JP2020196872A - レジスト組成物、その製造方法及びそれを含む物品 - Google Patents
レジスト組成物、その製造方法及びそれを含む物品 Download PDFInfo
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- 0 *C(C1CC=CCC1)=C Chemical compound *C(C1CC=CCC1)=C 0.000 description 3
- IBGDXBPGGZQSCX-UHFFFAOYSA-N CC1(CCCCC1)OC(COC(C(C)=C)=O)=O Chemical compound CC1(CCCCC1)OC(COC(C(C)=C)=O)=O IBGDXBPGGZQSCX-UHFFFAOYSA-N 0.000 description 1
- SPRQNDQKKMPDJV-UHFFFAOYSA-N CC1(CCCCC1)OC(COC(C=C)=O)=O Chemical compound CC1(CCCCC1)OC(COC(C=C)=O)=O SPRQNDQKKMPDJV-UHFFFAOYSA-N 0.000 description 1
- KHZBKVHVOLBHFJ-UHFFFAOYSA-N CCC1(CCCC1)OC(COC(C(C)=C)=O)=O Chemical compound CCC1(CCCC1)OC(COC(C(C)=C)=O)=O KHZBKVHVOLBHFJ-UHFFFAOYSA-N 0.000 description 1
- JFZUPQMZLSTWTH-UHFFFAOYSA-N CCC1(CCCC1)OC(COC(C=C)=O)=O Chemical compound CCC1(CCCC1)OC(COC(C=C)=O)=O JFZUPQMZLSTWTH-UHFFFAOYSA-N 0.000 description 1
- LHSQMFZZSYXFFI-UHFFFAOYSA-N CCC1(CCCC1)OC(OCCOC(C(C)=C)=O)=O Chemical compound CCC1(CCCC1)OC(OCCOC(C(C)=C)=O)=O LHSQMFZZSYXFFI-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本開示では、「化学線」又は「放射線」は、例えば、水銀ランプの輝線スペクトル、エキシマレーザーに代表される遠紫外線、極紫外線(EUV)、X線、電子ビーム及びイオンビームなどの粒子線などを意味する。更に、本発明において「光」とは、化学線又は放射線を意味する。
R1とR2は、任意選択で一緒に環を形成し、
Yは、カルボニル、スルホニル、或いは置換又は非置換メチレンから選択され、
Y及びR2は、任意選択で一緒に置換又は非置換4〜7員単環式環或いは置換又は非置換9〜12員二環式環(縮合及びスピロを含む)を形成し、単環式及び二環式環は、N、O、及びSから選択される1、2、又は3つのヘテロ原子を任意選択で含み、それぞれの環は、飽和、不飽和、又は芳香族であり、それぞれの環は、任意選択でエーテル基、カルボニル基、エステル基、カーボネート基、アミン基、アミド基、尿素基、スルフェート基、スルホン基、スルホキシド基、N−オキシド基、スルホネート基、スルホンアミド基、又はこれらの組み合わせを含み、環における置換基は、ハロゲン、ヒドロキシル、シアノ、ニトロ、C1〜C12アルキル基、C1〜C12ハロアルキル基、C1〜C12アルコキシ基、C3〜C12シクロアルキル基、アミノ、C2〜C6アルカノイル、カルボキサミド、置換又は非置換C6〜C14アリール基、或いはC3〜C12ヘテロアリール基であり、R4及びR5は、それぞれ独立して、水素、ハロゲン、置換又は非置換C1〜C3アルキル基であり、置換基はハロゲンであり、n=1、2又は3である)の構造の重合から誘導される。
式(13c)において、Xは、S又はIであり、それぞれのRcは、ハロゲン化されていても非ハロゲン化されていてもよく、
独立してC1〜30アルキル基、多環式又は単環式C3〜30シクロアルキル基、多環式又は単環式C4〜30アリール基であり、XがSの場合、Rc基の1つは、単結合により隣接する1つのRc基に任意選択で結合し、zは2又は3であり、XがIである場合、zは2である、又はXがSである場合、zは3である)を有する。
Ar1及びAr2は、独立して、C10〜30の縮合した又は単結合した多環アリール基であり、
Rlは、XがIである場合、孤立電子対であるか、又はXがSである場合、C6〜20アリール基であり、
pは、2又は3の整数であり、ここで、XがIである場合、pは、2であり、XがSである場合、pは、3であり、
q及びrは、それぞれ独立して、0〜5の整数であり、及び
s及びtは、それぞれ独立して、0〜4の整数である)
を有し得る。
この例は、レジスト組成物で使用される環式イミド繰り返し単位の合成を示すために行われた。
この例は、レジストポリマー(レジストコポリマー)の製造を実証し、レジストポリマーと、ラクタムモノマー及び/又はイミドモノマーを含まないレジストポリマーの溶解性を比較するために実行された。モノマー供給溶液は、22.8gの乳酸エチル、9.8gのγ−ブチロラクトン(GBL)、9.56gの化合物−4、8.92gの化合物−6、及び3.65gの化合物−3を用いて調製した。様々な化合物の参照番号を以下に示す。別に、開始剤供給溶液を、8.3gの乳酸エチル、3.5gのγ−ブチロラクトン、及び1.16gのV−601を用いて調製した。反応器で、9.4gの70/30乳酸エチル/GBLを80℃まで温め、次いでモノマー供給溶液を0.20mL/分で240分間滴下し、開始剤供給溶液を0.084mL/分、90分で滴下した。4時間後、反応混合物を1℃/分で室温まで冷却し、1L(リットル)のイソプロピルアルコールに直接加えることによりポリマーを沈殿させた。ポリマーを濾過によって収集し、真空中で乾燥させて、16.3gの白色固体を得た。分子量は、ポリスチレン標準と比較してGPCによって決定し、数平均分子量(Mn)=4510Da、重量平均分子量(Mw)=8050ダルトン、PDI(多分散性指数)=1.8であることがわかった。
この実施例は、レジスト組成物のレジスト特性を決定するために行った。配合R1〜R2(レジスト組成物)及びCR1〜CR2(比較のレジスト組成物)を、表3に示される成分及び量で調製した。表3において、括弧内の数字は、それぞれの成分の重量比を示す。C1、F1、P1、S1、及びS2で表される構造を表3で下に示す。
Claims (10)
- 第1の繰り返し単位と第2の繰り返し単位とを含むポリマーであって、前記第1の繰り返し単位は、酸不安定基を含み、前記第2の繰り返し単位は、式(1)
R1とR2は、任意選択で一緒に環を形成し、
Yは、カルボニル、スルホニル、或いは置換又は非置換メチレンから選択され、
Y及びR2は、任意選択で一緒に置換又は非置換4〜7員単環式環或いは置換又は非置換9〜12員二環式環を形成し、前記単環式及び二環式環は、N、O、及びSから選択される1、2、又は3のヘテロ原子を任意選択で含み、それぞれの環は、飽和、不飽和、又は芳香族であり、それぞれの環は、エーテル基、カルボニル基、エステル基、カーボネート基、アミン基、アミド基、尿素基、スルフェート基、スルホン基、スルホキシド基、N−オキシド基、スルホネート基、スルホンアミド基、又はこれらの組み合わせを任意選択で含み、前記環における前記置換基は、ハロゲン、ヒドロキシル、シアノ、ニトロ、C1〜C12アルキル基、C1〜C12ハロアルキル基、C1〜C12アルコキシ基、C3〜C12シクロアルキル基、アミノ、C2〜C6アルカノイル、カルボキサミド、置換又は非置換C6〜C14アリール基、或いはC3〜C12ヘテロアリール基であり、R4及びR5は、それぞれ独立して、水素、ハロゲン、置換又は非置換C1〜C3アルキル基であり、前記置換基はハロゲンであり、n=1〜3である)の構造の重合から誘導される、ポリマー。 - 前記第1の繰り返し単位は、(メタ)アクリレートモノマー又はビニル芳香族モノマーである、請求項1又は2に記載のポリマー。
- 前記第1の繰り返し単位は、3級アルキルエステルを含む、請求項1〜3のいずれか一項に記載のポリマー。
- 前記第1の繰り返し単位は、アセタール基又はケタール基を含む、請求項1〜4のいずれか一項に記載のポリマー。
- ラクトン基、スルトン基、及び/又は光酸発生剤基の1つを含む第3の繰り返し単位を更に含む、請求項1〜7のいずれか一項に記載のポリマー。
- 溶媒と、
光酸発生剤と、請求項1〜8のいずれか一項に記載のポリマーとを含むフォトレジスト組成物。 - 請求項9に記載のフォトレジスト組成物の層を基板に渡り塗布する工程と、
前記フォトレジスト組成物層を活性化放射線にパターン状に露光する工程と、
前記露光されたフォトレジスト組成物層を現像してレジストレリーフ画像を提供する工程と、を含む、パターン形成方法。
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