JPWO2016171179A1 - 樹脂組成物、それを用いた半導体素子の製造方法および半導体装置 - Google Patents
樹脂組成物、それを用いた半導体素子の製造方法および半導体装置 Download PDFInfo
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- JPWO2016171179A1 JPWO2016171179A1 JP2016535738A JP2016535738A JPWO2016171179A1 JP WO2016171179 A1 JPWO2016171179 A1 JP WO2016171179A1 JP 2016535738 A JP2016535738 A JP 2016535738A JP 2016535738 A JP2016535738 A JP 2016535738A JP WO2016171179 A1 JPWO2016171179 A1 JP WO2016171179A1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
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- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
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- NJWNEWQMQCGRDO-UHFFFAOYSA-N indium zinc Chemical compound [Zn].[In] NJWNEWQMQCGRDO-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
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- 239000003595 mist Substances 0.000 description 1
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- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LLYCMZGLHLKPPU-UHFFFAOYSA-N perbromic acid Chemical compound OBr(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-N selane Chemical compound [SeH2] SPVXKVOXSXTJOY-UHFFFAOYSA-N 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- IEPMHPLKKUKRSX-UHFFFAOYSA-J silicon(4+);tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Si+4] IEPMHPLKKUKRSX-UHFFFAOYSA-J 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
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- 229910000059 tellane Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 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
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- VEDJZFSRVVQBIL-UHFFFAOYSA-N trisilane Chemical compound [SiH3][SiH2][SiH3] VEDJZFSRVVQBIL-UHFFFAOYSA-N 0.000 description 1
- NXHILIPIEUBEPD-UHFFFAOYSA-H tungsten hexafluoride Chemical compound F[W](F)(F)(F)(F)F NXHILIPIEUBEPD-UHFFFAOYSA-H 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- IGELFKKMDLGCJO-UHFFFAOYSA-N xenon difluoride Chemical compound F[Xe]F IGELFKKMDLGCJO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of 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 alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
- C08L29/06—Copolymers of allyl alcohol
- C08L29/08—Copolymers of allyl alcohol with vinyl-aromatic monomers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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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
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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
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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
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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
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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
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- G03F7/40—Treatment after imagewise removal, e.g. baking
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- 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
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
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- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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Abstract
Description
本発明の樹脂組成物は、(A1)一般式(1)で表される構造単位を有するアルカリ可溶性樹脂を含む。
本発明の樹脂組成物は、(A1)の樹脂の反応性基と反応する置換基を有する、ポリイミド、ポリベンゾオキサゾール、ポリアミドイミド、それらの前駆体およびそれらの共重合体からなる群より選ばれるアルカリ可溶性樹脂(A2)を含む。
3−スルホン酸−4,4’−ジアミノジフェニルエーテルなどのスルホン酸含有ジアミン、ジメルカプトフェニレンジアミンなどのチオール基含有ジアミン;
3,4’−ジアミノジフェニルエーテル、4,4’−ジアミノジフェニルエーテル、3,4’−ジアミノジフェニルメタン、4,4’−ジアミノジフェニルメタン、3,4’−ジアミノジフェニルスルホン、4,4’−ジアミノジフェニルスルホン、3,4’−ジアミノジフェニルスルフィド、4,4’−ジアミノジフェニルスルフィド、1,4−ビス(4−アミノフェノキシ)ベンゼン、ベンジン、m−フェニレンジアミン、p−フェニレンジアミン、1,5−ナフタレンジアミン、2,6−ナフタレンジアミン、ビス(4−アミノフェノキシフェニル)スルホン、ビス(3−アミノフェノキシフェニル)スルホン、ビス(4−アミノフェノキシ)ビフェニル、ビス{4−(4−アミノフェノキシ)フェニル}エーテル、1,4−ビス(4−アミノフェノキシ)ベンゼン、2,2’−ジメチル−4,4’−ジアミノビフェニル、2,2’−ジエチル−4,4’−ジアミノビフェニル、3,3’−ジメチル−4,4’−ジアミノビフェニル、3,3’−ジエチル−4,4’−ジアミノビフェニル、2,2’,3,3’−テトラメチル−4,4’−ジアミノビフェニル、3,3’,4,4’−テトラメチル−4,4’−ジアミノビフェニル、2,2’−ビス(トリフルオロメチル)−4,4’−ジアミノビフェニルなどの芳香族ジアミンや、これらの芳香族環の水素原子の一部を、炭素数1〜10のアルキル基やフルオロアルキル基、ハロゲン原子などで置換した化合物;
シクロヘキシルジアミン、メチレンビスシクロヘキシルアミンなどの脂環式ジアミンなどを挙げることができる。
本発明の樹脂組成物においては、(A1)の樹脂100重量部に対して、(A2)の樹脂が310〜2000重量部である。(A2)の樹脂の含有量は、(A1)の樹脂100重量部に対して、350重量部以上であることがより好ましく、375重量部以上であることがさらに好ましく、400重量部以上であることが特に好ましい。また、(A2)の樹脂の含有量は、(A1)の樹脂100重量部に対して、1750重量部以下であることがより好ましく、1500重量部以下であることがさらに好ましく、1000重量部以下であることが特に好ましい。(A2)の樹脂の含有量をこの範囲とすることにより、高い解像度および耐熱性が得られ、さらに、レジスト剥離液への溶解性を備えることができる。
本発明の樹脂組成物は、(B)感光剤を含有する。(B)感光剤は光によって硬化するネガタイプでも、光によって可溶化するポジタイプでも良く、(b−1)重合性不飽和化合物および光重合開始剤、または、(b−2)キノンジアジド化合物等が好ましく用いられる。
本発明の樹脂組成物は必要に応じて、さらに(A1)の樹脂とは別に(d)熱架橋性化合物を含有してもよい。具体的には、アルコキシメチル基またはメチロール基を少なくとも2つ有する化合物が好ましい。これらの基を少なくとも2つ有することで、樹脂および同種分子と縮合反応して架橋構造体とすることができる。
また、必要に応じて、キュア後の収縮残膜率を小さくしない範囲でフェノール性水酸基を有する低分子化合物を含有してもよい。これにより、現像時間を短縮することができる。
エチ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エチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノ−n−プロピルエーテル、ジエチレングリコールモノ−n−ブチルエーテル、トリエチレングリコールモノメチルエーテル、トリ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、プロピレングリコールモノ−n−プロピルエーテル、プロピレングリコールモノ−n−ブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノ−n−プロピルエーテル、ジプロピレングリコールモノ−n−ブチルエーテル、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル、テトラヒドロフラン、ジオキサンなどのエーテル類;
アセトン、メチルエチルケトン、ジイソブチルケトン、シクロヘキサノン、2−ヘプタノン、3−ヘプタノン、ジアセトンアルコールなどのケトン類;
エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、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、乳酸エチルなどのエステル類;
2−ヒドロキシ−2−メチルプロピオン酸エチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エ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、エトキシ酢酸エチル、ヒドロキシ酢酸エチル、2−ヒドロキシ−3−メチルブタン酸メチル、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート、3−メチル−3−メトキシブチルプロピオネート、酢酸エチル、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、ぎ酸n−ペンチル、酢酸i−ペンチル、プロピオン酸n−ブチル、酪酸エチル、酪酸n−プロピル、酪酸i−プロピル、酪酸n−ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸n−プロピル、アセト酢酸メチル、アセト酢酸エチル、2−オキソブタン酸エチル等の他のエステル類;
トルエン、キシレンなどの芳香族炭化水素類;
N−メチルピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド等のアミド類;
などの溶剤を単独、または混合して使用することができる。これらの中でもガンマブチロラクトンは他の成分を良好に溶解させ平坦性の良い塗膜を形成させることができるため好ましい。
本発明の半導体素子の製造方法は、(1)基板上に本発明の樹脂組成物のパターンを形成する工程、(2)150℃以上で、(a)前記基板に不純物イオンをドーピングする工程、(b)前記基板をエッチングする工程、および(c)前記基板にドライ製膜する工程、からなる群より選ばれる1つ以上の処理を行う工程、ならびに(3)前記パターンを剥離する工程を有する半導体素子の製造方法である。
本発明の樹脂組成物から得られるパターンをイオン注入マスクとして、パターンが形成された基板にイオン注入することで、基板中にパターン状のイオン不純物領域を形成することができる。
本発明の樹脂組成物から得られるパターンをマスクとして、パターンが形成された基板をドライエッチングまたはウェットエッチングすることで、基板をパターン状に加工することができる。
ワニスを、8インチのシリコンウェハ上に塗布現像装置ACT―8(東京エレクトロン製)を用いてスピンコート法で塗布および120℃で3分間プリベークを行なった。露光機i線ステッパーNSR−2005i9C(ニコン製)を用いて露光した。露光後、ACT−8の現像装置を用いて、2.38重量%のテトラメチルアンモニウム水溶液(以下TMAH、多摩化学工業製)を用いてパドル法で現像液の吐出時間10秒、パドル時間40秒の現像を2回繰り返し、その後純水でリンス後、振り切り乾燥し、露光部が完全に溶解している時の最低露光量を感度とした。感度が500mJ/cm2以上であるものを不十分(×)、300mJ/cm2以上500mJ/cm2未満のものを良好(B)、300mJ/cm2未満のものをさらに良好(A)とした。
ワニスを、8インチのシリコンウェハ上に塗布現像装置ACT―8を用いてスピンコート法で塗布および120℃で3分間プリベークを行なった。露光機i線ステッパーNSR−2005i9C(ニコン製)にパターンの切られたレチクルをセットし、800mJ/cm2の露光量で露光した。露光後、ACT−8の現像装置を用いて、2.38重量%のTMAHを用いてパドル法で現像液の吐出時間10秒、パドル時間40秒の現像を2回繰り返し、その後純水でリンス後、振り切り乾燥し、樹脂膜パターンを得た。イナートオーブンCLH−21CD−S(光洋サーモシステム製)を用いて、窒素気流下において酸素濃度20ppm以下で毎分3.5℃の昇温速度で200℃まで昇温し、200℃で1時間加熱処理を行なった。温度が50℃以下になったところでウェハーを取り出し、パターンを顕微鏡で観察し、ラインアンドスペースが解像している最小寸法を解像度とした。10μm以上の解像度を不十分(C)、5μm以上10μm未満のものを良好(B)、5μm未満のものをさらに良好(A)とした。
(1)でパターン加工したシリコンウェハをイナートオーブンINH−21CDを用いて、窒素気流下において酸素濃度20ppm以下で毎分3.5℃の昇温速度で200℃まで昇温し、250℃で1時間加熱処理を行なった。温度が50℃以下になったところでウェハを取り出し樹脂被膜を作製した。得られた樹脂被膜を剥離液106(東京応化工業製)中に浸漬し、70℃で10分間処理した後、水洗した。ウェハ表面を光学顕微鏡で観察し、パターンが全く不溶だったものを不十分(C)、ウェハ表面に残渣が残るがパターンは溶解した場合を良好(B)、ウェハ表面に残渣なくパターンが溶解した場合をさらに良好(A)とした。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)、21.22g(0.05モル)と5−ナフトキノンジアジドスルホン酸クロリド(東洋合成(株)製、NAC−5)26.8g(0.1モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合したトリエチルアミン12.65gを、系内が35℃以上にならないように滴下した。滴下後40℃で2時間撹拌した。トリエチルアミン塩を濾過し、濾液を水に投入した。その後、析出した沈殿を濾過で集め、さらに1%塩酸水1Lで洗浄した。その後、さらに水2Lで2回洗浄した。この沈殿を真空乾燥機で乾燥し、下記式で表されるキノンジアジド化合物(感光剤B)を得た。
テトラヒドロフラン500ml、開始剤としてsec−ブチルリチウム0.01モルを加えた混合溶液に、p−t−ブトキシスチレンとスチレンをモル比3:1の割合で合計20gを添加し、3時間撹拌しながら重合させた。重合停止反応は反応溶液にメタノール0.1モルを添加して行った。 次にポリマーを精製するために反応混合物をメタノール中に注ぎ、沈降した重合体を乾燥させたところ白色重合体が得られた。更に、アセトン400mlに溶解し、60℃で少量の濃塩酸を加えて7時間撹拌後、水に注ぎ、ポリマーを沈澱させ、p−t−ブトキシスチレンを脱保護してp−ヒドロキシスチレンに変換し、洗浄乾燥したところ、精製されたp−ヒドロキシスチレンとスチレンの共重合体(以下(A0−1))が得られた。また、GPCによる分析により重量平均分子量(Mw)が3500(GPCポリスチレン換算)、分散度は(Mw/Mn)2.80であった。
前記合成例2のp−t−ブトキシスチレンの代わりに、m−t−ブトキシスチレンを使用する以外は同様に行った。得られたm−ヒドロキシスチレンとスチレンの共重合体(以下(A0−2))は、GPCによる分析により重量平均分子量(Mw)が5000(GPCポリスチレン換算)、分散度は(Mw/Mn)3.20であった。
ポリヒドロキシスチレン樹脂(A0−1)を、水酸化ナトリウム80g(2.0モル)を純水800gに溶解させた溶液に溶解させた。完全に溶解させた後、20〜25℃で36〜38重量%のホルマリン水溶液686gを2時間かけて滴下した。その後20〜25℃で17時間撹拌した。これに硫酸98gと水552gを加えて中和を行い、そのまま2日間放置した。放置後に溶液に生じた白色固体を水100mLで洗浄した。この白色固体を50℃で48時間真空乾燥した。
前記合成例5の(A0−1)の代わりに(A0−2)を用いる以外は同様の製法において合成を行った。得られたメチロール化したポリヒドロキシスチレン樹脂であるアルカリ可溶性樹脂(以下(A1−2))は、GPCによる分析により重量平均分子量(Mw)が7500(GPCポリスチレン換算)であり、メチロール化したヒドロキシスチレンは、ヒドロキシスチレン1モルあたり55モル%の導入率であった。
乾燥窒素気流下、2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(以下、BAHF)31.13g(0.085モル)、末端封止剤として、3−アミノフェノール(以下、MAP)3.27g(0.03モル)をN−メチルピロリドン(NMP)80gに溶解させた。ここに3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物(以下、ODPA)31.2g(0.1モル)をNMP20gとともに加えて、20℃で1時間反応させ、次いで50℃で4時間反応させた。その後、キシレンを15g添加し、水をキシレンとともに共沸しながら、150℃で5時間攪拌した。攪拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥し、フェノール性水酸基を有するアルカリ可溶性樹脂であるポリイミド樹脂(以下、(A2−1))を得た。樹脂(A2−1)の重量平均分子量は25000、イミド化率は92%だった。
乾燥窒素気流下、BAHF23.83g(0.065モル)、D−400(HUNTSMAN(株)製) 8.00g(0.02モル)、末端封止剤として、4−アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここにODPA31.2g(0.1モル)をNMP20gとともに加えて、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥しアルカリ可溶性ポリイミド樹脂(A2−2)の粉末を得た。樹脂(A2−2)の重量平均分子量は23000、イミド化率は90%だった。
乾燥窒素気流下、BAHF23.83g(0.065モル)、ED−600(HUNTSMAN(株)製) 12.00g(0.02モル)、末端封止剤として、4−アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここにODPA31.2g(0.1モル)をNMP20gとともに加えて、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥しアルカリ可溶性ポリイミド樹脂(A2−3)の粉末を得た。樹脂(A2−3)の重量平均分子量は26000、イミド化率は95%だった。
乾燥窒素気流下、BAHF23.83g(0.065モル)、ED−900(HUNTSMAN(株)製) 18.00g(0.02モル)、末端封止剤として、4−アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここにODPA31.2g(0.1モル)をNMP20gとともに加えて、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥しアルカリ可溶性ポリイミド樹脂(A2−4)の粉末を得た。樹脂(A2−4)の重量平均分子量は25000、イミド化率は89%だった。
乾燥窒素気流下、BAHF23.83g(0.065モル)、ED−900(HUNTSMAN(株)製) 18.00g(0.02モル)、末端封止剤として、4−アミノフェノール(東京化成工業(株)製)3.27g(0.03モル)をNMP80gに溶解させた。ここに4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸二無水物(6FDA)17.68g(0.04モル)とODPA18.72g(0.06モル)をNMP20gとともに加えて、60℃で1時間反応させ、次いで180℃で4時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥しアルカリ可溶性ポリイミド樹脂(A2−5)の粉末を得た。樹脂(A2−5)の重量平均分子量は28000、イミド化率は93%だった。
乾燥窒素気流下、DAE18.0g(0.09モル)、NMP80gに溶解させた。ここにODPA31.2g(0.1モル)をNMP20gとともに加えて、20℃で1時間反応させ、次いで50℃で4時間反応させた。さらにその後、180℃で5時間攪拌した。攪拌終了後、溶液を水3Lに投入して白色沈殿を得た。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で20時間乾燥し、(A1)の反応性基と反応する置換基を有さないポリイミド樹脂(以下、(A2−6))を得た。
以下の表1に示す重量比で、各成分を混合したのち、溶剤を加え、固形分濃度40%のワニスを調製し、これらの特性を上記評価方法により測定した。得られた結果を表2に示す。
実施例10のワニスを、8インチのシリコンウェハ上に形成した5μm厚みのアルミニウム膜に7μm厚で、塗布現像装置ACT―8を用いてスピンコート法で塗布および120℃で3分間プリベークを行なった。露光機i線ステッパーNSR−2005i9C(ニコン製)にパターンの切られたレチクルをセットし、500mJ/cm2の露光量で露光した。露光後、ACT−8の現像装置を用いて、2.38重量%のTMAHを用いてパドル法で現像液の吐出時間10秒、パドル時間40秒の現像を2回繰り返し、その後純水でリンス後、振り切り乾燥し、樹脂膜パターンを得た。イナートオーブンCLH−21CD−S(光洋サーモシステム製)を用いて、窒素気流下において酸素濃度20ppm以下で毎分3.5℃の昇温速度で200℃まで昇温し、200℃で1時間加熱処理を行なった。温度が50℃以下になったところでウェハを取り出した。その後、RIE−200iP(サムコ社製)0.5Pa、400W、Cl2/BCl3=10/45sccmの条件で、ドライエッチングを行い、その後、純水で5分洗浄した。その際、基板温度が210℃まで到達したが、樹脂膜に剥がれ、クラック、膨れなどは発生していなかった。その後、重量比でジメチルフルフォキシド/モノエタノールアミン=3/7の80℃の溶液に10分間処理を行い、樹脂膜パターンの溶解剥離を行った。その結果、5μm厚のアルミニウム膜において、3μmの微細な解像を確認した。
実施例16
実施例10のワニスを、4インチのSiCウェハ上に、3μm厚で、スピンコート法で塗布および120℃で3分間プリベークを行なった。露光機i線ステッパーNSR−2005i9C(ニコン製)にパターンの切られたレチクルをセットし、500mJ/cm2の露光量で露光した。露光後、自動現像装置を用いて、2.38重量%のTMAHを用いてパドル法で現像液の吐出時間10秒、パドル時間40秒の現像を2回繰り返し、その後純水でリンス後、振り切り乾燥し、樹脂膜パターンを得た。イナートオーブンCLH−21CD−S(光洋サーモシステム製)を用いて、窒素気流下において酸素濃度20ppm以下で毎分3.5℃の昇温速度で250℃まで昇温し、250℃で1時間加熱処理を行なった。温度が50℃以下になったところでウェハを取り出した。その後、イオン注入装置(日新イオン社製)でイオン注入を行った。イオン注入は、イオン注入温度:250℃、イオン注入エネルギー:300keV、イオンドーズ量:1×1013cm−2、イオン種:アルミ、電流値:500μAにて実施した。イオン注入後、樹脂膜に剥がれ、クラック、膨れなどは発生していなかった。その後、重量比でジメチルフルフォキシド/モノエタノールアミン=3/7の80℃の溶液に10分間処理を行い、樹脂膜パターンの溶解剥離を行った。その結果、2μmの解像度で、SiCにAlのイオン注入が形成できたことを確認できた。
実施例10のワニスを、4インチのSiウェハ上に、3μm厚で、スピンコート法で塗布および120℃で3分間プリベークを行なった。露光機i線ステッパーNSR−2005i9C(ニコン製)にパターンの切られたレチクルをセットし、500mJ/cm2の露光量で露光した。露光後、自動現像装置を用いて、2.38重量%のTMAHを用いてパドル法で現像液の吐出時間10秒、パドル時間40秒の現像を2回繰り返し、その後純水でリンス後、振り切り乾燥し、樹脂膜パターンを得た。イナートオーブンCLH−21CD−S(光洋サーモシステム製)を用いて、窒素気流下において酸素濃度20ppm以下で毎分3.5℃の昇温速度で250℃まで昇温し、250℃で1時間加熱処理を行なった。温度が50℃以下になったところでウェハを取り出した。その後、イオンミリング装置(JEOL製:IB−09020CP)にて、イオン加速電圧:4kV、イオンビーム径:500μm(半値幅)、ミリングスピード:100μm/Hでイオンミリングを行った。イオンミリング後、樹脂膜に剥がれ、クラック、膨れなどは発生していなかった。その後、重量比でジメチルフルフォキシド/モノエタノールアミン=3/7の80℃の溶液に10分間処理を行い、樹脂膜パターンの溶解剥離を行った。その結果、2μmの解像度で、Siウェハへの溝の形成を確認できた。
Claims (12)
- (A2)の樹脂が、ポリエチレンオキサイド構造および/またはポリプロピレンオキサイド構造を有する請求項1または2のいずれかに記載の樹脂組成物。
- さらに(d)熱架橋性化合物を含有する請求項1〜3のいずれかに記載の樹脂組成物。
- 250℃で1時間の熱処理後に、重量比でジメチルスルフォキシド/モノエタノールアミン=3/7の溶液に可溶である請求項1〜4のいずれかに記載の樹脂組成物。
- 請求項1〜5のいずれかに記載の樹脂組成物を含むフォトレジスト。
- (1)基板上に請求項1〜5のいずれかに記載の樹脂組成物のパターンを形成する工程、(2)150℃以上で、(a)前記基板に不純物イオンをドーピングする工程、(b)前記基板をエッチングする工程、および(c)前記基板にドライ製膜する工程、からなる群より選ばれる1つ以上の処理を行う工程、ならびに(3)前記パターンを剥離する工程を有する半導体素子の製造方法。
- 前記(a)の工程が、
(a−1)前記基板にイオン注入する工程、または
(a−2)前記パターン樹脂膜形成基板にドーパント暴露する工程
のいずれかである請求項7記載の半導体素子の製造方法。 - 前記(b)の工程が、
(b−1)前記基板をドライエッチングでパターン加工する工程、または
(b−2)前記基板をウェットエッチングでパターン加工する工程
のいずれかである請求項7記載の半導体素子の製造方法。 - 前記(c)の工程が、前記基板に金属膜をドライ製膜する工程である請求項7記載の半導体素子の製造方法。
- 前記基板が、ケイ素、二酸化ケイ素(SiO2)、窒化ケイ素(Si3N4)、炭化ケイ素(SiC)、窒化ガリウム(GaN)、リン化ガリウム(GaP)、ヒ化ガリウム(GaAs)、ヒ化ガリウムアルミニウム(GaAlAs)、ガリウムインジウム窒素ヒ素(GaInNAs)、窒化インジウム(InN)、リン化インジウム(InP)、酸化インジウムスズ(ITO)、酸化インジウム亜鉛(IZO)、ヒ化インジウムガリウム(InGaAs)、インジウムガリウムアルミニウムリン(InGaAlP)、酸化インジウムガリウム亜鉛(IGZO)、ダイヤモンド、サファイア(Al2O3)、酸化アルミニウム亜鉛(AZO)、窒化アルミニウム(AlN)、酸化亜鉛(ZnO)、セレン化亜鉛(ZnSe)、硫化カドミウム(CdS)及びテルル化カドミウム(CdTe)、アルミ(Al)、金(Au)からなる群より選ばれる一種以上を有する基板である、請求項7〜10のいずれか記載の半導体素子の製造方法。
- 請求項7〜11のいずれか記載の方法で得られた半導体素子を含む半導体装置。
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WO2017043375A1 (ja) * | 2015-09-08 | 2017-03-16 | 東レ株式会社 | 感光性樹脂組成物、感光性シート、半導体装置および半導体装置の製造方法 |
US10723856B2 (en) * | 2016-12-20 | 2020-07-28 | University Of South Carolina | Etchant for use in rapid formation of robust porous polymers |
JP6903916B2 (ja) * | 2017-01-12 | 2021-07-14 | 東レ株式会社 | 樹脂組成物 |
US11739215B2 (en) * | 2017-02-21 | 2023-08-29 | Zeon Corporation | Photosensitive resin composition |
JP7363030B2 (ja) * | 2018-01-17 | 2023-10-18 | 東レ株式会社 | 樹脂組成物、硬化膜、硬化膜のレリーフパターンの製造方法、電子部品、半導体装置、電子部品の製造方法、半導体装置の製造方法 |
JPWO2019146436A1 (ja) * | 2018-01-26 | 2021-01-14 | 日本ゼオン株式会社 | 感光性樹脂組成物及びレンズ |
US11824099B2 (en) * | 2020-06-15 | 2023-11-21 | Taiwan Semiconductor Manufacturing Co., Ltd. | Source/drains in semiconductor devices and methods of forming thereof |
KR20220080488A (ko) * | 2020-12-07 | 2022-06-14 | 주식회사 엘지화학 | 폴리이미드 수지, 포지티브형 감광성 수지 조성물, 절연막 및 반도체 장치 |
TWI833599B (zh) * | 2022-08-26 | 2024-02-21 | 日商德山股份有限公司 | 半導體用處理液及半導體元件之製造方法 |
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KR20170140186A (ko) | 2017-12-20 |
CN107429058A (zh) | 2017-12-01 |
SG11201708729TA (en) | 2017-11-29 |
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TW201700510A (zh) | 2017-01-01 |
EP3287495A4 (en) | 2018-10-17 |
CN107429058B (zh) | 2020-08-07 |
JP6702188B2 (ja) | 2020-05-27 |
EP3287495B1 (en) | 2020-06-24 |
WO2016171179A1 (ja) | 2016-10-27 |
US10451969B2 (en) | 2019-10-22 |
US20180164683A1 (en) | 2018-06-14 |
EP3287495A1 (en) | 2018-02-28 |
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