JP7044011B2 - 重合性単量体、重合体、レジスト材料、及びパターン形成方法 - Google Patents
重合性単量体、重合体、レジスト材料、及びパターン形成方法 Download PDFInfo
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- JP7044011B2 JP7044011B2 JP2018152840A JP2018152840A JP7044011B2 JP 7044011 B2 JP7044011 B2 JP 7044011B2 JP 2018152840 A JP2018152840 A JP 2018152840A JP 2018152840 A JP2018152840 A JP 2018152840A JP 7044011 B2 JP7044011 B2 JP 7044011B2
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- 229940017219 methyl propionate Drugs 0.000 description 1
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- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
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- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
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- 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
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
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- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- ARXCQFYCNIBVIN-UHFFFAOYSA-N styrene hydroiodide Chemical compound I.C=CC1=CC=CC=C1 ARXCQFYCNIBVIN-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 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-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 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
Classifications
-
- 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
-
- 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
- C08F12/00—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 aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/373—Halogenated derivatives with all hydroxy groups on non-condensed rings and with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/247—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
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Description
1.下記式(A)で表される重合性単量体。
X1は、単結合、エーテル結合、エステル結合又はアミド結合である。
Raは、炭素数1~20の1価炭化水素基であり、Raが2つ以上存在する場合、隣接する2つのRaが、互いに結合してこれらが結合する炭素原子と共に脂環構造を形成してもよい。また、前記1価炭化水素基を構成するメチレン基が、エーテル結合又はカルボニル基で置換されていてもよい。
Rbは、水素原子又は酸不安定基である。
Xは、ハロゲン原子である。
n及びmは、1≦n≦4、0≦m≦3及び1≦n+m≦4を満たす整数である。)
2.X1が、単結合である1の重合性単量体。
3.Xが、ヨウ素原子である1又は2の重合性単量体。
4.側鎖に下記式(B)で表される部分構造を有する繰り返し単位を含む重合体。
Raは、炭素数1~20の1価炭化水素基であり、Raが2つ以上存在する場合、隣接する2つのRaが、互いに結合してこれらが結合する炭素原子と共に脂環構造を形成してもよい。また、前記1価炭化水素基を構成するメチレン基が、エーテル結合又はカルボニル基で置換されていてもよい。
Rbは、水素原子又は酸不安定基である。
Xは、ハロゲン原子である。
n及びmは、1≦n≦4、0≦m≦3及び1≦n+m≦4を満たす整数である。
破線は、重合体の主鎖との結合手である。)
5.前記繰り返し単位が、下記式(a)で表されるものである4の重合体。
6.X1が、単結合である4又は5の重合体。
7.Xが、ヨウ素原子である4~6のいずれかの重合体。
8.更に、酸によって極性が変化する基を有する繰り返し単位を含む4~7のいずれかの重合体。
9.酸によって極性が変化する基を有する繰り返し単位が、下記式(b1)又は(b2)で表されるものである8の重合体。
Y1は、単結合、フェニレン基若しくはナフチレン基、又はエーテル結合、エステル結合若しくはラクトン環を含む炭素数1~12の連結基である。
Y2は、単結合、エステル結合又はアミド結合である。
R1及びR2は、それぞれ独立に、酸不安定基である。
R3は、フッ素原子、トリフルオロメチル基、シアノ基、炭素数1~6のアルキル基、炭素数1~6のアルコキシ基、炭素数2~7のアシル基、炭素数2~7のアシロキシ基、又は炭素数2~7のアルコキシカルボニル基である。
R4は、単結合、又は炭素数1~6のアルキレン基であり、その炭素原子の一部が、エーテル結合又はエステル結合で置換されていてもよい。
pは、1又は2である。
qは、0~4の整数である。)
10.更に、ヒドロキシ基、カルボキシ基、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、エーテル結合、エステル結合、スルホン酸エステル結合、シアノ基、アミド基、-O-C(=O)-S-及び-O-C(=O)-NH-から選ばれる密着性基を含む繰り返し単位を少なくとも1種含む4~9のいずれかの重合体。
11.更に、下記式(d1)~(d3)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4~10のいずれかの重合体。
R11及びR12は、それぞれ独立に、ヘテロ原子を含んでいてもよい炭素数1~20の1価炭化水素基である。R11とR12とは、互いに結合してこれらが結合する硫黄原子と共に環を形成してもよい。
L1は、単結合、フェニレン基、-C(=O)-L11-L12-又は-O-L12-であり、L11は、-O-又は-NH-であり、L12は、炭素数1~6の2価脂肪族炭化水素基、又はフェニレン基であり、前記2価脂肪族炭化水素基は、カルボニル基、エステル結合、エーテル結合又はヒドロキシ基を含んでいてもよい。
L2は、単結合、又は-L21-C(=O)-O-であり、L21は、ヘテロ原子を含んでいてもよい炭素数1~20の2価炭化水素基である。
L3は、単結合、メチレン基、エチレン基、フェニレン基、フッ素化フェニレン基、-C(=O)-L31-L32-又は-O-L32-であり、L31は、-O-又は-NH-であり、L32は、炭素数1~6の2価脂肪族炭化水素基、又はフェニレン基であり、前記2価脂肪族炭化水素基は、カルボニル基、エステル結合、エーテル結合又はヒドロキシ基を含んでいてもよい。
M-は、非求核性対向イオンである。
Q+は、下記式(d4)で表されるスルホニウムカチオン、又は下記式(d5)で表されるヨードニウムカチオンである。
12.4~10のいずれかの重合体を含むベース樹脂、有機溶剤、及び酸発生剤を含むレジスト材料。
13.11の重合体を含むベース樹脂、及び有機溶剤を含むレジスト材料。
14.更に、クエンチャーを含む12又は13のレジスト材料。
15.更に、界面活性剤を含む12~14のいずれかのレジスト材料。
16.12~15のいずれかのレジスト材料を基板上に塗布し、加熱処理をしてレジスト膜を形成する工程と、前記レジスト膜を高エネルギー線で露光する工程と、現像液を用いて露光したレジスト膜を現像する工程とを含むパターン形成方法。
17.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(EB)、又は波長3~15nmのEUVである16のパターン形成方法。
本発明の重合体は、側鎖に下記式(B)で表される部分構造を有する繰り返し単位を含むものである。
本発明のレジスト材料は、前述した重合体を含むベース樹脂、及び有機溶剤を含むものである。前記ベース樹脂は、組成比率、Mw、分子量分布が異なる2つ以上の前記重合体をブレンドしたものであってもよい。
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等が挙げられる。これらの溶剤は、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、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(以下、添加型酸発生剤ともいう。)を含んでもよい。前記添加型酸発生剤としては、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。なお、ベース樹脂が繰り返し単位d1~d3を含む場合、すなわち酸発生剤がベース樹脂中に含まれている場合は、添加型酸発生剤は含まなくてもよい。
Rf11~Rf14は、それぞれ独立に、水素原子、フッ素原子又はトリフルオロメチル基であるが、これらのうち少なくとも1つはフッ素原子又はトリフルオロメチル基である。また、Rf11とRf12とが合わさって、カルボニル基を形成してもよい。
本発明のレジスト材料は、更に、クエンチャー、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、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。
IR(D-ATR): ν= 3403, 3084, 3057, 3023, 1834, 1750, 1717, 1658, 1623, 1569, 1543, 1442, 1414, 1394, 1370, 1323, 1303, 1258, 1235, 1202, 1126, 1100, 1038, 1023, 994, 915, 863, 804, 757, 734, 697, 664, 584, 542, 530 cm-1.
1H-NMR(600MHz in DMSO-d6): δ= 9.64(1H, s), 7.89(1H, s), 7.73(1H, s), 6.90(1H, dd), 5.89(1H, d), 5.28(1H, d) ppm.
レジスト材料に用いる重合体として、各モノマーを組み合わせてシクロペンタノン溶剤下で共重合反応を行い、ヘキサンに晶出し、更にヘキサンで洗浄を繰り返した後に、単離、乾燥して、以下に示す重合体(ポリマー1~19、比較ポリマー1~7)を得た。得られた重合体の組成は、1H-NMR及び13C-NMRにて確認した。また、Mw及びMnは、溶剤としてテトラヒドロフラン(THF)を用いたGPCによるポリスチレン換算値である。
界面活性剤としてスリーエム社製FC-4430を100ppm溶解させた溶剤に、表1及び2に示される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、レジスト材料を調製した。
・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)
CyH(シクロヘキサノン)
PGME(プロピレングリコールモノメチルエーテル)
DAA(ジアセトンアルコール)
[実施例3-1~3-19、比較例2-1~2-7]
表1及び2に示す各レジスト材料を、信越化学工業(株)製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20nm膜厚で形成したSi基板上にスピンコートし、ホットプレートを用いて105℃で60秒間プリベークして膜厚60nmのレジスト膜を作製した。これに、ASML社製EUVスキャナーNXE3300(NA0.33、σ0.9/0.6、クアドルポール照明、ウエハー上寸法がピッチ46nm、+20%バイアスのホールパターンのマスク)を用いて露光し、ホットプレート上で表1及び2記載の温度で60秒間PEBを行い、2.38質量%TMAH水溶液で30秒間現像を行って、寸法23nmのホールパターンを形成した。
(株)日立ハイテクノロジーズ製の測長SEM(CG5000)を用いて、ホールが23nmで形成されるときの露光量を測定してこれを感度とし、また、このときのホール50個の寸法を測定し、寸法バラツキ(CDU、3σ)を求めた。結果を表1及び2に併記する。
Claims (14)
- Rbが、酸不安定基である請求項1記載の単量体。
- Rbが、酸不安定基である請求項3記載の重合体。
- 更に、酸によって極性が変化する基を有する繰り返し単位を含む請求項3又は4記載の重合体。
- 酸によって極性が変化する基を有する繰り返し単位が、下記式(b1)又は(b2)で表されるものである請求項5記載の重合体。
Y1は、単結合、フェニレン基若しくはナフチレン基、又はエーテル結合、エステル結合若しくはラクトン環を含む炭素数1~12の連結基である。
Y2は、単結合、エステル結合又はアミド結合である。
R1及びR2は、それぞれ独立に、酸不安定基である。
R3は、フッ素原子、トリフルオロメチル基、シアノ基、炭素数1~6のアルキル基、炭素数1~6のアルコキシ基、炭素数2~7のアシル基、炭素数2~7のアシロキシ基、又は炭素数2~7のアルコキシカルボニル基である。
R4は、単結合、又は炭素数1~6のアルキレン基であり、その炭素原子の一部が、エーテル結合又はエステル結合で置換されていてもよい。
pは、1又は2である。
qは、0~4の整数である。) - 更に、ヒドロキシ基、カルボキシ基、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、エーテル結合、エステル結合、スルホン酸エステル結合、シアノ基、アミド基、-O-C(=O)-S-及び-O-C(=O)-NH-から選ばれる密着性基を含む繰り返し単位を少なくとも1種含む請求項3~6のいずれか1項記載の重合体。
- 更に、下記式(d1)~(d3)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3~7のいずれか1項記載の重合体。
R11及びR12は、それぞれ独立に、ヘテロ原子を含んでいてもよい炭素数1~20の1価炭化水素基である。R11とR12とは、互いに結合してこれらが結合する硫黄原子と共に環を形成してもよい。
L1は、単結合、フェニレン基、-C(=O)-L11-L12-又は-O-L12-であり、L11は、-O-又は-NH-であり、L12は、炭素数1~6の2価脂肪族炭化水素基、又はフェニレン基であり、前記2価脂肪族炭化水素基は、カルボニル基、エステル結合、エーテル結合又はヒドロキシ基を含んでいてもよい。
L2は、単結合、又は-L21-C(=O)-O-であり、L21は、ヘテロ原子を含んでいてもよい炭素数1~20の2価炭化水素基である。
L3は、単結合、メチレン基、エチレン基、フェニレン基、フッ素化フェニレン基、-C(=O)-L31-L32-又は-O-L32-であり、L31は、-O-又は-NH-であり、L32は、炭素数1~6の2価脂肪族炭化水素基、又はフェニレン基であり、前記2価脂肪族炭化水素基は、カルボニル基、エステル結合、エーテル結合又はヒドロキシ基を含んでいてもよい。
M-は、非求核性対向イオンである。
Q+は、下記式(d4)で表されるスルホニウムカチオン、又は下記式(d5)で表されるヨードニウムカチオンである。
- 請求項3~7のいずれか1項記載の重合体を含むベース樹脂、有機溶剤、及び酸発生剤を含むレジスト材料。
- 請求項8記載の重合体を含むベース樹脂、及び有機溶剤を含むレジスト材料。
- 更に、クエンチャーを含む請求項9又は10記載のレジスト材料。
- 更に、界面活性剤を含む請求項9~11のいずれか1項記載のレジスト材料。
- 請求項9~12のいずれか1項記載のレジスト材料を基板上に塗布し、加熱処理をしてレジスト膜を形成する工程と、前記レジスト膜を高エネルギー線で露光する工程と、現像液を用いて露光したレジスト膜を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の極端紫外線である請求項13記載のパターン形成方法。
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