TW202305505A - 著色樹脂組合物 - Google Patents
著色樹脂組合物 Download PDFInfo
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- TW202305505A TW202305505A TW111105236A TW111105236A TW202305505A TW 202305505 A TW202305505 A TW 202305505A TW 111105236 A TW111105236 A TW 111105236A TW 111105236 A TW111105236 A TW 111105236A TW 202305505 A TW202305505 A TW 202305505A
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- resin composition
- acrylate
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- 239000011342 resin composition Substances 0.000 title claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 229920005989 resin Polymers 0.000 claims abstract description 78
- 239000011347 resin Substances 0.000 claims abstract description 78
- 239000003086 colorant Substances 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 239000003505 polymerization initiator Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 5
- -1 (1-ethyl) propyl Chemical group 0.000 description 165
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 68
- 239000002904 solvent Substances 0.000 description 46
- 239000000178 monomer Substances 0.000 description 39
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 35
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 28
- 150000002430 hydrocarbons Chemical group 0.000 description 25
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- 125000003118 aryl group Chemical group 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical group CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- MKOCCXFKHVQLPW-UHFFFAOYSA-N [[1-oxo-1-(4-phenylsulfanylphenyl)butan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(CC)=NOC(=O)C1=CC=CC=C1 MKOCCXFKHVQLPW-UHFFFAOYSA-N 0.000 description 2
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- FXNJNGMYIZRQRG-UHFFFAOYSA-N tridecan-7-amine Chemical compound CCCCCCC(N)CCCCCC FXNJNGMYIZRQRG-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
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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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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- 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
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- 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
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14643—Photodiode arrays; MOS imagers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/148—Charge coupled imagers
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- Liquid Crystal (AREA)
Abstract
Description
本發明係關於一種著色樹脂組合物、彩色濾光片及顯示裝置。
液晶顯示裝置、電致發光顯示裝置及電漿顯示器等顯示裝置、或者CCD(Charge Coupled Device,電荷耦合元件)或CMOS(Complementary Metal Oxide Semiconductor,互補金氧半導體)感測器等固體攝像元件中所使用之彩色濾光片係由著色樹脂組合物製造。作為用於形成該彩色濾光片之著色樹脂組合物,使用各種著色劑,例如作為著色劑,已知有將具有碳稠環結構之式(I-2)所表示之化合物用於著色組合物之例(專利文獻1)。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本專利特開2020-79397號公報
[發明所欲解決之問題]
但是,包含上述化合物之著色樹脂組合物有可能無法充分滿足對比度。因此,本發明之目的在於提供一種可形成對比度優異之彩色濾光片之著色樹脂組合物。
[解決問題之技術手段]
本發明之主旨如下所述。
[1]一種著色樹脂組合物,其含有著色劑及鹼可溶性樹脂,且上述著色劑包含式(I)所表示之化合物。
[式(I)中,
R
1~R
9相互獨立,表示可具有取代基之碳數1~20之烴基、氫原子、鹵素原子、羥基、羧基或硝基,該烴基中所含之亞甲基可被-O-或-CO-取代;
環Z表示芳香族雜環]
[2]如[1]中記載之著色樹脂組合物,其中環Z係包含選自由氮原子、氧原子及硫原子所組成之群中之1種以上之芳香族雜環。
[3]如[1]或[2]中記載之著色樹脂組合物,其進而含有聚合性化合物及聚合起始劑。
[4]一種彩色濾光片,其係由如[1]至[3]中任一項記載之著色樹脂組合物形成。
[5]一種顯示裝置,其包含如[4]中記載之彩色濾光片。
[發明之效果]
根據本發明,能夠提供一種對比度優異之彩色濾光片。
本發明之著色樹脂組合物可用於光阻劑,包含著色劑(以下,有時稱為著色劑(A))、鹼可溶性樹脂(以下,有時稱為樹脂(B))。
本發明之著色樹脂組合物亦可包含聚合性化合物(以下,有時稱為聚合性化合物(C))及聚合起始劑(以下,有時稱為聚合起始劑(D))。
本發明之著色樹脂組合物亦可進而包含溶劑(以下,有時稱為溶劑(E))。
本發明之著色樹脂組合物亦可進而包含聚合起始助劑(以下,有時稱為聚合起始助劑(D1))。
本發明之著色樹脂組合物亦可進而包含整平劑(以下,有時稱為整平劑(F))。
再者,於本說明書中,只要未特別說明,則作為各成分例示之化合物可單獨使用或將複數種組合使用。
<著色劑(A)>
著色劑(A)包含式(I)所表示之化合物(以下,亦稱為化合物(I))。化合物(I)可使用1種或2種以上。
[式(I)中,
R
1~R
9相互獨立,表示可具有取代基之碳數1~20之烴基、氫原子、鹵素原子、羥基、羧基或硝基,該烴基中所含之亞甲基可被-O-或-CO-取代;
環Z表示芳香族雜環]
作為R
1~R
9所表示之鹵素原子,可例舉:氟原子、氯原子、溴原子及碘原子等。
作為R
1~R
9所表示之碳數1~20之烴基,可例舉脂肪族烴基及芳香族烴基。脂肪族烴基可飽和或不飽和,可為鏈狀或脂環式。
作為R
1~R
9所表示之飽和或不飽和鏈狀烴基,可例舉:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基(icosyl)等直鏈狀烷基等;異丙基、(1-乙基)丙基、異丁基、第二丁基、第三丁基、(1-乙基)丁基、(2-乙基)丁基、(1-丙基)丁基、異戊基、新戊基、第三戊基、(2-甲基)戊基、(1-乙基)戊基、(3-乙基)戊基、(1-丙基)戊基、(1-丁基)戊基、異己基、(2-甲基)己基、(5-甲基)己基、(2-乙基)己基、(1-丁基)己基、(1-戊基)己基、(2-甲基)庚基、(2-乙基)庚基、(3-乙基)庚基、(1-己基)庚基、(2-甲基)辛基、(2-乙基)辛基、(1-庚基)辛基、(2-乙基)壬基、(1-辛基)壬基等支鏈狀烷基等;乙烯基、1-丙烯基、2-丙烯基(烯丙基)、(1-甲基)乙烯基、2-丁烯基、3-丁烯基、1,3-丁二烯基、(1-(2-丙烯基))乙烯基、(1,2-二甲基)丙烯基、2-戊烯基等烯基等。飽和鏈狀烴基之碳數較佳為1~18,更佳為2~15,再佳為3~12。又,不飽和鏈狀烴基之碳數較佳為2~18,更佳為2~15,再佳為3~12。
作為R
1~R
9所表示之飽和或不飽和脂環式烴基,可例舉:環丙基、環丁基、環戊基、環己基、環庚基、環辛基等環烷基;環己烯基(例如環己-2-烯、環己-3-烯)、環庚烯基、環辛烯基等環烯基;降𦯉基、金剛烷基、雙環[2.2.2]辛基等。飽和或不飽和脂環式烴基之碳數較佳為3~15,更佳為3~12。
作為R
1~R
9所表示之芳香族烴基,可例舉:苯基、1-萘基、2-萘基、菲基、蒽基、芘基等。芳香族烴基之碳數較佳為6~15,更佳為6~12。
作為R
1~R
9所表示之烴基亦可為將上述例舉之鏈狀烴基、脂環式烴基及芳香族烴基中之2種以上組合而成之基,只要碳數之上限為20以下即可。此種基例如可為將芳香族烴基與自鏈狀烴基、脂環式烴基及芳香族烴基中選擇之至少1種基組合而成之基,於該組合而成之烴基中,亦可將鏈狀烴基組合成二價基(例如烷二基)。作為組合而成之烴基之例,可例舉:苄基、苯乙基、1-甲基-1-苯基乙基等芳烷基;苯乙烯基(苯基乙烯基)等芳烯基;苯乙炔基等芳炔基;鄰甲苯基、間甲苯基、對甲苯基、2-乙基苯基、3-乙基苯基、4-乙基苯基、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、4-乙烯基苯基、鄰異丙基苯基、間異丙基苯基、對異丙基苯基、2,3-二異丙基苯基、2,4-二異丙基苯基、2,5-二異丙基苯基、2,6-二異丙基苯基、2,4,6-三異丙基苯基、4-丁基苯基、鄰第三丁基苯基、間第三丁基苯基、對第三丁基苯基、2,6-二(第三丁基)苯基、3,5-二(第三丁基)苯基、3,6-二(第三丁基)苯基、4-第三丁基-2,6-二甲基苯基、4-戊基苯基、4-辛基苯基、4-(2,4,4-三甲基-2-戊基)苯基、2-十二烷基苯基、3-十二烷基苯基、4-十二烷基苯基等烷基芳基;2,3-二氫-4-茚基、1,2,3,5,6,7-六氫-4-第二-二環戊二烯并苯基、8-甲基-1,2,3,5,6,7-六氫-4-第二-二環戊二烯并苯基、5,6,7,8-四氫-1-萘基、5,6,7,8-四氫-2-萘基、3-甲基-5,6,7,8-四氫-2-萘基、3,5,5,8,8-五甲基-5,6,7,8-四氫-2-萘基等鍵結有烷二基之芳基;聯苯基、聯三苯基等鍵結有1個以上芳基之芳基;環己基甲基苯基、苄基苯基、(二甲基(苯基)甲基)苯基等。又,上述烴基例如可為鏈狀烴基與脂環式烴基組合而成之烴基,作為其例,可例舉:1-甲基環丙基、1-甲基環己基、2-甲基環己基、3-甲基環己基、4-甲基環己基、1,2-二甲基環己基、1,3-二甲基環己基、1,4-二甲基環己基、2,3-二甲基環己基、2,4-二甲基環己基、2,5-二甲基環己基、2,6-二甲基環己基、3,4-二甲基環己基、3,5-二甲基環己基、2,2-二甲基環己基、3,3-二甲基環己基、4,4-二甲基環己基、2,4,6-三甲基環己基、2,2,6,6-四甲基環己基、3,3,5,5-四甲基環己基、4-戊基環己基、4-辛基環己基、4-環己基環己基等鍵結有1個以上烷基之脂環式烴基;環丙基甲基、環丙基乙基、環丁基甲基、環丁基乙基、環戊基甲基、環戊基乙基、環己基甲基、2-甲基環己基甲基、環己基乙基、金剛烷基甲基等鍵結有1個以上脂環式烴基之烷基等。將鏈狀烴基、脂環式烴基及芳香族烴基中之2種以上組合而成之基之碳數較佳為6~18,更佳為6~15。
作為R
1~R
9所表示之碳數1~20之烴基可具有之取代基,例如可例舉:鹵素原子;腈基;硝基;胺基;羥基;甲氧基、乙氧基等碳數1~20之烷氧基;苯氧基、1-萘氧基、2-萘氧基等碳數6~20之芳氧基;硫醇基;甲硫基、乙硫基等碳數1~20之烷硫基;烯丙硫基;苯硫基、1-萘硫基、2-萘硫基等碳數6~20之芳硫基;磺醯基;甲基磺醯基、乙基磺醯基等碳數1~20之烷基磺醯基;苯基磺醯基、1-萘基磺醯基、2-萘基磺醯基等碳數6~20之芳基磺醯基;矽烷基;硼烷基;單甲基胺基、二甲基胺基、三甲基胺基、單乙基胺基、二乙基胺基、三乙基胺基等碳數1~20之烷基胺基;單苯基胺基、二苯基胺基、三苯基胺基等碳數6~20之芳基胺基;苄基胺基等碳數7~20之芳烷基胺基;羧基;胺甲醯基;乙醯基、丙醯基等碳數2~20之烷基羰基;苯甲醯基、1-萘基羰基、2-萘基羰基等碳數7~20之芳基羰基;甲氧基羰基、乙氧基羰基等碳數2~20之烷氧基羰基;苯氧基羰基、1-萘氧基羰基、2-萘氧基羰基等碳數7~20之芳氧基羰基等。
R
1~R
9所表示之碳數1~20之烴基中所含之亞甲基(-CH
2-)可被-O-或-CO-取代。
於R
1~R
9所表示之烴基中所含之-CH
2-被-O-、-CO-取代之情形時,其數量可為1個,亦可為2個以上。再者,於烴基中所含之-CH
2-被-O-、-CO-取代之情形時,將取代前之碳數作為該烴基之碳數。作為R
1~R
9所表示之烴基中所含之-CH
2-被-O-、-CO-取代後之基,具體而言,可例舉下述式(Y-1)~式(Y-25)所表示之基。*表示鍵結鍵。
R
1較佳為可具有取代基之碳數1~20之烴基,更佳為可具有取代基之碳數1~20之脂肪族烴基或芳香族烴基,再佳為可具有取代基之碳數1~18之脂肪族烴基,進而更佳為碳數3~16之支鏈狀烷基。
R
2~R
9較佳為氫原子。
環Z表示芳香族雜環。
環Z所表示之芳香族雜環可為單環,亦可為多環。
芳香族雜環之碳數較佳為3~20,再佳為3~18,尤佳為3~12。芳香族雜環較佳為5~12員環,更佳為5~10員環,再佳為5~9員環。
環Z較佳為包含雜原子,且包含選自由氮原子、氧原子及硫原子所組成之群中之1種以上之芳香族雜環。
環Z可包含2個以上雜原子,可分別包含2個以上氮原子、氧原子或硫原子,可包含氮原子與氧原子、氮原子與硫原子、或者氧原子與硫原子之組合,亦可包含氮原子、氧原子及硫原子之組合。
作為包含氮原子之雜環,可例舉:
吡咯、1-甲基吡咯、2,5-二甲基吡咯等吡咯、吡唑、1-甲基吡唑、2-甲基吡唑、3-甲基吡唑、4-甲基吡唑、5-甲基吡唑等吡唑、咪唑、1,2,3-三唑及1,2,4-三唑等咪唑等五員環系不飽和雜環;
吡啶、嗒𠯤、嘧啶、6-甲基嘧啶等嘧啶、吡𠯤及1,3,5-三𠯤等六員環系不飽和雜環;
吲唑、吲哚啉、異吲哚啉、吲哚、吲哚𠯤、苯并咪唑、喹啉、異喹啉、5,6,7,8-四氫(3-甲基)喹㗁啉、3-甲基喹㗁啉等喹㗁啉、喹唑啉、㖕啉、呔𠯤、㖠啶、嘌呤、喋啶、苯并吡唑、苯并哌啶等稠二環系雜環;
咔唑、吖啶及啡𠯤等稠三環系雜環等。
作為包含氧原子之雜環,可例舉:
α-乙內酯、β-丙內酯、γ-丁內酯、γ-戊內酯及δ-戊內酯等內酯系雜環;
呋喃、2,3-二甲基呋喃、2,5-二甲基呋喃等五員環系不飽和雜環;
2H-哌喃、4H-哌喃等六員環系不飽和雜環;
1-苯并呋喃等苯并呋喃、異苯并呋喃、苯并哌喃、4-甲基苯并哌喃等苯并哌喃、苯并二氧雜環戊烯、1,3-苯并二氧雜環戊烯、苯并二㗁烷、𠳭唍及異𠳭唍等稠二環系雜環;
𠮿、二苯并呋喃等稠三環系雜環等。
作為包含硫原子之雜環,可例舉:
噻吩、3-甲基噻吩、2-羧基噻吩等噻吩、2H-噻喃、4H-噻喃等噻喃、苯并四氫噻喃等苯并噻喃等五員環系不飽和雜環及六員環系不飽和雜環;
苯并噻喃、苯并四氫噻喃等苯并噻喃、苯并噻吩等稠二環系雜環等;
噻蒽、二苯并噻吩等稠三環系雜環等。
作為包含氮原子及氧原子之雜環,可例舉:
異噻唑、㗁唑、4-甲基㗁唑等㗁唑、2-甲基異㗁唑、3-甲基異㗁唑、4-甲基異㗁唑、5-甲基異㗁唑等異㗁唑等單環系不飽和雜環;
苯并㗁唑、苯并異㗁唑、苯并㗁𠯤、苯并二㗁烷、苯并咪唑啉等稠二環系雜環;
啡㗁𠯤等稠三環系雜環等。
作為包含氮原子及硫原子之雜環,可例舉:
噻唑等五員環系不飽和雜環;
苯并噻唑等稠二環系雜環;
啡噻𠯤等稠三環系雜環等。
再者,上述雜環之鍵結位可為各雜環中所含之任意2個氫原子脫離之部分。
芳香族雜環可具有取代基,作為取代基,可例舉:氟原子、氯原子、溴原子或碘原子等鹵素原子、氰基、硝基、羥基、經取代或未經取代之胺基、碳數1~8之烷氧基等。
其中,芳香族雜環較佳為包含氮原子之芳香族雜環,更佳為包含氮原子之五員環系不飽和雜環,再佳為咪唑。
式(I)所表示之化合物較佳為如表1~5所示由式(Ia-1)~式(Ia-280)表示之化合物。
於表1~5中,(D-1)~(D-16)、(G-1)~(G-24)、(Z-1)~(Z-7)與以下所示之結構相同。各基之*表示鍵結鍵。
其中,較佳為式(Ia-1)~式(Ia-48)、式(Ia-113)~式(Ia-184)所表示之化合物,更佳為式(Ia-13)所表示之化合物、式(Ia-29)所表示之化合物、式(Ia-45)所表示之化合物,再佳為式(Ia-45)所表示之化合物(下述化合物(I-4))。
式(I)所表示之化合物可藉由先前公知之方法進行製造,例如可按照Angew. Chem. Int. Ed. 1999, 38. 201-203中所記載之方法合成。
《著色劑(A1)》
本發明之著色樹脂組合物亦可包含除化合物(I)以外之染料(以下,有時稱為染料(A1-1))及/或顏料(以下,有時稱為顏料(A1-2))(以下,有時將染料(A1-1)與顏料(A1-2)合稱為著色劑(A1))作為著色劑(A)。該等可單獨使用,或者亦可將2種以上組合使用。
染料(A1-1)只要不包含化合物(I),則並無特別限定,可使用公知之染料,例如可例舉:溶劑染料、酸性染料、直接染料、媒染染料等。作為染料,例如可例舉染料索引(The Society of Dyers and Colourists出版)中被分類為染料之化合物、或者染色筆記(色染社)中所記載之公知染料。又,根據化學結構,可例舉:偶氮染料、花青染料、三苯甲烷染料、𠮿染料、蒽醌染料、萘醌染料、醌亞胺染料、次甲基染料、甲亞胺染料、方酸鎓染料、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料、硝基染料及酞菁染料等。較佳為該等中之有機溶劑可溶性染料。
作為顏料(A1-2),只要不包含化合物(I),則並無特別限定,可使用公知之顏料,例如可例舉染料索引(The Society of Dyers and Colourists出版)中被分類為顏料(pigment)之顏料。
作為被分類為顏料之顏料,例如可例舉:C.I.顏料黃1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、129、137、138、139、147、148、150、153、154、166、173、185、194、214、231等黃色顏料;
C.I.顏料橙13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色顏料;
C.I.顏料紅9、97、105、122、144、166、168、176、177、180、190、192、209、215、216、224、242、254、255、264、265、266、268、269、273等紅色顏料;
C.I.顏料藍15、15:1、15:2、15:3、15:4、15:6、16、60等藍色顏料;
C.I.顏料紫1、19、23、32、36、38等紫色顏料;
C.I.顏料綠7、36、58、59、62、63等綠色顏料;
C.I.顏料棕23、25等棕色顏料;
C.I.顏料黑1、7等黑色顏料。
作為著色劑(A1),較佳為黃色、紅色或綠色之染料及顏料。
著色劑(A1)亦可視需要實施松香處理、使用導入有酸性基或鹼性基之衍生物等進行之表面處理、利用高分子化合物等對著色劑(A1)表面進行之接枝處理、利用硫酸微粒化法等進行之微粒化處理、用於去除雜質之利用有機溶劑或水等進行之洗淨處理、利用離子交換法等去除離子性雜質之處理等。著色劑(A1)之粒徑較佳為大致均勻。
於著色劑(A)進而包含著色劑(A1)之情形時,著色劑(A)中之化合物(I)之合計量之含有率之下限相對於著色劑(A)之總量,例如為1質量%以上,較佳為2質量%以上,更佳為10質量%以上,再佳為25質量%以上,尤佳為50質量%以上。另一方面,於著色劑(A)進而包含著色劑(A1)之情形時,著色劑(A)中之化合物(I)之合計量之含有率之上限相對於著色劑(A)之總量,例如未達100質量%。
於著色樹脂組合物包含溶劑(E)之情形時,亦可於預先製備包含著色劑(A)及溶劑(E)之含著色劑液體(有時亦稱為著色組合物)之後,使用該含著色劑液體製備著色樹脂組合物。於著色劑(A)不溶解於溶劑(E)之情形時,例如於著色劑(A)包含顏料(A1-2)之情形時,含著色劑液體可藉由使著色劑(A)分散於溶劑(E)中進行混合來製備。含著色劑液體亦可包含著色樹脂組合物中所含之溶劑(E)之一部分或全部。
含著色劑液體中之固形物成分之含有率相對於含著色劑液體之總量,較佳為0.01質量%以上99.99質量%以下,更佳為0.1質量%以上99.9質量%以下,再佳為0.1質量%以上99質量%以下,進而更佳為0.5質量%以上90質量%以下,尤佳為1質量%以上50質量%以下。
著色劑(A)可藉由含有分散劑進行分散處理,而成為於溶液中均勻分散之狀態。於作為著色劑(A)將2種以上組合使用之情形時,可單獨對各者進行分散處理,亦可將複數種混合而進行分散處理。
作為分散劑,例如可例舉界面活性劑等,可為陽離子系、陰離子系、非離子系及兩性界面活性劑中之任一種。具體而言,可例舉:聚酯系、聚胺系及丙烯酸系等界面活性劑等。該等分散劑可單獨使用或者將2種以上組合使用。作為分散劑,以商品名表示時,可例舉:KP(信越化學工業(股)製造)、Flowlen(共榮社化學(股)製造)、Solsperse(註冊商標)(Zeneca(股)製造)、EFKA(註冊商標)(BASF公司製造)、Ajisper(註冊商標)(Ajinomoto Fine-Techno(股)製造)及Disperbyk(註冊商標)(BYK-Chemie(股)製造)、BYK(註冊商標)(BYK-Chemie(股)製造)等。亦可使用下述樹脂(B)作為分散劑。
於使用分散劑之情形時,該分散劑(固形物成分)之使用量相對於著色劑(A)100質量份,通常為1質量份以上10000質量份以下,較佳為5質量份以上5000質量份以下,更佳為10質量份以上1000質量份以下,再佳為15質量份以上800質量份以下。若該分散劑之使用量處於上述範圍內,則有獲得分散狀態更均勻之含著色劑液體之趨勢。
著色劑(A)之含有率相對於著色樹脂組合物之固形物成分之總量,較佳為0.1質量%以上50質量%以下,更佳為0.5質量%以上40質量%以下,再佳為1質量%以上30質量%以下。若著色劑(A)之含有率處於上述範圍內,則製成彩色濾光片時之色濃度充分,且能夠於組合物中含有所需量之樹脂(B),故而能夠形成機械強度充分之圖案,因此較佳。
此處,本說明書中之「固形物成分之總量」係指自著色樹脂組合物之總量中除去溶劑含量後之量。固形物成分之總量及各成分相對於該總量之含量例如可藉由液相層析法或氣相層析法等公知之分析方法進行測定。
<樹脂(B)>
樹脂(B)只要是與熱塑性樹脂不同,用於形成光阻劑者,則並無特別限定,為鹼可溶性樹脂,較佳為具有羧酸之鹼可溶性樹脂。
作為樹脂(B),可例舉以下之樹脂[K1]~[K6]等。
樹脂[K1]:具有來源於(a)之結構單元、及來源於(b)之結構單元之共聚物,上述(a)係選自由不飽和羧酸及不飽和羧酸酐所組成之群中之至少1種(以下,有時稱為「(a)」),上述(b)係具有碳數2~4之環狀醚結構及乙烯性不飽和鍵之單體(以下,有時稱為「(b)」);
樹脂[K2]:具有來源於(a)之結構單元、來源於(b)之結構單元、及來源於能與(a)共聚之單體(c)(但是,(a)與(b)不同)(以下,有時稱為「(c)」)之結構單元之共聚物;
樹脂[K3]:具有來源於(a)之結構單元、及來源於(c)之結構單元之共聚物;
樹脂[K4]:具有使(b)加成於來源於(a)之結構單元而得之結構單元、及來源於(c)之結構單元之共聚物;
樹脂[K5]:具有使(a)加成於來源於(b)之結構單元而得之結構單元、及來源於(c)之結構單元之共聚物;
樹脂[K6]:具有使(a)加成於來源於(b)之結構單元、進而使羧酸酐加成而得之結構單元、及來源於(c)之結構單元之共聚物。
作為單體(a),例如可例舉:丙烯酸、甲基丙烯酸、丁烯酸及鄰、間、對乙烯基苯甲酸等不飽和單羧酸;
馬來酸、富馬酸、檸康酸、中康酸、伊康酸、3-乙烯基鄰苯二甲酸、4-乙烯基鄰苯二甲酸、3,4,5,6-四氫鄰苯二甲酸、1,2,3,6-四氫鄰苯二甲酸、二甲基四氫鄰苯二甲酸及1,4-環己烯二羧酸等不飽和二羧酸;
甲基-5-降𦯉烯-2,3-二羧酸、5-羧基雙環[2.2.1]庚-2-烯、5,6-二羧基雙環[2.2.1]庚-2-烯、5-羧基-5-甲基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯及5-羧基-6-乙基雙環[2.2.1]庚-2-烯等含有羧基之雙環不飽和化合物;
除富馬酸及中康酸以外之上述不飽和二羧酸之酸酐等羧酸酐;
琥珀酸單〔2-(甲基)丙烯醯氧基乙基〕酯及鄰苯二甲酸單〔2-(甲基)丙烯醯氧基乙基〕酯等二元以上多元羧酸之不飽和單〔(甲基)丙烯醯氧基烷基〕酯類;
α-(羥基甲基)丙烯酸之類的於同一分子中具有羥基及羧基之不飽和丙烯酸酯類等。
其中,就共聚反應性之方面或所獲得之樹脂於鹼性水溶液中之溶解性之方面而言,較佳為丙烯酸、甲基丙烯酸及馬來酸酐等。
再者,於本說明書中,「(甲基)丙烯酸」表示選自由丙烯酸及甲基丙烯酸所組成之群中之至少1種。「(甲基)丙烯醯基」及「(甲基)丙烯酸酯」等表述亦具有相同含義。
單體(b)係指具有碳數2~4之環狀醚結構(例如,選自由環氧乙烷環、氧雜環丁烷環及四氫呋喃環(氧雜環戊烷環)所組成之群中之至少1種)及乙烯性不飽和鍵之聚合性化合物。單體(b)較佳為具有碳數2~4之環狀醚與(甲基)丙烯醯氧基之單體。
作為單體(b),例如可例舉:具有環氧乙烷基及乙烯性不飽和鍵之單體(以下,有時稱為「單體(b1)」)、具有氧雜環丁基及乙烯性不飽和鍵之單體(以下,有時稱為「單體(b2)」)、具有四氫呋喃基及乙烯性不飽和鍵之單體(以下,有時稱為「單體(b3)」)等。
作為單體(b1),例如可例舉:具有將不飽和脂肪族烴環氧化後之結構之單體(以下,有時稱為「單體(b1-1)」)、具有將不飽和脂環式烴環氧化後之結構之單體(以下,有時稱為「單體(b1-2)」)。
作為單體(b1-1),較佳為具有縮水甘油基及乙烯性不飽和鍵之單體。作為單體(b1-1),具體而言,可例舉:(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸β-甲基縮水甘油酯、(甲基)丙烯酸β-乙基縮水甘油酯、縮水甘油基乙烯基醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙烯基苄基縮水甘油醚、α-甲基-鄰乙烯基苄基縮水甘油醚、α-甲基-間乙烯基苄基縮水甘油醚、α-甲基-對乙烯基苄基縮水甘油醚、2,3-雙(縮水甘油氧基甲基)苯乙烯、2,4-雙(縮水甘油氧基甲基)苯乙烯、2,5-雙(縮水甘油氧基甲基)苯乙烯、2,6-雙(縮水甘油氧基甲基)苯乙烯、2,3,4-三(縮水甘油氧基甲基)苯乙烯、2,3,5-三(縮水甘油氧基甲基)苯乙烯、2,3,6-三(縮水甘油氧基甲基)苯乙烯、3,4,5-三(縮水甘油氧基甲基)苯乙烯、2,4,6-三(縮水甘油氧基甲基)苯乙烯等。
作為單體(b1-2),可例舉:一氧化乙烯基環己烯、1,2-環氧-4-乙烯基環己烷(例如Celloxide(註冊商標)2000;Daicel(股)製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如Cyclomer(註冊商標)A400;Daicel(股)製造)、(甲基)丙烯酸3,4-環氧環己基甲酯(例如Cyclomer(註冊商標)M100;Daicel(股)製造)、式(BI)所表示之化合物及式(BII)所表示之化合物等。
[式(BI)及式(BII)中,R
a及R
b相互獨立,表示氫原子、或碳數1~4之烷基,該烷基中所含之氫原子可由羥基取代;
X
a及X
b相互獨立,表示單鍵、*-R
c-、*-R
c-O-、*-R
c-S-或*-R
c-NH-;
R
c表示碳數1~6之烷二基;
*表示與O之鍵結鍵]
作為碳數1~4之烷基,例如可例舉:甲基、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基等。
作為氫原子被羥基取代之烷基,例如可例舉:羥基甲基、1-羥基乙基、2-羥基乙基、1-羥基丙基、2-羥基丙基、3-羥基丙基、1-羥基-1-甲基乙基、2-羥基-1-甲基乙基、1-羥基丁基、2-羥基丁基、3-羥基丁基、4-羥基丁基等。
作為R
a及R
b,較佳可例舉:氫原子、甲基、羥基甲基、1-羥基乙基、2-羥基乙基,更佳可例舉:氫原子、甲基。
作為烷二基,例如可例舉:亞甲基、伸乙基、丙烷-1,2-二基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基等。
作為X
a及X
b,較佳可例舉:單鍵、亞甲基、伸乙基、*-CH
2-O-(*表示與O之鍵結鍵)基、*-CH
2CH
2-O-基,更佳可例舉:單鍵、*-CH
2CH
2-O-基(*表示與O之鍵結鍵)。
作為式(BI)所表示之化合物,可例舉由式(BI-1)~式(BI-15)中之任一式所表示之化合物等。其中,較佳為式(BI-1)、式(BI-3)、式(BI-5)、式(BI-7)、式(BI-9)及式(BI-11)~式(BI-15)所表示之化合物,更佳為式(BI-1)、式(BI-7)、式(BI-9)及式(BI-15)所表示之化合物。
作為式(BII)所表示之化合物,可例舉式(BII-1)~式(BII-15)中之任一式所表示之化合物等,其中,較佳可例舉式(BII-1)、式(BII-3)、式(BII-5)、式(BII-7)、式(BII-9)及式(BII-11)~式(BII-15)所表示之化合物,更佳可例舉式(BII-1)、式(BII-7)、式(BII-9)及式(BII-15)所表示之化合物。
式(BI)所表示之化合物及式(BII)所表示之化合物可分別單獨使用,亦可併用式(BI)所表示之化合物與式(BII)所表示之化合物。併用該等化合物之情形時,式(BI)所表示之化合物及式(BII)所表示之化合物之含有比率以莫耳基準計,較佳為5:95~95:5,更佳為10:90~90:10,再佳為20:80~80:20。
作為具有氧雜環丁基及乙烯性不飽和鍵之單體(b2),更佳為具有氧雜環丁基及(甲基)丙烯醯氧基之單體。作為單體(b2),例如可例舉:3-甲基-3-(甲基)丙烯醯氧基甲基氧雜環丁烷、3-乙基-3-(甲基)丙烯醯氧基甲基氧雜環丁烷、3-甲基-3-(甲基)丙烯醯氧基乙基氧雜環丁烷、3-乙基-3-(甲基)丙烯醯氧基乙基氧雜環丁烷等。
作為具有四氫呋喃基及乙烯性不飽和鍵之單體(b3),更佳為具有四氫呋喃基及(甲基)丙烯醯氧基之單體。作為單體(b3),例如可例舉:丙烯酸四氫糠酯(例如Viscoat V#150,大阪有機化學工業(股)製造)、甲基丙烯酸四氫糠酯等。
作為單體(c),例如可例舉:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲基環己酯、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烷-8-基酯(該技術領域中,作為慣用名,被稱為「(甲基)丙烯酸雙環戊酯」;又,有時稱為「(甲基)丙烯酸三環癸酯」)、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烷-9-基酯、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烯-8-基酯(該技術領域中,作為慣用名,被稱為「(甲基)丙烯酸二環戊烯酯」)、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烯-9-基酯、(甲基)丙烯酸二環戊氧基乙酯、(甲基)丙烯酸異𦯉基酯、(甲基)丙烯酸金剛烷基酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸炔丙酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸萘酯及(甲基)丙烯酸苄酯等(甲基)丙烯酸酯;
(甲基)丙烯酸2-羥基乙酯及(甲基)丙烯酸2-羥基丙酯等含羥基之(甲基)丙烯酸酯;
馬來酸二乙酯、富馬酸二乙酯及伊康酸二乙酯等二羧酸二酯;
雙環[2.2.1]庚-2-烯、5-甲基雙環[2.2.1]庚-2-烯、5-乙基雙環[2.2.1]庚-2-烯、5-羥基雙環[2.2.1]庚-2-烯、5-羥基甲基雙環[2.2.1]庚-2-烯、5-(2'-羥基乙基)雙環[2.2.1]庚-2-烯、5-甲氧基雙環[2.2.1]庚-2-烯、5-乙氧基雙環[2.2.1]庚-2-烯、5,6-二羥基雙環[2.2.1]庚-2-烯、5,6-二(羥基甲基)雙環[2.2.1]庚-2-烯、5,6-二(2'-羥基乙基)雙環[2.2.1]庚-2-烯、5,6-二甲氧基雙環[2.2.1]庚-2-烯、5,6-二乙氧基雙環[2.2.1]庚-2-烯、5-羥基-5-甲基雙環[2.2.1]庚-2-烯、5-羥基-5-乙基雙環[2.2.1]庚-2-烯、5-羥基甲基-5-甲基雙環[2.2.1]庚-2-烯、5-第三丁氧基羰基雙環[2.2.1]庚-2-烯、5-環己氧基羰基雙環[2.2.1]庚-2-烯、5-苯氧基羰基雙環[2.2.1]庚-2-烯、5,6-雙(第三丁氧基羰基)雙環[2.2.1]庚-2-烯及5,6-雙(環己氧基羰基)雙環[2.2.1]庚-2-烯等雙環不飽和化合物;
N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-丁二醯亞胺基-3-馬來醯亞胺苯甲酸酯、N-丁二醯亞胺基-4-馬來醯亞胺丁酸酯、N-丁二醯亞胺基-6-馬來醯亞胺己酸酯、N-丁二醯亞胺基-3-馬來醯亞胺丙酸酯及N-(9-吖啶基)馬來醯亞胺等二羰基醯亞胺衍生物;
苯乙烯、鄰甲基苯乙烯、間甲基苯乙烯、對甲基苯乙烯、乙烯基甲苯及對甲氧基苯乙烯等含乙烯基之芳香族化合物;(甲基)丙烯腈等含乙烯基之腈;氯乙烯及偏二氯乙烯等鹵化烴;(甲基)丙烯醯胺等含乙烯基之醯胺;乙酸乙烯酯等酯;1,3-丁二烯、異戊二烯及2,3-二甲基-1,3-丁二烯等二烯等。
其中,就共聚反應性及耐熱性之方面而言,較佳為苯乙烯、乙烯基甲苯、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烷-8-基酯、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烷-9-基酯、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烯-8-基酯、(甲基)丙烯酸三環[5.2.1.0
2,6]癸烯-9-基酯、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、雙環[2.2.1]庚-2-烯及(甲基)丙烯酸苄酯等。
於樹脂[K1]中,來源於各個單體之結構單元之比率係於構成樹脂[K1]之所有結構單元中,
較佳為
來源於(a)之結構單元:2~60莫耳%、
來源於(b)之結構單元:40~98莫耳%,
更佳為
來源於(a)之結構單元:10~50莫耳%、
來源於(b)之結構單元:50~90莫耳%。
若樹脂[K1]之結構單元之比率處於上述範圍內,則有著色樹脂組合物之保存穩定性、形成著色圖案時之顯影性、及所獲得之濾光器之耐溶劑性優異之趨勢。
樹脂[K1]例如可參照文獻「高分子合成之實驗法」(大津隆行著化學同人出版社(股)第1版第1次印刷1972年3月1日發行)中所記載之方法及該文獻中所記載之引用文獻來製造。
具體而言,可例舉如下方法:將特定量之(a)及(b)、聚合起始劑及溶劑等放入反應容器中,例如利用氮氣置換氧氣,藉此於脫氧氛圍下一面攪拌一面進行加熱及保溫。再者,此處所使用之聚合起始劑及溶劑等並無特別限定,可使用該領域中通常使用者。例如作為聚合起始劑,可例舉偶氮化合物(2,2'-偶氮二異丁腈、2,2'-偶氮雙(2,4-二甲基戊腈)等)或有機過氧化物(過氧化苯甲醯等),作為溶劑,只要使各單體溶解即可,可例舉下文作為本發明之著色樹脂組合物之溶劑(E)而敍述之溶劑等。
再者,所獲得之共聚物可直接使用反應後之溶液,可使用濃縮或稀釋後之溶液,亦可使用藉由再沈澱等方法以固體(粉體)之形式取出者。尤其是藉由使用本發明之著色樹脂組合物中所含之溶劑作為該聚合時之溶劑,能夠將反應後之溶液直接用於本發明之著色樹脂組合物之製備,故而能夠簡化本發明之著色樹脂組合物之製造步驟。
於樹脂[K2]中,來源於各個單體之結構單元之比率係於構成樹脂[K2]之所有結構單元中,
較佳為
來源於(a)之結構單元:2~45莫耳%、
來源於(b)之結構單元:2~95莫耳%、
來源於(c)之結構單元:1~65莫耳%,
更佳為
來源於(a)之結構單元:5~40莫耳%、
來源於(b)之結構單元:5~80莫耳%、
來源於(c)之結構單元:5~60莫耳%。
若樹脂[K2]之結構單元之比率處於上述範圍內,則有著色樹脂組合物之保存穩定性、形成著色圖案時之顯影性、以及所獲得之濾光器之耐溶劑性、耐熱性及機械強度優異之趨勢。
樹脂[K2]例如可與作為樹脂[K1]之製造方法而記載之方法同樣地進行製造。
於樹脂[K3]中,來源於各個單體之結構單元之比率係於構成樹脂[K3]之所有結構單元中,
較佳為
來源於(a)之結構單元:2~60莫耳%、
來源於(c)之結構單元:40~98莫耳%,
更佳為
來源於(a)之結構單元:10~50莫耳%、
來源於(c)之結構單元:50~90莫耳%。
樹脂[K3]例如可與作為樹脂[K1]之製造方法而記載之方法同樣地進行製造。
樹脂[K4]可藉由獲得(a)與(c)之共聚物,使(b)所具有之碳數2~4之環狀醚加成於(a)所具有之羧酸及/或羧酸酐而製造。
首先,與作為樹脂[K1]之製造方法而記載之方法同樣地製造(a)與(c)之共聚物。於此情形時,來源於各個單體之結構單元之比率較佳為與樹脂[K3]中所例舉之比率相同。
接下來,使(b)所具有之碳數2~4之環狀醚與上述共聚物中之來源於(a)之羧酸及/或羧酸酐之一部分進行反應。
繼製造(a)與(c)之共聚物之後,將燒瓶內氛圍自氮氣置換成空氣,將(b)、羧酸或羧酸酐與環狀醚之反應觸媒(例如三(二甲基胺基甲基)苯酚等)及聚合抑制劑(例如對苯二酚等)等放入燒瓶內,例如於60~130℃進行反應1~10小時,藉此可製造樹脂[K4]。
(b)之使用量相對於(a)100莫耳,較佳為5~80莫耳,更佳為10~75莫耳。藉由設為該範圍,有著色樹脂組合物之保存穩定性、形成圖案時之顯影性、以及所獲得之圖案之耐溶劑性、耐熱性、機械強度與感度之平衡良好之趨勢。由於環狀醚之反應性較高,不易殘存未反應之(b),故而作為用於樹脂[K4]之(b),較佳為(b1),再佳為(b1-1)。
上述反應觸媒之使用量相對於(a)、(b)及(c)之合計量100質量份,較佳為0.001~5質量份。上述聚合抑制劑之使用量相對於(a)、(b)及(c)之合計量100質量份,較佳為0.001~5質量份。
下料方法、反應溫度及時間等反應條件可考慮製造設備或因聚合而產生之放熱量等來適當進行調整。再者,與聚合條件同樣地,可考慮製造設備或因聚合而產生之放熱量等適當調整下料方法及反應溫度。
關於樹脂[K5],作為第一階段,以與上述樹脂[K1]之製造方法相同之方式獲得(b)與(c)之共聚物。與上述相同,所獲得之共聚物可直接使用反應後之溶液,可使用濃縮或稀釋後之溶液,亦可使用藉由再沈澱等方法以固體(粉體)之形式取出者。
來源於(b)及(c)之結構單元之比率相對於構成上述共聚物之所有結構單元之合計莫耳數,分別
較佳為
來源於(b)之結構單元:5~95莫耳%、
來源於(c)之結構單元:5~95莫耳%,
更佳為
來源於(b)之結構單元:10~90莫耳%、
來源於(c)之結構單元:10~90莫耳%。
進而,可藉由在與樹脂[K4]之製造方法相同之條件下,使(a)所具有之羧酸或羧酸酐與(b)和(c)之共聚物所具有之來源於(b)之環狀醚進行反應而獲得樹脂[K5]。
與上述共聚物進行反應之(a)之使用量相對於(b)100莫耳,較佳為5~80莫耳。由於環狀醚之反應性較高,不易殘存未反應之(b),故而作為用於樹脂[K5]之(b),較佳為(b1),再佳為(b1-1)。
樹脂[K6]係進而使羧酸酐與樹脂[K5]進行反應而得之樹脂。使羧酸酐與藉由環狀醚和羧酸或羧酸酐之反應所產生之羥基進行反應。
作為羧酸酐,可例舉:馬來酸酐、檸康酸酐、伊康酸酐、3-乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二甲酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1,2,3,6-四氫鄰苯二甲酸酐、二甲基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酸酐等。羧酸酐之使用量相對於(a)之使用量1莫耳,較佳為0.5~1莫耳。
作為具體之樹脂(B),可例舉:(甲基)丙烯酸3,4-環氧環己基甲酯/(甲基)丙烯酸共聚物、丙烯酸3,4-環氧三環[5.2.1.0
2,6]癸酯/(甲基)丙烯酸共聚物等樹脂[K1];(甲基)丙烯酸縮水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸縮水甘油酯/苯乙烯/(甲基)丙烯酸共聚物、丙烯酸3,4-環氧三環[5.2.1.0
2,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺共聚物、丙烯酸3,4-環氧三環[5.2.1.0
2,6]癸酯/(甲基)丙烯酸/N-環己基馬來醯亞胺/(甲基)丙烯酸2-羥基乙酯共聚物、3-甲基-3-(甲基)丙烯醯氧基甲基氧雜環丁烷/(甲基)丙烯酸/苯乙烯共聚物等樹脂[K2];(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物、苯乙烯/(甲基)丙烯酸共聚物等樹脂[K3];使(甲基)丙烯酸縮水甘油酯加成於(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物而得之樹脂、使(甲基)丙烯酸縮水甘油酯加成於(甲基)丙烯酸三環癸酯/苯乙烯/(甲基)丙烯酸共聚物而得之樹脂、使(甲基)丙烯酸縮水甘油酯加成於(甲基)丙烯酸三環癸酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物而得之樹脂等樹脂[K4];使(甲基)丙烯酸與(甲基)丙烯酸三環癸酯/(甲基)丙烯酸縮水甘油酯之共聚物反應而得之樹脂、使(甲基)丙烯酸與(甲基)丙烯酸三環癸酯/苯乙烯/(甲基)丙烯酸縮水甘油酯之共聚物反應而得之樹脂等樹脂[K5];使(甲基)丙烯酸與(甲基)丙烯酸三環癸酯/(甲基)丙烯酸縮水甘油酯之共聚物反應所得之樹脂進一步與四氫鄰苯二甲酸酐進行應而獲得之樹脂等樹脂[K6]等。
樹脂(B)更佳為樹脂[K1]及樹脂[K2],尤佳為樹脂[K1]。
樹脂(B)之聚苯乙烯換算之重量平均分子量(Mw)較佳為1,000以上100,000以下,更佳為2,000以上50,000以下,再佳為3,000以上30,000以下。若重量平均分子量處於上述範圍內,則有未曝光部於顯影液中之溶解性較高,所獲得之圖案之殘膜率及硬度亦較高之趨勢。
樹脂(B)之分散度[重量平均分子量(Mw)/數量平均分子量(Mn)]較佳為1以上6以下,更佳為1.001以上4以下,再佳為1.01以上4以下。
樹脂(B)之酸值(固形物成分換算值)較佳為10 mg-KOH/g以上300 mg-KOH/g以下,更佳為20 mg-KOH/g以上250 mg-KOH/g以下,再佳為25 mg-KOH/g以上200 mg-KOH/g以下,進而更佳為30 mg-KOH/g以上150 mg-KOH/g以下,尤佳為60 mg-KOH/g以上135 mg-KOH/g以下。此處,酸值係作為中和1 g樹脂所需之氫氧化鉀之量(mg)而測得之值,例如可藉由使用氫氧化鉀水溶液進行滴定而求出。
樹脂(B)之含有率於著色樹脂組合物之固形物成分100質量%中,較佳為5~50質量%,更佳為10~40質量%,再佳為15~30質量%。若樹脂(B)之含量處於上述範圍內,則有未曝光部於顯影液中之溶解性較高之趨勢。
<聚合性化合物(C)>
聚合性化合物(C)係能夠利用由聚合起始劑(D)產生之活性自由基及/或酸進行聚合之化合物,例如可例舉具有聚合性之乙烯性不飽和鍵之化合物等,較佳為(甲基)丙烯酸酯化合物。
作為具有1個乙烯性不飽和鍵之聚合性化合物,例如可例舉:壬基苯基卡必醇丙烯酸酯、丙烯酸2-羥基-3-苯氧基丙酯、2-乙基己基卡必醇丙烯酸酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯啶酮等、以及上述單體(a)、單體(b)及單體(c)。
作為具有2個乙烯性不飽和鍵之聚合性化合物,例如可例舉:1,6-己二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、雙酚A之雙(丙烯醯氧基乙基)醚及3-甲基戊二醇二(甲基)丙烯酸酯等。
其中,聚合性化合物(C)較佳為具有3個以上乙烯性不飽和鍵之聚合性化合物。作為此種聚合性化合物,例如可例舉:三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(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、三季戊四醇八(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、四季戊四醇十(甲基)丙烯酸酯、四季戊四醇九(甲基)丙烯酸酯、異氰尿酸三(2-(甲基)丙烯醯氧基乙基)酯、乙二醇改性季戊四醇四(甲基)丙烯酸酯、乙二醇改性二季戊四醇六(甲基)丙烯酸酯、丙二醇改性季戊四醇四(甲基)丙烯酸酯、丙二醇改性二季戊四醇六(甲基)丙烯酸酯、己內酯改性季戊四醇四(甲基)丙烯酸酯及己內酯改性二季戊四醇六(甲基)丙烯酸酯等,較佳為二季戊四醇五(甲基)丙烯酸酯及二季戊四醇六(甲基)丙烯酸酯。
聚合性化合物(C)之重量平均分子量較佳為50以上4,000以下,更佳為70以上3,500以下,再佳為100以上3,000以下,進而更佳為150以上2,900以下,尤佳為250以上1,500以下。
聚合性化合物(C)之含有率相對於著色樹脂組合物之固形物成分之總量,例如可為1質量%以上99質量%以下,較佳為5質量%以上90質量%以下,更佳為10質量%以上80質量%以下,再佳為20質量%以上70質量%以下。
<聚合起始劑(D)>
聚合起始劑(D)只要是能夠藉由光或熱之作用產生活性自由基、酸等引發聚合之化合物,則並無特別限定,可使用公知之聚合起始劑。
作為聚合起始劑(D),可例舉:O-醯基肟化合物、苯烷酮化合物、聯咪唑化合物、三𠯤化合物及醯基氧化膦化合物等。
作為O-醯基肟化合物,例如可例舉:N-苯甲醯氧基-1-(4-苯基硫基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基硫基苯基)辛烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-(4-苯基硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-(4-苯基硫基苯基)-3-環己基丙烷-1-酮-2-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-{2-甲基-4-(3,3-二甲基-2,4-二氧雜環戊基甲氧基)苯甲醯基}-9H-咔唑-3-基]乙烷-1-亞胺、N-乙醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-亞胺及N-苯甲醯氧基-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-3-環戊基丙烷-1-酮-2-亞胺等。又,作為O-醯基肟化合物,亦可使用Irgacure(註冊商標)OXE01、OXE02(以上由BASF公司製造)及N-1919(ADEKA(股)製造)等市售品。其中,作為O-醯基肟化合物,較佳為選自由N-苯甲醯氧基-1-(4-苯基硫基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基硫基苯基)辛烷-1-酮-2-亞胺及N-苯甲醯氧基-1-(4-苯基硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺所組成之群中之至少1種,更佳為N-苯甲醯氧基-1-(4-苯基硫基苯基)辛烷-1-酮-2-亞胺。
作為苯烷酮化合物,可例舉:2-甲基-2-𠰌啉基-1-(4-甲基硫基苯基)丙烷-1-酮、2-二甲基胺基-1-(4-𠰌啉基苯基)-2-苄基丁烷-1-酮及2-(二甲基胺基)-2-[(4-甲基苯基)甲基]-1-[4-(4-𠰌啉基)苯基]丁烷-1-酮等。作為苯烷酮化合物,亦可使用Irgacure(註冊商標)369、907、379(以上由BASF公司製造)等市售品。
作為苯烷酮化合物,亦可例舉:2-羥基-2-甲基-1-苯基丙烷-1-酮、2-羥基-2-甲基-1-〔4-(2-羥基乙氧基)苯基〕丙烷-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-(4-異丙烯基苯基)丙烷-1-酮之低聚物、α,α-二乙氧基苯乙酮及苄基二甲基縮酮。
作為聯咪唑化合物,例如可例舉:2,2'-雙(2-氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(2,3-二氯苯基)-4,4',5,5'-四苯基聯咪唑(例如參照日本專利特開平6-75372號公報、日本專利特開平6-75373號公報等)、2,2'-雙(2-氯苯基)-4,4',5,5'-四(烷氧基苯基)聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(二烷氧基苯基)聯咪唑、2,2'-雙(2-氯苯基)-4,4',5,5'-四(三烷氧基苯基)聯咪唑(例如參照日本專利特公昭48-38403號公報、日本專利特開昭62-174204號公報等)及4,4',5,5'-位之苯基被烷氧羰基取代之聯咪唑化合物(例如參照日本專利特開平7-10913號公報等)等。
作為三𠯤化合物,可例舉:2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三𠯤、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三𠯤、2,4-雙(三氯甲基)-6-向日葵基-1,3,5-三𠯤、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三𠯤、2,4-雙(三氯甲基)-6-〔2-(5-甲基呋喃-2-基)乙烯基〕-1,3,5-三𠯤、2,4-雙(三氯甲基)-6-〔2-(呋喃-2-基)乙烯基〕-1,3,5-三𠯤、2,4-雙(三氯甲基)-6-〔2-(4-二乙基胺基-2-甲基苯基)乙烯基〕-1,3,5-三𠯤及2,4-雙(三氯甲基)-6-〔2-(3,4-二甲氧基苯基)乙烯基〕-1,3,5-三𠯤等。
作為醯基氧化膦化合物,可例舉2,4,6-三甲基苯甲醯基二苯基氧化膦等。亦可使用Irgacure(註冊商標)819(BASF公司製造)等市售品。
進而,作為聚合起始劑(D),可例舉:安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香異丁醚等安息香化合物;二苯甲酮、鄰苯甲醯基苯甲酸甲酯、4-苯基二苯甲酮、4-苯甲醯基-4'-甲基二苯硫醚、3,3',4,4'-四(第三丁基過氧羰基)二苯甲酮及2,4,6-三甲基二苯甲酮等二苯甲酮化合物;9,10-菲醌、2-乙基蒽醌及樟腦醌等醌化合物;10-丁基-2-氯吖啶酮、苯偶醯、苯基乙醛酸甲酯及二茂鈦化合物等。
該等與下述聚合起始助劑(D1)(尤其是胺類)組合使用較佳。
聚合起始劑(D)較佳為包含選自由苯烷酮化合物、三𠯤化合物、醯基氧化膦化合物、O-醯基肟化合物及聯咪唑化合物所組成之群中之至少一種之聚合起始劑,更佳為包含O-醯基肟化合物之聚合起始劑。
聚合起始劑(D)之含量相對於著色樹脂組合物中所含之所有樹脂(B)及聚合性化合物(C)之合計量100質量份,較佳為0.1質量份以上30質量份以下,更佳為1質量份以上20質量份以下。若聚合起始劑(D)之含量處於上述範圍內,則有感度變高而縮短曝光時間之趨勢,故而彩色濾光片之生產性提高。
<聚合起始助劑(D1)>
聚合起始助劑(D1)係用於促進藉由聚合起始劑(D)而引發聚合之聚合性化合物(C)之聚合之化合物或增感劑。於包含聚合起始助劑(D1)之情形時,通常與聚合起始劑(D)組合使用。
作為胺化合物,可例舉:三乙醇胺、甲基二乙醇胺、三異丙醇胺、4-二甲基胺基苯甲酸甲酯、4-二甲基胺基苯甲酸乙酯、4-二甲基胺基苯甲酸異戊酯、苯甲酸2-二甲基胺基乙酯、4-二甲基胺基苯甲酸2-乙基己酯、N,N-二甲基對甲苯胺、4,4'-雙(二甲基胺基)二苯甲酮(通稱米其勒酮)、4,4'-雙(二乙基胺基)二苯甲酮及4,4'-雙(乙基甲基胺基)二苯甲酮等,較佳可例舉4,4'-雙(二乙基胺基)二苯甲酮。又,作為胺化合物,亦可使用EAB-F(保土穀化學工業(股)製造)等市售品。
作為烷氧基蒽化合物,可例舉:9,10-二甲氧基蒽、2-乙基-9,10-二甲氧基蒽、9,10-二乙氧基蒽、2-乙基-9,10-二乙氧基蒽、9,10-二丁氧基蒽及2-乙基-9,10-二丁氧基蒽等。
作為羧酸化合物,可例舉:苯基硫基乙酸、甲基苯基硫基乙酸、乙基苯基硫基乙酸、甲基乙基苯基硫基乙酸、二甲基苯基硫基乙酸、甲氧基苯基硫基乙酸、二甲氧基苯基硫基乙酸、氯苯基硫基乙酸、二氯苯基硫基乙酸、N-苯基甘胺酸、苯氧基乙酸、萘硫基乙酸、N-萘基甘胺酸及萘氧基乙酸等。
於使用該等聚合起始助劑(D1)之情形時,其含量相對於著色樹脂組合物中所含之所有樹脂(B)及聚合性化合物(C)之合計量100質量份,較佳為0.1質量份以上30質量份以下,更佳為1質量份以上20質量份以下。
<溶劑(E)>
溶劑(E)並無特別限定,可使用該領域中通常使用之溶劑。
溶劑(E)例如可例舉:酯溶劑(分子內包含-COO-且不含-O-之溶劑)、醚溶劑(分子內包含-O-且不含-COO-之溶劑)、醚酯溶劑(分子內包含-COO-及-O-之溶劑)、酮溶劑(分子內包含-CO-且不含-COO-之溶劑)、醇溶劑(分子內包含OH且不含-O-、-CO-及-COO-之溶劑)、芳香族烴溶劑、醯胺溶劑、二甲基亞碸等。該等溶劑亦可併用2種以上。
作為酯溶劑,可例舉:乳酸甲酯、乳酸乙酯、乳酸丁酯、2-羥基異丁烷酸甲酯、乙酸乙酯、乙酸正丁酯、乙酸異丁酯、甲酸戊酯、乙酸異戊酯、丙酸丁酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、環己醇乙酸酯及γ-丁內酯等。
作為醚溶劑,可例舉:乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚、3-甲氧基-1-丁醇、3-甲氧基-3-甲基丁醇、四氫呋喃、四氫哌喃、1,4-二㗁烷、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基乙基醚、二乙二醇二丙醚、二乙二醇二丁醚、大茴香醚、苯乙醚及甲基大茴香醚等。
作為醚酯溶劑,可例舉:甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯、乙酸3-甲氧基丁酯、乙酸3-甲基-3-甲氧基丁酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯及二丙二醇甲醚乙酸酯等。
作為酮溶劑,可例舉:4-羥基-4-甲基-2-戊酮、丙酮、2-丁酮、2-庚酮、3-庚酮、4-庚酮、4-甲基-2-戊酮、環戊酮、環己酮及異佛爾酮等。
作為醇溶劑,可例舉:甲醇、乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、丙二醇及甘油等。
作為芳香族烴溶劑,可例舉:苯、甲苯、二甲苯、1,3,5-三甲苯等。
作為醯胺溶劑,可例舉:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺及N-甲基吡咯啶酮等。
作為溶劑(E),較佳為丙二醇單甲醚乙酸酯、丙二醇單甲醚、乳酸乙酯及環己酮。
於包含溶劑(E)之情形時,溶劑(E)之含有率相對於著色樹脂組合物之總量,通常為99.99質量%以下,較佳為40質量%以上99質量%以下,更佳為50質量%以上95質量%以下,再佳為70質量%以上95質量%以下,進而更佳為75質量%以上90質量%以下。換言之,著色樹脂組合物之固形物成分之總量通常為0.01質量%以上,較佳為1質量%以上60質量%以下,更佳為5質量%以上50質量%以下,再佳為5質量%以上30質量%以下,進而更佳為10質量%以上25質量%以下。若溶劑(E)之含有率處於上述範圍內,則塗佈時之平坦性良好,又,形成彩色濾光片時色濃度不會不足,因此有顯示特性良好之趨勢。
<整平劑(F)>
作為整平劑(F),可例舉:矽酮系界面活性劑、氟系界面活性劑及具有氟原子之矽酮系界面活性劑等。該等亦可於側鏈具有聚合性基。
作為矽酮系界面活性劑,可例舉分子內具有矽氧烷鍵之界面活性劑等。具體而言,可例舉:Toray Silicone DC3PA、Toray Silicone SH7PA、Toray Silicone DC11PA、Toray Silicone SH21PA、Toray Silicone SH28PA、Toray Silicone SH29PA、Toray Silicone SH30PA、Toray Silicone SH8400(商品名;東麗道康寧(股)製造)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業(股)製造)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452及TSF4460(邁圖高新材料日本有限公司製造)等。
作為氟系界面活性劑,可例舉分子內具有氟碳鏈之界面活性劑等。具體而言,可例舉:Fluorad(註冊商標)FC430、Fluorad FC431(Sumitomo 3M(股)製造)、MEGAFAC(註冊商標)F142D、MEGAFAC F171、MEGAFAC F172、MEGAFAC F173、MEGAFAC F177、MEGAFAC F183、MEGAFAC F554、MEGAFAC R30、MEGAFAC RS-718-K(DIC(股)製造)、Eftop(註冊商標)EF301、Eftop EF303、Eftop EF351、Eftop EF352(三菱綜合材料電子化成(股)製造)、Surflon(註冊商標)S381、Surflon S382、Surflon SC101、Surflon SC105(旭硝子(股)製造)及E5844(大金精密化學研究所(股)製造)等。
作為具有氟原子之矽酮系界面活性劑,可例舉分子內具有矽氧烷鍵及氟碳鏈之界面活性劑等。具體而言,可例舉:MEGAFAC(註冊商標)R08、MEGAFAC BL20、MEGAFAC F475、MEGAFAC F477及MEGAFAC F443(DIC(股)製造)等。
於含有整平劑(F)之情形時,整平劑(F)之含有率相對於著色樹脂組合物之總量,較佳為0.0005質量%以上1質量%以下,更佳為0.001質量%以上0.5質量%以下,再佳為0.005質量%以上0.1質量%以下。再者,該含量中不包括顏料分散劑之含量。若整平劑(F)之含有率處於上述範圍內,則能夠使彩色濾光片之平坦性良好。
<其他成分>
著色樹脂組合物亦可視需要包含填充劑、其他高分子化合物、密接促進劑、驟冷劑、抗氧化劑、光穩定劑、鏈轉移劑等該技術領域中公知之添加劑。
<著色樹脂組合物之製造方法>
著色樹脂組合物可藉由將著色劑(A)、樹脂(B)、視需要使用之聚合性化合物(C)、聚合起始劑(D)、溶劑(E)、整平劑(F)及其他成分混合而製備。混合可藉由公知或慣用之裝置及條件進行。
著色劑(A)可預先與溶劑(E)之一部分或全部混合,以利用珠磨機等使其分散直至平均粒徑成為0.2 μm以下左右之狀態使用,較佳為以分散之狀態使用。此時,亦可視需要調配上述分散劑、樹脂(B)之一部分或全部。又,著色劑(A)亦可以預先溶解於溶劑(E)之一部分或全部之狀態使用。藉由在如此獲得之含著色劑液體中將其餘成分以成為特定濃度之方式混合,能夠製備目標著色樹脂組合物。
<彩色濾光片之製造方法>
能夠由著色樹脂組合物形成可作為色彩轉換層之彩色濾光片。作為形成著色圖案之方法,可例舉:光微影法、噴墨法、印刷法等。其中,較佳為光微影法。光微影法係將上述著色樹脂組合物塗佈於基板,使其乾燥而形成著色樹脂組合物層,經由光罩使該著色樹脂組合物層曝光,並進行顯影之方法。於光微影法中,藉由曝光時不使用光罩及/或不進行顯影,能夠形成上述著色樹脂組合物層之硬化物即著色塗膜。如此形成之著色圖案及著色塗膜為本發明之彩色濾光片。
所製作之彩色濾光片之膜厚並無特別限定,可根據目的或用途等適當進行調整,例如為0.1 μm以上30 μm以下,較佳為0.1 μm以上20 μm以下,再佳為0.5 μm以上6 μm以下。
作為基板,可使用石英玻璃、硼矽酸玻璃、鋁矽酸鹽玻璃、對表面進行了氧化矽塗佈之鈉鈣玻璃等玻璃板、或者聚碳酸酯、聚甲基丙烯酸甲酯、聚對苯二甲酸乙二酯等樹脂板、矽、於上述基板上形成有鋁、銀、銀/銅/鈀合金薄膜等者。亦可於該等基板上形成另一彩色濾光片層、樹脂層、電晶體、電路等。
利用光微影法進行之各色像素之形成可藉由公知或慣用之裝置及條件進行。例如可以如下方式製作。
首先,將著色樹脂組合物塗佈於基板上,進行加熱乾燥(預烘烤)及/或減壓乾燥,藉此去除溶劑等揮發成分,使其乾燥,獲得平滑之著色樹脂組合物層。
作為塗佈方法,可例舉:旋轉塗佈法、狹縫式塗佈法、狹縫與旋轉塗佈法等。
進行加熱乾燥之情形時之溫度較佳為30℃以上120℃以下,更佳為50℃以上110℃以下。又,關於加熱時間,較佳為10秒以上60分鐘以下,更佳為30秒以上30分鐘以下。
於進行減壓乾燥之情形時,較佳為於50 Pa以上150 Pa以下之壓力下、20℃以上25℃以下之溫度範圍內進行。
著色樹脂組合物層之膜厚並無特別限定,只要根據目標彩色濾光片之膜厚適當進行選擇即可。
接下來,著色樹脂組合物層經由用於形成目標著色圖案之光罩進行曝光。該光罩上之圖案並無特別限定,可使用與目標用途對應之圖案。又,為了能夠對整個曝光面均勻照射平行光線、或者進行光罩與形成有著色樹脂組合物層之基板之準確對位,較佳為使用光罩對準曝光機及步進式曝光機等曝光裝置。
作為用於曝光之光源,較佳為產生波長為250 nm以上450 nm以下之光之光源。例如可針對未達350 nm之光,使用將該波長區域截止之濾波器進行截止,或者針對436 nm附近、408 nm附近、365 nm附近之光,使用將該等波長區域提取之帶通濾波器選擇性進行提取。具體而言,可例舉:水銀燈、發光二極體、金屬鹵化物燈、鹵素燈等。
藉由使曝光後之著色樹脂組合物層與顯影液接觸進行顯影,而於基板上形成著色圖案。藉由顯影,著色樹脂組合物層之未曝光部溶解於顯影液中而被去除。作為顯影液,例如較佳為氫氧化鉀、碳酸氫鈉、碳酸鈉、氫氧化四甲基銨等鹼性化合物之水溶液。該等鹼性化合物之水溶液中之濃度較佳為0.01質量%以上10質量%以下,更佳為0.03質量%以上5質量%以下。進而,顯影液亦可包含界面活性劑。
顯影方法可為覆液法、浸漬法及噴霧法等任一方法。進而亦可於顯影時使基板傾斜任意角度。
顯影後之基板進行水洗為佳。
進而對所獲得之著色圖案進行後烘烤為佳。後烘烤溫度較佳為150℃以上250℃以下,更佳為160℃以上240℃以下。後烘烤時間較佳為1分鐘以上120分鐘以下,更佳為10分鐘以上60分鐘以下。
<顯示裝置>
上述彩色濾光片可用作顯示裝置(例如,液晶顯示裝置、有機EL(Electroluminescence,電致發光)裝置、電子紙等)及固體攝像元件中使用之彩色濾光片,其中,可用作有機EL裝置中使用之彩色濾光片。
[實施例]
以下,例舉實施例對本發明更具體地進行說明,但本發明當然不受下述實施例限制,當然亦可於能夠切合上述、下述主旨之範圍內適當加以變更而實施,其等均包含於本發明之技術範圍內。再者,以下,只要未特別說明,則「份」意指「質量份」,「%」意指「質量%」。
於以下之實施例中,化合物之結構係藉由質譜分析(LC:Agilent製造之1200型;MASS:Agilent製造之LC/MSD6130型)進行確認。
樹脂之聚苯乙烯換算之重量平均分子量(Mw)及數量平均分子量(Mn)之測定係藉由GPC(Gel Permeation Chromatography,凝膠滲透色譜)法於以下條件下進行。
裝置:HLC-8120GPC(東梭(股)製造)
管柱:TSK-GELG2000HXL
管柱溫度:40℃
溶劑:四氫呋喃
流速:1.0 mL/分鐘
分析試樣之固形物成分濃度:0.001~0.01質量%
注入量:50 μL
檢測器:RI
校正用標準物質:TSK STANDARD POLYSTYRENE F-40、F-4、F-288、A-2500、A-500(東梭(股)製造)
將上述獲得之聚苯乙烯換算之重量平均分子量及數量平均分子量之比(Mw/Mn)作為分散度。
合成例1
添加3,4,9,10-苝四羧酸二酐(東京化成工業(股)製造)8.0份、7-十三胺(東京化成工業(股)製造)10份、乙酸鋅1.3份(關東化學(股)製造)、及咪唑(東京化成工業(股)製造)314份,於150℃攪拌3小時。將所獲得之混合物保持於20℃以下,同時加入預先製備之37%鹽酸(關東化學(股)製造)267份及水1300份,結果產生橙紅色之沈澱物。將包含該橙紅色之沈澱物之混合物過濾,利用水400份、甲醇200份將過濾後之殘渣洗淨。以60℃對所獲得之殘渣進行減壓乾燥,獲得式(I-2)所表示之化合物(化合物(I-2))12份(產率79%)。
<化合物(I-2)之鑑定>
(質譜分析)離子化模式=ESI(Electrospray Ionization,電灑離子化)+:m/z=[M+H]
+755
準確質量(Exact Mass):754
合成例2
添加合成例1中所獲得之化合物(I-2)5.0份、氫氧化鉀1.5份(關東化學(股)製造)、及第三丁醇(關東化學(股)製造)10份,於80℃攪拌1小時。冷卻至0℃,將所獲得之混合物保持於20℃以下,同時加入預先製備之鹽酸(關東化學(股)製造)10份及水48份,結果產生紫紅色之沈澱物。將包含該藍紫色之沈澱物之混合物過濾,利用水400份、乙醇15份將過濾後之殘渣洗淨。以60℃對所獲得之殘渣進行減壓乾燥,利用矽膠管柱(溶劑:氯仿/乙酸=50/1、vol/vol)進行純化,結果獲得式(I-3)所表示之化合物(化合物(I-3))2.3份(產率61%)。
<化合物(I-3)之鑑定>
(質譜分析)離子化模式=ESI+:m/z=[M+H]
+574
準確質量:573
合成例3
添加合成例2中所獲得之化合物(I-3)5.0份、咪唑20份(東京化成工業(股)製造)、及4-二甲基胺基吡啶(東京化成工業(股)製造)21份,於170℃攪拌15小時。冷卻至90℃,向所獲得之混合物中加入預先製備之鹽酸(關東化學(股)製造)520份、水2600份及乙醇2100份,結果產生紫紅色之沈澱物。將包含該紫紅色之沈澱物之混合物過濾,利用水400份、乙醇15份將過濾後之殘渣洗淨。以60℃對所獲得之殘渣進行減壓乾燥,利用矽膠管柱(溶劑:氯仿/乙酸乙酯=2/1、vol/vol)進行純化,結果獲得式(I-4)所表示之化合物(化合物(I-4))1.0份(產率19%)。
<化合物(I-4)之鑑定>
(質譜分析)離子化模式=ESI+:m/z=[M+H]
+596
準確質量:595
合成例4
向具備回流冷卻器、滴液漏斗及攪拌機之燒瓶內通入適量氮氣,置換為氮氣氛圍,放入丙二醇單甲醚乙酸酯280份,一面攪拌一面加熱至80℃。然後,花費5小時滴加丙烯酸38份、丙烯酸3,4-環氧三環[5.2.1.0
2,6]癸烷-8-基酯及丙烯酸3,4-環氧三環[5.2.1.0
2,6]癸烷-9-基酯之混合物(含有比以莫耳比計為1:1)289份、丙二醇單甲醚乙酸酯125份之混合溶液。另一方面,花費6小時滴加於丙二醇單甲醚乙酸酯235份中溶解有2,2-偶氮雙(2,4-二甲基戊腈)33份之溶液。滴加結束後,於80℃保持4小時之後,冷卻至室溫,獲得固形物成分為35.1%且利用B型黏度計(23℃)測得之黏度為125 mPa・s之共聚物(樹脂B1)溶液。生成之共聚物之重量平均分子量Mw為9.2×10
3,分散度為2.08,固形物成分換算之酸值為77 mg-KOH/g。樹脂B1具有以下結構單元。
實施例1
(1)著色樹脂組合物1之製備
將以下成分混合,獲得著色樹脂組合物1。
(A)著色劑:式(I-4)所表示之化合物 2.6份
(B)樹脂:樹脂B1溶液 54份
(E)溶劑:丙二醇單甲醚乙酸酯 420份
(2)著色樹脂組合物1'之製備
然後,將以下成分混合,獲得著色樹脂組合物1'。
著色樹脂組合物1 478份
(C)聚合性化合物:二季戊四醇六丙烯酸酯(Kayarad(註冊商標)DPHA;日本化藥(股)製造) 40份
(D)聚合起始劑:N-苯甲醯氧基-1-(4-苯基硫基苯基)辛烷-1-酮-2-亞胺(Irgacure(註冊商標)OXE 01;BASF公司製造) 2份
(F)整平劑:聚醚改性矽酮油(Toray Silicone SH8400;東麗道康寧(股)製造) 0.15份
(2)著色塗膜(彩色濾光片)之製作
利用旋轉塗佈法將著色樹脂組合物以後烘烤後之膜厚成為2.0 μm之方式塗佈於5 cm見方之玻璃基板(Eagle XG;康寧公司製造)上,之後於100℃進行3分鐘預烘烤,形成著色組合物層。自然冷卻後,使用曝光機(TME-150RSK;TOPCON(股)製造)於大氣氛圍下以80 mJ/cm
2之曝光量(365 nm基準)對形成於基板上之著色組合物層進行光照射。光照射後,於烘箱中在230℃進行30分鐘後烘烤,獲得著色塗膜。
再者,著色塗膜之膜厚係使用DEKTAK3(日本真空技術(股)製造)進行測定。
(3)對比度評估
針對所獲得之著色塗膜,使用對比度計(CT-1:壺阪電機(股)、色彩色差計BM-5A:TOPCON公司製造、光源:F-10、偏光膜:壺阪電機(股))測定對比度。再者,測定時之空白值為30,000。若著色塗膜之對比度良好,則可以說由相同著色樹脂組合物製作之著色圖案亦具有良好之對比度。將結果示於表6。
比較例1
除了將實施例1之式(I-4)所表示之化合物替換成式(I-2)所表示之化合物以外,進行與實施例1相同之操作,製作著色樹脂組合物及著色塗膜,進行對比度評估。將結果示於表6。
[表6]
對比度 | |
實施例1 | 6800 |
比較例1 | 333 |
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