TWI737705B - 組合物及新穎化合物 - Google Patents
組合物及新穎化合物 Download PDFInfo
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- TWI737705B TWI737705B TW106110456A TW106110456A TWI737705B TW I737705 B TWI737705 B TW I737705B TW 106110456 A TW106110456 A TW 106110456A TW 106110456 A TW106110456 A TW 106110456A TW I737705 B TWI737705 B TW I737705B
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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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
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- 239000011701 zinc Substances 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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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
-
- 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
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/32—Monomers containing two or more unsaturated aliphatic radicals
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- G02B5/20—Filters
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- 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
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
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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
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- G—PHYSICS
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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
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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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
Abstract
Description
本發明係關於一種含有具有特定之結構,於常溫下為惰性,藉由加熱至特定溫度使之活化而表現出功能之化合物的組合物、及新穎化合物。進而,本發明係關於一種於該組合物中添加有著色劑之著色感光性組合物及使用該著色感光性組合物之彩色濾光片。
已知有為了提昇感光性組合物之耐候性或耐熱性,而添加紫外線吸收劑或抗氧化劑從而使其穩定化之方法(專利文獻1~4)。
酚系抗氧化劑及紫外線吸收劑具有捕獲對聚合物之劣化產生較大影響的自由基之作用,因此若將該等添加至聚合系內,則一般作為所謂聚合抑制劑發揮作用,引起硬化抑制之情況成為問題,因此業界開發出潛伏性添加劑(專利文獻5)。
但是,使用先前之潛伏性添加劑之組合物由於釋氣較多,故而存在污染加熱裝置、或組合物之物性降低之問題。存在裝置被污染、或物性降低之問題。又,使用先前之潛伏性添加劑之組合物由於硬化物之耐溶劑性較低,故而亦存在引起硬化物之溶出,例如使彩色濾光片之亮度降低之問題。
專利文獻1:日本專利特開2011-048382號公報
專利文獻2:日本專利特開2014-194508號公報
專利文獻3:日本專利特開2015-108649號公報
專利文獻4:日本專利特開2015-132791號公報
專利文獻5:國際公開第2014/021023號
因此,本發明之目的在於提供一種使用於常溫下為惰性,藉由加熱至特定溫度使之活化而表現出作為抗氧化劑或紫外線吸收劑之功能的化合物之釋氣較少且硬化物之耐溶劑性較高之組合物、尤其感光性組合物。又,本發明之另一目的在於提供一種於上述組合物中添加有著色劑之著色組合物、尤其適於彩色濾光片之著色感光性組合物。
本發明者等努力進行研究,結果發現,使用具有特定保護基之化合物之組合物之釋氣較少,且其硬化物之耐溶劑性較高,又,發現,於上述組合物中添加有著色劑之著色組合物、尤其著色感光性組合物不會使光學濾光片(尤其彩色濾光片)之亮度降低,適於液晶顯示面板等圖像顯示裝置用彩色濾光片,從而達成本發明。
本發明係基於上述見解而完成者,提供一種含有具有下述通式(I)所表示之取代基之化合物之組合物。
(式中,R1及R2分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝
基、羧基、可具有取代基之碳原子數1~40之烷基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數2~20之含雜環之基或三烷基矽烷基,R1及R2所表示之烷基或芳基烷基中之亞甲基可被取代為於氧原子不相鄰之條件下將選自-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、-S-S-或-SO2-中之基組合而成之基,R'表示氫原子或碳原子數1~8之烷基,j表示1~3之數,*意指於*部分與鄰接之基進行鍵結)
以下,基於較佳之實施形態對本發明進行詳細說明。
本發明之組合物含有具有上述通式(I)所表示之取代基之化合物。
於具有上述通式(I)所表示之取代基之化合物中,下述通式(I-A)所表示者尤其耐熱性較高且釋氣較少,故而較佳。
(式中,n表示1~10之整數,X1表示n價鍵結基,R1、R2及j與上述通式(I)相同)
作為R1及R2所表示之鹵素原子,可列舉氟、氯、溴、碘,作為R1及R2所表示之碳原子數1~40之烷基,可列舉:甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、環戊基、己基、2-己基、3-己基、環己基、4-甲基環己基、庚基、2-庚基、3-庚基、異庚基、第三庚基、1-辛基、異辛基、第三辛基、金剛烷基等,作為R1及R2所表示之碳原子數6~20之芳基,可列舉:苯基、萘基、蒽基、菲基、茀基、茚基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-異丙基苯基、4-異丙基苯基、4-丁基苯基、4-異丁基苯基、4-第三丁基苯基、4-己基苯基、4-環己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、4-硬脂基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二第三丁基苯基、2,5-二第三丁基苯基、2,6-二第三丁基苯基、2,4-二第三戊基苯基、2,5-二第三戊基苯基、2,5-二第三辛基苯基、2,4-二異丙苯基苯基、4-環己基苯基、(1,1'-聯苯)-4-基、2,4,5-三甲基苯基、二茂鐵基等,作為R1及R2所表示之碳原子數7~20之芳基烷基,可列舉:苄基、1-甲基-1-苯基乙基、1-萘基甲基、9-蒽基甲基、9-茀基、3-苯基丙基、甲基-2-苯基丙烷-2-基、二苯基甲基、三苯基甲基、苯乙基、苯乙烯基、桂醯基等,作為R1及R2所表示之碳原子數2~20之含雜環之基,可列舉:將吡啶環、嘧啶環、嗒環、哌啶環、吡喃環、吡唑啉環、三環、吡咯啉環、喹啉環、異喹啉環、咪唑啉環、苯并咪唑啉環、三唑啉環、呋喃環、苯并呋喃環、噻二唑啉環、噻唑啉環、苯并噻唑啉環、噻吩環、唑啉環、苯
并唑啉環、異噻唑啉環、異唑啉環、吲哚環、吡咯啶環、哌啶酮環、二烷環等雜環與亞甲基鏈組合而成之基,作為R1及R2所表示之三烷基矽烷基,可列舉:三甲基矽烷、三乙基矽烷、乙基二甲基矽烷等經碳原子數1~6之烷基(3個烷基相同或不同)取代之矽烷基。
作為R'所表示之碳原子數1~8之烷基,可列舉R1所表示之上述烷基中之滿足特定之碳原子數者。
作為取代R1及R2所表示之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2~20之含雜環之基之取代基,可列舉:乙烯基、烯丙基、丙烯酸基、甲基丙烯酸基等乙烯性不飽和基;氟、氯、溴、碘等鹵素原子;乙醯基、2-氯乙醯基、丙醯基、辛醯基、丙烯醯基、甲基丙烯醯基、苯基羰基(苯甲醯基)、酞醯基、4-三氟甲基苯甲醯基、特戊醯基、鄰羥苯甲醯基、草醯基、硬脂醯基、甲氧基羰基、乙氧基羰基、第三丁氧基羰基、正十八烷氧基羰基、胺甲醯基等醯基;乙醯氧基、苯甲醯氧基等醯氧基;胺基、乙基胺基、二甲基胺基、二乙基胺基、丁基胺基、環戊基胺基、2-乙基己基胺基、十二烷基胺基、苯胺基、氯苯基胺基、甲苯胺基、甲氧苯胺基、N-甲基-苯胺基、二苯基胺基、萘基胺基、2-吡啶基胺基、甲氧基羰基胺基、苯氧基羰基胺基、乙醯基胺基、苯甲醯基胺基、甲醯基胺基、特戊醯基胺基、月桂醯基胺基、胺甲醯基胺基、N,N-二甲基胺基羰基胺基、N,N-二乙基胺基羰基胺基、嗎啉基羰基胺基、甲氧基羰基胺基、乙氧基羰基胺基、第三丁氧基羰基胺基、正十八烷氧基羰基胺基、N-甲基-甲氧基羰基胺基、苯氧基羰基胺基、胺磺醯基胺基、N,N-二甲基胺基磺醯基胺基、甲基磺醯基胺基、丁
基磺醯基胺基、苯基磺醯基胺基等取代胺基;磺醯胺基、磺醯基、羧基、氰基、磺基、羥基、硝基、巰基、醯亞胺基、胺甲醯基、磺醯胺基、膦酸基、磷酸基或羧基、磺基、膦酸基、磷酸基之鹽等。
作為R1及R2,氫原子、碳原子數1~8之烷基、碳原子數6~12之芳基由於釋氣較少,故而較佳。R1為具有支鏈之碳原子數1~8之烷基、尤其為第三丁基,R2為氫原子時,釋氣尤其少,故而更佳。
於上述通式(I-A)中,X1表示n價之鍵結基,具體而言,例如表示直接鍵、氫原子、氮原子、氧原子、硫原子、磷原子、下述(I-a)或(I-b)所表示之基、-CO-、-NH-CO-、-CO-NH-、-NR3-、-OR3、-SR3、-NR3R4、或具有與n相同之價數之可具有取代基之碳原子數1~120之脂肪族烴基、可具有取代基之碳原子數6~35之含芳香環烴基、或可具有取代基之碳原子數2~35之含雜環之基,R3及R4表示氫原子、可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之含芳香環烴基或可具有取代基之碳原子數2~35之含雜環之基,脂肪族烴基、含芳香環烴基及含雜環之基可被取代為選自-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-O-CO-NH-、-NR'-、-S-S-、-SO2-或氮原子中之基。
其中,於X1為氮原子、磷原子或下述(I-a)或(I-b)所表示之鍵結基之情形時,n為3,於X1為氧原子或硫原子、-CO-、-NH-CO-、-CO-NH-或-NR3-之情形時,n為2,於X1為氫原子、-OR3、-SR3或-NR3R4之情形時,n為1,X1可與苯環成為一體而形成環。
(*意指於*部分與鄰接之基進行鍵結)
上述通式(I-A)所表示之化合物具有於X1所表示之n價鍵結基鍵結有n個特定基之結構。該n個基相互相同或不同。n之值為1~10,就合成之容易性之方面而言,較佳為2~6。
於上述通式(I-A)中,作為由X1所表示,具有與n相同之價數之可具有取代基之碳原子數1~120之脂肪族烴基,作為n為一價者,例如可列舉:甲基、乙基、丙基、異丙基、環丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、環戊基、己基、2-己基、3-己基、環己基、雙環己基、1-甲基環己基、庚基、2-庚基、3-庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基、壬基、異壬基、癸基等烷基;甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基、異丁氧基、戊氧基、異戊氧基、第三戊氧基、己氧基、環己氧基、庚氧基、異庚氧基、第三庚氧基、正辛氧基、異辛氧基、第三辛氧基、2-乙基己氧基、壬氧基、癸氧基等烷氧基;甲硫基、乙硫基、丙硫基、異丙硫基、丁硫基、第二丁硫基、第三丁硫基、異丁硫基、戊硫基、異戊硫基、第三戊硫基、己硫基、環己硫基、庚硫基、異庚硫基、第三庚硫基、正辛硫基、異辛硫基、第三辛硫基、2-乙基己硫基等烷硫基;乙烯基、1-甲基乙烯基、2-甲基乙烯基、2-丙烯基、1-甲基-3-丙烯基、3-丁烯基、1-甲基-3-丁烯基、異丁烯基、3-戊烯基、4-己烯基、環己烯基、雙環己烯基、庚烯基、辛烯基、癸烯基、十五烯基、二十烯基、二十三烯基等
烯基;及該等基經後述之取代基取代之基等;作為n為二價者,可列舉:亞甲基、伸乙基、伸丙基、伸丁基、丁基二基等伸烷基;上述伸烷基之亞甲基鏈被取代為-O-、-S-、-CO-O-、-O-CO-者;乙二醇、丙二醇、丁二醇、戊二醇、己二醇等二醇之殘基;乙二硫醇、丙二硫醇、丁二硫醇、戊二硫醇、己二硫醇等二硫醇之殘基;及該等基經後述之取代基取代之基等;作為n為三價者,例如可列舉:次丙基、1,1,3-次丁基等次烷基;及該等基經後述之取代基取代之基。
作為具有與n相同之價數之可具有取代基之碳原子數6~35之含芳香環烴基,作為n為一價者,可列舉:苄基、苯乙基、二苯基甲基、三苯基甲基、苯乙烯基、桂醯基等芳基烷基;苯基、萘基等芳基;苯氧基、萘氧基等芳基氧基;苯硫基、萘硫基等芳基硫基;及該等基經後述之取代基取代之基等;作為n為二價者,可列舉:伸苯基、伸萘基等伸芳基;鄰苯二酚、雙酚等二官能苯酚之殘基;2,4,8,10-四氧雜螺[5,5]十-烷等;及該等基經後述之取代基取代之基;作為n為三價者,可列舉:苯基-1,3,5-三亞甲基等及該等基經後述之取代基取代之基。
作為具有與n相同之價數之可具有取代基之碳原子數2~35之含雜環之基,作為n為一價者,可列舉:吡啶基、嘧啶基、嗒基、哌啶基、吡喃基、吡唑基、三基、吡咯基、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、苯硫基、苯并苯硫基、噻二唑基、噻唑基、苯并噻唑基、唑基、苯并唑
基、異噻唑基、異唑基、吲哚基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二氧基咪唑啶-3-基、2,4-二氧基唑啶-3-基、苯并三唑基等;及該等基經後述之取代基取代之基等;作為n為二價者,可列舉:具有吡啶環、嘧啶環、哌啶環、哌環、三環、呋喃環、噻吩環、吲哚環等之基;及該等基經後述之取代基取代之基;作為n為三價者,可列舉:具有異三聚氰酸環之基、具有三環之基;及該等基經後述之取代基取代之基。
作為R3及R4所表示之可具有取代基之碳原子數1~35之脂肪族烴基,可列舉上述X1所表示之脂肪族烴基及該脂肪族烴基與後述之取代基之組合中滿足特定之碳原子數者,作為R3及R4所表示之可具有取代基之碳原子數6~35之含芳香環烴基及可具有取代基之碳原子數2~35之含雜環之基,可列舉:上述X1所表示之碳原子數6~35之含芳香環烴基及碳原子數2~35之含雜環之基以及將該等基與後述之取代基組合而成之基中滿足特定之碳原子數者。
作為取代基,可列舉:乙烯基、烯丙基、丙烯酸基、甲基丙烯酸基等乙烯性不飽和基;氟、氯、溴、碘等鹵素原子;乙醯基、2-氯乙醯基、丙醯基、辛醯基、丙烯醯基、甲基丙烯醯基、苯基羰基(苯甲醯基)、酞醯基、4-三氟甲基苯甲醯基、特戊醯基、鄰羥苯甲醯基、草醯基、硬脂醯基、甲氧基羰基、乙氧基羰基、第三丁氧基羰基、正十八烷氧基羰基、胺甲醯基等醯基;乙醯氧基、苯甲醯氧基等醯氧基;胺基、乙基胺基、二甲基胺基、二乙基胺基、丁基胺基、環戊基胺基、2-乙基己基胺基、十二烷基胺基、苯胺基、氯苯基胺基、甲苯胺基、甲氧苯胺基、N-甲基-苯胺
基、二苯基胺基、萘基胺基、2-吡啶基胺基、甲氧基羰基胺基、苯氧基羰基胺基、乙醯基胺基、苯甲醯基胺基、甲醯基胺基、特戊醯基胺基、月桂醯基胺基、胺甲醯基胺基、N,N-二甲基胺基羰基胺基、N,N-二乙基胺基羰基胺基、嗎啉基羰基胺基、甲氧基羰基胺基、乙氧基羰基胺基、第三丁氧基羰基胺基、正十八烷氧基羰基胺基、N-甲基-甲氧基羰基胺基、苯氧基羰基胺基、胺磺醯基胺基、N,N-二甲基胺基磺醯基胺基、甲基磺醯基胺基、丁基磺醯基胺基、苯基磺醯基胺基等取代胺基;磺醯胺基、磺醯基、羧基、氰基、磺基、羥基、硝基、巰基、醯亞胺基、胺甲醯基、磺醯胺基、膦酸基、磷酸基或羧基、磺基、膦酸基、磷酸基之鹽等,該等基可進而被取代。又,羧基及磺基可形成鹽。
於上述通式(I-A)中,n為2~6時,X1亦可分別如下述通式(1)~(5)般表示。
[化4]*-Z1-Y1-Z2-* (1)
(上述通式(1)中,Y1表示單鍵、-CR5R6-、-NR7-、二價之碳原子數1~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基、或下述(1-1)~(1-3)所表示之任一種基,該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z1及Z2分別獨立地表示直接鍵、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR6-或-PR6-,
R5、R6及R7分別獨立地表示氫原子、可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基或可具有取代基之碳原子數2~35之含雜環之基,*意指於*部分與鄰接之基進行鍵結)
(上述式中,R8表示氫原子、或者可具有取代基之苯基或碳原子數3~10之環烷基,R9表示碳原子數1~10之烷基、碳原子數1~10之烷氧基、碳原子數2~10之烯基或鹵素原子,上述烷基、烷氧基及烯基可具有取代基,f為0~5之整數,*意指於*部分與鄰接之基進行鍵結)
(*意指於*部分與鄰接之基進行鍵結)
(上述式中,R10及R11分別獨立地表示可具有取代基之碳原子數1~10之烷基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數6~20之芳基氧基、可具有取代基之碳原子數6~20之芳基硫基、可具有取代基之碳原子數6~20之芳基烯基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數2~20之含雜環之基、或鹵素原子,該烷基及芳基烷基中之亞甲基可被取代為不飽和鍵、-O-或-S-,R10可由鄰接之R10彼此形成環,p表示0~4之數,q表示0~8之數,g表示0~4之數,h表示0~4之數,g與h之數量之合計為2~4,*意指於*部分與鄰接之基進行鍵結)
(上述通式(2)中,Y11表示三價之碳原子數1~35之脂肪族烴基、碳原子數3~35之脂環族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基,Z1、Z2及Z3分別獨立地表示直接鍵、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR12-或-PR12-,R12表示氫原子、可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基或有具有取代基之碳原子數2~35之含雜環之基,脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,*意指於*部分與鄰接之基進行鍵結)
(上述通式(3)中,Y12表示碳原子、或四價之碳原子數1~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基,
該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z1~Z4分別獨立為與上述通式(2)中之Z1~Z3所表示之基相同之範圍之基,*意指於*部分與鄰接之基進行鍵結)
(上述通式(4)中,Y13表示五價之碳原子數2~35之脂肪族烴基、碳原子數6~20之芳香族烴基或碳原子數2~20之含雜環之基,該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z1~Z5分別獨立為與上述通式(2)中之Z1~Z3所表示之基相同之範圍之基,*意指於*部分與鄰接之基進行鍵結)
(上述通式(5)中,Y14表示六價之碳原子數2~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基,該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z1~Z6分別獨立為與上述通式(2)中之Z1~Z3所表示之基相同之範圍之基,*意指於*部分與鄰接之基進行鍵結)
於上述通式(1)中,作為R5、R6及R7所表示之可具有取代基之碳原子數1~35之脂肪族烴基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價脂肪族烴基、及該等基經作為表示上述通式(I-A)中之X1所表示之n價鍵結基的基之取代基而例示者取代之基中滿足特定之碳原子數者等,作為R5、R6及R7所表示之可具有取代基之碳原子數6~35之含芳香環烴基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價含芳香環烴基、及該等基經作為表示上述通式(I-A)中之X1所表示之n價鍵結基的基之取代基而例示者取代之基中滿足特定之碳原子數者等,作為R5、R6及R7所表示之可具有取代基之碳原子數2~35之含雜環之基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價之含雜環之基、及該等基經作為表示上述通式(I-A)中之X1所表示之n價鍵結的基之取代基而例示者取代之基中滿足特定之碳原子數者等。
又,於上述通式(1)中,作為Y1所表示之二價之碳原子數1~35之脂肪族烴基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示
之二價之脂肪族烴基、及該等基經作為表示上述通式(I-A)中之X1所表示之n價鍵結基的基之取代基而例示者取代之基中滿足特定之碳原子數者等,作為Y1所表示之二價之碳原子數6~35之含芳香環烴基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之二價之含芳香環烴基、及該等基經作為表示上述通式(I-A)中之X1所表示之n價鍵結基的基之取代基而例示者取代之基中滿足特定之碳原子數者等,作為Y1所表示之二價之碳原子數2~35之含雜環之基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之二價之含芳香環烴基、及該等基經作為表示上述通式(I-A)中之X1所表示之n價鍵結基的基之取代基而例示者取代之基中滿足特定之碳原子數者等。
於上述(1-1)所表示之取代基中,作為R8所表示之碳原子數3~10之環烷基,可列舉:環丙基、環丁基、環戊基、環庚基、環辛基等,作為R9所表示之碳原子數1~10之烷基,可列舉作為R1及R2所表示之碳原子數1~40之烷基而例示之基中滿足特定之碳原子數之基等,作為R9所表示之碳原子數1~10之烷氧基,可列舉:甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基、異丁氧基、戊氧基、異戊氧基、第三戊氧基、己氧基、環己氧基、庚氧基、異庚氧基、第三庚氧基、正辛氧基、異辛氧基、第三辛氧基、2-乙基己氧基、壬氧基、癸氧基等,苯基、環烷基、烷基、烷氧基及烯基之取代基與作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者相同。
於上述(1-3)所表示之基中,作為R10及R11所表示之可具有取代基之
碳原子數1~10之烷基,可列舉作為R1及R2所表示之碳原子數1~40之烷基而例示之基中滿足特定之碳原子數之基等,作為R10及R11所表示之可具有取代基之碳原子數6~20之芳基,可列舉:作為R1及R2所表示之碳原子數6~20之芳基而例示之基等,作為R10及R11所表示之可具有取代基之碳原子數6~20之芳基氧基,可列舉:苯氧基、萘氧基、2-甲基苯氧基、3-甲基苯氧基、4-甲基苯氧基、4-乙烯基苯氧基、3-異丙基苯氧基、4-異丙基苯氧基、4-丁基苯氧基、4-第三丁基苯氧基、4-己基苯氧基、4-環己基苯氧基、4-辛基苯氧基、4-(2-乙基己基)苯氧基、2,3-二甲基苯氧基、2,4-二甲基苯氧基、2,5-二甲基苯氧基、2,6-二甲基苯氧基、3,4-二甲基苯氧基、3,5-二甲基苯氧基、2,4-二第三丁基苯氧基、2,5-二第三丁基苯氧基、2,6-二第三丁基苯氧基、2,4-二第三戊基苯氧基、2,5-第三戊基苯氧基、4-環己基苯氧基、2,4,5-三甲基苯氧基、二茂鐵氧基等基,作為R10及R11所表示之可具有取代基之碳原子數6~20之芳基硫基,可列舉:將上述可具有取代基之碳原子數6~20之芳基氧基之氧原子取代為硫原子之基等,作為R10及R11所表示之可具有取代基之碳原子數8~20之芳基烯基,可列舉:將上述可具有取代基之碳原子數6~20之芳基氧基之氧原子取代為乙烯基、烯丙基、1-丙烯基、異丙烯基、2-丁烯基、1,3-丁二烯基、2-戊烯基、2-辛烯基等烯基之基等,作為R10及R11所表示之可具有取代基之碳原子數7~20之芳基烷基,可列舉:作為R1及R2所表示之碳原子數7~20之芳基烷基而例示之基等,作為R10及R11所表示之可具有取代基之碳原子數2~20之含雜環之
基,可列舉:作為R1及R2所表示之碳原子數2~20之含雜環之基而例示之基等。
作為上述通式(2)中之Y11所表示之三價之碳原子數1~35之脂肪族烴基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之三價脂肪族烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基中滿足特定之碳原子數者等,作為上述通式(2)中之Y11所表示之三價之碳原子數3~35之脂環族烴基,可列舉:由環戊基、環己基、環庚基、環辛基、環癸基、1-金剛烷基、2-金剛烷基、降金剛烷基、2-甲基金剛烷基、降基、異降基、全氫萘基、全氫蒽基、雙環[1.1.0]丁基、雙環[1.1.1]戊基、雙環[2.1.0]戊基、雙環[3.1.0]己基、雙環[2.1.1]己基、雙環[2.2.0]己基、雙環[4.1.0]庚基、雙環[3.2.0]庚基、雙環[3.1.1]庚基、雙環[2.2.1]庚基、雙環[5.1.0]辛基、雙環[4.2.0]辛基、雙環[4.1.1]辛基、雙環[3.3.0]辛基、雙環[3.2.1]辛基、雙環[2.2.2]辛基、螺[4,4]壬基、螺[4,5]癸基、十氫萘、三環癸基、四環十二烷基、雪松醇基、環十二烷基等基所衍生之三價基等,作為Y11所表示之三價之碳原子數6~35之含芳香環烴基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之三價之含芳香環烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基中滿足特定之碳原子數者等,作為Y11所表示之三價之碳原子數2~35之含雜環之基,可列舉:作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之三價含雜環之基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取
代之基中滿足特定之碳原子數者等。
又,作為R12所表示之可具有取代基之碳原子數1~35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基及可具有取代基之碳原子數2~35之含雜環之基,分別可列舉上述通式(1)中之R5、R6及R7之說明中所例示之脂肪族烴基、含芳香環烴基、含雜環之基。
於上述通式(3)中,作為Y12所表示之四價之碳原子數1~35之脂肪族烴基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之脂肪族烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之四價基中滿足特定之碳原子數者等,作為Y12所表示之四價之碳原子數6~35之含芳香環烴基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之含芳香環烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之四價之基中滿足特定之碳原子數者等,作為Y12所表示之四價之碳原子數2~35之含雜環之基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之含雜環之基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之四價基中滿足特定之碳原子數者等。
作為上述通式(4)中之Y13所表示之五價之碳原子數2~35之脂肪族烴基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之脂肪族烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之五價基中滿足特定之碳原子數
者等,作為Y14所表示之五價之碳原子數6~35之含芳香環烴基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之含芳香環烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之五價基中滿足特定之碳原子數者等,作為Y14所表示之五價之碳原子數2~35之含雜環之基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之含雜環之基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之五價基中滿足特定之碳原子數者等。
作為上述通式(5)中之Y14所表示之六價之碳原子數2~35之脂肪族烴基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之脂肪族烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之六價基中滿足特定之碳原子數者等,作為Y14所表示之六價之碳原子數6~35之含芳香環烴基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之含芳香環烴基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基而例示者取代之基所衍生之六價基中滿足特定之碳原子數者等,作為Y14所表示之六價之碳原子數2~35之含雜環之基,可列舉:由作為上述通式(I-A)中之X1所表示之n價鍵結基而例示之一價~三價之含雜環之基及該等基經作為上述通式(I-A)中之X1所表示之n價鍵結基之取代基
而例示者取代之基所衍生之六價基中滿足特定之碳原子數者等。
於上述通式(I-A)所表示之化合物中,下述通式(II-1)~(II-3)所表示者由於容易合成且耐熱性變高,故而較佳。
(式中,R82、R83及R84分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝基、羧基、或者可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2~20之含雜環之基,R1及R2與上述通式(I)相同)
(式中,r=2~6,X2於r=2時為上述通式(1)所表示之基,r=3時為上述通式(2)所表示之基,r=4時為上述通式(3)所表示之基,r=5時為上述通式(4),r=6時為上述通式(5),R92及R93分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝基、羧基、或者可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2
~20之含雜環之基,R1及R2與上述通式(I)相同)
(式中,R201、R202、R203、R204、R205、R206、R207、R208分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝基、羧基、可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2~20之含雜環之基,Y1、Z1及Z2與上述通式(1)相同)
作為上述通式(II-1)中之R82、R83及R84所表示之鹵素原子、可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基、碳原子數2~20之含雜環之基,可列舉上述通式(I)中之R1及R2之說明中所例示者。
作為上述通式(II-2)中之R92及R93所表示之鹵素原子、可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基、碳原子數2~20之含雜環之基,可列舉上述通式(I)中之R1及R2之說明中所例示者。
作為上述通式(II-3)中之R201、R202、R203、R204、R205、R206、R207、R208所表示之鹵素原子、可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基、碳原子數2~
20之含雜環之基,可列舉上述通式(I)中之R1及R2之說明中所例示者。
於上述通式(II-1)所表示之化合物中,較佳為R1為具有支鏈之碳原子數1~8之烷基、尤其為第三丁基,R2為氫原子者;R82、R83及R84分別獨立為氫原子、碳原子數1~20之烷基、碳原子數6~10之芳基、碳原子數7~12之芳基烷基、碳原子數1~10之含雜環之基,尤其R82、R83及R84中之任一個為碳原子數1~4之烷基或碳原子數1~10之含雜環之基者。
於上述通式(II-2)所表示之化合物中,較佳為R1為具有支鏈之碳原子數1~8之烷基、尤其為第三丁基,R2為氫原子者;R92及R93分別獨立為氫原子、碳原子數1~20之烷基、碳原子數6~10之芳基、碳原子數7~12之芳基烷基、碳原子數1~10之含雜環之基,尤其R92或R93為碳原子數1~4之烷基或碳原子數1~10之含雜環之基者。
於X2成為上述通式(1)之情形時,Y1較佳為硫原子、碳原子數1~20之伸烷基、碳原子數6~25之二價含芳香環烴基、碳原子數2~21之二價含雜環之基、由2,4,8,10-四氧雜螺[5,5]十一烷衍生之二價基,尤佳為碳原子數1~15之伸烷基、碳原子數6~15之二價含芳香環烴基、由2,4,8,10-四氧雜螺[5,5]十一烷衍生之二價基,Z1及Z2較佳為直接鍵、-CO-O-、-O-CO-、或可具有取代基之碳原子數1~20之脂肪族烴基、碳原子數6~10之芳香族烴基,尤佳為可具有取代基之碳原子數1~8之脂肪族烴基。
於X2成為上述通式(2)之情形時,Y11較佳為由碳原子數1~20之烷基、碳原子數6~10之芳基、碳原子數7~12之芳基烷基或碳原子數1~10
之含雜環之基衍生之三價基,尤佳為由碳原子數1~8之烷基、碳原子數6~9之芳基或碳原子數1~6之含雜環之基衍生之三價基,Z1、Z2及Z3較佳為與Z1及Z2相同,於X2成為上述通式(3)之情形時,Y12較佳為與作為較佳之Y11而於上文列舉之基對應之四價基,Z1~Z4較佳為與Z1及Z2相同,於X2成為上述通式(4)之情形時,Y13較佳為與作為較佳之Y11而於上文列舉之基對應之五價基,Z1~Z5較佳為與Z1及Z2相同,於X2成為上述通式(5)之情形時,Y14較佳為與作為較佳之Y11而於上文列舉之基對應之六價之基,Z1~Z6較佳為與Z1及Z2相同。
關於作為上述通式(I)所表示之化合物較佳者,可列舉下述[化14]~[化15]所示之化合物,但並不限制於該等化合物。
具有上述通式(I)所表示之取代基之化合物之製造方法並無特別限定,例如可使藉由日本專利特開昭57-111375號、日本專利特開平3-
173843號、日本專利特開平6-128195號、日本專利特開平7-206771號、日本專利特開平7-252191號、日本專利特表2004-501128號之各公報所記載之方法而製造之酚系化合物與1-氯-3-甲基-2-丁烯進行反應而獲得。
具有上述通式(I)所表示之取代基之化合物可於各種組合物中用作潛伏性添加劑。
上述所謂潛伏性添加劑係指於常溫、或150℃以下、例如150℃以下之預烘烤步驟中為惰性,藉由於100~250℃下加熱、或於酸/鹼觸媒存在下於80~200℃下加熱,保護基脫離而變得活性者。
具有上述通式(I)所表示之取代基之化合物除了可作為潛伏性抗氧化劑或潛伏性紫外線吸收劑而用於感光性組合物、光硬化性組合物、熱硬化性組合物或聚合性組合物以外,亦可作為潛伏性顯色劑而用於感熱材料。本發明之組合物可製成除含有具有上述通式(I)所表示之取代基之化合物之方面以外,與先前相同之感光性組合物、光硬化性組合物、熱硬化性組合物、聚合性組合物等。
於本發明之組合物中,作為潛伏性添加劑之具有上述通式(I)所表示之取代基之化合物之含量於本發明之組合物之固形物成分中較佳為0.001~20質量%,更佳為0.005~5質量%。
本發明之組合物可製成含有具有上述通式(I)所表示之取代基之化合物作為潛伏性抗氧化劑,進而含有具有酸值之具有乙烯性不飽和鍵之聚合性化合物及光自由基聚合起始劑的感光性組合物(以下亦稱為本發明之感光性組合物)。
作為該具有酸值之具有乙烯性不飽和鍵之聚合性化合物,可列舉:(甲基)丙烯酸、α-氯丙烯酸、伊康酸、順丁烯二酸、甲基順丁烯二酸、反
丁烯二酸、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、甲基反丁烯二酸、琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙基]酯、ω-羧基聚己內酯單(甲基)丙烯酸酯等於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-順丁烯二酸酯、(甲基)丙烯酸羥基丙酯-順丁烯二酸酯、二環戊二烯-順丁烯二酸酯或具有1個羧基與2個以上之(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等不飽和多元酸;苯酚及/或甲酚酚醛清漆環氧樹脂、具有聯苯骨架、萘骨架之酚醛清漆環氧樹脂、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、具有多官能環氧基之聚苯甲烷型環氧樹脂、下述通式(III)所表示之環氧化合物等使不飽和一元酸作用於環氧樹脂之環氧基之樹脂、使不飽和一元酸作用於環氧樹脂之環氧基且進而使多元酸酐作用於環氧樹脂之環氧基而獲得之樹脂、季戊四醇三丙烯酸酯、二季戊四醇五丙烯酸酯等含羥基之多官能丙烯酸酯與琥珀酸酐、鄰苯二甲酸酐、四氫鄰苯二甲酸酐等二元酸酐之反應物即具有酸值之多官能丙烯酸酯等。
(式中,X41表示直接鍵、可具有取代基之碳原子數1~4之伸烷基、可具有取代基之碳原子數3~20之脂環式烴基、-O-、-S-、-SO2-、-SS-、-SO-、-CO-、-OCO-或上述(1-1)~(1-3)所表示之取代基,
R41、R42、R43及R44分別獨立地表示氫原子、可具有取代基之碳原子數1~5之烷基、可具有取代基之碳原子數1~8之烷氧基、可具有取代基之碳原子數2~5之烯基或鹵素原子,m為0~10之整數)
該等具有酸值之具有乙烯性不飽和鍵之聚合性化合物可單獨使用或混合2種以上而使用,又,可與不具有酸值之具有乙烯性不飽和鍵之聚合性化合物組合而使用。於混合2種以上而使用之情形時,亦可使其等預先進行共聚而以共聚物之形式使用。
於本發明之感光性組合物中,具有酸值之具有乙烯性不飽和鍵之聚合性化合物之含量於本發明之組合物之固形物成分中較佳為20~80質量%,進而較佳為固形物成分中之30~70質量%。
作為上述不具有酸值之具有乙烯性不飽和鍵之聚合性化合物,例如可列舉:(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、下述化合物No.A1~No.A4、(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、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(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、三環癸烷二羥甲基二(甲基)丙烯酸酯、三[(甲基)丙烯醯基乙基]異氰尿酸酯、聚酯(甲基)丙烯酸酯低聚物等不飽和一元酸及多元酸或多酚之酯;(甲基)丙烯酸鋅、(甲基)丙烯酸鎂等不飽和多元酸之金屬鹽;順丁烯二酸酐、伊康酸酐、甲基順丁烯二酸酐、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-(2,5-二氧代四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-順丁烯二酸酐加成物、十二烯基琥珀酸酐、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元胺之醯胺;丙烯醛等不飽和醛;(甲基)丙烯腈、α-氯丙烯腈、偏氰二乙烯、氰化烯丙基等不飽和腈;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;乙烯基甲醚、乙烯基乙醚、正丁基乙烯醚、異丁基乙烯醚、烯丙基縮水甘油醚等乙烯醚;順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-環己基順丁烯二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、聚矽氧烷等於聚合物分子鏈之末端具有單(甲基)丙烯醯基之巨單體類;(甲基)丙烯腈、伸乙基、伸丙基、伸丁基、氯乙烯、乙酸乙烯酯等其他乙烯基化合物、及聚甲基丙烯酸甲酯巨單體、聚苯乙烯巨單體等巨單體類、三環癸烷骨架之單甲基丙烯酸酯、N-苯基順丁烯二醯亞胺、甲基丙烯醯氧基甲基-3-乙基氧雜環丁烷等與(甲基)丙烯酸之共聚物及使該等與如昭和電工股份有限公司製造之Karenz MOI、AOI之具有不飽和鍵之異氰酸酯化合物進行反應而得之(甲基)丙烯酸之共聚物、或氯乙烯、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、乙烯基唑啉、乙烯基咔唑、乙烯基吡咯啶酮、乙烯基吡啶、含羥基之乙烯基單體及多異氰酸酯化合物之乙烯基胺基甲酸酯化合物、含羥基之乙烯基單體及聚環氧化合物之乙烯基環氧化合物、季戊四醇三丙烯酸酯、二季戊四醇五丙烯酸酯等含羥基之多官能丙烯酸酯與甲苯二異氰酸酯、六亞甲基二異氰酸酯等多官能異氰酸酯之反應物等。
為了進行酸值調整而改良本發明之感光性組合物之顯影性,可與上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物一起進而使用單官能或多官能環氧化合物。上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物較佳為固形物成分之酸值為5~120mgKOH/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-環氧基-4-乙烯基環己烷、氧化苯乙烯、氧化蒎烯、氧化甲基苯乙烯、環氧環己烷、環氧丙烷等。
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組成之群中之一種以上,則可獲得特性更良好之感光性組合物,故而較佳。作為該雙酚型環氧化合物,除可使用上述通式(III)所表示之環氧化合物以外,亦可使用例如氫化雙酚型環氧化合物等雙酚型環氧化合物。作為該縮水甘油醚類,可列舉: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。
此外,亦可使用苯酚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-環氧基-6-甲基環己基甲基-3,4-環氧基-6-甲基環己烷羧酸酯、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、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-嗎啉基丙酮-1、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-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、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、茴香偶醯等。
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、4-苯甲醯基-4'-甲基二苯硫醚等。
作為肟系化合物,尤其下述通式(IV)或(V)所表示之化合物就感度及耐熱性之方面而言較佳。
(式中,R51及R52分別獨立地表示氫原子、氰基、可具有取代基之碳原子數1~20之烷基、可具有取代基之碳原子數6~30之芳基、可具有取代基之碳原子數7~30之芳基烷基或可具有取代基之碳原子數2~20之含雜環之基,R53及R54分別獨立地表示鹵素原子、硝基、氰基、羥基、羧基、R55、OR56、SR57、NR58R59、COR60、SOR61、SO2R62或CONR63R64,R53及R54可相互鍵結而形成環,R55、R56、R57、R58、R59、R60、R61、R62、R63及R64分別獨立地表示可具有取代基之碳原子數1~20之烷基、可具有取代基之碳原子數6~30之芳基、可具有取代基之碳原子數7~30之芳基烷基或可具有取代基之碳原子數2~20之含雜環之基,X3表示氧原子、硫原子、硒原子、CR75R76、CO、NR77或PR78,X4表示單鍵或CO,R75~R78表示碳原子數1~20之烷基、碳原子數6~30之芳基或碳原子數7~30之芳基烷基,該烷基或芳基烷基中之亞甲基既可被取代為鹵素
原子、硝基、氰基、羥基、羧基或含雜環之基,可被取代為-O-,R53及R54可分別獨立地與鄰接之任一苯環成為一體而形成環,a表示0~4之整數,b表示0~5之整數)
(式中,R101及R102分別獨立地表示R111、OR111、COR111、SR111、CONR112R113或CN,R111、R112及R113分別獨立地表示氫原子、碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳基烷基或碳原子數2~20之含雜環之基,R111、R112及R113所表示之基之氫原子可進而經R121、OR121、COR121、SR121、NR122R123、CONR122R123、-NR122-OR123、-NCOR122-OCOR123、NR122COR121、OCOR121、COOR121、SCOR121、OCSR121、COSR121、CSOR121、羥基、硝基、CN或鹵素原子取代,R121、R122及R123分別獨立地表示氫原子、碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳基烷基或碳原子數2~20之含雜環之基,R121、R122及R123所表示之基之氫原子可進而經羥基、硝基、CN、鹵素原子、羥基或羧基取代,
R111、R112、R113、R121、R122及R123所表示之基之伸烷基部分可於氧原子不相鄰之條件下1~5次被取代為-O-、-S-、-COO-、-OCO-、-NR124-、-NR124COO-、-OCONR124-、-SCO-、-COS-、-OCS-或-CSO-,R124表示氫原子、碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳基烷基或碳原子數2~20之含雜環之基,R111、R112、R113、R121、R122、R123及R124所表示之基之烷基部分既可具有分支側鏈,亦可為環狀烷基,R103表示氫原子、碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳基烷基或碳原子數2~20之含雜環之基,R103所表示之基之烷基部分既可具有分支側鏈,亦可為環狀烷基,又,R103與R107、R103與R108、R104與R105、R105與R106及R106與R107可分別成為一體而形成環,R103所表示之基之氫原子可進而經R121、OR121、COR121、SR121、NR122R123、CONR122R123、-NR122-OR123、-NCOR122-OCOR123、NR122COR121、OCOR121、COOR121、SCOR121、OCSR121、COSR121、CSOR121、羥基、硝基、CN或鹵素原子取代,R104、R105、R106及R107分別獨立地表示R111、OR111、SR111、COR114、CONR151R116、NR112COR111、OCOR111、COOR114、SCOR111、OCSR111、COSR114、CSOR111、羥基、CN或鹵素原子,R104與R105、R105與R106及R106與R107可分別成為一體而形成環,R114、R115及R116表示氫原子或碳原子數1~20之烷基,R108表示R111、OR111、SR111、COR111、CONR112R113、NR112COR111、OCOR111、COOR111、SCOR111、OCSR111、COSR111、
CSOR111、羥基、CN或鹵素原子,z表示0或1)
作為其他光自由基聚合起始劑,可列舉:2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(環戊二烯基)-雙[2,6-二氟-3-(pyl-1-基)]鈦等。
該等光自由基聚合起始劑可對應於所需之性能調配1種或2種以上者而使用。
如上之光自由基聚合起始劑之含量於本發明之感光性組合物之固形物成分中較佳為0.1~30質量%,尤佳為0.5~10質量%。若上述光自由基聚合起始劑之含量小於0.1質量%,則有利用曝光之硬化變得不充分之情形,若大於30質量%,則有於感光性組合物中析出起始劑之情形。
本發明之感光性組合物亦可進而添加著色劑而製成著色感光性組合物。該著色感光性組合物之硬化物可適宜地用作彩色濾光片。
於本發明之著色感光性組合物中,著色劑之含量於本發明之著色感光性組合物之固形物成分中較佳為0.01~50質量%,更佳為0.1~30質量%。若上述著色劑之含量小於0.01質量%,則有無法獲得所需之色度之情形,若大於50質量%,則有於著色感光性組合物中析出著色劑之情形。
作為上述著色劑,可列舉染料或顏料。
作為染料,只要為於380~1200nm具有吸收之化合物,則無特別限定,例如可列舉:偶氮化合物、蒽醌化合物、靛藍化合物、三芳基甲烷化合物、化合物、茜素化合物、吖啶化合物、茋化合物、噻唑化合物、萘酚化合物、喹啉化合物、硝基化合物、吲達胺化合物、化合物、酞菁化合物、花青化合物、二亞銨化合物、氰基乙烯基化合物、二氰基苯乙烯化合物、玫瑰紅化合物、苝化合物、多烯萘內醯胺化合物、香豆素化合
物、方酸鎓化合物、克酮鎓化合物、螺吡喃化合物、螺化合物、部花青化合物、氧喏化合物、苯乙烯基化合物、吡喃鎓化合物、繞丹寧化合物、唑啉酮化合物、鄰苯二甲醯亞胺化合物、啉化合物、萘醌化合物、氮雜蒽醌化合物、卟啉化合物、氮雜卟啉化合物、吡咯亞甲基化合物、喹吖啶酮化合物、吡咯并吡咯二酮化合物、靛青化合物、吖啶化合物、吖化合物、甲亞胺化合物、苯胺化合物、喹吖啶酮化合物、喹酞酮化合物、醌亞胺化合物、銥錯合物化合物、銪錯合物化合物等染料等,該等亦可混合複數種而使用。
作為顏料,可使用無機顏料或有機顏料,例如可使用:亞硝基化合物、硝基化合物、偶氮化合物、二偶氮化合物、化合物、喹啉化合物、蒽醌化合物、香豆素化合物、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、哌瑞酮化合物、苝化合物、吡咯并吡咯二酮化合物、硫靛化合物、二化合物、三苯基甲烷化合物、喹酞酮化合物、萘四羧酸;偶氮染料、花青染料之金屬錯合物化合物;色澱顏料;藉由爐法、煙囪法、熱流法而獲得之碳黑、或乙炔黑、科琴黑或燈黑等碳黑;利用環氧樹脂調整、被覆上述碳黑而得者、利用樹脂將上述碳黑預先於溶劑中進行分散處理,吸附20~200mg/g之樹脂而得者、將上述碳黑進行酸性或鹼性表面處理而得者、平均粒徑為8nm以上且DBP吸油量為90ml/100g以下者、由950℃下之揮發成分中之CO、CO2算出之總氧量相對於碳黑之每表面積100m2為9mg以上者;石墨、石墨化碳黑、活性碳、碳纖維、奈米碳管、螺旋碳纖維、碳奈米角、碳氣凝膠、富勒烯;苯胺黑、顏料黑7、鈦黑;疏水性樹脂、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、鉛黃、鋅黃、鐵丹(氧化鐵紅(III))、鎘紅、合成鐵黑、棕土等無機顏料或有機顏料。該等顏料可單獨或混合複數種而使用。
作為上述無機顏料或有機顏料,亦可使用市售之顏料,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、228、240、254;顏料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、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、185;顏料綠7、10、36;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;顏料紫1、19、23、27、29、30、32、37、40、50等。
於本發明之感光性組合物及著色感光性組合物中可進而添加溶劑。作為該溶劑,可列舉通常能夠視需要將上述各成分溶解或分散之溶劑,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、2-庚酮等酮類;乙醚、二烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、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、酢酸環己酯、乳酸乙酯、琥珀酸二甲酯、TEXANOL等酯系溶劑;乙二醇單甲醚、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、戊醇、二丙酮醇等醇系溶劑;乙二醇單甲基乙酸酯、乙二醇單乙基乙酸酯、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、丙酸乙氧基乙酯、1-第三丁氧基-2-丙醇、乙酸3-甲氧基丁酯、環己醇乙酸酯等醚酯系溶劑;苯、甲苯、二甲苯等BTX系溶劑;己烷、庚烷、辛烷、環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等萜烯系烴油;礦油精、Swazol # 310(Cosmo Matsuyama Oil股份有限公司)、Solvesso # 100(Exxon Chemical股份有限公司)等石蠟系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等鹵代脂肪族烴系溶劑;氯苯等鹵代芳香族烴系溶劑;卡必醇系溶劑、苯胺、三乙胺、吡啶、酢酸、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、水等,該等溶劑可作為1種或2種以上之混合溶劑而使用。於該等中,酮類、醚酯系溶劑等、尤其丙二醇-1-單甲醚-2-乙酸酯、環己酮等於感光性組合物中,使抗蝕劑與光自由基聚合起始劑之相溶性良好,故而較佳。於使用溶劑之情形時,就操作性等觀點而言,較佳為以本發明之感光性組合物或著色感光性組合物之固形物成分成為25~35質量%之量使用。
於本發明之感光性組合物及著色感光性組合物中可進而含有無機化合物。作為該無機化合物,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、二氧化矽、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、銅等。
於在本發明之感光性組合物及著色感光性組合物中使用顏料等著色劑及/或無機化合物之情形時,可添加分散劑。作為該分散劑,只要為可使著色劑、無機化合物分散、穩定化者,則無特別限制,可使用市售之分散劑、例如BYK-Chemie公司製造之BYK系列等,可適宜地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且具有氮原子之官能基為胺及/或其四級鹽且胺值為1~100mgKOH/g者。
又,於本發明之感光性組合物及著色感光性組合物中,可視需要添加對大茴香醚、對苯二酚、鄰苯二酚、第三丁基鄰苯二酚、啡噻等熱聚合抑制劑;塑化劑;接著促進劑;填充劑;消泡劑;調平劑;表面調整劑;酚系抗氧化劑、亞磷酸酯系抗氧化劑、硫醚系抗氧化劑等抗氧化劑;紫外線吸收劑;分散助劑;凝聚防止劑;觸媒;效果促進劑;交聯劑;增黏劑等慣用之添加物。
又,藉由一起使用上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物與其他有機聚合物,亦可改善本發明之感光性組合物及著色感光性組合物之硬化物之特性。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、胺基甲酸酯樹脂、聚碳酸酯聚乙烯丁醛、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,於該等中,亦較佳為聚苯乙烯、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、環氧樹脂。
於本發明之感光性組合物及著色感光性組合物中可進而併用鏈轉移劑、增感劑、界面活性劑、矽烷偶合劑、三聚氰胺化合物等。
作為上述鏈轉移劑、增感劑,一般使用含硫原子之化合物。例如可列舉: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-巰基煙鹼酸、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-巰基乙基胺、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)、季戊四醇四(3-巰基丙酸酯)等巰基化合物、將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、3-碘丙磺酸等碘化烷基化合物、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、三羥基乙基三巰基丙酸酯、下述化合物No.C1、三巰基丙酸三(2-羥基乙基)異氰尿酸酯等脂肪族多官能硫醇化合物、昭和電工公司製造之Karenz MT BD1、PE1、NR1等。
作為上述界面活性劑,可使用全氟烷基磷酸酯、全氟烷基羧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、聚矽氧系界面活性劑等界面活性劑,該等亦可組合使用。
作為上述矽烷偶合劑,例如可使用信越化學公司製造之矽烷偶合劑,其中,適宜使用KBE-9007、KBM-502、KBE-403等具有異氰酸基、甲基丙烯醯基、環氧基之矽烷偶合劑。
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)羥甲基苯胍胺、(聚)羥甲基脲等氮化合物中之活性羥甲基(CH2OH基)之全部或一部分(至少2個)經烷基醚化之化合物。此處,作為構成烷基醚之烷基,可列舉甲基、乙基或丁基,既可相互相同,亦可不同。又,未經烷基醚化之羥甲基既可於一分子內進行自縮合,亦可於兩分子間進行縮合,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、四丁氧基甲基甘脲等。於該等中,較佳為六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺等
經烷基醚化之三聚氰胺。
本發明之感光性組合物及著色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,亦可於暫時施加至膜等支持基體上後轉印至其他支持基體上,其應用方法並無限制。
又,作為使本發明之感光性組合物及著色感光性組合物硬化時所使用之活性光之光源,可使用發出波長300~450nm之光者,例如可使用超高壓水銀、水銀蒸汽弧、碳弧、氙弧等。
進而,藉由曝光光源使用雷射光,不使用遮罩而由電腦等之數位資訊直接形成圖像之雷射直接繪圖法不僅實現生產性之提高,而且亦實現解像性或位置精度等之提高,因此較為有用,作為該雷射光,適宜使用340~430nm之波長之光,亦使用氬離子雷射、氦氖雷射、YAG雷射、及半導體雷射等發出可見光至紅外線區域之光者。於使用該等雷射之情形時,添加吸收可見光至紅外線之該區域之增感色素。
本發明之感光性組合物及著色感光性組合物亦可經過使用兩種感光性組合物或著色感光性組合物分成兩次進行圖案化之雙重圖案化製程而進行圖案化。
使本發明之感光性組合物或著色感光性組合物硬化之方法包括如下步驟:藉由上述旋轉塗佈機、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、浸漬等公知手段,塗佈於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上而形成塗膜;及對該塗膜曝光上述活性光而使之硬化。
本發明之感光性組合物及著色感光性組合物(或其硬化物)可用於光硬化性塗料或清漆、光硬化性接著劑等接著劑、印刷基板、或彩色電視、PC監視器、攜帶型資訊終端、數位相機等彩色顯示之液晶顯示面板之彩色濾光片、CCD影像感測器之彩色濾光片、感光性間隔件、黑管柱間隔件、電漿顯示面板用電極材料、觸控面板、觸控感測器、粉末塗層、印刷油墨、印刷版、牙科用組合物、光造形用樹脂、凝膠塗層、電子工學用光阻劑、電鍍抗蝕劑、蝕刻阻劑、液狀及乾燥膜之兩者、阻焊劑、用以製造各種顯示用途用彩色濾光片之或於電漿顯示面板、電發光顯示裝置及LCD之製造步驟中用以形成構造之抗蝕劑、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、玻璃纖維纜線塗層、網版印刷用模板、用以藉由立體微影而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用光阻劑材料、用於印刷電路基板之逐次積層中之介電體層形成之光阻劑材料、3D安裝用光阻劑材料或保護膜等各種用途,其用途並無特別限制。
本發明之感光性組合物可藉由使其硬化而用作透明構造體。作為透明構造體,例如可列舉:被稱為感光性間隔件(PS)、管柱間隔件(CS)之柱形物;(奈米)壓印之微細圖案;大型廣告看板等之製造或液晶顯示器用彩色濾光片或配向膜之印刷等電子裝置製造所使用之噴墨接受層等。本發明之透明構造體適宜用於顯示裝置。
本發明之感光性組合物可用於透明導電膜、反射膜、偏光板、保護
膜等,可用作藉由如下方式積層之透明積層體,即,於透明基材依序塗佈所需之各層,隔著具有特定之圖案形狀之遮罩照射活性光,利用顯影液使曝光後之覆膜顯影,並對顯影後之覆膜進行加熱。作為透明積層體,例如可列舉於透明基材交替地形成有包含氧化銦與氧化鈰之複合氧化物之透明薄膜層與金屬薄膜層者等。可使用於上述各層中分別含有具有通式(I)所表示之取代基之化合物作為潛伏性添加劑的本發明之感光性組合物,亦可於任一層使用該感光性組合物。又,進而,該透明積層體適宜用於顯示裝置。
本發明之著色感光性組合物係以形成彩色濾光片之像素為目的而使用,尤其作為用以形成液晶顯示面板等圖像顯示裝置用顯示裝置用彩色濾光片之感光性組合物較為有用。
上述顯示裝置用彩色濾光片藉由如下步驟而較佳地形成:(1)於基板上形成本發明之著色感光性組合物之塗膜;(2)隔著具有特定之圖案形狀之遮罩對該塗膜照射活性光;(3)利用顯影液使曝光後之覆膜顯影;(4)對顯影後之該覆膜進行加熱。又,本發明之著色感光性組合物作為無顯影步驟之噴墨方式之著色感光性組合物亦有用。
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。
其次,對作為本發明之組合物之一例之熱硬化性組合物進行說明。
上述熱硬化性組合物係藉由加熱而硬化者,可為熱陽離子硬化性組合物、熱陰離子硬化性組合物或熱自由基硬化性組合物中之任一者,熱自由基硬化性組合物於對作為潛伏性抗氧化劑之具有通式(I)所表示之取代基之化合物進行加熱而使其活化時捕獲自由基,因此較佳。
該熱自由基硬化性組合物除含有具有通式(I)所表示之取代基之化合
物作為潛伏性抗氧化劑以外,含有自由基聚合性有機物質及熱自由基聚合起始劑作為必須成分。
作為上述自由基聚合性有機物質,作為上述自由基聚合性有機物質,為具有乙烯性不飽和鍵之聚合性化合物,具體而言,可列舉上述[0046]、[0049]所說明之化合物等。
作為上述熱自由基聚合起始劑,可列舉:2,2'-偶氮二異丁腈、2,2'-偶氮雙(甲基異丁酸酯)、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)等偶氮系起始劑;過氧化苯甲醯、過氧化二第三丁基苯甲醯、過氧化特戊酸第三丁酯、過氧化二碳酸二(4-第三丁基環己基)酯等過氧化物系起始劑、過硫酸銨、過硫酸鈉、過硫酸鉀等過硫酸鹽等。該等可使用一種或混合兩種以上而使用。
上述熱硬化性組合物可視需要溶解或分散於有機溶劑中,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、浸漬等公知手段將所獲得之塗液塗佈於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上,並進行加熱而使其硬化。
作為上述有機溶劑,並無特別限定,可使用公知慣用者,例如可較佳地使用酮、醚、醯胺、醇類等,作為具體例,可使用丙酮、甲基乙基酮、甲基正丁基酮、甲基異丁基酮、乙基異丁基酮、二乙醚、四氫呋喃、二烷、二甲基甲醯胺、二乙基甲醯胺、二甲基乙醯胺、二乙基乙醯胺、N-甲基吡咯啶酮、甲醇、乙醇、異丙醇、乙二醇、丙二醇、2-甲氧基-2-丙醇、四乙二醇二甲醚等公知之溶劑。
上述加熱硬化適宜通常於約60℃以上、較佳為100~300℃左右之溫度下進行10秒~3小時左右。
其次,對本發明之新穎化合物進行說明。
本發明之新穎化合物係由下述通式(V)、(VI)或(VII)表示。再者,下述通式(V)、(VI)及(VII)分別對應於上述通式(II-1)、(II-2)及(II-3),關於下述通式(V)、(VI)及(VII)中之可變基,可適當應用上述通式(II-1)、(II-2)及(II-3)以及(I)中之對應之可變基之說明,又,關於其他未特別說明之方面亦相同。
(式中,R31、R32及R33分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝基、羧基、或者具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2~20之含雜環之基,R30表示氫原子、碳原子數1~20之烷基、表示碳原子數6~20之芳基、碳原子數7~20之芳基烷基、碳原子數2~20之含雜環之基或三烷基矽烷基,R30所表示之烷基或芳基烷基中之亞甲基可被取代為-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-O-CO-NH-、-NR'-、-S-S-或-SO2-、或者於氧原子不相鄰之條件下將選自該等中之基組合而成之基,R'表示氫原子或碳原子數1~8之烷基)
(式中,k=2~6,X21於k=2時為下述通式(11)所表示之基,k=3時為下述通式(12)所表示之基,k=4時為下述通式(13)所表示之基,k=5時為下述通式(14),k=6時為下述通式(15),R33及R34分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝基、羧基、或者具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2~20之含雜環之基,R30與上述通式(V)相同)
[化27]*-Z11-Y20-Z12-* (11)
(上述通式(11)中,Y20表示單鍵、-CR35R36-、-NR37-、二價之碳原子數1~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基、或下述(11-1)~(11-3)所表示之任一取代基,該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z11及Z12分別獨立地表示直接鍵、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR37-或-PR37-,R35、R36及R37分別獨立地表示氫原子、可具有取代基之碳原子數1~
35之脂肪族烴基、可具有取代基之碳原子數6~35之芳香族烴基或可具有取代基之碳原子數2~35之含雜環之基,*意指於*部分與鄰接之基進行鍵結)
(上述式中,R117表示氫原子、或者可具有取代基之苯基或碳原子數3~10之環烷基,R118表示碳原子數1~10之烷基、碳原子數1~10之烷氧基、碳原子數2~10之烯基或鹵素原子,上述烷基、烷氧基及烯基可具有取代基,j為0~5之整數,*意指於*部分與鄰接之基進行鍵結)
(*意指於*部分與鄰接之基進行鍵結)
(上述式中,R119及R120分別獨立地表示可具有取代基之碳原子數1~
10之烷基、可具有取代基之碳原子數6~20之芳基、可具有取代基之碳原子數6~20之芳基氧基、可具有取代基之碳原子數6~20之芳基硫基、可具有取代基之碳原子數6~20之芳基烯基、可具有取代基之碳原子數7~20之芳基烷基、可具有取代基之碳原子數2~20之含雜環之基或鹵素原子,該烷基及芳基烷基中之亞甲基可被取代為不飽和鍵、-O-或-S-,R119可由鄰接之R119彼此形成環,s表示0~4之數,t表示0~8之數,v表示0~4之數,w表示0~4之數,v與w之數量之合計為2~4,*意指於*部分與鄰接之基進行鍵結)
(上述通式(12)中,Y21表示三價之碳原子數3~35之脂肪族烴基、碳原子數3~35之脂環族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基,Z11、Z12及Z13分別獨立地表示直接鍵、-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、-NR111-或-PR111-,R111表示氫原子、可具有取代基之碳原子數1~35之脂肪族烴基、可
具有取代基之碳原子數6~35之芳香族烴基或可具有取代基之碳原子數2~35之含雜環之基,脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,*意指於*部分與鄰接之基進行鍵結)
(上述通式(13)中,Y22表示碳原子、或四價之碳原子數1~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基,該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z11~Z14分別獨立為與上述通式(12)中之Z11~Z13所表示之基相同之範圍之基,*意指於*部分與鄰接之基進行鍵結)
(上述通式(14)中,Y23表示五價之碳原子數2~35之脂肪族烴基、碳原子數6~20之芳香族烴基或碳原子數2~20之含雜環之基,該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z11~Z15分別獨立為與上述通式(12)中之Z11~Z13所表示之基相同之範圍之基,*意指於*部分與鄰接之基進行鍵結)
(上述通式(15)中,Y24表示六價之碳原子數2~35之脂肪族烴基、碳原子數6~35之芳香族烴基或碳原子數2~35之含雜環之基,
該脂肪族烴基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-、-SO2-、-CONH-或-NHCO-、或以氧原子不相鄰之方式將該等組合而成之鍵結基,Z11~Z16分別獨立為與上述通式(12)中之Z11~Z13所表示之基相同之範圍之基,*意指於*部分與鄰接之基進行鍵結)
(式中,R61、R62、R63、R64、R65、R66、R67、R68分別獨立地表示氫原子、鹵素原子、氰基、羥基、硝基、羧基、可具有取代基之碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳基烷基或碳原子數2~20之含雜環之基,Y20、Z11及Z12與上述通式(11)相同)
於上述通式(V)及(VI)所表示之本發明之新穎化合物中,R1為具有支鏈之碳原子數1~8之烷基、尤其為第三丁基者由於釋氣較少,故而更佳。
本發明之新穎化合物之製造方法並無特別限定,例如可使藉由日本專利特開昭57-111375號、日本專利特開平3-173843號、日本專利特開平6-128195號、日本專利特開平7-206771號、日本專利特開平7-252191號、日本專利特表2004-501128號之各公報所記載之方法而製造之酚系化合物與1-氯-3-甲基-2-丁烯進行反應而獲得。
本發明之新穎化合物可用於潛伏性抗氧化劑、潛伏性紫外線吸收劑、溶解調整劑等。
以下,列舉實施例等更詳細地說明本發明,但本發明並不限定於該等實施例等。
[實施例1-1]化合物No.1之合成
於下述化合物No.1'之酚化合物0.9當量之二甲基乙醯胺溶液(理論產量之3倍量)中添加碳酸鉀(相對於1個酚基為2當量),於室溫下攪拌30分鐘。添加1-氯-3-甲基-2-丁烯(相對於1個酚基為1.25當量),加熱回流8小時。添加乙酸乙酯進行油水分離,利用無水硫酸鈉對有機層進行乾燥後,將溶劑蒸餾去除,藉由管柱層析法(己烷:乙酸乙酯=98:2)進行純化。使所獲得之固體於60℃下減壓乾燥3小時,獲得目標物。藉由1H-NMR、IR確認所獲得之固體為目標物。將結果示於[表1]~[表2]。
[實施例1-2~1-6]化合物No.2~6之合成
於實施例1-1中,使用下述化合物No.2'~6'之酚化合物代替下述化合物No.1'之酚化合物,除此以外,以與實施例1-1相同之方式合成作為目標物之化合物No.2~6。藉由1H-NMR、IR確認所獲得之固體為目標物。將結果示於[表1]~[表2]。
[實施例2-1及比較例2-1~2-3]感光性組合物No.1及比較感光性組合物No.1~No.3之製備
將SPC-1000(昭和電工公司製造,固形物成分29%之PGMEA溶液)50.0g、ARONIX M-450(東亞合成公司製造)11.6g、NCI-930(ADEKA公司製造)0.3g、PGMEA34.7g、FZ2122(Dow Corning Toray公司製造,固形物成分1%之PGMEA溶液)2.9g及[表3]所記載之化合物0.81g進行混合,攪拌至不溶物消失,獲得感光性組合物No.1及比較感光性組合物No.1~No.3。
[評價例1-1及比較評價例1-1]釋氣評價
將化合物No.1及比較化合物No.2分別稱取5mg,利用熱質量測定裝置,自室溫升溫至230℃(20℃/min.)後,測定於230℃下保持30分鐘之時間點之重量減少率,作為感光性組合物之釋氣評價。重量減少越小,表示釋氣越少。將結果示於[表4]。
由上述結果可知,本發明之化合物之釋氣較少,含有本發明之化合物之本發明之感光性組合物之釋氣變少。
[評價例2-1及比較評價例2-1~2-2]耐溶劑性評價
將上述實施例2-1中獲得之感光性組合物No.1及比較例2-1~2-2中獲得之比較感光性組合物No.1~No.2分別於410rpm×7秒之條件下塗敷至玻璃基板,利用加熱板使其乾燥(90℃×90秒)。利用超高壓水銀燈對所獲得之塗膜進行曝光(40mJ/cm2)。將曝光後之塗膜於230℃×30分鐘之條件下進行焙燒。測定所獲得之塗膜之膜厚後,於室溫下於PGMEA、環己酮、N-甲基吡咯啶酮、N-乙基吡咯啶酮中浸漬30分鐘,測定浸漬後之膜厚。浸漬前後之膜厚比(浸漬後之膜厚×100/浸漬前之膜厚)越接近100%,耐溶劑性評價為越高。
由[表5]可知,先前之含有抗氧化劑之比較感光性組合物之硬化物之耐溶劑性較低,使用本發明之化合物作為潛伏性添加劑之本發明之感光性組合物之耐溶劑性較高。
由以上結果可知,使用特定之化合物作為潛伏性添加劑之本發明之感光性組合物之釋氣較少,其硬化物之耐溶劑性優異。
根據本發明,可提供一種使用於常溫下為惰性,藉由加熱至特定溫度使之活化而表現出作為抗氧化劑或紫外線吸收劑之功能的化合物之釋氣較少且硬化物之耐溶劑性較高之組合物、尤其感光性組合物。
Claims (11)
- 一種組合物,其含有具有下述通式(I)所表示之取代基之化合物、具有酸值之具有乙烯性不飽和鍵之聚合性化合物及光自由基聚合起始劑,
- 如請求項1之組合物,其係感光性組合物。
- 一種硬化物,其係如請求項3或4之組合物之硬化物。
- 一種顯示裝置,其係於至少一部分具備使用如請求項5之硬化物所形成之透明積層體或透明構造體而成。
- 一種著色感光性組合物,其係使如請求項3或4之組合物中進而含有著色劑而成。
- 一種硬化物,其係如請求項7之著色感光性組合物之硬化物。
- 一種彩色濾光片,其係使用如請求項8之硬化物所形成。
- 一種使如請求項3或4之組合物或如請求項7之著色感光性組合物硬化之方法,其包括將如請求項3或4之組合物或如請求項7之著色感光性組合物塗佈於支持基體上而形成塗膜之步驟、及對該塗膜曝光活性光而使之硬化之步驟。
- 一種新穎化合物,其以下述通式(V)、(VI)或(VII)表示,
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JP6049521B2 (ja) | 2013-03-29 | 2016-12-21 | 富士フイルム株式会社 | 感光性樹脂組成物、硬化膜、画像形成方法、固体撮像素子、カラーフィルタおよび紫外線吸収剤 |
JP2015108649A (ja) | 2013-12-03 | 2015-06-11 | 凸版印刷株式会社 | 青色感光性組成物およびカラーフィルタ基板 |
JP2015132791A (ja) | 2013-12-13 | 2015-07-23 | 株式会社Adeka | 着色感光性組成物 |
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- 2017-03-23 WO PCT/JP2017/011886 patent/WO2017170183A1/ja active Application Filing
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JP2002356668A (ja) * | 2001-05-30 | 2002-12-13 | Fuji Photo Film Co Ltd | 紫外線吸収剤及びその製造方法、紫外線吸収剤を含有する組成物、ならびに画像形成方法 |
US20090018239A1 (en) * | 2004-01-26 | 2009-01-15 | Henkel Corporation | Underfill adhesives |
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JP6875376B2 (ja) | 2021-05-26 |
JPWO2017170183A1 (ja) | 2019-02-07 |
KR102314688B1 (ko) | 2021-10-19 |
TW201806917A (zh) | 2018-03-01 |
CN108699183A (zh) | 2018-10-23 |
KR20180132600A (ko) | 2018-12-12 |
WO2017170183A1 (ja) | 2017-10-05 |
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