JPWO2016143635A1 - 化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜、パターン形成方法及び化合物又は樹脂の精製方法 - Google Patents
化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜、パターン形成方法及び化合物又は樹脂の精製方法 Download PDFInfo
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- MANNXDXMUHZSRP-UHFFFAOYSA-M tetramethylazanium;trifluoromethanesulfonate Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)C(F)(F)F MANNXDXMUHZSRP-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000005068 thioepoxy group Chemical group S(O*)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- UPWIJTYOHJOEOX-UHFFFAOYSA-M trifluoromethanesulfonate;trinaphthalen-1-ylsulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2C([S+](C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 UPWIJTYOHJOEOX-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
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- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
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- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
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- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
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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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C09D161/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols with polyhydric phenols
-
- 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
- G03F7/004—Photosensitive materials
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- G03F7/094—Multilayer resist systems, e.g. planarising layers
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- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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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
- G03F7/2012—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 using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
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Abstract
Description
すなわち、本発明は、次のとおりである。
[1]
下記式(1)で表される、化合物。
[2]
前記R6の少なくとも1つが、水酸基又はチオール基である、[1]に記載の化合物。
[3]
前記R2の少なくとも1つ及び/又は前記R3の少なくとも1つが、水酸基及び/又はチオール基である、[1]又は[2]に記載の化合物。
[4]
前記式(1)で表される化合物が、下記式(1a)で表される化合物である、[1]〜[3]のいずれかに記載の化合物。
[5]
前記式(1a)で表される化合物が、下記式(1b)で表される化合物である、[4]に記載の化合物。
[6]
前記式(1b)で表される化合物が、下記式(1c)で表される化合物である、[5]に記載の化合物。
[7]
前記式(1c)で表される化合物が、下記式(1d)で表される化合物である、[6]に記載の化合物。
[8]
前記式(1d)で表される化合物が、下記式(1e)で表される化合物である、[7]に記載の化合物。
[9]
下記式(1f)で表される、[8]に記載の化合物。
[1]〜[9]のいずれかに記載の化合物をモノマーとして得られる、樹脂。
[11]
[1]〜[9]のいずれかに記載の化合物を架橋反応性のある化合物と反応させることによって得られる、請求項10に記載の樹脂。
[12]
前記架橋反応性のある化合物が、アルデヒド、ケトン、カルボン酸、カルボン酸ハライド、ハロゲン含有化合物、アミノ化合物、イミノ化合物、イソシアネート及び不飽和炭化水素基含有化合物からなる群より選ばれる1種以上である、[11]に記載の樹脂。
[13]
下記式(2)で表される構造を有する、樹脂。
[14]
[1]〜[9]のいずれかに記載の化合物を含有する、リソグラフィー用下層膜形成材料。
[15]
[10]〜[13]のいずれかに記載の樹脂を含有する、リソグラフィー用下層膜形成材料。
[16]
有機溶媒をさらに含有する、[14]又は[15]に記載のリソグラフィー用下層膜形成材料。
[17]
酸発生剤をさらに含有する、[14]〜[16]のいずれかに記載のリソグラフィー用下層膜形成材料。
[18]
架橋剤をさらに含有する、[14]〜[17]のいずれかに記載のリソグラフィー用下層膜形成材料。
[19]
[14]〜[18]のいずれかに記載のリソグラフィー用下層膜形成材料から形成される、リソグラフィー用下層膜。
[20]
基板上に、[14]〜[18]のいずれかに記載の下層膜形成材料を用いて下層膜を形成する工程(A−1)と、
前記下層膜上に、少なくとも1層のフォトレジスト層を形成する工程(A−2)と、
前記工程(A−2)の後、該フォトレジスト層の所定の領域に放射線を照射し、現像を行う工程(A−3)と、
を有する、レジストパターン形成方法。
[21]
基板上に、[14]〜[18]のいずれかに記載の下層膜形成材料を用いて下層膜を形成する工程(B−1)と、
前記下層膜上に、珪素原子を含有するレジスト中間層膜材料を用いて中間層膜を形成する工程(B−2)と、
前記中間層膜上に、少なくとも1層のフォトレジスト層を形成する工程(B−3)と、
前記工程(B−3)の後、前記フォトレジスト層の所定の領域に放射線を照射し、現像してレジストパターンを形成する工程(B−4)と、
前記工程(B−4)の後、前記レジストパターンをマスクとして前記中間層膜をエッチングし、得られた中間層膜パターンをエッチングマスクとして前記下層膜をエッチングし、得られた下層膜パターンをエッチングマスクとして基板をエッチングすることで基板にパターンを形成する工程(B−5)と、
を有する、回路パターン形成方法。
[22]
[1]〜[9]のいずれかに記載の化合物、又は、請求項10〜13のいずれかに記載の樹脂の精製方法であって、
水と任意に混和しない有機溶媒及び、前記化合物又は前記樹脂を含む溶液と、酸性の水溶液と、を接触させて抽出する工程を含む、精製方法。
[23]
前記酸性の水溶液が、塩酸、硫酸、硝酸及びリン酸からなる群より選ばれる1種以上の鉱酸水溶液である、又は、酢酸、プロピオン酸、蓚酸、マロン酸、コハク酸、フマル酸、マレイン酸、酒石酸、クエン酸、メタンスルホン酸、フェノールスルホン酸、p−トルエンスルホン酸及びトリフルオロ酢酸からなる群より選ばれる1種以上の有機酸水溶液である、[22]に記載の精製方法。
[24]
前記水と任意に混和しない有機溶媒が、トルエン、2−ヘプタノン、シクロヘキサノン、シクロペンタノン、メチルイソブチルケトン、プロピレングリコールモノメチルエーテルアセテート又は酢酸エチルである、[22]又は[23]に記載の精製方法。
[25]
前記溶液と酸性の水溶液とを接触させて抽出する工程の後、さらに水による抽出処理を行う工程を含む、[22]〜[24]のいずれかに記載の精製方法。
本実施形態の化合物は、下記式(1)で表される。本実施形態の化合物は、このように構成されているため、フォトレジスト下層膜を形成する際に、湿式プロセスが適用可能であり、耐熱性及びエッチング耐性に優れる。また、本実施形態の化合物は特定の構造を有するため、耐熱性が高く、溶媒溶解性も高い。そのため、本実施形態の化合物を用いることで、高温ベーク時の膜の劣化が抑制され、酸素プラズマエッチング等に対するエッチング耐性にも優れた下層膜を形成することができる。さらには、レジスト層との密着性にも優れるので、優れたレジストパターンを形成することができる。
R2〜R7は、各々独立して、炭素数1〜10の直鎖状、分岐状若しくは環状のアルキル基、炭素数6〜10のアリール基、炭素数2〜10のアルケニル基、チオール基及び水酸基からなる群より選択される1価の基である。ここで、R5の少なくとも1つは水酸基又はチオール基である。
m2、m3及びm6は、各々独立して0〜9の整数であり、m4及びm7は、各々独立して0〜8の整数であり、m5は、1〜9の整数である。
nは、1〜4の整数である。
p2〜p7は各々独立して0〜2の整数である。
m2’、m3’及びm6’は各々独立して0〜5の整数であり、m4’及びm7’は各々独立して0〜4の整数であり、m5’は1〜5の整数である。
m2’、m3’、m4’、及びm7’は上記式(1a)で説明したものと同義である。
m4’及びm7’は上記式(1a)で説明したものと同義である。
m4’及びm7’は上記式(1a)で説明したものと同義である。
R8〜R11は各々独立して、炭素数1〜10の直鎖状、分岐状若しくは環状のアルキル基、炭素数6〜10のアリール基、炭素数2〜10のアルケニル基、チオール基又は水酸基である。
m8〜m11は、各々独立して0〜6の整数である。
m2’〜m7’は、上記式(1a)で説明したものと同義である。
m4’〜m7’は、上記式(1a)で説明したものと同義である。
n’は0〜3の整数であり、n”は1〜4の整数である。各繰り返し単位の配列は任意である。
R8〜R11は各々独立して、炭素数1〜10の直鎖状、分岐状若しくは環状のアルキル基、炭素数6〜10のアリール基、炭素数2〜10のアルケニル基、チオール基又は水酸基である。
m8‘〜m11’は、各々独立して0〜4の整数である。
本実施形態の樹脂は、上記式(1)で表される化合物をモノマーとして得られる樹脂である。また、本実施形態の樹脂は、式(2)で表される構造を有する。
前記2価の基は、二重結合を有していてもよい。また、該基はヘテロ原子を有していてもよい。
R2〜R7は、各々独立して、炭素数1〜10の直鎖状、分岐状若しくは環状のアルキル基、炭素数6〜10のアリール基、炭素数2〜10のアルケニル基、チオール基又は水酸基であり、ここで、R5の少なくとも1つは水酸基又はチオール基である。
Lは、単結合又は炭素数1〜20の直鎖状若しくは分岐状のアルキレン基である。
m2、m3及びm6は、各々独立して0〜9の整数である。
m4及びm7は、各々独立して0〜8の整数である。
m5は、1〜9の整数である。
nは、1〜4の整数である。
p2〜p7は各々独立して0〜2の整数である。
本実施形態のリソグラフィー用下層膜形成材料は、上述した式(1)で表される化合物又は該化合物をモノマーとして得られる樹脂を含有する。すなわち、本実施形態のリソグラフィー用下層膜形成材料は、本実施形態の上記化合物又は樹脂を少なくとも含有するものである。このような構成を有するため、本実施形態のリソグラフィー用下層膜形成材料は、湿式プロセスが適用可能であり、耐熱性及びエッチング耐性に優れる。さらに、本実施形態のリソグラフィー用下層膜形成材料は上記化合物又は樹脂を用いているため、高温ベーク時の膜の劣化が抑制され、酸素プラズマエッチング等に対するエッチング耐性にも優れた下層膜を形成することができる。さらに、本実施形態のリソグラフィー用下層膜形成材料はレジスト層との密着性にも優れるので、優れたレジストパターンを得ることができる。
1)下記一般式(P1a−1)、(P1a−2)、(P1a−3)又は(P1b)のオニウム塩、
2)下記一般式(P2)のジアゾメタン誘導体、
3)下記一般式(P3)のグリオキシム誘導体、
4)下記一般式(P4)のビススルホン誘導体、
5)下記一般式(P5)のN−ヒドロキシイミド化合物のスルホン酸エステル、
6)β−ケトスルホン酸誘導体、
7)ジスルホン誘導体、
8)ニトロベンジルスルホネート誘導体、
9)スルホン酸エステル誘導体
等が挙げられるが、これらに限定されない。なお、これらの酸発生剤は、1種を単独で、或いは2種以上を組み合わせて用いることができる。
本実施形態のリソグラフィー用下層膜は、本実施形態のリソグラフィー用下層膜形成材料から形成される。
本実施形態の化合物又は樹脂の精製方法は、水と任意に混和しない有機溶媒及び、前記化合物又は前記樹脂を含む溶液と、酸性の水溶液と、を接触させて抽出する工程を含む。より詳細には、本実施形態においては、式(1)で表される化合物又は該化合物をモノマーとして得られる樹脂を、水と任意に混和しない有機溶媒に溶解させ、その溶液を酸性水溶液と接触させ抽出処理を行うことにより、該化合物又は該樹脂と有機溶媒を含む溶液(A)に含まれる金属分を水相に移行させたのち、有機相と水相を分離して精製することができる。本実施形態の精製方法により、式(1)で表される化合物又は該化合物をモノマーとして得られる樹脂中の種々の金属の含有量を著しく低減させることができる。
有機元素分析により炭素濃度及び酸素濃度(質量%)を測定した。
装置:CHNコーダーMT−6(ヤナコ分析工業(株)製)
(分子量)
LC−MS分析により、Water社製Acquity UPLC/MALDI−Synapt HDMSを用いて測定した。
(ポリスチレン換算分子量)
ゲル浸透クロマトグラフィー(GPC)分析により、ポリスチレン換算の重量平均分子量(Mw)、数平均分子量(Mn)を求め、分散度(Mw/Mn)を求めた。
装置:Shodex GPC−101型(昭和電工(株)製)
カラム:KF−80M×3
溶離液:THF 1mL/min
温度:40℃
(溶解度)
23℃にて、化合物の1−メトキシ−2−プロパノール(PGME)及びプロピレングリコールモノメチルエーテルアセテート(PGMEA)に対する溶解量を測定し、その結果を以下の基準で評価した。
評価A:30wt%以上
評価B:20wt%以上30wt%未満
評価C:20wt%未満
攪拌機、冷却管及びビュレットを備えた内容積1000mLの容器を準備した。この容器に、4,4−ビフェノール(東京化成社製試薬)100g(537mmol)と、4−ビフェニルアルデヒド(三菱瓦斯化学社製)49g(269mmol)と、酢酸ブチル400mLとを仕込み、濃硫酸(96質量%、関東化学社製試薬)27g(269mmol)を加えて、反応液を調製した。この反応液を130℃で5時間撹拌して反応を行った。次に、反応液にイオン交換水2Lを加えて反応生成物を析出させ、室温まで冷却した。その後水酸化ナトリウム水溶液(24質量%)89g(534mmol)を加えて中和し、濾過を行って分離した。濾過により得られた固形物を乾燥させた後、酢酸エチル400mLに溶解させ、40℃でヘプタン400mLを1時間かけて滴下した。析出した固形物をろ別し、ろ液を炭酸ナトリウム水溶液(5質量%)400mLで6回洗浄した。洗浄後の有機層に水酸化ナトリウム水溶液(10質量%)400mLを加えて撹拌したのち、有機層を除去した。得られた水層に塩酸(36質量%)115gを滴下し、析出した固形物をろ別回収した。得られた固形物を酢酸エチル300mLに溶解させたのち、イオン交換水200mLで3回洗浄することによって、残留した塩酸を除去した。得られた酢酸エチル溶液を減圧乾燥することで、下記式で表される目的化合物群(TriF−3)108gを得た。
なお、400MHz−1H−NMRにより以下のピークが見出された。
1H−NMR:(d−DMSO、内部標準TMS)
δ(ppm)9.3〜9.4(4.4H,O−H)、6.7〜7.7(25.7H,Ph−H)、6.0〜6.2(1.2H,C−H)
また、LC−MSでは表1に示すピークと、対応する分子量が観測された。
実施例1で合成した(TriF−3)100gをカラムクロマトグラフィーで分離することで、下記式で表される目的化合物群(TriF−2)11.3gを得た。
なお、400MHz−1H−NMRにより以下のピークが見出された。
1H−NMR:(d−DMSO、内部標準TMS)
δ(ppm)9.3〜9.4(6.1H,O−H)、6.7〜7.7(38.8H,Ph−H)、6.0〜6.2(2.1H,C−H)
また、LC−MSでは表2に示すピークと、対応する分子量が観測された。
実施例2で合成した(TriF−2)10gをカラムクロマトグラフィーで分離することで、下記式で表される目的化合物(TriF−1)8.4gを得た。
なお、400MHz−1H−NMRにより以下のピークが見出された。
1H−NMR:(d−DMSO、内部標準TMS)
δ(ppm)9.3(6H,O−H)、6.7〜7.7(38H,Ph−H)、6.0〜6.1(2H,C−H)
また、LC−MSでは表3に示すピークと、対応する分子量が観測された。
攪拌機、冷却管及びビュレットを備えた内容積1000mLの容器を準備した。この容器に、4,4−ビフェノール(東京化成社製試薬)100g(537mmol)と、4−ビフェニルアルデヒド(三菱瓦斯化学社製)9.8g(53.8mmol)と、プロピレングリコールモノメチルエーテル400mLとを仕込み、濃硫酸(96質量%、関東化学社製試薬)5.4g(53.8mmol)を加えて、反応液を調製した。この反応液を120℃で5時間撹拌して反応を行った。次に、反応液にイオン交換水2Lに投入し、反応生成物を析出させ、室温まで冷却した。その後水酸化ナトリウム水溶液(24質量%)89g(534mmol)を加えて中和し、濾過を行って分離した。濾過により得られた固形物を乾燥させた後、酢酸ブチル400mLに溶解させ、40℃でヘプタン400mLを1時間かけて滴下した。析出した固形物をろ別し、ろ液を炭酸ナトリウム水溶液(5質量%)400mLで6回洗浄した。洗浄後の有機層にオルソキシレン400mLを加えて撹拌したのち、100℃で減圧濃縮を行うことで析出した固形物をろ別回収した。得られた固形物を減圧乾燥することで、下記式で表される目的化合物群(Tri−1)58gを得た。
なお、400MHz−1H−NMRにより以下のピークが見出された。
1H−NMR:(d−DMSO、内部標準TMS)
δ(ppm)9.3(6H,O−H)、6.7〜7.7(38.7H,Ph−H)、6.0〜6.1(2.1H,C−H)
また、LC−MSでは表4に示すピークと、対応する分子量が観測された。
攪拌機、冷却管及びビュレットを備えた内容積1000mLの容器を準備した。この容器に、4,4−ビフェノール(東京化成社製試薬)10g(53.7mmol)と、4−ビフェニルアルデヒド(三菱瓦斯化学社製)98g(538mmol)と、プロピレングリコールモノメチルエーテル400mLとを仕込み、濃硫酸(96質量%、関東化学社製試薬)2.7g(26.9mmol)を加えて、反応液を調製した。この反応液を100℃で5時間撹拌して反応を行った。次に、反応液をイオン交換水2Lに投入し、反応生成物を析出させ、室温まで冷却した。その後水酸化ナトリウム水溶液(24質量%)49g(26.7mmol)を加えて中和し、濾過を行って分離した。濾過により得られた固形物を乾燥させた後、酢酸ブチル400mLに溶解させ、炭酸ナトリウム水溶液(5質量%)400mLで6回洗浄した。洗浄後の有機層にトルエン400mLを加えて撹拌したのち、100℃で減圧濃縮を行うことで析出した固形物をろ別回収した。得られた固形物を減圧乾燥することで、下記式で表される目的化合物群(TriF−3)72gを得た。
なお、400MHz−1H−NMRにより以下のピークが見出された。
1H−NMR:(d−DMSO、内部標準TMS)
δ(ppm)9.3〜9.4(8.3H,O−H)、6.7〜7.7(50.2H,Ph−H)、6.0〜6.2(3.2H,C−H)
また、LC−MSでは表5に示すピークと、対応する分子量が観測された。
エスアイアイ・ナノテクノロジー社製EXSTAR6000DSC装置を使用し、試料約5mgをアルミニウム製非密封容器に入れ、窒素ガス(30mL/min)気流中昇温速度10℃/minで600℃まで昇温した。その際の400℃での熱重量減少を測定し、その結果を以下の基準で評価した。実用上A〜Bが好ましい。得られた結果を表7に示す。
評価A:減少量0wt%以上20wt%未満
評価B:減少量20wt%以上40wt%未満
評価C:減少量40wt%以上
ジムロート冷却管、温度計及び攪拌翼を備えた、底抜きが可能な内容積10Lの四つ口フラスコを準備した。この四つ口フラスコに、窒素気流中、1,5−ジメチルナフタレン1.09kg(7mol、三菱ガス化学(株)製)、40質量%ホルマリン水溶液2.1kg(ホルムアルデヒドとして28mol、三菱ガス化学(株)製)及び98質量%硫酸(関東化学(株)製)0.97mLを仕込み、常圧下、100℃で還流させながら7時間反応させた。その後、希釈溶媒としてエチルベンゼン(和光純薬工業(株)製試薬特級)1.8kgを反応液に加え、静置後、下相の水相を除去した。さらに、中和及び水洗を行い、エチルベンゼン及び未反応の1,5−ジメチルナフタレンを減圧下で留去することにより、淡褐色固体のジメチルナフタレンホルムアルデヒド樹脂1.25kgを得た。
得られたジメチルナフタレンホルムアルデヒドの分子量は、Mn:562、Mw:1168、Mw/Mn:2.08であった。また、炭素濃度は84.2質量%、酸素濃度は8.3質量%であった。
得られた樹脂(CR−1)は、Mn:885、Mw:2220、Mw/Mn:4.17であった。また、炭素濃度は89.1質量%、酸素濃度は4.5質量%であった。
表8に示す組成となるように、リソグラフィー用下層膜形成材料を調製した。すなわち、下記の材料を使用した。
酸発生剤:みどり化学社製 ジターシャリーブチルジフェニルヨードニウムノナフルオロメタンスルホナート(DTDPI)
架橋剤:三和ケミカル社製 ニカラックMX270(ニカラック)
有機溶媒:プロピレングリコールモノメチルエーテルアセテートアセテート(PGMEA)
ノボラック:群栄化学社製 PSM4357
そして、下記に示す条件でエッチング試験を行い、エッチング耐性を評価した。評価結果を表8に併せて示す。
エッチング装置:サムコインターナショナル社製 RIE−10NR
出力:50W
圧力:20Pa
時間:2min
エッチングガス
Arガス流量:CF4ガス流量:O2ガス流量=50:5:5(sccm)
[エッチング耐性の評価]
エッチング耐性の評価は、以下の手順で行った。
まず、実施例6〜10で用いた化合物又は化合物群に代えてノボラック(群栄化学社製 PSM4357)を用いること以外は、実施例6〜10と同様の条件で、ノボラックの下層膜を作製した。そして、このノボラックの下層膜を対象として、上記のエッチング試験を行い、そのときのエッチングレートを測定した。
次に、実施例6〜10及び比較例1の下層膜を対象として、上記エッチング試験を同様に行い、そのときのエッチングレートを測定した。
そして、ノボラックの下層膜のエッチングレートを基準として、以下の評価基準でエッチング耐性を評価した。
[評価基準]
A:ノボラックの下層膜に比べてエッチングレートが、−10%未満
B:ノボラックの下層膜に比べてエッチングレートが、−10%〜+5%
C:ノボラックの下層膜に比べてエッチングレートが、+5%超
次に、実施例6〜10のリソグラフィー用下層膜形成材料の溶液を膜厚300nmのSiO2基板上に塗布して、240℃で60秒間、さらに400℃で120秒間ベークすることにより、膜厚70nmの下層膜を形成した。この下層膜上に、ArF用レジスト溶液を塗布し、130℃で60秒間ベークすることにより、膜厚140nmのフォトレジスト層を形成した。
なお、ArFレジスト溶液としては、下記式(11)の化合物:5質量部、トリフェニルスルホニウムノナフルオロメタンスルホナート:1質量部、トリブチルアミン:2質量部、及びPGMEA:92質量部を配合して調製したものを用いた。
式(11)の化合物は、次のように調製した。すなわち、2−メチル−2−メタクリロイルオキシアダマンタン4.15g、メタクリルロイルオキシ−γ−ブチロラクトン3.00g、3−ヒドロキシ−1−アダマンチルメタクリレート2.08g、アゾビスイソブチロニトリル0.38gを、テトラヒドロフラン80mLに溶解させて反応溶液とした。この反応溶液を、窒素雰囲気下、反応温度を63℃に保持して、22時間重合させた後、反応溶液を400mLのn−ヘキサン中に滴下した。このようにして得られる生成樹脂を凝固精製させ、生成した白色粉末をろ過し、減圧下40℃で一晩乾燥させて下記式で表される化合物を得た。
下層膜の形成を行わないこと以外は、実施例11〜15と同様にして、フォトレジスト層をSiO2基板上に直接形成し、ポジ型のレジストパターンを得た。
実施例11〜15及び比較例2のそれぞれについて、得られた55nmL/S(1:1)及び80nmL/S(1:1)のレジストパターンの形状を(株)日立製作所製電子顕微鏡(S−4800)を用いて観察した。現像後のレジストパターンの形状については、パターン倒れがなく、矩形性が良好なものを良好とし、そうでないものを不良として評価した。また、当該観察の結果、パターン倒れが無く、矩形性が良好な最小の線幅を解像性として評価の指標とした。さらに、良好なパターン形状を描画可能な最小の電子線エネルギー量を感度として、評価の指標とした。その結果を、表9に示す。
1000mL容量の四つ口フラスコ(底抜き型)に、実施例1〜3で得られたTriF−1、TriF−2、又はTriF−3をPGMEAに溶解させた溶液(10質量%)を150g仕込み、攪拌しながら80℃まで加熱した。次いで、蓚酸水溶液(pH1.3)37.5gを加え、5分間攪拌後、30分静置した。これにより油相と水相に分離したので、水相を除去した。この操作を1回繰り返した後、得られた油相に、超純水37.5gを仕込み、5分間攪拌後、30分静置し、水相を除去した。この操作を3回繰り返した後、80℃に加熱しながらフラスコ内を200hPa以下に減圧することで、残留水分及びPGMEAを濃縮留去した。その後、ELグレードのPGMEA(関東化学社製試薬)を希釈し、10質量%に濃度調整を行うことにより、金属含有量の低減されたTriF−1、TriF−2、又はTriF−3のPGMEA溶液を得た。
Claims (25)
- 前記R6の少なくとも1つが、水酸基又はチオール基である、請求項1に記載の化合物。
- 前記R2の少なくとも1つ及び/又は前記R3の少なくとも1つが、水酸基及び/又はチオール基である、請求項1又は2に記載の化合物。
- 請求項1〜9のいずれか1項に記載の化合物をモノマーとして得られる、樹脂。
- 請求項1〜9のいずれか1項に記載の化合物を架橋反応性のある化合物と反応させることによって得られる、請求項10に記載の樹脂。
- 前記架橋反応性のある化合物が、アルデヒド、ケトン、カルボン酸、カルボン酸ハライド、ハロゲン含有化合物、アミノ化合物、イミノ化合物、イソシアネート及び不飽和炭化水素基含有化合物からなる群より選ばれる1種以上である、請求項11に記載の樹脂。
- 下記式(2)で表される構造を有する、樹脂。
- 請求項1〜9のいずれか1項に記載の化合物を含有する、リソグラフィー用下層膜形成材料。
- 請求項10〜13のいずれか1項に記載の樹脂を含有する、リソグラフィー用下層膜形成材料。
- 有機溶媒をさらに含有する、請求項14又は15に記載のリソグラフィー用下層膜形成材料。
- 酸発生剤をさらに含有する、請求項14〜16のいずれか1項に記載のリソグラフィー用下層膜形成材料。
- 架橋剤をさらに含有する、請求項14〜17のいずれか1項に記載のリソグラフィー用下層膜形成材料。
- 請求項14〜18のいずれか1項に記載のリソグラフィー用下層膜形成材料から形成される、リソグラフィー用下層膜。
- 基板上に、請求項14〜18のいずれか1項に記載の下層膜形成材料を用いて下層膜を形成する工程(A−1)と、
前記下層膜上に、少なくとも1層のフォトレジスト層を形成する工程(A−2)と、
前記工程(A−2)の後、該フォトレジスト層の所定の領域に放射線を照射し、現像を行う工程(A−3)と、
を有する、レジストパターン形成方法。 - 基板上に、請求項14〜18のいずれか1項に記載の下層膜形成材料を用いて下層膜を形成する工程(B−1)と、
前記下層膜上に、珪素原子を含有するレジスト中間層膜材料を用いて中間層膜を形成する工程(B−2)と、
前記中間層膜上に、少なくとも1層のフォトレジスト層を形成する工程(B−3)と、
前記工程(B−3)の後、前記フォトレジスト層の所定の領域に放射線を照射し、現像してレジストパターンを形成する工程(B−4)と、
前記工程(B−4)の後、前記レジストパターンをマスクとして前記中間層膜をエッチングし、得られた中間層膜パターンをエッチングマスクとして前記下層膜をエッチングし、得られた下層膜パターンをエッチングマスクとして基板をエッチングすることで基板にパターンを形成する工程(B−5)と、
を有する、回路パターン形成方法。 - 請求項1〜9のいずれか1項に記載の化合物、又は、請求項10〜13のいずれか1項に記載の樹脂の精製方法であって、
水と任意に混和しない有機溶媒及び、前記化合物又は前記樹脂を含む溶液と、酸性の水溶液と、を接触させて抽出する工程を含む、精製方法。 - 前記酸性の水溶液が、塩酸、硫酸、硝酸及びリン酸からなる群より選ばれる1種以上の鉱酸水溶液である、又は、酢酸、プロピオン酸、蓚酸、マロン酸、コハク酸、フマル酸、マレイン酸、酒石酸、クエン酸、メタンスルホン酸、フェノールスルホン酸、p−トルエンスルホン酸及びトリフルオロ酢酸からなる群より選ばれる1種以上の有機酸水溶液である、請求項22に記載の精製方法。
- 前記水と任意に混和しない有機溶媒が、トルエン、2−ヘプタノン、シクロヘキサノン、シクロペンタノン、メチルイソブチルケトン、プロピレングリコールモノメチルエーテルアセテート又は酢酸エチルである、請求項22又は23に記載の精製方法。
- 前記溶液と酸性の水溶液とを接触させて抽出する工程の後、さらに水による抽出処理を行う工程を含む、請求項22〜24のいずれか1項に記載の精製方法。
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US11169441B2 (en) | 2017-07-14 | 2021-11-09 | Nissan Chemical Corporation | Composition for forming resist underlayer film, resist underlayer film, method for forming resist pattern and method for producing semiconductor device |
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