JP6572213B2 - 新規重合開始剤及び該重合開始剤を含有するラジカル重合性組成物 - Google Patents
新規重合開始剤及び該重合開始剤を含有するラジカル重合性組成物 Download PDFInfo
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- JP6572213B2 JP6572213B2 JP2016538318A JP2016538318A JP6572213B2 JP 6572213 B2 JP6572213 B2 JP 6572213B2 JP 2016538318 A JP2016538318 A JP 2016538318A JP 2016538318 A JP2016538318 A JP 2016538318A JP 6572213 B2 JP6572213 B2 JP 6572213B2
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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- C08F2/00—Processes of polymerisation
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- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
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Description
しかし、特許文献1〜3に記載のα−アミノアルキルフェノン誘導体は昇華性が十分に低くなく、昇華物によるフォトマスクや加熱炉の汚染等の原因となっていた。
R3及びR4は、それぞれ独立に、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表し、R3とR4は、連結して3〜6員環の環状アルカンを形成してもよく、
R5、R6、R7及びR8は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基を表し、
R9、R10、R11、R12及びR13は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基、−OR14、−O−CO−O−R15、−NR16R17、−SR18を表し、かつ、R9、R10、R11、R12及びR13のうち少なくとも1つは、ニトロ基、−OR14、−O−CO−O−R15、−NR16R17、−SR18の群より選ばれる基であり、
R14、R15、R16、R17及びR18は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基;炭素原子数2〜12の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、
上記アルキル基及びアリールアルキル基中のメチレン鎖は、−O−、−S−、−NR19−、−CO−、−CO−O−、−O−CO−又は−O−CO−O−で置き換えられていてもよく、上記アルキル基の末端は不飽和結合であってもよく、
R19は、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表す。
上記一般式(I)中の、R1、R2、R3、R4、R14、R15、R16、R17、R18及びR19で表される、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている炭素原子数1〜12のアルキル基としては、上記炭素原子数1〜12のアルキル基の一部又は全部が、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているものが挙げられる。
上記一般式(I)中の、R5、R6、R7、R8、R9、R10、R11、R12及びR13で表されるハロゲン原子で置換されている炭素原子数1〜8のアルキル基としては、上記炭素原子数1〜8のアルキル基の一部又は全部が、ハロゲン原子で置換されているものが挙げられる。
上記一般式(I)中の、R1、R2、R5、R6、R7、R8、R9、R10、R11、R12及びR13で表される、炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている炭素原子数7〜30のアリールアルキル基としては、上記炭素原子数7〜30のアリールアルキル基の一部又は全部が、炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているものが挙げられる。
上記一般式(I)中の、R3、R4、R14、R15、R16、R17及びR18で表される、炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている炭素原子数7〜30のアリールアルキル基としては、上記炭素原子数7〜30のアリールアルキル基の一部又は全部が、炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているものが挙げられる。
また、上記一般式(I)中の、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18及びR19で表される基のアルキル(アルキレン)部分は、分岐側鎖があってもよく、環状アルキルであってもよく、また、アルキル基の末端が2重結合、3重結合の不飽和結合であってもよい。
これらの中でも、両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート、1個のカルボキシ基と2個以上の(メタ)アクリロイル基とを有する多官能(メタ)アクリレート、不飽和一塩基酸及び多価アルコール又は多価フェノールのエステルに、本発明のα−アミノアルキルフェノン化合物を含有する重合開始剤は好適である。
これらの重合性化合物は、単独で又は2種以上を混合して使用することができ、また2種以上を混合して使用する場合には、それらを予め共重合して共重合体として使用してもよい。
これらの中でも、下記一般式(III)で表されるエポキシ化合物のエポキシ基に、不飽和一塩基酸を作用させ、更に多塩基酸無水物を作用させて得られた樹脂が好ましい。
また、上記エチレン性不飽和結合を有していてもよいアルカリ現像性を有する化合物は、不飽和基を0.2〜1.0当量含有していることが好ましい。
のアルコキシ基により置換されていてもよいフェニル基、又は炭素原子数1〜10のアルキル基若しくは炭素原子数1〜10のアルコキシ基により置換されていてもよい炭素原子数3〜10のシクロアルキル基を示し、Y1は炭素原子数1〜10のアルキル基、炭素原
子数1〜10のアルコキシ基、炭素原子数2〜10のアルケニル基又はハロゲン原子を示し、上記アルキル基、アルコキシ基及びアルケニル基はハロゲン原子で置換されていてもよく、dは0〜5の整数である。)
即ち、上記エポキシ化合物のエポキシ基1個に対し、上記不飽和一塩基酸のカルボキシル基が0.1〜1.0個で付加させた構造を有するエポキシ付加物において、該エポキシ付加物の水酸基1個に対し、上記多塩基酸無水物の酸無水物構造が0.1〜1.0個となる比率となるようにするのが好ましい。
上記エポキシ化合物、上記不飽和一塩基酸及び上記多塩基酸無水物の反応は、常法に従って行なうことができる。
上記のエチレン性不飽和結合を有する重合性化合物と、上記のエチレン性不飽和基を有していてもよいアルカリ現像性を有する化合物とは同一の化合物であってもよく、異なっていても良く、また、単独であっても2種以上を併用してもよい。
上記ビスフェノール型エポキシ化合物としては、上記一般式(III)で表されるエポキシ化合物を用いることができる他、例えば、水添ビスフェノール型エポキシ化合物等のビスフェノール型エポキシ化合物も用いることができる。
また上記グリシジルエーテル類としては、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、1,8−オクタンジオールジグリシジルエーテル、1,10−デカンジオールジグリシジルエーテル、2,2−ジメチル−1,3−プロパンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、テトラエチレングリコールジグリシジルエーテル、ヘキサエチレングリコールジグリシジルエーテル、1,4−シクロヘキサンジメタノールジグリシジルエーテル、1,1,1−トリ(グリシジルオキシメチル)プロパン、1,1,1−トリ(グリシジルオキシメチル)エタン、1,1,1−トリ(グリシジルオキシメチル)メタン、1,1,1,1−テトラ(グリシジルオキシメチル)メタン等を用いることができる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4−エポキシ−6−メチルシクロヘキシルメチル−3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、1−エポキシエチル−3,4−エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジルP−アミノフェノール、N,N−ジグリシジルアニリン等のグリシジルアミン類;1,3−ジグリシジル−5,5−ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物;トリフェニルメタン型エポキシ化合物;ジシクロペンタジエン型エポキシ化合物等を用いることもできる。
これらの中でも、ケトン類、エーテルエステル系溶媒等、特にプロピレングリコール−1−モノメチルエーテル−2−アセテート、シクロヘキサノン等が、ラジカル重合性組成物において、レジストと重合開始剤の相溶性がよいので好ましい。
これらの中でも、ガラスフリット、酸化チタン、シリカ、層状粘土鉱物、銀等が好ましい。本発明のラジカル重合性組成物において、上記無機化合物の含有量は、上記エチレン性不飽和結合を有する重合性化合物100質量部に対して、好ましくは0.1〜1000質量部、より好ましくは10〜800質量部である。尚、これらの無機化合物は1種又は2種以上を使用することができる。
他の光重合開始剤としては、従来既知の化合物を用いることが可能であり、例えば、ベンゾフェノン、フェニルビフェニルケトン、1−ヒドロキシ−1−ベンゾイルシクロヘキサン、ベンゾイン、ベンジルジメチルケタール、1−ベンジル−1−ジメチルアミノ−1−(4'−モルホリノベンゾイル)プロパン、2−モルホリル−2−(4'−メチルメルカプト)ベンゾイルプロパン、チオキサントン、1−クロル−4−プロポキシチオキサントン、イソプロピルチオキサントン、ジエチルチオキサントン、エチルアントラキノン、4−ベンゾイル−4'−メチルジフェニルスルフィド、ベンゾインブチルエーテル、2−ヒドロキシ−2−ベンゾイルプロパン、2−ヒドロキシ−2−(4'−イソプロピル)ベンゾイルプロパン、4−ブチルベンゾイルトリクロロメタン、4−フェノキシベンゾイルジクロロメタン、ベンゾイル蟻酸メチル、1,7−ビス(9'−アクリジニル)ヘプタン、9−n−ブチル−3,6−ビス(2'−モルホリノイソブチロイル)カルバゾール、2−メチル−4,6−ビス(トリクロロメチル)−s−トリアジン、2−フェニル−4,6−ビス(トリクロロメチル)−s−トリアジン、2−ナフチル−4,6−ビス(トリクロロメチル)−s−トリアジン、2,2−ビス(2−クロロフェニル)−4,5,4’,5’−テトラフェニル−1−2’−ビイミダゾール、4、4−アゾビスイソブチロニトリル、トリフェニルホスフィン、カンファーキノン、N−1414、N−1717、N−1919、NCI−831、NCI−930(ADEKA社製)、IRGACURE369、IRGACURE907、IRGACURE OXE 01、IRGACURE OXE 02(BASF社製)、TR−PBG−304、TR−PBG−305、TR−PBG−314(Tronly社製)、過酸化ベンゾイル、下記一般式(IV)で表される化合物等が挙げられ、これらの他の光重合開始剤を使用する場合、その使用量は、好ましくは本発明のα−アミノアルキルフェノン化合物の使用量の1質量倍以下とする。尚、これらの光重合開始剤は、1種又は2種以上を組み合わせて用いることができる。
R23及びR24は、それぞれ独立に、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R25、OR26、SR27、NR28R29、COR30、SOR31、SO2R32又はCONR33R34を表し、R23及びR24は、互いに結合して環を形成していてもよく、
R25、R26、R27、R28、R29、R30、R31、R32、R33及びR34は、それぞれ独立に、炭素原子数1〜20のアルキル基、炭素原子数6〜30のアリール基、炭素原子数7〜30のアリールアルキル基又は炭素原子数2〜20の複素環基を表し、
X2は、酸素原子、硫黄原子、セレン原子、CR35R36、CO、NR37又はPR38を表し、
X3は、単結合又はCOを表し、
R21、R22、R25、R26、R27、R28、R29、R30、R35、R36、R37及びR38中の炭素原子数1〜20のアルキル基、炭素原子数6〜30のアリール基又は炭素原子数7〜30のアリールアルキル基を表し、該アルキル基又はアリールアルキル基中のメチレン基は、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基又は複素環基で置換されていてもよく、−O−で中断されていてもよく、
R35、R36、R37及びR38は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよく、
aは、0〜4の整数を表し、
bは、0〜5の整数を表す。)
他の有機重合体を使用する場合、その使用量は、上記エチレン性不飽和結合を有する重合性化合物100質量部に対して、好ましくは10〜500質量部である。
ここで、アルキルエーテルを構成するアルキル基としては、メチル基、エチル基又はブチル基が挙げられ、互いに同一であってもよいし、異なっていてもよい。また、アルキルエーテル化されていないメチロール基は、一分子内で自己縮合していてもよく、二分子間で縮合して、その結果オリゴマー成分が形成されていてもよい。
具体的には、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン、テトラメトキシメチルグリコールウリル、テトラブトキシメチルグリコールウリル等を用いることができる。
これらの中でも、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン等のアルキルエーテル化されたメラミンが好ましい。
(A)ジオ−ル化合物と多価カルボン酸類とを反応させて得られ、重量平均分子量が2,000〜40,000、酸価が50〜200mgKOH/gであるカルボキシル基含有樹脂、
(B)光重合可能なエチレン性不飽和結合を一分子中に少なくとも1つ以上含む不飽和化合物、
(C)エポキシ化合物、及び
(D)上記一般式(I)で表されるα-アミノアルキルフェノン化合物を含有する重合開始剤、
を主成分とする樹脂組成物であって、
(A)成分と(B)成分の合計100重量部に対して、(C)成分が10〜40重量部、(D)成分が0.1〜20重量部含有するものが好ましい。
ハロゲン体1の1.0eq.をジメチルスルホキシド11.0eq.に溶解させ、炭酸カリウム3.0eq.及びチオール化合物1の1.3eq.を入れ、窒素雰囲気下70℃で16時間加熱撹拌した。室温まで冷却後、酢酸エチルから抽出した。溶媒を留去し、粗生成物をメタノール:イオン交換水=1:1から再結晶し、乾燥して下記の〔化19〕で表される中間体1(収率22.9%)を得た。
中間体1の1.0eq.をo-キシレン14.0eq.に溶解させ、エチレンカーボネート1.1eq.及び炭酸カリウム0.02eq.を入れ、窒素雰囲気下、140℃で18時間撹拌した。室温まで冷却後、酢酸エチルで抽出した。溶媒を留去し、粗生成物をシリカカラムクロマトグラフィー(n−ヘキサン:酢酸エチル=1:1)で精製し、乾燥して化合物No.5(収率69.0%)を得た。
尚、本製造例においては、ハロゲン体1として、[化6]中のハロゲン体1において、R1及びR2がモルホリン環を形成しており、R3及びR4がメチル基であり、R5、R6、R7及びR8が水素であり、かつXが臭素であるものを用いた。また、チオール化合物1は[化6]中のチオール化合物1において、R9、R10、R12及びR13は水素であり、かつR11が水酸基であるものを用いた。
分析結果を〔表1〕〜〔表3〕に示す。
100ml四つ口フラスコに、実施例1−1で得られた中間体1の1.0eq.を入れ、酢酸エチル7.0eq.を加えて溶解させた。ジメチルアミノピリジン0.4eq.及びジ−t−ブチルジカーボネート1.5eq.を加え、窒素雰囲気下室温で4時間撹拌した。反応液をイオン交換水で3回洗浄した後、溶媒を留去した。粗生成物をn−ヘキサンに溶解させ、減圧乾燥し溶媒を完全に除去して化合物No.8(収率41.6%)を得た。
分析結果を〔表1〕〜〔表3〕に示す。
50ml四つ口フラスコに、実施例1−1で得られた中間体1の1.0eq.を入れ、テトラヒドロピラン32.4eq.に溶解させた。2,6−ジ−t−ブチル−4−ヒドロキシトルエン0.005eq.を加えて氷冷下撹拌した。トリエチルアミン1.7eq.を滴下し、続いて、メタクリル酸クロリド1.7eq.を滴下した。氷冷下4時間撹拌した後、酢酸エチルで抽出した。溶媒を留去し、粗生成物をシリカカラムクロマトグラフィー(n−ヘキサン:酢酸エチル=5:1)で精製し、乾燥して化合物No.41(収率43.1%)を得た。
分析結果を〔表1〕〜〔表3〕に示す。
50ml四つ口フラスコに実施例1−1で得られた中間体1の1.0eq.を入れ、ジメチルアセトアミド14.3eq.で溶解させた。炭酸プロピレン1.1eq.及び炭酸カリウム0.02eq.を加え、150℃で10時間撹拌した。室温まで冷却後、酢酸エチルで抽出し、イオン交換水で2回洗浄した。溶媒を留去し、粗生成物をシリカカラムクロマトグラフィー(n−ヘキサン:酢酸エチル=1:1)で精製し、乾燥して化合物No.42(収率42.4%)を得た。
分析結果を〔表1〕〜〔表3〕に示す。
SPC−1000(アクリル樹脂;昭和電工社製)54.84g、アロニックスM−450(多官能アクリレート;東亜合成社製)12.77g、KBE−403(シランカップリング剤;信越シリコーン社製)0.57g、FZ−2122(界面活性剤;日本ユニカー社製)のシクロヘキサノン1%溶液3.19g及びプロピレングリコール−1−モノメチルエーテル−2−アセテート27.95gを混合し、混合液から14.805g量り取り、実施例1−1〜1−4で得られた化合物No.5、No.8、No.41又はNo.42の0.195gを添加してよく撹拌し、本発明のラジカル重合性組成物であるラジカル重合性組成物No.1〜No.4を得た。
実施例1−1で得られた化合物No.5を2−モルホリル−2−(4'−メチルメルカプト)ベンゾイルプロパンに替えた以外は実施例1と同様の手法で、比較ラジカル重合性組成物No.1を得た。
化合物No.5、No.41及びNo.42並びに比較化合物(2−モルホリル−2−(4'−メチルメルカプト)ベンゾイルプロパン)の昇華性評価を以下のようにして行った。
即ち、化合物2.5mgを窒素雰囲気下150℃で1時間保持し、重量減少の割合を算出し、昇華性評価とした。試験結果を〔表4〕に示す。
得られたラジカル重合性組成物No.1〜No.4及び比較ラジカル重合性組成物No.1の放射線感度評価を以下のようにして行った。
即ち、ガラス基板上にラジカル重合性組成物をスピンコートし、ホットプレートを用いて、90℃で90秒間プリベークを行い、光源としてi線バンドパスフィルターを備えた高圧水銀ランプを用いてマスクを介して露光した。現像液として2.5質量%炭酸ナトリウム水溶液を用い現像後、よく水洗し、オーブンを用いて、230℃で30分ポストベークを行い、パターンを定着させた。パターンを電子顕微鏡で観察し、20μm開口のパターンが残った最少露光量をi線感度とした。尚、露光量が〜200mJ/cm2の時はA、200〜500mJ/cm2の時はB、500mJ/cm2の時はCとした。試験結果を〔表5〕に示す。
Claims (7)
- 下記一般式(I)で表されるα−アミノアルキルフェノン化合物を含有する重合開始剤。
R3及びR4は、それぞれ独立に、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表し、R3とR4は、連結して3〜6員環の環状アルカンを形成してもよく、
R5、R6、R7及びR8は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基を表し、
R9、R10、R11、R12及びR13は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基、−OR14、−O−CO−O−R15、−NR16R17、−SR18を表し、かつ、R9、R10、R11、R12及びR13のうち少なくとも1つは、ニトロ基、−OR14、−O−CO−O−R15、−NR16R17、−SR18の群より選ばれる基であり、
R 15、R16、R17及びR18は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基;炭素原子数2〜12の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、
R 14 は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている炭素原子数1〜12のアルキル基;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基;炭素原子数2〜12の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、
上記アルキル基及びアリールアルキル基中のメチレン鎖は、−O−、−S−、−NR19−、−CO−、−CO−O−、−O−CO−又は−O−CO−O−で置き換えられていてもよく、上記アルキル基の末端は不飽和結合であってもよく、
R19は、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表す。) - 上記一般式(I)において、R11がニトロ基又は炭素原子数1〜12のアルコキシカルボニル基であることを特徴とする請求項1記載の重合開始剤。
- 上記一般式(I)において、R 11 が−OR 14 であることを特徴とする請求項1記載の重合開始剤。
- 重合開始剤(A)及びエチレン性不飽和結合を有する重合性化合物(B)を含有するラジカル重合性組成物において、
重合開始剤(A)が請求項1〜3の何れか1項に記載の重合開始剤であることを特徴とするラジカル重合性組成物。 - 請求項4に記載のラジカル重合性組成物にエネルギー線を照射してなる硬化物。
- 下記一般式(II)で表されるα-アミノアルキルフェノン化合物。
R3及びR4は、それぞれ独立に、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表し、R3とR4は、連結して3〜6員環の環状アルカンを形成してもよく、
R5、R6、R7及びR8は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基を表し、
R9、R10、R11、R12及びR13は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基、−O−CO−O−R15、−NR16R17、−SR18を表し、かつ、R9、R10、R11、R12及びR13のうち少なくとも1つは、ニトロ基、−O−CO−O−R15、−NR16R17、−SR18の群より選ばれる基であり、
R15、R16、R17及びR18は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基;炭素原子数2〜12の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、
上記アルキル基及びアリールアルキル基中のメチレン鎖は−S−、−CO−、−CO−O−、−O−CO−又は−O−CO−O−で置き換えられていてもよく、上記アルキル基の末端は不飽和結合であってもよい。) - 下記一般式(I)で表されるα−アミノアルキルフェノン化合物。
R 3 及びR 4 は、それぞれ独立に、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表し、R 3 とR 4 は、連結して3〜6員環の環状アルカンを形成してもよく、
R 5 、R 6 、R 7 及びR 8 は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基を表し、
R 9 、R 10 、R 11 、R 12 及びR 13 は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、カルボキシル基、水酸基;ハロゲン原子で置換されている若しくは無置換の炭素原子数1〜8のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基、−OR 14 、−O−CO−O−R 15 、−NR 16 R 17 、−SR 18 を表し、かつ、R 9 、R 10 、R 11 、R 12 及びR 13 のうち少なくとも1つは、ニトロ基、−OR 14 、−O−CO−O−R 15 、−NR 16 R 17 、−SR 18 の群より選ばれる基であり、
R 15 、R 16 、R 17 及びR 18 は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基;炭素原子数2〜12の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、
R 14 は、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されている炭素原子数1〜12のアルキル基;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、炭素原子数1〜4のアルコキシ基、アミノ基、炭素原子数1〜4のアルキルチオ基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基;炭素原子数2〜12の複素環含有基、トリアルキルシリル基又はトリアリールシリル基を表し、
上記アルキル基及びアリールアルキル基中のメチレン鎖は、−O−、−S−、−NR 19 −、−CO−、−CO−O−、−O−CO−又は−O−CO−O−で置き換えられていてもよく、上記アルキル基の末端は不飽和結合であってもよく、
R 19 は、水素原子;水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数1〜12のアルキル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換のフェニル基;炭素原子数1〜4のアルキル基、水酸基、カルボキシル基、ハロゲン原子、シアノ基若しくはニトロ基で置換されているかあるいは無置換の炭素原子数7〜30のアリールアルキル基;炭素数2〜12のアルケニル基を表す。)
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