JP5079089B2 - 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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- JP5079089B2 JP5079089B2 JP2010514472A JP2010514472A JP5079089B2 JP 5079089 B2 JP5079089 B2 JP 5079089B2 JP 2010514472 A JP2010514472 A JP 2010514472A JP 2010514472 A JP2010514472 A JP 2010514472A JP 5079089 B2 JP5079089 B2 JP 5079089B2
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-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
- 150000003573 thiols Chemical class 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- IYQYZZHQSZMZIG-UHFFFAOYSA-N tricyclo[5.2.1.0(2.6)]deca-3,8-diene, 4.9-dimethyl Chemical compound C1C2C3C=C(C)CC3C1C=C2C IYQYZZHQSZMZIG-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
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-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
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-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
- 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
- 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
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
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Description
特許文献4では、PBO前駆体又はPI前駆体にナフトキノンジアジド化合物と特定の有機酸とを添加することによってネガ型パターニングが可能な組成物が提案されている。
特許文献5では、PBO前駆体にm−トルイル酸やm−アニス酸等の有機酸とアルコール成分とを必須成分として組み合わせることで得られる高感度な感光性樹脂組成物が提案されている。
で表される構造及び下記一般式(2):
で表される構造からなる群より選ばれる少なくとも1種の構造を有するアルカリ水溶液可溶性重合体(以下、「(A)アルカリ水溶液可溶性重合体」ともいう)100質量部、
(B)光酸発生剤1〜50質量部、並びに
(C)カルボキシル基のα位にヒドロキシル基、エーテル基及びエステル基からなる群より選ばれる官能基を少なくとも1つ有する炭素原子数8以上のモノカルボン酸化合物(以下、「(C)モノカルボン酸化合物」ともいう)5〜20質量部、
を含む、感光性樹脂組成物。
で表されかつ炭素原子数8〜30である化合物からなる群より選ばれる少なくとも1種の化合物である、上記[1]又は[2]に記載の感光性樹脂組成物。
で表されかつ炭素原子数8〜30である化合物からなる群より選ばれる少なくとも1種の化合物である、上記[1]〜[3]のいずれかに記載の感光性樹脂組成物。
で表される構造を有する、上記[1]〜[4]のいずれかに記載の感光性樹脂組成物。
で表される構造を有する、上記[1]〜[5]のいずれかに記載の感光性樹脂組成物。
からなる群より選ばれる少なくとも1種のポリイミド構造を分子内に有する、上記[1]〜[6]のいずれかに記載の感光性樹脂組成物。
で表される末端基からなる群より選ばれる少なくとも1種の末端基を含む、上記[1]〜[7]のいずれかに記載の感光性樹脂組成物。
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種の化合物である、上記[9]に記載の感光性樹脂組成物。
(2)マスクを介した化学線で感光性樹脂層を露光して露光部を形成するか、又は光線、電子線若しくはイオン線を感光性樹脂層の一部に直接照射して照射部を形成する工程、
(3)感光性樹脂層の該露光部又は該照射部を溶出させて除去することによってレリーフパターンを形成する現像工程、並びに
(4)得られたレリーフパターンを加熱処理して硬化レリーフパターンを形成する加熱工程
を含む、硬化レリーフパターンの製造方法。
本発明に係る感光性樹脂組成物は、
(A)下記一般式(1):
で表される構造及び下記一般式(2):
で表される構造からなる群より選ばれる少なくとも1種の構造を有するアルカリ水溶液可溶性重合体(以下、「(A)アルカリ水溶液可溶性重合体」ともいう)100質量部、
(B)光酸発生剤1〜50質量部、並びに
(C)カルボキシル基のα位にヒドロキシル基、エーテル基及びエステル基からなる群より選ばれる官能基を少なくとも1つ有する炭素原子数8以上のモノカルボン酸化合物(以下、「(C)モノカルボン酸化合物」ともいう)5〜20質量部、
を含む。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、各一般式中で同一符号を用いて表されている構造は、分子中に複数存在する場合には特記がない限り互いに同一であっても異なっていてもよい。
本発明の感光性樹脂組成物のベースポリマーである(A)アルカリ水溶液可溶性重合体は、下記一般式(1):
で表される構造及び下記一般式(2):
で表される構造からなる群より選ばれる少なくとも1種の構造を有する。
で表される構造を有してもよい。一般式(13)で表される構造を有する重合体としては、X1(NH2)2(OH)2(例えばビスアミノフェノール)に由来する構造と、X5(NH2)2の構造を有するジアミンに由来する構造とを有する重合体が挙げられる。
で表される構造を有してもよい。一般式(14)で表される構造を有する重合体としては、X2(NH2)2(OH)2(例えばビスアミノフェノール)に由来する構造と、X6(NH2)2(OH)(例えばアミノフェノール)又はX6(NH2)2の構造を有するジアミンに由来する構造とを有する重合体が挙げられる。
X7は、X1で表される有機基の好ましいものとして前述した有機基からなる群より選ばれる少なくとも1種の有機基であることが好ましい。
Y5は、Y1で表される有機基の好ましいものとして後述する有機基からなる群より選ばれる少なくとも1種の有機基であることが好ましい。
並びに
からなる群より選ばれる芳香族基又は脂肪族基であるジカルボン酸が挙げられる。得られる樹脂膜の機械物性が良好である点で、上記L8、L9、L10及びL11は水素原子であることが最も好ましい。
で表される構造を含むことが好ましい。
で表される構造を含むことが好ましい。
で表される化合物が挙げられる。
で表される化合物が挙げられる。
で表される基が挙げられる。
からなる群より選ばれる少なくとも1種のポリイミド構造を分子内に有することが好ましい。
で表される末端基からなる群より選ばれる少なくとも1種の末端基であることが好ましい。
(B)光酸発生剤としては、ナフトキノンジアジド構造を有する化合物、オニウム塩、ハロゲン含有化合物等を用いることができるが、溶剤溶解性及び保存安定性の観点から、ナフトキノンジアジド構造を有する化合物(以下、「ナフトキノンジアジド化合物」ともいう。)が好ましい。
で表される有機基からなる群より選ばれる少なくとも1種の2価の基を表す。}
で表されるポリヒドロキシ化合物のNQD化物。
で表されるポリヒドロキシ化合物のNQD化物。
で表されるポリヒドロキシ化合物のNQD化物。
で表される1価の有機基を表し、そしてm11、m12及びm13は、各々独立に0〜2の整数である。}
で表されるポリヒドロキシ化合物のNQD化物。
で表されるポリヒドロキシ化合物のNQD化物。
で表される1価の有機基を表し、R35、R36及びR37は、各々独立に、水素原子、又はアルキル基及びシクロアルキル基からなる群より選ばれる少なくとも1種の1価の基を表し、そして、m15、m16及びm17は、各々独立に0〜2の整数である。}
で表されるポリヒドロキシ化合物のNQD化物。
(C)モノカルボン酸化合物は、カルボキシル基のα位にヒドロキシル基、エーテル基及びエステル基からなる群より選ばれる官能基を少なくとも1つ有する炭素原子数8以上のモノカルボン酸化合物である。
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種の化合物が、硬化時残膜率向上の観点から好ましい。上記一般式(3)で表される化合物の炭素原子数は8〜30であることが好ましい。
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種の化合物が、更なる硬化時残膜率向上の観点からより好ましい。上記一般式(4)で表される化合物の炭素原子数は8〜30であることが好ましい。また、Z2が有機基である場合、Z2は好ましくは炭素原子数1〜6の有機基である。
本発明の感光性樹脂組成物が(D)架橋し得る有機基を3つ以上有する化合物を含有することは、更なる硬化時残膜率向上及び加熱処理後の樹脂のガラス転移温度向上の観点から好ましい。特に、前述の(C)モノカルボン酸化合物と(D)架橋し得る有機基を3つ以上有する化合物とを組み合わせることにより、感光性樹脂組成物のキュア時の熱架橋性が向上する。
で表される化合物が挙げられる。その中でも感度の観点から、トリメチロールプロパントリメタクリレート、トリメリット酸トリアリル、及び上記一般式(11)で表される化合物が好ましい。上記一般式(11)で表される化合物の具体例として、下記式(12):
本発明の感光性樹脂組成物には、必要に応じて、ヒドロキシル基含有化合物、感光性樹脂組成物の添加剤として知られているフェノール化合物、染料、界面活性剤、安定剤、感光性樹脂組成物を用いて形成される膜とシリコンウエハーとの接着性を高めるための接着助剤等を1種又は2種以上配合することも可能である。以下、配合できる添加剤のより詳細な例について具体的に述べる。
本発明の感光性樹脂組成物は、溶媒に溶解してワニス状にし、感光性樹脂組成物溶液として使用することが好ましい。このような溶媒としては、N−メチル−2−ピロリドン、γ−ブチロラクトン(以下、「GBL」ともいう。)、シクロペンタノン、シクロヘキサノン、イソホロン、N,N−ジメチルアセトアミド(以下、「DMAc」ともいう。)、ジメチルイミダゾリノン、テトラメチルウレア、ジメチルスルホキシド、ジエチレングリコールジメチルエーテル(以下、「DMDG」ともいう。)、ジエチレングリコールジエチルエーテル、ジエチレングリコールジブチルエーテル、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、ジ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メチルエーテルアセテート、乳酸メチル、乳酸エチル、乳酸ブチル、メチル−1,3−ブチレングリコールアセテート、1,3−ブチレングリコール−3−モノメチルエーテル、ピルビン酸メチル、ピルビン酸エチル、メチル−3−メトキシプロピオネート等を単独で又は2種以上混合して使用できる。これらの溶媒のうち、非アミド系溶媒がフォトレジスト等への影響が少ない点から好ましい。具体的なより好ましい例としてはγ−ブチロラクトン、乳酸エチル、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メチルエーテルアセテート、テトラヒドロフルフリルアルコール等を挙げることができる。これらの有機溶剤は単独で使用しても2種以上混合して使用してもよい。
本発明は、上述した本発明の感光性樹脂組成物を用いる硬化レリーフパターンの製造方法も提供し、該製造方法は、
(1)上述した本発明の感光性樹脂組成物からなる感光性樹脂層を基板上に形成する工程、
(2)マスクを介した化学線で感光性樹脂層を露光して露光部を形成するか、又は光線、電子線若しくはイオン線を感光性樹脂層の一部に直接照射して照射部を形成する工程、
(3)感光性樹脂層の該露光部又は該照射部を溶出させて除去することによってレリーフパターンを形成する現像工程、並びに
(4)得られたレリーフパターンを加熱処理して硬化レリーフパターンを形成する加熱工程
を含む。本発明に係る硬化レリーフパターンの製造方法について、以下具体的に説明する。
この工程では、感光性樹脂組成物を、典型的には感光性樹脂組成物溶液の形態で、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、感光性樹脂組成物溶液を所定の場所に塗布することも可能である。このようにして感光性樹脂組成物溶液が塗布された基板を、オーブン又はホットプレートを用いて50〜140℃、好ましくは100〜140℃に加熱して溶媒を乾燥除去し(以下、「ソフトベーク」又は「プリベーク」ともいう。)、基板上に感光性樹脂層を形成する。
続いて、マスクを介した化学線で感光性樹脂層を露光して露光部を形成するか、又は光線、電子線若しくはイオン線を感光性樹脂層の一部に直接照射して照射部を形成する。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、又は、光線、電子線若しくはイオン線を感光性樹脂層の所定部分に直接照射する。活性光線である化学線としては、例えばg線、h線、i線及びKrFレーザーを使用できる。
続いて、感光性樹脂層の露光部又は照射部を現像液で溶出(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。現像方法としてはスプレー、パドル、ディップ、超音波等の方式が可能である。リンス液としては蒸留水、脱イオン水等が使用できる。
最後に、得られたレリーフパターンを加熱処理する(以下、この工程を「キュア」という。)。キュアによって、例えば(A)アルカリ水溶液可溶性重合体が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からなる耐熱性硬化レリーフパターンを形成することができる。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、電磁誘導等による加熱が推奨される。加熱温度は200〜450℃が好ましく、250〜400℃がさらに好ましい。また加熱時間は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。
以上のような方法により硬化レリーフパターンを形成することができる。
<ビス(カルボキシ)トリシクロ[5,2,1,02,6]デカンの製造>
〔参考例1〕
テフロン(登録商標)製の碇型攪拌器を取り付けた、ガラス製のセパラブル3つ口フラスコに、トリシクロ[5,2,1,02,6]デカンジメタノール(東京化成工業社製)71.9g(0.366mol)をアセトニトリル1Lに溶解させたものを加え、さらに、イオン交換水1.4Lにりん酸水素二ナトリウム256.7g(1.808mol)及びりん酸二水素ナトリウム217.1g(1.809mol)を溶解させたものを加えた。これに、2,2,6,6−テトラメチルピペリジン−1−オキシル(東京化成工業社製、以下、「TEMPO」ともいう。)2.8g(0.0179モル)を添加し、攪拌して溶解させた。
〔参考例2〕
参考例1で得たビス(カルボキシ)トリシクロ[5,2,1,02,6]デカン62.5g(278mmol)、塩化チオニル97mL(1.33モル)、及びピリジン0.4mL(5.0mmol)を反応容器に仕込み、25〜50℃で18時間攪拌し、反応させた。反応終了後、反応生成物にトルエンを加え、減圧下で、過剰の塩化チオニルをトルエンと共沸させることで反応生成物を濃縮し、オイル状のビス(クロロカルボニル)トリシクロ[5,2,1,02,6]デカンを73.3g(収率100%)得た。
〔参考例3〕
容量2L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197.8g(0.54mol)、ピリジン75.9g(0.96mol)、DMAc692gを室温(25℃)で混合攪拌し溶解させた。これに、別途DMDG88g中に5−ノルボルネン−2,3−ジカルボン酸無水物(東京化成工業社製)19.7g(0.12mol)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40分、反応液温は最大で28℃であった。
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 SE−61
テフロン(登録商標)製の碇型攪拌器を取り付けた、ガラス製のセパラブル3つ口フラスコに、ビス(3−アミノ−4−ヒドロキシフェニル)プロパン(クラリアントジャパン社製)(以下、「BAP」ともいう。)69.17g(268mmol)、NMP276g、ピリジン12.7g(160mmol)を加え、窒素導入管を取り付け、窒素ガスを流した状態で攪拌してBAPを溶解させた。BAPが溶解した後、反応容器を、メタノールにドライアイスを加えた容器に浸して冷却した。参考例2で製造したビス(クロロカルボニル)トリシクロ[5,2,1,02,6]デカン69.99g(268mmol)をγ−ブチロラクトン280gに溶解させ、−10〜−19℃に保って30分を要して反応容器に滴下した。滴下終了後、反応容器を氷浴に浸し、0〜10℃に保って2時間攪拌した。さらにピリジン29.65g(375mmol)を反応容器に加えた。
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
テフロン(登録商標)製の碇型攪拌器を取り付けた、ガラス製のセパラブル4つ口フラスコに、ディーンスタークトラップ付き冷却管を取り付けた。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(東京化成工業株式会社製)35.14g(133ミリモル)、ビス(3,4−ジカルボキシフェニル)エーテル二無水物41.26g(133ミリモル)、BAP72.28g(280ミリモル)、γ−ブチロラクトン254.6g、トルエン60gを加えて、室温で100rpm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(28ミリモル)を加えて、窒素ガスを通じながらシリコン浴温度50℃で、100rpmで8時間加熱攪拌した。その後、シリコン浴温度180℃に加温し、100rpmで2時間加熱攪拌した。反応中トルエン及び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。
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2lのセパラブルフラスコ中で、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105.7g(0.4mol)、イソブチルアルコール59.3g(0.8mol)及びGBL320gを室温(25℃)で混合攪拌し溶解させ、氷冷下で攪拌しながらピリジン63.3g(0.8mol)を加え、発熱終了後室温まで放冷し、16時間放置した。
これに、ジシクロヘキシルカルボジイミド165g(0.8mol)をGBL120gに溶解した溶液を氷冷下で攪拌しながら40分間で加え、続いて4,4’−ジアミノジフェニルエーテル74.5g(0.37mol)をGBL150gに懸濁したものを同様に氷冷下で攪拌しながら60分間で加えた。室温で2時間攪拌後、エチルアルコール30mlを加えて、1時間攪拌し、更にDMAc250mlとTHF400mlを加えた後、沈殿を吸引濾過により除去して得られた反応液を15lのエチルアルコールに加え、生成した沈殿を濾別した後、真空乾燥してポリアミド酸エステル(P−4)としてPI前駆体を得た。このようにして合成されたアルカリ水溶液可溶性重合体のGPCによる重量平均分子量は、ポリスチレン換算で33000の単一のシャープな曲線であった。GPCの分析条件を以下に記す。
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
〔参考例7〕
容量1Lのセパラブルフラスコに、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109.9g(0.3mol)、テトラヒドロフラン(THF)330g、ピリジン47.5g(0.6mol)を入れ、これに室温下で5−ノルボルネン−2,3−ジカルボン酸無水物98.5g(0.6mol)を粉体のまま加えた。そのまま室温で3日間撹拌反応を行ったあと、HPLCにて反応を確認したところ、原料は全く検出されず、生成物が単一ピークとして純度99%で検出された。この反応液をそのまま1Lのイオン交換水中に撹拌下で滴下し、析出物を濾別した後、該析出物にTHF500mlを加え撹拌溶解し、得られた均一溶液を陽イオン交換樹脂:アンバーリスト15(オルガノ社製)100gが充填されたガラスカラムに通し、残存するピリジンを除去した。次にこの溶液を3Lのイオン交換水中に高速撹拌下で滴下することにより生成物を析出させ、これを濾別した後、真空乾燥した。
容量1Lのセパラブルフラスコに、ポリヒドロキシ化合物として4,4’−(1−(2−(4−ヒドロキシフェニル)−2−プロピル)フェニル)エチリデン)ビスフェノール(本州化学工業社製、商品名:Tris−PA)の化合物30g(0.0707mol)を添加し、このOH基の83.3mol%に相当する量の1,2−ナフトキノンジアジド−4−スルフォン酸クロライド47.49g(0.177mol)をアセトン300gに撹拌溶解したものを添加した後、フラスコを恒温槽にて30℃に調整した。次にアセトン18gにトリエチルアミン17.9gを溶解し、滴下ロートに仕込んだ後、これを30分かけてフラスコ中へ滴下した。滴下終了後更に30分間撹拌を続け、その後塩酸を滴下し、更に30分間撹拌を行い反応を終了させた。その後濾過し、トリエチルアミン塩酸塩を除去した。ここで得られた濾液を、純水1640gと塩酸30gを混合撹拌した3Lビーカーに撹拌しながら滴下し、析出物を得た。この析出物を水洗及び濾過した後、40℃減圧下で48時間乾燥させ、感光性ジアゾキノン化合物(ナフトキノンジアジド化合物)(Q−2)を得た。
<接着助剤の調製>
反応容器としては、テフロン(登録商標)製の碇型攪拌器を取り付けた、ガラス製のセパラブル3つ口フラスコを用いた。反応容器に、二炭酸ジ−t−ブチル131.0gとγ−ブチロラクトン780gを入れ、室温下で3−アミノプロピルトリエトキシシラン132.8gとγ−ブチロラクトン270gを混合させた溶液をゆっくり室温下で滴下した。滴下するに従い、反応液は約40℃まで発熱した。また、反応に伴い、炭酸ガスの発生が確認された。滴下終了後、室温で2時間攪拌した後、高速液体クロマトグラフィー(HPLC)にて反応液を確認したところ、原料は全く検出されず、生成物の(3−トリエトキシシリルプロピル)−t−ブチルカルバメートが単一ピークとして純度98%で検出された。この様にして、接着助剤溶液を得た。
[実施例1〜21、比較例1〜11]
表1に記載する実施例1〜21、及び比較例1〜11の感光性樹脂組成物は、上記参考例3から6にて得られた耐熱性の(A)アルカリ水溶液可溶性重合体(P−1〜P−4)100質量部に対して、表1に示す量の、上記参考例7及び8にて得られた(B)ナフトキノンジアジド化合物(Q−1及びQ−2)、下記C−1からC−11の(C)モノカルボン酸化合物、及び下記D−1からD−3の(D)架橋し得る有機基を分子内に3つ以上有する化合物を適宜GBL170〜220質量部に溶解させた後、参考例9で得られた接着助剤を30質量部加え、0.2μmのフィルターで濾過して調製した。
(C−2)ヒドロキシマンデル酸
(C−3)4−ヒドロキシ−3−メトキシマンデル酸
(C−4)マンデル酸
(C−5)アトロラクチン酸
(C−6)O−アセチルマンデル酸
(C−7)α−メトキシフェニル酢酸
(C−8)2−フェニル酪酸
(C−9)3−(4−ヒドロキシフェニル)プロピオン酸
(C−10)トロパ酸
(C−11)m−トルイル酸
(D−1)BANI−X(丸善石油化学:商品名)
(D−2)トリメチロールプロパントリメタクリレート
(D−3)トリメリット酸トリアリル
(1)パターニング特性評価
・プリベーク膜の作製及び膜厚測定
上記実施例及び比較例の感光性樹脂組成物をスピンコーター(東京エレクトロン社製 クリーントラックMark8)にて、6インチシリコンウエハーにスピン塗布し、ホットプレート上125℃及び180秒間でプリベークして評価用膜を得た。各組成物の初期膜厚は、320℃で1時間キュアした時の硬化後樹脂膜厚で、P−1及びP−2は7μm、P−3は5μmとなるように調整した。膜厚は膜厚測定装置(大日本スクリーン製造社製ラムダエース)にて測定した。
この評価用膜を、テストパターン付きレチクルを通してi線(365nm)の露光波長を有するステッパー(ニコン社製NSR2005i8A)を用いて露光量を段階的に変化させて露光した。
・現像
露光後の膜を、アルカリ現像液(AZエレクトロニックマテリアルズ社製AZ300MIFデベロッパー、2.38質量%水酸化テトラメチルアンモニウム水溶液)を用い、23℃の条件下で現像後膜厚が初期膜厚の85%となるように現像時間を調整して現像し、純水にてリンスを行い、ポジ型のレリーフパターンを形成した。
・キュア膜の作製
次いで、現像後の膜を昇温式オーブン(光洋サーモシステム社製 VF200B)を用いて320℃で1時間キュアし、硬化レリーフパターンを有するキュア膜を作製した。
なお、感光性樹脂組成物の感度及び硬化時残膜率を次のようにして評価した。結果を以下の表2に示す。
感度(mJ/cm2)は、規定現像後膜厚において、塗膜の露光部を完全に溶解除去しうる最小露光量と規定した。
[硬化時残膜率(%)]
硬化時残膜率(%)は、(キュア後の硬化レリーフパターンの膜厚)/(現像後のレリーフパターンの膜厚)×100と規定した。
Claims (13)
- (A)下記一般式(1):
で表される構造及び下記一般式(2):
で表される構造からなる群より選ばれる少なくとも1種の構造を有するアルカリ水溶液可溶性重合体100質量部、
(B)光酸発生剤1〜50質量部、並びに
(C)カルボキシル基のα位にヒドロキシル基、エーテル基及びエステル基からなる群より選ばれる官能基を少なくとも1つ有する炭素原子数8以上のモノカルボン酸化合物5〜20質量部、
を含む、感光性樹脂組成物。 - 前記(B)光酸発生剤が、ナフトキノンジアジド構造を有する化合物である、請求項1に記載の感光性樹脂組成物。
- (D)架橋し得る有機基を分子内に3つ以上有する化合物を、前記(A)アルカリ水溶液可溶性重合体100質量部に対して1〜40質量部の量で更に含む、請求項1に記載の感光性樹脂組成物。
- (1)請求項1〜11のいずれか1項に記載の感光性樹脂組成物からなる感光性樹脂層を基板上に形成する工程、
(2)マスクを介した化学線で感光性樹脂層を露光して露光部を形成するか、又は光線、電子線若しくはイオン線を感光性樹脂層の一部に直接照射して照射部を形成する工程、
(3)感光性樹脂層の該露光部又は該照射部を溶出させて除去することによってレリーフパターンを形成する現像工程、並びに
(4)得られたレリーフパターンを加熱処理して硬化レリーフパターンを形成する加熱工程
を含む、硬化レリーフパターンの製造方法。 - 請求項12に記載の製造方法により得られる硬化レリーフパターンを有してなる、半導体装置。
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KR102337564B1 (ko) * | 2018-09-28 | 2021-12-13 | 삼성에스디아이 주식회사 | 감광성 수지 조성물, 이를 이용한 감광성 수지막 및 전자 소자 |
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CN114721223A (zh) * | 2020-12-22 | 2022-07-08 | 华为技术有限公司 | 感光性树脂、感光性树脂组合物、固化物、图案形成方法以及集成电路器件 |
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