JPWO2020031958A1 - 感光性樹脂組成物、感光性シート、ならびにそれらの硬化膜およびその製造方法、電子部品 - Google Patents
感光性樹脂組成物、感光性シート、ならびにそれらの硬化膜およびその製造方法、電子部品 Download PDFInfo
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- JPWO2020031958A1 JPWO2020031958A1 JP2019543402A JP2019543402A JPWO2020031958A1 JP WO2020031958 A1 JPWO2020031958 A1 JP WO2020031958A1 JP 2019543402 A JP2019543402 A JP 2019543402A JP 2019543402 A JP2019543402 A JP 2019543402A JP WO2020031958 A1 JPWO2020031958 A1 JP WO2020031958A1
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
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- 239000011347 resin Substances 0.000 claims abstract description 70
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- 229920000647 polyepoxide Polymers 0.000 claims abstract description 15
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 13
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
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- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
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- 125000005843 halogen group Chemical group 0.000 claims description 14
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
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- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 6
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- 125000002541 furyl group Chemical group 0.000 claims description 3
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 16
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- 238000000576 coating method Methods 0.000 description 15
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 12
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- 239000007983 Tris buffer Substances 0.000 description 11
- 229940116333 ethyl lactate Drugs 0.000 description 11
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 238000006116 polymerization reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
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- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 6
- OZUCXGWYZVDFOU-UHFFFAOYSA-N 2-(diethylamino)ethyl 6-hydroxy-4,7-dimethoxy-1-benzofuran-5-carboxylate;hydrochloride Chemical compound [Cl-].CC[NH+](CC)CCOC(=O)C1=C(O)C(OC)=C2OC=CC2=C1OC OZUCXGWYZVDFOU-UHFFFAOYSA-N 0.000 description 5
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 5
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 5
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- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
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- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- FVMMYGUCXRZVPJ-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)OCC1CO1 FVMMYGUCXRZVPJ-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-UHFFFAOYSA-N 0.000 description 1
- PSUKBUSXHYKMLU-UHFFFAOYSA-N triethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OCC)(OCC)OCC)CCC2OC21 PSUKBUSXHYKMLU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 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
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- KKFKPRKYSBTUDV-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CC(CC)OCC1CO1 KKFKPRKYSBTUDV-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- CESKYMDZTHKIPO-UHFFFAOYSA-N tris(2-methoxyethoxy)-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound COCCO[Si](OCCOC)(OCCOC)CCCOCC1CO1 CESKYMDZTHKIPO-UHFFFAOYSA-N 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
ここで、酸成分はテトラカルボン酸又はテトラカルボン酸二無水物若しくはテトラカルボン酸ジエステルジクロリドなどが挙げられる。ジアミン成分はジアミン又はジイソシアネート化合物若しくはトリメチルシリル化ジアミンなどが挙げられる。
ジケトン化合物としては、ベンジルが挙げられる。
ケトエステル化合物としては、ベンゾイルギ酸メチル、ベンゾイルギ酸エチルが挙げられる。
(A)樹脂の重量平均分子量(Mw)は、GPC(ゲルパーミエーションクロマトグラフィー)装置Waters2690−996(日本ウォーターズ(株)製)を用いて確認した。展開溶媒をN−メチル−2−ピロリドン(以降NMPと呼ぶ)として測定し、ポリスチレン換算で重量平均分子量(Mw)及び分散度(PDI=Mw/Mn)を計算した。
(2)−1 感度A
各実施例および比較例により得られた,ポリイミド系樹脂およびエポキシ樹脂を用いたワニスをシリコンウエハにスピンコーター(ミカサ(株)製1H−360S)を用いてスピンコートした後、ホットプレート(大日本スクリーン製造(株)製SCW−636)を用いて120℃で3分間プリベークし、膜厚11μmのプリベーク膜を作製した。得られたプリベーク膜に、パラレルライトマスクアライナー(以下PLAという)(キヤノン(株)製PLA−501F)を用いて超高圧水銀灯を光源(g線、h線、i線の混合線)として、感度測定用のグレースケールマスク(2〜50μmの、1:1のライン&スペースのパターンを有する。それぞれ、1%、5%、10%、12%、14%、16%、18%、20%、22%、25%、30%、35%、40%、50%および60%の透過率となるエリアを有する。)を介してコンタクトで露光した。その後、ワニスがネガ型の場合は120℃で1分間露光後ベークをし、塗布現像装置MARK−7を用いて現像を行った。ポリマーがアルカリ水溶液に溶解しない場合は現像液としてシクロペンタノンを用いて2分間シャワー現像し、ついでプロピレングリコールモノメチルエーテルアセテートで30秒間リンスした。ポリマーがアルカリ水溶液に溶解する場合は、現像液として2.38質量%水酸化テトラメチルアンモニウム(以下、「TMAH」と略す)水溶液(商品名「ELM−D」、三菱ガス化学(株)製)で90秒間パドル現像し、次いで水で30秒間リンスした。
なお、膜厚は大日本スクリーン製造(株)製ラムダエースSTM−602を用いて屈折率1.629で測定した。以下に記載する膜厚も同様である。
スピンコーターを用いて、各実施例および比較例により得られたポリシロキサンを用いたワニスを、10cm角の無アルカリガラス基板上に、スピンコートし、ホットプレートを用いて、温度90℃で2分間プリベークし、膜厚2μmのプリベーク膜を作製した。
なお、膜厚は大日本スクリーン製造(株)製ラムダエースSTM−602を用いて屈折率1.550で測定した。以下に記載する膜厚も同様である。
(2)−1で定義した感度Aでの露光量における現像後の最小パターン寸法を測定した。
(2)−2で定義した感度Bでの露光量における現像後の最小パターン寸法を測定した。
(3)−1 耐薬品性評価A
各実施例および比較例により得られた,ポリイミド系樹脂およびエポキシ樹脂を用いたワニスを、シリコンウエハ上に120℃で3分間プリベークを行った後の膜厚が10μmとなるように塗布現像装置MARK−7を用いてスピンコート法で塗布し、プリベークした後、ネガ型の場合はPLA−501Fを用いて全面に300mJ/cm2を露光し、ポジ型の場合はそのまま、イナートオーブンCLH−21CD−S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180℃まで昇温し、それぞれの温度で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シリコンウエハを取り出し、その硬化膜を有機薬液(ジメチルスルホキシド:25質量%TMAH水溶液=92:2)に40℃で10分間浸漬させ、パターンの剥がれや膜厚の変化(膨潤または溶出量を示す)を観察した。その結果が、パターンの剥がれ無く、膜厚変化が5%以下のものを4、パターンの剥がれ無く、膜厚変化5%を超えて10%以下を3、パターンの剥がれ無く、膜厚変化が10%を超えて30%以下を2、パターンが剥がれ膜が残らない場合や膜厚変化が30%を超えるものを1として、評価した。
パターンの剥がれが無く、膜厚変化が小さいものほど良好な耐薬品性を示す。
各実施例および比較例により得られたポリシロキサンを用いたワニスを、スピンコーターを用いて、表面にITOをスパッタリングしたガラス基板(以下、「ITO基板」という)上にスピンコートし、ホットプレート(商品名SCW−636、大日本スクリーン製造(株)製)を用いて100℃で2分間プリベークし、膜厚2.0μmの膜を作製した。
各実施例および比較例により得られた,ポリイミドおよびエポキシ樹脂を用いたワニスを6インチのシリコンウエハ上に、120℃で3分間のプリベーク後の膜厚が11μmとなるように塗布現像装置ACT−8を用いてスピンコート法で塗布およびプリベークした後、ネガ型の場合はPLAを用いて全面に300mJ/cm2を露光し、ポジ型の場合はそのままイナートオーブンCLH−21CD−S(光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で3.5℃/分で180℃まで昇温し、それぞれの温度で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シリコンウエハを取り出し、45質量%のフッ化水素酸に5分間浸漬することで、ウエハより樹脂組成物の硬化膜を剥がした。この膜を幅1.5cm、長さ9cmの短冊状に切断し、テンシロンRTM−100((株)オリエンテック製)を用いて、室温23.0℃、湿度45.0%RH下で引張速度50mm/分で引っ張り(チャック間隔=2cm)、破断点伸度(%)および破断点強度(MPa)の測定を行なった。測定は1検体につき10枚の短冊について行ない、結果から数値の高い上位5点の平均値を求めた(有効数字=2桁)。この評価は、ポリイミド、およびエポキシ樹脂の機械特性評価として実施した。
(5)−1 銅基板密着性評価A
次の方法にて金属銅との密着性評価を行なった。
銅基板上に、前記(3)−2記載の方法と同様にして膜厚2.0μmの硬化膜を形成した。得られた基板を2分割し、それぞれの基板についてキュア後の膜に片刃を使用して2mm間隔で10行10列の碁盤目状の切り込みをいれた。このうち一方のサンプル基板を用い、“セロテープ”(登録商標)による引き剥がしによって100マスのうち何マス剥がれたかで金属材料/樹脂硬化膜間の接着特性の評価を行なった。また、もう一方のサンプル基板については、プレッシャークッカー試験(PCT)装置(タバイエスペエック(株)製HAST CHAMBER EHS−211MD)を用いて85℃、85%の条件で25時間PCT処理を行なった後、上記の引き剥がしテストを行なった。密着性の判定は、前記(5)−1 銅基板密着性評価Aと同様に行った。
硬化膜のイミド化率(%)は、以下の方法で容易に求めることができる。(4)と同じ手順で加熱処理まで行いシリコンウエハ上に硬化膜を作製した。次に作製した硬化膜の赤外吸収スペクトルを測定し(シリコンウエハをベースラインとする)、ポリイミドに起因するイミド構造の吸収ピーク(1780cm−1付近、1377cm−1付近)の存在を確認し、1377cm−1付近のピーク強度(X)を求める。次に、その硬化膜を350℃で1時間熱処理し、赤外吸収スペクトルを測定し、1377cm−1付近のピーク強度(Y)を求める。これらのピーク強度比が熱処理前ポリマー中のイミド基の含量、すなわちイミド化率に相当する(イミド化率=X/Y×100(%))。
調製後のワニスの粘度および23℃下で2週間放置した後の粘度を測定し、放置前後の粘度の変化率を計算した。
ITO基板上に、前記(3)−2記載の方法と同様にして得られた膜厚2.0μmの硬化膜を形成した。得られた硬化膜について、JIS「K5600−5−4(制定年月日=1999/04/20)」に準拠して鉛筆硬度を測定した。この評価は、ポリシロキサンの機械特性評価として実施した。
(4)と同様の手順で硬化膜の自立膜を作製し、この膜を3.0cm×0.5cmになるように片刃で切り出し、示差走査熱量計(セイコーインスツル製、TMA/SS6100)を用いて窒素気流下80mL/min条件下において、10℃/minの速度で25℃から400℃まで昇温し、測定した。50℃から150℃における線膨張係数をCTE(10−6/K)として算出した。
4,4’−オキシジフタル酸二無水物(ODPA)31.02g(0.10mol)を500ml容量のセパラブルフラスコに入れ、2−ヒドロキシエチルメタクリレート(HEMA)を26.03g(0.20mol)とγ―ブチロラクトン76mlを入れて室温下で、撹拌しながらピリジン16.22g(0.21mol)を加えて反応混合物を得た。反応による発熱の終了後に室温まで放冷し、16時間放置した。
乾燥窒素気流下、ODPA62.04g(0.2モル)をNMP1000gに溶解させた。ここに下記構造のジアミン(HA)96.72g(0.16モル)と1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン(SiDA)4.97g(0.02モル)をNMP100gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。次に末端封止剤として3−アミノフェノール(MAP)4.37g(0.04モル)をNMP30gとともに加え、50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール47.66g(0.4モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水1Lに投入して沈殿を得た。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、ポリイミド前駆体樹脂(P−2)の粉末を得た。ポリイミド前駆体(P−1)の分子量をゲルパーミエーションクロマトグラフィー(標準ポリスチレン換算)で測定したところ、重量平均分子量(Mw)は25000、PDIは2.3であった。ポリイミド前駆体(P−2)はアルカリ水溶液に可溶であり、これを用いた感光性樹脂組成物は2.38質量%TMAH水溶液で現像される。
ODPAに替えてビフェニルテトラカルボン酸無水物(BPDA)29.42gを用いた以外は、合成例1と同様に実施し、ポリイミド前駆体(P−3)を得た。ポリイミド前駆体(P−3)のMwは34000、PDIは2.5であった。ポリイミド前駆体(P−3)はシクロペンタノンで現像される。
DAE18.62gに替えて、DAE18.03g(0.090mol)および1,3,5−トリス(4−アミノフェノキシ)ベンゼン(TAPOB)0.80g(0.002mol)を用いた以外は、合成例1と同様に実施し、ポリイミド前駆体(P−4)を得た。ポリイミド前駆体(P−4)のMwは27000、PDIは2.9であった。ポリイミド前駆体(P−4)はシクロペンタノンで現像される。
500mlの三口フラスコに、p−スチリルトリメトキシシラン(St)を43.74g(0.195mol)、γ−アクリロイルプロピルトリメトキシシラン(Acry)を14.06g(0.06mol)、3−トリメトキシシリルプロピルコハク酸無水物(Suc)を11.80g(0.045mol)、TBCを0.173g、PGMEを74.58g仕込み、室温で撹拌しながら、水17.01gにリン酸0.348g(仕込みモノマーに対して0.50質量%)を溶かしたリン酸水溶液を30分間かけて添加した。その後、三口フラスコを70℃のオイルバスに浸けて90分間撹拌した後、オイルバスを30分間かけて115℃まで昇温した。昇温開始1時間後に三口フラスコの内温(溶液温度)が100℃に到達し、そこから2時間加熱撹拌し(内温は100〜110℃)、ポリシロキサン溶液を得た。なお、昇温および加熱撹拌中、窒素を0.05リットル/分流した。反応中に、副生成物であるメタノールおよび水が合計36.90g留出した。得られたポリシロキサン溶液に、固形分濃度が40質量%となるようにPGMEを追加し、ポリシロキサン(P−5)溶液を得た。
500mlの三口フラスコに、p−スチリルトリメトキシシラン(St)を44.86g(0.200mol)、フェニルトリメトキシシラン(Ph)を39.66g(0.200mol)、メチルトリメトキシシラン(Me)6.81g(0.050mol)、3−トリメトキシシリルプロピルコハク酸無水物(Suc)を13.12g(0.050mol)、TBCを0.522g、PGMEを74.58g仕込み、室温で撹拌しながら、水27.90gにリン酸0.448g(仕込みモノマーに対して0.50質量%)を溶かしたリン酸水溶液を30分間かけて添加した。その後、三口フラスコを70℃のオイルバスに浸けて90分間撹拌した後、オイルバスを30分間かけて115℃まで昇温した。昇温開始1時間後に三口フラスコの内温(溶液温度)が100℃に到達し、そこから2時間加熱撹拌し(内温は100〜110℃)、ポリシロキサン溶液を得た。なお、昇温および加熱撹拌中、窒素を0.05リットル/分流した。反応中に、副生成物であるメタノールおよび水が合計58.90g留出した。得られたポリシロキサン溶液に、固形分濃度が40質量%となるようにPGMEを追加し、ポリシロキサン(P−6)溶液を得た。
黄色灯下にて、ポリイミド前駆体(P−1)10.00g、1,2−オクタンジオン,1−[4−(フェニルチオ)−2−(O−ベンゾイルオキシム)](「イルガキュアOXE−01(商品名)」BASF製)0.50g、B−I0.30g、NKエステル 4G(商品名)(新中村化学工業(株)製、化学名:テトラエチレングリコールジメタクリレート)2.00g、N−フェニルジエタノールアミン0.2g、3−トリメトキシシリルフタルアミド酸0.30gを、N−メチルピロリドン(NMP)15.15gおよび乳酸エチル(EL)3.81gに溶解させ、アクリル系界面活性剤である「ポリフロー77(商品名)」(共栄社化学(株)製)の1質量%EL溶液0.10gを加え、撹拌してワニスを得た。得られたワニスの特性を上記評価方法により、パターン加工性(感度A、現像性A)、耐薬品性A、破断点伸度、破断点強度、熱線膨張係数、銅基板密着性評価A、イミド化率測定および保存安定性を測定した。
[実施例2]
B−IをB−IIに替えた以外は、実施例1と同様に実施した。
[実施例3]
B−IをB−IIIに替えた以外は、実施例1と同様に実施した。
[実施例4]
B−IをB−IVに替えた以外は、実施例1と同様に実施した。
[実施例5]
B−IをB−Vに替えた以外は、実施例1と同様に実施した。
[実施例6]
B−IをB−VIに替えた以外は、実施例1と同様に実施した。
B−IをB−VIIに替えた以外は、実施例1と同様に実施した。
[実施例8]
B−IをB−VIIIに替えた以外は、実施例1と同様に実施した。
[実施例9]
B−IをB−IXに替えた以外は、実施例1と同様に実施した。
[実施例10]
P−1をP−3に替えた以外は、実施例3と同様に実施した。
[実施例11]
P−1をP−4に替えた以外は、実施例3と同様に実施した。
B−IIIの添加量を0.01gとした以外は、実施例3と同様に実施した。
[実施例13]
B−IIIの添加量を0.03gとした以外は、実施例3と同様に実施した。
[実施例14]
B−IIIの添加量を0.7gとした以外は、実施例3と同様に実施した。
[実施例15]
B−IIIの添加量を1.0gとした以外は、実施例3と同様に実施した。
[実施例16]
B−IIIの添加量を2.0gとした以外は、実施例3と同様に実施した。
[実施例17]
黄色灯下にて、ポリイミド前駆体(P−1)10.00g、2−(ジメチルアミノ)−2−[(4−メチルフェニル)メチル]−1−[4−(4−モルホリニル)フェニル]−1−ブタノン(「イルガキュア379(商品名)」BASF製)0.80g、ジエチルチオキサントン0.2g、B−III0.30g、4G2.00g、N−フェニルジエタノールアミン0.2g、3−トリメトキシシリルフタルアミド酸0.30gを、NMP15.15gおよびEL3.81gに溶解させ、ポリフロー77の1質量%EL溶液0.10gを加え、撹拌してワニスを得た。得られたワニスの特性を上記評価方法により、パターン加工性(感度A、現像性A)、耐薬品性A、破断点伸度、破断点強度、熱線膨張係数、銅基板密着性評価A、イミド化率測定および保存安定性を測定した。
イルガキュア379をビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド(「イルガキュア819(商品名)」BASF製)に替えた以外は実施例17と同様に実施した。
[実施例19]
イルガキュア379を2−ヒロドキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]フェニル}−2−メチル−プロパン−1−オン(「イルガキュア127(商品名)」BASF製)に替えた以外は実施例17と同様に実施した。
[実施例20]
イルガキュア379をp−ジメチルアミノ安息香酸エチルに替えた以外は実施例17と同様に実施した。
[実施例21]
イルガキュア379を4−フェニルベンゾフェノンに替えた以外は、実施例17と同様に実施した。
[実施例22]
ポリイミド前駆体(P−1)の代わりに、クレゾールノボラック型多官能エポキシ樹脂である固形多官能芳香族エポキシ樹脂(YDCN−700−10(商品名)、新日鉄住金化学社製)を用い、さらにジペンタエリスリトールヘキサアクリレート(DPHA(商品名)、日本化薬製)を2g添加した以外は、実施例1と同様に実施した。ただし、イミド化率だけは測定しなかった。
黄色灯下にて、ポリイミド前駆体(P−2)10.00g、TP5−280M(東洋合成製;TrisP−PA(本州化学製)の5−ナフトキノンジアジドスルホン酸エステル化合物)2.0g、B−I0.2gを、NMP14.5gに溶解させ、ポリフロー77の1wt%NMP溶液0.10gを加え、撹拌してワニスを得た。得られたワニスの特性を上記評価方法により測定した。
[実施例24]
B−IをB−IIに替えた以外は、実施例23と同様に実施した。
[実施例25]
B−IをB−IIIに替えた以外は、実施例23と同様に実施した。
[実施例26]
B−IをB−IVに替えた以外は、実施例23と同様に実施した。
[実施例27]
B−IをB−Vに替えた以外は、実施例23と同様に実施した。
[実施例28]
B−IをB−VIに替えた以外は、実施例23と同様に実施した。
[実施例29]
B−IをB−VIIに替えた以外は、実施例23と同様に実施した。
[実施例30]
B−IをB−VIIIに替えた以外は、実施例23と同様に実施した。
[実施例31]
B−IをB−IXに替えた以外は、実施例23と同様に実施した。
[実施例32]
B−IIIの添加量を0.01gとした以外は、実施例25と同様に実施した。
[実施例33]
B−IIIの添加量を0.03gとした以外は、実施例25と同様に実施した。
[実施例34]
B−IIIの添加量を0.7gとした以外は、実施例25と同様に実施した。
[実施例35]
B−IIIの添加量を1.0gとした以外は、実施例25と同様に実施した。
[実施例36]
B−IIIの添加量を1.5gとした以外は、実施例25と同様に実施した。
黄色灯下にて、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)(“イルガキュア”(登録商標)OXE−02(商品名)、BASFジャパン(株)製)0.080gおよびビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド(“イルガキュア”(登録商標)−819(商品名)、BASFジャパン(株)製)0.160g、エチレンビス(オキシエチレン)ビス[3−(5−tert−ブチル−4−ヒドロキシ−m−トリル)プロピオネート](“イルガノックス”(登録商標)−245(商品名)、BASFジャパン(株)製)のPGME10質量%溶液0.200g、ペンタエリスリトールアクリレート(“ライトアクリレート”(登録商標)PE−3A(商品名)、共栄社化学(株)製)0.800g、B−I0.16g、3−メタクリロキシプロピルトリメトキシシラ(KBM−503(商品名)、信越化学(株)製)0.120gを、PGME8.615gとPGMEA3.200gの混合溶剤に溶解させ、シリコーン系界面活性剤(商品名“BYK”(登録商標)−333、ビックケミー・ジャパン(株)製)のPGME10質量%希釈溶液0.020g(濃度100ppmに相当)を加え、撹拌した。その後、(A)ポリシロキサンとして、ポリシロキサン(P−5)溶液6.645g、次いで0.45μmのフィルターでろ過を行い、ポリシロキサン含有のワニスを得た。得られたワニスについて、前述に記載した、感度B、現像性B、耐薬品性B、硬度、銅基板密着性B、保存安定性をそれぞれ評価した。
[実施例38]
B−IをB−IIに替えた以外は、実施例37と同様に実施した。
[実施例39]
B−IをB−IIIに替えた以外は、実施例37と同様に実施した。
B−IをB−IVに替えた以外は、実施例37と同様に実施した。
[実施例41]
B−IをB−Vに替えた以外は、実施例37と同様に実施した。
[実施例42]
B−IをB−VIに替えた以外は、実施例37と同様に実施した。
[実施例43]
B−IをB−VIIに替えた以外は、実施例37と同様に実施した。
[実施例44]
B−IをB−VIIIに替えた以外は、実施例37と同様に実施した。
[実施例45]
B−IをB−IXに替えた以外は、実施例37と同様に実施した。
黄色灯下にて、TP5−280M(東洋合成製;TrisP−PA(本州化学製)の5−ナフトキノンジアジドスルホン酸エステル化合物)0.240g、B−I0.160g、3−メタクリロキシプロピルトリメトキシシラン(KBM−503(商品名)、信越化学(株)製)0.120gおよび、PGME7.565gとPGMEA3.200gの混合溶剤に溶解させ、シリコーン系界面活性剤(商品名“BYK”(登録商標)−333、ビックケミー・ジャパン(株)製)のPGME10質量%希釈溶液0.020g(濃度100ppmに相当)を加え、撹拌した。その後、(A)ポリシロキサンとして、ポリシロキサン(P−6)溶液8.695g、次いで0.45μmのフィルターでろ過を行い、ワニスを得た。得られたワニスについて、前述に記載した、感度B、現像性B、耐薬品性B、硬度、銅基板密着性B、保存安定性をそれぞれ評価した。
[実施例47]
B−IをB−IIに替えた以外は、実施例46と同様に実施した。
[実施例48]
B−IをB−IIIに替えた以外は、実施例46と同様に実施した。
[実施例49]
B−IをB−IVに替えた以外は、実施例46と同様に実施した。
[実施例50]
B−IをB−Vに替えた以外は、実施例46と同様に実施した。
[実施例51]
B−IをB−VIに替えた以外は、実施例46と同様に実施した。
[実施例52]
B−IをB−VIIに替えた以外は、実施例46と同様に実施した。
[実施例53]
B−IをB−VIIIに替えた以外は、実施例46と同様に実施した。
[実施例54]
B−IをB−IXに替えた以外は、実施例46と同様に実施した。
B−IをB−Xに替えた以外、実施例1と同様に実施した。
[比較例2]
OXE−01を添加しない以外は、実施例3と同様に実施した。
[比較例3]
B−Iを添加しない以外は、実施例1と同様に実施した。
[比較例4]
B−IをB−Xに替えた以外は、実施例23と同様に実施した。
[比較例5]
TP5−280Mを添加しない以外は、実施例25と同様に実施した。
[比較例6]
B−Iを添加しない以外は、実施例23と同様に実施した。
[比較例7]
B−IIIを添加しない以外は、実施例22と同様に実施した。
[比較例8]
B−IをB−Xに替えた以外、実施例37と同様に実施した。
[比較例9]
IC−819、OXE−02を添加しない以外は、実施例39と同様に実施した。
[比較例10]
B−Iを添加しない以外は、実施例37と同様に実施した。
[比較例11]
B−IをB−Xに替えた以外は、実施例46と同様に実施した。
[比較例12]
TP5−280Mを添加しない以外は、実施例48と同様に実施した。
[比較例13]
B−Iを添加しない以外は、実施例46と同様に実施した。
実施例および比較例の結果を以下の表に示す。
2 Alパッド
3 パッシベーション膜
4 絶縁膜
5 金属(Cr、Ti等)膜
6 金属配線(Al、Cu等)
7 絶縁膜
8 バリアメタル
9 スクライブライン
10 ハンダバンプ
Claims (17)
- (A)エポキシ樹脂、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およびポリシロキサンからなる群から選ばれるいずれか1種類以上の樹脂、(B)熱塩基発生剤および(C)感光剤を含有する感光性樹脂組成物であって、該(B)熱塩基発生剤がグアニジン誘導体および/またはビグアニド誘導体を含有し、該(C)感光剤が(c−1)光酸発生剤および/または(c−2)光ラジカル重合開始剤を含有する感光性樹脂組成物。
- 前記(A)樹脂が、ポリイミド前駆体を含有する、請求項1記載の感光性樹脂組成物。
- 前記(A)樹脂が、ポリシロキサンを含有する、請求項1または2記載の感光性樹脂組成物。
- 前記(B)熱塩基発生剤が、4級ホウ素アニオンを有するグアニジン誘導体および/またはビグアニド誘導体を含有する、請求項1〜3のいずれかに記載の感光性樹脂組成物。
- 前記一般式(1)中のZ−が、一般式(2)〜(4)のいずれかの構造を含む請求項5に記載の感光性樹脂組成物。
- 前記(A)樹脂が、ビフェニル構造を有するポリイミド前駆体を含有する、請求項1〜7に記載の感光性樹脂組成物。
- 前記(A)樹脂が、3価以上のアミノ化合物の残基を有するポリイミド前駆体を含有する、請求項1〜8に記載の感光性樹脂組成物。
- 前記(C)感光剤が、(c−1)光酸発生剤を含有する、請求項1〜9のいずれかに記載の感光性樹脂組成物。
- 前記(C)感光剤が、(c−2)光ラジカル重合開始剤を含有し、該(c−2)光ラジカル重合開始剤がアルキルフェノン化合物、アミノベンゾフェノン化合物、ジケトン化合物、ケトエステル化合物、ホスフィンオキサイド化合物、オキシムエステル化合物および安息香酸エステル化合物からなる群から選ばれるいずれか一種類以上を含有する請求項1〜9のいずれかに記載の感光性樹脂組成物。
- 前記(A)樹脂100質量部に対し、前記(B)熱塩基発生剤の含有量が、0.1質量部以上10質量部以下である請求項1〜11のいずれかに記載の感光性樹脂組成物。
- 請求項1〜12のいずれかに記載の感光性樹脂組成物から形成された感光性シート。
- 請求項1〜12のいずれかに記載の感光性樹脂組成物、または請求項13記載の感光性シートを硬化した硬化膜。
- 請求項1〜12のいずれかに記載の感光性樹脂組成物を基板に塗布し、または請求項13に記載の感光性シートを基板上にラミネートし、乾燥して感光性樹脂膜を形成する工程と、該感光性樹脂膜を露光する工程と、露光後の感光性樹脂膜を現像する工程と、現像後の感光性樹脂膜を加熱処理する工程とを含む、硬化膜の製造方法。
- 前記現像後の感光性樹脂膜を加熱処理する工程が、170℃以上280℃以下で加熱処理する工程を含む、請求項15に記載の硬化膜の製造方法。
- 請求項14に記載の硬化膜のレリーフパターンを有する、電子部品。
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