JP2012078505A - 感放射線性樹脂組成物 - Google Patents
感放射線性樹脂組成物 Download PDFInfo
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- JP2012078505A JP2012078505A JP2010222675A JP2010222675A JP2012078505A JP 2012078505 A JP2012078505 A JP 2012078505A JP 2010222675 A JP2010222675 A JP 2010222675A JP 2010222675 A JP2010222675 A JP 2010222675A JP 2012078505 A JP2012078505 A JP 2012078505A
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
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- 125000005843 halogen group Chemical group 0.000 description 7
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- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 3
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
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- FKJIJBSJQSMPTI-CAOXKPNISA-M sodium;(4r)-4-[(5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound [Na+].C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C FKJIJBSJQSMPTI-CAOXKPNISA-M 0.000 description 3
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- XNUYPROIFFCXAE-UHFFFAOYSA-N (4-cyclohexylphenyl)-diphenylsulfanium Chemical compound C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 XNUYPROIFFCXAE-UHFFFAOYSA-N 0.000 description 2
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Abstract
【解決手段】 (A)炭素数6〜25の脂環式炭化水素骨格を有し、該脂環式炭化水素骨格にカルボニル基を2つ以上有する化合物、および(B)酸解離性基で保護されたアルカリ不溶性またはアルカリ難溶性の樹脂であって、該酸解離性基が解離した時にアルカリ可溶性となる樹脂を含有することを特徴とする、感放射線樹脂組成物を提供する。
【選択図】 なし
Description
<化合物(A)>
本発明における化合物(A)は、炭素数6〜25の脂環式炭化水素骨格を有し、該脂環式炭化水素骨格にカルボニル基を2つ以上有する化合物である。
本発明における樹脂は、酸解離性基で保護されたアルカリ不溶性またはアルカリ難溶性の樹脂であって、該酸解離性基が解離した時にアルカリ可溶性となる樹脂である。ここでいう「アルカリ不溶性またはアルカリ難溶性」とは、本発明の感放射線性樹脂組成物から形成されたレジスト被膜からレジストパターンを形成する際に採用されるアルカリ現像条件下で、当該レジスト被膜の代わりに樹脂(B)のみを用いた被膜を現像した場合に、当該被膜の初期膜厚の50%以上が現像後に残存する性質を意味する。
本発明の感放射線性樹脂組成物を構成する酸発生剤(C)としては、スルホニウム塩やヨードニウム塩等のオニウム塩、有機ハロゲン化合物、ジスルホン類やジアゾメタンスルホン類等のスルホン化合物を挙げることができる。
本発明の感放射線性樹脂組成物には、露光により発生する酸のレジスト被膜中における拡散現象を制御し、非露光領域での好ましくない化学反応を抑制する作用を有する酸拡散制御剤を配合することが好ましい。このような酸拡散制御剤を配合することにより、感放射線性樹脂組成物の貯蔵安定性を向上させることができるとともに、解像度をさらに向上させ、また露光から現像処理までの引き置き時間(PED)の変動によるレジストパターンの線幅変化を抑えることができ、その結果、プロセス安定性に極めて優れた感放射線性樹脂組成物を得ることができる。
素複素環式化合物、酸解離性基を有する含窒素有機化合物等が好ましい。
(但し、前記一般式(D1−0)中、X+は、下記一般式(D1−1)又は(D1−2)で表されるカチオンである。Z−は、OH−、一般式(D1−3)RD1−COO−で表されるアニオン、又は、一般式(D1−4)RD1−SO3 −で表されるアニオンである(但し、前記一般式(D1−3)及び(D1−4)中、RD1は、置換されていてもよいアルキル基、脂環式炭化水素基又はアリール基である))
一般式(D1−0)中のX+は、上述したように一般式(D1−1)又は(D1−2)で表されるカチオンである。そして、一般式(D1−1)中のRD2〜RD4は、相互に独立に、水素原子、アルキル基、アルコキシル基、水酸基、又はハロゲン原子であり、これらの中でも、上記化合物の、現像液に対する溶解性を低下させる効果があるため、水素原子、アルキル基、アルコキシ基、ハロゲン原子であることが好ましい。また、一般式(D1−2)中のRD5及びRD6は、相互に独立に、水素原子、アルキル基、アルコキシル基、水酸基、又はハロゲン原子であり、これらの中でも、水素原子、アルキル基、ハロゲン原子であることが好ましい。
一般式(D1−0)中のZ−は、OH−、一般式(D1−3)RD1−COO−で表されるアニオン、又は、一般式(D1−4)RD1−SO3 −で表されるアニオンである。但し、一般式(D1−3)及び(D1−4)中のRD1は、置換されていてもよいアルキル基、脂環式炭化水素基又はアリール基であり、これらの中でも、上記化合物の、現像液に対する溶解性を低下させる効果があるため、脂環式炭化水素基又はアリール基であることが好ましい。
本発明の感放射線性樹脂組成物は、通常、溶剤を含有する。用いられる溶剤は、少なくとも化合物(A)、樹脂(B)および酸発生剤(C)、所望により添加剤(E)を溶解可能な溶剤であれば、特に限定されるものではない。
例えば、アルコール類、エーテル類、ケトン類、アミド類、エステル・ラクトン類、ニトリル類およびその混合溶媒等を使用することができる。
本発明の感放射線性樹脂組成物には、必要に応じて、フッ素含有樹脂、脂環式骨格含有化合物、界面活性剤、増感剤等の各種の添加剤(E)を配合することができる。各添加剤の配合量は、その目的に応じて適宜決定することができる。
3−〔2−ヒドロキシ−2,2−ビス(トリフルオロメチル)エチル〕テトラシクロ[4.4.0.12,5.17,10]ドデカン、2−ヒドロキシ−9−メトキシカルボニル−5−オキソ−4−オキサ−トリシクロ[4.2.1.03,7]ノナン等を挙げることができる。これらの脂環式骨格含有化合物は、1種を単独でまたは2種以上を混合して使用することができる。
本発明の感放射線性樹脂組成物は、化学増幅型レジストとして有用である。化学増幅型レジストにおいては、露光により酸発生剤から発生した酸の作用によって、樹脂成分、主に、重合体(A)中の酸解離性基が解離して、カルボキシル基を生じる。その結果、レジストの露光部のアルカリ現像液に対する溶解性が高くなり、この露光部がアルカリ現像液によって溶解、除去され、ポジ型のフォトレジストパターンが得られる。
フォトレジストパターン形成方法は、例えば、以下に示すようにしてフォトレジストパターンを形成することが一般的である。(1)感放射線性樹脂組成物を用いて、基板上にフォトレジスト膜を形成した後(工程(1))、(2)形成されたフォトレジスト膜に(必要に応じて液浸媒体を介し)、所定のパターンを有するマスクを通して放射線を照射して露光し(工程(2))、基板(露光されたフォトレジスト膜)を加熱し(工程(3))、次いで(4)現像すれば(工程(4))、フォトレジストパターンを形成することができる。
東ソー社製のGPCカラム(商品名「G2000HXL」2本、商品名「G3000HXL」1本、商品名「G4000HXL」1本)を使用し、流量:1.0mL/分、溶出溶媒:テトラヒドロフラン、カラム温度:40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフィ(GPC)により測定した。また、分散度(Mw/Mn)は、Mw及びMnの測定結果より算出した。
日本電子社製の商品名「JNM−EX400」を使用し、測定溶媒として重クロロホルムを使用して分析を行った。
(合成例1:化合物(A−1))
窒素置換した乾燥容器にデヒドロコール酸ナトリウム4.00g(9.42mmol)、ブロモ酢酸ターシャリーブチル1.83g(9.43mmol)、DMF100mlを加え室温で6時間撹拌した。反応終了後、反応液を塩化アンモニウム水溶液に注ぎ、生成物を酢酸エチルで抽出した。濃縮後再結晶にて化合物(A−1)を得た。
13C−NMR(100MHz)
212.90(1)、209.03(2)、208.67(3)、173.30(4)、166.92(5)、82.27(6)、61.02(7)、56.86(8)、51.71(9)、48.95(10)、46.79(11)、45.60(12)、45.49(13)、44.93(14)、42.74(15)、38.59(16)、36.43(17)、35.96(18)、35.37(19)、35.23(20)、31.05(21)、30.27(22)、27.98(23)、27.54(24)、25.09(25)、21.86(26)、18.58(27)、11.78(28)
窒素置換した乾燥容器にデヒドロコール酸ナトリウム4.00g(9.42mmol)、α−ブロモ―γ―ブチロラクトン1.55g(9.42mmol)、DMF100mlを加え室温で6時間撹拌した。反応終了後、合成例1と同様に精製し化合物(A−2)を得た。
13C−NMR(100MHz)
212.96(1)、209.09(2)、208.71(3)、172.90(4)、172.77(5)、67.37(6)、64.97(7)、56.84(8)、51.72(9)、48.93(10)、46.77(11)、45.55(12)、45.49(13)、44.92(14)、42.72(15)、38.57(16)、36.42(17)、35.95(18)、35.34(19)、35.26(20)、31.12(21)、30.21(22)、28.83(23)、27.60(24)、25.07(25)、21.83(26)、18.54(27)、11.77(28)
窒素置換した乾燥容器にデヒドロコール酸3.79g(9.42mmol)をメタノール100mlに溶解させ、パラトルエンスルホン酸一水和物を触媒量加え6時間加熱還流した。反応終了後、酢酸エチルで希釈し、炭酸水素ナトリウム水溶液、純水で洗浄して化合物(A−3)を得た。
13C−NMR(100MHz)
212.94(1)、209.07(2)、208.70(3)、172.88(4)、56.83(5)、51.71(6)、51.50(7)48.92(8)、46.75(9)、45.53(10)、45.46(11)、44.91(12)、42.70(13)、38.55(14)、36.40(15)、35.93(16)、35.32(17)、35.24(18)、31.10(19)、30.19(20)、27.58(21)、25.05(22)、21.81(23)、18.52(24)、11.76(25)
窒素置換した乾燥容器にリトコール酸ナトリウム4.00g(10.04mmol)、ブロモ酢酸ターシャリーブチル1.96g(10.04mmol)、DMF100mlを加え室温で6時間撹拌した。反応終了後、合成例1と同様に精製し化合物(A−4)を得た。
樹脂(B−1)は、各合成例において、下記式に示す化合物(B−1)〜(B−4)を原料モノマーとして用いて合成した。
化合物(M−1)26.42g(30mol%)、化合物(M−2)30.83g(30mol%)、化合物(M−3)19.49g(20mol%)、及び化合物(M−4)23.27g(20mol%)を200gの2−ブタノンに溶解し、AIBN4.31g(5mol%)を添加して単量体溶液を調製した。100gの2−ブタノンを入れた1000mLの三口フラスコを30分窒素パージした後、撹拌しながら80℃に加熱し、調製した単量体溶液を滴下漏斗にて3時間かけて滴下した。滴下開始を重合反応の開始時間とし、重合反応を6時間実施した。重合反応終了後、重合溶液を水冷して30℃以下に冷却した。2000gのメタノール中に冷却した重合溶液を投入し、析出した白色粉末をろ別した。ろ別した白色粉末を400gのメタノールで2回洗浄した後、ろ別し、50℃で17時間乾燥させて白色粉末状の重合体(樹脂(B−1))を得た(68g、収率68%)。得られた樹脂(B−1)のMwは6,800であり、Mw/Mnは1.54であった。また、13C−NMR分析の結果、化合物(M−1)由来の繰り返し単位:化合物(M−2)由来の繰り返し単位:化合物(M−3)由来の繰り返し単位:化合物(M−4)由来の繰り返し単位の含有比率が28.5:26.4:22.5:22.6(mol%)の共重合体であった。
(合成例5:樹脂(B−2))
化合物(M−4)38.74g(40mol%)、及び化合物(M−5)61.26g(60mol%)を200gの2−ブタノンに溶解し、AIBN3.58g(5mol%)を添加して単量体溶液を調製した。100gの2−ブタノンを入れた1000mLの三口フラスコを30分窒素パージした後、撹拌しながら80℃に加熱し、調製した単量体溶液を滴下漏斗にて3時間かけて滴下した。滴下開始を重合反応の開始時間とし、重合反応を6時間実施した。重合反応終了後、重合溶液を水冷して30℃以下に冷却した。2000gのメタノール中に冷却した重合溶液を投入し、析出した白色粉末をろ別した。ろ別した白色粉末を400gのメタノールで2回洗浄した後、ろ別し、50℃で17時間乾燥させて白色粉末状の重合体(樹脂(B−2))を得た(72g、収率72%)。得られた樹脂(B−1)のMwは6,700であり、Mw/Mnは1.54であった。また、13C−NMR分析の結果、化合物(M−4)由来の繰り返し単位:化合物(M−5)由来の繰り返し単位の含有比率が41.5:58.5(mol%)の共重合体であった。
以下、実施例及び比較例で用いた溶剤(E)を示す。
(E−2):シクロヘキサノン
(E−3):γ−ブチロラクトン
化合物(A−1)4質量部、樹脂(B−1)100質量部、酸発生剤12質量部、酸拡散制御剤1質量部および溶剤(E−1)1630質量部、(E−2)700質量部、(E−3)30質量部を混合し、得られた混合溶液を孔径0.20μmのフィルターでろ過して感放射線性樹脂組成物を調製した。この感放射線性樹脂組成物を組成物(J−1)とした。
化合物(A)と樹脂(B)とを表1に示す配合処方にしたこと以外は、実施例1と同様にして各感放射線性樹脂組成物の組成物(J−2)〜(J−10)を調製した。
得られた実施例1〜6及び比較例1〜4の感放射線性樹脂組成物について、ArFエキシマレーザーを光源として、感度、DOFについて評価を行った。
Claims (6)
- (A)炭素数6〜25の脂環式炭化水素骨格を有し、該脂環式炭化水素骨格にカルボニル基を2つ以上有する化合物、および(B)酸解離性基で保護されたアルカリ不溶性またはアルカリ難溶性の樹脂であって、該酸解離性基が解離した時にアルカリ可溶性となる樹脂を含有することを特徴とする、感放射線樹脂組成物。
- (A)化合物が、デヒドロコール酸誘導体である、請求項1に記載の感放射線樹脂組成物。
- (A)化合物が、下記式(1)で示される化合物である、請求項1乃至2に記載の感放射線樹脂組成物。
- さらに(C)感放射線性酸発生剤を含有する、請求項1乃至4に記載の感放射線性樹脂組成物。
- さらに(D)酸拡散制御剤を含有する、請求項1乃至5に記載の感放射線性樹脂組成物。
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JP2008107513A (ja) * | 2006-10-25 | 2008-05-08 | Shin Etsu Chem Co Ltd | 含窒素有機化合物、レジスト材料及びパターン形成方法 |
JP2009269953A (ja) * | 2008-05-01 | 2009-11-19 | Shin Etsu Chem Co Ltd | 新規光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP2010013627A (ja) * | 2008-06-03 | 2010-01-21 | Shin-Etsu Chemical Co Ltd | 重合性化合物、高分子化合物及びポジ型レジスト材料並びにこれを用いたパターン形成方法 |
JP2010155824A (ja) * | 2008-12-04 | 2010-07-15 | Shin-Etsu Chemical Co Ltd | スルホニウム塩、酸発生剤及びこれを用いたレジスト材料、フォトマスクブランク、並びにパターン形成方法 |
JP2011219456A (ja) * | 2009-12-10 | 2011-11-04 | Rohm & Haas Electronic Materials Llc | コラート光酸発生剤およびこれを含むフォトレジスト |
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JP2008107513A (ja) * | 2006-10-25 | 2008-05-08 | Shin Etsu Chem Co Ltd | 含窒素有機化合物、レジスト材料及びパターン形成方法 |
JP2009269953A (ja) * | 2008-05-01 | 2009-11-19 | Shin Etsu Chem Co Ltd | 新規光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP2010013627A (ja) * | 2008-06-03 | 2010-01-21 | Shin-Etsu Chemical Co Ltd | 重合性化合物、高分子化合物及びポジ型レジスト材料並びにこれを用いたパターン形成方法 |
JP2010155824A (ja) * | 2008-12-04 | 2010-07-15 | Shin-Etsu Chemical Co Ltd | スルホニウム塩、酸発生剤及びこれを用いたレジスト材料、フォトマスクブランク、並びにパターン形成方法 |
JP2011219456A (ja) * | 2009-12-10 | 2011-11-04 | Rohm & Haas Electronic Materials Llc | コラート光酸発生剤およびこれを含むフォトレジスト |
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