JP2017026980A - レジスト材料及びパターン形成方法 - Google Patents
レジスト材料及びパターン形成方法 Download PDFInfo
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- JP2017026980A JP2017026980A JP2015148563A JP2015148563A JP2017026980A JP 2017026980 A JP2017026980 A JP 2017026980A JP 2015148563 A JP2015148563 A JP 2015148563A JP 2015148563 A JP2015148563 A JP 2015148563A JP 2017026980 A JP2017026980 A JP 2017026980A
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- UQWLFOMXECTXNQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F UQWLFOMXECTXNQ-UHFFFAOYSA-N 0.000 description 1
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- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
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- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- CSYSRRCOBYEGPI-UHFFFAOYSA-N diazo(sulfonyl)methane Chemical compound [N-]=[N+]=C=S(=O)=O CSYSRRCOBYEGPI-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- MVDMNXPDKXVGGC-UHFFFAOYSA-N hexan-2-ol;hexan-3-ol Chemical compound CCCCC(C)O.CCCC(O)CC MVDMNXPDKXVGGC-UHFFFAOYSA-N 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
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- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/22—Esters containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/38—Esters containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- C—CHEMISTRY; METALLURGY
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Abstract
【解決手段】下記式(a)で表される繰り返し単位と、カルボキシル基の水素原子が酸不安定基で置換された繰り返し単位及び/又はフェノール性ヒドロキシ基の水素原子が酸不安定基で置換された繰り返し単位とを含み、重量平均分子量が1,000〜500,000の範囲であるベースポリマーを含むレジスト材料。
(式中、R1は、水素原子又はメチル基、R2及びR3は、それぞれ独立に、水素原子、又は炭素数1〜6の直鎖状、分岐状若しくは環状のアルキル基、X1は、単結合;エステル基、エーテル基若しくはラクトン環を含む炭素数1〜12の連結基;フェニレン基;又はナフチレン基、X2及びX3は、それぞれ独立に、酸素原子又は硫黄原子を表す。)
【選択図】なし
Description
1.下記式(a)で表される繰り返し単位と、カルボキシル基の水素原子が酸不安定基で置換された繰り返し単位及び/又はフェノール性ヒドロキシ基の水素原子が酸不安定基で置換された繰り返し単位とを含み、重量平均分子量が1,000〜500,000の範囲であるポリマーを含むベース樹脂を含むレジスト材料。
2.前記カルボキシル基の水素原子が酸不安定基で置換された繰り返し単位が下記式(b1)で表され、前記フェノール性ヒドロキシ基の水素原子が酸不安定基で置換された繰り返し単位が下記式(b2)で表される、1のレジスト材料。
3.前記ポリマーが、更に、ヒドロキシ基、カルボキシル基、ラクトン環、カーボネート基、チオカーボネート基、カルボニル基、環状アセタール基、エーテル基、エステル基、スルホン酸エステル基、シアノ基、アミド基、及び−O−C(=O)−G−(Gは、−S−又は−NH−である。)から選ばれる密着性基を含む繰り返し単位を含む、1又は2のレジスト材料。
4.前記ポリマーが、更に、下記式(d1)〜(d3)から選ばれる繰り返し単位を少なくとも1つ含む、1〜3のいずれかのレジスト材料。
5.更に、酸発生剤及び有機溶剤を含む1〜4のいずれかのレジスト材料。
6.更に、塩基性化合物及び/又は界面活性剤を含む5のレジスト材料。
7.1〜6のいずれかのレジスト材料を基板上に塗布する工程と、加熱処理後、高エネルギー線で露光する工程と、現像液を用いて現像する工程とを含むパターン形成方法。
8.前記高エネルギー線が、i線、KrFエキシマレーザー、ArFエキシマレーザー、電子線、又は波長3〜15nmの範囲の軟X線である7のパターン形成方法。
[ベース樹脂]
本発明のレジスト材料に含まれるベース樹脂は、下記式(a)で表される繰り返し単位(以下、繰り返し単位aという。)と、カルボキシル基の水素原子が酸不安定基で置換された繰り返し単位及び/又はフェノール性ヒドロキシ基の水素原子が酸不安定基で置換された繰り返し単位とを含むポリマー(以下、ベースポリマーという。)を含む。
本発明のレジスト材料は、化学増幅レジスト材料として機能させるために酸発生剤を含んでもよい。前記酸発生剤としては、例えば、活性光線又は放射線に感応して酸を発生する化合物(光酸発生剤)が挙げられる。
本発明のレジスト材料は、有機溶剤を含んでもよい。前記有機溶剤としては、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t−ブチル、プロピオン酸t−ブチル、プロピレングリコールモノt−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等が挙げられる。これらの溶媒は、1種単独で又は2種以上を混合して使用することができる。
本発明のレジスト材料は、更に、塩基性化合物、溶解制御剤、界面活性剤、アセチレンアルコール類等を含んでもよい。
本発明のレジスト材料、例えば、前記ベースポリマーを含むベース樹脂、酸発生剤、有機溶剤及び塩基性化合物を含む化学増幅レジスト材料を種々の集積回路製造に用いる場合は、公知のリソグラフィー技術を適用することができる。
[合成例1]モノマー1の合成
5,5−ジメチル−2,4−オキサゾリジンジオン50g及び4−(ジメチルアミノ)ピリジン3.7gをTHF500gに溶解し、氷冷下、メタクリル酸クロリド92.4gを滴下した。室温にて5時間攪拌後、水を加え反応を停止した。通常の水系後処理の後、シリカゲルカラムクロマトグラフィーにより精製を行い、モノマー1を112g得た。
2,4−チアゾリジンジオン45g及び4−(ジメチルアミノ)ピリジン3.7gをTHF500gに溶解し、氷冷下、メタクリル酸クロリド92.4gを滴下した。室温にて5時間攪拌後、水を加え反応を停止した。通常の水系後処理の後、シリカゲルカラムクロマトグラフィーにより精製を行い、モノマー2を110g得た。
ロダニン43g及び4−(ジメチルアミノ)ピリジン3.7gをTHF500gに溶解し、氷冷下、メタクリル酸クロリド92.4gを滴下した。室温にて5時間攪拌後、水を加え反応を停止した。通常の水系後処理の後、シリカゲルカラムクロマトグラフィーにより精製を行い、モノマー3を106g得た。
5,5−ジメチル−2−チオキソ−4−オキサゾリジノン57g及び4−(ジメチルアミノ)ピリジン3.7gをTHF500gに溶解し、氷冷下、メタクリル酸クロリド92.4gを滴下した。室温にて5時間攪拌後、水を加え反応を停止した。通常の水系後処理の後、シリカゲルカラムクロマトグラフィーにより精製を行い、モノマー4を114g得た。
以下の合成例において、Mwは、溶剤としてTHFを用いたゲルパーミエーションクロマトグラフィー(GPC)によるポリスチレン換算測定値である。また、以下の合成例で用いたPAGモノマー1及び2は、以下のとおりである。
2Lのフラスコに、メタクリル酸1−イソプロピルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニルを5.6g、メタクリル酸1−イソプロピルシクロペンチルを3.9g、モノマー1を5.9g、メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イルを5.9g、及び溶剤としてTHFを40g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、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1Lに加え、沈殿した白色固体を濾過後、60℃で減圧乾燥し、白色重合体(ポリマー1)を得た。
・共重合組成比(モル比)
メタクリル酸1−イソプロピルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニル:メタクリル酸1−イソプロピルシクロペンチル:モノマー1:メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イル=0.20:0.20:0.30:0.30
Mw=7,500
Mw/Mn=1.59
2Lのフラスコに、メタクリル酸1−イソプロピルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニルを5.6g、メタクリル酸1−イソプロピルシクロペンチルを3.9g、モノマー2を5.6g、メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イルを5.9g、及び溶剤としてTHFを40g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、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1Lに加え、沈殿した白色固体を濾過後、60℃で減圧乾燥し、白色重合体(ポリマー2)を得た。
・共重合組成比(モル比)
メタクリル酸1−イソプロピルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニル:メタクリル酸1−イソプロピルシクロペンチル:モノマー2:メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イル=0.20:0.20:0.30:0.30
Mw=8,900
Mw/Mn=1.69
2Lのフラスコに、メタクリル酸1−エチルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニルを5.5g、メタクリル酸1−t−ブチルシクロペンチルを4.2g、モノマー3を6.0g、メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イルを5.9g、及び溶剤としてTHFを40g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、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1Lに加え、沈殿した白色固体を濾過後、60℃で減圧乾燥し、白色重合体(ポリマー3)を得た。
・共重合組成比(モル比)
メタクリル酸1−エチルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニル:メタクリル酸1−t−ブチルシクロペンチル:モノマー3:メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イル=0.20:0.20:0.30:0.30
Mw=8,600
Mw/Mn=1.81
2Lのフラスコに、メタクリル酸1−エチルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニルを5.5g、メタクリル酸1−t−ブチルシクロペンチルを4.2g、モノマー4を6.4g、メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イルを5.9g、及び溶剤としてTHFを40g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、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1Lに加え、沈殿した白色固体を濾過後、60℃で減圧乾燥し、白色重合体(ポリマー4)を得た。
・共重合組成比(モル比)
メタクリル酸1−エチルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニル:メタクリル酸1−t−ブチルシクロペンチル:モノマー4:メタクリル酸2−オキソ−4,5−ジメチルテトラヒドロフラン−4−イル=0.20:0.20:0.30:0.30
Mw=8,900
Mw/Mn=1.71
2Lのフラスコに、メタクリル酸1−(アダマンタン−1−イル)−1−メチルエチルを5.2g、4−(1−メチルシクロペンチルオキシ)スチレンを3.1g、モノマー1を5.9g、メタクリル酸4−ヒドロキシフェニルを4.4g、PAGモノマー1を11.0g、及び溶剤としてTHFを40g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、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1Lに加え、沈殿した白色固体を濾過後、60℃で減圧乾燥し、白色重合体(ポリマー5)を得た。
・共重合組成比(モル比)
メタクリル酸1−(アダマンタン−1−イル)−1−メチルエチル:4−(1−メチルシクロペンチルオキシ)スチレン:モノマー1:メタクリル酸4−ヒドロキシフェニル:PAGモノマー1=0.20:0.15:0.30:0.20:0.15
Mw=9,100
Mw/Mn=1.73
2Lのフラスコに、メタクリル酸4−(1−メチルシクロヘキシルオキシ)フェニルを10.9g、モノマー2を4.2g、メタクリル酸4−ヒドロキシフェニルを3.6g、PAGモノマー2を15.0g、及び溶剤としてTHFを40g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、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1Lに加え、沈殿した白色固体を濾過後、60℃で減圧乾燥し、白色重合体(ポリマー6)を得た。
・共重合組成比(モル比)
メタクリル酸4−(1−メチルシクロヘキシルオキシ)フェニル:モノマー2:メタクリル酸4−ヒドロキシフェニル:PAGモノマー2=0.40:0.20:0.20:0.20
Mw=8,300
Mw/Mn=1.83
モノマー1を用いなかった以外は、合成例1と同様の方法で比較ポリマー1を合成した。
・共重合組成比(モル比)
メタクリル酸1−イソプロピルエキソテトラシクロ[4.4.0.12,5.17,10]ドデカニル:メタクリル酸1−イソプロピルシクロペンチル:メタクリル酸2−オキソ-4,5−ジメチルテトラヒドロフラン−4−イル=0.20:0.20:0.60
Mw=8,900
Mw/Mn=1.79
モノマー1のかわりにメタクリル酸2−オキソテトラヒドロフラン−3−イルを用いた以外は、合成例9と同様の方法で比較ポリマー2を合成した。
・共重合組成比(モル比)
メタクリル酸1−(アダマンタン−1−イル)−1−メチルエチル:4−(1−メチルシクロペンチルオキシ)スチレン:メタクリル酸2−オキソテトラヒドロフラン−3−イル:メタクリル酸4−ヒドロキシフェニル:PAGモノマー1=0.20:0.15:0.30:0.20:0.15
Mw=9,100
Mw/Mn=1.78
[実施例1−1〜1−5、比較例1−1]
[3−1]レジスト材料の調製
住友スリーエム(株)製界面活性剤FC-4430を100ppm溶解させた溶剤に、表1に示す組成で各成分を溶解させた溶液を、0.2μmサイズのフィルターで濾過してポジ型レジスト材料(R−1〜R−5)を調製した。
表1中の各組成は以下のとおりである。
有機溶剤: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)
GBL(γ−ブチロラクトン)
酸発生剤:PAG1
クエンチャー:Quencher1
撥水性ポリマー1:Mw=12,100、Mw/Mn=1.78
調製したレジスト材料(R−1〜R−5)を、シリコンウエハーに信越化学工業(株)製スピンオンカーボン膜ODL-101(カーボンの含有量が80質量%)を160nm、その上にケイ素含有スピンオンハードマスクSHB-A940(ケイ素の含有量が43質量%)を35nmの膜厚で成膜したトライレイヤープロセス用の基板上にスピンコーティングし、ホットプレートを用いて80℃で60秒間ベークし、厚さ80nmのレジスト膜を作製した。
これをArFエキシマレーザー液浸スキャナー((株)ニコン製、NSR-610C、NA1.30、σ0.98/0.78、クロスポール開口20度、Azimuthally偏光照明、6%ハーフトーン位相シフトマスク、ウエハー上寸法がピッチ90nm、ライン幅30nmの格子状マスク)を用いて露光量を変化させながら露光を行い、露光後、表2に示した温度で60秒間PEBをし、現像ノズルから酢酸ブチルを3秒間30rpmで回転させながら吐出させ、その後静止パドル現像を27秒間行い、スピンドライしてネガ型のパターンを得た。
[実施例2−1〜2−2、比較例2−1]
[4−1]レジスト材料の調製
住友スリーエム(株)製界面活性剤FC-4430を100ppm溶解させた溶剤に、表3に示す組成で各成分を溶解させた溶液を、0.2μmサイズのフィルターで濾過してポジ型レジスト材料(R−6〜R−8)を調製した。
表3中の各組成は以下のとおりである。
有機溶剤: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)
PGME(プロピレングリコールモノメチルエーテル)
CyH(シクロヘキサノン)
塩基性化合物:Amine1
調製したポジ型レジスト材料(R−6〜R−8)を直径6インチφのヘキサメチルジシラザン(HMDS)ベーパープライム処理したSi基板上に、クリーントラックMark 5(東京エレクトロン(株)製)を用いてスピンコートし、ホットプレート上で110℃で60秒間プリベークして、厚さ100nmのレジスト膜を作製した。これに、(株)日立製作所製HL-800Dを用いてHV電圧50kVで真空チャンバー内描画を行った。
描画後、直ちにクリーントラックMark 5を用いてホットプレート上で表4に記載の温度で60秒間PEBを行い、2.38質量%のTMAH水溶液で30秒間パドル現像を行い、ポジ型のパターンを得た。
100nmのラインアンドスペースを1:1で解像する露光量における、最小の寸法を解像力とし、100nmLSのエッジラフネス(LWR)をSEMで測定した。結果を表4に示す。
Claims (8)
- 下記式(a)で表される繰り返し単位と、カルボキシル基の水素原子が酸不安定基で置換された繰り返し単位及び/又はフェノール性ヒドロキシ基の水素原子が酸不安定基で置換された繰り返し単位とを含み、重量平均分子量が1,000〜500,000の範囲であるポリマーを含むベース樹脂を含むレジスト材料。
- 前記カルボキシル基の水素原子が酸不安定基で置換された繰り返し単位が下記式(b1)で表され、前記フェノール性ヒドロキシ基の水素原子が酸不安定基で置換された繰り返し単位が下記式(b2)で表される、請求項1記載のレジスト材料。
- 前記ポリマーが、更に、ヒドロキシ基、カルボキシル基、ラクトン環、カーボネート基、チオカーボネート基、カルボニル基、環状アセタール基、エーテル基、エステル基、スルホン酸エステル基、シアノ基、アミド基、及び−O−C(=O)−G−(Gは、−S−又は−NH−である。)から選ばれる密着性基を含む繰り返し単位を含む、請求項1又は2記載のレジスト材料。
- 前記ポリマーが、更に、下記式(d1)〜(d3)から選ばれる繰り返し単位を少なくとも1つ含む、請求項1〜3のいずれか1項記載のレジスト材料。
- 更に、酸発生剤及び有機溶剤を含む請求項1〜4のいずれか1項記載のレジスト材料。
- 更に、塩基性化合物及び/又は界面活性剤を含む請求項5記載のレジスト材料。
- 請求項1〜6のいずれか1項記載のレジスト材料を基板上に塗布する工程と、加熱処理後、高エネルギー線で露光する工程と、現像液を用いて現像する工程とを含むパターン形成方法。
- 前記高エネルギー線が、i線、KrFエキシマレーザー、ArFエキシマレーザー、電子線、又は波長3〜15nmの範囲の軟X線である請求項7記載のパターン形成方法。
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JP2020023685A (ja) * | 2018-08-02 | 2020-02-13 | 住友化学株式会社 | 樹脂、レジスト組成物及びレジストパターンの製造方法 |
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TWI603147B (zh) | 2017-10-21 |
US20170031243A1 (en) | 2017-02-02 |
TW201710784A (zh) | 2017-03-16 |
KR20170013818A (ko) | 2017-02-07 |
KR101933762B1 (ko) | 2018-12-28 |
JP6520524B2 (ja) | 2019-05-29 |
US9720324B2 (en) | 2017-08-01 |
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