JPWO2014017236A1 - ラジカル硬化性化合物、ラジカル硬化性化合物の製造方法、ラジカル硬化性組成物、その硬化物、及びレジスト材料用組成物 - Google Patents
ラジカル硬化性化合物、ラジカル硬化性化合物の製造方法、ラジカル硬化性組成物、その硬化物、及びレジスト材料用組成物 Download PDFInfo
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- JPWO2014017236A1 JPWO2014017236A1 JP2013544937A JP2013544937A JPWO2014017236A1 JP WO2014017236 A1 JPWO2014017236 A1 JP WO2014017236A1 JP 2013544937 A JP2013544937 A JP 2013544937A JP 2013544937 A JP2013544937 A JP 2013544937A JP WO2014017236 A1 JPWO2014017236 A1 JP WO2014017236A1
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- Prior art keywords
- radical curable
- curable compound
- meth
- group
- acrylate
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- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- SFHGONLFTNHXDX-UHFFFAOYSA-N [4-[4-(hydroxymethyl)phenyl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=C(CO)C=C1 SFHGONLFTNHXDX-UHFFFAOYSA-N 0.000 description 1
- SSFGHKDDKYEERH-UHFFFAOYSA-N [6-(hydroxymethyl)naphthalen-2-yl]methanol Chemical compound C1=C(CO)C=CC2=CC(CO)=CC=C21 SSFGHKDDKYEERH-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-WSORPINJSA-N acetylbenzoylaconine Chemical compound O([C@H]1[C@]2(O)C[C@H]3C45[C@@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)C4[C@]([C@@H](C[C@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-WSORPINJSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- RYXHOMYVWAEKHL-UHFFFAOYSA-N astatine atom Chemical compound [At] RYXHOMYVWAEKHL-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- QDVNNDYBCWZVTI-UHFFFAOYSA-N bis[4-(ethylamino)phenyl]methanone Chemical compound C1=CC(NCC)=CC=C1C(=O)C1=CC=C(NCC)C=C1 QDVNNDYBCWZVTI-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical class C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CYTJMBLSQUBVMS-UHFFFAOYSA-N n-[[2-cyanopropan-2-yl(formyl)amino]hydrazinylidene]formamide Chemical compound N#CC(C)(C)N(C=O)NN=NC=O CYTJMBLSQUBVMS-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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Abstract
Description
で表されることを特徴とするラジカル硬化性化合物を提供するものである。
で表される重縮合物(A)を得た後、該重縮合物に(メタ)アクリル酸ハライド(B)とを反応させることを特徴とするラジカル硬化性化合物の製造方法を提供するものである。
で表される分子構造を有する。
で表されるラジカル硬化性化合物となる。
で表される重縮合物(A)を得た後、該重縮合物に(メタ)アクリル酸ハライド(B)とを反応させる方法により容易に製造することができる。なお、本発明において、「(メタ)アクリル酸」とは、「アクリル酸」と「メタクリル酸」の一方又は両方をいう。
アルキル置換フェノール(a1)とベンゼン環上に水酸基を有する芳香族アルデヒド(a2)とを酸触媒存在下で重縮合することにより、反応溶液中に上記一般式(5)または一般式(6)で表される重縮合物(A)を含む粗生成物を得る。
工程1で得られた重縮合物(A)を反応溶液中から回収する。
工程2で単離した重縮合物(A)と(メタ)アクリル酸ハライド(B)とを塩基存在下で反応させる。
測定装置:東ソー株式会社製「HLC−8220 GPC」
カラム:昭和電工株式会社製「Shodex KF802」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF802」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF803」(8.0mmФ×300mm)
+昭和電工株式会社製「Shodex KF804」(8.0mmФ×300mm)
カラム温度:40℃
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.30」
展開溶媒:テトラヒドロフラン
流速:1.0ml/分
試料:樹脂固形分換算で0.5質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの
注入量:0.1ml
標準試料:下記単分散ポリスチレン
東ソー株式会社製「A−500」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
日本電子株式会社製「JNM−GSX500(500MHz,DMSO−d6,TMS)」を用いて構造解析を行った。
冷却管を設置した100ml2口フラスコに2,5−キシレノール7.32g(60mmol)、4−ヒドロキシベンズアルデヒド2.44g(20mmol)を仕込み、2−エトキシエタノール20mlに溶解させた。氷浴中で冷却しながら硫酸2mlを添加した後、100℃のオイルバス中で2時間加熱、攪拌し反応させた。反応後、得られた溶液を水で再沈殿操作を行い粗生成物を得た。粗生成物をアセトンに再溶解し、さらに水で再沈殿操作を行った後、得られた生成物を濾別、真空乾燥を行い下記式(5−1)で表される分子構造を有する重縮合物(A−1)5.93gを得た。ここで、粗生成物における重縮合物(A−1)の純度はGPCの面積比で87質量%であり、最終的に得られた重縮合物(A−1)の純度は99質量%であった。
冷却管を設置した100ml2口フラスコに重縮合物(A−1)1.74g(5mmol)、炭酸カリウム4.10g(30mmol)、テトラヒドロフラン10mlを仕込み撹拌を開始した。氷浴中で冷却しながらアクリル酸クロライド3.60g(20mmol)を30分で滴下しながら添加した後、70℃のオイルバス中で12時間加熱、攪拌し反応させた。反応後、得られた溶液から固形分を濾別し、濾液をクロロホルム30mlと混合し、水50mlで3回洗浄を行った。下層である有機層を分取後、硫酸ナトリウムで乾燥した後、溶剤を減圧留去し白色針状結晶のラジカル硬化性化合物(1)1.79gを得た。1H-NMRの各ピークにより同定し、下記構造式(3−1)で表される化合物が100%の純度で得られたことを確認した。1H−NMRスペクトルのチャート図を図1に示す。
[1H−NMRスペクトル]
(ppm、500MHz、溶媒:DMSO−d6、基準:TMS)
1.9−2.2(12H;Ar−CH 3 ),5.6−5.8(1H;Ar−CH),6.1−6.3(3H;C−CH 2 ),6.4−6.5(3H;CO−CH−C),6.5−6.6(2H;Ar),6.6−6.7(3H;C−CH 2 ),6.9−7.3(6H;Ar)
ビスフェノールA(BPA)型液状エポキシ樹脂(DIC株式会社製「EPICLON850」;エポキシ当量188g/eq.)188質量部とアクリル酸72質量%(エポキシ基の数:総カルボキシル基の数=1:1となる比率)とを95℃で反応させて、透明粘調液体のBPA型エポキシアクリレート253質量部を得た。
テトラメチルビフェニル型液状エポキシ樹脂(三菱化学株式会社製「JER YX−4000H」;エポキシ当量195g/eq.)195質量部とアクリル酸72質量部(エポキシ基の数:総カルボキシル基の数=1:1となる比率)とを95℃で反応させて、透明粘調液体のテトラメチルビフェニル型エポキシアクリレート264質量部を得た。
o−クレゾールノボラック型エポキシ樹脂(DIC株式会社製「EPICLON N−695」;エポキシ当量214g/eq.)214質量部とアクリル酸72質量部(エポキシ基の数:総カルボキシル基の数=1:1となる比率)を100℃で反応させて、黄色固形のクレゾールノボラック型エポキシアクリレート273質量部を得た。
上記の実施例1及び比較合成例1〜3で得られたアクリレートを用いて、試験例1、2及び比較試験例1〜6に示すように硬化物を調製した。下記方法に従って、硬化物のガラス転移点温度の測定を行うと共に、硬化物の耐熱性の評価を行い、その結果を第1表に示す。
実施例1で得られたラジカル硬化性化合物(1)0.50gと、イルガキュア184〔チバ・スペシャリティ(株)製〕0.05gとテトラヒドロフラン0.5gをシュレンク管に入れ、窒素雰囲気下で凍結乾燥を行った。この反応器を密閉し、340nmのバンドパスフィルターを装着した高圧水銀灯で3時間光を照射した。得られた内容物をメタノールで再沈殿操作を行い、得られた沈殿物を濾過、真空乾燥を行い重合体(a)0.35gを得た。得られた重合体(a)のDSC測定を行い、耐熱性(Tg)を評価した。
実施例1で得られたラジカル硬化性化合物(1)0.50gと、アゾビスイソブチロニトリル〔AIBN;和光純薬(株)試薬〕0.05gとジクロロエタン0.5gをシュレンク管に入れ、窒素雰囲気下で凍結乾燥を行った。この反応器を密閉し、70℃で12時間反応を行った。得られた内容物をメタノールで再沈殿操作を行い、得られた沈殿物を濾過、真空乾燥を行い重合体(b)0.21gを得た。得られた重合体(b)のDSC測定を行い、耐熱性(Tg)を評価した。
実施例2で用いたラジカル硬化性化合物(1)に代えて、比較合成例1で得られたBPA型エポキシアクリレートを用いた以外は実施例2と同様の操作を行い、BPA型エポキシアクリレートの硬化物0.23gを得た。試験例1と同様にして耐熱性(Tg)を評価した。
実施例3で用いたラジカル硬化性化合物(1)に代えて、比較合成例1で得られたBPA型エポキシアクリレートを用いた以外は実施例3と同様の操作を行い、BPA型エポキシアクリレートの硬化物0.13gを得た。試験例1と同様にして耐熱性(Tg)を評価した。
実施例2で用いたラジカル硬化性化合物(1)に代えて、比較合成例2で得られたテトラメチルビフェニル型エポキシアクリレートを用いた以外は実施例2と同様の操作を行い、テトラメチルビフェニル型エポキシアクリレートの硬化物0.35gを得た。試験例1と同様にして耐熱性(Tg)を評価した。
実施例3で用いたラジカル硬化性化合物(1)に代えて、比較合成例2で得られたテトラメチルビフェニル型エポキシアクリレートを用いた以外は実施例3と同様の操作を行い、テトラメチルビフェニル型エポキシアクリレートの硬化物0.33gを得た。試験例1と同様にして耐熱性(Tg)を評価した。
実施例2で用いたラジカル硬化性化合物(1)に代えて、比較合成例3で得られたクレゾールノボラック型エポキシアクリレートを用いた以外は実施例2と同様の操作を行い、クレゾールノボラック型エポキシアクリレートの硬化物0.37gを得た。試験例1と同様にして耐熱性(Tg)を評価した。
実施例3で用いたラジカル硬化性化合物(1)に代えて、比較合成例3で得られたクレゾールノボラック型エポキシアクリレートを用いた以外は実施例3と同様の操作を行い、クレゾールノボラック型エポキシアクリレートの硬化物0.42gを得た。試験例1と同様にして耐熱性(Tg)を評価した。
示差熱走査熱量計(株式会社ティー・エイ・インスツルメント製「示差熱走査熱量計(DSC)Q100」)を用いて、窒素雰囲気下、温度範囲25〜450℃、昇温速度10℃/分の条件で、ガラス転移温度(以下、「Tg」と略記する。)を測定した。
上記の測定で得られたTgの温度から、下記の基準にしたがって耐熱性を評価した。
◎:Tgが300℃以上である。
○:Tgが250℃以上300℃未満である。
△:Tgが200℃以上250℃未満である。
×:Tgが200℃未満である。
Claims (12)
- 前記R1、R2およびR3が何れもメチル基である請求項1記載のラジカル硬化性化合物。
- 前記m、n及びpがそれぞれ独立して1〜3の整数である請求項1記載のラジカル硬化性化合物。
- 前記アルキル置換フェノール(a1)が、2,5−キシレノールまたは2,6−キシレノールである請求項5記載のラジカル硬化性化合物の製造方法。
- 前記ベンゼン環上に水酸基を有する芳香族アルデヒド(a2)が4−ヒドロキシベンズアルデヒドである請求項5記載のラジカル硬化性化合物の製造方法。
- アルキル置換フェノール(a1)とベンゼン環上に水酸基を有する芳香族アルデヒド(a2)とを酸触媒存在下で重縮合することにより、反応溶液中に重縮合物(A)を含む粗生成物を得る工程1と、工程1で得られた重縮合物(A)を反応溶液中から回収する工程2と、工程2で単離した重縮合物(A)と(メタ)アクリル酸ハライド(B)とを塩基存在下で反応させる工程3を含む請求項5記載のラジカル硬化性化合物の製造方法。
- 請求項5〜8の何れか一つに記載の製造方法により得られるラジカル硬化性化合物。
- 請求項1〜4、又は請求項9の何れか一つに記載のラジカル硬化性化合物を含有するラジカル硬化性組成物。
- 請求項10記載のラジカル硬化性組成物を活性エネルギー線または熱により硬化させて得られる硬化物。
- 請求項10記載のラジカル硬化性組成物からなるレジスト材料用組成物。
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