JP2020037544A - スルホニウム化合物、ポジ型レジスト組成物、及びレジストパターン形成方法 - Google Patents
スルホニウム化合物、ポジ型レジスト組成物、及びレジストパターン形成方法 Download PDFInfo
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- 125000005843 halogen group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 49
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Images
Classifications
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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Abstract
Description
1.下記式(A)で表されるスルホニウム化合物。
2.(A)1のスルホニウム化合物を含むクエンチャーを含むポジ型レジスト組成物。
3.更に、(B)酸の作用により分解し、アルカリ現像液中での溶解度が増大するポリマーを含むベースポリマーを含む2のポジ型レジスト組成物。
4.前記ポリマーが、下記式(B1)〜(B3)で表される繰り返し単位から選ばれる少なくとも1種を含む3のポジ型レジスト組成物。
5.前記ポリマーが、更に、下記式(B4)で表される繰り返し単位を含むものである3又は4のいずれかのポジ型レジスト組成物。
6.前記ポリマーが、更に、下記式(B5)〜(B7)で表される繰り返し単位から選ばれる少なくとも1種を含むものである3〜5のいずれかのポジ型レジスト組成物。
7.前記ポリマーが、更に、下記式(B8)〜(B11)で表される繰り返し単位から選ばれる少なくとも1種を含む2〜6のいずれかのポジ型レジスト組成物。
8.更に、(C)下記式(C1)で表される繰り返し単位と、下記式(C2)〜(C5)で表される繰り返し単位から選ばれる少なくとも1種とを含むポリマーを含む2〜7のいずれかのポジ型レジスト組成物。
9.更に、(D)有機溶剤を含む2〜8のいずれかのポジ型レジスト組成物。
10.更に、(E)光酸発生剤を含む2〜9のいずれかのポジ型レジスト組成物。
11.基板上に、2〜10のいずれかのポジ型レジスト組成物を用いてレジスト膜を形成する工程、高エネルギー線を用いて前記レジスト膜にパターンを照射する工程、及びアルカリ現像液を用いて前記レジスト膜を現像する工程を含むレジストパターン形成方法。
12.前記高エネルギー線が、EUV又はEBである11のレジストパターン形成方法。
13.前記基板の最表面が、ケイ素を含む材料からなる11又は12のレジストパターン形成方法。
14.前記基板が、フォトマスクブランクである11〜13のいずれかのレジストパターン形成方法。
15.2〜10のいずれかのポジ型レジスト組成物を塗布したフォトマスクブランク。
本発明のポジ型レジスト組成物に含まれるベースポリマーは、下記式(B1)で表される繰り返し単位(以下、繰り返し単位B1ともいう。)、下記式(B2)で表される繰り返し単位(以下、繰り返し単位B2ともいう。)、下記式(B3)で表される繰り返し単位(以下、繰り返し単位B3ともいう。)から選ばれる少なくとも1種を含むポリマーを含むものである。
本発明のポジ型レジスト組成物は、高コントラスト化、高エネルギー線照射における酸のケミカルフレア及び帯電防止膜材料をレジスト上に塗布するプロセスにおける帯電防止膜からの酸のミキシングを遮蔽し、予期しない不要なパターン劣化を抑制する目的で、(C)成分として、下記式(C1)で表される繰り返し単位(以下、繰り返し単位C1ともいう。)、並びに下記式(C2)、(C3)、(C4)及び(C5)で表される繰り返し単位(以下、それぞれ繰り返し単位C2、C3、C4及びC5ともいう。)から選ばれる少なくとも1種を含むフッ素含有ポリマーを含んでもよい。前記フッ素含有ポリマーは、界面活性機能も有することから、現像プロセス中に生じ得る不溶物の基板への再付着を防止できるため、現像欠陥に対する効果も発揮する。
本発明のポジ型レジスト組成物は、(D)成分として有機溶剤を含んでもよい。前記有機溶剤としては、各成分を溶解可能なものであれば特に限定されない。このような有機溶剤としては、例えば、特開2008−111103号公報の段落[0144]〜[0145]に記載の、シクロヘキサノン、メチル−2−n−ペンチルケトン等のケトン類;3−メトキシブタノール、3−メチル−3−メトキシブタノール、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール、ジアセトンアルコール等のアルコール類;プロピ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、エチ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ジメチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル類;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、乳酸エチル、ピルビン酸エチル、酢酸ブチル、3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、酢酸tert−ブチル、プロピオン酸tert−ブチル、プロピレングリコールモノtert−ブチルエーテルアセテート等のエステル類;γ−ブチロラクトン等のラクトン類;及びこれらの混合溶剤が挙げられる。アセタール系の酸不安定基を用いる場合は、アセタールの脱保護反応を加速させるために高沸点のアルコール系溶剤、具体的にはジエチレングリコール、プロピレングリコール、グリセリン、1,4−ブタンジオール、1,3−ブタンジオール等を加えることもできる。
本発明のレジスト組成物は、化学増幅ポジ型レジスト組成物として機能させるために、(E)光酸発生剤を含んでもよい。光酸発生剤としては、高エネルギー線照射により酸を発生する化合物であれば、特に限定されない。好適な光酸発生剤としては、スルホニウム塩、ヨードニウム塩、スルホニルジアゾメタン、N−スルホニルオキシイミド、オキシム−O−スルホネート型酸発生剤等がある。これらは、1種単独で又は2種以上を組み合わせて用いることができる。
本発明のレジスト組成物は、パターンの形状補正等を目的に、(A)成分以外のクエンチャーとして(F)塩基性化合物を含んでもよい。塩基性化合物を添加することにより、酸拡散を効果的に制御することができ、かつ、被加工基板として、最表面がクロムを含む材料からなる基板を用いた場合でも、レジスト膜内に発生する酸によるクロムを含む材料への影響を抑えることができる。
本発明のレジスト組成物には、被加工基板への塗布性を向上させるために慣用されている界面活性剤を添加してもよい。界面活性剤を用いる場合、特開2004−115630号公報にも多数の例が記載されているように多数のものが公知であり、それらを参考にして選択することができる。(G)界面活性剤の含有量は、(B)ベースポリマー100質量部に対し、0〜5質量部が好ましい。
本発明のレジストパターン形成方法は、基板上に、前述したレジスト組成物を用いてレジスト膜を形成する工程、高エネルギー線を用いて前記レジスト膜にパターンを照射する工程、及びアルカリ現像液を用いて前記レジスト膜を現像する工程を含む。
・IR:サーモフィッシャーサイエンティフィック社製、NICOLET 6700
・1H-NMR:日本電子(株)製、ECA-500
・LC-MS:Waters社製、ACQUITY UPLC H-Classシステム及びACQUITY QDa
[実施例1−1]N−2−(ジフェニルスルホニオ)フェニルメシルアミダート(Q−1)の合成
[実施例1−1−1]N−2−フェニルチオフェニルメシルアミド(中間体A)の合成
IR (D-ATR): ν= 3110, 1750, 1531, 1365, 1333, 1298, 1285, 987, 950, 900, 720, 688, 522 cm-1。
LC-MS: POSITIVE [M+H]+356(C19H18NO2S2 +相当)
IR (D-ATR): ν= 2885, 1780, 1543, 1432, 1390, 1357, 1128, 1009, 987, 841, 821, 776, 678 cm-1。
LC-MS: POSITIVE [M+H]+432(C25H21NO2S2 +相当)
[実施例1−3−1]N−2−フェニルチオフェニル−2−フルオロベンゼンスルホニルアミド(中間体E)の合成
IR (D-ATR): ν= 3050, 1876, 1565, 1552, 1433, 1380, 1145, 1009, 987, 840, 769, 712, 489 cm-1。
LC-MS: POSITIVE [M+H]+435(C24H18FNO2S2 +相当)
[合成例1−1]ポリマーA1の合成
3Lのフラスコに、アセトキシスチレン407.5g、アセナフチレン42.5g及び溶剤としてトルエンを1,275g添加した。この反応容器を、窒素雰囲気下、−70℃まで冷却し、減圧脱気、窒素フローを3回繰り返した。室温まで昇温後、重合開始剤として2,2'−アゾビス(2,4−ジメチルバレロニトリル)(和光純薬工業(株)製V-65)を34.7g加え、55℃まで昇温し、40時間反応させた。この反応溶液に、攪拌しながらメタノール970g及び水180gの混合溶剤を滴下した。滴下終了後、30分間静置し、2層に分離させた。下層(ポリマー層)を減圧濃縮し、このポリマー層をメタノール0.45L及びTHF0.54Lの混合溶剤に再度溶解し、そこへトリエチルアミン160g及び水30gを加え、60℃に加熱して40時間脱保護反応を行った。この脱保護反応溶液を減圧濃縮し、濃縮液にメタノール548g及びアセトン112gを加えて溶液化した。そこへ攪拌しながらヘキサンを990g滴下した。滴下終了後、30分間静置し、2層に分離させた。下層(ポリマー層)にTHF300gを加え、そこへ攪拌しながらヘキサンを1,030g滴下し、30分後に下層(ポリマー層)を減圧濃縮した。得られたポリマー溶液を酢酸82gを用いて中和し、該溶液を濃縮後、アセトン0.3Lに溶解し、更に水10Lに添加して沈殿させ、濾過、乾燥を行い、白色重合体280gを得た。得られた重合体を1H−NMR及びGPCで測定したところ、共重合組成比が、ヒドロキシスチレン:アセナフチレン=89.3:10.7、Mwが5,000、及びMw/Mnが1.63のポリマーであった。
得られたポリマー100gに、(2−メチル−1−プロペニル)メチルエーテル50gを酸性条件下反応させて、中和、分液処理、晶出工程を経て、ポリマーA1を得た。収量は125gであった。
使用する原料化合物を変えた以外は、合成例1−1と同様の方法でポリマーA2〜A7及びポリマーP1〜P2を合成した。
[実施例2−1〜2−38、比較例1−1〜1−6]
クエンチャーとしてスルホニウム化合物Q−1〜Q−3又は比較例用のクエンチャーQ−4〜Q−6、ベースポリマーとしてポリマーA1〜A7、ポリマーP1〜P2、光酸発生剤PAG−A〜PAG−C、及び添加剤としてフッ素含有ポリマー(ポリマーC1〜C3)を表1〜3に示す組成で有機溶剤に溶解し、得られた各溶液0.02μmサイズのUPEフィルターで濾過することにより、ポジ型レジスト組成物を調製した。表1〜3中、有機溶剤は、PGMEA(プロピレングリコールモノメチルエーテルアセテート)、EL(乳酸エチル)、PGME(プロピレングリコールモノメチルエーテル)及びCyH(シクロヘキサノン)である。また、各組成物には、界面活性剤としてPF-636(OMNOVA SOLUTIONS社製)を固形分100質量部に対し、0.075質量部添加した。
[実施例3−1〜3−38、比較例2−1〜2−6]
ポジ型レジスト組成物R−1〜R−38及びCR−1〜CR−6を、それぞれACT−M(東京エレクトロン(株)製)を用いてヘキサメチルジシラザン(HMDS)ベーパープライム処理した152mm角の最表面が酸化ケイ素であるマスクブランク上にスピンコーティングし、ホットプレート上で、110℃で600秒間プリベークして膜厚80nmのレジスト膜を作製した。得られたレジスト膜の膜厚測定は、光学式測定器ナノスペック(ナノメトリックス社製)を用いて行った。測定は、ブランク外周から10mm内側までの外縁部分を除くブランク基板の面内81箇所で行い、膜厚平均値と膜厚範囲を算出した。
[実施例4−1〜4−8、比較例3−1〜3−2]
ポジ型レジスト組成物R−1、R−3、R−6、R−31、R−32、R−36〜R−38及びCR−1〜CR−2を、それぞれMark8(東京エレクトロン(株)製)を用いてHMDSベーパープライム処理した6インチシリコンウエハー上へスピンコーティングし、110℃、240秒間の熱処理を施して、膜厚80nmのレジスト膜を作製した。更に、導電性高分子組成物を滴下し、Mark8(東京エレクトロン(株)製)でレジスト膜上全体に回転塗布した。ホットプレート上で、90℃で90秒間ベークを行い、膜厚60nmの帯電防止膜を作製した。なお、導電性高分子組成物としては、Proc. of SPIE Vol. 8522 85220O-1に記載の、ポリスチレンでドープされたポリアニリンの水分散液を調製して用いた。続いて、電子線露光装置((株)日立ハイテクノロジーズ製HL-800D、加速電圧50kV)を用いて露光し、その後、15秒間の純水リンス工程にて帯電防止膜を剥離し、110℃で240秒間PEBを施し、2.38質量%TMAH水溶液で80秒現像を行い、ポジ型のパターンを得た。
1.下記式(A)で表されるスルホニウム化合物。
2.(A)1のスルホニウム化合物を含むクエンチャーを含むポジ型レジスト組成物。
3.更に、(B)酸の作用により分解し、アルカリ現像液中での溶解度が増大するポリマーを含むベースポリマーを含む2のポジ型レジスト組成物。
4.前記ポリマーが、下記式(B1)〜(B3)で表される繰り返し単位から選ばれる少なくとも1種を含む3のポジ型レジスト組成物。
5.前記ポリマーが、更に、下記式(B4)で表される繰り返し単位を含むものである3又は4のいずれかのポジ型レジスト組成物。
6.前記ポリマーが、更に、下記式(B5)〜(B7)で表される繰り返し単位から選ばれる少なくとも1種を含むものである3〜5のいずれかのポジ型レジスト組成物。
7.前記ポリマーが、更に、下記式(B8)〜(B11)で表される繰り返し単位から選ばれる少なくとも1種を含む3〜6のいずれかのポジ型レジスト組成物。
8.更に、(C)下記式(C1)で表される繰り返し単位と、下記式(C2)〜(C5)で表される繰り返し単位から選ばれる少なくとも1種とを含むポリマーを含む2〜7のいずれかのポジ型レジスト組成物。
9.更に、(D)有機溶剤を含む2〜8のいずれかのポジ型レジスト組成物。
10.更に、(E)光酸発生剤を含む2〜9のいずれかのポジ型レジスト組成物。
11.基板上に、2〜10のいずれかのポジ型レジスト組成物を用いてレジスト膜を形成する工程、高エネルギー線を用いて前記レジスト膜にパターンを照射する工程、及びアルカリ現像液を用いて前記レジスト膜を現像する工程を含むレジストパターン形成方法。
12.前記高エネルギー線が、EUV又はEBである11のレジストパターン形成方法。
13.前記基板の最表面が、ケイ素を含む材料からなる11又は12のレジストパターン形成方法。
14.前記基板が、フォトマスクブランクである11〜13のいずれかのレジストパターン形成方法。
15.2〜10のいずれかのポジ型レジスト組成物を塗布したフォトマスクブランク。
Claims (15)
- (A)請求項1記載のスルホニウム化合物を含むクエンチャーを含むポジ型レジスト組成物。
- 更に、(B)酸の作用により分解し、アルカリ現像液中での溶解度が増大するポリマーを含むベースポリマーを含む請求項2記載のポジ型レジスト組成物。
- 前記ポリマーが、下記式(B1)〜(B3)で表される繰り返し単位から選ばれる少なくとも1種を含む請求項3記載のポジ型レジスト組成物。
- 前記ポリマーが、更に、下記式(B4)で表される繰り返し単位を含むものである請求項3又は4のいずれか1項記載のポジ型レジスト組成物。
- 前記ポリマーが、更に、下記式(B5)〜(B7)で表される繰り返し単位から選ばれる少なくとも1種を含むものである請求項3〜5のいずれか1項記載のポジ型レジスト組成物。
- 前記ポリマーが、更に、下記式(B8)〜(B11)で表される繰り返し単位から選ばれる少なくとも1種を含む請求項2〜6のいずれか1項記載のポジ型レジスト組成物。
- 更に、(C)下記式(C1)で表される繰り返し単位と、下記式(C2)〜(C5)で表される繰り返し単位から選ばれる少なくとも1種とを含むポリマーを含む請求項2〜7のいずれか1項記載のポジ型レジスト組成物。
- 更に、(D)有機溶剤を含む請求項2〜8のいずれか1項記載のポジ型レジスト組成物。
- 更に、(E)光酸発生剤を含む請求項2〜9のいずれか1項記載のポジ型レジスト組成物。
- 基板上に、請求項2〜10のいずれか1項記載のポジ型レジスト組成物を用いてレジスト膜を形成する工程、高エネルギー線を用いて前記レジスト膜にパターンを照射する工程、及びアルカリ現像液を用いて前記レジスト膜を現像する工程を含むレジストパターン形成方法。
- 前記高エネルギー線が、極端紫外線又は電子線である請求項11記載のレジストパターン形成方法。
- 前記基板の最表面が、ケイ素を含む材料からなる請求項11又は12記載のレジストパターン形成方法。
- 前記基板が、フォトマスクブランクである請求項11〜13のいずれか1項記載のレジストパターン形成方法。
- 請求項2〜10のいずれか1項記載のポジ型レジスト組成物を塗布したフォトマスクブランク。
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