JP5733618B2 - 塩基増殖剤及び当該塩基増殖剤を含有する塩基反応性樹脂組成物 - Google Patents
塩基増殖剤及び当該塩基増殖剤を含有する塩基反応性樹脂組成物 Download PDFInfo
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- JP5733618B2 JP5733618B2 JP2011104792A JP2011104792A JP5733618B2 JP 5733618 B2 JP5733618 B2 JP 5733618B2 JP 2011104792 A JP2011104792 A JP 2011104792A JP 2011104792 A JP2011104792 A JP 2011104792A JP 5733618 B2 JP5733618 B2 JP 5733618B2
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- 229920006130 high-performance polyamide Polymers 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003617 indole-3-acetic acid Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXLUTPDNMOEWGG-UHFFFAOYSA-N kryptand 222b Chemical compound C1COCCOCCN2CCOCCOCCN1CCOC1=CC=CC=C1OCC2 QXLUTPDNMOEWGG-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- JZBZLRKFJWQZHU-UHFFFAOYSA-N n,n,2,4,6-pentamethylaniline Chemical compound CN(C)C1=C(C)C=C(C)C=C1C JZBZLRKFJWQZHU-UHFFFAOYSA-N 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- DOWRVBBMIKAQLL-UHFFFAOYSA-N n,n,3,3,4,5,5-heptamethylpiperazin-1-amine Chemical compound CN(C)N1CC(C)(C)N(C)C(C)(C)C1 DOWRVBBMIKAQLL-UHFFFAOYSA-N 0.000 description 1
- NBFRQCOZERNGEX-UHFFFAOYSA-N n,n,3,5-tetramethylaniline Chemical compound CN(C)C1=CC(C)=CC(C)=C1 NBFRQCOZERNGEX-UHFFFAOYSA-N 0.000 description 1
- CWOMTHDOJCARBY-UHFFFAOYSA-N n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1 CWOMTHDOJCARBY-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 1
- WVFBFEWKWKPZOV-UHFFFAOYSA-N n,n,n',n'-tetrabenzylmethanediamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 WVFBFEWKWKPZOV-UHFFFAOYSA-N 0.000 description 1
- UPPIBFVZIFKMFO-UHFFFAOYSA-N n,n,n',n'-tetrabutylhexane-1,6-diamine Chemical compound CCCCN(CCCC)CCCCCCN(CCCC)CCCC UPPIBFVZIFKMFO-UHFFFAOYSA-N 0.000 description 1
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 1
- RCZLVPFECJNLMZ-UHFFFAOYSA-N n,n,n',n'-tetraethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN(CC)CC RCZLVPFECJNLMZ-UHFFFAOYSA-N 0.000 description 1
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- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- DNOJGXHXKATOKI-UHFFFAOYSA-N n,n,n',n'-tetramethylpentane-1,5-diamine Chemical compound CN(C)CCCCCN(C)C DNOJGXHXKATOKI-UHFFFAOYSA-N 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- GSLWSSUWNCJILM-UHFFFAOYSA-N n,n-dibenzyl-2-chloroethanamine Chemical compound C=1C=CC=CC=1CN(CCCl)CC1=CC=CC=C1 GSLWSSUWNCJILM-UHFFFAOYSA-N 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
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- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
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- PMHXGHYANBXRSZ-UHFFFAOYSA-N n,n-dimethyl-2-morpholin-4-ylethanamine Chemical compound CN(C)CCN1CCOCC1 PMHXGHYANBXRSZ-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 description 1
- MMWFTWUMBYZIRZ-UHFFFAOYSA-N n,n-dimethylundecan-1-amine Chemical compound CCCCCCCCCCCN(C)C MMWFTWUMBYZIRZ-UHFFFAOYSA-N 0.000 description 1
- 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
- SKACCCDFHQZGIA-UHFFFAOYSA-N n-(4-nitronaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=C([N+]([O-])=O)C2=C1 SKACCCDFHQZGIA-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- SNGBVBNOXIPZGP-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CC1=CC=C(Br)C=C1 SNGBVBNOXIPZGP-UHFFFAOYSA-N 0.000 description 1
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 1
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- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 239000003973 paint Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- 150000003003 phosphines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 238000012643 polycondensation polymerization Methods 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical class 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
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- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
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- SXPSZIHEWFTLEQ-UHFFFAOYSA-N tröger's base Chemical compound C12=CC=C(C)C=C2CN2C3=CC=C(C)C=C3CN1C2 SXPSZIHEWFTLEQ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Materials For Photolithography (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Epoxy Resins (AREA)
- Silicon Polymers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
橋反応に用いることができ、塩基の存在によって新たな塩基を発生可能であり、かつ塩基増殖反応が効率的に進行する塩基増殖剤及び当該塩基増殖剤を含有する塩基反応性樹脂組成物を提供することにある。
ヘテロ原子を含んでもよい。)、またはフェニル基、を示す。)
(アルキル基は環状構造でもよい。)を示す。)
ル(CH3CN溶媒中)は10(アミン)〜24(アミジン類)であり、この程度の塩基
性ではラクトン類や環状シロキサンのアニオン開環重合は起こりにくい一方、塩基増殖剤を構成する塩基類としてグアニジン類やホスファゼン誘導体を採用した場合には、pKaが26〜27程度(アセトニトリル(CH3CN)溶媒中)となりアニオン開環重合が起こるため、これを用いるとモノマーが連鎖反応でポリマーに変化する。塩基類としてグアニジン類やホスファゼン誘導体を採用した場合の塩基増殖剤は、ラクトン類等に最適な塩基増殖剤となり、光塩基発生剤と併用してラクトン類等に適用して塩基反応性樹脂組成物(感光性樹脂組成物)とした場合には、光硬化材料(UV接着、UVインク、UV粘着、UVコーティングなど)に適用することができる。
(アルキル基は環状構造でもよい。)を示す。)
(アルキル基は環状構造でもよい。)を示す。)
前記した塩基増殖剤、あるいは塩基増殖剤及び塩基発生剤(塩基増殖剤組成物)と、塩基の存在によって硬化反応をする塩基反応性化合物を必須成分として含有する。
スキーム4のように、生成したOH−から6が生成するが、この場合も、酸素原子上の電
荷は消失せず、次のエポキシ系化合物と反応し7を生成することになる。従って、前記し
たスキームと同様にエポキシ系化合物との反応は連鎖的に進行し、エポキシ系化合物との
反応効率が格段に高くなる。
その他、本発明の実施の際の具体的な構造及び形状等は、本発明の目的を達成できる範囲で他の構造等としてもよい。
カルボン酸の製造(1):
下記(1)(2)の操作を用いて、式(III−a)に示すカルボン酸を製造した。
二口フラスコにアセト酢酸tert−ブチル(tBAA)0.30g(1.9×10−3mol)、トリエチルアミン0.20g(1.9×10−3mol)を入れ、テトラヒドロフラン(THF)20mlに溶解させ、0℃で10分攪拌した。また、バイアルに下記式(III−a1)に示したクロロぎ酸9−フルオレニルメチル0.50g(1.9×10−3mol)を入れ、テトラヒドロフラン(THF)20mlに溶解させた後、二口フラスコに入れた。二口フラスコの混合物を室温で2時間以上攪拌した後、クロロホルム(CHCl3)を50ml入れ、塩酸水溶液、炭酸水素ナトリウム水溶液、塩化ナトリウム水溶液の順で抽出し、硫酸マグネシウム適量を加えた後、酢酸エチルとヘキサンを酢酸エチル/ヘキサン=1/20の展開溶媒を用いてカラムクロマトグラフィーにより分離し、下記式(III−a2)に示した中間体の黄色粘性液体を収量0.26g(0.68×10−3mol)、収率36%で得た。
二口フラスコに(1)で得られた中間体を0.85g(2.2×10−3mol)、p−トルエンスルホン酸0.08g(0.49×10−3mol)、ベンゼン20mlを入れ、80℃で3時間以上還流した。還流後、酢酸エチルとヘキサンを酢酸エチル/ヘキサン=1/5の展開溶媒を用いてカラムクロマトグラフィーにより分離し、式(III−a)に示したカルボン酸の白色固体を収量0.44g(1.4×10−3mol)、収率64%で得た。
カルボン酸の製造(2):
下記(1)(2)の操作を用いて、式(III−b)に示すカルボン酸を製造した。
二口フラスコにアセト酢酸tert−ブチル0.34g(2.2×10−3mol)、トリエチルアミン0.23g(2.3×10−3mol)を入れ、テトラヒドロフラン(THF)20mlに溶解させ、0℃で10分攪拌した。また、バイアルに下記式(III−b1)に示した2,7−ジ−tert−ブチル−9−フルオレニルメチルクロロホーメート0.80g(2.2×10−3mol)を入れ、テトラヒドロフラン(THF)20mlに溶解させた後、二口フラスコに入れた。二口フラスコの混合物を室温で2時間以上攪拌した後、クロロホルム(CHCl3)を50ml入れ、塩酸水溶液、炭酸水素ナトリウム水溶液、塩化ナトリウム水溶液の順で抽出し、硫酸マグネシウムを適量加えた後、酢酸エチルとヘキサンを酢酸エチル/ヘキサン=1/20の展開溶媒を用いてカラムクロマトグラフィーにより分離し、下記式(III−b2)に示した中間体の白色固体を収量0.31g(0.63×10−3mol)、収率29%で得た。
二口フラスコに(1)で得られた中間体を1.43g(2.9×10−3mol)、p−トルエンスルホン酸0.10g(0.58×10−3mol)、ベンゼン60mlを入れ、80℃で3時間以上還流した。還流後、酢酸エチルとヘキサンを酢酸エチル/ヘキサン=1/5の展開溶媒を用いてカラムクロマトグラフィーにより分離し、式(III−b)に示したカルボン酸の白色固体を収量0.70g(1.6×10−3mol)、収率55%で得た。
塩基増殖剤の製造(1):
二口フラスコに前記の方法で得られた式(III−a)に示したカルボン酸0.20g(0.62×10−3mol)をジメチルエーテル100mlに入れて0℃で攪拌混合した。また、バイアルに塩基であり式(IV−c)で示した1,5,7−トリアザ−ビシクロ[4.4.0]デシ−5−エン(TBD)0.08g(0.58×10−3mol)をジメチルエーテル100mlに入れて超音波混合した後、二口フラスコに入れた。二口フラスコ中の混合物を0℃で1時間攪拌して反応させた。反応終了後、吸引ろ過して溶媒を除去し、下記式(X−a)で表される本発明の塩基増殖剤の白色固体を収量0.12g(0.26×10−3mol)、収率47%で得た(酸/塩基=1/1)。
塩基増殖剤の製造(2):
二口フラスコに前記の方法で得られた式(III−b)に示したカルボン酸0.136g(0.31×10−3mol)をジメチルエーテル200mlに入れて0℃で攪拌混合した。また、バイアルに塩基であり式(IV−c)で示した1,5,7−トリアザ−ビシクロ[4.4.0]デシ−5−エン(TBD)0.042g(0.30×10−3mol)をジクロロメタン200mlに入れて超音波混合した後、二口フラスコに入れた。二口フラスコ中の混合物を0℃で1時間攪拌して反応させた。反応終了後、濃縮して溶媒を除去し、下記式(X−b)で表される本発明の塩基増殖剤の白色固体を粗収量0.179g(0.31×10−3mol)、粗収率100%で得た(酸/塩基=1/0.95)。
塩基増殖剤の製造(3):
二口フラスコに前記の方法で得られた式(III−b)に示したカルボン酸0.30g(0.69×10−3mol)をジメチルエーテル60mlに入れて0℃で攪拌混合した。また、バイアルに塩基であり式(V−e)で示したホスファゼン誘導体であるイミノ−トリス(ジメチルアミノ)ホスホラン0.11g(0.62×10−3mol)をジメチルエーテル60mlに入れて超音波混合した後、二口フラスコに入れた。二口フラスコ中の混合物を0℃で1時間攪拌して反応させた。反応終了後、濃縮して溶媒を除去し、下記式(X−b2)で表される本発明の塩基増殖剤の白色固体を粗収量0.41g(0.67×10−3mol)、粗収率108%で得た(酸/塩基=1/0.98)。
カルボン酸の製造(3)
二口フラスコにインドール−3−酢酸(IBA)酸5.6g(23×10−3mol)、3−(4−ヒドロ−キシフェニル)プロピオン酸(HPPA)5.2g(31×10−3mol)、炭酸セシウム(Cs2CO3)28g(86×10−3mol)、1,4−ジオキサン100mlを入れて混合した後、20分間窒素置換した。窒素置換後、トリス(2− (2−メトキシエトキシ)エチル)アミン(TDA−1)0.9g(2.8×10−3mol)、塩化銅(I)(CuCl)0.27g(2.7×10−3mol)を入れ、110℃で20時間還流した。還流後、濃縮し、得られた生成物に0.1Mの水酸化ナトリウム水溶液を加えた後ろ過した。ろ過後、1Mの塩酸水溶液と酢酸エチルで3回抽出し、硫酸マグネシウムを適量加えた後、濃縮、減圧乾燥し、硫酸12mlを加え、85℃で1時間加熱攪拌した。加熱攪拌後、放冷し、氷を投入した。酢酸エチルで3回抽出した。硫酸マグネシウムを加え、濃縮し、トルエンで3回再結晶することにより、式(VII−a)で表されるメチルキサントン酢酸の白色固体を収量1.59g(5.9×10−3mol)、収率26%で得た。
式(VII−a)に示したメチルキサントン酢酸0.30g(1.1×10−3mol)のテトラヒドロフラン(THF)溶液に、式(IV−c)に示したTBD0.16g(1.1×10−3mol)を滴下後、室温で1時間混合した後、溶媒を減圧留去した。得られた固体をテトラヒドロフラン(THF)で洗浄、減圧乾燥することで、下記(H−a)で表される塩基発生剤の白色固体を0.26g(収率58%)得た。
前記した式(VII−a)に示したメチルキサントン酢酸0.10g(0.37×10−3mol)のエタノール溶液に、式(V−e)に示したイミノ−トリス(ジメチルアミノ)ホスホラン0.16g(0.37×10−3mol)を滴下後、室温で1時間混合することで得られた黄色粘性液体をエーテルで洗浄することで、下記式(H−b)で表される塩基発生剤の黄色粘性液体を0.10g(収率60%)得た。
溶液中での塩基増殖剤の分解挙動の確認(1):
塩基増殖剤は、スキーム1に示すように、塩基の添加により分解反応が起こり、塩基及びケトン(本実施例ではアセトン)とともに、実施例1の塩基増殖剤ではDBF(ジベンゾフルベン)、実施例2及び実施例3の塩基増殖剤ではtBDBF(ジ−tert−ブチルジベンゾフルベン)が発生する。下記の方法を用いて、塩基増殖剤の分解挙動を確認した。
溶液中での塩基増殖剤の分解挙動の確認(2)
NMR試料管に、実施例3で得られた塩基増殖剤0.030g(69×10−3mol/L)、塩基であり式(V−e)で示したホスファゼン誘導体1.7μl(13×10−3mol/L)、重ベンゼン0.75ml、メシチレン1.3μl(13×10−3mol/L)を入れ、封管した後50℃で所定の時間加熱した。そして、1H−NMRにより、発生するtBDBF中のオレフィンピークを追跡することにより、塩基増殖剤の分解挙動(オレフィンの生成)を確認し、塩基を添加しない場合と比較した。加熱時間と生成率との関係を図3(溶媒 重ベンゼン)に示す。なお、オレフィンの生成率は、試験例1と同様にして算出した。
高分子固体(ポリスチレン)中での塩基増殖剤の分解挙動の確認(1):
ポリスチレン(Aldroch社製、Mw=250000)0.12gに対して、実施例2で得られた塩基増殖剤0.20g(30mol%)(ポリスチレン100質量部に対して167質量部)、塩基であり式(IV−c)で示した1,5,7−トリアザ−ビシクロ[4.4.0]デシ−5−エン(TBD)0.006g(4mol%)、(ポリスチレン100質量部に対して約5質量部)を含有させることにより樹脂組成物とした。かかる樹脂組成物を、キャスト溶媒としてジクロロエタン(CH2Cl2)3mlに溶解させて試料溶液とし、この試料溶液を3000rpmで30秒間シリコンウェハ上にスピンコートし、ホットプレート上にて60℃で1分間プリベイクすることにより製膜した。この膜を50℃で所定の時間加熱して、IRスペクトルにより、転化するカルボニル基(C=O)のピーク(1757cm−1)を追跡することにより、塩基増殖剤の分解挙動を確認し、塩基を添加しない場合と比較した。加熱時間と添加率との関係を図4に示す。なお、カルボニル基の転化率は、加熱開始前のピーク強度を基準として算出した。
塩基反応性樹脂組成物の製造(1):
式(No.4−12)に表されるエポキシ系化合物であるポリグリシジルメタクリレート(PGMA,MW=10000)0.1gに対して、式(H−a)で表される塩基発生剤を0.004g(PGMAのモノマーユニットに対して1.5mol%)(PGMA100質量部に対して4.0質量部)、実施例2で得られた塩基増殖剤を0.002g(PGMAのモノマーユニットに対して0.5mol%)(PGMA100質量部に対して2.0質量部)含有させることにより本発明の塩基反応性樹脂組成物を得た。
塩基反応性樹脂組成物の製造(2):
実施例4において、塩基増殖剤の含有量を0.004g(PGMAのモノマーユニットに対して1.0mol%)(PGMA100質量部に対して4.0質量部)とした以外は実施例4と同様な方法を用いて、本発明の塩基反応性樹脂組成物を得た。
塩基反応性樹脂組成物の製造(3):
実施例4において、塩基増殖剤の含有量を0.008g(PGMAのモノマーユニットに対して2.0mol%)(PGMA100質量部に対して8.0質量部)とした以外は実施例4と同様な方法を用いて、本発明の塩基反応性樹脂組成物を得た。
樹脂組成物の製造(1)
実施例4において、塩基増殖剤を含有させなかった以外は実施例4と同様な方法を用いて、樹脂組成物を得た。
光不溶化挙動の確認(1):
実施例4で得られた塩基反応性樹脂組成物を1.5gのクロロホルムに溶解させた。この試料溶液を3000rpmで30秒間シリコンウェハ上にスピンコートし、ホットプレート上にて80℃で15秒間プリベイクすることにより、厚さ0.6μmの膜を作製した。この膜に365nmの単色光を照射し、ポストベイクの温度を80℃として30分間実施し、クロロホルムで30秒間現像し、残っている膜の厚さを測定した。そして、同様な操作を、実施例5で得られた塩基反応性樹脂組成物、並びに参考例1で得られた樹脂組成物に対して実施し、それぞれについて露光量と残膜率との関係(感度曲線)を作成した。得られた感度曲線を図5に示す。
塩基反応性樹脂組成物の製造(4):
エポキシ系化合物であるソルビトールポリグリシジルエーテル(EX−614B/ナガセケムテックス(株)製)(MW=406)0.25g(0.62×10−3mol)、チオール化合物であるペンタエリスリトールテトラキス(3−メルカプトブチレート)(カレンズMT(登録商標)PE−1/昭和電工(株)製)0.042g(エポキシ系化合物に対して1/8倍mol)(0.077×10−3mol)、式(H−a)で表される塩基発生剤をエポキシ系化合物に対して3.0mol%(エポキシ系化合物100質量部に対して3.0質量部)に、実施例2で得られた塩基増殖剤を下記のように含有させることにより本発明の塩基反応性樹脂組成物を得た。
含有量(g) mmol エポキシ系化合物に対して
実施例7 0.005 0.0087 1.5mol%
実施例8 0.010 0.017 3.0mol%
実施例9 0.020 0.035 6.0mol%
樹脂組成物の製造(2):
実施例7において、塩基増殖剤を含有させなかった以外は実施例7と同様な方法を用いて、樹脂組成物を得た。
硬化確認(1):
実施例7、実施例8及び実施例9及び参考例2で得られた塩基反応性樹脂組成物(感光性樹脂組成物)等をジクロロエタン(CH2Cl2)に溶解させて試料溶液とした。この試料溶液をガラス基板上にバーコートして製膜し、50℃で30秒間加熱してプリベイクし、厚さ1.7μmの塗膜を調製した。この塗膜に365nmの単色光を、露光量を0(ブランク)、1000及び10000mJ/cm2として、50℃で5分間加熱後の塗膜の硬度をJIS K5600−5−4に準拠して鉛筆硬度測定を行い、比較・評価した。結果を図6に示す。
塩基反応性樹脂組成物の製造(5):
エポキシ系化合物であるソルビトールポリグリシジルエーテル(EX−614B/ナガセケムテックス(株)製)(MW=406)0.25g(0.62×10−3mol)、チオール化合物であるペンタエリスリトールテトラキス(3−メルカプトブチレート)(カレンズMT(登録商標)PE−1/昭和電工(株)製)0.042g(エポキシ系化合物に対して1/8倍mol)(0.077×10−3mol)、式(H−b)で表される塩基発生剤をエポキシ系化合物に対して3.0mol%(エポキシ系化合物100質量部に対して3.0質量部)に、実施例3で得られた塩基増殖剤を下記のように含有させることにより本発明の塩基反応性樹脂組成物を得た。
含有量(g) mmol エポキシ系化合物に対して
実施例10 0.006 0.0098 1.5mol%
実施例11 0.011 0.018 3.0mol%
実施例12 0.023 0.037 6.0mol%
樹脂組成物の製造(3):
実施例10において、塩基増殖剤を含有させなかった以外は実施例10と同様な方法を用いて、樹脂組成物を得た。
硬化確認(2):
実施例10、実施例11及び実施例12及び参考例3で得られた塩基反応性樹脂組成物(感光性樹脂組成物)等を試験例5と同様な方法を用いてJIS K5600−5−4に準拠して鉛筆硬度測定を行い、比較・評価した。結果を図7に示す。
塩基増殖剤の製造(4)
チオフェノール2.0g(18mmol)とブロモエタンジオール2.8g(18mmol)を200ml四つ口フラスコに入れ、KOHを溶かした水を溶媒として室温で3時間攪拌した。反応後クロロホルムで抽出を行いヘキサン:酢酸エチル=2:1の混合溶媒を展開溶媒としてカラムクロマトグラフィーにより分離精製することにより白色固体の3−(フェニルチオ)プロパン−1,2−ジオールを収量2.0g(収率55%)で得た。
溶液中での塩基増殖剤の分解挙動の確認(3)
NMR試料管に、実施例13で得られた塩基増殖剤0.020g、塩基であり式(IV−c)で示した1,5,7−トリアザ−ビシクロ[4.4.0]デシ−5−エン(TBD)0.002g、重テトラヒドロフラン(THF)0.75ml、メシチレン1.3μl(13×10−3mol/L)を入れ、封管した後70℃で所定の時間加熱した。そして、1H−NMRにより、発生するアセトンのピーク及び転化するメチル基のピークを追跡することにより、塩基増殖剤の分解挙動(アセトンの生成及びメチル基の転化)を確認し、塩基を添加しない場合と比較した。加熱時間と生成率との関係を図8、加熱時間と転化率との関係を図9に示す。なお、アセトンの生成率は、1H−NMRスペクトルから算出した。
Claims (7)
- 下記式(X)、下記式(X’)または下記式(X−1)で表されることを特徴とする塩基増殖剤。
- 請求項1に記載の塩基増殖剤及び塩基反応性化合物を含有することを特徴とする塩基反応性樹脂組成物。
- 請求項1に記載の塩基増殖剤と、塩基発生剤及び塩基反応性化合物を含有することを特徴とする塩基反応性樹脂組成物。
- 前記塩基発生剤が光塩基発生剤であることを特徴とする請求項3に記載の塩基反応性樹脂化合物。
- 前記塩基増殖剤を構成する塩基と前記塩基発生剤を構成する塩基が共通することを特徴とする請求項3または請求項4に記載の塩基反応性樹脂組成物。
- 前記塩基反応性化合物がエポキシ系化合物、ケイ素系化合物及びオキセタン系化合物からなる群より選ばれる少なくとも1種であることを特徴とする請求項2ないし請求項5のいずれかに記載の塩基反応性樹脂組成物。
- さらに、チオール化合物を含むことを特徴とする請求項2ないしは請求項6のいずれかに記載の塩基反応性樹脂組成物。
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JP6786811B2 (ja) * | 2016-02-10 | 2020-11-18 | 東ソー株式会社 | 有機塩基化合物、ルイス酸及び活性水素含有化合物を含む組成物 |
JP7287628B2 (ja) | 2017-12-12 | 2023-06-06 | 学校法人東京理科大学 | 活性エネルギー線硬化型組成物 |
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US11905361B2 (en) | 2018-02-26 | 2024-02-20 | Nippon Kayaku Kabushiki Kaisha | Base proliferating agent, and base-reactive resin composition containing said base proliferating agent |
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