JP2021047396A - 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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- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 150000008053 sultones Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-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
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
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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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
- C08F212/24—Phenols or alcohols
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1805—C5-(meth)acrylate, e.g. pentyl (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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D125/00—Coating compositions based on homopolymers or 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; Coating compositions based on derivatives of such polymers
- C09D125/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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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
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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Abstract
Description
1.ベースポリマー、及び
ヨウ素原子又は臭素原子で置換されたフェノール化合物に由来するアニオンと、2,5,8,9−テトラアザ−1−ホスファビシクロ[3.3.3]ウンデカン化合物、ビグアニド化合物又はホスファゼン化合物に由来するカチオンとからなる塩
を含むレジスト材料。
2.前記塩が、下記式(A)で表されるものである1のレジスト材料。
XBIは、ヨウ素原子又は臭素原子である。
R1は、ヒドロキシ基、フッ素原子又は塩素原子で置換されていてもよい炭素数1〜6の飽和ヒドロカルビル基、フッ素原子又は塩素原子で置換されていてもよい炭素数1〜6の飽和ヒドロカルビルオキシ基、フッ素原子又は塩素原子で置換されていてもよい炭素数2〜6の飽和ヒドロカルビルオキシカルボニル基、ホルミル基、フッ素原子又は塩素原子で置換されていてもよい炭素数2〜6の飽和ヒドロカルビルカルボニル基、フッ素原子又は塩素原子で置換されていてもよい炭素数2〜6の飽和ヒドロカルビルカルボニルオキシ基、フッ素原子又は塩素原子で置換されていてもよい炭素数1〜4の飽和ヒドロカルビルスルホニルオキシ基、炭素数6〜10のアリール基、フッ素原子、塩素原子、アミノ基、ニトロ基、シアノ基、−N(R1A)−C(=O)−R1B又は−N(R1A)−C(=O)−O−R1Bである。R1Aは、水素原子又は炭素数1〜6の飽和ヒドロカルビル基である。R1Bは、炭素数1〜6の飽和ヒドロカルビル基又は炭素数2〜8の不飽和脂肪族ヒドロカルビル基である。
A+は、下記式(A)−1、(A)−2又は(A)−3で表されるカチオンである。
R14〜R21は、それぞれ独立に、水素原子、ヘテロ原子を含んでいてもよい炭素数1〜24のヒドロカルビル基であり、R14とR15と、R15とR16と、R16とR17と、R17とR18と、R18とR19と、R19とR20と、又はR20とR21とが、互いに結合してこれらが結合する窒素原子と共に、又はこれらが結合する窒素原子とその間の炭素原子と共に環を形成してもよく、該環の中にエーテル結合を含んでいてもよい。
R22〜R29は、それぞれ独立に、水素原子、ヘテロ原子を含んでいてもよい炭素数1〜24のヒドロカルビル基であり、R22とR23と、R23とR24と、R24とR25と、R25とR26と、R26とR27と、又はR27とR28とが、互いに結合してこれらが結合する窒素原子と共に、又はこれらが結合する窒素原子とその間のリン原子と共に環を形成してもよく、R22とR23と、R24とR25と、R26とR27と、又はR28とR29とが合わさって、下記式(A)−3−1で表される基を形成してもよく、R22が水素原子である場合は、R23が下記式(A)−3−2で表される基であってもよい。
3.更に、スルホン酸、スルホンイミド又はスルホンメチドを発生する酸発生剤を含む1又は2のレジスト材料。
4.前記ベースポリマーが、下記式(a1)で表される繰り返し単位又は下記式(a2)で表される繰り返し単位を含むものである1〜3のいずれかのレジスト材料。
5.化学増幅ポジ型レジスト材料である4のレジスト材料。
6.前記ベースポリマーが、酸不安定基を含まないものである1〜3のいずれかのレジスト材料。
7.化学増幅ネガ型レジスト材料である6のレジスト材料。
8.前記ベースポリマーが、下記式(f1)〜(f3)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1〜7のいずれかのレジスト材料。
Z1は、単結合、フェニレン基、−O−Z11−、−C(=O)−O−Z11−又は−C(=O)−NH−Z11−であり、Z11は、炭素数1〜6の脂肪族ヒドロカルビレン基又はフェニレン基であり、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。
Z2は、単結合、−Z21−C(=O)−O−、−Z21−O−又は−Z21−O−C(=O)−であり、Z21は、炭素数1〜12の飽和ヒドロカルビレン基であり、カルボニル基、エステル結合又はエーテル結合を含んでいてもよい。
Z3は、単結合、メチレン基、エチレン基、フェニレン基、フッ素化されたフェニレン基、−O−Z31−、−C(=O)−O−Z31−又は−C(=O)−NH−Z31−であり、Z31は、炭素数1〜6の脂肪族ヒドロカルビレン基、フェニレン基、フッ素化されたフェニレン基、又はトリフルオロメチル基で置換されたフェニレン基であり、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。
R51〜R58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のヒドロカルビル基である。また、R53、R54及びR55のいずれか2つ又はR56、R57及びR58のいずれか2つが、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。
RHFは、水素原子又はトリフルオロメチル基である。
M-は、非求核性対向イオンである。)
9.更に、有機溶剤を含む1〜8のいずれかのレジスト材料。
10.更に、界面活性剤を含む1〜9のいずれかのレジスト材料。
11.1〜10のいずれかのレジスト材料を用いて基板上に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、前記露光したレジスト膜を、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。
12.前記高エネルギー線が、波長193nmのArFエキシマレーザー光又は波長248nmのKrFエキシマレーザー光である11のパターン形成方法。
13.前記高エネルギー線が、EB又は波長3〜15nmのEUVである11のパターン形成方法。
本発明のレジスト材料は、ベースポリマー、及びヨウ素原子又は臭素原子で置換されたフェノール化合物(以下、ヨウ素化又は臭素化フェノール化合物ともいう。)に由来するアニオンと、2,5,8,9−テトラアザ−1−ホスファビシクロ[3.3.3]ウンデカン化合物、ビグアニド化合物又はホスファゼン化合物に由来するカチオンとからなる塩(以下、これらを総称してヨウ素化又は臭素化フェノール塩ともいう。)とを含むものである。
る。
本発明のレジスト材料に含まれるベースポリマーは、ポジ型レジスト材料の場合、酸不安定基を有する繰り返し単位を含む。前記酸不安定基を有する繰り返し単位としては、下記式(a1)で表される繰り返し単位(以下、繰り返し単位a1ともいう。)又は下記式(a2)で表される繰り返し単位(以下、繰り返し単位a2ともいう。)が好ましい。
本発明のレジスト材料は、強酸を発生する酸発生剤(以下、添加型酸発生剤ともいう。)を含んでもよい。ここでいう強酸とは、化学増幅ポジ型レジスト材料の場合はベースポリマーの酸不安定基の脱保護反応を起こすのに十分な酸性度を有している化合物、化学増幅ネガ型レジスト材料の場合は酸による極性変化反応又は架橋反応を起こすのに十分な酸性度を有している化合物を意味する。このような酸発生剤を含むことで、前述したヨウ素化又は臭素化フェノール塩がクエンチャーとして機能し、本発明のレジスト材料が、化学増幅ポジ型レジスト材料又は化学増幅ネガ型レジスト材料として機能することができる。
本発明のレジスト材料には、有機溶剤を配合してもよい。前記有機溶剤としては、前述した各成分及び後述する各成分が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、特開2008−111103号公報の段落[0144]〜[0145]に記載の、シクロヘキサノン、シクロペンタノン、メチル−2−n−ペンチルケトン、2−ヘプタノン等のケトン類、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。
前述した成分に加えて、界面活性剤、溶解阻止剤、架橋剤等を目的に応じて適宜組み合わせて配合してポジ型レジスト材料及びネガ型レジスト材料を構成することによって、露光部では前記ベースポリマーが触媒反応により現像液に対する溶解速度が加速されるので、極めて高感度のポジ型レジスト材料及びネガ型レジスト材料とすることができる。この場合、レジスト膜の溶解コントラスト及び解像性が高く、露光余裕度があり、プロセス適応性に優れ、露光後のパターン形状が良好でありながら、特に酸拡散を抑制できることから粗密寸法差が小さく、これらのことから実用性が高く、超LSI用レジスト材料として非常に有効なものとすることができる。
本発明の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。例えば、パターン形成方法としては、前述したレジスト材料を用いて基板上に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方法が挙げられる。
各モノマーを組み合わせて、溶剤であるTHF中で共重合反応を行い、メタノールに晶出し、更にヘキサンで洗浄を繰り返した後、単離、乾燥して、以下に示す組成のベースポリマー(ポリマー1〜4)を得た。得られたベースポリマーの組成は1H−NMRにより、Mw及びMw/MnはGPC(溶剤:THF、標準:ポリスチレン)により確認した。
(1)レジスト材料の調製
界面活性剤としてスリーエム社製界面活性剤FC-4430を100ppm溶解させた溶剤に、表1〜3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てレジスト材料を調製した。なお、実施例1〜18及び比較例1〜6のレジスト材料はポジ型であり、実施例19及び比較例7のレジスト材料はネガ型である。
・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)
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)
表1〜3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%)を膜厚20nm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50nmのレジスト膜を作製した。これを、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EUVで露光し、ホットプレート上で表1〜3に記載の温度で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、実施例1〜18及び比較例1〜6では寸法23nmのホールパターンを、実施例19及び比較例7では寸法23nmのドットパターンを得た。
(株)日立ハイテクノロジーズ製の測長SEM(CG5000)を用いて、ホール又はドット寸法が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、このときのホール又はドット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1〜3に併記する。
Claims (13)
- ベースポリマー、及び
ヨウ素原子又は臭素原子で置換されたフェノール化合物に由来するアニオンと、2,5,8,9−テトラアザ−1−ホスファビシクロ[3.3.3]ウンデカン化合物、ビグアニド化合物又はホスファゼン化合物に由来するカチオンとからなる塩
を含むレジスト材料。 - 前記塩が、下記式(A)で表されるものである請求項1記載のレジスト材料。
XBIは、ヨウ素原子又は臭素原子である。
R1は、ヒドロキシ基、フッ素原子又は塩素原子で置換されていてもよい炭素数1〜6の飽和ヒドロカルビル基、フッ素原子又は塩素原子で置換されていてもよい炭素数1〜6の飽和ヒドロカルビルオキシ基、フッ素原子又は塩素原子で置換されていてもよい炭素数2〜6の飽和ヒドロカルビルオキシカルボニル基、ホルミル基、フッ素原子又は塩素原子で置換されていてもよい炭素数2〜6の飽和ヒドロカルビルカルボニル基、フッ素原子又は塩素原子で置換されていてもよい炭素数2〜6の飽和ヒドロカルビルカルボニルオキシ基、フッ素原子又は塩素原子で置換されていてもよい炭素数1〜4の飽和ヒドロカルビルスルホニルオキシ基、炭素数6〜10のアリール基、フッ素原子、塩素原子、アミノ基、ニトロ基、シアノ基、−N(R1A)−C(=O)−R1B又は−N(R1A)−C(=O)−O−R1Bである。R1Aは、水素原子又は炭素数1〜6の飽和ヒドロカルビル基である。R1Bは、炭素数1〜6の飽和ヒドロカルビル基又は炭素数2〜8の不飽和脂肪族ヒドロカルビル基である。
A+は、下記式(A)−1、(A)−2又は(A)−3で表されるカチオンである。
R14〜R21は、それぞれ独立に、水素原子、ヘテロ原子を含んでいてもよい炭素数1〜24のヒドロカルビル基であり、R14とR15と、R15とR16と、R16とR17と、R17とR18と、R18とR19と、R19とR20と、又はR20とR21とが、互いに結合してこれらが結合する窒素原子と共に、又はこれらが結合する窒素原子とその間の炭素原子と共に環を形成してもよく、該環の中にエーテル結合を含んでいてもよい。
R22〜R29は、それぞれ独立に、水素原子、ヘテロ原子を含んでいてもよい炭素数1〜24のヒドロカルビル基であり、R22とR23と、R23とR24と、R24とR25と、R25とR26と、R26とR27と、又はR27とR28とが、互いに結合してこれらが結合する窒素原子と共に、又はこれらが結合する窒素原子とその間のリン原子と共に環を形成してもよく、R22とR23と、R24とR25と、R26とR27と、又はR28とR29とが合わさって、下記式(A)−3−1で表される基を形成してもよく、R22が水素原子である場合は、R23が下記式(A)−3−2で表される基であってもよい。
- 更に、スルホン酸、スルホンイミド又はスルホンメチドを発生する酸発生剤を含む請求項1又は2記載のレジスト材料。
- 化学増幅ポジ型レジスト材料である請求項4記載のレジスト材料。
- 前記ベースポリマーが、酸不安定基を含まないものである請求項1〜3のいずれか1項記載のレジスト材料。
- 化学増幅ネガ型レジスト材料である請求項6記載のレジスト材料。
- 前記ベースポリマーが、下記式(f1)〜(f3)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1〜7のいずれか1項記載のレジスト材料。
Z1は、単結合、フェニレン基、−O−Z11−、−C(=O)−O−Z11−又は−C(=O)−NH−Z11−であり、Z11は、炭素数1〜6の脂肪族ヒドロカルビレン基又はフェニレン基であり、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。
Z2は、単結合、−Z21−C(=O)−O−、−Z21−O−又は−Z21−O−C(=O)−であり、Z21は、炭素数1〜12の飽和ヒドロカルビレン基であり、カルボニル基、エステル結合又はエーテル結合を含んでいてもよい。
Z3は、単結合、メチレン基、エチレン基、フェニレン基、フッ素化されたフェニレン基、−O−Z31−、−C(=O)−O−Z31−又は−C(=O)−NH−Z31−であり、Z31は、炭素数1〜6の脂肪族ヒドロカルビレン基、フェニレン基、フッ素化されたフェニレン基、又はトリフルオロメチル基で置換されたフェニレン基であり、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。
R51〜R58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のヒドロカルビル基である。また、R53、R54及びR55のいずれか2つ又はR56、R57及びR58のいずれか2つが、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。
RHFは、水素原子又はトリフルオロメチル基である。
M-は、非求核性対向イオンである。) - 更に、有機溶剤を含む請求項1〜8のいずれか1項記載のレジスト材料。
- 更に、界面活性剤を含む請求項1〜9のいずれか1項記載のレジスト材料。
- 請求項1〜10のいずれか1項記載のレジスト材料を用いて基板上に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、前記露光したレジスト膜を、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、波長193nmのArFエキシマレーザー光又は波長248nmのKrFエキシマレーザー光である請求項11記載のパターン形成方法。
- 前記高エネルギー線が、電子線又は波長3〜15nmの極端紫外線である請求項11記載のパターン形成方法。
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