TWI778082B - 聚合性組合物、黑色矩陣用感光性組合物及黑柱間隔物用感光性組合物 - Google Patents
聚合性組合物、黑色矩陣用感光性組合物及黑柱間隔物用感光性組合物 Download PDFInfo
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- TWI778082B TWI778082B TW107120727A TW107120727A TWI778082B TW I778082 B TWI778082 B TW I778082B TW 107120727 A TW107120727 A TW 107120727A TW 107120727 A TW107120727 A TW 107120727A TW I778082 B TWI778082 B TW I778082B
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- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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- AKLJIUURIIIOLU-UHFFFAOYSA-N silane 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound [SiH4].CO[Si](OC)(OC)CCCOC(=O)C(C)=C AKLJIUURIIIOLU-UHFFFAOYSA-N 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
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- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
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- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
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- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
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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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/871—Self-supporting sealing arrangements
- H10K59/8723—Vertical spacers, e.g. arranged between the sealing arrangement and the OLED
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- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
-
- 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
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- G—PHYSICS
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- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/136—Liquid crystal cells structurally associated with a semi-conducting layer or substrate, e.g. cells forming part of an integrated circuit
- G02F1/1362—Active matrix addressed cells
- G02F1/136209—Light shielding layers, e.g. black matrix, incorporated in the active matrix substrate, e.g. structurally associated with the switching element
-
- 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
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Abstract
本發明之聚合性組合物係含有聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及除該鹼性顯影性化合物(C)以外之乙烯性不飽和化合物(D)者,上述聚合起始劑(A)含有具有羥基之α-胺基苯乙酮化合物(A1)。較佳為上述聚合起始劑(A)除了具有羥基之α-胺基苯乙酮化合物(A1)以外亦含有具有下述通式(I)所表示之基之肟酯化合物(A2)。
Description
本發明係關於含有具有羥基之α-胺基苯乙酮化合物作為聚合起始劑,進而含有著色劑、鹼性顯影性化合物及除鹼性顯影性化合物以外之乙烯性不飽和化合物的聚合性組合物。又,本發明係關於含有該組合物之黑色矩陣(以下亦記載為「BM」)用感光性組合物及黑柱間隔物(以下亦記載為「BCS」)用感光性組合物以及由該等組合物獲得之硬化物。
於液晶顯示裝置、有機EL顯示裝置等顯示器顯示裝置中,為了保持單元之上部與下部之基板間之距離而使用間隔物。
間隔物係藉由如下方式而形成者:將聚合性組合物塗佈於基板上,介隔特定之遮罩進行曝光後進行顯影。近年來,使用將柱間隔物及黑色矩陣整合於1個模組中而具有遮光性之BCS。
於專利文獻1中記載了含有α-胺基苯烷酮化合物之感光性阻焊劑用光聚合起始劑。於專利文獻2中記載了BCS形成用感光性樹脂組合物,其含有實施了導入酸性基之處理的碳黑,可形成相對介電常數較低之BCS。於專利文獻3中記載了著色感光性樹脂組合物,其含有共聚物、環氧樹脂化合物或由其而衍生之化合物、以及包含黑色著色劑及藍色著色劑之著色劑,可形成顯示良好之彈性回覆率之BCS。 [先前技術文獻] [專利文獻]
[專利文獻1]日本專利特開2016-090857號公報 [專利文獻2]日本專利特開2015-093986號公報 [專利文獻3]日本專利特開2014-146029號公報
本發明所欲解決之課題係目前尚不存在彈性回覆、遮光性、耐化學品性優異,介電常數低,電特性良好之硬化物(尤其是BCS)。
因此,本發明之目的在於提供可獲得彈性回覆、遮光性、耐化學品性優異,介電常數低,電特性良好之硬化物的聚合性組合物、BM用感光性組合物及BCS用感光性組合物。又,本發明之目的在於提供由該聚合性組合物、該BM用感光性組合物及該BCS用感光性組合物獲得之硬化物,含有該硬化物之顯示器顯示裝置,及製造該硬化物之方法。
本發明進行銳意研究之結果,藉由提供下述[1]~[9]而達成上述目的。
[1] 一種聚合性組合物,其係含有聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及除該鹼性顯影性化合物(C)以外之乙烯性不飽和化合物(D)之聚合性組合物, 上述聚合起始劑(A)含有具有羥基之α-胺基苯乙酮化合物(A1)。
[2] 如[1]之聚合性組合物,其係上述聚合起始劑(A)進而含有具有下述通式(I)所表示之基之肟酯化合物(A2)的聚合性組合物;
[化1](式中,R1
及R2
分別獨立地表示氫原子、鹵素原子、硝基、氰基、碳原子數為1~20之烴基或含有雜環之碳原子數為2~20之基, 存在R1
及R2
所表示之基中之氫原子經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸基或含有雜環之碳原子數為2~20之基取代之情形,且存在R1
及R2
所表示之基中之亞甲基被取代為-O-、-CO-、-COO-、-OCO-、-NR3
-、-NR3
CO-、-S-、-CS-、-SO2
-、-SCO-、-COS-、-OCS-、不飽和鍵或CSO-之情形, R3
表示氫原子、碳原子數為1~20之烴基, m表示0或1, 式中之*表示鍵結鍵)。
[3] 如[1]或[2]之聚合性組合物,其中著色劑(B)係黑色顏料。
[4] 如[1]至[3]中任一項之聚合性組合物,其中鹼性顯影性化合物(C)係下述通式(II)所表示之鹼性顯影性化合物;
[化2](式中,R11
、R13
及R15
分別獨立地表示氫原子或甲基,R12
、R14
及R16
分別獨立地表示碳原子數為1~20之烴基或含有雜環之碳原子數為2~20之基, 於R13
及R14
存在複數個之情形時,存在相同之情形亦存在不同之情形, Y1
、Y2
及Y3
表示直接鍵、碳原子數為1~20之烴基或含有雜環之碳原子數為2~20之基, 於Y2
存在複數個之情形時,存在相同之情形亦存在不同之情形, Z1
、Z2
及Z3
表示碳原子數為1~20之烴基或含有雜環之碳原子數為2~20之基, 於Z2
存在複數個之情形時,存在相同之情形亦存在不同之情形, 存在R12
、R14
、R16
、Y1
、Y2
、Y3
、Z1
、Z2
及Z3
所表示之基中之氫原子經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、巰基、異氰酸基或含有雜環之基取代之情形,且亦存在R12
、R14
、R16
、Y1
、Y2
、Y3
、Z1
、Z2
及Z3
所表示之基中之亞甲基被取代為-O-、-CO-、-COO-、-OCO-、-S-、-SO2
-、-SCO-或-COS-之情形, n表示0或10以下之正數,a表示0或4以下之正數,b表示0或3以下之正數,c表示0或4以下之正數,於n為2以上之情形時,b存在相同之情形亦存在不同之情形)。
[5] 一種黑色矩陣用感光性組合物,其含有如[1]~[4]中任一項之聚合性組合物。
[6] 一種黑柱間隔物用感光性組合物,其含有如[1]~[4]中任一項之聚合性組合物。
[7] 一種硬化物之製造方法,其係使用如[1]~[4]中任一項之聚合性組合物、如[5]之黑色矩陣用感光性組合物或如[6]之黑柱間隔物用感光性組合物,藉由光照射或加熱而製造硬化物之方法。
[8] 一種硬化物,其係如[1]~[4]中任一項之聚合性組合物、如[5]之黑色矩陣用感光性組合物或如[6]之黑柱間隔物用感光性組合物之硬化物。
[9] 一種顯示器顯示裝置,其含有如[8]之硬化物。
以下,基於較佳之實施形態對本發明之聚合性組合物加以詳細說明。
本發明之聚合性組合物含有作為聚合起始劑之具有羥基之α-胺基苯乙酮化合物、著色劑、鹼性顯影性化合物及除該鹼性顯影性化合物以外之乙烯性不飽和化合物。以下,關於各成分而順次加以說明。
<聚合起始劑(A)> 本發明之聚合性組合物中所使用之聚合起始劑(A)含有具有羥基之α-胺基苯乙酮化合物(A1)[以下亦記為(A1)成分],且可併用除先前已知之(A1)成分以外之自由基聚合起始劑。
上述自由基聚合起始劑係光自由基聚合起始劑與熱自由基聚合起始劑。自反應性高考慮,更佳為光自由基聚合起始劑。
作為光自由基聚合起始劑,若為藉由光照射而產生自由基者,則並無特別限制,可使用先前已知之化合物,例如可例示苯乙酮系化合物、苯偶醯系化合物、二苯甲酮系化合物、9-氧硫𠮿系化合物及肟酯系化合物等作為較佳者。
所謂(A1)成分係表示於一分子內具有羥基與α-胺基苯乙酮結構之化合物,並無特別限定,可較佳地列舉下述通式(V)所表示之化合物。
[化3](式中,Xr
表示下述通式(i)、(ii)或(iii)所表示之結構, Xs
表示硫原子或NR100
, R100
、R101
、R102
、R103
及R104
分別獨立地表示氫原子、碳原子數為1~12之烷基、苯基、碳原子數為7~20之芳烷基或碳原子數為2~12之烯基,存在該烷基經羥基、羧基、鹵素原子、氰基或硝基取代之情形,且存在該苯基及該芳烷基經碳原子數為1~4之烷基、羥基、羧基、鹵素原子、氰基或硝基取代之情形, 存在R101
與R102
連結而形成3~6員環之雜環之情形,且存在於該雜環中之氮原子上鍵結有R99
之情形, 存在R103
與R104
連結而形成3~6員環之情形, R105
、R106
、R107
及R108
分別獨立地表示氫原子、鹵素原子、氰基、硝基、羥基、羧基或碳原子數為1~12之烷基,存在該烷基經鹵素原子、羧基、氰基、硝基或羥基取代之情形, R99
表示氫原子、碳原子數為1~12之烷基、苯基、碳原子數為7~20之芳烷基或碳原子數為2~12之烯基,存在該烷基經羥基、羧基、鹵素原子、氰基或硝基取代之情形,且存在該苯基及該芳烷基經碳原子數為1~4之烷基、羥基、羧基、鹵素原子、氰基或硝基取代之情形。 存在上述所列舉之各烷基及上述各芳烷基中之亞甲基被取代為-O-、-S-、-NR117
-、-CO-、-CO-O-、-O-CO-或-O-CO-O-之情形。 R117
表示氫原子、碳原子數為1~12之烷基、苯基、碳原子數為7~20之芳烷基或碳原子數為2~12之烯基,存在該烷基經羥基、羧基、鹵素原子、氰基或硝基取代之情形,且存在該苯基及該芳烷基經碳原子數為1~4之烷基、羥基、羧基、鹵素原子、氰基或硝基取代之情形。 其中,式(V)所表示之化合物於分子中具有至少一個羥基)
[化5]所表示之結構中之亞甲基亦可經-O-、-S-、-NR117
、-CO-、-CO-O-、-O-CO-或-O-CO-O-取代, R111
表示氫原子、鹵素原子、羥基、羧基、氰基、胺基或苯基,存在該苯基經碳原子數為1~4之烷基、羥基、羧基、鹵素原子、氰基或硝基取代之情形,p表示1~12之數)
[化6](式中,R112
、R113
、R114
、R115
及R116
分別獨立地表示氫原子、鹵素原子、氰基、硝基、羥基或碳原子數為1~12之烷基,存在該烷基經鹵素原子、氰基、硝基或羥基取代之情形,且存在該烷基中之亞甲基被取代為-O-、-S-、-NR117
、-CO-、-CO-O-、-O-CO-或-O-CO-O-之情形,存在R106
或R107
與R112
或R116
鍵結而形成環之情形)
作為通式(V)之說明而於上述中所述之各碳原子數為1~12之烷基例如可列舉作為下述通式(I)中之碳原子數為1~20之烴基之例的碳原子數為1~20之烷基中之碳原子數為1~12者。
作為通式(V)之說明而於上述中所述之各碳原子數為1~4之烷基可列舉作為下述通式(I)中之碳原子數為1~20之烴基之例的作為碳原子數為1~20之烷基而後述者中之碳原子數為1~4者。
作為通式(V)之說明而於上述中所述之各碳原子數為7~20之芳烷基例如可列舉:苄基、α-甲基苄基、α,α-二甲基苄基、苯基乙基等。
作為通式(V)之說明而於上述中所述之各碳原子數為2~12之烯基可列舉:乙烯基、1-丙烯基、2-丙烯基、異丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-辛烯基、1-癸烯基等基。
作為通式(V)中之R101
與R102
可連結而形成之3~6員環之雜環,例如可較佳地列舉哌啶環、哌𠯤環、𠰌啉環、內醯胺環等。
作為通式(V)中之R103
與R104
可連結而形成之3~6員環,例如可較佳地列舉環戊烷環、環己烷環、環戊烯環、內酯環、內醯胺環等。
作為通式(V)中之R106
或R107
與R112
或R116
鍵結而成之環,Xs
與左右相鄰之苯環合在一起之結構可列舉:咔唑環、噻嗯環、二苯并噻吩環。
作為通式(V)中之說明而於上述中所述之各鹵素原子可列舉氟、氯、溴、碘。
較佳之(A1)成分例如可列舉下述化合物No.A1-1~11。
作為除(A1)成分以外之苯乙酮系化合物,可列舉:並不具有羥基之α-胺基苯乙酮化合物及α-羥基苯乙酮化合物。
作為除(A1)成分以外之苯乙酮系化合物,例如可列舉:二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、4'-異丙基-2-羥基-2-甲基苯丙酮、2-羥基甲基-2-甲基苯丙酮、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、對二甲基胺基苯乙酮、對第三丁基二氯苯乙酮、對第三丁基三氯苯乙酮、對疊氮苯亞甲基苯乙酮、1-羥基環己基苯基酮、2-甲基-1-[4-(甲硫基)苯基]-2-𠰌啉基丙酮-1、2-苄基-2-二甲基胺基-1-(4-𠰌啉基苯基)-丁酮-1、安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香正丁醚、安息香異丁醚及1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮等。
作為苯偶醯系化合物,可列舉苯偶醯等。
作為二苯甲酮系化合物,例如可列舉:二苯甲酮、鄰苯甲醯基苯甲酸甲酯、米其勒酮、4,4'-雙二乙基胺基二苯甲酮、4,4'-二氯二苯甲酮及4-苯甲醯基-4'-甲基二苯硫醚等。
作為肟酯系化合物,可列舉具有上述通式(I)所表示之基的肟酯化合物(A2)等,其可藉由與上述光自由基聚合起始劑中之(A1)成分併用而成為高感度,因此可較佳地用於本發明之聚合性組合物中。
上述通式(I)中之R1
~R3
所表示之碳原子數為1~20之烴基並無特別限定,較佳為表示碳原子數為1~20之烷基、碳原子數為2~20之烯基、碳原子數為3~20之環烷基、碳原子數為4~20之環烷基烷基、碳原子數為6~20之芳基或碳原子數為7~20之芳烷基等。自用作聚合起始劑(A)之情形時之感度良好考慮,更佳為碳原子數為1~10之烷基、碳原子數為2~10之烯基、碳原子數為3~10之環烷基、碳原子數為4~10之環烷基烷基、碳原子數為6~10之芳基或碳原子數為7~10之芳烷基等。
作為上述碳原子數為1~20之烷基,例如可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、第三戊基、己基、庚基、辛基、異辛基、2-乙基己基、第三辛基、壬基、異壬基、癸基、異癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基及二十烷基等。作為上述碳原子數為1~10之烷基,例如可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、第三戊基、己基、庚基、辛基、異辛基、2-乙基己基、第三辛基、壬基、異壬基、癸基及異癸基等。
作為上述碳原子數為2~20之烯基,例如可列舉:乙烯基、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基、5-己烯基、2-庚烯基、3-庚烯基、4-庚烯基、3-辛烯基、3-壬烯基、4-癸烯基、3-十一碳烯基、4-十二碳烯基、3-環己烯基、2,5-環己二烯基-1-甲基、及4,8,12-十四碳三烯基烯丙基等。作為上述碳原子數為2~10之烯基,例如可列舉:乙烯基、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基、5-己烯基、2-庚烯基、3-庚烯基、4-庚烯基、3-辛烯基、3-壬烯基及4-癸烯基等。
所謂上述碳原子數為3~20之環烷基係表示具有3~20個碳原子之飽和單環式或飽和多環式烷基。例如可列舉:環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、金剛烷基、十氫萘基、八氫并環戊二烯、雙環[1.1.1]戊基及十四氫蒽基等。作為上述碳原子數為3~10之環烷基,例如可列舉:環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、金剛烷基、十氫萘基、八氫并環戊二烯及雙環[1.1.1]戊基等。
所謂上述碳原子數為4~20之環烷基烷基係表示烷基之氫原子經環烷基取代之具有4~20個碳原子之基。例如可列舉:環丙基甲基、環丁基甲基、環戊基甲基、環己基甲基、環庚基甲基、環辛基甲基、環壬基甲基、環癸基甲基、2-環丁基乙基、2-環戊基乙基、2-環己基乙基、2-環庚基乙基、2-環辛基乙基、2-環壬基乙基、2-環癸基乙基、3-環丁基丙基、3-環戊基丙基、3-環己基丙基、3-環庚基丙基、3-環辛基丙基、3-環壬基丙基、3-環癸基丙基、4-環丁基丁基、4-環戊基丁基、4-環己基丁基、4-環庚基丁基、4-環辛基丁基、4-環壬基丁基、4-環癸基丁基、3-金剛烷基丙基及3-十氫萘基丙基等。作為上述碳原子數為4~10之環烷基烷基,例如可列舉:環丙基甲基、環丁基甲基、環戊基甲基、環己基甲基、環庚基甲基、環辛基甲基、環壬基甲基、2-環丁基乙基、2-環戊基乙基、2-環己基乙基、2-環庚基乙基、2-環辛基乙基、3-環丁基丙基、3-環戊基丙基、3-環己基丙基、3-環庚基丙基、4-環丁基丁基、4-環戊基丁基及4-環己基丁基等。
作為上述碳原子數為6~20之芳基,例如可列舉:苯基、甲苯基、二甲苯基、乙基苯基、萘基、蒽基、菲基等,或經一個以上之上述烷基、上述烯基或羧基、鹵素原子等取代之苯基、聯苯基、萘基、蒽基等,例如4-氯苯基、4-羧基苯基、4-乙烯基苯基、4-甲基苯基、2,4,6-三甲基苯基等。作為上述碳原子數為6~10之芳基,例如可列舉:苯基、甲苯基、二甲苯基、乙基苯基及萘基等,或經一個以上之上述烷基、上述烯基或羧基、鹵素原子等取代之苯基、聯苯基、萘基、蒽基等,例如4-氯苯基、4-羧基苯基、4-乙烯基苯基、4-甲基苯基、2,4,6-三甲基苯基等。
所謂上述碳原子數為7~20之芳烷基係表示烷基之氫原子經上述碳原子數為6~20之芳基中的碳原子數為6~19之芳基取代之具有7~20個碳原子之基。例如可列舉:苄基、α-甲基苄基、α,α-二甲基苄基、苯基乙基及萘基丙基等。作為上述碳原子數為7~10之芳烷基,表示烷基之氫原子經上述碳原子數為6~20之芳基中的碳原子數為6~9之芳基取代之具有7~10個碳原子之基,例如可列舉:苄基、α-甲基苄基、α,α-二甲基苄基及苯基乙基等。
於存在上述通式(I)中之R1
及R2
所表示之含有雜環之碳原子數為2~20之基以及R1
及R2
所表示之基中之氫原子經取代之情形時,含有雜環之碳原子數為2~20之基並無特別限定,例如可列舉:吡咯基、吡啶基、吡啶基乙基、嘧啶基、嗒𠯤基、哌𠯤基、哌啶基、吡喃基、吡喃基乙基、吡唑基、三𠯤基、三𠯤基甲基、吡咯啶基、喹啉基、異喹啉基、咪唑基、苯并咪唑基、三唑基、呋喃基(furyl)、呋喃基(furanyl)、苯并呋喃基、噻吩基(thienyl)、噻吩基(thiophenyl)、苯并噻吩基、噻二唑基、噻唑基、苯并噻唑基、㗁唑基、苯并㗁唑基、異噻唑基、異㗁唑基、吲哚基、𠰌啉基、硫代𠰌啉基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二氧基咪唑啶-3-基及2,4-二氧基㗁唑啶-3-基等,若包含取代基等而具體地記載,則可列舉具有下述結構之基等。
作為上述式中之R所表示之碳原子數為1~6之烷基,可列舉作為上述碳原子數為1~20之烷基而例示者中之碳原子數為1~6者。 作為上述式中之Z所表示之碳原子數為1~6之伸烷基,可列舉:亞甲基、伸乙基、伸丙基、甲基伸乙基、伸丁基、1-甲基伸丙基、2-甲基伸丙基、1,2-二甲基伸丙基、1,3-二甲基伸丙基、1-甲基伸丁基、2-甲基伸丁基、3-甲基伸丁基、4-甲基伸丁基、2,4-二甲基伸丁基、1,3-二甲基伸丁基、伸戊基、伸己基等直鏈或支鏈之伸烷基。
作為通式(I)及(III)之註釋中所記載之各鹵素原子,可列舉氟、氯、溴、碘。
本說明書中,作為存在對各通式(I)或(IV)之註釋中所記載之基中之亞甲基進行取代之情形之不飽和鍵,可列舉-C=C-、-C≡C-等。
具有上述通式(I)所表示之基之化合物中,較佳為下述通式(III)所表示之化合物,其感度特別高,因此可用於本發明之聚合性組合物中。
[化10](式中,R1
、R2
及m分別與通式(I)中之R1
、R2
及m相同, R21
及R22
分別獨立地表示氫原子、硝基、氰基、碳原子數為1~20之烷基、碳原子數為6~20之芳基、碳原子數為7~20之芳烷基或含有雜環之碳原子數為2~20之基, X1
表示氧原子、硫原子、硒原子、CR23
R24
、CO、NR25
或PR26
, X2
表示無鍵結、直接鍵、碳原子數為1~20之烴基、CO,R23
~R26
分別獨立地表示氫原子、碳原子數為1~20之烴基或含有雜環之碳原子數為2~20之基,且亦存在R21
~R26
所表示之基中之氫原子經鹵素原子、硝基、氰基、羥基、羧基或雜環基取代之情形, 亦存在R21
~R26
所表示之基中之亞甲基於氧不相鄰之條件下取代為-O-或-CO-之情形, 亦存在R21
~R26
分別獨立地與鄰接之任意苯環成為一體而形成環之情形, g表示0~4之數, h表示0~3之數)。
上述通式(III)中之R23
~R26
所表示之碳原子數為1~20之烴基分別與通式(I)之R1
~R3
所表示之碳原子數為1~20之烴基相同。又,作為通式(III)中之X2
所表示之碳原子數為1~20之烴基,可列舉自作為通式(I)之R1
~R3
所表示之碳原子數為1~20之烴基而列舉的各基中除去一個氫原子而成之二價基。 上述通式(III)中之R21
及R22
所表示之碳原子數為1~20之烷基、碳原子數為6~20之芳基、碳原子數為7~20之芳烷基分別與關於作為R1
~R3
所表示之碳原子數為1~20之烴基之例的上述碳原子數為1~20之烷基、上述碳原子數為6~20之芳基、上述碳原子數為7~20之芳烷基而於上述中所述者相同。
上述通式(III)中之R21
~R26
所表示的含有雜環之碳原子數為2~20之基與R1
及R2
所表示之含有雜環之碳原子數為2~20之基相同。
作為上述肟酯化合物(A2),例如可列舉下述所示之化合物No.A2-1~No.A2-14。但本發明中所使用之肟酯化合物(A2)並不受以下化合物任何限制。
作為其他自由基聚合起始劑,可列舉:2,4,6-三甲基苯甲醯基二苯基氧化膦等氧化膦系化合物及雙(環戊二烯基)-雙[2,6-二氟-3-(吡咯-1-基)]鈦等二茂鈦系化合物等。
作為市售之自由基起始劑,可列舉:Adeka Optomer N-1414、N-1717、N-1919、ADEKA ARKLS NCI-831、NCI-930(以上由ADEKA公司製造);IRGACURE184、IRGACURE369、IRGACURE651、IRGACURE907、IRGACURE OXE 01、IRGACURE OXE 02、IRGACURE784(以上由巴斯夫公司製造);TR-PBG-304、TR-PBG-305、TR-PBG-309及TR-PBG-314(以上由TRONLY公司製造)等。
作為熱自由基聚合起始劑,若為藉由加熱而產生自由基者,則並無特別限制,可使用先前已知之化合物,例如可例示偶氮系化合物、過氧化物及過硫酸鹽等作為較佳者。
作為偶氮系化合物,可列舉:2,2'-偶氮雙異丁腈、2,2'-偶氮雙(異丁酸甲酯)、2,2'-偶氮雙-2,4-二甲基戊腈、1,1'-偶氮雙(1-乙醯氧基-1-苯基乙烷)等。
作為過氧化物,可列舉:苯甲醯過氧化物、二第三丁基苯甲醯過氧化物、過氧化特戊酸第三丁酯及過氧化二碳酸二(4-第三丁基環己酯)等。
作為過硫酸鹽,可列舉:過硫酸銨、過硫酸鈉及過硫酸鉀等過硫酸鹽等。
作為(A1)成分以外之上述聚合起始劑(A),具有羥基之聚合起始劑由於可提供液晶污染性低、且電特性優異之顯示器顯示裝置而尤佳。
於通式(III)中,於X1
為硫原子、X2
無鍵結之情形時,成為例如上述化合物No.A2-1~A2-7所表示之具有二苯硫醚骨架之肟酯系化合物,於如下方面而言較佳:藉由併用作為聚合起始劑,可獲得感度良好之聚合性組合物。
於通式(III)中,於X1
為NR55
、X2
為直接鍵之情形時,成為例如上述化合物No.A2-8~A2-14所表示之具有咔唑骨架之肟酯系化合物,於可獲得感度良好之聚合性組合物之方面而言尤佳。
上述聚合起始劑(A)可使用到此為止所例示之一種或混合使用兩種以上。
於本發明之聚合性組合物中,上述聚合起始劑(A)之含量並無特別限定,相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,自硬化性良好之方面考慮較佳為0.1~20質量份、更佳為0.3~10質量份、更佳為0.3~5質量份。於聚合起始劑(A)之含量為上述範圍內之情形時,可獲得硬化性良好、且並不伴隨著聚合起始劑析出之保存穩定性優異之聚合性組合物,因此較佳。 例如於形成厚度為2~5 μm之硬化膜之情形時,聚合起始劑(A)之含量並無特別限定,相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,較佳為0.1~20質量份、更佳為0.3~10質量份、更佳為0.3~5質量份。 又,自彈性回覆、介電常數、電特性等方面考慮,於上述聚合起始劑(A)中,(A1)成分之比例較佳為30質量%以上,且較佳為50質量%以上85質量%以下。又,於將(A1)成分與具有式(I)所表示之基之化合物併用之情形時,(A1)成分:具有式(I)所表示之基之化合物之質量比(前者:後者)較佳為2~5:1,更佳為2~3:1。
<著色劑(B)> 作為本發明之聚合性組合物中所使用之著色劑(B),可使用顏料或染料。作為顏料及染料,可分別使用無機有色材料或有機有色材料。該等可單獨使用或混合使用兩種以上。此處,所謂顏料是表示不溶於後述溶劑中之著色劑,亦包含無機或有機有色材料中之不溶於溶劑中者、或對無機或有機染料進行了色澱化者。
作為上述顏料,可列舉:藉由爐法、槽法或熱裂法而獲得之碳黑、或乙炔黑、科琴黑或燈黑等碳黑;藉由環氧樹脂對上述碳黑進行調整或被覆而成者;將上述碳黑預先於溶劑中進行分散於樹脂中之處理而由20~200 mg/g樹脂被覆而成者;對上述碳黑進行酸性或鹼性表面處理而成者;平均粒徑為8 nm以上且DBP吸油量為90 ml/100 g以下之碳黑;由950℃之揮發分中之CO及CO2
而算出之總氧量相對於每100 m2
表面積為9 mg以上之碳黑;以石墨化碳黑、石墨、活性碳、碳纖維、碳奈米管、微米螺旋碳纖維(carbon micro-coil)、碳奈米角、碳氣凝膠、富勒烯、苯胺黑、顏料黑7、鈦黑、內醯胺黑及苝黑等為代表之黑色顏料;氧化鉻綠、米洛麗藍、鈷綠、鈷藍、錳系、亞鐵氰化物、磷酸鹽群青、鐵藍、群青、天藍、濃綠、翡翠綠、硫酸鉛、黃丹、鋅黃、鐵丹(紅色氧化鐵(III))、鎘紅、合成鐵黑、棕土、色澱顏料等有機或無機顏料。
上述顏料中,自遮光性高考慮,較佳為使用黑色顏料,自液晶污染性低考慮,更佳為使用以內醯胺黑及苝黑等為代表之有機系黑色顏料。
作為上述顏料,亦可使用市售品,例如可列舉:顏料紅1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、254、228、240及254;顏料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65及71;顏料黃1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180及185;顏料綠7、10、36及58;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62及64;顏料紫1、19、23、27、29、30、32、37、40及50等。
作為上述染料,例如可列舉:亞硝基化合物、硝基化合物、偶氮化合物、重氮化合物、𠮿化合物、喹啉化合物、蒽醌化合物、香豆素化合物、花青化合物、酞菁化合物、異吲哚啉酮化合物、異吲哚啉化合物、喹吖啶酮化合物、蒽締蒽酮化合物、芘化合物、苝化合物、吡咯并吡咯二酮化合物、硫靛藍化合物、二㗁 𠯤化合物、三苯基甲烷化合物、喹酞酮化合物、萘四羧酸、偶氮染料、花青染料金屬錯合物等。
於本發明之聚合性組合物中,上述著色劑(B)之含量並無特別限定,相對於下述鹼性顯影性化合物(C)100質量份而言較佳為10~500質量份、更佳為10~300質量份、進而較佳為10~200質量份。於著色劑(B)之含量為上述範圍內之情形時,聚合性組合物成為並不伴隨著色劑凝聚之保存穩定性優異者,聚合性組合物之硬化物之遮光性變高,因此較佳。 例如於形成厚度為1~3 μm之硬化物之情形時,著色劑(B)之含量並無特別限定,相對於鹼性顯影性化合物(C)100質量份而言較佳為10~500質量份、更佳為10~300質量份、進而較佳為10~200質量份。
<鹼性顯影性化合物(C)> 本發明之鹼性顯影性化合物(C)係具有親水性基、且顯示出鹼性顯影性之化合物。於本發明中,作為鹼性顯影性化合物(C),若滿足上述條件,則可使用先前所使用之化合物。 作為上述親水性基,可列舉:羥基、硫醇基、羧基、磺基、胺基、醯胺基或其鹽等,羥基及羧基由於鹼性顯影性化合物(C)於鹼中之顯影性高而較佳。 鹼性顯影性化合物(C)中之親水性基之較佳之官能基當量(包含1當量親水性基之高分子化合物之質量)為50~10000。 鹼性顯影性化合物(C)之較佳之分子量係重量平均分子量為2000~10000,尤佳為3000~6000。又,數平均分子量為1000~8000,尤其是2000~5000。於鹼性顯影性化合物(C)之分子量為上述範圍之情形時,可獲得顯影性優異、且耐化學品性優異之硬化物,因此較佳。
上述鹼性顯影性化合物(C)之酸值較佳為10~200 mg/KOH、進而較佳為30~150 mg/KOH。若酸值未達10 mg/KOH,則存在無法充分獲得鹼性顯影性之情形,若大於200 mg/KOH,則存在高分子化合物之製造困難之虞。此處,所謂酸值係依據JIS K 0050及JIS K 0211者。
作為鹼性顯影性化合物(C),具體而言可使用:上述通式(II)所表示之化合物、丙烯酸酯之共聚物;酚系及/或甲酚酚醛清漆環氧樹脂;具有多官能環氧基之聚苯基甲烷型環氧樹脂;環氧丙烯酸酯樹脂;具有於下述通式(IV)所表示之環氧化合物等上加成有不飽和一元酸之結構的環氧加成化合物;具有藉由酯化反應而獲得之結構之樹脂(不飽和化合物)等,上述酯化反應係具有於下述通式(IV)所表示之環氧化合物上加成有不飽和一元酸之結構的環氧加成化合物與多元酸酐之酯化反應。
[化13](式中,M4
表示選自直接鍵、碳原子數為1~20之烴基、-O-、-S-、-SO2
-、-SS-、-SO-、-CO-、-OCO-或下述式(a)、(b)、(c)或(d)所表示之群之取代基, 存在M4
所表示之碳原子數為1~20之烴基中之氫原子經鹵素原子取代之情形,R31
、R32
、R33
、R34
、R35
、R36
、R37
及R38
(以下亦記載為「R31
~R38
」)分別獨立地表示氫原子、碳原子數為1~20之烴基、或鹵素原子,k為0~10之數,於k≧1之情形時,存在複數個之R31
~R38
及M4
分別存在相同之情形,亦存在不同之情形)
[化14](式中,R39
表示碳原子數為1~20之烴基, R40
、R41
、R42
、R43
、R44
、R45
、R46
、R47
、R48
、R49
、R50
、R51
、R52
、R53
、R54
、R55
、R56
、R57
、R58
、R59
、R60
、R61
、R62
、R63
、R64
、R65
、R66
、R67
及R68
(以下亦記載為「R40
~R68
」)分別獨立地表示氫原子、碳原子數為1~20之烴基、含有雜環之碳原子數為2~20之基、或鹵素原子, 存在R31
~R38
及R40
~R68
所表示之基中之亞甲基被取代為不飽和鍵、-O-或-S-之情形, 存在R40
與R41
、R41
與R42
、R42
與R43
、R43
與R44
、R45
與R46
、R46
與R47
、R47
與R48
、R53
與R54
、R54
與R55
、R55
與R56
、R61
與R62
、R62
與R63
、R63
與R64
、R65
與R66
、R66
與R67
及R67
與R68
鍵結而形成環之情形, (a)、(b)、(c)及(d)所表示之基中之*表示鍵結鍵)
藉由使用上述通式(II)所表示之鹼性顯影性化合物,由聚合性組合物所獲得之硬化物之耐化學品性優異,因此較佳。
若使用具有於上述通式(IV)所表示之環氧化合物上加成有不飽和一元酸之結構的環氧加成化合物;或作為藉由酯化反應(該酯化反應係具有於上述通式(IV)所表示之環氧化合物上加成有不飽和一元酸之結構之環氧加成化合物與多元酸酐之酯化反應)而獲得之反應產物之鹼性顯影性化合物,則聚合性組合物之感度變高,由該聚合性組合物而獲得之硬化物之彈性回覆率優異,因此較佳。
自著色劑(B)之分散性變良好、且耐熱性良好考慮,上述鹼性顯影性化合物(C)較佳為上述通式(IV)所表示之環氧化合物;於上述通式(IV)所表示之環氧化合物上加成不飽和一元酸而成之具有下述結構[(e)]之環氧化合物;或藉由該不飽和化合物與多元酸酐之酯化反應而獲得之具有下述結構[(f)]之不飽和化合物。
於上述通式(IV)所表示之鹼性顯影性化合物中,M4
為(b)或(c)所表示之基之情形時,由該聚合性組合物所獲得之硬化物之耐溶劑性變良好,因此尤佳。
上述通式(II)中之R12
、R14
、R16
、Y1
~Y3
及Z1
~Z3
所表示之碳原子數為1~20之烴基可列舉與通式(I)之說明中所上述之碳原子數為1~20之烴基相同者。
於存在上述通式(II)中之R12
、R14
、R16
、Y1
~Y3
及Z1
~Z3
所表示之含有雜環之碳原子數為2~20之基以及R12
、R14
、R16
、Y1
、Y2
、Y3
、Z1
、Z2
及Z3
所表示之基中之氫原子經取代之情形時,含有雜環之碳原子數為2~20之基可列舉與通式(I)之說明中所上述之含有雜環之碳原子數為2~20之基相同者。
上述通式(IV)中之M4
及R31
~R68
所表示之碳原子數為1~20之烴基可列舉與通式(I)之說明中所上述之碳原子數為1~20之烴基相同者。
作為上述通式(IV)中之R40
~R68
所表示之含有雜環之碳原子數為2~20之基,可列舉與通式(I)之說明中所上述之含有雜環之碳原子數為2~20之基相同者。
作為對上述通式(IV)中之M4
所表示之碳原子數為1~20之烴基之氫原子進行取代之鹵素原子及R31
~R68
所表示之鹵素原子,可列舉氟、氯、溴、碘。
作為上述通式(IV)中之R40
與R41
、R41
與R42
、R42
與R43
、R43
與R44
、R45
與R46
、R46
與R47
、R47
與R48
、R53
與R54
、R54
與R55
、R55
與R56
、R61
與R62
、R62
與R63
、R63
與R64
、R65
與R66
、R66
與R67
及R67
與R68
鍵結而形成之環,例如可列舉:環戊烷、環己烷、環戊烯、苯、吡咯啶、吡咯、哌𠯤、𠰌啉、硫代𠰌啉、四氫吡啶、內酯環及內醯胺環等5~7員環以及萘及蒽等縮合環等。
上述不飽和一元酸係表示於結構中具有不飽和鍵,且於一分子中具有一個可電離而成為氫離子之氫原子的酸。 作為上述不飽和一元酸,例如可列舉:丙烯酸、甲基丙烯酸、丁烯酸、桂皮酸、山梨酸及甲基丙烯酸羥基乙酯-馬來酸酯、甲基丙烯酸羥基丙酯-馬來酸酯、丙烯酸羥基丙酯-馬來酸酯及二環戊二烯-馬來酸酯等。
又,作為於上述不飽和一元酸起作用之後起作用之上述多元酸酐,可列舉:聯苯四羧酸二酐、四氫鄰苯二甲酸酐、琥珀酸酐、聯苯四甲酸二酐、馬來酸酐、偏苯三甲酸酐、均苯四甲酸二酐、2,2'-3,3'-二苯甲酮四羧酸二酐、乙二醇雙脫水偏苯三酸酯、甘油三脫水偏苯三酸酯、六氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、耐地酸酐、甲基耐地酸酐、三烷基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、5-(2,5-二側氧四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-馬來酸酐加成物、十二碳烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等。
上述環氧化合物、上述不飽和一元酸及上述多元酸酐之反應莫耳比較佳為如下所示地設定。 亦即,上述環氧加成化合物較佳為以相對於上述環氧化合物之環氧基1個而言,上述不飽和一元酸之羧基成為0.1~1.0個之比率進行加成,又,上述反應產物較佳為相對於上述環氧加成物之羥基1個而言,上述多元酸酐之酸酐結構成為0.1~1.0個之比率。 上述通式(IV)所表示之環氧化合物、上述不飽和一元酸及上述多元酸酐之反應可依照慣例而進行。
為了調整酸值而改良本發明之聚合性組合物、BM用感光性組合物及BCS用感光性組合物之顯影性,可與上述鹼性顯影性化合物(C)一同而進一步使單官能或多官能環氧化合物反應。上述鹼性顯影性化合物(C)之固形物成分之酸值較佳為5~120 mgKOH/g之範圍,單官能或多官能環氧化合物之使用量較佳為以滿足上述酸值之方式選擇。
作為上述單官能環氧化合物,可列舉:甲基丙烯酸縮水甘油酯、甲基縮水甘油醚、乙基縮水甘油醚、丙基縮水甘油醚、異丙基縮水甘油醚、丁基縮水甘油醚、異丁基縮水甘油醚、第三丁基縮水甘油醚、戊基縮水甘油醚、己基縮水甘油醚、庚基縮水甘油醚、辛基縮水甘油醚、壬基縮水甘油醚、癸基縮水甘油醚、十一烷基縮水甘油醚、十二烷基縮水甘油醚、十三烷基縮水甘油醚、十四烷基縮水甘油醚、十五烷基縮水甘油醚、十六烷基縮水甘油醚、2-乙基己基縮水甘油醚、烯丙基縮水甘油醚、炔丙基縮水甘油醚、對甲氧基乙基縮水甘油醚、苯基縮水甘油醚、對甲氧基縮水甘油醚、對丁基苯酚縮水甘油醚、甲苯基縮水甘油醚、2-甲基甲苯基縮水甘油醚、4-壬基苯基縮水甘油醚、苄基縮水甘油醚、對異丙苯基苯基縮水甘油醚、三苯甲基縮水甘油醚、甲基丙烯酸2,3-環氧丙酯、環氧化大豆油、環氧化亞麻仁油、丁酸縮水甘油酯、一氧化乙烯基環己烷、1,2-環氧-4-乙烯基環己烷、環氧苯乙烷、氧化蒎烯、甲基環氧苯乙烷、環氧環己烷、環氧丙烷、下述環氧化合物No.E1、No.E2等。
作為上述多官能環氧化合物,若使用選自由雙酚型環氧化合物及縮水甘油醚類所構成之群中之一種以上化合物,則可獲得特性進一步良好之聚合性組合物,因此較佳。 作為上述雙酚型環氧化合物,除了可使用上述通式(IV)所表示之環氧化合物以外,例如亦可使用氫化雙酚型環氧化合物等雙酚型環氧化合物。 又,作為上述縮水甘油醚類,可使用乙二醇二縮水甘油醚、丙二醇二縮水甘油醚、1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、1,8-辛二醇二縮水甘油醚、1,10-癸二醇二縮水甘油醚、2,2-二甲基-1,3-丙二醇二縮水甘油醚、二乙二醇二縮水甘油醚、三乙二醇二縮水甘油醚、四乙二醇二縮水甘油醚、六乙二醇二縮水甘油醚、1,4-環己烷二甲醇二縮水甘油醚、1,1,1-三(縮水甘油氧基甲基)丙烷、1,1,1-三(縮水甘油氧基甲基)乙烷、1,1,1-三(縮水甘油氧基甲基)甲烷、1,1,1,1-四(縮水甘油氧基甲基)甲烷等。 另外,亦可使用:酚系酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、甲酚酚醛清漆型環氧化合物、雙酚A酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物等酚醛清漆型環氧化合物;3,4-環氧-6-甲基環己烷羧酸-3,4-環氧-6-甲基環己基甲酯、3,4-環氧環己烷羧酸-3,4-環氧環己基甲酯、1-環氧乙基-3,4-環氧環己烷等脂環式環氧化合物;鄰苯二甲酸二縮水甘油酯、四氫鄰苯二甲酸二縮水甘油酯、二聚酸縮水甘油酯等縮水甘油酯類;四縮水甘油基二胺基二苯基甲烷、三縮水甘油基對胺基苯酚、N,N-二縮水甘油基苯胺等縮水甘油基胺類;1,3-二縮水甘油基-5,5-二甲基乙內醯脲、異氰尿酸三縮水甘油酯等雜環式環氧化合物;二氧化二環戊二烯等二氧化物化合物;萘型環氧化合物;三苯基甲烷型環氧化合物;二環戊二烯型環氧化合物等。
作為鹼性顯影性化合物(C),亦可適宜使用市售品。 作為該市售品,例如可列舉:SPC1000、SPC-2000、SPC-3000、SPRR-1X、SPRR-2X、SPRR-3X、SPRR-5X、SPRR-6X、SPRR-7X、SPRR-8X、SPRR-9X、SPRR-10X、SPRR-11X、SPRR-12X、SPRR-13X、SPRR-14X、SPRR-15X、SPRR-16X、SPRR-17X、SPRR-18X、SPRR-19X、SPRR-20X、SPRR-21X(以上由昭和電工公司製造)、JET2000、AGOR1060、AGOR3060、ORGA1060、ORGA2060(以上由大阪有機化學公司製造)、CCR-1171H(日本化藥公司製造)等。
於本發明之聚合性組合物中,鹼性顯影性化合物(C)之含量並無特別限定,相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,較佳為10~90質量份、更佳為20~80質量份,進而較佳為30~80質量份。於鹼性顯影性化合物(C)之含量為上述範圍內之情形時,聚合性組合物之鹼性顯影性良好,因此較佳。 例如於形成厚度為2~5 μm之硬化膜之情形時,鹼性顯影性化合物(C)之含量並無特別限定,相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,較佳為10~90質量份、更佳為20~80質量份、進而較佳為30~80質量份。 又,於鹼性顯影性化合物(C)含有通式(II)所表示之化合物之情形時,其量相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,較佳為10~60質量份、更佳為20~50質量份。又,於含有環氧加成化合物(其具有於上述通式(IV)所表示之環氧化合物上加成有不飽和一元酸之結構)、或藉由該環氧加成化合物與多元酸酐之酯化反應而獲得之反應產物之情形時,其量相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,較佳為5~80質量份、更佳為5~40質量份。所謂上述之環氧加成化合物及藉由該環氧加成化合物與多元酸酐之酯化反應而獲得之反應產物之含量,於僅含有該環氧加成化合物及該反應產物之一者之情形時為其量,於含有兩者之情形時為其合計量。
<乙烯性不飽和化合物(D)> 本發明中所使用之乙烯性不飽和化合物(D)係具有乙烯性不飽和鍵、且並非上述鹼性顯影性化合物(C)之化合物。作為乙烯性不飽和化合物(D),例如可列舉:乙烯、丙烯、丁烯、異丁烯、氯乙烯、偏二氯乙烯、偏二氟乙烯、四氟乙烯等不飽和脂肪族烴;(甲基)丙烯酸、α-氯丙烯酸、伊康酸、馬來酸、檸康酸、富馬酸、雙環庚烯二甲酸、丁烯酸、異丁烯酸、乙烯基乙酸、烯丙基乙酸、桂皮酸、山梨酸、中康酸、琥珀酸單[2-(甲基)丙烯醯氧基乙酯]、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙酯]、ω-羧基聚己內酯單(甲基)丙烯酸酯等在兩末端具有羧基與羥基之聚合物之單(甲基)丙烯酸酯;(甲基)丙烯酸羥基乙酯-馬來酸酯、(甲基)丙烯酸羥基丙酯-馬來酸酯、二環戊二烯-馬來酸酯或具有一個羧基與兩個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等不飽和多元酸;(甲基)丙烯酸-2-羥基乙酯、(甲基)丙烯酸-2-羥基丙酯、(甲基)丙烯酸縮水甘油酯、下述丙烯酸系化合物No.1~No.4、(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸二甲基胺基甲酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸胺基丙酯、(甲基)丙烯酸二甲基胺基丙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸聚(乙氧基)乙酯、(甲基)丙烯酸丁氧基乙氧基乙酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸乙烯酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羥甲基乙烷三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三環癸烷二甲醇二(甲基)丙烯酸酯、異氰尿酸三[(甲基)丙烯醯基乙基]酯、聚酯(甲基)丙烯酸酯低聚物等不飽和一元酸及多元醇或多酚之酯;(甲基)丙烯酸鋅、(甲基)丙烯酸鎂等不飽和多元酸之金屬鹽;馬來酸酐、伊康酸酐、檸康酸酐、甲基四氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐、5-(2,5-二側氧四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-馬來酸酐加成物、十二碳烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等不飽和多元酸之酸酐;(甲基)丙烯醯胺、亞甲基雙(甲基)丙烯醯胺、二伸乙基三胺三(甲基)丙烯醯胺、苯二甲基雙(甲基)丙烯醯胺、α-氯丙烯醯胺、N-2-羥基乙基(甲基)丙烯醯胺等不飽和一元酸及多胺之醯胺;丙烯醛等不飽和醛;(甲基)丙烯腈、α-氯丙烯腈、二氰亞乙烯、烯丙基腈等不飽和腈;苯乙烯、4-甲基苯乙烯、4-乙基苯乙烯、4-甲氧基苯乙烯、4-羥基苯乙烯、4-氯苯乙烯、二乙烯基苯、乙烯基甲苯、乙烯基苯甲酸、乙烯基苯酚、乙烯基磺酸、4-乙烯基苯磺酸、乙烯基苄基甲基醚、乙烯基苄基縮水甘油醚等不飽和芳香族化合物;甲基乙烯基酮等不飽和酮;乙烯基胺、烯丙基胺、N-乙烯基吡咯啶酮、乙烯基哌啶等不飽和胺化合物;烯丙醇、巴豆醇等乙烯醇;乙烯基甲基醚、乙烯基乙基醚、正丁基乙烯基醚、異丁基乙烯基醚、烯丙基縮水甘油醚等乙烯醚;馬來醯亞胺、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺等不飽和醯亞胺類;茚、1-甲基茚等茚類;1,3-丁二烯、異戊二烯、氯戊二烯等脂肪族共軛二烯類;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、聚矽氧烷等在聚合物分子鏈之末端具有單(甲基)丙烯醯基之巨單體類;氯乙烯、偏二氯乙烯、琥珀酸二乙烯酯、鄰苯二甲酸二烯丙酯、磷酸三烯丙酯、異氰尿酸三烯丙酯、乙烯基硫醚、乙烯基咪唑、乙烯基㗁唑啉、乙烯基咔唑、乙烯基吡咯啶酮、乙烯基吡啶、含有羥基之乙烯基單體及聚異氰酸酯化合物之胺基甲酸乙烯酯化合物、含有羥基之乙烯基單體及聚環氧化合物之乙烯基環氧化合物。 上述乙烯性不飽和化合物(D)可單獨使用或混合使用兩種以上。
作為上述乙烯性不飽和化合物,亦可使用市售品。作為該市售品,例如可列舉:Kayarad DPHA、DPEA-12、PEG400DA、THE-330、RP-1040、NPGDA、PET30、R-684(以上由日本化藥公司製造);ARONIX M-215、M-350(以上由東亞合成公司製造);NK-ESTER A-DPH、A-TMPT、A-DCP、A-HD-N、TMPT、DCP、NPG及HD-N(以上由新中村化學工業公司製造);SPC-1000、SPC-3000(以上由昭和電工公司製造);NK-OLIGO U-4HA、U-4H、U-6HA、U-15HA、U-108A、U-1084A、U-200AX、U-122A、U-340A、U-324A、UA-53H、UA-100、AH-600(以上由新中村化學工業公司製造)、UA-306H、AI-600、UA-101T、UA-101I、UA-306T、UA-306I(以上由共榮社化學公司製造)、Artresin UN-9200A、UN-3320HA、UN-3320HB、UN-3320HC、UN-3320HS、SH-380G、SH-500、SH-9832、UN-901T、UN-904、UN-905、UN-906、UN-906S、UN-907、UN-952、UN-953、UN-954、H-91、H-135(以上由根上工業公司製造)、Sartomer CN968、CN975、CN989、CN9001、CN9010、CN9025、CN9029、CN9165、CN2260(以上由沙多瑪公司製造)、EBECRYL8810(大賽璐公司製造)等。
於本發明之聚合性組合物中,乙烯性不飽和化合物(D)之含量並無特別限定,相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,較佳為1~50質量份、更佳為1~30質量份、進而較佳為5~20質量份。於乙烯性不飽和化合物(D)之含量為上述範圍內之情形時,所獲得之硬化物之硬化性及遮光性優異,因此較佳。 例如於形成厚度為1~3 μm之硬化膜之情形時,乙烯性不飽和化合物(D)之含量並無特別限定,相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言,乙烯性不飽和化合物(D)較佳為1~50質量份、更佳為1~30質量份、進而較佳為5~20質量份。
於本發明之聚合性組合物中可進一步加入溶劑。該溶劑通常可視需要使用可溶解或分散上述各成分(聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)等)之溶劑。例如可列舉:甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮及2-庚酮等酮系溶劑;乙醚、二㗁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷及二丙二醇二甲醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸3-甲氧基丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯及TEXANOL等酯系溶劑;乙二醇單甲醚及乙二醇單乙醚等溶纖劑系溶劑;甲醇、乙醇、異或正丙醇、異或正丁醇及戊醇等醇系溶劑;乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、丙二醇-1-單甲醚(PGM)、丙二醇-1-單甲醚-2-乙酸酯(PGMEA)、二丙二醇單甲醚乙酸酯、乙酸3-甲氧基丁酯及丙酸乙氧基乙酯等醚酯系溶劑;苯、甲苯及二甲苯等BTX系溶劑;己烷、庚烷、辛烷及環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯及蒎烯等萜烯系烴油;礦油精、Swasol#310(以上由科斯莫松山石油公司製造)及Solvesso#100(以上由Exxon化學公司製造)等石蠟系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷及1,2-二氯乙烷等鹵化脂肪族烴系溶劑;氯苯等鹵化芳香族烴系溶劑;卡必醇系溶劑、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸及水等,該等溶劑可使用一種或作為兩種以上之混合溶劑而使用。
該等中,酮系溶劑、酯系溶劑及醚酯系溶劑等,尤其是環己酮、乙酸3-甲氧基丁酯、琥珀酸二甲酯及PGMEA等由於在聚合性組合物中抗蝕劑與聚合起始劑之相容性良好而較佳。
若併用PGMEA、乙酸3-甲氧基丁酯、琥珀酸二甲酯,則獲得均勻之塗佈面,因此較佳,進而於上述溶劑之質量基準之比率(PGMEA:乙酸3-甲氧基丁酯:琥珀酸二甲酯)為15~25:2~5:1之情形時尤佳。
於本發明之聚合性組合物中,上述溶劑之含量並無特別限定,較佳為於聚合性組合物之總量100質量%中成為30~95質量%,更佳為50~95質量%。 於溶劑之含量為上述範圍之情形時,成為操作性(聚合性組合物之黏度或潤濕性)、乾燥時之不均之減低及液穩定性(並不伴隨著組合物中所含之成分之析出或沈澱)優異之聚合性組合物,於獲得硬化物時可適宜地控制硬化物之厚度,因此較佳。
於本發明之聚合性組合物中,可視需要進而加入環氧化合物、鹼性顯影性賦予劑、分散劑、潛伏性添加劑、有機聚合物、無機化合物、偶合劑、鏈轉移劑、增感劑、界面活性劑及三聚氰胺化合物、對苯甲醚、對苯二酚、鄰苯二酚、第三丁基兒茶酚及啡噻𠯤等熱聚合抑制劑;可塑劑;接著促進劑;填充劑;消泡劑;調平劑;表面調整劑;抗氧化劑;紫外線吸收劑;分散助劑;抗凝聚劑;觸媒;效果促進劑;交聯劑;增黏劑等慣用之添加物。
作為上述環氧化合物,例如可列舉:甲基縮水甘油醚、2-乙基己基縮水甘油醚、丁基縮水甘油醚、癸基縮水甘油醚、C12~13混合烷基縮水甘油醚、苯基-2-甲基縮水甘油醚、鯨蠟基縮水甘油醚、硬脂基縮水甘油醚、甲基丙烯酸縮水甘油酯、異丙基縮水甘油醚、烯丙基縮水甘油醚、乙基縮水甘油醚、2-甲基辛基縮水甘油醚、苯基縮水甘油醚、4-正丁基苯基縮水甘油醚、4-苯基苯酚縮水甘油醚、甲苯基縮水甘油醚、二溴甲苯基縮水甘油醚、癸基縮水甘油醚、甲氧基聚乙二醇單縮水甘油醚、乙氧基聚乙二醇單縮水甘油醚、丁氧基聚乙二醇單縮水甘油醚、苯氧基聚乙二醇單縮水甘油醚、二溴苯基縮水甘油醚、1,4-丁二醇二縮水甘油醚、1,5-戊二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、新戊二醇二縮水甘油醚、1,1,2,2-四(縮水甘油氧基苯基)乙烷及季戊四醇四縮水甘油醚等縮水甘油醚化物;乙酸縮水甘油酯、硬脂酸縮水甘油酯等縮水甘油酯類;2-(3,4-環氧環己基-5,5-螺-3,4-環氧)環己烷-甲基二㗁烷、亞甲基雙(3,4-環氧環己烷)、丙烷-2,2-二基-雙(3,4-環氧環己烷)、2,2-雙(3,4-環氧環己基)丙烷、伸乙基雙(3,4-環氧環己烷羧酸酯)、己二酸雙(3,4-環氧環己基甲酯)、3,4-環氧環己烷羧酸3,4-環氧環己基甲酯、3,4-環氧-1-甲基己烷羧酸3,4-環氧-1-甲基己酯、6-甲基-3,4-環氧環己烷羧酸6-甲基-3,4-環氧環己基甲酯、3,4-環氧-3-甲基環己烷羧酸3,4-環氧-3-甲基環己基甲酯、3,4-環氧-5-甲基環己烷羧酸3,4-環氧-5-甲基環己基甲酯、1-環氧乙基-3,4-環氧環己烷、1,2-環氧-2-環氧乙基環己烷、二環氧二環戊二烯、3,4-環氧-6-甲基環己基羧酸酯、α-氧化蒎烯、環氧苯乙烷、環氧環己烷及環氧環戊烷等環氧環烷基型化合物及N-縮水甘油基鄰苯二甲醯亞胺等。
作為上述環氧化合物,亦可使用環氧化聚烯烴。所謂環氧化聚烯烴係藉由含有環氧基之單體對聚烯烴進行改性,導入環氧基之聚烯烴。可藉由利用共聚法或接枝法之任意方法使乙烯或碳數為3~20之α-烯烴、含有環氧基之單體、及視需要之其他單體共聚而製造。乙烯或碳數為3~20之α-烯烴、含有環氧基之單體及其他單體可分別單獨聚合,也可以與其他單體複數種聚合。又,亦可藉由過乙酸法對末端具有羥基之非共軛之聚丁二烯之雙鍵進行環氧化而獲得,亦可使用於分子內具有羥基者。又,亦可藉由異氰酸酯對羥基進行胺基甲酸酯化,於此處使含有一級羥基之環氧化合物反應而導入環氧基。
作為上述乙烯或碳數為3~20之α-烯烴,可列舉:乙烯、丙烯、丁烯、異丁烯、1,3-丁二烯、1,4-丁二烯、1,3-戊二烯、2,3-二甲基-1,3-丁二烯、戊二烯、3-丁基-1,3-辛二烯及異戊二烯等。
作為上述含有環氧基之單體,例如可列舉:α,β-不飽和酸之縮水甘油酯、乙烯基苄基縮水甘油醚及烯丙基縮水甘油醚等。作為α,β-不飽和酸之縮水甘油酯,具體而言可列舉:丙烯酸縮水甘油酯、甲基丙烯酸縮水甘油酯及乙基丙烯酸縮水甘油酯等,尤佳為甲基丙烯酸縮水甘油酯。
作為上述環氧化合物,亦可使用市售品。作為適宜之市售品,例如可列舉:Epolight 40E、1500NP、1600、80MF、4000及3002(以上由共榮社化學公司製造);Adeka Glycilol ED-503、ED-503D、ED-503G、ED-523T、ED-513、ED-501、ED-502、ED-509、ED-518、ED-529、Adeka Resin EP-4000、EP-4005、EP-4080及EP-4085(以上由ADEKA公司製造);DENACOL EX-201、EX-203、EX-211、EX-212、EX-221、EX-251、EX-252、EX-711、EX-721、DENACOL EX-111、EX-121、EX-141、EX-142、EX-145、EX-146、EX-147、EX-171、EX-192及EX-731(以上由長瀨化成公司製造);EHPE-3150、Celloxide 2021P、2081、2000及3000(以上由大賽璐公司製造);EPIOL M、EH、L-41、SK、SB、TB及OH(以上由日油公司製造);Epolight M-1230及100MF(以上由共榮社化學公司製造);ARONE OXETANE OXT-121、OXT-221、EXOH、POX、OXA、OXT-101、OXT-211及OXT-212(以上由東亞合成公司製造);Etanacol OXBP及OXTP(以上由宇部興產公司製造);2-羥基乙基乙烯醚、二乙二醇單乙烯醚及4-羥基丁基乙烯醚(以上由丸善石油化學公司製造);DENACOL EX-121、EX-141、EX-142、EX-145、EX-146、EX-147、EX-201、EX-203、EX-711、EX-721、oncoat EX-1020、EX-1030、EX-1040、EX-1050、EX-1051、EX-1010、EX-1011及1012(以上由長瀨化成公司製造);OGSOL PG-100、EG-200、EG-210及EG-250(以上由Osaka Gas Chemicals公司製造);HP4032、HP4032D及HP4700(以上由DIC公司製造);ESN-475V(東都化成公司製造);Marproof G-0105SA及G-0130SP(以上由日油公司製造);EPICLON N-665及HP-7200(以上由DIC公司製造);EOCN-1020、EOCN-102S、EOCN-103S、EOCN-104S、XD-1000、NC-3000、EPPN-501H、EPPN-501HY、EPPN-502H及NC-7000L(以上由日本化藥公司製造)等。
所謂上述鹼性顯影性賦予劑係並不具有自由基聚合性之賦予鹼性顯影性之化合物,作為此種化合物,若為由於具有酸值而可溶於鹼性水溶液中之化合物,則並無特別限定,作為代表性化合物,可列舉鹼可溶性酚醛清漆樹脂(以下簡稱為「酚醛清漆樹脂」)。酚醛清漆樹脂可藉由於酸觸媒之存在下使酚類與醛類縮聚而獲得。
作為上述酚類,例如使用苯酚、鄰甲酚、間甲酚、對甲酚、鄰乙基苯酚、間乙基苯酚、對乙基苯酚、鄰丁基苯酚、間丁基苯酚、對丁基苯酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚、2,3,5-三甲基苯酚、對苯基苯酚、氫醌、兒茶酚、間苯二酚、2-甲基間苯二酚、鄰苯三酚、α-萘酚、雙酚A、二羥基苯甲酸酯及沒食子酸酯等,該等酚類中較佳為苯酚、鄰甲酚、間甲酚、對甲酚、2,5-二甲苯酚、3,5-二甲苯酚、2,3,5-三甲基苯酚、間苯二酚、2-甲基間苯二酚及雙酚A等。該等酚類可單獨使用或者混合使用兩種以上。
作為上述醛類,例如可使用甲醛、多聚甲醛、乙醛、丙醛、苯甲醛、苯基乙醛、α-苯基丙醛、β-苯基丙醛、鄰羥基苯甲醛、間羥基苯甲醛、對羥基苯甲醛、鄰氯苯甲醛、間氯苯甲醛、對氯苯甲醛、鄰硝基苯甲醛、間硝基苯甲醛、對硝基苯甲醛、鄰甲基苯甲醛、間甲基苯甲醛、對甲基苯甲醛、對乙基苯甲醛及對正丁基苯甲醛等,該等化合物中較佳為甲醛、乙醛及苯甲醛等。該等醛類可單獨使用或者混合使用兩種以上。醛類以每1莫耳酚類中較佳為0.7~3莫耳、尤佳為0.7~2莫耳之比例使用。
作為上述酸觸媒,例如可使用鹽酸、硝酸、硫酸等無機酸,或甲酸、草酸、乙酸等有機酸。該等酸觸媒之使用量較佳為於每1莫耳酚類中為1×10-4
~5×10-1
莫耳。於縮合反應中,通常使用水作為反應介質,但於縮合反應中所使用之酚類並不溶解於醛類之水溶液中,自反應初期便成為非勻相系統之情形時,亦可使用親水性溶劑作為反應介質。作為該等親水性溶劑,例如可列舉:甲醇、乙醇、丙醇及丁醇等醇類,或四氫呋喃及二㗁烷等環狀醚類。該等反應介質之使用量通常是每100質量份反應原料中為20~1000質量份。縮合反應之反應溫度可根據反應原料之反應性而適宜調整,通常為10~200℃、較佳為70~150℃。於縮合反應結束後,為了將系統內存在之未反應原料、酸觸媒及反應介質除去,一般使內溫上升至130~230℃,於減壓下蒸餾去除揮發分,其次將熔融之酚醛清漆樹脂流延於鋼製帶等之上而進行回收。 又,亦可藉由如下方式而回收:於縮合反應結束後,於前述親水性溶劑中溶解反應混合物,添加於水、正己烷及正庚烷等沈澱劑中,由此使酚醛清漆樹脂析出,分離析出物而進行加熱乾燥。
作為上述酚醛清漆樹脂以外之例,可列舉:聚羥基苯乙烯或其衍生物、苯乙烯-馬來酸酐共聚物及聚羥基苯甲酸乙烯酯等。
作為上述分散劑,若為可使著色劑(B)分散、穩定化者,則可為任意者,可使用市售之分散劑、例如BYK-Chemie公司製造之BYK系列等,可適宜使用包含具有鹼性官能基之聚酯、聚醚、聚胺基甲酸酯之高分子分散劑,具有氮原子作為鹼性官能基,具有氮原子之官能基為胺及/或其四級鹽,胺值為1~100 mgKOH/g者。
上述潛伏性添加劑係於常溫、光曝光步驟及預烘烤步驟中為惰性,藉由於100~250℃下進行加熱,或於酸/鹼觸媒之存在下、80~200℃下進行加熱使保護基脫離而活化者。作為藉由進行活化而獲得之效果,可列舉抗氧化、紫外線吸收、防污性、再塗佈性及密接性等。 作為上述潛伏性添加劑,可較佳地使用WO2014/021023號說明書中所記載者。
作為上述潛伏性添加劑,可使用市售品,例如可列舉ADEKA ARKLS GPA-5001等。
作為上述有機聚合物,例如可列舉:聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯-丙烯酸乙酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、乙烯-氯乙烯共聚物、乙烯-乙烯基共聚物、聚氯乙烯樹脂、ABS樹脂、尼龍6、尼龍66、尼龍12、聚胺酯樹脂、聚碳酸酯、聚乙烯醇縮丁醛、纖維素酯、聚丙烯醯胺、飽和聚酯、酚樹脂、苯氧基樹脂、聚醯胺醯亞胺樹脂、聚醯胺酸樹脂、環氧樹脂等,該等中較佳為聚苯乙烯、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、環氧樹脂。 亦可藉由與上述鹼性顯影性化合物(C)一同使用上述有機聚合物而改善硬化物之特性。 於使用有機聚合物之情形時,其使用量相對於上述鹼性顯影性化合物(C)100質量份而言較佳為10~500質量份。
作為上述無機化合物,例如可列舉:氧化鎳、氧化鐵、氧化銥、氧化鈦、氧化鋅、氧化鎂、氧化鈣、氧化鉀、氧化矽及氧化鋁等金屬氧化物;層狀黏土礦物、米洛麗藍、碳酸鈣、碳酸鎂、鈷系、錳系、玻璃粉末、雲母、滑石、高嶺土、亞鐵氰化物、各種金屬硫酸鹽、硫化物、硒化物、矽酸鋁、矽酸鈣、氫氧化鋁、鉑、金、銀及銅等,該等中較佳為氧化鈦、氧化矽、層狀黏土礦物、及銀等。
藉由於本發明之聚合性組合物中含有無機化合物,可用作感光性膏組合物。該感光性膏組合物用以形成電漿顯示面板之間隔壁圖案、介電體圖案、電極圖案及黑色矩陣圖案等焙燒物圖案。 又,該等無機化合物例如亦可作為填充劑、抗反射劑、導電劑、穩定劑、阻燃劑、機械強度提高劑、特殊波長吸收劑及撥油墨劑等。
於本發明之聚合性組合物中添加無機化合物之情形時,無機化合物之含量相對於上述鹼性顯影性化合物(C)100質量份而言較佳為0.1~50質量份、更佳為0.5~20質量份,該等無機化合物可使用一種或兩種以上。
作為上述偶合劑,例如可使用二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三甲氧基矽烷等烷基官能性烷氧基矽烷,乙烯基三氯矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、烯丙基三甲氧基矽烷等烯基官能性烷氧基矽烷,3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、2-甲基丙烯醯氧基丙基三甲氧基矽烷等(甲基)丙烯酸酯官能性烷氧基矽烷,γ-縮水甘油氧基丙基三甲氧基矽烷、γ-縮水甘油氧基丙基甲基二乙氧基矽烷、β-(3,4-環氧環己基)乙基三甲氧基矽烷、γ-(3,4-環氧環己基)丙基三甲氧基矽烷等環氧官能性烷氧基矽烷,N-β(胺基乙基)-γ-胺基丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、N-苯基-γ-胺基丙基三甲氧基矽烷等胺基官能性烷氧基矽烷,γ-巰基丙基三甲氧基矽烷等巰基官能性烷氧基矽烷,3-異氰酸酯基丙基三乙氧基矽烷等異氰酸酯基官能性烷氧基矽烷,3-脲基丙基三烷氧基矽烷等脲基官能性烷氧基矽烷,三(三甲氧基矽烷基丙基)異氰尿酸酯等異氰尿酸酯基官能性烷氧基矽烷,四異丙醇鈦、四正丁醇鈦等烷醇鈦類,二辛氧基鈦雙(辛二醇)、二異丙氧基鈦雙(乙醯乙酸乙酯)等鈦螯合物類,四乙醯丙酮酸鋯、三丁氧基單乙醯基丙酮酸鋯等鋯螯合物類,三丁氧基單硬脂酸鋯等鋯醯化物類,甲基三異氰酸酯基矽烷等異氰酸酯基矽烷類等。 藉由添加偶合劑,可使硬化物與基材間(尤其是玻璃)之密接性提高,因此較佳。
作為上述偶合劑,可使用市售品,例如可列舉:KA-1003、KBM-1003、KBE-1003、KBM-303、KBM-403、KBE-402、KBE-403、KBM-1403、KBM-502、KBM-503、KBE-502、KBE-503、KBM-5103、KBM-602、KBM-603、KBE-603,KBM-903,KBE-903,KBE-9103,KBM-573、KBM-575、KBM-6123、KBE-585、KBM-703、KBM-802、KBM-803、KBE-846、KBE-9007、KBM-04、KBE-04、KBM-13、KBE-13、KBE-22、KBE-103、HMDS-3、KBM-3063、KBM-3103C、KPN-3504及KF-99(以上由信越矽酮公司製造)等。
作為上述鏈轉移劑及增感劑,一般使用含有硫原子之化合物。例如硫代乙醇酸、硫代蘋果酸、硫代水楊酸、2-巰基丙酸、3-巰基丙酸、3-巰基丁酸、N-(2-巰基丙醯基)甘胺酸、2-巰基菸鹼酸、3-[N-(2-巰基乙基)胺甲醯基]丙酸、3-[N-(2-巰基乙基)胺基]丙酸、N-(3-巰基丙醯基)丙胺酸、2-巰基乙磺酸、3-巰基丙磺酸、4-巰基丁磺酸、十二烷基(4-甲硫基)苯基醚、2-巰基乙醇、3-巰基-1,2-丙二醇、1-巰基-2-丙醇、3-巰基-2-丁醇、巰基苯酚、2-巰基乙胺、2-巰基咪唑、2-巰基苯并咪唑、2-巰基-3-吡啶醇、2-巰基苯并噻唑、巰基乙酸、三羥甲基丙烷三(3-巰基丙酸酯)及季戊四醇四(3-巰基丙酸酯)等巰基化合物;對該巰基化合物進行氧化而獲得之二硫醚化合物、碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸及3-碘丙磺酸等碘烷基化合物;三羥甲基丙烷三(3-巰基異丁酸酯)、丁二醇雙(3-巰基異丁酸酯)、己二硫醇、癸二硫醇、1,4-二甲基巰基苯、丁二醇雙巰基丙酸酯、丁二醇雙巰基乙酸酯、乙二醇雙巰基乙酸酯、三羥甲基丙烷三巰基乙酸酯、丁二醇雙巰基丙酸酯、三羥甲基丙烷三巰基丙酸酯、三羥甲基丙烷三巰基乙酸酯、季戊四醇四巰基丙酸酯、季戊四醇四巰基乙酸酯、三巰基丙酸三羥基乙酯、下述化合物No.C1、昭和電工公司製造之Karenz PE-1及NR1等。
藉由添加上述鏈轉移劑及增感劑而獲得之硬化物之圖案變得高精細,因此較佳。
作為上述界面活性劑,可使用全氟烷基磷酸酯、全氟烷基碳酸鹽等氟界面活性劑,高級脂肪酸鹼金屬鹽、烷基磺酸鹽、烷基硫酸鹽等陰離子系界面活性劑,高級胺氫鹵酸鹽、四級銨鹽等陽離子系界面活性劑,聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨醇酐脂肪酸酯、脂肪酸單甘油酯等非離子界面活性劑,兩性界面活性劑及矽酮系界面活性劑等界面活性劑,該等亦可組合使用。
作為上述三聚氰胺化合物,可列舉:(聚)羥甲基三聚氰胺、(聚)羥甲基甘脲、(聚)羥甲基苯并胍胺及(聚)羥甲基脲等氮化合物中之活性羥甲基(CH2
OH基)之全部或一部分(至少兩個)烷基醚化而成之化合物。此處,作為構成烷基醚之烷基,可列舉甲基、乙基及丁基,可相互相同亦可不同。又,未烷基醚化之羥甲基可於一分子內自縮合,亦可於兩分子間縮合,其結果形成低聚物成分。具體而言,可使用六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺、四甲氧基甲基甘脲及四丁氧基甲基甘脲等。該等中較佳為六甲氧基甲基三聚氰胺及六丁氧基甲基三聚氰胺等進行了烷基醚化之三聚氰胺。
於本發明之聚合性組合物中,聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)、乙烯性不飽和化合物(D)、溶劑及無機化合物以外之任意成分之含量可根據其使用目的而適宜選擇,只要不損及本發明之效果,則並無特別限制,較佳為相對於聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)之合計100質量份而言合計為20質量份以下。
本發明之BM用感光性組合物係含有聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)作為必須成分,具有感光性及鹼性顯影性,尤其適合形成BM之組合物。
本發明之BCS用感光性組合物係含有聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及乙烯性不飽和化合物(D)作為必須成分,具有感光性及鹼性顯影性,尤其適合形成BCS之組合物。
本發明之聚合性組合物、BM用感光性組合物或BCS用感光性組合物以及硬化物可用於硬化性塗料、清漆、硬化性接著劑、印刷基板、顯示器顯示裝置(彩色電視、PC顯示器、攜帶型資訊終端及數位相機等彩色顯示之液晶顯示面板中之彩色濾光片、各種顯示用途用彩色濾光片、CCD影像感測器之彩色濾光片、觸控面板、電氣發光顯示裝置(微LED之間隔壁材料)、電漿顯示面板、有機EL之黑色間隔壁、粉末塗層、印刷墨水、印刷版、接著劑、凝膠塗層、電子工學用光阻劑、電鍍抗蝕劑、蝕刻阻劑、焊料抗蝕劑、絕緣膜、黑色矩陣、及用以於LCD之製造步驟中形成結構之抗蝕劑、用以封入電氣及電子零件之組合物、阻焊劑、磁記錄材料、微小機械零件、波導、光開關、鍍覆用遮罩、蝕刻遮罩、彩色試驗系統、玻璃纖維纜線塗層、網版印刷用模板、用以藉由立體光刻製造三維物體之材料、全像記錄用材料、圖像記錄材料、微細電子電路、脫色材料、用於圖像記錄材料之脫色材料、使用微膠囊之圖像記錄材料用脫色材料、印刷配線板用光阻劑材料、UV及可見光雷射直接圖像系統用光阻劑材料、印刷電路基板之逐次積層中之介電體層形成中所使用之光阻劑材料及保護膜等各種用途,但並不特別限制於該用途,尤其適合用於上述用途中之顯示器顯示裝置中。
本發明之顯示器顯示裝置除了具有本發明之硬化物(尤其是BCS)以外是與先前公知之顯示裝置相同之構成,BCS較佳為設於單元與單元之間。
於使用本發明之聚合性組合物作為有機EL之黑色間隔壁之情形時,自圖案形狀之垂直化、顯影密接性之提高、耐熱性之提高考慮,較佳為使用重量平均分子量為5000以上之鹼性顯影性化合物,進而較佳為使用重量平均分子量7000~15000之鹼性顯影性化合物。進而,於鹼性顯影性化合物為具有藉由酯化反應而獲得之結構之不飽和化合物之情形時尤佳,上述酯化反應係具有於下述通式(IV)所表示之環氧化合物上加成有不飽和一元酸之結構的環氧加成化合物與多元酸酐之酯化反應。
關於使用本發明之聚合性組合物、BM用感光性組合物及BCS用感光性組合物而製造硬化物之方法,於以下加以詳細說明。
本發明之聚合性組合物、BM用感光性組合物及BCS用感光性組合物可藉由旋轉塗佈機、輥式塗佈機、棒式塗佈機、模嘴塗佈機、簾幕式塗佈機、各種印刷、浸漬等公知之手段而應用於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上。又,於暫時賦予至膜等支持基體上之後,亦可轉印於其他支持基體上,其應用方法並無限制。
又,作為使本發明之聚合性組合物及BCS用感光性組合物硬化時所使用之能量線之光源,可利用由超高壓水銀燈、高壓水銀燈、中壓水銀燈、低壓水銀燈、水銀蒸氣弧燈、氙弧燈、碳弧燈、金屬鹵素燈、螢光燈、鎢絲燈、準分子燈、殺菌燈、發光二極體、CRT光源等而獲得之具有2000埃至7000埃之波長的電磁波能量或電子束、X射線、放射線等高能量線,較佳為列舉發出波長為300~450 nm之光的超高壓水銀燈、水銀蒸氣弧燈、碳弧燈、氙弧燈等。
進而,藉由於曝光光源中使用雷射光,並不使用遮罩地由電腦等之數位資訊形成直接圖像之雷射直接刻寫法不僅可實現生產性之提高,亦可實現解像性或位置精度等之提高,因此有用,該雷射光可適宜使用340~430 nm之波長的光,亦可使用準分子雷射、氮雷射、氬離子雷射、氦-鎘雷射、氦氖雷射、氪離子雷射、各種半導體雷射及YAG雷射等發出自可見至紅外區域之光者。於使用該等雷射之情形時,可加入吸收自可見至紅外之該區域的增感色素。
本發明之硬化物作為BCS特別有用。BCS可藉由如下步驟而較佳地形成:(1)於基板上形成本發明之BCS用感光性組合物之塗膜之步驟、(2)經由具有特定圖案形狀之遮罩對該塗膜照射放射線之步驟、(3)曝光後烘烤步驟、(4)對曝光後之該被膜進行顯影之步驟、(5)對顯影後之該被膜進行加熱之步驟。 作為上述遮罩,亦可使用半色調遮罩或灰度遮罩等多階遮罩。 [實施例]
以下,列舉實施例及比較例對本發明加以更詳細之說明,但本發明並不限定於該等實施例等。
[製造例1]內醯胺黑分散液B-1之製備 將有機系之黑色顏料(作為內醯胺黑之Black 582;巴斯夫公司製造)、分散劑(BYK-167)及用於分散物之聚合物(後述之鹼性顯影性化合物PGMEA溶液C-2)分別以16質量份、3.2質量份及3.6質量份加以混合後,以固形物成分濃度成為25質量%之方式稱量丙二醇單甲醚乙酸酯(PGMEA)添加於該混合物中,製成混合物。 藉由攪拌器將上述混合物預混合後,以與分散物(自混合物中去除了溶劑PGMEA者)相同之重量添加直徑為0.3 mm之氧化鋯珠,於25~60℃之溫度下歷時6小時實施利用塗料振盪機之分散物處理,然後使用過濾器去除氧化鋯珠,獲得分散液。於所獲得之分散液中追加PGMEA,以分散物濃度成為20質量%之方式進行調整,藉由攪拌器使其變均勻後,獲得內醯胺黑分散液B-1。
[製造例2]苝黑分散液B-2之製備 將有機系之黑色顏料[作為苝黑之C.I.顏料黑31(Paliogen Black S 0084;巴斯夫公司製造)]、分散劑(BYK-167)及用於分散物之聚合物(後述之鹼性顯影性化合物PGMEA溶液C-2)分別以12質量份、3.6質量份及8質量份加以混合後,以固形物成分濃度成為25質量%之方式稱量丙二醇單甲醚乙酸酯(PGMEA)添加於該混合物中,製成混合物。 藉由攪拌器將上述混合物預混合後,以與分散物(自混合物中去除了溶劑PGMEA者)相同之重量添加直徑為0.3 mm之氧化鋯珠,於25~60℃之溫度下歷時6小時實施利用塗料振盪機之分散物處理,然後使用過濾器去除氧化鋯珠,獲得分散液。於所獲得之分散液中追加PGMEA,以分散物濃度成為20質量%之方式進行調整,藉由攪拌器使其變均勻後,獲得苝黑分散液B-2。
[製造例3]碳黑分散液B-3之製備 將作為碳黑之MA100 (三菱化學公司製造)20質量份、作為分散劑之BYK161 (BYK-Chemie(BYK)公司製造)12.5質量份(固形物成分濃度為40質量%)、作為溶劑之丙二醇單甲醚乙酸酯67.5質量份加以混合,藉由珠磨機進行處理而製備碳黑分散液B-3。
[製造例4]鹼性顯影性化合物PGMEA溶液C-2之製備 裝入1,1-雙[4-(2,3-環氧丙氧基)苯基]茚滿184 g、丙烯酸58 g、2,6-二-第三丁基-對甲酚0.26 g、四正丁基溴化銨0.11 g及PGMEA 105 g,於120℃下進行16小時攪拌。將反應液冷卻至室溫,加入PGMEA 160 g、聯苯四甲酸二酐59 g及四正丁基溴化銨0.24 g,於120℃下攪拌4小時。進而,加入四氫鄰苯二甲酸酐20 g,於120℃下攪拌4小時,於100℃下攪拌3小時,於80℃下攪拌4小時,於60℃下攪拌6小時,於40℃下攪拌11小時後,加入PGMEA 128 g,以PGMEA溶液之形式獲得鹼性顯影性化合物C-2 (Mw=5000、Mn=2100、酸值(固形物成分)為92.7 mgKOH/g)。鹼性顯影性化合物PGMEA溶液C-2中之鹼性顯影性化合物之含有率為45質量%。
[製造例5]鹼性顯影性化合物PGMEA溶液C-3之製造 裝入9,9-雙(4-縮水甘油氧基苯基)茀75.0 g、丙烯酸23.8 g、2,6-二-第三丁基-對甲酚0.273 g、四丁基氯化銨0.585 g、及PGMEA 65.9 g,於90℃下攪拌1小時,於100℃下攪拌1小時,於110℃下攪拌1小時及於120℃下攪拌14。冷卻至室溫而加入琥珀酸酐25.9 g、四丁基氯化銨0.427 g、及PGMEA 1.37 g,於100℃下攪拌5小時。進而加入9,9-雙(4-縮水甘油氧基苯基)茀30.0 g、2,6-二-第三丁基-對甲酚0.269 g、及PGMEA 1.50 g,於90℃下攪拌90分鐘,於120℃下攪拌4小時後,加入PGMEA 122.2 g,以PGMEA溶液之形式獲得作為目標物之鹼性顯影性化合物C-3(Mw=4190、Mn=2170、酸值(固形物成分)為52 mg・KOH/g)。鹼性顯影性化合物PGMEA溶液C-3中之鹼性顯影性化合物之含有率為45質量%。
[實施例1~14及比較例1~5]聚合性組合物之製備 依照[表1]~[表4]之組成將各成分加以混合,獲得聚合性組合物(實施例1~12及比較例1~5)。再者,表中之組成之數值表示質量份。 又,表中之各成分之符號表示下述成分。 A1-1 化合物No.A1-1 [屬於(A1)成分之聚合起始劑] A2-1 化合物No.A2-1 [屬於(A2)成分之聚合起始劑] A2-2 化合物No.A2-8 [屬於(A2)成分之聚合起始劑] A2-3 化合物No.A2-14 [屬於(A2)成分之聚合起始劑] A3-1 IRGACURE907 (並不具有羥基之α-胺基苯乙酮化合物;巴斯夫公司製造) B-1 內醯胺黑分散液B-1 B-2 苝黑分散液B-2 B-3 碳黑分散液B-3 C-1 CCR-1171H (通式(II)所表示之鹼性顯影性化合物之PGMEA溶液 固形物成分為69.5質量%;日本化藥公司製造) C-2 鹼性顯影性化合物PGMEA溶液C-2 C-3 鹼性顯影性化合物PGMEA溶液C-3 D-1 Kayarad DPHA (乙烯性不飽和化合物;日本化藥公司製造) D-2 UA-306H (胺基甲酸酯單體、PETA+HDI) E-1 γ-縮水甘油氧基丙基三甲氧基矽烷(偶合劑) E-2 Karenz PE-1 (硫醇化合物;昭和電工公司製造) G-1 PGMEA G-2 乙酸3-甲氧基丁酯 G-3 琥珀酸二甲酯
[由聚合性組合物獲得之硬化物之評價] 關於由實施例1~14及比較例1~5之聚合性組合物獲得之硬化物,依照下述順序進行彈性回覆率、遮光性(OD值)、相對介電常數、液晶污染性(VHR)及耐化學品性之評價。將結果一併記載於[表1]~[表4]中。
(彈性回覆率) 藉由旋轉塗佈(3 μm厚、300 rpm×7秒)於玻璃基板上塗佈實施例1~14之聚合性組合物及比較例1~5之比較聚合性組合物,進行乾燥後於90℃下進行100秒之預烘烤,將溶劑除去後,使用光罩而藉由高壓水銀燈進行100 mJ/cm2
曝光後,使用0.04質量%之KOH水溶液進行顯影,然後於230℃下進行30分鐘加熱,製成圖案。於所獲得之圖案之20 μm部分,使用島津公司之動態微小硬度計DUH-211,以40 mN之荷重進行負載-卸載試驗。藉由下述計算式算出彈性回覆率(%)。 彈性回覆率(%)=[(回覆距離/壓縮位移)×100] 彈性回覆率(%)為60%以上之硬化物可作為BCS而使用,彈性回覆率(%)為70%以上之硬化物可作為BCS而較佳地使用,彈性回覆率(%)為80%以上之硬化物可作為BCS而尤佳地使用。
(OD值) 於玻璃基板上旋轉塗佈實施例1~14之聚合性組合物及比較例1~5之比較聚合性組合物(300 rpm、7秒)而使其乾燥後,於90℃下進行100秒之預烘烤。於使用超高壓水銀燈作為光源而進行曝光後,於230℃下烘烤30分鐘而製成硬化物。使用麥克貝思透射密度計而測定所獲得之膜之OD值,該OD值除以後烘烤後之膜厚,算出單位膜厚之OD值。 單位膜厚之OD值為1.0以上之硬化物之遮光性高,因此可作為BCS而使用,單位膜厚之OD值為1.5以上之硬化物可作為BCS而較佳地使用,單位膜厚之OD值為2.0以上之硬化物可作為BCS而尤佳地使用。單位膜厚之OD值未達1.0之硬化物無法作為BCS而使用。
(相對介電常數) 於玻璃基板上旋轉塗佈實施例1~14之聚合性組合物及比較例1~5之比較聚合性組合物(3 μm厚、300 rpm×7秒)而使其乾燥後,於90℃下進行100秒之預烘烤,並不使用遮罩而藉由高壓水銀燈進行100 mJ/cm2
之曝光後,進行230℃×180分鐘之加熱,製成上述評價樣品。 (評價法) 關於上述評價樣品,使用LCR測定計、安捷倫公司之4284A,施加AC1V、1 kHz進行測定。 相對介電常數未達5.0之硬化物可作為BCS而使用,相對介電常數為4.5以下之硬化物可作為BCS而較佳地使用,相對介電常數為4.0以下之硬化物可作為BCS而尤佳地使用。相對介電常數為5.0以上之硬化物無法作為BCS而使用。
(VHR) 使用旋轉塗佈機將實施例1~14中所獲得之聚合性組合物及比較例1~5中所獲得之比較聚合性組合物塗佈於玻璃基板(100mm×100mm)上,於90℃下進行100秒之預烘烤,形成膜厚為3.0 μm之塗膜。其次,使用鏡面投影對準曝光器(產品名:TME-150RTO、拓普康股份有限公司製造),並未介隔遮罩而以200mJ/cm2
之照射量對塗膜照射紫外線。其後,於230℃下進行30分鐘之後烘烤。 將後烘烤後之塗膜之1質量份與40質量份之ADEKA公司製造之液晶「RS-182」加以混合,於120℃下保存1小時。將其取出於室溫下靜置後,採取上清液。測定所採取之液晶組合物之VHR(電壓保持率)。詳細之評價方法如下所述。將液晶組合物注入至液晶評價用TN單元(單元厚度為5 μm、電極面積為8 mm×8 mm、配向膜為JALS2096)中,使用VHR-1A(東陽技術公司製造)測定VHR。(測定條件:脈波電壓寬度為60 μs、幀週期為16.7 ms、波高為±5 V、測定溫度為60℃) VHR為90%以上之硬化物之液晶污染性低,可作為BCS而使用,VHR為95%以上之硬化物可作為BCS而較佳地使用,VHR為98%以上之硬化物可作為BCS而尤佳地使用。 VHR未達90%之硬化物無法作為BCS使用。
<NMP耐化學品性> N-甲基吡咯啶酮(NMP)溶出試驗按照以下順序進行。 首先,藉由旋轉塗佈機將所製備之實施例1~14中所獲得之聚合性組合物及比較例1~5中所獲得之比較聚合性組合物以最終膜厚成為3 μm之方式塗佈於玻璃基板上,進行1分鐘減壓乾燥後,藉由加熱板以90℃進行120秒之乾燥。藉由高壓水銀燈進行50 mJ/cm2
之曝光後,經過顯影步驟後,於烘箱中以230℃進行40分鐘之加熱而獲得抗蝕劑塗佈基板。自所製作之抗蝕劑塗佈基板切出2枚測定用基板(25 mm×35 mm見方),將其浸漬於放入有8 mL N-甲基吡咯啶酮(NMP)之10 mL用小瓶中。繼而,於將該放入有測定用基板之小瓶於90℃之潔淨烘箱中靜置60分鐘之狀態下實施NMP溶出試驗。於靜置40分鐘後自熱浴中取出小瓶,藉由分光光度計(島津製作所公司製造之「UV-3100PC」),於300~800 nm之波長範圍每隔1 nm地測定該NMP溶出溶液之吸光度。光源使用鹵素燈及氘燈(切換波長為360 nm),檢測器使用光電倍增器,將狹縫寬度2 nm作為測定條件。又,將試樣溶液放入至1 cm見方之石英槽中進行測定。吸光度係於分光法中表示使光通過某物體時光強度衰減何種程度之無因次量,藉由以下式進行定義。
A(吸光度)=-log10
(I/I0
) (I:透射光強度、I0
:入射光強度)
又,上述之入射光強度及透射光強度可視為自相同光源對試樣溶液與單獨之NMP分別射入光時,透過單獨之NMP之光強度I0
與透過試樣溶液之光強度I。因此,上式之(I/I0
)表示透光率,吸光度A係指以對數表示透過率之倒數之值。吸光度A係算出試樣溶液中所含有之物質之濃度等時所使用之記法。於吸光度A=0之情形時,表示完全不吸收光之狀態(透過率為100%),於吸光度A=∞之情形時,表示完全不透過光之狀態(透過率為0%)。亦即,吸光度越強,越表示抗蝕劑塗膜成分較多地溶出至NMP中,耐NMP性差。算出所測定之吸光度之光譜面積(nm),以下述之基準進行評價。 NMP耐化學品性評價基準:根據NMP溶出溶液之吸收光譜之面積值而判定(波長為300~800 nm) ○:未達20(nm) △:20(nm)以上、未達60(nm) ×:60(nm)以上 NMP耐化學品性評價為〇者可作為BCS而尤佳地使用,NMP耐化學品性評價為△者可作為BCS而使用,NMP耐化學品性評價為×者無法作為BCS而使用。 作為本評價基準之吸光度之光譜面積可藉由各波長之吸光度之和而表示,表示所溶出之抗蝕劑成分之總和。
根據[表1]~[表4]可知:由本發明之聚合性組合物而獲得之硬化物以較高水準滿足遮光性(OD值)、相對介電常數、低液晶污染性(VHR)、耐化學品性,且彈性回覆率優異,因此可用作BCS。 [產業上之可利用性]
由本發明之聚合性組合物、BM用感光性組合物或BCS用感光性組合物獲得之硬化物係彈性回覆、遮光性、耐化學品性優異,介電常數低,電特性良好之硬化物,特別適於BCS。該硬化物於顯示器顯示裝置等中特別有用。
Claims (6)
- 一種黑柱間隔物用感光性組合物,其係含有聚合起始劑(A)、著色劑(B)、鹼性顯影性化合物(C)及除該鹼性顯影性化合物(C)以外之乙烯性不飽和化合物(D)者,上述聚合起始劑(A)含有具有羥基之α-胺基苯乙酮化合物(A1)及具有下述通式(I)所表示之基之肟酯化合物(A2),
- 如請求項1之黑柱間隔物用感光性組合物,其中著色劑(B)係黑色顏 料。
- 如請求項1之黑柱間隔物用感光性組合物,其中鹼性顯影性化合物(C)係下述通式(II)所表示之鹼性顯影性化合物;
- 一種硬化物之製造方法,其藉由對如請求項1至3中任一項之黑柱間隔物用感光性組合物進行光照射或加熱而製造硬化物。
- 一種硬化物,其係如請求項1至3中任一項之黑柱間隔物用感光性組合物之硬化物。
- 一種顯示器顯示裝置,其含有如請求項5之硬化物。
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