JP7021668B2 - トリアジンペルオキシド誘導体、該化合物を含有する重合性組成物 - Google Patents
トリアジンペルオキシド誘導体、該化合物を含有する重合性組成物 Download PDFInfo
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- JP7021668B2 JP7021668B2 JP2019522081A JP2019522081A JP7021668B2 JP 7021668 B2 JP7021668 B2 JP 7021668B2 JP 2019522081 A JP2019522081 A JP 2019522081A JP 2019522081 A JP2019522081 A JP 2019522081A JP 7021668 B2 JP7021668 B2 JP 7021668B2
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- -1 Triazine peroxide Chemical class 0.000 title claims description 119
- 239000000203 mixture Substances 0.000 title claims description 85
- 150000001875 compounds Chemical class 0.000 title claims description 72
- 239000003505 polymerization initiator Substances 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 25
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- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 230000001678 irradiating effect Effects 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 51
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
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- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 7
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- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 6
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- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- WIOADUFWOUUQCV-UHFFFAOYSA-N triphenylphosphanium dichloride Chemical compound [Cl-].[Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 WIOADUFWOUUQCV-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/36—Per-compounds with more than one peroxy radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Materials For Photolithography (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Description
本発明のトリアジンペルオキシド誘導体は、下記一般式(1)で表すことができる。
(式(2)中、mは0から3の整数を表し、R4は、独立した置換基であって、炭素数1~18のアルキル基、一般式(3):R5-Y-で表される置換基、ニトロ基、またはシアノ基を表し、前記Yは、酸素原子または硫黄原子を表し、前記R5は、炭素骨格中に、エーテル結合、チオエーテル結合、および、末端に水酸基のいずれか1つ以上を有していてもよい炭素数1~18の炭化水素基、アルキル基を有してもよい炭素数6~9の芳香族炭化水素基、または炭素数1~8のアシル基を表す。あるいは、R4は隣接する2つの前記一般式(3):R5-Y-により5~6員環を形成する炭化水素基を表す。)
前記一般式(1)で表されるトリアジンペルオキシド誘導体の製造方法は、例えば、下記反応式のように、塩化シアヌル誘導体を得る工程(以下、工程(A)とも称す)と、続いて、得られた塩化シアヌル誘導体と、ヒドロペルオキシドを、アルカリの存在下で、反応させる工程(以下、工程(B)とも称す)を含む方法が挙げられる。なお、上記の工程(A)および/または(B)の後には、余剰の原料等を減圧留去(除去)する工程や、精製工程を含んでもよい。
前記工程(A)において、グリニャール反応により、塩化シアヌル誘導体を合成する場合、特開平6-179661号公報等に記載の公知の合成法に準じて合成することができる。前記工程(A)における芳香族化合物のZは塩素原子、臭素原子、またはヨウ素原子で表される芳香族化合物を使用することができる。芳香族化合物とマグネシウムを反応させることでグリニャール試薬を調整し、次いで得られたグリニャール試薬を塩化シアヌルと反応させることにより塩化シアヌル誘導体を合成することができる。
前記工程(A)において、リチオ化反応により、塩化シアヌル誘導体を合成する場合、WO2012/096263公報等に記載の公知の合成法に準じて合成することができる。前記工程(A)における芳香族化合物のZは塩素原子、臭素原子、またはヨウ素原子で表される芳香族化合物を使用することができる。芳香族化合物とリチオ化剤を反応させることでリチオ化合物を調整し、次いで得られたリチオ化合物と塩化シアヌルを反応させることにより塩化シアヌル誘導体を合成することができる。
前記工程(A)において、鈴木カップリング反応により、塩化シアヌル誘導体を合成する場合、WO2012/096263公報等に記載の公知の合成法に準じて合成することができる。例えば、前述のリチオ化合物をホウ素試薬と反応させることによって、芳香族化合物のZがボロニル基またはボロン酸に変換されたホウ素化合物を合成することができる。次いで得られたホウ素化合物を塩化シアヌルと反応させることにより塩化シアヌル誘導体を合成することができる。なお、ホウ素化合物の市販品が販売されている場合、そのまま使用することができる。
前記工程(A)において、フリーデル・クラフツ反応により、塩化シアヌル誘導体を合成する場合、US5322941公報等に記載の公知の合成法に準じて合成することができる。前記工程(A)における芳香族化合物のZは水素原子、n=0で表される芳香族化合物を使用することができる。塩化アルミニウム等のルイス酸の存在下、芳香族化合物と塩化シアヌルを反応させることにより塩化シアヌル誘導体を合成することができる。
前記工程(B)において、一般式(1)で表されるトリアジンペルオキシド誘導体の製造方法は、特に限定されないが、特公昭45-39468号公報等に記載の公知のトリアジンペルオキシドの合成法に準じて合成することができる。
本発明の重合性組成物は、(a)重合開始剤および(b)ラジカル重合性化合物を含有する。さらに、重合性組成物は、(c)アルカリ可溶性樹脂を含有することで現像性を付与することができる。また、重合性組成物は、その他の成分を適宜組み合わせて含有させることができる。
本発明の(a)重合開始剤は、前記一般式(1)で表されるトリアジンペルオキシド誘導体を含有する。(a)重合開始剤は、活性エネルギー線または熱により分解し、発生したラジカルが(b)ラジカル重合性化合物の重合(硬化)を開始する働きを有する。トリアジンペルオキシド誘導体は、単独で用いてもよく2種類以上を併用してもよい。
本発明の(b)ラジカル重合性化合物としては、エチレン性不飽和基を有する化合物を好ましく用いることができる。(b)ラジカル重合性化合物としては、例えば、(メタ)アクリル酸エステル類、スチレン類、マレイン酸エステル類、フマル酸エステル類、イタコン酸エステル類、桂皮酸エステル類、クロトン酸エステル類、ビニルエーテル類、ビニルエステル類、ビニルケトン類、アリルエーテル類、アリルエステル類、N-置換マレイミド類、N-ビニル化合物類、不飽和ニトリル類、オレフィン類等が挙げられる。これらの中でも、反応性が高い(メタ)アクリル酸エステル類を含むことが好ましい。(b)ラジカル重合性化合物は、単独で用いてもよく2種類以上を併用してもよい。
前記重合性組成物は、さらに(c)アルカリ可溶性樹脂を配合することにより、ネガ型レジストとして好適に使用することができる。(c)アルカリ可溶性樹脂としては、ネガ型レジストに一般的に使用されるものを用いることができ、アルカリ水溶液に可溶な樹脂であれば特に限定されないが、カルボキシル基を含む樹脂であることが好ましい。(c)アルカリ可溶性樹脂は、単独で用いてもよく2種類以上を併用してもよい。
前記その他の成分として、硬化促進剤を用いることで、重合性組成物の加熱による硬化を低温で行なうこともできる。硬化促進剤としては、例えば、アミン化合物、チオ尿素化合物、2-メルカプトベンズイミダゾール系化合物、オルトベンゾイックスルフィミド、第4周期遷移金属化合物合物等を使用することができる。硬化促進剤は、単独で用いてもよく2種類以上を併用してもよい。
前記重合性組成物を調整する場合には、収納容器内に前記(a)重合開始剤、前記(b)ラジカル重合性化合物、必要に応じて、前記(c)アルカリ可溶性樹脂や前記その他の成分を投入し、ペイントシェーカー、ビーズミル、サンドグラインドミル、ボールミル、アトライターミル、2本ロールミル、3本ロールミル等を用いて、常法に従って溶解または分散させればよい。また、必要に応じて、メッシュまたはメンブレンフィルター等を通してもろ過してもよい。
本発明の硬化物は、前記重合性組成物から形成されるものである。硬化物の製造方法は、重合性組成物を基板上に塗布後、当該重合性組成物を活性エネルギー線で照射する工程、および当該重合性組成物を加熱する工程のいずれかの工程を含む製造方法である。また、前記活性エネルギー線で照射する工程と前記加熱する工程の両方を含む工程を、デュアルキュア工程ともいう。
前記重合性組成物が(c)アルカリ可溶性樹脂を含む場合、フォトリソグラフィー法によりパターンを形成することができる。前述と同様にして重合性組成物を基材に塗布し、必要に応じて、乾燥して乾燥被膜を形成する。そして、乾燥被膜にマスクを介して活性エネルギー線を照射することにより、露光部では(b)ラジカル重合性化合物が重合することで硬化膜となる。一方、レーザーを用いた直接描画により、マスクを介さずに高精度なパターン形状を作製することもできる。
(1)トリアジンペルオキシド誘導体の合成
[合成例1:化合物1の合成]
20mLナスフラスコにイオン交換水1.66g、48質量%水酸化ナトリウム水溶液0.553g(6.64mmol)を加え、30℃以下で69質量%tert-ブチルヒドロペルオキシド水溶液0.698g(5.31mmol)を徐々に加えた。ここに、2,4-ジクロロ-6-フェニル-1,3,5-トリアジン0.500g(2.21mmol、ナミキ商事より購入)とテトラヒドロフラン1mLの混合溶液を、10℃で10分かけて滴下し、20℃にて3.5時間反応させた。反応終了後、ジクロロメタン10mLを添加した後に、水相を分液した。油相をイオン交換水で洗浄し、0℃にて無水硫酸マグネシウムで乾燥した。ろ過後、油相を減圧下で濃縮し、0.683g(収率92%)の本発明の化合物1を得た。得られた化合物1の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
ヒートドライ乾燥した500mL三つ口フラスコに、マグネシウム1.69g(69.5mmol)、脱水テトラヒドロフラン57mL、触媒量のヨウ素を入れ、室温下で撹拌した。ここに、1-ブロモナフタレン7.07g(50.7mmol)と脱水テトラヒドロフラン57mLの混合溶液を滴下した後、還流撹拌させた。1時間後、内温を-60℃以下まで冷却した。別途調整した塩化シアヌル8.92g(48.4mmol)と脱水テトラヒドロフランの混合溶液を15分かけ滴下した。その後、30分かけて室温にあげ、水浴下で撹拌した。62時間後、反応液を氷浴で冷却し、1M塩酸を加え、飽和炭酸水素ナトリウム水溶液でpHを8に調整した。次いで、イオン交換水160mLを加え、酢酸エチルで抽出した。油相を飽和食塩水で1回洗浄した後、硫酸マグネシウムで脱水した。ろ過後、油相を減圧下で濃縮し、粗体14.6gを得た。粗体をシリカゲルカラムクロマトグラフィー(n-ヘキサン/酢酸エチル=1/1から1/3)で精製し、5.14g(収率38%)の2,4-ジクロロ-6-(1-ナフタレニル)-1,3,5-トリアジンを得た。
300mLナスフラスコに、1-メトキシナフタレン5.01g(31.7mmol)、脱水ジクロロメタン100mL、塩化シアヌル6.12g(33.2mmol)を入れ、氷浴下撹拌した。15分後、塩化アルミニウム4.43g(33.2mmol)を加え、室温に昇温した。1時間後、反応液を氷冷1M塩酸75mLに注ぎ、水相を分液した。油相を飽和食塩水100mLで洗浄し、無水硫酸ナトリウムにて脱水した。ろ過後、減圧濃縮し、粗体を9.59gの黄色固体を得た。粗体をシリカゲルカラムクロマトグラフィー(n-ヘキサン/トルエン=4/1から1.5/1)で精製し、8.05g(収率83%)の2,4-ジクロロ-6-(4-メトキシ-1-ナフタレニル)-1,3,5-トリアジンを得た。
本発明の化合物4は、合成例2に記載の1-ブロモナフタレンを、2-ブロモ-6-メトキシナフタレンに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物26の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物4は、合成例1に記載の2,4-ジクロロ-6-フェニル-1,3,5-トリアジンを、2,4-ジクロロ-6-(4-エトキシ-1-ナフタレニル)-1,3,5-トリアジン(シグマアルドリッチ試薬)に変更したこと以外は、合成例1に記載の方法に準じて合成した。得られた化合物31の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物32は、合成例3に記載の69質量%tert-ブチルヒドロペルオキシド水溶液を、85質量%tert-アミルヒドロペルオキシドに変更したこと以外は、合成例3に記載の方法に準じて合成した。得られた化合物32の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物33は、合成例1に記載の2,4-ジクロロ-6-フェニル-1,3,5-トリアジンを、2-(4-ビフェニリル)-4,6-ジクロロ-1,3,5-トリアジン(東京化成工業試薬)に変更したこと以外は、合成例1に記載の方法に準じて合成した。得られた化合物33の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物35は、合成例2に記載の1-ブロモナフタレンを、4-ブロモ-4’-メトキシビフェニルに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物35の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物37は、合成例2に記載の1-ブロモナフタレンを、4-ブロモ-4’-メトキシビフェニルに、及び69質量%tert-ブチルヒドロペルオキシド水溶液を85質量%tert-アミルヒドロペルオキシドに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物37の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物38は、合成例2に記載の1-ブロモナフタレンを、4-ブロモ-4’-メトキシビフェニル、及び69質量%tert-ブチルヒドロペルオキシド水溶液を90質量%tert-ヘキシルヒドロペルオキシドに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物38の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物40は、合成例2に記載の1-ブロモナフタレンを、4-ブロモ-4’-メトキシビフェニルに、及び69質量%tert-ブチルヒドロペルオキシド水溶液を80質量%クメンヒドロペルオキシドに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物40の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物41は、合成例2に記載の1-ブロモナフタレンを、4-ブロモスチルベンに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物41の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
100mLナスフラスコに、塩化シアヌル5.70g(10mmol)、trans-フェニルビニルボロン酸1.56g(30mmol、シグマアルドリッチ試薬)、ビス(トリフェニルホスフィン)ジクロリド0.31g(0.4mmol)、トルエン40mLを入れ、室温で撹拌した。リン酸三カリウム8.68g(40mmol)の水溶液10mLを0℃で滴下した。滴下終了後、室温で1時間の反応を行った。反応終了後、水相を分液した。油相を飽和食塩水で1回洗浄した後、硫酸マグネシウムで脱水した。ろ過後、油相を減圧下で濃縮し粗体を得た。粗体をシリカゲルカラムクロマトグラフィーで精製し、2.08g(収率78%)の2,4-ジクロロ-6-(2-フェニルエテニル)-1,3,5-トリアジンを得た。
本発明の化合物35は、合成例2に記載の1-ブロモナフタレンを、p-(2-ブロモ)ビニルアニソールに変更したこと以外は、合成例2に記載の方法に準じて合成した。得られた化合物41の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物5は、合成例3に記載の1-メトキシナフタレンを、アニソールに変更したこと以外は、合成例3に記載の方法に準じて合成した。得られた化合物5の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物19は、合成例3に記載の1-メトキシナフタレンを、ジフェニルスルフィドに変更したこと以外は、合成例3に記載の方法に準じて合成した。得られた化合物19の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
本発明の化合物48は、合成例3に記載の1-メトキシナフタレンを、1-(2-エチルヘキシルオキシ)ナフタレンに変更したこと以外は、合成例3に記載の方法に準じて合成した。得られた化合物19の性状、EI-MSおよび1H-NMRによる分析結果を表1および表2に示す。
表1に記載される化合物のアセトニトリル溶液について、UV-VISスペクトル測定装置(1.0cm石英セル、島津製作所製、UV-2450)を用いて、波長200から600nmにおけるUV-VISスペクトルを測定した。その結果を表3に示す。
また、比較例として、化合物R1および化合物R2の結果を表3に示す。なお、化合物R1は特開昭59-197401号公報に記載の製法に準じて合成し、EI-MSおよび1H-NMRによって同定した。化合物R2はイルガキュア184(BASF製)を使用した。
<重合性組成物(A)から(C)の調整>
表4に示す量の(b)ラジカル重合性化合物、(c)アルカリ可溶性樹脂、その他の成分を混合撹拌し、(a)重合開始剤を添加してよく撹拌し、実施例18~34および比較例3~5の重合性組成物(A)から(C)を調整した。
RD200は、メタクリル酸メチル/メタクリル酸/シクロヘキシルマレイミド(質量%:61/14/25)共重合物、重量平均分子量:17,000、酸価:90(合成品);
EMK:4,4‘-ビス(ジエチルアミノ)ベンゾフェノン(東京化成工業試薬)
F-477は、フッ素系レベリング剤(商品名:メガファックF-477、DIC社製);
PGMEAは、プロピレングリコールモノメチルエーテルアセテート(和光純薬工業試薬);を示す。
上記で調整した重合性組成物(A)を、スピンコーターを用いて、アルミニウム基板上に塗布した。塗布後、アルミニウム基板を90℃のクリーンオーブン中で2.5分間乾燥処理により溶媒を乾燥させ、厚さ1.5μmの均一な塗布膜を作製した。次いで、超高圧水銀灯を光源とするプロキシミティー露光機を用い、マスクパターンを介して10から1000mJ/cm2の範囲で、段階露光を行った。露光後のアルミニウム基板を1.0質量%の炭酸ナトリウム水溶液に23℃で60秒間浸漬して、現像による未露光部の除去を行った。続いて純水にて30秒間洗浄を行い、パターン形状を得た。パターン形状が形成される最低露光量を「感度」として評価した。各(a)重合開始剤の評価結果を、表5に示す。
<重合性組成物(D)の調整>
表6に示す量の(b)ラジカル重合性化合物、硬化促進剤を混合撹拌し、(a)重合開始剤を添加してよく撹拌し、実施例29および比較例6の重合性組成物(B)を調整した。
IBOAは、イソボルニルアクリレート(東京化成工業試薬);
THFAは、テトラヒドロフルフリルアクリレート(東京化成工業試薬);
TMPTAは、トリメチロールプロパントリアクリレート(東京化成工業試薬);
DMTは、N,N-ジメチルトルイジン(東京化成工業試薬);を示す。
上記で調整した重合性組成物(D)を、厚さ100μmの易接着処理されたPETフィルム(商品名:コスモシャインA4300、東洋紡社製)に、アプリケーターにて50μmに塗布し、表面に黒色コーティングが施されたPETフィルム(波長365nmの透過率は0.1%未満)を被膜の半分の領域に設置した。そして、高圧水銀ランプが設置されたコンベア式UV照射装置を使用して100mJ/cm2の照射を行った。次いで、送風定温恒温機内に静置し、90℃で90分の加熱を行った。
<重合性組成物(E)の調整>
表8に示す量の(b)ラジカル重合性化合物、(c)アルカリ可溶性樹脂、その他の成分を混合撹拌し、(a)重合開始剤を添加してよく撹拌し、実施例36~39および比較例7~8の重合性組成物(E)を調整した。また、比較例のハロメチルトリアジン誘導体である化合物R3および化合物R4は東京化成試薬を使用した。
上記で調整した重合性組成物(E)を、スピンコーターを用いて、ガラス基板上に塗布した。塗布後、ガラス基板を90℃のクリーンオーブン中で2.5分間乾燥処理により溶媒を乾燥させ、厚さ1.5μmの均一な塗布膜を作製した。そして、高圧水銀ランプが設置されたコンベア式UV照射装置を使用して300mJ/cm2の照射を行い、試験片を作製した。得られた試験片の硬化度を測定した結果、すべての試験片において硬化度は90%以上であった。得られた試験片について、分光測色計(CM-3500d、ミノルタカメラ製)を用いてL*,a*,b*表色系の値をJIS-Z-8722に従って、透過法にて測定した。b*の値を黄色度の指標として評価し、b*が小さいほど黄色度が低い。その結果を表9に示す。
Claims (7)
- 一般式(1):
- 前記一般式(2)中、R4は、独立した置換基であって、炭素数1から8のアルキル基、または一般式(3):R5-Y-で表される置換基を表し、前記Yは、酸素原子を表し、前記R5は、炭素骨格中に、エーテル結合、および、末端に水酸基のいずれか1つ以上を有していてもよい炭素数1~8の炭化水素基、またはアルキル基を有してもよい炭素数6~9の芳香族炭化水素基を表し、あるいは、R4は隣接する2つの前記一般式(3):R5-Y-により5~6員環を形成する炭化水素基を表すことを特徴とする請求項1記載のトリアジンペルオキシド誘導体。
- 請求項1または請求項2記載のトリアジンペルオキシド誘導体を含む(a)重合開始剤、および(b)ラジカル重合性化合物を含有することを特徴とする重合性組成物。
- さらに(c)アルカリ可溶性樹脂を含有することを特徴とする請求項3記載の重合性組成物。
- 請求項3または請求項4記載の重合性組成物から形成されることを特徴とする硬化物。
- 前記重合性組成物を活性エネルギー線で照射する工程を含むことを特徴とする請求項5記載の硬化物の製造方法。
- 前記活性エネルギー線で照射する工程の後、さらに、加熱する工程を含むことを特徴とする請求項6記載の硬化物の製造方法。
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