JP7482628B2 - オキシムエステル化合物及び該化合物を含有する光重合開始剤 - Google Patents
オキシムエステル化合物及び該化合物を含有する光重合開始剤 Download PDFInfo
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- JP7482628B2 JP7482628B2 JP2019505981A JP2019505981A JP7482628B2 JP 7482628 B2 JP7482628 B2 JP 7482628B2 JP 2019505981 A JP2019505981 A JP 2019505981A JP 2019505981 A JP2019505981 A JP 2019505981A JP 7482628 B2 JP7482628 B2 JP 7482628B2
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- -1 Oxime ester compound Chemical class 0.000 title claims description 153
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 39
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 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 4
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 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
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- 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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- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- 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
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- 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
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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Description
更に、光重合開始剤は、各種用途に用いる際に有機溶剤に溶解して用いられるため、有機溶剤への溶解性が高いことも求められる。
R1、R2、R3、R4、R5及びR6のうち、少なくとも一つが下記一般式(II)で表される基であり、
R7、R8、R9、R10及びR11は、それぞれ独立に、下記一般式(IIIα)で表される基、下記一般式(IIIβ)で表される基、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R21、OR21、SR21、NR22R23、COR21、SOR21、SO2R21又はCONR22R23を表し、
R7、R8、R9、R10及びR11のうち、少なくとも一つが下記一般式(IIIα)で表される基又は下記一般式(IIIβ)で表される基であり、
R21、R22及びR23は、それぞれ独立に、炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環含有基を表し、
R21、R22及びR23で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、炭素原子数2~20の炭化水素基又は炭素原子数2~20の複素環含有基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR24-、-NR24CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、R24は、水素原子又は炭素原子数1~20の炭化水素基を表し、
X1は、不存在、直接結合、-CO-、-O-又は-S-を表し、
R1とR2、R2とR3、R3とR4、R5とR6、R6とR7、R7とR8、R8とR9、R9とR10、R10とR11、及びR11とR1は、結合して環を形成する場合がある。)
R31及びR32で表される炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環含有基の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、R31及びR32で表される炭素原子数2~20の炭化水素基又は炭素原子数2~20の複素環含有基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR33-、-NR33CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、R33は、水素原子又は炭素原子数1~20の炭化水素基を表し、
nは0又は1を表し、*は結合手を表す。)
R51、R52及びR53は、それぞれ独立に、炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環含有基を表し、
R51、R52及びR53で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、炭素原子数2~20の炭化水素基又は炭素原子数2~20の複素環含有基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR54-、-NR54CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、
X2及びX3は、-O-、-S-又は-NR54-を表し、
R54は、水素原子又は炭素原子数1~20の炭化水素基を表し、
*は結合手を表す。)
R101、R102、R103、R104、R105、R106、R107及びR108のうち、少なくとも一つが上記一般式(II)で表される基であり、
R109、R110、R111、R112及びR113は、それぞれ独立に、上記一般式(IIIα)で表される基、上記一般式(IIIβ)で表される基、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R121、OR121、SR121、NR122R123、COR121、SOR121、SO2R121又はCONR122R123を表し、
R109、R110、R111、R112及びR113のうち、少なくとも一つが下記一般式(IIIα)で表される基又は下記一般式(IIIβ)で表される基であり、
R121、R122及びR123は、それぞれ独立に、炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環含有基を表し、
R121、R122及びR123で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環含有基で置換される場合があり、炭素原子数2~20の炭化水素基又は炭素原子数2~20の複素環含有基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR124-、-NR124CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、
R124は、水素原子又は炭素原子数1~20の炭化水素基を表し、
X101は、不存在、直接結合、-CO-、-O-又は-S-を表し、
R101とR102、R102とR103、R103とR104、R105とR106、R106とR107、R107とR108、R108とR109、R109とR110、R110とR111、R111とR112、R112とR113及びR113とR101は、結合して環を形成する場合がある。)
即ち、本明細書において、上記一般式(Iα)又は(Iβ)で表わされる化合物及びその例示化合物は、これら幾何異性体の1種又は2種以上の混合物を表すものであり、構造を示した特定の異性体に限定されるものではない。
また、本発明のオキシムエステル化合物の中でも、一般式(Iβ)中のR103及びR106の少なくとも一つが、一般式(II)で表される基であるオキシムエステル化合物は、合成時に収率がよく、精製も容易なことから好ましい。同様の観点から、一般式(Iβ)中のR103及びR106の両方が、一般式(II)で表される基であるオキシムエステル化合物も好ましい。
また、上記一般式(Iα)及び(Iβ)において、R6及びR108が一般式(II)で表される基以外の基又は原子である場合、R6及びR108が水素原子であるものは、合成が容易なので好ましい。
尚、本明細書において、「X1が不存在」とは、一般式(Iα)において、-X1-で表される結合が存在せず、N原子及びX1を含む縮合環骨格が形成されていない状態を意味する。例えば、上述の「X1が不存在でR5とR6が結合してベンゼン環を形成するであるオキシムエステル化合物」は、N原子及びX1を含む縮合環骨格ではなくトリフェニルアミン骨格を有する化合物であり、該化合物の具体例としては後記の化合物No.153~170が挙げられる。
また、一般式(Iβ)中の「X101が不存在」とは、-X101-で表される結合が存在せず、N原子及びX101を含む縮合環骨格が形成されていない状態を意味する。
上記一般式(Iβ)で表される本発明のオキシムエステル化合物においては、R111が上記一般式(IIIα)で表される基であることが好ましい。また、上記一般式(Iβ)で表される本発明のオキシムエステル化合物においては、R111が上記一般式(IIIβ)で表される基であることが好ましい。
上記一般式(IIIα)で表される基中のX2は、酸素原子又は硫黄原子であることが好ましく、酸素原子であることが特に好ましい。オキシムエステル化合物が長波長の近紫外光を効率よく吸収するものとなり、光重合開始剤として高感度となるためである。上記一般式(IIIα)で表される基中のR41~R45は水素原子であることが好ましい。
上記一般式(IIIβ)で表される基中のX3は、酸素原子又は硫黄原子であることが好ましい。オキシムエステル化合物が長波長の近紫外光を効率よく吸収するものとなり、光重合開始剤として高感度となるためである。上記一般式(IIIβ)で表される基中のR46~R50は水素原子であることが好ましい。
上記一般式(Iβ)で表される本発明のオキシムエステル化合物においては、X101が不存在であることが好ましく、X101が硫黄であることも好ましい。
即ち、公知であり市販されているアルデヒド化合物と公知であり市販されているフッ化ベンゼン化合物とを炭酸カリウムを用いて反応させることでハロゲン化アリール化合物を得、ハロゲン化アリール化合物と公知であり市販されているN含有複素環化合物を反応させることで、N-アリール化合物を得る。
即ち、上記N-アリール化合物と酸クロリドと反応させることによりケトン化合物1を得、ケトン化合物1と塩酸ヒドロキシルアミンを反応させることにより、オキシム化合物1を得る。続いて、オキシム化合物1に、酸無水物又は酸クロリドを反応させることにより、上記一般式(Iα)又は(Iβ)で表される本発明のオキシムエステル化合物1を得る。
尚、オキシム化合物1及びオキシムエステル化合物1は、特許第4223071号公報に記載の方法でも製造できる。
即ち、上記N-アリール化合物と酸クロリドと反応させることによりケトン化合物2を得、ケトン化合物2と亜硝酸イソブチルを反応させることにより、オキシム化合物2を得る。続いて、オキシム化合物2に、酸無水物又は酸クロリドを反応させることにより、上記一般式(Iα)又は(Iβ)で表される本発明のオキシムエステル化合物2を得る。
本発明の光重合開始剤は、エチレン性不飽和化合物の光重合開始剤として有用なものである。
OXE 02(BASF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。
R63及びR64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、R65、OR66、SR67、NR68R69、COR70、SOR71、SO2R72又はCONR73R74を表し、
R63及びR64は、互いに結合して環を形成する場合があり、
R63及びR64は、それぞれ複数存在する場合、同一の場合も異なる場合があり、
R65、R66、R67、R68、R69、R70、R71、R72、R73及びR74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、
X4は、直接結合又はCOを表し、
X5は、酸素原子、硫黄原子、セレン原子、CR75R76、CO、又はPR77を表し、
R75、R76及びR77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水素原子は、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る場合があり、
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、-O-で置換される場合があり、
aは、0~4の整数を表し、
bは、0~5の整数を表す。)
本発明の感光性組成物は、本発明の光重合開始剤(A)及びエチレン性不飽和化合物(B)を含有し、任意成分として、着色剤(C)、アルカリ現像性化合物(D)、溶剤や、後述の任意の添加物を組み合わせて含有するものである。
これらの中でも、エポキシアクリレート樹脂、及び、下記一般式(V)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。
R81及びR82は、それぞれ複数存在する場合は、同一の場合も異なる場合があり、
cは、0~4の整数であり、
dは、0~4の整数であり、
mは0~10の整数であり、
mが0でない場合には光学異性体が存在するが、いかなる異性体でもよい。)
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。
尚、アルカリ現像性を有し且つエチレン性不飽和結合を有する化合物を用いる場合、該化合物は、前述の光重合開始剤(A)の含有量及び着色剤(C)の含有量を算出する際には、エチレン性不飽和化合物(B)に含めるものとする。
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(V)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剤等、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、感光性組成物において、レジストと光重合開始剤(A)の相溶性がよいので好ましい。
本発明の感光性組成物において、溶剤の含有量は、特に限定されるものではないが、感光性組成物全量100質量%中で30~95質量%が好ましく、より好ましくは50~95質量%である。溶剤の含有量が上記範囲の場合、ハンドリング性(感光性組成物の粘度や濡れ性)、乾燥時のムラの低減、及び液安定性(組成物に含まれる成分の析出や沈降を伴わない)に優れる感光性組成物となり、硬化物を得る際に硬化物の厚さを適切にコントロールできることから好ましい。
上記潜在性添加剤としては国際公開第2014/021023号パンフレットに記載されているものを好ましく使うことができる。
R81、R82、R83、R84及びR85は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有している場合がある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基若しくは炭素原子数2~20の複素環含有基、又は-O-R86を表し、R81、R82、R83、R84及びR85のうち少なくとも1つは水素原子でなく、
R86は、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表す。)
X7は、下記一般式(1)で表される基であり、
R92、R93、R94及びR95は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有している場合がある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、R92、R93、R94及びR95のうち少なくとも1つは水素原子でない。)
該脂肪族炭化水素基中のメチレン基は、-O-、-S-、-CO-、-COO-、-OCO-又は-NH-、或いは酸素原子が隣り合うことなしにこれらを組み合わせた結合基で置換される場合があり、
R97及びR98は、水素原子、炭素原子数1~8のアルキル基、炭素原子数6~20のアリール基又は炭素原子数7~20のアリールアルキル基を表し、
Z5及びZ6は、それぞれ独立に、直接結合、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-又は-NR100-を表し、
R99及びR100は、水素原子、置換基を有している場合がある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合がある炭素原子数6~35の芳香族炭化水素基又は置換基を有している場合がある炭素原子数2~35の複素環基を表し、
*は結合手を表す。)
R111、R112、R113及びR114は、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、又は置換基を有している場合がある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基若しくは炭素原子数2~20の複素環含有基を表し、R111、R112、R113及びR114のうち少なくとも1つは水素原子でなく、
環A1及びR86は、上記一般式(A)と同じである。)
Z11、Z12及びZ13は、それぞれ独立に、直接結合、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR121-、-PR121-、置換基を有している場合がある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合がある炭素原子数6~35の芳香族炭化水素基、又は置換基を有している場合がある炭素原子数2~35の複素環基を表し、
R121は、水素原子、置換基を有している場合がある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合がある炭素原子数6~35の芳香族炭化水素基又は置換基を有している場合がある炭素原子数2~35の複素環基を表し、該脂肪族炭化水素基中のメチレン基は、炭素-炭素二重結合、-O-、-CO-、-O-CO-、-CO-O-又は-SO2-で置換される場合がある。)
該脂肪族炭化水素基中のメチレン基は、-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-で置換される場合があり、
Z11~Z14は、それぞれ独立に、上記一般式(2)におけるZ11~Z13で表される基と同じ範囲の基である。)
該脂肪族炭化水素基は、-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-で中断されている場合があり、
Z11~Z15は、それぞれ独立に、上記一般式(2)におけるZ11~Z13で表される基と同じ範囲の基である。)
該脂肪族炭化水素基は、-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-で中断されている場合があり、
Z11~Z16は、それぞれ独立に、上記一般式(2)におけるZ11~Z13で表される基と同じ範囲の基である。)
有機重合体を使用する場合、その使用量は、エチレン性不飽和化合物(B)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、互いに同一である場合があり、異なる場合がある。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る場合があり、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る場合がある。
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。
本発明の感光性組成物又はアルカリ現像性感光性樹脂組成物は、硬化させるに先立って、スピンコーター、ロールコーター、バーコーター、ダイコーター、カーテンコーター、各種の印刷、浸漬等の公知の手段で、ソーダガラス、石英ガラス、半導体基板、金属、紙、プラスチック等の支持基体上に適用することができる。また、一旦フィルム等の支持基体上に施した後、他の支持基体上に転写することもでき、その適用方法に制限はない。
100mlの4つ口フラスコに、2-クロロ-4’-フルオロアセトフェノン(3.59g)、サリチル酸アルデヒド(5.08g)、炭酸カリウム(5.75g)、アセトン(15g)をそれぞれ秤量した後、加熱還流を1時間行った。室温まで冷却後、イオン交換水(41.6g)を添加し、析出物をろ取し、十分に乾燥させ、淡黄色固体として中間体1Aを(4.74g:収率95%)得た。
100mlの4つ口フラスコに、中間体1A(4.42g)、下記インドール化合物1A(4.07g)、炭酸カリウム(4.62g)及びDMAc(23.25g)をそれぞれ秤量した後、110℃で3時間反応させた。イオン交換水(15.5g)及び酢酸エチル(23.25g)を加え、油水分離し、有機層を3回水洗し脱溶媒を行った。その後、得られた残渣に酢酸エチル(15.5g)及びヘキサン(23.25g)を加え、加熱溶解後、冷却し再結晶を行った。5℃まで冷却後、析出物をろ取し、十分に乾燥させ、白色固体として中間体1Bを(6.8g:収率87%)得た。
30mlの2つ口フラスコに中間体1B(3.74g)及びDMF(12.93g)を秤量し、5℃で撹拌しながら35%塩酸1.26g及び亜硝酸イソブチル0.87gを滴下し、室温で30時間撹拌した。イオン交換水(11.9g)及び酢酸エチル(11.9g)を加え、油水分離し、有機層を3回水洗した。有機層を脱溶媒後、シリカゲルカラム(酢酸エチル/ヘキサン=1/9)により精製を行い淡黄色固体として中間体1C(3.0g:収率75%)を得た。
30mlの2口ナスフラスコに中間体1C(2.21g)及びTHF(7.2g)をそれぞれ秤量し、窒素気流、氷冷下において塩化アセチル(2.12g)、トリエチルアミン(2.72g)を滴下し、室温で1時間撹拌を行った。イオン交換水(7.2g)及び酢酸エチル(7.2g)を加え、油水分離し、有機層を3回水洗した。有機層を脱溶媒後、シリカゲルカラム(酢酸エチル/ヘキサン)により精製を行い、淡黄色固体として化合物No.1(1.5g:収率63%)を得た。
得られた化合物No.1の分析結果を[表1]~[表3]に示す。尚、[表1]に併記したOXE 02は、後述の比較例1で用いた市販の光重合開始剤である。
(工程1)中間体2Aの製造
上記中間体1Bを9.6g、ジメチルホルムアセトアミドを30.0g、ヒドロキシアミン塩酸塩を2.2g仕込んだ後、60℃で水酸化ナトリウムを1.2g仕込んだ。60℃で2時間反応させた後、イオン交換水、クロロホルムを仕込み、加温しながら抽出した。有機層を3回水洗し、脱溶媒後、シリカゲルカラム(酢酸エチル/ヘキサン=1/6)により精製を行い、下記中間体2A(2.0g:収率25%)を得た。
中間体1Cを上記中間体2Aに変更した以外は実施例1の工程4と同様にして、化合物No.189を得た。
(工程1)中間体3Bの製造
インドール化合物1Aを下記カルバゾール化合物3Aに変更した以外は実施例1の工程2と同様にして、下記中間体3Bを得た。
100mlの4つ口フラスコに塩化アルミニウムを2.72g、ジクロロエタンを30.0g仕込み、氷冷下、中間体3Bを7.54g添加し、次いでオクタノイルクロリドを3.32g添加した。室温で1時間反応させた後、反応液を氷水にあけ油水分離を行った。有機層を3回水洗後、脱溶媒を行い、シリカゲルカラム(酢酸エチル/ヘキサン=1/10)により下記中間体3C(1.1g:収率11%)を得た。
中間体1Cを上記中間体3Cに変更した以外は実施例1の工程4と同様にして、上記化合物No.190を得た。
実施例1の工程2で使用した中間体1Aを下記中間体4Aに変更した以外は実施例1と同様にして、上記化合物No.191を得た。
実施例1の工程2で使用した中間体1Aを下記中間体5Aに変更した以外は実施例1と同様にして、上記化合物No.192を得た。
(工程1)中間体6Bの製造
インドール化合物1Aを下記フェノチアジン化合物6Aに変更した以外は実施例1の工程2と同様にして、下記中間体6Bを得た。
中間体3Bを上記中間体6Bに変更し、用いた試薬の等量が2倍量になるように調製した以外は実施例3の工程2同様にして、下記中間体6Cを得た。
中間体1Bを上記中間体6Cに変更し、用いた試薬の等量が2倍量になるように調製した以外は実施例1の工程3と同様にして、下記中間体6Dを得た。
中間体1Cを上記中間体6Dに変更し、用いた試薬の等量が2倍量になるように調製した以外は実施例1の工程4と同様にして、上記化合物No.193を得た。
(工程1)中間体7Aの製造
中間体1Bを上記中間体6Cに変更した以外は実施例1の工程3と同様にして、下記中間体7Aを得た。
中間体1Cを上記中間体7Aに変更した以外は実施例1の工程4と同様にして、上記化合物No.194を得た。
分散剤としてDISPERBYK-161(12.5質量部;ビックケミージャパン製)及び着色剤としてピグメントブルー15:6(15質量部)を、PGMEA(72.5質量部)にビーズミルを使用して分散させて、ブルー顔料分散液No.1を製造した。
下記[表4]の配合に従って各成分を混合し、感光性組成物No.1~No.7(実施例8~14)及び比較用の感光性組成物No.8(比較例1)を得た。尚、表中の数字は質量部を表す。実施例8~14及び比較例1においては、光重合開始剤をそれぞれ単独で使用した。
また、表中の符号は、下記の成分を表す。
A-1: 化合物No.1(実施例1で得られた本発明の光重合開始剤)
A-2: 化合物No.189(実施例2で得られた本発明の光重合開始剤)
A-3: 化合物No.190(実施例3で得られた本発明の光重合開始剤)
A-4: 化合物No.191(実施例4で得られた本発明の光重合開始剤)
A-5: 化合物No.192(実施例5で得られた本発明の光重合開始剤)
A-6: 化合物No.193(実施例6で得られた本発明の光重合開始剤)
A-7: 化合物No.194(実施例7で得られた本発明の光重合開始剤)
A-8: OXE 02(本発明に属さない光重合開始剤;BASF社製)
B-1: SPC-3000(酸基を有するエチレン性不飽和化合物;昭和電工製;固形分42.2質量%のPGMEA溶液)
B-2: カヤラッドDPHA(エチレン性不飽和化合物;日本化薬製;固形分100質量%)
C-1: ブルー顔料分散液No.1(製造例1で得られた分散液)
X-1: KBE-403(シランカップリング剤;信越化学製)
X-2: F-554(フッ素系レベリング剤、含フッ素基・親油性基含有オリゴマー;DIC製)
Y-1: PGMEA(溶剤)
尚、SPC-3000(B-1)は、エチレン性不飽和結合を有し且つアルカリ現像性を有する化合物であり、カヤラッドDPHA(B-2)は、エチレン性不飽和結合を有する化合物であるがアルカリ現像性は有しない。
感光性組成物No.1~No.7及び比較用の感光性組成物No.8の感度並びにそれらから得られる硬化物の輝度の評価を下記の手順で行った。評価結果を[表4]に併記する。
ガラス基板上に感光性組成物No.1~No.7(実施例8~14)及び比較用の感光性組成物No.8(比較例1)をスピンコート(500rpmにて2秒間、次いで900rpmにて5秒間)し、ホットプレートを用いて、90℃で90秒間プリベークを行った後、23℃で40秒間冷却した。その後、高圧水銀ランプを用いてマスク(マスク開口30μm)を介して露光した(露光量40mJ/cm2)。現像液として2.5質量%炭酸ナトリウム水溶液を用いて現像した後、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。得られたパターンを電子顕微鏡で観察し、マスク開口に対応する部分の線幅を測定した。線幅が30μm以上のものをA、30μm未満のものをBとした。線幅が大きいほど感度が良好であることを意味する。
ガラス基板上に感光性組成物No.1~No.7(実施例8~14)及び比較用の感光性組成物No.8(比較例1)をスピンコート(500rpmにて2秒間、次いで900rpmにて5秒間)し、ホットプレートを用いて、90℃で90秒間プリベークを行った後、23℃で40秒間冷却した。その後、高圧水銀ランプを用いて100mJ/cm2で露光し、評価サンプルを作成した。得られたサンプルの380~780nmにおける透過率から、JIS Z8701に準拠してY値を求めた。Y値が高いほど輝度が高く可視光領域において高い透過率を有することを意味し、有用である。
Claims (11)
- 下記一般式(Iα)又は(Iβ)で表されるオキシムエステル化合物。
(式中、R1、R2、R3、R4、R5及びR6は、それぞれ独立に、下記一般式(II)で表される基、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R21、OR21、SR21、NR22R23、COR21、SOR21、SO2R21又はCONR22R23を表し、
R1、R2、R3、R4、R5及びR6のうち、少なくとも一つが下記一般式(II)で表される基であり、
R7、R8、R10及びR11は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R21、OR21、SR21、NR22R23、COR21、SOR21、SO2R21又はCONR22R23を表し、
R9は、下記一般式(IIIα)で表される基又は下記一般式(IIIβ)で表される基であり、
R21、R22及びR23は、それぞれ独立に、炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環を表し、
R21、R22及びR23で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環で置換される場合があり、炭素原子数2~20の炭化水素基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR24-、-NR24CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、R24は、水素原子又は炭素原子数1~20の炭化水素基を表し、
X1は、直接結合、-CO-、-O-又は-S-を表す。)
(式中、R31及びR32は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環を表し、
R31及びR32で表される炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環で置換される場合があり、R31及びR32で表される炭素原子数2~20の炭化水素基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR33-、-NR33CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、R33は、水素原子又は炭素原子数1~20の炭化水素基を表し、
nは0又は1を表し、*は結合手を表す。)
(式中、R41、R42、R43、R44、R45、R46、R47、R48、R49及びR50は、水素原子を表し、
X2及びX3は、-O-、-S-又は-NR54-を表し、
R54は、水素原子又は炭素原子数1~20の炭化水素基を表し、
*は結合手を表す。)
(式中、R101、R102、R103、R104、R105、R106、R107及びR108は、それぞれ独立に、上記一般式(II)で表される基、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R121、OR121、SR121、NR122R123、COR121、SOR121、SO2R121又はCONR122R123を表し、
R101、R102、R103、R104、R105、R106、R107及びR108のうち、少なくとも一つが上記一般式(II)で表される基であり、
R109、R110、R112及びR113は、それぞれ独立に、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R121、OR121、SR121、NR122R123、COR121、SOR121、SO2R121又はCONR122R123を表し、
R111は、上記一般式(IIIα)で表される基又は上記一般式(IIIβ)で表される基であり、
R121、R122及びR123は、それぞれ独立に、炭素原子数1~20の炭化水素基又は炭素原子数2~20の複素環を表し、
R121、R122及びR123で表される基中の水素原子は、ハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環で置換される場合があり、炭素原子数2~20の炭化水素基中のメチレン基は、-O-、-CO-、-COO-、-OCO-、-NR124-、-NR124CO-、-S-、-CS-、-SO2-、-SCO-、-COS-、-OCS-又はCSO-で置換される場合があり、
R124は、水素原子又は炭素原子数1~20の炭化水素基を表し、
X101は、直接結合、-CO-、-O-又は-S-を表す。) - 一般式(Iα)中のR3及びR5のうち少なくとも一つが、一般式(II)で表される基である請求項1に記載のオキシムエステル化合物。
- 一般式(Iβ)中のR103及びR106のうち少なくとも一つが、一般式(II)で表される基である請求項1に記載のオキシムエステル化合物。
- 一般式(IIIα)中のX2及び一般式(IIIβ)X3が、-O-又は-S-である請求項1~3の何れか一項に記載のオキシムエステル化合物。
- 請求項1~4の何れか一項に記載のオキシムエステル化合物を含有する光重合開始剤。
- 請求項5に記載の光重合開始剤(A)及びエチレン性不飽和化合物(B)を含有する感光性組成物。
- 更に着色剤(C)を含有する請求項6に記載の感光性組成物。
- 請求項6又は7に記載の感光性組成物にアルカリ現像性化合物(D)を含有させてなるアルカリ現像性感光性樹脂組成物。
- 請求項6若しくは7に記載の感光性組成物又は請求項8に記載のアルカリ現像性感光性樹脂組成物の硬化物。
- 請求項9に記載の硬化物を含有するディスプレイ表示装置。
- 請求項6若しくは7に記載の感光性組成物又は請求項8に記載のアルカリ現像性感光性樹脂組成物を用い、該組成物を硬化させる工程を有する、硬化物の製造方法。
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