JPWO2014185303A1 - チオキサンテン系化合物、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
チオキサンテン系化合物、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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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(1)水素化リチウムアルミニウムでチオキサントン誘導体のカルボニル基を還元して、9H−チオキサンテン誘導体を得る。なお、市販品の9H−チオキサンテン誘導体がある場合には、かかる市販品をそのまま用いてもよい。
(2)メタクロロ過安息香酸(mCPBA)でチオキサンテン環の硫黄原子を酸化して、スルフィニル基又はスルホニル基に変換する。
(3)ホルムアルデヒドを用いてヒドロキシメチル化する。
(4)ジイソシアン酸によりアミド結合を形成する(R3、R8、R13が水素原子のものに限る。)。
(5)クロロぎ酸−4−ニトロフェニルまたはトリホスゲンと反応させ、カルボニル基を活性化させる。
(6)活性カルボニル化合物とアミンを反応させ、目的物を得る。
中間体の製造(1):
500mL三つ口フラスコに脱水テトラヒドロフラン100mLを入れ、そこに攪拌しながら水素化リチウムアルミニウム3.2g(50×10−3mol)をゆっくり加えた。この溶液を氷浴下で攪拌させながら、この溶液に塩化アルミニウム11.2g(168×10−3mol)を脱水テトラヒドロフラン100mLに溶解させた溶液をゆっくり滴下した。その後、下記式(H−1)で表される2,4−ジエチルチオキサントン13.0g(48×10−3mol)を少量ずつ反応系に加え、30分間還流攪拌した。反応終了後、フラスコに酢酸エチルを加えた後、5質量%HClaqをゆっくり注入し残留物を溶解させ、ジクロロメタンで抽出した。有機層をNaHCO3aq、NaClaqによって各3回ずつ洗浄し、最後に硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣を減圧乾燥することで、下記式(H−2)で表される化合物の黄色粘性液体を収量11.0g(収率92%)で得た。
中間体の製造(2):
500mLナスフラスコに式(H−2)で表される中間体11.0g(44×10−3mol)を入れ、ジクロロメタン150mLに溶解させた。この溶液に、m−クロロ過安息香酸8.6g(50.0×10−3mol)を加え、室温で12時間攪拌した。反応終了後、反応液を飽和重曹水、飽和食塩水で各3回ずつ洗浄し、最後に有機層を硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣を減圧乾燥することで、下記式(H−3)で表される中間体の黄色固体を収量11.0g(収率95%)で得た。
中間体の製造(3):
100mL二つ口ナスフラスコに式(H−3)で表される中間体1.0g(3.7×10−3mol)、p−ホルムアルデヒド0.47g(15×10−3mol)を入れ窒素雰囲気下にし、脱水テトラヒドロフラン30mLを入れ、氷浴下にした。ここに1mol/L水酸化カリウムのメタノール溶液をゆっくり滴下し、滴下終了後20分間還流攪拌した。反応終了後、反応液にジクロロメタンで加えて抽出し、有機層を5質量%HClaq、NaHSO3aq、NaClaqで各3回ずつ洗浄し、最後に有機層を硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=2:1)で精製することで、下記式(H−4)で表される化合物の黄色固体を収量0.75g(収率67%)で得た。
中間体の製造(4):
100mLナスフラスコに式(H−4)で表される中間体2.4g(7.9×10−3mol)を入れ、ジクロロメタン15mLに溶解させた。ここにm−クロロ過安息香酸1.5g(8.7×10−3mol)を加え、室温で12時間攪拌した。反応終了後、反応液に飽和重曹水、飽和食塩水を少量ずつ入れ、ジクロロメタンで抽出し、最後に有機層を硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣を減圧乾燥することで、下記式(H−5)で表される中間体の黄色固体を収量2.3g(収率95%)で得た。
中間体の製造(5):
200mLナスフラスコに式(H−5)で表される中間体2.0g(6.3×10−3mmol)とピリジン0.51g(6.4×10−3mmol)を入れ、脱水テトラヒドロフラン15mLを加えた。撹拌しながら脱水テトラヒドロフラン15mLに溶解させたクロロぎ酸−4−ニトロフェニル(NP−Cl)1.7g(6.4×10−3mmol)をゆっくり滴下し、室温で6時間撹拌した。反応終了後、反応液の溶媒を留去後、クロロホルムを加えて抽出し、有機層を5質量%HClaq、NaHCO3aq、NaClaqで各3回ずつ洗浄し、最後に有機層に硫酸マグネシウムで乾燥させた。次いで、溶媒留去後、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=2:1)で精製することで、下記式(H−6)で表される中間体の黄色固体を収量2.4g(収率79%)で得た。
塩基増殖剤の製造(1):
50mLナスフラスコに式(H−4)で表される中間体0.22g(0.74×10−3mol)とピリジン0.05g(0.74×10−3mol)を入れ、脱水テトラヒドロフラン10mlを加えた。撹拌しながら脱水テトラヒドロフラン15mLに溶解させたクロロぎ酸−4−ニトロフェニル(NP−Cl)0.15g(0.74×10−3mol)をゆっくり滴下し、室温で4時間撹拌した。反応終了後、この溶液に、ピペリジン0.06g(0.70×10−3mol)を脱水テトラヒドロフラン1mLに溶解させた溶液を滴下し、室温で3時間攪拌した。反応終了後、反応液にジクロロメタンを加えて抽出し、有機層をHClaq、NaHSO3aq、NaClaqで各3回ずつ洗浄し、最後に有機層を硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=2:1)で精製することで、下記式(A−a)で表される塩基増殖剤の白色固体を収量0.22g(収率72%)で得た。
塩基増殖剤の製造(2):
50mLナスフラスコに式(H−6)で表される中間体0.50g(1.0×10−3mol)を脱水テトラヒドロフラン20mLに溶解させた。この溶液に、ピペリジン0.09g(1.0×10−3mol)を脱水テトラヒドロフラン1mLに溶解させた溶液を滴下し室温で12時間攪拌した。反応終了後、反応液に酢酸エチルを加えて抽出し、有機層をNaHSO3aq、NaClaqで各3回ずつ洗浄し、最後に有機層を硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=4:1)で精製することで、下記式(A−b)で表される塩基増殖剤の淡黄色固体を収量0.31g(収率70%)で得た。
塩基増殖剤の製造(3):
200mLナスフラスコに式(H−4)で表される中間体0.50g(1.7×10−3mol)とジラウリン酸ジブチルすず(IV)0.12g(0.2×10−3mol)を入れ、ベンゼン30mLとアセトニトリル20mLを加え溶解させた。撹拌しながらベンゼン1mLに溶解させたジイソシアン酸ヘキサメチレン0.14g(0.83×10−3mol)を滴下し、13時間撹拌した。反応終了後、反応液の溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=3:1)で精製することで、下記式(A−c)で表される塩基増殖剤の白色固体を収量0.35g(収率54%)で得た。
塩基増殖剤の製造(4):
300mLナスフラスコに式(H−5)で表される中間体1.0g(3.2×10−3mol)とジラウリン酸ジブチルすず(IV)0.18g(0.3×10−3mol)を入れ、ベンゼン50mLを加え溶解させた。撹拌しながらベンゼン1mLに溶解させたジイソシアン酸ヘキサメチレン0.50g(3.0×10−3mol)を滴下し、13時間撹拌した。反応終了後、反応液の溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=2:1)で精製することで、下記式(A−d)で表される塩基増殖剤の白色固体を収量0.50g(収率20%)で得た。
塩基増殖剤の製造(5):
300mLナスフラスコに式(H−5)で表される中間体2.5g(7.9×10−3mol)とジラウリン酸ジブチルすず(IV)0.42g(0.7×10−3mol)を入れ、ベンゼン30mLを加え溶解させた。撹拌しながらベンゼン1mLに溶解させたジイソシアン酸イソホロン(イソホロンジイソシアナート)0.89g(4.0×10−3mol)を滴下し、70℃で13時間撹拌した。反応終了後、反応液の溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;ヘキサン:酢酸エチル=3:1)で精製することで、下記式(A−e)で表される塩基増殖剤の白色固体を収量1.40g(収率40%)で得た。
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、前記したスキームに示すように、塩基の添加により分解反応が起こり、塩基及び二酸化炭素(CO2)とともに、オレフィンが生成する。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1で得られた塩基増殖剤70×10−3mol/L、塩基であるピペリジン13×10−3mol/L、溶媒として重メタノール(メタノール−d4)、内部標準液としてメシチレン13×10−3mol/Lを入れ、封管した後100℃で所定の時間加熱した。そして、1H−NMRにより、生成する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。加熱時間と塩基増殖剤の転化率及びオレフィンの生成率との関係を図13に示す。なお、オレフィンの生成率は、1H−NMRスペクトルより算出した。また、図13において、実線は塩基増殖剤の転化率を表し、破線はオレフィンの生成率を表す。
有機溶剤に対する溶解性の確認:
実施例3及び実施例4で得られた塩基増殖剤の有機溶剤に対する溶解性を確認した。結果を図14に示す。なお、塩基増殖剤の溶解性は、塩基増殖剤0.01gに対して溶解する溶媒量を算出することで確認した。図14中、溶解量の結果を、溶媒量が1mL未満の場合(溶媒を1mL必要としないで溶解した場合)を「++」、2〜5mLの場合「+」、6〜9mLの場合「−」、10mLを超える場合「−−」として示した。また、比較として、下記式(S−1)及び式(S−2)で表される化合物(順に、比較例1及び比較例2とする。)もあわせて評価した。
塩基反応性樹脂組成物(感光性樹脂組成物)の製造(1):
式(No.4−13)に表される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(デナコール(登録商標)EX−622/ナガセケムテックス(株)製)0.1gに対して、式(E−2)で表される光塩基発生剤を0.031g(エポキシ系化合物100質量部に対して31質量部)(アミン官能基比率:10mol%(対エポキシ基))、実施例5で得られた塩基増殖剤を下記の含有量で含有させることにより本発明の塩基反応性樹脂組成物(感光性樹脂組成物)を得た。
含有量(g) 質量部 アミン官能基比率(注)
実施例6 0.15 150 40mol%
実施例7 0.23 230 60mol%
実施例8 0.31 310 80mol%
(注)対エポキシ基(mol%)
樹脂組成物の製造(1)
実施例6において、実施例5で得られた塩基増殖剤を添加しなかった以外は、実施例6と同様の方法を用いて、樹脂組成物を得た。
硬化確認(1)(添加量依存性の確認):
実施例6で得られた塩基反応性樹脂組成物を0.1gのクロロホルム(CHCl3)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、60℃で1分間加熱してプリベイクし、厚さ5.0μm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、5000及び10000mJ/cm2として、ポストベイクとして80℃で40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った。そして、同様な操作を、実施例7、実施例8及び参考例1の塩基反応性樹脂組成物等に対して実施し、比較・評価した。露光量と鉛筆硬度との関係を図15に示す。
硬化確認(2)(加熱時間依存性の確認):
実施例7で得られた塩基反応性樹脂組成物を0.1gのクロロホルム(CHCl3)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、60℃で1分間加熱してプリベイクし、厚さ5.0μm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、5000及び10000mJ/cm2として、ポストベイクとして80℃で10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った。そして、同様な操作を、ポストベイクの加熱時間を20分、40分及び60分として実施し、比較・評価した。露光量と鉛筆硬度との関係を図16に示す。
硬化確認(3)(加熱温度依存性の確認):
実施例7で得られた塩基反応性樹脂組成物を0.1gのクロロホルム(CHCl3)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、60℃で1分間加熱してプリベイクし、厚さ5.0μm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、5000及び10000mJ/cm2として、ポストベイクとして60℃で40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った。そして、同様な操作を、ポストベイクの加熱温度を80℃及び100℃として実施し、比較・評価した。露光量と鉛筆硬度との関係を図17に示す。
中間体の製造(6):
200mL4つ口フラスコに式(H−5)10.0g(31.6×10−3mmol)と炭酸ナトリウム3.35g(31.6×10−3mmol)を入れ、脱水テトラヒドロフラン60mLを加えた。撹拌しながら脱水テトラヒドロフラン60mLに溶解させたトリホスゲン6.19g(20.8×10−3mmol)をゆっくり滴下し、室温で48時間撹拌した。反応終了後、生じた塩を濾過で除き、溶媒留去した。得られた粗体にジイソプロピルエーテルを加え洗浄し、減圧乾燥を行い下記式(H−7)で表される中間体の白色固体を収量5.9g(収率49%)で得た。
塩基増殖剤の製造(6):
200mL4つ口フラスコに式(H−7)で表される中間体5.90g(15.57×10−3mol)と炭酸水素ナトリウム4.32g(51.38×10−3mol)を入れ、水5ml、ジメトキシエタン10mLを加えた。撹拌しながらジエチレントリアミン0.54g(5.19×10−3mol)を滴下し、室温で3時間撹拌した。反応終了後、酢酸エチル10mLを加え、有機層をHClaqで洗浄後、水で3回洗浄し、有機層を硫酸マグネシウムで乾燥させた。次いで、エバポレーターにより溶媒を留去し、得られた残渣にイソプロピルアルコール20mLとジイソプロピルエーテル20mLを加え、洗浄後、脱液、減圧乾燥することで、下記式(A−f)で表される塩基増殖剤の白色粉末を収量4.18g(収率71%)で得た。
塩基反応性樹脂組成物(感光性樹脂組成物)の製造(2):
式(No.4−11)に表されるエポキシ系化合物であるビスフェノールジグリシジルエーテルオリゴマー(jER828(登録商標)/三菱化学(株)製、エポキシ当量185)0.1gに対して、式(E−4)で表される光塩基発生剤を0.017g(エポキシ系化合物100質量部に対して17質量部)、実施例9で得られた塩基増殖剤を0.16g(アミン官能基比率:80mоl%(対エポキシ基))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。
樹脂組成物の製造(2)
実施例10において、実施例9で得られた塩基増殖剤を添加しなかった以外は、実施例10と同様の方法を用いて、樹脂組成物を得た。
硬化確認(4):
実施例10で得られた塩基反応性樹脂組成物を0.1gのクロロホルム(CHCl3)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、60℃で1分間加熱してプリベイクし、厚さ5.0μm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、5000及び10000mJ/cm2として、ポストベイクとして100℃で40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った。そして、同様な操作を、参考例2の樹脂組成物に対して実施し、比較・評価した。露光量と鉛筆硬度との関係を図18に示す。
Claims (9)
- 下記式(A)で表されることを特徴とする化合物。
(式(A)中、R1、R2及びR3はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基または炭素数7〜15のアリールアルキル基を示し、Qは水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基、炭素数7〜15のアリールアルキル基、下記式(B1)で表される基または下記式(B2)で表される基を示し、R3及びQは互いに結合して環構造を形成してもよい。X1はSOまたはSO2を示し、Y1、Y2、Y3、Y4、Z1、Z2、Z3及びZ4はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基、炭素数7〜15のアリールアルキル基、炭素数1〜12のハロアルキル基、ハロゲン原子またはニトロ基を示す。ただし、Y1、Y2、Y3、Y4、Z1、Z2、Z3及びZ4がすべて水素原子である場合を除く。)
(式(B1)中、D1は下記式(V1)または下記式(V2)を示し、D2は下記式(V1)または下記式(V3)を示す。R8、R9及びR10はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基または炭素数7〜15のアリールアルキル基を示す。前記式(A)のR3、D1が下記式(V2)である場合のm1個のR4及びR5、D2が下記式(V3)である場合のm2個のR6及びR7、並びにR8は、これらのRのうち、少なくとも2つのRが互いに結合して環構造を形成してもよい。n1は0〜20の整数を示し、X2はSOまたはSO2を示し、Y5、Y6、Y7、Y8、Z5、Z6、Z7及びZ8はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基、炭素数7〜15のアリールアルキル基、炭素数1〜12のハロアルキル基、ハロゲン原子またはニトロ基を示す。)
(式(B2)中、D1は下記式(V1)または下記式(V2)を示し、D2は下記式(V1)または下記式(V3)を示し、D3は下記式(V1)または下記式(V4)を示す。R8、R9、R10、R13、R14及びR15はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基または炭素数7〜15のアリールアルキル基を示す。前記式(A)のR3、D1が下記式(V2)である場合のm1個のR4及びR5、D2が下記式(V3)である場合のm2個のR6及びR7、R8、D3が下記式(V4)である場合のm3個のR11及びR12、並びにR13は、これらのRのうち、少なくとも2つのRが互いに結合して環構造を形成してもよい。n1、n2及びn3はそれぞれ独立して、0〜20の整数を示し、wは0または1を示し、X2及びX3はそれぞれ独立して、SOまたはSO2を示し、Y5、Y6、Y7、Y8、Y9、Y10、Y11、Y12、Z5、Z6、Z7、Z8、Z9、Z10、Z11及びZ12はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基、炭素数7〜15のアリールアルキル基、炭素数1〜12のハロアルキル基、ハロゲン原子またはニトロ基を示す。)
(式(V2)中、m1個のR4及びR5はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基または炭素数7〜15のアリールアルキル基を示し、m1は1〜7の整数を示す。)
(式(V3)中、m2個のR6及びR7はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基または炭素数7〜15のアリールアルキル基を示し、m2は1〜7の整数を示す。)
(式(V4)中、m3個のR11及びR12はそれぞれ独立して、水素原子、炭素数1〜12のアルキル基、炭素数5〜10のシクロアルキル基、炭素数6〜14のアリール基または炭素数7〜15のアリールアルキル基を示し、m3は1〜7の整数を示す。) - 請求項1ないし請求項4のいずれか1項に記載の化合物からなることを特徴とする塩基増殖剤。
- 請求項5に記載の塩基増殖剤と、塩基反応性化合物と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5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と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7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6ないし請求項8のいずれか1項に記載の塩基反応性樹脂組成物。
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Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6078979A (ja) * | 1983-08-30 | 1985-05-04 | リサ−チ・コ−ポレイシヨン | チオキサンチルメチルオキシカルボニルジオキシド類を用いるペプチド合成法 |
JPS61236822A (ja) * | 1985-04-11 | 1986-10-22 | チバ‐ガイギー アーゲー | 放射感応性重縮合物、その製造方法、被覆物質およびその用途 |
JP2000212464A (ja) * | 1999-01-28 | 2000-08-02 | Fuji Photo Film Co Ltd | 色素前駆体、画像形成材料、および画像形成方法 |
JP2000330270A (ja) * | 1999-05-24 | 2000-11-30 | Kunihiro Ichimura | 塩基増殖剤、塩基増殖剤組成物、塩基反応性組成物及びパターン形成方法 |
JP2002128750A (ja) * | 2000-10-24 | 2002-05-09 | Kunihiro Ichimura | 塩基増殖性プレポリマー |
JP2002265531A (ja) * | 2001-03-13 | 2002-09-18 | Kunihiro Ichimura | 塩基増殖性不飽和化合物、塩基増殖性樹脂及び該樹脂を含む組成物 |
JP2003073579A (ja) * | 2001-08-31 | 2003-03-12 | Fuji Photo Film Co Ltd | 色素形成材料、画像形成材料および画像形成方法 |
JP2007241205A (ja) * | 2006-03-10 | 2007-09-20 | Koji Arimitsu | 感活性エネルギー線塩基発生剤、感活性エネルギー線塩基発生剤組成物、塩基反応性組成物及びパターン形成方法 |
WO2010064632A1 (ja) * | 2008-12-02 | 2010-06-10 | 和光純薬工業株式会社 | 光塩基発生剤 |
JP2010133996A (ja) * | 2008-12-02 | 2010-06-17 | Dainippon Printing Co Ltd | 感光性樹脂組成物、およびこれを用いた物品、及びネガ型パターン形成方法 |
-
2014
- 2014-05-02 JP JP2015517037A patent/JP6280919B2/ja active Active
- 2014-05-02 WO PCT/JP2014/062198 patent/WO2014185303A1/ja active Application Filing
- 2014-05-13 TW TW103116850A patent/TW201446750A/zh unknown
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6078979A (ja) * | 1983-08-30 | 1985-05-04 | リサ−チ・コ−ポレイシヨン | チオキサンチルメチルオキシカルボニルジオキシド類を用いるペプチド合成法 |
JPS61236822A (ja) * | 1985-04-11 | 1986-10-22 | チバ‐ガイギー アーゲー | 放射感応性重縮合物、その製造方法、被覆物質およびその用途 |
JP2000212464A (ja) * | 1999-01-28 | 2000-08-02 | Fuji Photo Film Co Ltd | 色素前駆体、画像形成材料、および画像形成方法 |
JP2000330270A (ja) * | 1999-05-24 | 2000-11-30 | Kunihiro Ichimura | 塩基増殖剤、塩基増殖剤組成物、塩基反応性組成物及びパターン形成方法 |
JP2002128750A (ja) * | 2000-10-24 | 2002-05-09 | Kunihiro Ichimura | 塩基増殖性プレポリマー |
JP2002265531A (ja) * | 2001-03-13 | 2002-09-18 | Kunihiro Ichimura | 塩基増殖性不飽和化合物、塩基増殖性樹脂及び該樹脂を含む組成物 |
JP2003073579A (ja) * | 2001-08-31 | 2003-03-12 | Fuji Photo Film Co Ltd | 色素形成材料、画像形成材料および画像形成方法 |
JP2007241205A (ja) * | 2006-03-10 | 2007-09-20 | Koji Arimitsu | 感活性エネルギー線塩基発生剤、感活性エネルギー線塩基発生剤組成物、塩基反応性組成物及びパターン形成方法 |
WO2010064632A1 (ja) * | 2008-12-02 | 2010-06-10 | 和光純薬工業株式会社 | 光塩基発生剤 |
JP2010133996A (ja) * | 2008-12-02 | 2010-06-17 | Dainippon Printing Co Ltd | 感光性樹脂組成物、およびこれを用いた物品、及びネガ型パターン形成方法 |
Non-Patent Citations (3)
Title |
---|
ARIMITSU, KOJI; ET AL.: "Nonlinear organic reaction of 9-fluorenylmethyl carbamates as base amplifiers to proliferate aliphat", JOURNAL OF MATERIALS CHEMISTRY, vol. Vol.14(3), JPN6014023379, 2004, pages 336 - 343, ISSN: 0003663291 * |
CARPINO, LOUIS A.; ET AL.: "Thioxanthene dioxide based amino-protecting groups sensitive to pyridine bases and dipolar aprotic s", JOURNAL OF ORGANIC CHEMISTRY, vol. Vol.54(25), JPN6014023382, 1989, pages 5887 - 5897, ISSN: 0003663293 * |
OKABAYASHI, ICHIZO; ET AL.: "Synthesis of xanthene derivatives having antispasmodic action. IX. Derivatives of xanthene- and thi", 薬学雑誌, vol. Vol.92(11), JPN6014023384, 1972, pages 1390 - 1394, ISSN: 0003663292 * |
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