JP2022053108A - 感光性樹脂組成物、パターン形成方法、硬化被膜形成方法、層間絶縁膜、表面保護膜、及び電子部品 - Google Patents
感光性樹脂組成物、パターン形成方法、硬化被膜形成方法、層間絶縁膜、表面保護膜、及び電子部品 Download PDFInfo
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- JP2022053108A JP2022053108A JP2020159730A JP2020159730A JP2022053108A JP 2022053108 A JP2022053108 A JP 2022053108A JP 2020159730 A JP2020159730 A JP 2020159730A JP 2020159730 A JP2020159730 A JP 2020159730A JP 2022053108 A JP2022053108 A JP 2022053108A
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 8
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 7
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- 239000002585 base Substances 0.000 description 7
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- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
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- 238000009835 boiling Methods 0.000 description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 description 6
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- 238000000354 decomposition reaction Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
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- ODOCEKVZTLEAAP-UHFFFAOYSA-N methyl 3-[2-hydroxyethyl-(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CCC(=O)OC ODOCEKVZTLEAAP-UHFFFAOYSA-N 0.000 description 1
- WYPIYJCVKPAZOQ-UHFFFAOYSA-N methyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCOC(C)=O)CCOC(C)=O WYPIYJCVKPAZOQ-UHFFFAOYSA-N 0.000 description 1
- PDLCQBOPNILNFH-UHFFFAOYSA-N methyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CCO PDLCQBOPNILNFH-UHFFFAOYSA-N 0.000 description 1
- BHTBQFHOJIBPKY-UHFFFAOYSA-N methyl 3-[bis(2-methoxyethyl)amino]propanoate Chemical compound COCCN(CCOC)CCC(=O)OC BHTBQFHOJIBPKY-UHFFFAOYSA-N 0.000 description 1
- YDNHCHDMPIHHGH-UHFFFAOYSA-N methyl 3-[bis(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)CCC(=O)OC YDNHCHDMPIHHGH-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- 238000001471 micro-filtration Methods 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- BNUHBJSGYGOLSN-UHFFFAOYSA-N n'-[2-[2-[2-(dimethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound CN(C)CCNCCNCCNCCN BNUHBJSGYGOLSN-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
- KPPTXUHFJMLSFV-UHFFFAOYSA-N n,n-di(propan-2-yl)cyclohexanecarboxamide Chemical compound CC(C)N(C(C)C)C(=O)C1CCCCC1 KPPTXUHFJMLSFV-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- NILJCGYQNXKIRL-UHFFFAOYSA-N n,n-dicyclopentylcyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)C1CCCC1 NILJCGYQNXKIRL-UHFFFAOYSA-N 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- LYYLWJOKAQADDU-UHFFFAOYSA-N n,n-dihexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC LYYLWJOKAQADDU-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
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- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
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- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
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- YNHVYQBXAFEGAV-UHFFFAOYSA-N propan-2-yl azetidine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCC1 YNHVYQBXAFEGAV-UHFFFAOYSA-N 0.000 description 1
- VNNCLWNAWKLJRZ-UHFFFAOYSA-N propan-2-yl n,n-di(propan-2-yl)carbamate Chemical compound CC(C)OC(=O)N(C(C)C)C(C)C VNNCLWNAWKLJRZ-UHFFFAOYSA-N 0.000 description 1
- XQEPLYLEYBCDLB-UHFFFAOYSA-N propan-2-yl pyrrolidine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCCC1 XQEPLYLEYBCDLB-UHFFFAOYSA-N 0.000 description 1
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- XFHDOSGLKQJYLP-UHFFFAOYSA-N tert-butyl 2,6-dimethylpiperidine-1-carboxylate Chemical compound CC1CCCC(C)N1C(=O)OC(C)(C)C XFHDOSGLKQJYLP-UHFFFAOYSA-N 0.000 description 1
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- QUERMGFVJPRMJL-UHFFFAOYSA-N tert-butyl azetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC1 QUERMGFVJPRMJL-UHFFFAOYSA-N 0.000 description 1
- HNURUDICJPOGGD-UHFFFAOYSA-N tert-butyl n,n-di(propan-2-yl)carbamate Chemical compound CC(C)N(C(C)C)C(=O)OC(C)(C)C HNURUDICJPOGGD-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
- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 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
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
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- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-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
- 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
- 239000013638 trimer Substances 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-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
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Classifications
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- 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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Abstract
Description
(A)樹脂、
(B)感光剤、
(C)下記平均組成式(1)で表される構造単位を含む界面活性剤、及び
(D)溶剤
を含むものである感光性樹脂組成物を提供する。
(II)次いで加熱処理後、フォトマスクを介して波長190~500nmの高エネルギー線もしくは電子線で感光材被膜を露光する工程、
(III)アルカリ水溶液もしくは有機溶剤の現像液を用いて現像する工程、
を含むパターン形成方法を提供する。
(A)樹脂、
(B)感光剤、
(C)下記平均組成式(1)で表される構造単位を含む界面活性剤、及び
(D)溶剤
を含むものである感光性樹脂組成物である。
(A)樹脂は、本発明の感光性樹脂組成物のベースとなる樹脂であり、ポジ型感光性樹脂組成物かネガ型感光性樹脂組成物か、前記樹脂を用いた感光性樹脂組成物からなる硬化膜に要求される機械特性、光学特性などに応じて選択することができ、ポリアミド、ポリアミドイミド、ポリイミド、ポリイミド前駆体、ポリベンゾオキサゾール、ポリベンゾオキサゾール前駆体、シロキサン骨格含有樹脂から選択される樹脂であることが好ましく、1種又は2種以上を組み合わせて用いることができる。
樹脂は、下記一般式(3)、(4)、(5)、(7)で表される構造単位から選ばれる少なくとも1種を含むものであることが好ましい。
樹脂は、下記一般式(14)で表される構造単位を含むものであることが好ましい。
(B)感光剤は、光を受けて樹脂を溶剤に対して可溶若しくは不溶にする作用を有する物質である。ポジ型感光性樹脂組成物又はネガ型感光性樹脂組成物を構築するための、以下のような(B)成分を用いることができる。なお、(B)成分は1種又は2種以上を用いることができ、2種以上の場合は、それぞれ異なる機能を有していてもよい。また、(B)成分は、光により酸を発生する化合物(光酸発生剤)であることができる。
本発明においてポジ型感光性樹脂組成物を構築するためには(B)成分は、光により酸を発生しアルカリ水溶液に対する溶解速度が増大する感光剤であって、キノンジアジド構造を有する化合物であることが好ましい。(B)成分としては、1,2-ナフトキノンジアジドスルホニル基を分子中に有する化合物を挙げることができる。
即ち、現像液にアルカリ水溶液を用いた場合、未露光部は現像液に溶解することがなく、露光部は現像液に可溶であることから、ポジ型のパターンを形成することが可能となる。
また本発明においてネガ型感光性樹脂組成物を構築するためには、(B)成分は光により酸を発生する化合物が好ましい。(B)成分から発生する酸を触媒として、後述する(E)成分の架橋基が(A)成分の樹脂と架橋することによって、ネガ型の感光性樹脂組成物を成すことができる。
(R32)j1M+K- (28)
(式中、R32は置換基を有してもよい炭素数1~12の直鎖状、分岐状、又は環状のアルキル基、炭素数6~12のアリール基又は炭素数7~12のアラルキル基を表し、M+はヨードニウム又はスルホニウムを表し、K-は非求核性対向イオンを表し、j1は2又は3を表す。)
本発明の感光性樹脂組成物は下記平均組成式(1)で表される構造単位を含む界面活性剤を含有する。下記平均組成式(1)で表される構造単位を含むことで、ポジ型感光性樹脂組成物、ネガ型感光性樹脂組成物のいずれにおいても塗布時の膜厚均一性に優れ、厚膜形成時の塗布欠陥を低減することができる。
本発明の感光性樹脂組成物は、必要に応じて、(E)ホルムアルデヒド又はホルムアルデヒド-アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(E-1)で示される置換基に置換した化合物、及び下記式(E-2)で示されるグリシジル基を有した窒素原子を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤を含むことができる。
上記R34としては、例えば、メチロール基、メトキシメチル基、エトキシメチル基等のアルコキシメチル基及び水素原子等が挙げられる。
上記ホルムアルデヒド又はホルムアルデヒド-アルコールにより変性された尿素縮合物の具体例としては、例えば、メトキシメチル化尿素縮合物、エトキシメチル化尿素縮合物、プロポキシメチル化尿素縮合物等が挙げられる。
なお、これら変性メラミン縮合物及び変性尿素縮合物の1種又は2種以上を混合して使用することもできる。また、上記変性メラミンも(E)成分として用いることができる。
本発明の感光性樹脂組成物は(D)溶剤を含むものである。(D)成分の溶剤は、ポジ型感光性樹脂組成物、ネガ型感光性樹脂組成物のいずれにも含まれ、(A)成分、(B)成分、(C)成分及び含まれる場合には(E)成分を溶解するものであれば、特に限定されない。溶剤としては、例えば、シクロヘキサノン、シクロペンタノン、メチル-2-n-アミルケトン等のケトン類;3-メトキシブタノール、3-メチル-3-メトキシブタノール、1-メトキシ-2-プロパノール、1-エトキシ-2-プロパノール等のアルコール類;プロピレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル類;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、乳酸エチル、ピルビン酸エチル、酢酸ブチル、3-メトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、酢酸tert-ブチル、プロピオン酸tert-ブチル、プロピレングリコール-モノ-tert-ブチルエーテルアセテート、γ-ブチロラクトン等のエステル類;N-メチル-2-ピロリドン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド等のアミド系の溶剤が挙げられ、これらの1種以上を用いることができる。特に、乳酸エチル、シクロヘキサノン、シクロペンタノン、プロピレングリコールモノメチルエーテルアセテート、γ-ブチロラクトン、N-メチル-2-ピロリドン又はそれらの混合溶剤が好ましい。
また、本発明の感光性樹脂組成物において、必須の(A)成分、(B)成分、(C)成分、及び(D)成分以外の成分をさらに含有してもよい。その他の成分としては、例えば、上記(E)成分の他、(F)熱によって酸を発生する化合物、(G)酸化防止剤、(H)シラン化合物、(I)塩基性化合物、(J)保護アミン化合物、(K)溶解阻害剤、(L)ラジカル重合性化合物等を挙げることができる。
(F)成分の熱によって酸を発生する化合物は、上記のパターン形成後施される温度100~300℃において加熱、後硬化する工程において、熱的に(A)成分と(E)成分との架橋反応を促す目的で加えることができる。
(G)成分の酸化防止剤を含むことで、(A)成分の脂肪族基やフェノール性水酸基の酸化劣化を抑制する。また、金属材料への防錆作用により、外部からの水分や光酸発生剤、熱酸発生剤などによる金属酸化やそれに伴う密着低下や剥離を抑制することができる。
(H)成分のシラン化合物は、これを含むことで、金属材料に対する密着性を向上するだけでなく、熱衝撃試験や高温高湿試験といった信頼性試験における硬化膜の剥離を抑制することができる。
(I)成分の塩基性化合物は、これを含むことで、光酸発生剤より発生する酸がレジスト皮膜を拡散する際の拡散速度を抑制することができる。ネガ型感光性樹脂組成物の場合、上記塩基性化合物の配合により、解像度が向上し、露光後の感度変化を抑制し、基板や環境依存性を少なくし、露光余裕度やパターン形状等を改善することができる。
N(α)q(β)3-q (31)
イミド誘導体としては、例えばフタルイミド、サクシンイミド、マレイミド等が例示される。
本発明の感光性樹脂組成物は(J)成分の保護アミン化合物を含むことができる。(E)成分の架橋剤が反応性の高いものの場合、アミン化合物を直接添加すると、室温下で(E)成分とアミン化合物が反応し、経時的に組成物の粘度が増粘し、保存安定性が劣化する懸念がある。一方、保護基によって、塩基性基が保護されたアミン化合物ならば、(E)成分の架橋剤とは室温下で反応することがないため、感光性樹脂組成物の経時的な保存安定性を高めることができる。また、加熱した際に初めて塩基が発生するので、(A)成分の1種であるイミド前駆体の閉環反応や(A)成分の樹脂と(E)成分の架橋剤との架橋反応の触媒となり、架橋反応を効果的に促進することができる。
また、R41は、置換基を有していてもよい炭素数1~12のアルキル基、置換基を有していてもよい炭素数3~12のシクロアルキル基、置換基を有していてもよい炭素数2~12のアルケニル基、置換基を有していてもよい炭素数2~12のアルキニル基、炭素数1~3のアルキル基を置換基として有していてもよいアリール基、炭素数1~3のアルキル基を置換基として有していてもよいアラルキル基、又は置換基を有していてもよい複素環基を示す。(但し、R41を構成する炭素原子の合計の数は、12以下とする。)上記基が有していてもよい置換基としては、目的に応じていかなるものを用いてもよい。
本発明の感光性樹脂組成物は(K)成分の溶解阻害剤を含むことができる。溶解阻害剤としては、重量平均分子量が100~1,000、好ましくは150~800で、かつ分子内にフェノール性水酸基を2つ以上有する化合物の該フェノール性水酸基の水素原子を酸不安定基により全体として平均0~100モル%の割合で置換した化合物又は分子内にカルボキシ基を有する化合物の該カルボキシ基の水素原子を酸不安定基により全体として平均50~100モル%の割合で置換した化合物が挙げられる。
本発明の感光性樹脂組成物は(L)成分のラジカル重合性化合物を含むことができる。上述した(A)成分である一般式(5)で表されるポリイミド前駆体、光ラジカル開始剤と組み合わせることでネガ型感光性樹脂組成物を得ることができる。このような組成物であれば露光により発生したラジカルにより(L)成分のラジカル重合性化合物同士、もしくは一般式(5)中のRa及びRbのいずれかもしくは両方が上記一般式(6)で示されるラジカル重合性基の場合、(A)成分の樹脂とラジカル重合性化合物との架橋が進行することで、良好なネガ型パターンを得ることができる。このように(L)成分のラジカル重合性化合物は架橋剤として働くことから、1分子中に2個以上のラジカル重合性不飽和結合基を有する化合物が好ましい。
次に、本発明の感光性樹脂組成物を用いたパターン形成方法に関して、説明を行う。
また、上記パターン形成方法により得られたパターン形成された被膜をオーブンやホットプレートを用いて、温度100~300℃、好ましくは150~300℃、さらに好ましくは180~250℃において加熱、後硬化することで硬化被膜を形成することができる。後硬化温度が100~300℃であれば、感光性樹脂組成物の被膜の架橋密度を上げ、残存する揮発成分を除去でき、基板に対する密着力、耐熱性や強度、さらに電気特性の観点から好ましい。そして、後硬化時間は10分間~10時間とすることができる。
このようにして得られた硬化被膜は、基板との密着性、耐熱性、電気特性、機械的強度及びアルカリ性剥離液等に対する薬品耐性に優れ、それを保護用被膜とした半導体素子の信頼性にも優れ、特に温度サイクル試験の際のクラック発生を防止でき、電気・電子部品、半導体素子等の保護用被膜(層間絶縁膜あるいは表面保護膜)として好適に用いられる。
このような電子部品は、耐熱性、薬品耐性、絶縁性を有する保護用被膜(層間絶縁膜又は表面保護膜)を有することから、信頼性に優れたものとなる。
このような電子部品の具体例としては、IC(Integrated Circuit:集積回路)やLSI(Large-Scale Integrated Circuit:大規模集積回路)等の半導体集積回路素子、およびLED(Light Emitting Diode:発光ダイオード)やPD(Photo Diode:フォトダイオード)、CCD(Charged-Coupled Device:電荷結合素子)、CMOS(Complementary Metal-Oxide Semiconductor:相補型金属酸化膜半導体)等の光半導体素子、電流センサ素子または磁気センサ素子等のセンサ素子、半導体基板の表面に微小な電子機械機構が形成されてなるマイクロマシン、いわゆるMEMS(Micro electro mechanical systems:微小電気機械システム)素子等の種々の電子部品が挙げられる。
撹拌機、温度計を具備した1Lのフラスコ内に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(6FAP)30g(81.9mmol)、4-アミノフェノール(PAP)0.9g(8.6mmol)、N-メチル-2-ピロリドン125gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’-オキシジフタル酸二無水物(s-ODPA)26.7g(86.2mmol)、をN-メチル-2-ピロリドン270gに溶解した溶液を滴下し、滴下終了後室温下で3時間撹拌した。その後、この反応液にキシレン40gを加え、170℃で生成する水を系外へ除きながら3時間加熱還流を行った。室温まで冷却後、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリイミド樹脂(A1)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量35,000であった。
合成例1において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(6FAP)30g(81.9mmol)を2,2―ビス(3―アミノ―4―ヒドロキシフェニル)プロパン(BAP)21.2g(81.9mmol)に代え、それ以外は同様の処方でポリイミド樹脂(A2)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量34,000であった。
撹拌機、温度計を具備した500mLのフラスコ内に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(6FAP)28.5g(77.8mmol)、4-アミノフェノール(PAP)0.9g(8.2mmol)、N-メチル-2-ピロリドン118gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’-オキシジフタル酸二無水物(s-ODPA)19.0g(61.4mmol)、をN-メチル-2-ピロリドン192gに溶解した溶液を滴下し、滴下終了後室温下で3時間撹拌した。その後、この反応液にキシレン40gを加え、170℃で生成する水を系外へ除きながら3時間加熱還流を行った。室温まで冷却後、ピリジン3.2g(41.0mmol)を加え、セバシン酸ジクロライド(DC-1)4.9g(20.5mmol)を5℃以下に保つように滴下した。滴下終了後、室温まで戻し、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリアミドイミド樹脂(A3)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量35,000であった。
撹拌機、温度計を具備した500mLのフラスコ内に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(6FAP)28.5g(77.8mmol)、4-アミノフェノール(PAP)0.9g(8.2mmol)、N-メチル-2-ピロリドン118gを加え、室温で撹拌し溶解した。次にピリジン13.0g(163.8mmol)を加え、セバシン酸ジクロライド(DC-1)19.6g(81.9mmol)を5℃以下に保つように滴下した。滴下終了後、室温まで戻し、この反応液を超純水2Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリアミド樹脂(A4)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量38,000であった。
撹拌機、温度計を具備した3Lのフラスコ内に3,3’,4,4’-オキシジフタル酸二無水物(s-ODPA)100g(322mmol)、トリエチルアミン65.2g(644mmol)、N,N-ジメチル-4-アミノピリジン39.3g(322mmol)、γ-ブチロラクトン400gを加え、室温で撹拌しているところにヒドロキシエチルメタクリレート(HEMA)83.8g(644mmol)を滴下後、室温下で24時間撹拌した。その後、氷冷下で10%塩酸水溶液370gを滴下し反応を停止させた。反応液に、4-メチル-2-ペンタノン800gを加え有機層を分取した後、水600gで6回洗浄した。得られた有機層の溶媒を留去し、テトラカルボン酸ジエステル化合物(X-1)を180g得た。
撹拌機、温度計を具備した1Lのフラスコ内に(X-1)57.1g(100mmol)N-メチル-2-ピロリドン228gを加え、室温で撹拌し溶解した。次に氷冷下、塩化チオニル24.4g(205mmol)を反応溶液温度が10℃以下を保つように滴下し、滴下終了後氷冷下で2時間撹拌した。続いて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(6FAP)34.8g(95mmol)、4-アミノフェノール(PAP)1.1g(10mmol)、ピリジン32.4g(410mmol)をN-メチル-2-ピロリドン144gで溶解した溶液を氷冷下で反応溶液温度が10℃以下を保つように滴下した。滴下終了後、室温まで戻し、この反応液を水3Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリイミド前駆体(A5)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量36,000であった。
撹拌機、温度計を具備した1Lのフラスコ内に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(6FAP)27.5g(75mmol)、1,3-ビス(3-アミノフェノキシ)ベンゼン(APB)5.8g(20mmol)、4-アミノフェノール(PAP)1.1g(10mmol)、γ―ブチロラクトン138gを加え、室温で撹拌し溶解した。次に室温下、3,3’,4,4’-オキシジフタル酸二無水物(s-ODPA)12.4g(40mmol)、酸無水物変性シロキサン(DAN-1)110.5gをγ―ブチロラクトン492gに溶解した溶液を滴下し、滴下終了後室温下3時間撹拌した。その後、この反応液にキシレン40gを加え、170℃で生成する水を系外へ除きながら3時間加熱還流を行った。室温まで冷却後、このポリイミド溶液にグリシドール1.7g(22.5mmol)を加え、120℃で3時間加熱した。室温まで冷却し、この反応液を超純水4Lの撹拌下に滴下し、析出物をろ別し、適宜水洗後、40℃で48時間減圧乾燥することにより、ポリイミド樹脂(A6)を得た。この重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量20,000であった。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した10Lのフラスコ内に化合物(S-1)624g(1.45mol)をトルエン2,500gに溶解後、化合物(S-2)261.2g(0.62mol)、化合物(S-7)1,214.4g(0.40mol)、化合物(S-6)13.3g(0.10mol)を加え、60℃に加温した。その後、カーボン担持白金触媒(5質量%)3.5gを投入し、内部反応温度が65~67℃に昇温したのを確認後、更に、3時間、90℃まで加温し、再び60℃まで冷却して、カーボン担持白金触媒(5質量%)3.5gを投入し、化合物(S-5)285.2g(1.47mol)を1時間かけてフラスコ内に滴下した。このときフラスコ内温度は、65~67℃まで上昇した。滴下終了後、更に、90℃で3時間熟成し、室温まで冷却し、メチルイソブチルケトン2,800gを加え、本反応溶液をフィルターにて加圧濾過することで白金触媒を取り除いた。更に、得られたシロキサン骨格含有樹脂溶液に純水1,300gを加え、撹拌、静置分液を行い、下層の水層を除去した。この分液水洗操作を6回繰り返した。このシロキサン骨格含有樹脂溶液中の溶剤を減圧留去し、シロキサン骨格含有樹脂(A7)を得た。重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量31,000であった。
撹拌機、温度計、窒素置換装置及び還流冷却器を具備した10Lのフラスコ内に化合物(S-4)26.5g(0.10mol)、化合物(S-3)108.9g(0.90mol)、化合物(S-7)151.3g(0.05mol)、トルエン2,000gを加え、60℃に加温した。その後、カーボン担持白金触媒(5質量%)1.0gを投入し、内部反応温度が63~65℃に昇温したのを確認後、更に、3時間、90℃まで加温し、再び60℃まで冷却して、カーボン担持白金触媒(5質量%)1.0gを投入し、化合物(S-5)184.3g(0.95mol)を1時間かけてフラスコ内に滴下した。このときフラスコ内温度は、65~67℃まで上昇した。滴下終了後、更に、90℃で3時間熟成し、室温まで冷却し、メチルイソブチルケトン2,000gを加え、本反応溶液をフィルターにて加圧濾過することで白金触媒を取り除いた。更に、得られたシロキサン骨格含有樹脂溶液に純水1,000gを加え、撹拌、静置分液を行い、下層の水層を除去した。この分液水洗操作を6回繰り返した。このシロキサン骨格含有樹脂溶液中の溶剤を減圧留去し、シロキサン骨格含有樹脂(A8)を得た。重合体の分子量をGPCにより測定すると、ポリスチレン換算で重量平均分子量15,000であった。
上記合成例1~合成例9で合成した重合体をベース樹脂として使用して、表1に記載した組成と配合量で、樹脂換算30質量%の樹脂組成物を調製した。その後、撹拌、混合、溶解した後、テフロン(登録商標)製0.5μmフィルターで精密濾過を行って感光性樹脂組成物を得た。表中、溶剤のPGMEAはプロピレングルコールモノメチルエーテルアセテート、GBLはγ―ブチロラクトン、CPnはシクロペンタノンを示す。
・B1
・L1:ジエチレングリコールジアクリレート
上記の感光性樹脂組成物1~14、比較感光性樹脂組成物1~3を8インチのシリコン基板上へ5mLディスペンスした後に基板を回転することによって、即ち、スピンコート法によって、パターン形成後に施す後硬化の加熱後において膜厚が10μmとなるように塗布した。即ち、後硬化工程後、膜厚が減少することを予め検討し、後硬化後の仕上がり膜厚が10μmとなるように塗布時の回転数を調整した。次に、ホットプレート上100℃、2分間のプリベークを施した。
良好:ホールが矩形又は順テーパー形状(ホール上部の寸法が底部の寸法より大きい形状)が観察されたもの
不良:逆テーパー形状(ホール上部の寸法が底部の寸法より小さい形状)、オーバーハング形状(ホール上部が張り出した形状)、著しい膜減りが観察されたもの、又はホール底部に残渣が観察されたもの
また、R41は、置換基を有していてもよい炭素数1~12のアルキル基、置換基を有していてもよい炭素数3~12のシクロアルキル基、置換基を有していてもよい炭素数2~12のアルケニル基、置換基を有していてもよい炭素数2~12のアルキニル基、炭素数1~3のアルキル基を置換基として有していてもよいアリール基、炭素数1~3のアルキル基を置換基として有していてもよいアラルキル基、又は置換基を有していてもよい複素環基を示す。(但し、R41を構成する炭素原子の合計の数は、12以下とする。)上記基が有していてもよい置換基としては、目的に応じていかなるものを用いてもよい。
Claims (15)
- (A)樹脂、
(B)感光剤、
(C)下記平均組成式(1)で表される構造単位を含む界面活性剤、及び
(D)溶剤
を含むものであることを特徴とする感光性樹脂組成物。
- 前記一般式(2)中のaが10~30の整数、bが10~30の整数、cが0~20の整数であることを特徴とする請求項1に記載の感光性樹脂組成物。
- 前記一般式(2)中のR14が炭素数1~10の直鎖状もしくは分岐状のアルキルエステル基であることを特徴とする請求項1又は請求項2に記載の感光性樹脂組成物。
- (E)ホルムアルデヒド又はホルムアルデヒド-アルコールにより変性されたアミノ縮合物、1分子中に平均して2個以上のメチロール基又はアルコキシメチロール基を有するフェノール化合物、多価フェノールの水酸基の水素原子をグリシジル基に置換した化合物、多価フェノールの水酸基の水素原子を下記式(E-1)で示される置換基に置換した化合物、及び下記式(E-2)で示されるグリシジル基を有した窒素原子を2つ以上含有した化合物から選ばれる1種又は2種以上の架橋剤を更に含有するものであることを特徴とする請求項1から請求項3のいずれか一項に記載の感光性樹脂組成物。
- 前記(A)樹脂がポリアミド、ポリアミドイミド、ポリイミド、ポリイミド前駆体、ポリベンゾオキサゾール、ポリベンゾオキサゾール前駆体、シロキサン骨格含有樹脂から選択される少なくとも1種であることを特徴とする請求項1から請求項4のいずれか一項に記載の感光性樹脂組成物。
- 請求項5に記載の樹脂の重量平均分子量が、3,000~500,000であることを特徴とする感光性樹脂組成物。
- 前記(B)感光剤が光酸発生剤であることを特徴とする請求項1から請求項6のいずれか一項に記載の感光性樹脂組成物。
- 前記光酸発生剤がキノンジアジド構造を有する化合物であることを特徴とする請求項7に記載の感光性樹脂組成物。
- 前記(B)感光剤が光ラジカル開始剤であることを特徴とする請求項1から請求項6のいずれか一項に記載の感光性樹脂組成物。
- (I)請求項1から請求項9のいずれか一項に記載の感光性樹脂組成物を基板上に塗布し、感光材被膜を形成する工程、
(II)次いで加熱処理後、フォトマスクを介して波長190~500nmの高エネルギー線もしくは電子線で感光材被膜を露光する工程、
(III)アルカリ水溶液もしくは有機溶剤の現像液を用いて現像する工程、
を含むことを特徴とするパターン形成方法。 - 前記露光工程と前記現像工程との間に、露光後加熱工程を含むことを特徴とする請求項10に記載のパターン形成方法。
- 請求項10又は請求項11に記載のパターン形成方法により得られたパターン形成された被膜を、更に温度100~300℃において加熱、後硬化する工程を含むことを特徴とする硬化被膜形成方法。
- 請求項1から請求項9のいずれか一項に記載の感光性樹脂組成物の硬化被膜からなるものであることを特徴とする層間絶縁膜。
- 請求項1から請求項9のいずれか一項に記載の感光性樹脂組成物の硬化被膜からなるものであることを特徴とする表面保護膜。
- 請求項13に記載の層間絶縁膜又は請求項14に記載の表面保護膜を有するものであることを特徴とする電子部品。
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