JP6183029B2 - ネガ型感光性樹脂組成物および電子部品 - Google Patents
ネガ型感光性樹脂組成物および電子部品 Download PDFInfo
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- JP6183029B2 JP6183029B2 JP2013154380A JP2013154380A JP6183029B2 JP 6183029 B2 JP6183029 B2 JP 6183029B2 JP 2013154380 A JP2013154380 A JP 2013154380A JP 2013154380 A JP2013154380 A JP 2013154380A JP 6183029 B2 JP6183029 B2 JP 6183029B2
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- 239000010452 phosphate Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
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- 235000019795 sodium metasilicate Nutrition 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
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- PMTPAGVGEXGVNI-UHFFFAOYSA-N tetracyclo[10.2.1.02,11.04,9]pentadeca-2,4,6,13-tetraene Chemical compound C12=CC3=CC=CCC3CC2C2CC1C=C2 PMTPAGVGEXGVNI-UHFFFAOYSA-N 0.000 description 1
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- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
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- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- YOKZJDRCZXTECO-UHFFFAOYSA-N tricyclo[5.2.1.02,6]deca-3,8-diene-2-carboxylic acid Chemical compound C1=CC2CC1C1(C(=O)O)C2CC=C1 YOKZJDRCZXTECO-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
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- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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- 150000003682 vanadium compounds Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 0.000 description 1
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- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Description
さらに、本発明によれば、上記樹脂膜を備える電子部品が提供される。
本発明で用いるプロトン性極性基を有する環状オレフィン重合体(A)(以下、単に、「環状オレフィン重合体(A)」とする。)は、主鎖に、環状オレフィン単量体単位の環状構造(脂環または芳香環)を有する、環状オレフィン単量体の単独重合体又は共重合体であって、プロトン性極性基を有するものである。
本発明において、プロトン性極性基を有する環状オレフィン樹脂に結合しているプロトン性極性基の数に特に限定はなく、また、相異なる種類のプロトン性極性基が含まれていてもよい。
これら単量体(b2)は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
これら単量体(b3)は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
プロトン性極性基を有しない重合体は、上述した単量体(b1)および(b2)のうち少なくとも一種と、必要に応じて単量体(b3)とを任意に組み合わせて重合することによって得ることができる。
このような化合物の具体例としては、アクリル酸、メタクリル酸、アンゲリカ酸、チグリン酸、オレイン酸、エライジン酸、エルカ酸、ブラシジン酸、マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、アトロパ酸、ケイ皮酸等の不飽和カルボン酸;アリルアルコール、メチルビニルメタノール、クロチルアルコール、メタリルアルコール、1−フェニルエテン−1−オール、2−プロペン−1−オール、3−ブテン−1−オール、3−ブテン−2−オール、3−メチル−3−ブテン−1−オール、3−メチル−2−ブテン−1−オール、2−メチル−3−ブテン−2−オール、2−メチル−3−ブテン−1−オール、4−ペンテン−1−オール、4−メチル−4−ぺンテン−1−オール、2−ヘキセン−1−オール等の不飽和アルコール;等が挙げられる。
これら変性剤を用いた重合体の変性反応は、常法に従えばよく、通常、ラジカル発生剤の存在下で行われる。
本発明で用いる不飽和基含有化合物(B)としては、炭素−炭素不飽和結合を含有する化合物であればよく、特に限定されないが、(メタ)アクリル酸〔アクリル酸および/またはメタクリル酸の意。以下、同様。〕、(メタ)アクリル酸エステル、芳香族ビニル化合物、ビニルエステル系化合物、ビニルエーテル系化合物、ビニルケトン系化合物、エポキシ基含有ビニル化合物等が挙げられる。これらのなかでも、本発明の効果をより一層顕著なものとすることができるという点より、(メタ)アクリル酸エステルが好ましい。
本発明で用いるラジカル発生型光重合開始剤(C)としては、光を照射することで、ラジカルを発生し、化学反応を引き起こす化合物であればよく、特に限定されないが、好ましくは、400nm以下の波長の光に対する感度を有し、400nm以下の波長の光、具体的には、紫外線や電子線等の放射線を照射した場合に、ラジカルを発生し、化学反応を引き起こす化合物であることが好ましい。
これらのなかでも、N,N−オクタメチレンビスアクリジン、およびエタノン,1−[9−エチル−6−(2−メチルベンゾイル) −9H−カルバゾール−3−イル]−,1−(o−アセチルオキシム)が好ましい。これらラジカル発生型光重合開始剤(C)は、単独でまたは2種類以上を組み合わせて使用することができる。
本発明のネガ型感光性樹脂組成物には、さらに、溶剤が含有されていてもよい。溶剤としては、特に限定されず、各種樹脂材料の溶剤として公知のもの、例えばアセトン、メチルエチルケトン、シクロペンタノン、2−ヘキサノン、3−ヘキサノン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、2−オクタノン、3−オクタノン、4−オクタノンなどの直鎖のケトン類;n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、シクロヘキサノールなどのアルコール類;エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジオキサンなどのエーテル類;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などのアルコールエーテル類;ギ酸プロピル、ギ酸ブチル、酢酸プロピル、酢酸ブチル、プロピオン酸メチル、プロピオン酸エチル、酪酸メチル、酪酸エチル、乳酸メチル、乳酸エチルなどのエステル類;セロソルブアセテート、メチルセロソルブアセテート、エチルセロソルブアセテート、プロピルセロソルブアセテート、ブチルセロソルブアセテートなどのセロソルブエステル類;プロピレングリコール、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、プロピレングリコールモノブチルエーテルなどのプロピレングリコール類;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ジメチルエーテル、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メチルエチルエーテルなどのジエチレングリコール類;γ−ブチロラクトン、γ−バレロラクトン、γ−カプロラクトン、γ−カプリロラクトンなどの飽和γ−ラクトン類;トリクロロエチレンなどのハロゲン化炭化水素類;トルエン、キシレンなどの芳香族炭化水素類;ジメチルアセトアミド、ジメチルホルムアミド、N−メチルアセトアミドなどの極性溶媒などが挙げられる。これらの溶剤は、単独でも2種以上を組み合わせて用いてもよい。溶剤の含有量は、環状オレフィン重合体(A)100重量部に対して、好ましくは10〜10000重量部、より好ましくは50〜5000重量部、さらに好ましくは100〜1000重量部の範囲である。なお、ネガ型感光性樹脂組成物に溶剤を含有させる場合には、溶剤は、通常、樹脂膜形成後に除去されることとなる。
これらの酸性基を有する化合物は、それぞれ単独でまたは2種以上を組み合わせて用いることができる。また、酸性基は熱潜在性でもよい。
酸性基としては、酸性の官能基であればよく、その具体例としては、スルホン酸基、リン酸基等の強酸性基;カルボキシ基、チオール基およびカルボキシメチレンチオ基等の弱酸性基;が挙げられる。これらの中でも、カルボキシ基、チオール基またはカルボキシメチレンチオ基が好ましく、カルボキシ基が特に好ましい。また、これらの酸性基の中でも、酸解離定数pKaが3.5以上5.0以下の範囲にあるものが好ましい。なお、酸性基が2つ以上ある場合は第一解離定数pKa1を酸解離定数とし、第一解離定数pKa1が上記範囲にあるものが好ましい。また、pKaは、希薄水溶液条件下で、酸解離定数Ka=[H3O+][B−]/[BH]を測定し、pKa=−logKaにしたがって、求められる。ここでBHは、有機酸を表し、B−は有機酸の共役塩基を表す。
なお、pKaの測定方法は、例えばpHメータを用いて水素イオン濃度を測定し、該当物質の濃度と水素イオン濃度から算出することができる。
このような置換基としては、アルキル基、アリール基等の炭化水素基のほか、ハロゲン原子;アルコキシ基、アリールオキシ基、アシルオキシ基、ヘテロ環オキシ基;アルキル基又はアリール基又は複素環基で置換されたアミノ基、アシルアミノ基、ウレイド基、スルファモイルアミノ基、アルコキシカルボニルアミノ基、アリールオキシカルボニルアミノ基;アルキルチオ基、アリールチオ基、ヘテロ環チオ基;等のプロトンを有しない極性基、これらのプロトンを有しない極性基で置換された炭化水素基、等を挙げることができる。
これらの中でも、得られる樹脂膜の密着性をより高めることができるという観点から、酸性基の数は、2つ以上であることが好ましく、3つが特に好ましい。
(R6)r−Si−(OR7)4−r (5)
また、上記式(6)中、pは0または1である。qは、2〜10の整数であり、R6、R7は、上記式(5)と同様である。
R6を構成する、炭素原子に直接結合した官能基を有していてもよい炭素数6〜20のアリール基の具体例としては、フェニル基、トルイル基、p−ヒドロキシフェニル基、1−(p−ヒドロキシフェニル)エチル基、2−(p−ヒドロキシフェニル)エチル基、4−ヒドロキシ−5−(p−ヒドロキシフェニルカルボニルオキシ)ペンチル基、ナフチル基などが挙げられる。
また、R6を構成する、炭素原子に直接結合した官能基を有していてもよい炭素数1〜10の不飽和脂肪族基の具体例としては、ビニル基、3−アクリロキシプロピル基、3−メタクリロキシプロピル基などが挙げられる。
テトラメトキシシラン、テトラエトキシシラン、テトラ−n−プロポキシシラン、テトラ−i−プロポキシシラン、テトラ−n−ブトキシシランなどのテトラアルコキシシラン類、
メチルトリメトキシシラン、メチルトリエトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、n−プロピルトリメトキシシラン、n-プロピルトリエトキシシラン、i−プロピルトリメトキシシラン、i−プロピルトリエトキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、n−ペンチルトリメトキシシラン、n−ヘキシルトリメトキシシラン、n−ヘプチルトリメトキシシラン、n−オクチルトリメトキシシラン、n−デシルトリメトキシシラン、p−スチリルトリメトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、シクロヘキシルトリメトキシシラン、シクロヘキシルトリメトキシシラン、シクロヘキシルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、3−クロロプロピルトリメトキシシラン、3−クロロプロピルトリエトキシシラン、3,3,3−トリフルオロプロピルトリメトキシシラン、3,3,3−トリフルオロプロピルトリエトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、N−2−(アミノエチル)−3−アミノプロピルトリメトキシシラン、N−フェニル−3−アミノプロピルトリメトキシシラン、2−ヒドロキシエチルトリメトキシシラン、2−ヒドロキシエチルトリエトキシシラン、2−ヒドロキシプロピルトリメトキシシラン、2−ヒドロキシプロピルトリエトキシシラン、3−ヒドロキシプロピルトリメトキシシラン、3−ヒドロキシプロピルトリエトキシシラン、3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、3−イソシアナートプロピルトリメトキシシラン、3−イソシアナートプロピルトリエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、3−(メタ)アクリルオキシプロピルトリメトキシシラン、3−(メタ)アクリルオキシプロピルトリエトキシシラン、3−ウレイドプロピルトリメトキシシラン、3−ウレイドプロピルトリエトキシシラン、3−エチル(トリメトキシシリルプロポキシメチル)オキセタン、3−エチル(トリエトキシシリルプロポキシメチル)オキセタン、3−トリエトキシシリル−N−(1,3−ジメチル−ブチリデン)プロピルアミン、ビス(トリエトキシシリルプロピル)テトラスルフィドなどのトリアルコキシシラン類、
ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジ−n−プロピルジメトキシシラン、ジ−n−プロピルジエトキシシラン、ジ−i−プロピルジメトキシシラン、ジ−i−プロピルジエトキシシラン、ジ−n−ブチルジメトキシシラン、ジ−n−ペンチルジメトキシシラン、ジ−n−ペンチルジエトキシシラン、ジ−n−ヘキシルジメトキシシラン、ジ−n−ヘキシルジエトキシシラン、ジ−n−へプチルジメトキシシラン、ジ−n−ヘプチルジエトキシシラン、ジ−n−オクチルジメトキシシラン、ジ−n−オクチルジエトキシシラン、ジ−n−シクロヘキシルジメトキシシラン、ジ−n−シクロヘキシルジエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、3−グリシドキシプロピルメチルジエトキシシラン、3−メタクリルオキシプロピルメチルジメトキシシラン、3−アクリルオキシプロピルメチルジメトキシシラン、3−メタクリルオキシプロピルメチルジエトキシシラン、3−アクリルオキシプロピルメチルジエトキシシラン、N−2−(アミノエチル)−3−アミノプロピルメチルジメトキシシランなどのジアルコキシシラン類の他、
メチルトリアセチルオキシシラン、ジメチルジアセチルオキシシラン等のケイ素原子含有化合物;
(アセトアルコキシアルミウムジイソプロピレート)等のアルミニウム原子含有化合物;
(テトラノルマルプロポキシジルコニウム、テトラノルマルブトキシジルコニウム、ジルコニウムテトラアセチルアセトネート、ジルコニウムトリブトキシアセチルアセトネート、ジルコニウムものブトキシアセチルアセトネートビス(エチルアセトアセテート)、ジルコニウムジブトキシビス(エチルアセトアセテート)、ジルコニウムテトラアセチルアセトネート、ジルコニウムトリブトキシステアレート)等のジルコニウム原子含有化合物;が挙げられる。
混合の方法は特に限定されないが、ネガ型感光性樹脂組成物を構成する各成分を溶剤に溶解または分散して得られる溶液または分散液を混合するのが好ましい。これにより、ネガ型感光性樹脂組成物は、溶液または分散液の形態で得られる。
本発明の樹脂膜は、上述した本発明のネガ型感光性樹脂組成物を用いて得ることができる。本発明の樹脂膜としては、上述した本発明のネガ型感光性樹脂組成物を基板上に形成させることによって得られるものが好ましい。
潜像パターンを有する樹脂膜に現像液を接触させる方法としては、例えば、パドル法、スプレー法、ディッピング法等の方法が用いられる。現像は、通常、0〜100℃、好ましくは5〜55℃、より好ましくは10〜30℃の範囲で、通常、30〜180秒間の範囲で適宜選択される。
本発明の電子部品は、上述した本発明の樹脂膜を備えてなる。本発明の電子部品としては、特に限定されないが、各種半導体デバイスが挙げられ、具体的には、アクティブマトリックス基板、有機EL素子基板、集積回路素子基板、および固体撮像素子基板などが挙げられる。
なお、各特性の定義および評価方法は、以下のとおりである。
ネガ型感光性樹脂組成物を、シリコンウエハ上にスピンコーターを用いて塗布した後、ホットプレートを用いて100℃で2分間プリベークして、2.5μmの膜を作製した。なお、作製した膜の膜厚(F1)を光学式顕微鏡(大日本スクリーン製造社製、ラムダエースVM‐1200)を用いて測定した。次いで、365nmにおける光強度が5mW/cm2である紫外線を、所望の時間にて照射し、露光処理を行った。その後、2.38重量%のテトラメチルアンモニウムヒドロキシド水溶液を用いて、23℃、60秒間現像処理を行うことにより、シリコンウエハ上に形成された樹脂膜を得た。その後、光学式膜厚計を用いて、現像処理後の膜の膜厚(F2)を測定した。そして、現像処理前の膜厚(F1)および現像処理後の膜厚(F2)から、「現像残膜率(%)=(F2/F1)×100」にしたがって、現像処理後における現像残膜率を算出し、下記の基準で評価した。なお、現像残膜率が高いほど、現像によるパターン形成性に優れるため、好ましい。
○:現像残膜率90%以上。
×:現像残膜率90%未満。
ネガ型感光性樹脂組成物を、コーニング社製のガラス基板( 商品名「Eagle XG」、コーニング社製)上に、スピンコーターを用いて塗布した後、ホットプレートを用いて100℃で2分間プリベークした。次いで、樹脂膜をパターニングするために、0.5μmから5.0μmまで大きさの異なるコンタクトホールパターン、および、10μm、25μm、50μmの各コンタクトホールパターンを形成可能なマスクを用い、365nmにおける光強度が5mW/cm2である紫外線を、所望の時間にて照射することで、露光処理を行った。その後、2.38重量%のテトラメチルアンモニウムヒドロキシド水溶液を用いて、23℃、60秒間現像処理を行い、コンタクトホールパターンを有する樹脂膜とガラス基板とからなる積層体を得た。
そして、得られた積層体の樹脂膜について、走査型電子顕微鏡(SEM)を用いて、コンタクトホール内における、溶解残渣の有無を確認し、下記の基準で評価した。なお、溶解残渣が観測されない方が、現像によるパターン形成性に優れるため、好ましい。
○:現像残渣が観察されなかった。
×:現像残渣が観察された。
上記現像残渣の評価と同様にして、ネガ型感光性樹脂組成物を用いて、樹脂膜を得て、同様にして、露光および現像を行い、コンタクトホールパターンを有する樹脂膜とガラス基板とからなる積層体を得て、得られた積層体について、クリーンオーブンを用いて、窒素雰囲気中にて230℃で1時間加熱処理を行なった。そして、加熱後の積層体の樹脂膜について、分光光度計(日本分光株式会社製、紫外可視分光光度計V560)を用いて、波長400nmでの透過率測定を行い、2μmの膜厚に換算した場合における透過率を算出し、下記の基準で評価を行った。
◎:透過率が80%以上、100%以下。
○:透過率が75%以上、80%未満。
△:透過率が70%以上、75%未満。
×:透過率が70%未満。
上記現像残渣の評価と同様にして、ネガ型感光性樹脂組成物を用いて、樹脂膜を得て、同様にして、露光および現像を行い、コンタクトホールパターンを有する樹脂膜とガラス基板とからなる積層体を得た。そして、得られた積層体の樹脂膜について、光学顕微鏡を用いて、5μmのコンタクトホールパターンの最長部の長さ(L1)を測定した。次いで、得られた積層体について、クリーンオーブンを用いて、窒素雰囲気中にて230℃で1時間加熱処理を行なった。その後、光学顕微鏡を用いて、加熱後の積層体の樹脂膜を観察し、加熱前に観察したコンタクトホールパターンについて、最長部の長さ(L2)を測定し、加熱処理前の最長部の長さ(L1)および加熱処理後の最長部の長さ(L2)から、「パターン保持率(%)=(L2/L1)×100」にしたがって、加熱後のパターン保持率を算出し、下記の基準で評価した。なお、加熱後のパターン保持率が高いほど、耐熱性に優れるため、好ましい。
○:パターン保持率が80%以上。
×:パターン保持率が80%未満。
上記現像残膜の評価と同様にして、ネガ型感光性樹脂組成物を用いて、同様にして、スピンコート、露光および現像を行い、シリコンウエハ上に形成された樹脂膜を得た。そして、得られた樹脂膜について、クリーンオーブンを用いて、窒素雰囲気中にて230℃ で1時間加熱処理を行なった。その後、加熱後の樹脂膜を、昇温脱離分析装置(電子科学社製、WA1000S/W型)を用いて、220℃、30分間加熱し、その時脱離する原子量18(水)の成分の量からアウトガス量を算出し、下記の基準で評価を行った。
◎:アウトガス量が10ppm未満。
○:アウトガス量が10ppm以上、20ppm未満。
△:アウトガス量が20ppm以上、30ppm未満。
×:アウトガス量が30ppm以上。
<環状オレフィン重合体(A−1)の調製>
9−ヒドロキシカルボニルテトラシクロ[6.2.1.13,6.02,7]ドデカ−4−エン60.0部、N−フェニルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド(NBPI)40.0部、1,5−ヘキサジエン2.8部、(1,3−ジメシチルイミダゾリジン−2−イリデン)(トリシクロヘキシルホスフィン)ベンジリデンルテニウムジクロリド0.05部、およびジエチレングリコールエチルメチルエーテル400部を、窒素置換した耐圧ガラス反応器に仕込み、撹拌しつつ80℃で4時間重合反応を行って開環メタセシス重合体を含有する重合反応溶液を得た。
<環状オレフィン重合体(A−2)の調製>
N−フェニルビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド(NBPI)40.0部の代わりに、N−(2−エチルヘキシル)−ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド(NEHI)40.0部を使用し、1,5‐ヘキサジエンの使用量を2.8部から2.0部に変更した以外は、合成例1と同様にして、重合および水素化を行い、環状オレフィン重合体(A−2)を含む重合体溶液を得た。得られた環状オレフィン重合体(A−2)の重合転化率は99.7%、重量平均分子量は7,150、数平均分子量は4,690、分子量分布は1.52、水素添加率は99.9%であった。
<環状オレフィン重合体(A−3)の調製>
9−ヒドロキシカルボニルテトラシクロ[6.2.1.13,6.02,7]ドデカ−4−エンの使用量を60.0部から65.0部に、N−(2−エチルヘキシル)−ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミドの使用量を40.0部から35.0部に、それぞれ変更した以外は、合成例2と同様にして、重合および水素化を行い、環状オレフィン重合体(A−3)を含む重合体溶液を得た。得られた環状オレフィン重合体(A−3)の重合転化率は99.5%、重量平均分子量は5,670、数平均分子量は3,520、分子量分布は1.61、水素添加率は99.9%であった。
<環状オレフィン重合体(A−4)の調製>
9 − ヒドロキシカルボニルテトラシクロ[6.2.1.13,6.02,7]ドデカ‐4‐エン(TCDC)5部、8−エチル−テトラシクロ[4.4.0.12,5.17,1,0]ドデカ−3−エン(ETD)95部、1,5−ヘキサジエン2.0部、(1,3−ジメシチルイミダゾリジン−2−イリデン)(トリシクロヘキシルホスフィン)ベンジリデンルテニウムジクロリド0.05部、およびデカリン400部を、窒素置換した耐圧ガラス反応器に仕込み、攪拌しつつ80℃で4時間重合反応を行って開環メタセシス重合体を含有する重合反応溶液を得た。
<ポリイミド(A’−5)の調製>
乾燥空気気流下、4つ口フラスコ内で4,4’−ジアミノジフェニルエーテル9.61部、ビス[4−(4−アミノフェノキシ)フェニル]スルホン17.3部、ビス(3−アミノプロピル)テトラメチルジシロキサン1.24部、およびシクロペンタノン102.5部を仕込み、40℃で溶解させた。その後、無水ピロメリット酸6.54部、3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物9.67部、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12.41部、およびシクロペンタノン30部を加え、50℃で3時間反応させた。この溶液をロータリーエバポレーターで濃縮し、固形分濃度35%のポリイミド(A’−5)を含む重合体溶液を得た。
合成例1で得られた環状オレフィン重合体(A−1)100部(固形分換算)、不飽和基含有化合物(B)として、ジシクロペンテニルアクリレート(製品名「FA−511AS」、日立化成社製、単官能アクリレート)50部、ジエチレングリコールジメタクリレート(製品名「2G」、新中村化学工業社製、2官能メタクリレート)30部、ラジカル発生型光重合開始剤(C)として、1,7−ビス(9−アクリジル)−ヘプタン(商品名「N1717」、ADEKA社製)10部、有機溶剤として、ジエチレングリコールエチルメチルエーテルを、固形部濃度が40%となるように添加して混合攪拌し、溶解させた後、溶液を孔径0.45μmのポリテトラフルオロエチレン製フィルターでろ過して、ネガ型感光性樹脂組成物を調製した。
ジエチレングリコールジメタクリレート30部の代わりに、ジペンタエリスリトールヘキサアクリレート(たとえば、製品名「DPHA」、ダイセル・サイテック社製)10部を用いた以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジエチレングリコールジメタクリレート30部の代わりに、トリメチロールプロパントリメタクリレート(製品名「TMPT」、新中村化学工業社製)10部を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジエチレングリコールジメタクリレート30部の代わりに、ネオペンチルグリコールジアクリレート(製品名「ライトアクリレートNP−A」、共栄化学社製)30部を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジエチレングリコールジメタクリレート30部の代わりに、ベンジルメタクリレート(製品名「FA−BZM」、日立化成社製)10部を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
合成例1で得られた環状オレフィン重合体(A−1)100部(固形分換算)の代わりに、合成例2で得られた環状オレフィン重合体(A−2)60部(固形分換算)および合成例3で得られた環状オレフィン重合体(A−3)40部(固形分換算)を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部、およびジエチレングリコールジメタクリレート30部の代わりに、ベンジルメタクリレート50部およびトリメチロールプロパントリメタクリレート10部を使用した以外は、実施例6と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部の代わりに、ベンジルメタクリレート50部を使用するとともに、ジエチレングリコールジメタクリレートの配合量を30部から50部に変更した以外は、実施例6と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
合成例1で得られた環状オレフィン重合体(A−1)100部(固形分換算)の代わりに、合成例4で得られた環状オレフィン重合体(A−4)100部(固形分換算)を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部、およびジエチレングリコールジメタクリレート30部の代わりに、ベンジルメタクリレート50部およびトリメチロールプロパントリメタクリレート10部を使用した以外は、実施例9と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
1,7−ビス(9−アクリジル)−ヘプタンの配合量を10部から5部に変更し、かつ、ラジカル発生型光重合開始剤(D)としてのエタノン,1−[9−エチル−6−(2−メチルベンゾイル) −9H−カルバゾール−3−イル]−,1−(o−アセチルオキシム)(製品名「OXE−02」、BASF社製)5部をさらに配合した以外は、実施例9と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部、およびジエチレングリコールジメタクリレート30部の代わりに、ジペンタエリスリトールヘキサアクリレート20部を使用した以外は、実施例9と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部、およびジエチレングリコールジメタクリレート30部を配合しなかった以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部、およびジエチレングリコールジメタクリレート30部を配合しなかった以外は、実施例6と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
ジシクロペンテニルアクリレート50部、およびジエチレングリコールジメタクリレート30部を配合しなかった以外は、実施例9と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
1,7−ビス(9−アクリジル)−ヘプタン10部の代わりに、カチオン発生型光重合開始剤(ADEKA社製、アデカオプトマーSP300)10部を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
1,7−ビス(9−アクリジル)−ヘプタン10部を配合しなかった以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
1,7−ビス(9−アクリジル)−ヘプタン10部を配合しなかった以外は、実施例6と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
1,7−ビス(9−アクリジル)−ヘプタン10部を配合しなかった以外は、実施例9と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
合成例1で得られた環状オレフィン重合体(A−1)100部(固形分換算)の代わりに、合成例5で得られたポリイミド(A’−5)100部(固形分換算)を使用した以外は、実施例1と同様にして、ネガ型感光性樹脂組成物を調製し、同様に評価を行った。結果を表1に示す。
また、プロトン性極性基を有する環状オレフィン重合体(A)の代わりに、ポリイミドを使用した比較例8においては、得られる樹脂膜は耐熱透明性および低アウトガス性に劣るものであった。
Claims (4)
- プロトン性極性基を有する環状オレフィン重合体(A)、不飽和基含有化合物(B)、およびラジカル発生型光重合開始剤(C)を含有してなり、
前記不飽和基含有化合物(B)が、ジシクロペンテニルアクリレートおよびベンジルメタクリレートから選択される少なくとも1種の単官能の(メタ)アクリレートと、ジペンタエリスリトールヘキサアクリレートおよびトリメチロールプロパントリメタクリレートから選択される少なくとも1種の3官能以上の多官能(メタ)アクリレートとの組み合わせであるネガ型感光性樹脂組成物。 - 前記不飽和基含有化合物(B)の含有量が、前記プロトン性極性基を有する環状オレフィン重合体(A)100重量部に対して、好ましくは20〜150重量部である請求項1に記載のネガ型感光性樹脂組成物。
- 請求項1または2に記載のネガ型感光性樹脂組成物を用いて得られる樹脂膜。
- 請求項3に記載の樹脂膜を備える電子部品。
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