート系樹脂シロップに含まれたウレタン(メタ)アクリレート系樹脂100重量部を基準として3官能ウレタン(メタ)アクリレート系化合物の含有量を9.0重量部に調節したことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例2で製造されたウレタン(メタ)アクリレート系樹脂シロップを用い、ウレタン(メタ)アクリレート系樹脂シロップに含まれたウレタン(メタ)アクリレート系樹脂100重量部を基準として多官能(メタ)アクリレート系化合物であるHDDAの含有量を0.5重量部に調節したことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
製造例2で製造されたウレタン(メタ)アクリレート系樹脂シロップを用い、ウレタン(メタ)アクリレート系樹脂シロップに含まれたウレタン(メタ)アクリレート系樹脂100重量部を基準として多官能(メタ)アクリレート系化合物であるHDDAの含有量を8.0重量部に調節したことを除き、前記実施例1と同様の方法でコーティング層およびコーティング層を含む半導体工程用基材を製造した。
粘度の測定
実施例1~実施例3および比較例1~比較例8の光硬化型組成物の粘度(25℃)を測定し、測定された粘度値を下記表2に示した。
実施例1~実施例3および比較例1~比較例8の光硬化型組成物のコーティング性評価を下記のように進行させた。
Ο(良好):ポンプにかかる力が1kgf以下
△(可能):ポンプにかかる力が1kgf超過3kgf以下
X(不可):ポンプにかかる力が3kgf超過
総厚さ偏差(TTV、Total Thickness Variation)の測定
実施例1~実施例3および比較例1~比較例8で製造された半導体工程用基材の応力緩和性評価を下記のように進行させた。
応力緩和性は、バックグラインディング過程で発生する力によってウエハに衝撃が加えられて割れる現象または反り(warpage)を防止する程度を意味するものであって、実施例1~実施例3および比較例1~比較例8で製造された半導体工程用基材それぞれを15mm×100mm×0.05mm(幅×幅×厚さ)の大きさに試験片を製造した。以後、測定装置(Stable Micro Systems社、texture analyzer)を用いて評価し、40%引張させる時、初期に測定される力(A)と1分後測定される力(B)の変化率を下記式1により導出した。その結果を下記表2および表3に示した。
[式1]
応力緩和率(%)=(A-B)/A×100
引張強度の測定
実施例1~実施例3および比較例1~比較例8で製造された半導体工程用基材の引張強度を下記のように測定した。
10:基材フィルム
20:コーティング層
30:ハードコート層
Claims (17)
- イソシアネート末端基を有するポリアルキレンカーボネート系ウレタンプレポリマーと反応性基含有(メタ)アクリレート系化合物との反応生成物であるウレタン(メタ)アクリレート系樹脂および(メタ)アクリレート系単量体混合物を含むウレタン(メタ)アクリレート系樹脂シロップ;
多官能ウレタン(メタ)アクリレート系化合物;および
多官能(メタ)アクリレート系化合物;を含み、
前記ウレタン(メタ)アクリレート系樹脂は、
炭素数1~3の側鎖が少なくとも1つ結合した炭素数1~10のアルキレンを含有するカーボネート繰り返し単位を含む光硬化型組成物。 - 前記ウレタン(メタ)アクリレート系樹脂の重量平均分子量は、20,000g/mol以上50,000g/mol以下である、請求項1に記載の光硬化型組成物。
- 前記ウレタン(メタ)アクリレート系樹脂シロップの25℃における粘度は、0.4Pa・s以上3.3Pa・s以下である、請求項1に記載の光硬化型組成物。
- 前記ポリアルキレンカーボネート系ウレタンプレポリマーは、
ポリアルキレンカーボネート系ポリオールおよびジイソシアネート系化合物の反応生成物である、請求項1に記載の光硬化型組成物。 - 前記ジイソシアネート系化合物の含有量は、前記ポリアルキレンカーボネート系ポリオール100重量部に対して、10重量部以上20重量部以下である、請求項4に記載の光硬化型組成物。
- 前記反応性基含有(メタ)アクリレート系化合物の含有量は、前記ポリアルキレンカーボネート系ウレタンプレポリマー100重量部に対して、1重量部以上10重量部以下である、請求項1に記載の光硬化型組成物。
- 前記ウレタン(メタ)アクリレート系樹脂の含有量は、前記ウレタン(メタ)アクリレート系樹脂シロップ100重量部に対して、15重量部以上35重量部以下である、請求項1に記載の光硬化型組成物。
- 前記(メタ)アクリレート系単量体混合物は、アルキル基含有(メタ)アクリレート系単量体、脂環族アルキル基含有(メタ)アクリレート系単量体、芳香族基含有(メタ)アクリレート系単量体、および極性官能基含有(メタ)アクリレート系単量体から選択される少なくとも1つのタイプのモノマーを含むものである、請求項1に記載の光硬化型組成物。
- 前記(メタ)アクリレート系単量体混合物の含有量は、前記ウレタン(メタ)アクリレート系樹脂シロップ100重量部に対して、65重量部以上85重量部以下である、請求項1に記載の光硬化型組成物。
- 前記多官能ウレタン(メタ)アクリレート系化合物は、下記化学式1で表される化合物を含むものである、請求項1に記載の光硬化型組成物:
R1、R2およびR3は、それぞれ独立して、炭素数2~10のアルキレンであり、
R4、R5およびR6は、それぞれ独立して、炭素数2~7のアルキレンであり、
R7、R8およびR9は、それぞれ独立して、水素、またはメチル基であり、
n、j、およびkは、それぞれ独立して、1~3の整数である。 - 前記多官能ウレタン(メタ)アクリレート系化合物の含有量は、前記ウレタン(メタ)アクリレート系樹脂100重量部に対して、2.5重量部以上7.5重量部以下である、請求項1に記載の光硬化型組成物。
- 前記多官能(メタ)アクリレート系化合物の含有量は、前記ウレタン(メタ)アクリレート系樹脂100重量部に対して、1重量部以上5重量部以下である、請求項1に記載の光硬化型組成物。
- 光開始剤をさらに含み、
前記光開始剤の含有量は、前記ウレタン(メタ)アクリレート系樹脂100重量部に対して、0.5重量部以上3重量部以下である、請求項1に記載の光硬化型組成物。 - 前記光硬化型組成物の25℃における粘度は、3.0Pa・s以下である、請求項1に記載の光硬化型組成物。
- 請求項1に記載の光硬化型組成物の硬化物を含むコーティング層。
- 最大厚さと最小厚さとの差で定義される総厚さ偏差が3μm以下である、請求項15に記載のコーティング層。
- 基材フィルムと、
請求項15に記載のコーティング層と、を含む半導体工程用基材。
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