JP4609587B2 - 隔壁形成用ネガ型感光性樹脂組成物 - Google Patents
隔壁形成用ネガ型感光性樹脂組成物 Download PDFInfo
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- JP4609587B2 JP4609587B2 JP2009231074A JP2009231074A JP4609587B2 JP 4609587 B2 JP4609587 B2 JP 4609587B2 JP 2009231074 A JP2009231074 A JP 2009231074A JP 2009231074 A JP2009231074 A JP 2009231074A JP 4609587 B2 JP4609587 B2 JP 4609587B2
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- Prior art keywords
- photosensitive resin
- resin composition
- repellent agent
- partition
- mass
- Prior art date
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- 230000015572 biosynthetic process Effects 0.000 title claims description 51
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- 239000003795 chemical substances by application Substances 0.000 claims description 80
- 239000005871 repellent Substances 0.000 claims description 77
- 230000002940 repellent Effects 0.000 claims description 75
- 229920005989 resin Polymers 0.000 claims description 69
- 239000011347 resin Substances 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 67
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- 230000002378 acidificating effect Effects 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 24
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
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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 claims description 3
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 claims description 2
- LEEAJAXCIHSVRB-UHFFFAOYSA-N [1,1,2,2-tetrafluoro-2-[1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl(propyl)amino]ethyl] prop-2-enoate Chemical compound C(C=C)(=O)OC(C(N(S(=O)(=O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)CCC)(F)F)(F)F LEEAJAXCIHSVRB-UHFFFAOYSA-N 0.000 claims 1
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- 239000003505 polymerization initiator Substances 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
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- 239000005056 polyisocyanate Chemical class 0.000 description 4
- 229920001228 polyisocyanate Chemical class 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
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- 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
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-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
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000003672 ureas Chemical group 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/492—Photosoluble emulsions
-
- 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
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
- Electroluminescent Light Sources (AREA)
- Optical Filters (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
また、撥インク剤(B)がエチレン性二重結合を有しており、光照射で硬化するので、この硬化によって、撥インク性の持続性が高くなる。
さらに、プリベークの際に撥インク剤(B)が塗膜表面近傍に移行することによって、基材付近の撥インク剤(B)の濃度が相対的に減少するので、本フルオロアルキル基による基材密着性の低下を防止できる。
また、撥インク剤(B)におけるフッ素含有量および撥インク剤(B)のネガ型感光性樹脂組成物の全固形分における割合が上記範囲であることにより、撥インク性、基材密着性に優れる。
アルカリ可溶の感光性樹脂(A)は、分子内に3個以上のエチレン性二重結合を有するため、露光部分と未露光部分とのアルカリ溶解度に差がつきやすく、現像性に優れ、より少ない露光量での微細なパターン形成が可能となる。
また、本発明は、酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)と、カーボンブラック、チタンブラック、黒色金属酸化物顔料、および有機顔料からなる群から選択される少なくとも1種の着色剤(H)とを含有し、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%であることを特徴とする隔壁形成用ネガ型感光性樹脂組成物を提供する。
また、本発明は、酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなり、数平均分子量が500以上15000未満である撥インク剤(B)と、光重合開始剤(C)とを含有し、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%であることを特徴とする隔壁形成用ネガ型感光性樹脂組成物を提供する。
酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有し、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%であることを特徴とする隔壁形成用ネガ型感光性樹脂組成物を提供する。
酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有し、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%であることを特徴とする隔壁形成用ネガ型感光性樹脂組成物を提供する。
酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有し、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%であることを特徴とする隔壁形成用ネガ型感光性樹脂組成物を提供する。
アゾ化合物としては、2,2´−アゾビスイソブチロニトリル、1,1−アゾビス(シクロヘキサン−1−カルボニトリル)、2,2´−アゾビス(2,4−ジメチルバレロニトリル)、2,2´−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)、2,2´−アゾビスイソ酪酸ジメチル、2,2´−アゾビス(2−アミジノプロパン)二塩酸塩等が挙げられる。
CF(CF3)O(CF2)5CF3、
CF2O(CF2CF2O)pCF3(pは1〜8)、
CF(CF3)O(CF2CF(CF3)O)qC6F13(qは1〜4)、
CF(CF3)O(CF2CF(CF3)O)rC3F7(rは1〜5)
R5、R6の具体例としては、CH2、CH2CH2、CH(CH3)、CH2CH2CH2、C(CH3)2、CH(CH2CH3)、CH2CH2CH2CH2、CH(CH2CH2CH3)、CH2(CH2)3CH2、CH(CH2CH(CH3)2)等が挙げられる。なお、本発明においてはR5は単結合であってもよい。
また、上記の重合性単量体は単独で用いてもよく、2種以上を併用してもよい。
水酸基を有する単量体、酸無水物、エチレン性二重結合を有する酸無水物、水酸基を有する化合物としては、前記ラジカル重合体(A1)の説明で記述した具体例が挙げられる。
なお、上記の単量体は単独で用いてもよく、2種以上を併用してもよい。特に(メタ)アクリル酸エステル類、(メタ)アクリルアミド類が好ましい。(メタ)アクリル酸エステル類、(メタ)アクリルアミド類としては、前記ラジカル重合体(A1)の説明で記述した具体例が挙げられる。
特に、上記アミノ安息香酸類、上記ベンゾフェノン類等は、その他の光ラジカル発生剤と共に用いられて、増感効果を発現することがある。また、トリエタノールアミン、メチルジエタノールアミン、トリイソプロパノールアミン、n−ブチルアミン、N−メチルジエタノールアミン、ジエチルアミノエチルメタクリレート等の脂肪族アミン類も同じく光ラジカル発生剤と共に用いられて、増感効果を発現することがある。
具体例としては、ジエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,9−ノナンジオールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート等が挙げられる。これらは単独で用いてもよく、2種以上を併用してもよい。
シランカップリング剤の具体例としては、テトラエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、メチルトリメトキシシラン、ビニルトリメトキシシラン、3−メタクリロイルオキシプロピルトリメトキシシラン、3−クロロプロピルトリメトキシシラン、3−メルカプトプロピルトリメトキシシラン、ヘプタデカフルオロオクチルエチルトリメトキシシラン、POA鎖含有トリエトキシシラン等が挙げられる。これらは単独で用いてもよく、2種以上を併用してもよい。
希釈剤(F)の具体例としては、ラジカル重合体(A1)の説明で例示した重合性単量体が挙げられる。また、ラジカル重合体(A1)を合成するときに使用する溶剤の説明で例示した溶剤が挙げられる。その他には、n−ブタン、n−ヘキサン等の鎖式炭化水素、シクロヘキサン等の環式飽和炭化水素、トルエン、キシレン、ベンジルアルコール等の芳香族炭化水素等が挙げられる。これらは単独で用いてもよいし、2種以上を併用してもよい。
照射装置として、公知の超高圧水銀灯等を用いることができる。通常は、5〜1000mJ/cm2の露光量の範囲で露光される。
この優れた撥インク性、その持続性、基材密着性および現像性を発現する機構は、必ずしも明確ではないが、以下のように考えられる。
さらに、プリベークの際に撥インク剤(B)が塗膜表面近傍に移行することによって、基材付近の撥インク剤(B)の濃度が相対的に減少し、本フルオロアルキル基による基材密着性の低下を防止することができる。
また、感光性樹脂(A)は主に現像性を付与し、分子内に3個以上のエチレン性二重結合を有するため、露光部分と未露光部分とのアルカリ溶解度に差がつきやすく、より少ない露光量での微細なパターン形成を可能にする。
C6FMA:CH2=C(CH3)COOCH2CH2(CF2)6F
C4FMA:CH2=C(CH3)COOCH2CH2(CF2)4F
C8FA:CH2=CHCOOCH2CH2(CF2)8F
MAA:メタクリル酸
AA:アクリル酸
HEMA:2−ヒドロキシエチルメタクリレート
N−MAA:N−ヒドロキシメチルアクリルアミド
MMA:メチルメタクリレート
CHMA:シクロヘキシルメタクリレート
IBMA:イソボルニルメタクリレート
GMA:グリシジルメタクリレート
TFEMA:トリフルオロエチルメタクリレート
DSH:n−ドデシルメルカプタン
V−70:2,2´−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)
(和光純薬社製、商品名 V−70)
MOI:2−メタクリロイルオキシエチルイソシアネート
AC:アクリロイルクロライド
ECA:3,4−エポキシシクロヘキシルメチルアクリレート
DBTDL:ジブチル錫ジラウレート
BHT:2,6−ジ−t−ブチル−p−クレゾール
TEA:トリエチルアミン
EEA:2−(2−エトキシエトキシ)エチルアセテート
MIBK:メチルイソブチルケトン
IR907:光重合開始剤(チバ−ガイギー社製、商品名 IRGACURE−907)
D310:ジペンタエリスリトールペンタアクリレート(日本化薬社製、商品名 KAYARAD D−310)
DEAB:4,4´−ビス(ジエチルアミノ)ベンゾフェノン
KBM403:3−グリシドキシプロピルトリメトキシシラン(信越化学社製、商品名 KBM−403)
DEGDM:ジエチレングリコールジメチルエーテル
M325:メチルエーテル化メラミン樹脂(三井サイテック社製、商品名 マイコート#325)
CCR−1115:クレゾールノボラック樹脂(日本化薬社製、商品名 CCR−1115、エチレン性二重結合数≒6)
EOCN−104S:クレゾールノボラック型エポキシ樹脂(日本化薬社製、商品名 EOCN−104S)
F172:パーフルオロアルキル基および親油性基含有オリゴマー(大日本インキ化学工業社製、商品名 メガファックF172)
P−1M:CH2=C(CH3)COOCH2CH2OPO(OH)2(共栄社化学社製、商品名 ライトエステルP−1M)
P−2M:(CH2=C(CH3)COOCH2CH2O)2POOH(共栄社化学社製、商品名 ライトエステルP−2M)
PETMA:ペンタエリスリトールテトラメタクリレート
HPPMA:2−ヒドロキシ−3−フェニルオキシプロピルメタクリレート
NVP:N−ビニルピロリドン
CB:カーボンブラック(ブラック顔料20%プロピレングリコールモノメチルエーテルアセテート溶液)
[合成例1]
撹拌機を備えた内容積1Lのオートクレーブに、アセトンの555.0g、AAの96.0g、HEMAの96.0g、IBMAの48.0g、連鎖移動剤DSHの9.7gおよび重合開始剤V−70の7.1gを仕込み、窒素雰囲気下に撹拌しながら、40℃で18時間重合させ、重合体1の溶液を得た。該重合体1の数平均分子量は5000であった。
得られた重合体1のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、重合体1の240gを得た。
温度計、撹拌機、加熱装置を備えた内容量300mLのガラス製フラスコに、重合体1の100g、MOIの48.3g、DBTDLの0.19g、BHTの2.4gおよびアセトンの100gを仕込み、撹拌しながら、30℃で18時間重合させ、樹脂A−1の溶液を得た。該樹脂A−1の数平均分子量は6900であった。
得られた樹脂A−1のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、樹脂A−1の148gを得た。1分子中に含まれるエチレン性二重結合は、12.3個である。
重合体1の合成において、原料の配合量を表1のように変更したほかは同様にして、重合体2〜9および11を得た。
得られた重合体2のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、重合体2の240gを得た。
温度計、撹拌機、加熱装置を備えた内容量300mLのガラス製フラスコに、重合体2の100g、ACの41.8g、TEAの46.7gおよびアセトンの100gを仕込み、撹拌しながら、30℃で18時間重合させ、樹脂A−2の溶液を得た。該樹脂A−2の数平均分子量は6860であった。
得られた樹脂A−2のアセトン溶液に水を加え再沈精製し、塩酸1%水溶液にて洗浄し、次いで石油エーテルにて再沈精製し、真空乾燥し、樹脂A−2の140gを得た。
[合成例3]
樹脂A−1の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−1を得た。
樹脂A−2の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−2を得た。
樹脂A−1の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−3を得た。
温度計、撹拌機、加熱装置を備えた内容量300mLのガラス製フラスコに、重合体5の100g、ECAの42.4g、MIBKの100gを仕込み、撹拌しながら、50℃で48時間重合させ、樹脂B−4の溶液を得た。該樹脂B−4の数平均分子量は10000であった。
得られた樹脂B−4のアセトン溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、樹脂B−4の140gを得た。
樹脂A−1の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−5を得た。
樹脂A−1の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−6を得た。
樹脂A−2の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−7を得た。
樹脂A−1の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−8を得た。
撹拌機を備えた内容積0.3Lのオートクレーブに、EEAの100.0g、GMAの40.0g、TFEMAの60.0gおよび重合開始剤ベンゾイルパーオキサイドの3.0gを仕込み、窒素雰囲気下に撹拌しながら、75℃で5時間重合させ、重合体10の50%溶液を得た。
次いで、温度計、撹拌機、加熱装置を備えた内容量500mLのガラス製フラスコに、該重合体10の50%溶液の300g、AAの26.9g、メチルヒドロキノンの0.16gおよびトリフェニルホスフィンの0.9gを仕込み、95℃で32時間重合させ、さらに無水コハク酸の49.8g、EEAの79.4gを追加で仕込み、90℃で10時間重合させ、樹脂B−9の溶液を得た。樹脂B−9の数平均分子量は20000であった。
得られた樹脂B−9のEEA溶液に水を加え再沈精製し、次いで石油エーテルにて再沈精製し、真空乾燥し、樹脂B−9の220gを得た。該樹脂B−9の含フッ素割合は11.5%である。
樹脂A−1の合成において、原料の配合量を表2のように変更したほかは同様にして、樹脂B−10を得た。
表3、4に示す割合で、樹脂A−1、A−2、樹脂B−1〜B−10、光重合開始剤(C)、ラジカル架橋剤(D)、シランカップリング剤(E)、希釈剤(F)、熱硬化剤(G)および必要に応じその他成分を配合して例1〜17のネガ型感光性樹脂組成物を得た。
次に、ガラス基板上にスピンナーを用いて、ネガ型感光性樹脂組成物を塗布した後、100℃で2分間ホットプレート上でプリベークし、膜厚3.0μmの塗膜を形成した。
その後、塗膜にマスク(ライン/スペース=20μm/20μm)を接触させ、超高圧水銀灯により150mJ/cm2照射し、次いで未露光部分を0.1重量%テトラメチルアンモニウムヒドロキシド水溶液に40秒間浸漬し現像し、未露光部を水により洗い流し、乾燥させた。次いで、ホットプレート上、220℃で1時間加熱することにより、パターンが形成されたガラス基板を得た。
パターンが形成されたガラス基板について、以下の方法で、撥インク性、撥インク持続性、現像性の評価を行なった。その結果を表3、4にまとめて示す。
撥インク持続性:パターンが形成されたガラス基板を5mm/secの一定速度で試料台上を搬送させながら、高圧噴射装置として超高圧ジェット精密洗浄システムAF5400S(旭サナック(株)製)を使用して扇状に拡がる薄層の水噴射を試料に施した。超高圧マイクロジェットは、扇状の噴射面が、試料の進行方向に直角であり、かつ試料面に垂直な方向に噴射した。また、そのときの超高圧マイクロジェットの印加圧力は、150kgf/cm2(14.7MPa)とした。水洗後のガラス基板の形成されたパターンの樹脂部分の水およびキシレンの接触角を測定した。
現像性:現像できたものを○、ライン/スペースのパターンは形成できたが、ライン/スペースのライン部分の一部が断絶したり、曲がったり、折れ曲がったりしたものについては△、ライン/スペースのパターンが形成できなかったものについては×とした。
基材密着性:JIS K 5400記載の碁盤目テープ法により評価した。塗板をカッターにて、2mm間隔でます目の数が25個となるように、碁盤目状に傷を付けた。次に粘着テープを貼り、剥がした後の塗膜の付着状態を目視により、ます目が殆ど剥がれたものを×、ます目が剥がれなかったものを○として評価した。
Claims (10)
- 酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有することを特徴とする隔壁形成用ネガ型感光性樹脂組成物(ただし、N−プロピルパーフルオロオクチルスルホニルアミノエチルアクリレートを重合単位として含有する共重合体と、ジペンタエリスリトールヘキサアクリレートと、2−(4−メトキシナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジンと、リンゴ酸と、ビクトリアブルーと、メチルグリコールとを少なくとも含有する感光性樹脂組成物を除く)。ただし、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%である。
- 前記感光性樹脂(A)100質量部に対し、前記撥インク剤(B)を0.1〜200質量部、前記光重合開始剤(C)を0.1〜50質量部含有する請求項1記載の隔壁形成用ネガ型感光性樹脂組成物。
- 前記撥インク剤(B)が、酸性基を有する請求項1または2に記載の隔壁形成用ネガ型感光性樹脂組成物。
- 前記感光性樹脂(A)100質量部に対し、2個以上のエチレン性二重結合を有するアルカリ不溶の化合物からなるラジカル架橋剤(D)を10〜500質量部を含有する請求項1〜3のいずれか1つに記載の隔壁形成用ネガ型感光性樹脂組成物。
- 得られる隔壁の水の接触角が90度以上である請求項1〜4のいずれか1つに記載の隔壁形成用ネガ型感光性樹脂組成物。
- 酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)と、カーボンブラック、チタンブラック、黒色金属酸化物顔料、および有機顔料からなる群から選択される少なくとも1種の着色剤(H)と、を含有することを特徴とする隔壁形成用ネガ型感光性樹脂組成物。ただし、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%である。
- 酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなり、数平均分子量が500以上15000未満である撥インク剤(B)と、光重合開始剤(C)とを含有することを特徴とする隔壁形成用ネガ型感光性樹脂組成物。ただし、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%である。
- キシレンの接触角が30度以上である隔壁の製造に用いられる隔壁形成用ネガ型感光性樹脂組成物であって、
酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有することを特徴とする隔壁形成用ネガ型感光性樹脂組成物。ただし、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%である。 - 液晶用カラーフィルタ用隔壁材として用いられる隔壁形成用ネガ型感光性樹脂組成物であって、
酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有することを特徴とする隔壁形成用ネガ型感光性樹脂組成物。ただし、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%である。 - 有機ELディスプレイ用隔壁材として用いられる隔壁形成用ネガ型感光性樹脂組成物であって、
酸性基および分子内に3個以上のエチレン性二重結合を有するアルカリ可溶の感光性樹脂(A)と、水素原子の少なくとも1つがフッ素原子に置換された炭素数20以下のアルキル基(ただし、前記アルキル基はエーテル性の酸素を有するものを含む。)を有する重合単位(b1)、およびエチレン性二重結合を有する重合単位(b2)を有する重合体からなる撥インク剤(B)と、光重合開始剤(C)とを含有することを特徴とする隔壁形成用ネガ型感光性樹脂組成物。ただし、撥インク剤(B)におけるフッ素含有量は、5〜25質量%であり、撥インク剤(B)の隔壁形成用ネガ型感光性樹脂組成物の全固形分における割合は、0.01〜20質量%である。
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DE60318884T2 (de) | 2009-01-22 |
US20070003880A1 (en) | 2007-01-04 |
JP2009048200A (ja) | 2009-03-05 |
JP4488098B2 (ja) | 2010-06-23 |
JP4609071B2 (ja) | 2011-01-12 |
WO2004042474A1 (ja) | 2004-05-21 |
CN1711503B (zh) | 2010-05-26 |
EP1560068A1 (en) | 2005-08-03 |
KR20050074546A (ko) | 2005-07-18 |
US7494764B2 (en) | 2009-02-24 |
TW200419310A (en) | 2004-10-01 |
EP1560068A4 (en) | 2007-05-02 |
KR101026094B1 (ko) | 2011-04-04 |
US20050191580A1 (en) | 2005-09-01 |
TWI342982B (ja) | 2011-06-01 |
DE60318884D1 (de) | 2008-03-13 |
US7267929B2 (en) | 2007-09-11 |
JPWO2004042474A1 (ja) | 2006-03-09 |
JP2010217910A (ja) | 2010-09-30 |
JP2010002928A (ja) | 2010-01-07 |
EP1560068B1 (en) | 2008-01-23 |
AU2003280695A1 (en) | 2004-06-07 |
CN1711503A (zh) | 2005-12-21 |
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