JP2020164720A - 重合性不飽和基含有アルカリ可溶性樹脂の製造方法、重合性不飽和基含有アルカリ可溶性樹脂、それを含む感光性樹脂組成物、それを硬化してなる硬化物、その硬化物を構成成分として含むタッチパネルおよびカラーフィルター - Google Patents
重合性不飽和基含有アルカリ可溶性樹脂の製造方法、重合性不飽和基含有アルカリ可溶性樹脂、それを含む感光性樹脂組成物、それを硬化してなる硬化物、その硬化物を構成成分として含むタッチパネルおよびカラーフィルター Download PDFInfo
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
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- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
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- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
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- 150000001934 cyclohexanes Chemical class 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JNWGOCSTXJQFEP-UHFFFAOYSA-N hexane-1,1,1,2-tetracarboxylic acid Chemical compound CCCCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O JNWGOCSTXJQFEP-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
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- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- MIVZUXGHPJSKRI-UHFFFAOYSA-N pentane-1,1,1,2-tetracarboxylic acid Chemical compound CCCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O MIVZUXGHPJSKRI-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 238000001179 sorption measurement Methods 0.000 description 1
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- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
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- 229920001187 thermosetting polymer Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
Abstract
Description
ピグメント・レッド2、3、4、5、9、12、14、22、23、31、38、112、122、144、146、147、149、166、168、170、175、176、177、178、179、184、185、187、188、202、207、208、209、210、213、214、220、221、242、247、253、254、255、256、257、262、264、266、272、279等
ピグメント・オレンジ5、13、16、34、36、38、43、61、62、64、67、68、71、72、73、74、81等
ピグメント・イエロー1、3、12、13、14、16、17、55、73、74、81、83、93、95、97、109、110、111、117、120、126、127、128、129、130、136、138、139、150、151、153、154、155、173、174、175、176、180、181、183、185、191、194、199、213、214等
ピグメント・グリーン7、36、58等
ピグメント・ブルー15、15:1、15:2、15:3、15:4、15:6、16、60、80等ピグメント・バイオレット19、23、37等
合成例および比較合成例中で得られた樹脂溶液、感光性樹脂組成物等の1gをガラスフィルター〔質量:W0(g)〕に含浸させて秤量し〔W1(g)〕、160℃にて2時間加熱した後の質量〔W2(g)〕から下記式(1)より求めた。
固形分濃度(質量%)=100×(W2−W0)/(W1−W0)
樹脂溶液をテトラヒドロフランに溶解させ、電位差滴定装置「COM−1600」(平沼産業株式会社製)を用いて1/10N−KOH水溶液で滴定して、固形分1gあたりに必要となったKOHの量を酸価とした。
ゲルパーミュエーションクロマトグラフィー(GPC)「HLC−8220GPC」(東ソー株式会社製、溶媒:テトラヒドロフラン、カラム:TSKgelSuperH−2000(2本)+TSKgelSuperH−3000(1本)+TSKgelSuperH−4000(1本)+TSKgelSuper−H5000(1本)(東ソー株式会社製)、温度:40℃、速度:0.6ml/min)にて測定し、標準ポリスチレン(東ソー株式会社製、PS−オリゴマーキット)換算値として重量平均分子量(Mw)を求めた。
HBPA−EA1:水添BisAエポキシ(エポキシ当量201g/eq)(式(1)
の骨格を有する)とアクリル酸との反応物(エポキシ基とカルボ
キシ基の等当量反応物)
HBPA−EA2:水添BisAエポキシ(エポキシ当量265g/eq)(式(1)
の骨格を有する)とアクリル酸との反応物(エポキシ基とカルボ
キシ基の等当量反応物)
BPA−EA :BisAエポキシ(エポキシ当量189g/eq)(式(22)
の骨格を有する)とアクリル酸との反応物(エポキシ基とカル
ボキシ基の等当量反応物)
BPF−EA :Bisフェノールフルオレン型エポキシ(エポキシ当量250
g/eq)(式(22)の骨格を有する)とアクリル酸との反応
物(エポキシ基とカルボキシル基の等当量反応物)
BPDA :3,3’,4,4’−ビフェニルテトラカルボン酸二無水物
HPMDA :1,2,4,5−シクロヘキサンテトラカルボン酸二無水物
THPA :1,2,3,6−テトラヒドロフタル酸無水物
TEAB :臭化テトラエチルアンモニウム
PGMEA :プロピレングリコールモノメチルエーテルアセテート
還留冷却器付き1000ml四つ口フラスコ中に、HBPA−EA1の50%PGMEA溶液(329.1g)と、BPDA(44.1g)と、THPA(22.8g)と、TEAB(0.43g)と、PGMEA(8.5g)と、を仕込み、120〜125℃で6時間撹拌し、アルカリ可溶性樹脂(i)−1を得た。得られた樹脂の固形分濃度は61.2質量%、酸価(固形分換算)は123.1mgKOH/g、および分子量(Mw)は3210であった。
還留冷却器付き1000ml四つ口フラスコ中に、HBPA−EA1の50%PGMEA溶液(340.0g)と、HPMDA(34.7g)と、THPA(23.6g)と、TEAB(0.43g)と、PGMEA(8.5g)と、を仕込み、120〜125℃で6時間撹拌し、アルカリ可溶性樹脂(i)−2を得た。得られた樹脂の固形分濃度は61.1質量%、酸価(固形分換算)は120.4mgKOH/g、および分子量(Mw)は3230であった。
還留冷却器付き1000ml四つ口フラスコ中に、HBPA−EA2の50%PGMEA溶液(338.2g)と、BPDA(36.8g)と、THPA(19.0g)と、TEAB(0.43g)と、PGMEA(8.5g)と、仕込み、120〜125℃で6時間撹拌し、アルカリ可溶性樹脂(i)−3を得た。得られた樹脂の固形分濃度は73.8質量%、酸価(固形分換算)は93.0mgKOH/g、および分子量(Mw)は4980であった。
還留冷却器付き1000ml四つ口フラスコ中に、HBPA−EA2の50%PGMEA溶液(338.2g)と、HPMDA(28.0g)と、THPA(19.0g)と、TEAB(0.43g)と、PGMEA(8.5g)と、を仕込み、120〜125℃で6時間撹拌し、アルカリ可溶性樹脂(i)−4を得た。得られた樹脂の固形分濃度は64.2質量%、酸価(固形分換算)は100.8mgKOH/g、および分子量(Mw)は3960であった。
還留冷却器付き1000ml四つ口フラスコ中に、BPA−EAの50%PGMEA溶液(325.1g)と、BPDA(45.6g)と、THPA(23.6g)と、TEAB(0.43g)と、PGMEA(8.5g)と、を仕込み、120〜125℃で加熱下に6時間撹拌し、アルカリ可溶性樹脂(i)−5を得た。得られた樹脂の固形分濃度は68.5質量%、酸価(固形分換算)は113.0mgKOH/g、および分子量(Mw)は2080であった。
還留冷却器付き1000ml四つ口フラスコ中にBPA−EAの50%PGMEA溶液(335.6g)と、HPMDA(35.9g)と、THPA(24.3g)と、TEAB(0.43g)と、PGMEA(8.5g)と、を仕込み、120〜125℃で6時間撹拌し、アルカリ可溶性樹脂(i)−6を得た。得られた樹脂の固形分濃度は69.5質量%、酸価(固形分換算)は116.5mgKOH/g、および分子量(Mw)は2630であった。
還留冷却器付き1000ml四つ口フラスコ中に、BPF−EAの50%PGMEA溶液(313.7g)と、BPDA(47.1g)と、THPA(24.3g)と、TEAB(0.43g)と、PGMEA(8.5g)と、仕込み、120〜125℃で6時間撹拌し、アルカリ可溶性樹脂(i)−7を得た。得られた樹脂の固形分濃度は56.55質量%、酸価(固形分換算)は103.0mgKOH/g、および分子量(Mw)は3600であった。
(i)−2 :上記合成例2で得られたアルカリ可溶性樹脂
(i)−3 :上記合成例3で得られたアルカリ可溶性樹脂
(i)−4 :上記合成例4で得られたアルカリ可溶性樹脂
(i)−5 :上記比較合成例1で得られたアルカリ可溶性樹脂
(i)−6 :上記比較合成例2で得られたアルカリ可溶性樹脂
(i)−7 :上記比較合成例3で得られたアルカリ可溶性樹脂
(ii) :ジペンタエリスリトールヘキサアクリレート
(iii) :Irgacure184(BASF社製、「Irgacure」は同
社の登録商標)
(iv) :カーボンブラック20.0質量%、高分子分散剤5.0質量%のP
GMEA分散液(固形分25.0%、カーボンブラックの平均二次
粒径162nm)
(v) :プロピレングリコールモノメチルエーテルアセテート
表1に、合成例1〜4、比較例1および2の感光性樹脂組成物溶液の各成分の含有量(単位は質量%)を示す。
実施例1〜4、比較例1および2の感光性樹脂組成物溶液を、ガラス板上にスピンコ−タ−を用いて1.5μmの乾燥膜厚になる条件で塗布・乾燥した後、フォトマスクを介さずに500Wの高圧水銀灯ランプを用いて波長365nmの照度10mW/cm2の紫外線を照射して露光した。露光後、0.4%炭酸ナトリウム水溶液を用いて23℃で60秒間0.1MPaの圧力で現像液処理を行った。その後、熱風乾燥機を用いて230℃で30分間、加熱硬化処理を行い、硬化膜(硬化膜を形成したガラス基板)を得た。
分光光度計「UH−4150」(株式会社日立ハイテクサイエンス製)を用いて、400nmにおける光透過率を測定した。
評価は下記の基準で行った。
○:光透過率は85%以上である
×:光透過率は85%未満である
プリズムカップラー膜厚・屈折計「モデル2010/M」(メトリコン社製)を用いて、633nmの光線の屈折率を測定した。なお、測定した屈折率は表2に示している。
表3に、合成例5〜8、比較例3および4の着色感光性樹脂組成物溶液の各成分の含有量(単位は質量%)を示す。
実施例5〜8および比較例3、4の着色感光性樹脂組成物溶液を、ガラス板上にスピンコ−タ−を用いて1.5μmの乾燥膜厚になる条件で塗布・乾燥した後、フォトマスクを介さずに500Wの高圧水銀灯ランプを用いて波長365nmの照度10mW/cm2の紫外線を照射して露光した。露光後、0.4%炭酸ナトリウム水溶液を用いて23℃で60秒間0.1MPaの圧力で現像液処理を行った。その後、熱風乾燥機を用いて230℃で30分間加熱硬化処理を行い、着色硬化膜(着色硬化膜を形成したガラス基板)を得た。
分光光度計「UH−4150」(株式会社日立ハイテクサイエンス製)を用いて、Y値を測定した。
着色硬化膜表面の外観を目視で確認した。
◎:色ムラが全く確認されない
〇:表面の1/4以下の領域に色ムラが観察される
△:表面の1/3以下の領域に色ムラが観察される
×:全体に色ムラが観察される
実施例5〜8、比較例3および4の着色感光性樹脂組成物溶液を、ガラス板上にスピンコ−タ−を用いて1.5μmの乾燥膜厚になる条件で塗布・乾燥した後、パターン形成用のマスクを介して500Wの高圧水銀灯ランプを用いて波長365nmの照度10mW/cm2の紫外線を照射して露光した。露光後、23℃の0.15%炭酸ナトリウム水溶液を用いて現像液処理を行った。その後、熱風乾燥機を用いて230℃で30分間加熱硬化処理を行い、着色硬化膜(着色硬化膜を形成したガラス基板)を得た。
現像時において、乾燥した着色感光性樹脂組成物の薄膜が現像液に溶解するかどうかを目視で確認した。
○:現像時において、紫外線を照射していない領域が現像液に溶解する
×:現像時において、紫外線を照射していない領域が現像液に溶解しないか、破片
として剥離する
レジスト膜パターンの細線形成を光学顕微鏡「ECLIPSE LV100」(株式会社Nikon製)で確認した。
○:L/S(ライン幅/スペース幅)が20μm/20μm以上のパターンが残渣
なく形成されているもの
×:L/S(ライン幅/スペース幅)が20μm/20μm未満のパターンが形成
されていないか、パターンの裾引きや残渣が目立つもの
Claims (12)
- 請求項1に記載の製造方法で得られた重合性不飽和基含有アルカリ可溶性樹脂のカルボキシ基に対して、さらにカルボキシ基に反応する基と、重合性不飽和基と、を有する化合物を反応させる、重合性不飽和基含有アルカリ可溶性樹脂の製造方法。
- 請求項2に記載の製造方法で得られた重合性不飽和基含有アルカリ可溶性樹脂の水酸基に対して、さらにジカルボン酸もしくはトリカルボン酸またはそれらの酸一無水物を反応させる、重合性不飽和基含有アルカリ可溶性樹脂の製造方法。
- 式(2)で表される構造を有する、請求項1〜3のいずれか一項に記載の製造方法で得られる、重合性不飽和基含有アルカリ可溶性樹脂。
- (A)請求項4に記載の重合性不飽和基含有アルカリ可溶性樹脂と、
(B)光重合開始剤と、
を含む、感光性樹脂組成物。 - (C)少なくとも1個の重合性不飽和基を有する光重合性モノマーと、
任意成分である(D)エポキシ基を2つ以上有するエポキシ化合物またはエポキシ樹脂と、
を含む、請求項5に記載の感光性樹脂組成物。 - (E)分散質を含有する、請求項5または請求項6に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物の固形分中、(A)成分は1〜55質量%であり、(C)成分は前記(A)成分100質量部に対して0〜100質量部であり、(B)成分は前記(A)成分と前記(C)成分との合計量100質量部に対して0.1〜40質量部であり、(E)成分は1〜95質量%である、請求項7に記載の感光性樹脂組成物。
- 前記(A)成分は、
前記式(2)で表される重合性不飽和基含有アルカリ可溶性樹脂と、
式(5)で表される樹脂と、
を含み、
前記式(2)で表される重合性不飽和基含有アルカリ可溶性樹脂の質量mA−1と、前記式(5)で表される樹脂の質量mA−2との比率は、mA−1/mA−2=75/25〜25/75である、請求項5〜8のいずれか一項に記載の感光性樹脂組成物。
- 請求項5〜9のいずれか一項に記載の感光性樹脂組成物をフォトリソグラフィー法によりパターニングし、前記パターニングした感光性樹脂組成物を硬化してなる硬化物。
- 請求項10に記載の硬化物を構成成分として含む、タッチパネル。
- 請求項10に記載の硬化物を構成成分として含む、カラーフィルター。
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