JP5620686B2 - 感光性樹脂組成物、硬化レリーフパターンの製造方法及び半導体装置 - Google Patents
感光性樹脂組成物、硬化レリーフパターンの製造方法及び半導体装置 Download PDFInfo
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- JP5620686B2 JP5620686B2 JP2010025778A JP2010025778A JP5620686B2 JP 5620686 B2 JP5620686 B2 JP 5620686B2 JP 2010025778 A JP2010025778 A JP 2010025778A JP 2010025778 A JP2010025778 A JP 2010025778A JP 5620686 B2 JP5620686 B2 JP 5620686B2
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- 239000002243 precursor Substances 0.000 claims description 29
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- 125000004185 ester group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- 238000001723 curing Methods 0.000 description 5
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 5
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- OBCUSTCTKLTMBX-VIFPVBQESA-N (2s)-2-acetyloxy-2-phenylacetic acid Chemical compound CC(=O)O[C@H](C(O)=O)C1=CC=CC=C1 OBCUSTCTKLTMBX-VIFPVBQESA-N 0.000 description 3
- PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
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- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- FJDLJSWDGIJLDC-UHFFFAOYSA-N sulfane;2,2,2-trifluoroacetic acid Chemical compound [SH3+].[O-]C(=O)C(F)(F)F FJDLJSWDGIJLDC-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 1
- BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 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
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- IYNZAVDBHAQODX-UHFFFAOYSA-N tert-butyl 4-(4-bromopyrazol-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1N=CC(Br)=C1 IYNZAVDBHAQODX-UHFFFAOYSA-N 0.000 description 1
- DLRDEMODNIPHMU-UHFFFAOYSA-N tert-butyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OC(C)(C)C)C=C1 DLRDEMODNIPHMU-UHFFFAOYSA-N 0.000 description 1
- QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-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
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 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
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 description 1
- MAZWDMBCPDUFDJ-VQHVLOKHSA-N traumatic acid Chemical compound OC(=O)CCCCCCCC\C=C\C(O)=O MAZWDMBCPDUFDJ-VQHVLOKHSA-N 0.000 description 1
- KNSPDNCKBBQYGB-UHFFFAOYSA-N tricyclo[5.2.1.02,6]decane-1,2-dicarbonyl chloride Chemical compound C12CCCC2(C(Cl)=O)C2(C(=O)Cl)CC1CC2 KNSPDNCKBBQYGB-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- YFNYCSJNUJQGNF-UHFFFAOYSA-N triethoxy(1-triethoxysilylethenyl)silane Chemical group CCO[Si](OCC)(OCC)C(=C)[Si](OCC)(OCC)OCC YFNYCSJNUJQGNF-UHFFFAOYSA-N 0.000 description 1
- FOQJQXVUMYLJSU-UHFFFAOYSA-N triethoxy(1-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)[Si](OCC)(OCC)OCC FOQJQXVUMYLJSU-UHFFFAOYSA-N 0.000 description 1
- VJDYPOQWHRJALO-UHFFFAOYSA-N triethoxy(1-triethoxysilylocta-1,3-dienyl)silane Chemical compound CCCCC=CC=C([Si](OCC)(OCC)OCC)[Si](OCC)(OCC)OCC VJDYPOQWHRJALO-UHFFFAOYSA-N 0.000 description 1
- KMLVDTJUQJXRRH-UHFFFAOYSA-N triethoxy(2-pyridin-2-ylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=N1 KMLVDTJUQJXRRH-UHFFFAOYSA-N 0.000 description 1
- OSAJVUUALHWJEM-UHFFFAOYSA-N triethoxy(8-triethoxysilyloctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCCC[Si](OCC)(OCC)OCC OSAJVUUALHWJEM-UHFFFAOYSA-N 0.000 description 1
- NIINUVYELHEORX-UHFFFAOYSA-N triethoxy(triethoxysilylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)C[Si](OCC)(OCC)OCC NIINUVYELHEORX-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- ULAQISQDFQAUCH-UHFFFAOYSA-N trifluoromethanesulfonic acid hydroiodide Chemical compound I.OS(=O)(=O)C(F)(F)F ULAQISQDFQAUCH-UHFFFAOYSA-N 0.000 description 1
- RIUWBIIVUYSTCN-UHFFFAOYSA-N trilithium borate Chemical compound [Li+].[Li+].[Li+].[O-]B([O-])[O-] RIUWBIIVUYSTCN-UHFFFAOYSA-N 0.000 description 1
- JBYXACURRYATNJ-UHFFFAOYSA-N trimethoxy(1-trimethoxysilylhexyl)silane Chemical compound CCCCCC([Si](OC)(OC)OC)[Si](OC)(OC)OC JBYXACURRYATNJ-UHFFFAOYSA-N 0.000 description 1
- XVZMLSWFBPLMEA-UHFFFAOYSA-N trimethoxy(2-pyridin-2-ylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=N1 XVZMLSWFBPLMEA-UHFFFAOYSA-N 0.000 description 1
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-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
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 description 1
- VOSUIKFOFHZNED-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,3,5-tricarboxylate Chemical compound C=CCOC(=O)C1=CC(C(=O)OCC=C)=CC(C(=O)OCC=C)=C1 VOSUIKFOFHZNED-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 238000011077 uniformity evaluation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L21/04—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
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Health & Medical Sciences (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
Description
下記一般式(1):
で表される化合物、及び下記一般式(2):
で表される化合物からなる群より選ばれる少なくとも1種の化合物を含む溶剤(B)10〜1000質量部、並びに
感光剤(C)0.1〜100質量部、
を含有する、感光性樹脂組成物。
[2] 上記アルカリ可溶性樹脂(A)が、下記一般式(3):
で表される構造及び/又は下記一般式(4):
で表される構造を有する樹脂である、上記[1]に記載の樹脂組成物。
[3] 架橋剤(D)1〜100質量部をさらに含有する、上記[1]又は[2]に記載の感光性樹脂組成物。
[4] 上記架橋剤(D)が、メチロール基及び/又はアルコキシメチル基を有する芳香族化合物、並びにN位がメチロール基及び/又はアルコキシメチル基で置換された化合物からなる群から選ばれる少なくとも1種の化合物である、上記[3]に記載の感光性樹脂組成物。
[5] 上記一般式(1)及び(2)中のR1及びR2が、それぞれ独立に、水酸基及び/又はエステル基を有する炭化水素基である、上記[1]〜[4]のいずれかに記載の感光性樹脂組成物。
[6] (1)上記[1]〜[5]のいずれかに記載の感光性樹脂組成物を基板上に塗布することによって感光性樹脂層を該基板上に形成する工程、
(2)該感光性樹脂層を露光する工程、
(3)該露光後の感光性樹脂層を現像することによってレリーフパターンを形成する工程、及び
(4)得られたレリーフパターンを加熱処理することによって硬化レリーフパターンを形成する工程、
を含む、硬化レリーフパターンの製造方法。
[7] 上記[6]に記載の硬化レリーフパターンの製造方法により得られる硬化レリーフパターンからなる樹脂膜を有する、半導体装置。
本発明は、ポリイミド構造、ポリベンゾオキサゾール構造、ポリイミド前駆体構造、及びポリベンゾオキサゾール前駆体構造からなる群から選ばれる1種以上の構造を有する樹脂を含むアルカリ可溶性樹脂(A)100質量部、
下記一般式(1):
で表される化合物、及び下記一般式(2):
で表される化合物からなる群より選ばれる少なくとも1種の化合物を含む溶剤(B)10〜1000質量部、並びに
感光剤(C)0.1〜100質量部、
を含有する、感光性樹脂組成物を提供する。本発明の感光性樹脂組成物を構成する各成分について、以下具体的に説明する。なお本明細書を通じ、一般式において同一符号で表されている構造は、分子中に複数存在する場合互いに同一でも異なっていてもよい。
アルカリ可溶性樹脂(A)は本発明の感光性樹脂組成物のベースポリマーであり、ポリイミド構造、ポリベンゾオキサゾール構造、ポリイミド前駆体構造、及びポリベンゾオキサゾール前駆体構造からなる群から選ばれる1種以上の構造を有する樹脂を含む。樹脂中に上記構造の複数の構造を有していても構わない。
で表される構造(ポリイミド構造)を有する樹脂であることが好ましい。
で表される構造(以下、「PBO前駆体」、「ヒドロキシポリアミド」とも言う)、及び
下記一般式(6):
で表される構造(以下、「ポリアミック酸」「ポリアミド酸」とも言う)からなる群より選ばれる少なくとも1種の構造を含むことが好ましい。
のように、原料のX2(NH2)2(OH)2の構造を有するジアミノジヒドロキシ化合物(好ましくはビスアミノフェノール)に由来する構造の一部が、X5(NH2)2の構造を有するジアミン(ヒドロキシ基は有さない)に由来する構造に置き換わっている重合体を用いてもよく、上記一般式(4)に関連し、下記一般式(8):
において、原料のX3(NH2)2(OH)2の構造を有するジアミノジヒドロキシ化合物(好ましくはビスアミノフェノール)に由来する構造の一部が、X6(NH2)2(OH)の構造を有するジアミノヒドロキシ化合物(好ましくはアミノフェノール)に由来する構造(a2=1のとき)及び/又はX6(NH2)2の構造を有するジアミンに由来する構造(a2=0のとき)に置き換わっている重合体を用いてもよい。
で表されるジアミンが挙げられる。
で表されるジアミンを得る方法もある。なお、上記Y7は後述する有機基であることが好ましい。
例えば、Y2、Y5及びY7としてそれぞれ下記一般式(12)及び(13):
から選ばれた芳香族基又は脂肪族基を含むジカルボン酸が挙げられる。
で表される化合物が挙げられ、A2の好ましい具体例としては、下記式(15):
で表される化合物が挙げられる。
で表される構造を有するものが挙げられる。
で表される化合物が挙げられ、A4としては、具体的には下記式(20):
本発明の感光性樹脂組成物が含有する溶剤(B)は、下記一般式(1):
で表される化合物、及び下記一般式(2):
で表される化合物からなる群より選ばれる少なくとも1種の化合物を含む。
本発明の感光性樹脂組成物が含有する感光剤(C)としては、感光性樹脂組成物をポジ型又はネガ型として目的用途に適用することを可能にする化合物を利用できる。感光性樹脂組成物をポジ型として使用する場合には、感光剤(C)としてはナフトキノンジアジド化合物を用いることが好ましい。
具体的な化合物としては、特開2001−092138号公報の[化23]〜[化28]に記載される化合物が挙げられる。その中でも以下のポリヒドロキシ化合物のNQD化物が、感度が高く、ポジ型感光性樹脂組成物中での析出性が低いことから好ましい:
具体的な化合物としては、特開2003−131368号公報の[化22]〜[化28]に記載される化合物が挙げられる。その中でも、以下のポリヒドロキシ化合物のNQD化物が、感度が高く、ポジ型感光性樹脂組成物中での析出性が低いことから好ましい。
具体的な化合物としては、特開2004−109849号公報の[化17]〜[化22]に記載されるポリヒドロキシ化合物のNQD化物が挙げられる。その中でも、以下のポリヒドロキシ化合物のNQD化物が、感度が高く、ポジ型感光性樹脂組成物中での析出性が低いことから好ましい。
具体的な化合物としては、特開2005−008626号公報の[化15]、及び[化16]に記載されるポリヒドロキシ化合物のNQD化物が挙げられる。その中でも、以下のポリヒドロキシ化合物のNQD化物が、感度が高く、ポジ型感光性樹脂組成物中での析出性が低いことから好ましい。
トリス(2,4,6−トリクロロメチル)−s−トリアジン、2−フェニル−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(3−クロロフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(2−クロロフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(4−メトキシフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(3−メトキシフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(2−メトキシフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(4−メチルチオフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(3−メチルチオフェニル)ビス(4,6−トリクロロメチル−s−トリアジン、2−(2−メチルチオフェニル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(4−メトキシナフチル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(3−メトキシナフチル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(2−メトキシナフチル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(3,4,5−トリメトキシ−β−スチリル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(4−メチルチオ−β―スチリル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(3−メチルチオ−β―スチリル)−ビス(4,6−トリクロロメチル)−s−トリアジン、2−(2−メチルチオ−β−スチリル)−ビス(4,6−トリクロロメチル)−s−トリアジン等。
ジフェニルヨードニウムテトラフルオロボレート、ジフェニルヨードニウムテトラフルオロホスフェート、ジフェニルヨードニウムテトラフルオロアルセネート、ジフェニルヨードニウムトリフルオロメタンスルホナート、ジフェニルヨードニウムトリフルオロアセテート、ジフェニルヨードニウム−p−トルエンスルホナート、4−メトキシフェニルフェニルヨードニウムテトラフルオロボレート、4−メトキシフェニルフェニルヨードニウムヘキサフルオロホスホネート、4−メトキシフェニルフェニルヨードニウムヘキサフルオロアルセネート、4−メトキシフェニルフェニルヨードニウムトリフルオロメタンスホナート、4−メトキシフェニルフェニルヨードニウムトリフルオロアセテート、4−メトキシフェニルフェニルヨードニウム−p−トルエンスルホナート、ビス(4−ter−ブチルフェニル)ヨードニウムテトラフルオロボレート、ビス(4−ter−ブチルフェニル)ヨードニウムヘキサフルオロアルセネート、ビス(4−ter−ブチルフェニル)ヨードニウムトリフルオロメタンスルホナート、ビス(4−ter−ブチルフェニル)ヨードニウムトリフルオロアセテート、ビス(4−ter−ブチルフェニル)ヨードニウム−p−トルエンスルホナート等。
トリフェニルスルホニウムテトラフルオロボレート、トリフェニルスルホニウムヘキサフルオロホスホネート、トリフェニルスルホニウムヘキサフルオロアルセネート、トリフェニルスルホニウムメタンスルホナート、トリフェニルスルホニウムトリフルオロアセテート、トリフェニルスルホニウム−p−トルエンスルホナート、4−メトキシフェニルジフェニルスルホニウムテトラフルオロボレート、4−メトキシフェニルジフェニルスルホニウムヘキサフルオロホスホネート、4−メトキシフェニルジフェニルスルホニウムヘキサフルオロアルセネート、4−メトキシフェニルジフェニルスルホニウムメタンスルホナート、4−メトキシフェニルジフェニルスルホニウムトリフルオロアセテート、4−メトキシフェニルジフェニルスルホニウム−p−トルエンスルホナート、4−フェニルチオフェニルジフェニルテトラフルオロボレート、4−フェニルチオフェニルジフェニルヘキサフルオロホスホネート、4−フェニルチオフェニルジフェニルヘキサフルオロアルセネート、4−フェニルチオフェニルジフェニルトリフルオロメタンスルホナート、4−フェニルチオフェニルジフェニルトリフルオロアセテート、4−フェニルチオフェニルジフェニルーp−トルエンスルホナート等。
ジアゾケトン化合物として、例えば、1,3−ジケト−2−ジアゾ化合物、ジアゾベンゾキノン化合物、ジアゾナフトキノン化合物等を挙げることができ、具体例としてはフェノール類の1,2−ナフトキノンジアジド−4−スルホン酸エステル化合物を挙げることができる。
スルホン化合物として、例えば、β−ケトスルホン化合物、β−スルホニルスルホン化合物及びこれらの化合物のα−ジアゾ化合物を挙げることができ、具体例として、4−トリスフェナシルスルホン、メシチルフェナシルスルホン、ビス(フェナシルスルホニル)メタン等を挙げることができる。
スルホン酸化合物として、例えば、アルキルスルホン酸エステル類、ハロアルキルスルホン酸エステル類、アリールスルホン酸エステル類、イミノスルホネート類等を挙げることができる。好ましい具体例としては、ベンゾイントシレート、ピロガロールトリストリフルオロメタンスルホネート、o−ニトロベンジルトリフルオロメタンスルホネート、o−ニトロベンジルp−トルエンスルホネート等を挙げることができる。
スルホンイミド化合物の具体例として、例えば、N−(トリフルオロメチルスルホニルオキシ)スクシンイミド、N−(トリフルオロメチルスルホニルオキシ)フタルイミド、N−(トリフルオロメチルスルホニルオキシ)ジフェニルマレイミド、N−(トリフルオロメチルスルホニルオキシ)ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド、N−(トリフルオロメチルスルホニルオキシ)ナフチルイミド等を挙げることができる。
2−[2−(4−メチルフェニルスルホニルオキシイミノ)]−2,3−ジヒドロチオフェン−3−イリデン]−2−(2−メチルフェニル)アセトニトリル(チバスペシャルティケミカルズ社商品名「イルガキュアPAG121」)、[2−(プロピルスルホニルオキシイミノ)−2,3−ジヒドロチオフェン−3−イリデン]−2−(2−メチルフェニル)アセトニトリル(チバスペシャルティケミカルズ社商品名「イルガキュアPAG103」)、[2−(n−オクタンスルホニルオキシイミノ)−2,3−ジヒドロチオフェン−3−イリデン]−2−(2−メチルフェニル)アセトニトリル(チバスペシャルティケミカルズ社商品名「イルガキュアPAG108」)、α−(n−オクタンスルフォニルオキシイミノ)−4−メトキシベンジルシアニド(チバスペシャルティケミカルズ社商品名「CGI725」)等を挙げることができる。
ジアゾメタン化合物の具体例として、例えば、ビス(トリフルオロメチルスルホニル)ジアゾメタン、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(フェニルスルホニル)ジアゾメタン等を挙げることができる。
とりわけ、感度の観点から、上記オキシムエステル化合物群が特に好ましい。
本発明においては、感光性樹脂組成物を、ポジ型で利用する場合には、熱硬化後の膜(感光性樹脂層)の耐薬品性を高める目的で、ネガ型で利用する場合には、熱硬化後の膜の耐薬品性を高める目的とともにパターン形成の目的で、それぞれ、架橋剤(D)を好ましく利用することができる。
で表される構造を有するものが好ましい。
で表される構造を有するものが好ましい。
本発明の感光性樹脂組成物は、必要に応じて、その他の添加剤(E)を含有できる。その他の添加剤(E)としては、ア)モノカルボン酸化合物、イ)ヒドロキシル基含有化合物、ウ)フェノール化合物、エ)染料、オ)界面活性剤、カ)シリコンウエハーとの接着性を高めるための接着助剤、キ)増感剤、ク)重合禁止剤、及びケ)熱酸発生剤、からなる群から選択される少なくとも1種を挙げることができる。
モノカルボン酸化合物は、炭素原子数が7〜30であることが好ましい。モノカルボン酸化合物としては、イソノナン酸、3−シクロヘキセン−1−カルボン酸、1−シクロヘキセン−3−カルボン酸、ラウリン酸、o−トリル酢酸、m−トリル酢酸、p−トリル酢酸、o−トルイル酸、m−トルイル酸、p−トルイル酸、o−アニス酸、m−アニス酸、p−アニス酸、3−フェニル乳酸、4−ヒドロキシフェニル乳酸、4−ヒドロキシマンデル酸、3,4−ジヒドロキシマンデル酸、4−ヒドロキシ−3−メトキシマンデル酸、アセチルマンデル酸、α−メトキシフェニル酢酸等が挙げられる。これらの中でも、1−シクロヘキセン−3−カルボン酸、m−トリル酢酸、m−トルイル酸、m−アニス酸、アセチルマンデル酸、及びα−メトキシフェニル酢酸が好ましく、基板との密着性の観点から、m−トリル酢酸、m−トルイル酸、m−アニス酸、アセチルマンデル酸、及びα−メトキシフェニル酢酸が好ましい。これらのモノカルボン酸化合物は単独で使用しても2種以上混合して使用してもよい。
ヒドロキシル基含有化合物は、炭素原子数が4〜14であることが好ましい。ヒドロキシル基含有化合物として、具体的には、シクロプロピルカルビノール、2−シクロヘキセン−1−オール、シクロヘキサンメタノール、4−メチル−1−シクロヘキサンメタノール、3,4−ジメチルシクロヘキサノール、4−エチルシクロヘキサノール、4−t−ブチロシクロヘキサノール、シクロヘキサンエタノール、3−シクロヘキシル−1−プロパノール、1−シクロヘキシル−1−ペンタノール、3,3,5−トリメチルシクロヘキサノール、ノルボルナン−2−メタノール、シクロオクタノール、2,3,4−トリメチル−3−ペンタノール、2,4−ヘキサジエン−1−オール、cis−2−ヘキセン−1−オール、trans−2−ヘプテン−1−オール、cis−4−ヘプテン−1−オール、cis−3−オクテン−1−オール、4−エチル−1−オクチン−3−オール、2,7−オクタジエノール、3,6−ジメチル−1−ヘプチン−3−オール、3−エチル−2−メチル−3−ペンタノール、2−エチル−1−ヘキサノール、2,3−ジメチル−2−ヘキサノール、2,5−ジメチル−2−ヘキサノール、trans,cis−2,6−ノナジエン−1−オール、1−ノネン−3−オール、cis−2−ブテン−1,4−ジオール、2,2−ジエチル−1,3−プロパンジオール、2,4−ジエチル−1,5−ペンタンジオール、1,5−ヘキサジエン−3,4−ジオール、2,5−ジメチル−3−ヘキシン−2,5−ジオール、2,4,7,9−テトラメチル−5−デシン−4,7−ジオール、2,2,4,4−テトラメチル−1,3−シクロブタンジオール、1,2−シクロヘキサンジオール、trans−p−メンタン−3,8−ジオール、2,4−ジメトキシベンジルアルコール、ブチロイン等が挙げられる。
フェノール化合物としては、前記のナフトキノンジアジド化合物に使用しているバラスト剤、並びにパラクミルフェノール、ビスフェノール類、レゾルシノール類、更に、MtrisPC、MtetraPC等の直鎖状フェノール化合物(本州化学工業社製:商品名)、TrisP−HAP、TrisP−PHBA、TrisP−PA等の非直鎖状フェノール化合物(本州化学工業社製:商品名)、ジフェニルメタンのフェニル基の水素原子2〜5個を水酸基に置換した化合物、2,2−ジフェニルプロパンのフェニル基の水素原子1〜5個を水酸基に置換した化合物、等が挙げられる。該フェノール化合物の配合により、現像時のレリーフパターンの密着性を向上させ残渣の発生をおさえることができる。なお、バラスト剤とは、フェノール性水素原子の一部がナフトキノンジアジドスルホン酸エステル化されたフェノール化合物である前述の感光性ジアゾキノン化合物の原料として使用されているフェノール化合物である。
染料としては、例えば、メチルバイオレット、クリスタルバイオレット、マラカイトグリーン等が挙げられる。染料を配合する場合の配合量は、アルカリ可溶性樹脂(A)100質量部に対し、0.1〜10質量部が好ましい。該配合量が0.1質量部以上である場合、パターン形状が良好であり、10質量部以下である場合熱硬化後の膜の耐熱性が良好である。
界面活性剤としては、ポリプロピレングリコール、ポリオキシエチレンラウリルエーテル等のポリグリコール類、及びその誘導体からなる非イオン系界面活性剤が挙げられる。また、フロラード(登録商標、住友3M社製:商品名)、メガファック(登録商標、大日本インキ化学工業社製:商品名)、及びルミフロン(登録商標、旭硝子社製:商品名)等のフッ素系界面活性剤が挙げられる。さらに、KP341(信越化学工業社製:商品名)、DBE(チッソ社製:商品名)、及びグラノール(共栄社化学社製:商品名)等の有機シロキサン界面活性剤が挙げられる。界面活性剤の配合により、感光性樹脂組成物塗布時のウエハーエッジでの塗膜のハジキをより発生しにくくすることができる。
接着助剤としては、アルキルイミダゾリン、酪酸、アルキル酸、ポリヒドロキシスチレン、ポリビニルメチルエーテル、t−ブチルノボラック、エポキシポリマー、及びエポキシシラン等の各種シランカップリング剤が挙げられる。
本発明の感光性樹脂組成物には、必要に応じ、光感度向上のための増感剤を配合することができる。このような増感剤としては、例えば、ミヒラーズケトン、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、2,5−ビス(4’−ジエチルアミノベンジリデン)シクロペンタノン、2,6−ビス(4’−ジエチルアミノベンジリデン)シクロヘキサノン、2,6−ビス(4’−ジメチルアミノベンジリデン)−4−メチルシクロヘキサノン、2,6−ビス(4’−ジエチルアミノベンジリデン)−4−メチルシクロヘキサノン、4,4’−ビス(ジメチルアミノ)カルコン、4,4’−ビス(ジエチルアミノ)カルコン、2−(4’−ジメチルアミノシンナミリデン)インダノン、2−(4’−ジメチルアミノベンジリデン)インダノン、2−(p−4’−ジメチルアミノビフェニル)ベンゾチアゾール、1,3−ビス(4−ジメチルアミノベンジリデン)アセトン、1,3−ビス(4−ジエチルアミノベンジリデン)アセトン、3,3’−カルボニル−ビス(7−ジエチルアミノクマリン)、3−アセチル−7−ジメチルアミノクマリン、3−エトキシカルボニル−7−ジメチルアミノクマリン、3−ベンジロキシカルボニル−7−ジメチルアミノクマリン、3−メトキシカルボニル−7−ジエチルアミノクマリン、3−エトキシカルボニル−7−ジエチルアミノクマリン、N−フェニル−N−エチルエタノールアミン、N−フェニルジエタノールアミン、N−p−トリルジエタノールアミン、N−フェニルエタノールアミン、N,N−ビス(2−ヒドロキシエチル)アニリン、4−モルホリノベンゾフェノン、4−ジメチルアミノ安息香酸イソアミル、4−ジエチルアミノ安息香酸イソアミル、ベンズトリアゾール、2−メルカプトベンズイミダゾール、1−フェニル−5−メルカプト−1,2,3,4−テトラゾール、1−シクロヘキシル−5−メルカプト−1,2,3,4−テトラゾール、1−(tert−ブチル)−5−メルカプト−1,2,3,4−テトラゾール、2−メルカプトベンゾチアゾール、2−(p−ジメチルアミノスチリル)ベンズオキサゾール、2−(p−ジメチルアミノスチリル)ベンズチアゾール、2−(p−ジメチルアミノスチリル)ナフト(1,2−p)チアゾール、2−(p−ジメチルアミノベンゾイル)スチレン等が挙げられる。
本発明の感光性樹脂組成物には、必要に応じ、溶液状態での保存時の感光性樹脂組成物の粘度及び光感度の安定性を向上させるために重合禁止剤を配合することができる。
熱酸発生剤は、熱により架橋剤の反応を促進させる化合物であり、酸が発生する温度としては、150〜350℃が好ましい。
次に、硬化レリーフパターンの製造方法について説明する。本発明は、(1)上述した本発明の感光性樹脂組成物を基板上に塗布することによって感光性樹脂層を該基板上に形成する工程、(2)該感光性樹脂層を露光する工程、(3)該露光後の感光性樹脂層を現像することによってレリーフパターンを形成する工程、及び(4)得られたレリーフパターンを加熱処理することによって硬化レリーフパターンを形成する工程、を含む、硬化レリーフパターンの製造方法をも提供する。該製造方法の各工程の典型的な態様について以下に詳述する。
本工程では、本発明の感光性樹脂組成物を、例えばシリコンウエハー、セラミック基板、アルミ基板等の基板に、スピンコーターを用いた回転塗布、又はダイコーター若しくはロールコーター等のコータ−により塗布する。又は、インクジェットノズル若しくはディスペンサーを用いて、基板上の所定の場所に感光性樹脂組成物を塗布することも可能である。これを例えばオーブン又はホットプレートを用いて例えば50〜140℃、好ましくは100〜140℃に加熱して乾燥させ溶剤を除去する(以下、「ソフトベーク」、又は「プリベーク」ともいう。)。以上により基板上に感光性樹脂層を形成できる。
続いて、本工程では、感光性樹脂層を活性光線により露光する。具体的には、コンタクトアライナー又はステッパーを用いて化学線による露光を行うか、光線、電子線又はイオン線を直接照射する。活性光線としては、例えばg線、h線、i線、又はKrFレーザーを用いることもできる。ここで、ネガ型感光性樹脂組成物を用いる場合は、露光の後に、加熱処理(露光後ベーキング(PEB))を行う。このPEB工程は、感光性樹脂組成物の感度を増感するための処理であり、本発明の作用効果を良好に得るためには通常必要である。PEB温度は、感度及び得られるパターン形状等を考慮すると、好ましくは80〜160℃、より好ましくは90〜150℃である。
本工程においては、ポジ型感光性樹脂組成物を用いる場合は、露光部(活性光線の直接照射の場合には照射部)を現像液で溶解除去し、好ましくは、引き続きリンス液によるリンスを行うことで所望のレリーフパターンを得る。ネガ型感光性樹脂組成物を用いる場合は、同様の方法で、未露光部を現像液で溶解除去する。現像方法としてはスプレー、パドル、ディップ、又は超音波等の方式が可能である。リンス液としては蒸留水、又は脱イオン水等が使用できる。
本工程では、得られたレリーフパターンを加熱処理(キュア)することにより、アルカリ可溶性樹脂(A)がPBO前駆体構造を有する場合にはポリベンゾオキサゾール構造を有する樹脂、ポリイミド前駆体構造を有する場合にはポリイミド構造を有する樹脂、である耐熱性の硬化レリーフパターンを形成できる。加熱装置としては、オーブン炉、ホットプレート、縦型炉、ベルトコンベアー炉、圧力オーブン等を使用する事ができ、加熱方法としては、熱風、赤外線、又は電磁誘導による加熱等が推奨される。加熱温度は200〜450℃が好ましく、250〜400℃がさらに好ましい。加熱時間は15分〜8時間が好ましく、1時間〜4時間がさらに好ましい。また加熱処理時の雰囲気は窒素、アルゴン等の不活性ガス中が好ましい。
以上のようにして硬化レリーフパターンを製造できる。
本発明は、上述した本発明の硬化レリーフパターンの製造方法により得られる硬化レリーフパターンからなる樹脂膜を有する、半導体装置をも提供する。本発明の半導体装置は、上述の硬化レリーフパターンからなる樹脂膜を、表面保護膜、層間絶縁膜、再配線用絶縁膜、フリップチップ装置用保護膜、バンプ構造を有する装置の保護膜等として有する。本発明の半導体装置は、上述の硬化レリーフパターンの製造方法を公知の半導体装置の製造方法と組み合わせることで製造することができる。
[製造例1]
容量2リットルのセパラブルフラスコ中で、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179.5g(0.49mol)、ピリジン71.2g(0.9mol)、DMAc650gを室温(25℃)で混合攪拌し、ジアミンを溶解させた。これに、別途DMDG(ジエチレングリコールジメチルエーテル)88g中に5−ノルボルネン−2,3−ジカルボン酸無水物13.1g(0.08mol)を溶解させたものを、滴下ロートより滴下した。滴下に要した時間は20分、反応液温は最大で28℃であった。
カラム:昭和電工社製 商標名 Shodex KF807/806M/806M/802.5
容離液:テトラヒドロフラン 40℃
流速 :1.0ml/分
検出器:昭和電工製 商標名 Shodex RI RI−101
容量2リットルのセパラブルフラスコ中で、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190.5g(0.52mol)、ピリジン71.2g(0.9mol)、DMAc760gを室温(25℃)で混合攪拌し、ジアミンを溶解させた。
カラム:昭和電工社製 商標名 Shodex KF807/806M/806M/802.5
容離液:テトラヒドロフラン 40℃
流速 :1.0ml/分
検出器:昭和電工製 商標名 Shodex RI RI−101
容量1リットルのセパラブルフラスコ中で、(4,4’−(1−メチルエチリデン)ビス(2−アミノフェノール)69.2g(0.268mol)、ピリジン12.7g(0.16mol)、NMP276gを室温(25℃)で混合攪拌し、ジアミンを溶解させた。
カラム:昭和電工社製 商標名 Shodex 805M/806M直列
容離液:N−メチルピロリドン 40℃
流速 :1.0ml/分
検出器:日本分光社製 商標名 RI−930
容量2リットルのセパラブルフラスコ中で、3,3−[1,3−フェニレンビス(オキシ)]ジアニリン58.5g(0.20mol)、GBL90.0gを室温(25℃)で混合攪拌し、ジアミンを溶解させた。氷浴により2℃に冷却し、5−ノルボルネン−2,3−ジカルボン酸無水物10.9g(0.067mol)をGBL25.0gにて溶解させたものを滴下した。滴下の後に室温まで昇温し、1時間攪拌した。再び氷浴により、2℃に冷却し、オキシジフタル酸二無水物51.7g(0.17mol)を投入した。反応液温は、18℃まで上昇した。氷浴での冷却を継続し、5℃に達したところで冷却を停止し、室温で一晩攪拌した。その後、70℃で2時間攪拌し、ポリアミック酸の40質量%GBL溶液(P−4)を得た。
カラム:昭和電工社製 商標名 Shodex KD806M/806M
容離液:N−メチルピロリドン 40℃
流速 :1.0ml/分
検出器:日本分光製 RI−930
ディーンスタークトラップ付き冷却管を取り付けた容量1リットルのセパラブル4つ口フラスコに、窒素ガスを通じながら、2,2−ビス(3−アミノ−4−ヒドロキシフェニル)プロパン72.28g(0.280mol)、5−(2,5−ジオキソテトラヒドロ−3−フリル)−3−メチル−3−シクロヘキセン−1,2ジカルボン酸無水物を70.29g(0.266mol)、γ−ブチロラクトン254.6g、トルエン60gを加えて、室温で4時間攪拌後、5−ノルボルネン−2、3−ジカルボン酸無水物4.6g(0.028mol)を加えて、窒素ガスを通じながら50℃で8時間加熱攪拌した。その後、180℃に加温し、2時間加熱攪拌した。反応中トルエン、水の留出分を除去した。イミド化反応終了後、室温に戻した。
カラム:昭和電工社製 商標名 Shodex KD−806M/806M
容離液:N−メチルピロリドン 40℃
流速 :1.0ml/分
検出器:日本分光社製 商標名 RI−930
(実施例1〜18、比較例1〜5)
上記製造例1〜5にて得られたアルカリ可溶性樹脂(A)としての(P−1)〜(P−5)、並びに、アルカリ可溶性樹脂(A)以外の樹脂であるノボラック樹脂(旭有機材社製 EP4080G)(P−6)、感光剤(C)としての下記化合物(A−1)〜(A−2):
上記感光性樹脂組成物を東京エレクトロン社製スピンコーター(CLEANTRACK MK−8)にて、6インチシリコンウエハーにスピン塗布し、表2に示す条件で、ホットプレートにてプリベークを行い、10μm厚の塗膜を形成した。ウェハー面内につき、中心から外周部へ1cm刻みの場所の膜厚を測定し、平均値、及び最大値と最小値との差を表2に示した。膜厚は大日本スクリーン製造社製膜厚測定装置(ラムダエース)にて測定した。
上記感光性樹脂組成物を室温にて2週間保存し、初期粘度に対する粘度変化率を表2に示す。粘度はE型粘度計を用いて測定した。
上記感光性樹脂組成物を東京エレクトロン社製スピンコーター(CLEANTRACK MK−8)にて、6インチシリコンウエハーにスピン塗布し、表2に示す条件で、ホットプレートにてプリベークを行い、10μm厚の塗膜を形成した。膜厚は大日本スクリーン製造社製膜厚測定装置(ラムダエース)にて測定した。
Claims (7)
- ポリイミド構造、ポリベンゾオキサゾール構造、ポリイミド前駆体構造、及びポリベンゾオキサゾール前駆体構造からなる群から選ばれる1種以上の構造を有する樹脂を含むアルカリ可溶性樹脂(A)100質量部、
下記一般式(1):
で表される化合物、及び下記一般式(2):
で表される化合物からなる群より選ばれる少なくとも1種の化合物を含む溶剤(B)10〜1000質量部、並びに
感光剤(C)0.1〜100質量部、
を含有する、感光性樹脂組成物。 - 前記アルカリ可溶性樹脂(A)が、下記一般式(3):
で表される構造及び/又は下記一般式(4):
で表される構造を有する樹脂である、請求項1に記載の樹脂組成物。 - 架橋剤(D)1〜100質量部をさらに含有する、請求項1又は2に記載の感光性樹脂組成物。
- 前記架橋剤(D)が、メチロール基及び/又はアルコキシメチル基を有する芳香族化合物、並びにN位がメチロール基及び/又はアルコキシメチル基で置換された化合物からなる群から選ばれる少なくとも1種の化合物である、請求項3に記載の感光性樹脂組成物。
- 前記一般式(1)及び(2)中のR1及びR2が、それぞれ独立に、水酸基及び/又はエステル基を有する炭化水素基である、請求項1〜4のいずれか1項に記載の感光性樹脂組成物。
- (1)請求項1〜5のいずれか1項に記載の感光性樹脂組成物を基板上に塗布することによって感光性樹脂層を該基板上に形成する工程、
(2)該感光性樹脂層を露光する工程、
(3)該露光後の感光性樹脂層を現像することによってレリーフパターンを形成する工程、及び
(4)得られたレリーフパターンを加熱処理することによって硬化レリーフパターンを形成する工程、
を含む、硬化レリーフパターンの製造方法。 - 請求項6に記載の硬化レリーフパターンの製造方法により得られる硬化レリーフパターンからなる樹脂膜を有する、半導体装置。
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