TW202033675A - 著色組成物 - Google Patents
著色組成物 Download PDFInfo
- Publication number
- TW202033675A TW202033675A TW109105489A TW109105489A TW202033675A TW 202033675 A TW202033675 A TW 202033675A TW 109105489 A TW109105489 A TW 109105489A TW 109105489 A TW109105489 A TW 109105489A TW 202033675 A TW202033675 A TW 202033675A
- Authority
- TW
- Taiwan
- Prior art keywords
- coloring composition
- acrylate
- meth
- color filter
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 238000004040 coloring Methods 0.000 title claims abstract description 68
- -1 methine compound Chemical class 0.000 claims abstract description 103
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- 239000002270 dispersing agent Substances 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 15
- 239000011230 binding agent Substances 0.000 claims abstract description 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 239000000049 pigment Substances 0.000 claims description 34
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 8
- 238000003384 imaging method Methods 0.000 claims description 7
- 239000004973 liquid crystal related substance Substances 0.000 claims description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006226 butoxyethyl group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 77
- 238000000034 method Methods 0.000 description 26
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- 239000000975 dye Substances 0.000 description 17
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- 239000000126 substance Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 11
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- 239000002904 solvent Substances 0.000 description 10
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
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- 239000000243 solution Substances 0.000 description 5
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- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 4
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
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- 238000001914 filtration Methods 0.000 description 4
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
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- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 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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- 230000035484 reaction time Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019259 sodium dehydroacetate Nutrition 0.000 description 1
- 229940079839 sodium dehydroacetate Drugs 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
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- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- SHBDDIJUSNNBLQ-UHFFFAOYSA-M sodium;3-[[4-[(2-chlorophenyl)-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)Cl)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SHBDDIJUSNNBLQ-UHFFFAOYSA-M 0.000 description 1
- FJBHGWADYLMEJG-UHFFFAOYSA-M sodium;3-[[4-[[4-(diethylamino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC=1C=C(C=CC=1)S([O-])(=O)=O)=C(C=C1)C=CC1=[N+](CC)CC1=CC=CC(S([O-])(=O)=O)=C1 FJBHGWADYLMEJG-UHFFFAOYSA-M 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 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
- 150000003573 thiols Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229950001577 trimetozine Drugs 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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本發明係關於形成彩色濾光片之綠色像素時所使用之含次甲基化合物之著色組成物、使用該著色組成物所形成之彩色濾光片、以及使用該彩色濾光片所形成之液晶顯示裝置、成像元件(CCD、CMOS)及有機EL顯示器等電子顯示裝置。
使用作為以筆記型電腦或液晶電視、行動電話、智慧型手機等為代表之液晶顯示器(LCD)或有機EL顯示器等液晶顯示裝置、及數位相機或彩色影印機等輸入裝置之成像元件(CCD、CMOS)之彩色化中需要彩色濾光片。該等液晶顯示裝置或固體成像元件所使用彩色濾光片之製造方法有染色法、電鍍法、印刷法、顏料分散法等,近年來主流為使用圖案化手法之顏料分散法。圖案化方法之代表為光刻法,係使用感光性樹脂組成物與顏料分散體的混合物而形成彩色濾光片。又,最近亦進行將著色印墨藉由噴墨印表機不透過遮罩而直接塗佈於基板上,而形成彩色濾光片之方法。
提高彩色濾光片所求特性之色純度、彩度、亮度及對比是非常重要的。藉由提高亮度而可抑制背光光量,結果會降低消耗的電力,
故為環保上的必要技術。為了提高彩色濾光片之色純度,需要增加著色顏料的含量、或選擇更佳分光波形之顏料。另一方面,在提高亮度時需要減少顏料濃度或減低膜厚,藉此提高透過率。為了兼具該等相反特性而進行顏料微粒子化之方法,但著色組成物之分散穩定性、以及彩色濾光片相對於光、熱或溶劑之耐性及對比的提高有其限度,目前係即使提高亮度也難以兼具耐受性。
為了解決該等問題之其他方案是檢討使用染料之彩色濾光片。使用染料的優點係為了可達成顏料無法達成之兼具色純度及亮度、或可抑制光散射而可提高對比。但是,另一方面,電視用等需要長期信頼性之顯示體用途需要優異的耐光性或耐熱性,一般而言,染料之耐受性比顏料差。又,至今盛行開發彩色濾光片用之藍色及紅色色素,但綠色色素的開發與前者相比其數量有限。其中例如專利文獻1至6係關於組合酞青素之綠色染料與補色之黃色染料與樹脂之綠色彩色濾光片。又,專利文獻7及8係關於使用次甲基化合物之彩色濾光片用綠色著色組成物。但該等文獻中並未記載彩色濾光片之亮度。亦即,目前為顯示裝置或固體成像元件領域所使用之綠色彩色濾光片並未充分滿足亮度之要求特性。
[先前技術文獻]
[專利文獻]
專利文獻1:日本專利第5545313號公報。
專利文獻2:日本特開2018-17856號公報。
專利文獻3:日本特開2018-111757號公報。
專利文獻4:日本特開2018-169505號公報。
專利文獻5:日本特開2016-006137號公報。
專利文獻6:日本專利第6440494號公報。
專利文獻7:日本特開2017-179177號公報。
專利文獻8:日本特開2018-154782號公報。
本發明目的在於提供可製造亮度優異之高品質、高信賴性之彩色濾光片之新穎著色組成物、及使用其製造之彩色濾光片。
本發明人等為解決前述課題而努力研究,結果發現藉由使用具有特定構造之含次甲基化合物之著色組成物而可解決上述課題,從而完成本發明。
亦即本發明如下。
(1)一種彩色濾光片用著色組成物,係含有下述式(1)所示之次甲基化合物、黏合劑樹脂及分散劑,
(式(1)中,R1至R4各自獨立地表示氫原子、鹵原子、碳數1至4之烷基、甲氧基或硝基。R5表示碳數1至4之烷基、甲氧基乙基或丁氧基乙基。R6至R10各自獨立地表示氫原子、鹵原子、碳數1至6之烷基、甲氧基、碳數1至3之烷基羰基胺基或-SO3 -。但,R6至R10之至少一者表示-SO3 -)。
(2)如前項(1)所述之彩色濾光片用著色組成物,其中R1至R4各自獨立地為氫原子,鹵原子或碳數1至4之烷基,且R7及R9之任一者為-SO3 -且另一者為氫原子、鹵原子、碳數1至6之烷基、甲氧基或碳數1至3之烷基羰基胺基。
(3)如前項(1)或(2)所述之彩色濾光片用著色組成物,其中分散劑含有丙烯酸系分散劑。
(4)如前項(1)至(3)中任一項所述之彩色濾光片用著色組成物,其進一步含有顏料。
(5)如前項(4)所述之彩色濾光片用著色組成物,其中顏料含有具有酞青素構造之顏料。
(6)一種彩色濾光片,係使用前項(1)至(5)中任一項所述之彩色濾光片用著色組成物而得。
(7)一種液晶顯示裝置、有機EL顯示器或固體成像元件,係裝設有前項(6)所述之彩色濾光片。
藉由使用本發明之彩色濾光片用著色組成物而可提供亮度優異之高品質、高信賴性之彩色濾光片之綠色像素。
本發明之彩色濾光片用著色組成物(以下稱為「著色組成物」)係含有前述式(1)所示之次甲基化合物。
式(1)中,R1至R4各自獨立地表示氫原子、鹵原子、碳數1至4之烷基、甲氧基或硝基。
式(1)之R1至R4所示鹵原子可舉出氟原子、氯原子、溴原子及碘原子,較佳為氯原子。
式(1)之R1至R4所示碳數1至4之烷基可舉出甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基及第三丁基,較佳為甲基。
較佳為式(1)之R1至R4各自獨立地為氫原子、鹵原子或碳數1至4之烷基。更佳為R1至R4中選擇之2個或3個為氫原子,且此外各自獨立地為氫原子、鹵原子或碳數1至4之烷基。又更佳為R4為氫原子、R1至R3中選擇之1個或2個為氫原子、且此外各自獨立地為氫原子、鹵原子或碳數1至4之烷基,特佳為R4為氫原子、R1至R3中選擇之1個或2個為氫原子、且此外為鹵原子或碳數1至4之烷基,最佳為R4為氫原子、R1至R3中選擇之1個或2個為氫原子、且此外為碳數1至4之烷基。
式(1)中,R5表示碳數1至4之烷基、甲氧基乙基或丁氧基乙基。
式(1)之R5較佳為碳數1至4之烷基。
式(1)之R5所示碳數1至4之烷基可舉出與式(1)之R1至R4所示碳數1至4之烷基相同者。較佳為甲基。
式(1)中,R6至R10各自獨立地表示氫原子、鹵原子、碳數1至6之烷基、甲氧基、碳數1至3之烷基羰基胺基或-SO3 -。但,R6至R10之至少一者表示-SO3 -。
式(1)之R6至R10所示之鹵原子可舉出與式(1)之R1至R4所示之鹵原子為相同者,較佳為氯原子、溴原子或碘原子。更佳為氯原子。
式(1)之R6至R10所示碳數1至6之烷基只要為碳數1至6之烷基則可為直鏈狀、支鏈狀或環狀,無特別限定。其具體例可舉出甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、2,2-二甲基丙基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基-1-甲基丙基及環己基等。
式(1)之R6至R10所示碳數1至3之烷基羰基胺基可舉出甲基羰基胺基、乙基羰基胺基、正丙基羰基胺基及異丙基羰基胺基。較佳為甲基羰基胺基或異丙基羰基胺基。
式(1)之R6至R10之較佳者係R7或R9為-SO3 -、且此外各自獨立地為氫原子、鹵原子、碳數1至6之烷基、甲氧基或碳數1至3之烷基羰基胺基。更佳者係R6及R10為氫原子、R7或R9為-SO3 -、且此外各自獨立地為氫原子、鹵原子、碳數1至6之烷基、甲氧基或碳數1至3之烷基羰基胺基。又更佳為R6及R10為氫原子、R7或R9為-SO3 -、且此外各自獨立地為氫原子、鹵原子、甲氧基或碳數1至3之烷基羰基胺基,特佳者係R6及R10為氫原子、R7及R9之任一者為-SO3 -且另一者為氫原子、且R8為氫原子、鹵原子、甲氧基或碳數1至3之烷基羰基胺基,最佳者係R6及R10為氫原子、R7及R9之任一者為-SO3 -且另一者為氫原子、且R8為鹵原子。
本發明之著色組成物所含有的式(1)所示之次甲基化合物更佳為上述R1至R10各自較佳者之組合者,又更佳者係上述R1至R10各自更佳者之組合。
本發明之著色組成物所含有的式(1)所示之次甲基化合物可用各種方法製造。例如可參考專利文獻7所記載之方法並用以下方法製造。再者,下述式(AA)至(D)中之R1至R10各自表示與上述式(1)中的R1至R10同義。
首先藉由使市售可得之下述式(AA)所示之化合物與對甲苯磺酸甲氧酯乙基及對甲苯磺酸丁氧基乙酯等烷氧基烷基化劑、或對甲苯磺酸烷酯及二烷基硫酸等烷基化劑反應,轉換為下述式(B)之所示衍生物。接著藉由常法之Vilsmeier反應而轉換為下述式(C)所示的甲醯基衍生物。
另一方面,藉由使市售可得之下述式(D)所示之化合物與上述式(C)所示甲醯基衍生物縮合反應,可得到對應之上述式(1)所示之次甲基化合物。
上述縮合步驟中的反應溫度較佳為20至60℃,更佳為30至50℃。
上述縮合步驟所使用之溶劑較佳為例如甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、N-甲基吡咯啶酮(以下稱為NMP)、水、鹽酸水、硫酸水、乙酸及丙酸等。該等可單獨或混合使用。
可在上述縮合步驟中添加酸觸媒。酸觸媒之具體例可舉出鹽酸及硫酸等無機酸類、氯化鋁等路易士酸等。
以下呈示式(1)所示之次甲基化合物之具體例,但本發明之著色組成物所含有的式(1)所示之次甲基化合物並不限定於該等。
本發明之著色組成物中的式(1)所示之次甲基化合物的含量相對於本發明之著色組成物之全固形分(本發明之著色組成物所含有的溶劑類以外之全部成分)一般為0.5至50質量%,較佳為1至30質量%。
再者,本發明之著色組成物中可併用式(1)所包含的複數種次甲基化合物。在併用時,式(1)所包含的次甲基化合物之總量成為前述範圍之量即可。
本發明之著色組成物含有黏合劑樹脂。著色組成物所含有之黏合劑樹脂並無特別限定,可舉出以往習知者。本發明之著色組成物用於光刻手法時,較佳為以下所舉出具有1個以上之羧基或羥基之乙烯性不飽和單體、或其他具有可共聚之芳香族烴基或脂肪族烴基之乙烯性不飽和單體等共聚物。又,亦可使用該等側鏈或末端等具有環氧基者且進一步加成丙烯酸酯而成之丙烯酸環氧酯樹脂。該等單體等可單獨或組合2種以上。
本發明可使用之前述具有羧基之乙烯性不飽和單體之具體例可舉出丙烯酸、甲基丙烯酸、巴豆酸、α-氯丙烯酸、乙基丙烯酸、桂皮
酸等不飽和單羧酸類;馬來酸、馬來酸酐、延胡索酸、伊康酸、伊康酸酐、檸康酸、檸康酸酐、中康酸等不飽和二羧酸(酐)類;3價以上之不飽和多羧酸(酐)類、2-(甲基)丙烯醯氧基乙基六氫鄰苯二甲酸、2-甲基丙烯醯氧基乙基2-羥基丙基鄰苯二甲酸酯、2-丙烯醯氧基乙基2-羥基乙基鄰苯二甲酸等。該等可單獨使用或混合2種以上使用。
本發明可使用之前述具有羥基之乙烯性不飽和單體之具體例可舉出(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3-羥基丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸3-羥基丁酯、(甲基)丙烯酸5-羥基戊酯、(甲基)丙烯酸4-羥基戊酯、(甲基)丙烯酸3-羥基戊酯、(甲基)丙烯酸6-羥基己酯、(甲基)丙烯酸5-羥基己酯、(甲基)丙烯酸4-羥基己酯、(甲基)丙烯酸5-羥基-3-甲基-戊酯、環己烷-1,4-二甲醇-單(甲基)丙烯酸酯、(甲基)丙烯酸2-(2-羥基乙基氧基)乙酯、甘油單甲基丙烯酸酯、聚乙二醇單(甲基)丙烯酸酯、聚丙二醇單(甲基)丙烯酸酯、聚(乙二醇-丙二醇)單甲基丙烯酸酯等羥基末端聚烷二醇單(甲基)丙烯酸酯等。該等可單獨使用或混合2種以上使用。
又,前述其他可共聚之乙烯性不飽和單體可舉例如苯乙烯、α-甲基苯乙烯、鄰乙烯基甲苯、間乙烯基甲苯、對乙烯基甲苯、鄰氯苯乙烯、間氯苯乙烯、對氯苯乙烯、對甲氧基苯乙烯等芳香族乙烯基化合物;(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸苄酯、對異丙苯基苯氧基乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2-
羥基-3-苯氧基丙酯、鄰苯基酚環氧丙基醚(甲基)丙烯酸酯、鄰苯基酚(甲基)丙烯酸酯羥基乙基化物、(甲基)丙烯酸苯氧基乙酯等不飽和羧酸酯類;(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸三甲基環己酯、(甲基)丙烯酸降莰酯、(甲基)丙烯酸降莰基甲酯、(甲基)丙烯酸苯基降莰酯、(甲基)丙烯酸氰基降莰酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸莰酯、(甲基)丙烯酸薄荷腦酯、(甲基)丙烯酸葑酯、(甲基)丙烯酸金剛烷酯、(甲基)丙烯酸二甲基金剛烷酯、三環[5.2.1.02,6]癸-8-基=(甲基)丙烯酸酯、三環[5.2.1.02,6]癸-4-甲基=(甲基)丙烯酸酯、(甲基)丙烯酸環癸酯、2-(甲基)丙烯醯氧基乙基六氫鄰苯二甲酸、(甲基)丙烯酸第三丁基環己酯等脂環骨架類;聚乙二醇單(甲基)丙烯酸酯、聚丙二醇單(甲基)丙烯酸酯、聚(乙二醇-丙二醇)單甲基丙烯酸酯等羥基末端聚烷二醇單(甲基)丙烯酸酯類;甲氧基聚乙二醇單甲基丙烯酸酯、月桂氧基聚乙二醇單(甲基)丙烯酸酯、辛氧基聚乙二醇聚丙二醇單(甲基)丙烯酸酯、壬基苯氧基聚乙二醇單丙烯酸酯、壬基苯氧基聚丙二醇單丙烯酸酯、烯丙氧基聚乙二醇-聚丙二醇單(甲基)丙烯酸酯等烷基末端聚烷二醇單(甲基)丙烯酸酯類;丙烯酸2-胺基乙酯、甲基丙烯酸2-胺基乙酯、丙烯酸2-胺基丙酯、甲基丙烯酸2-胺基丙酯、丙烯酸3-胺基丙酯、甲基丙烯酸3-胺基丙酯等不飽和羧酸胺基烷酯類;丙烯酸環氧丙酯、甲基丙烯酸環氧丙酯、(甲基)丙烯酸3,4-環氧基丁酯、(甲基)丙烯酸(3,4-環氧環己基)甲酯、(甲基)丙烯酸4-羥基丁酯環氧丙基醚等不飽和羧酸環氧丙基酯類;乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、苯甲酸乙烯酯等羧酸乙烯酯類;乙烯基甲基醚、乙烯基乙基醚、烯丙基環氧丙基醚、甲基丙烯酸環氧丙基醚等不飽和醚類;丙烯腈、
甲基丙烯腈、α-氯丙烯腈、二氰亞乙烯等氰乙烯基化合物;丙烯醯胺、甲基丙烯醯胺、α-氯丙烯醯胺、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-(甲基)丙烯醯基鄰苯二甲醯亞胺、N-(2-羥基乙基)丙烯醯胺、N-(2-羥基乙基)甲基丙烯醯胺、馬來醯亞胺等不飽和醯胺或不飽和醯亞胺類;1,3-丁二烯、異戊二烯、氯丁二烯等脂肪族共軛二烯類;聚苯乙烯、聚甲基丙烯酸酯、聚甲基丙烯酸甲酯、聚丙烯酸正丁酯、聚甲基丙烯酸正丁酯、聚矽氧烷等於聚合物分子鏈末端具有單丙烯醯基或單甲基丙烯醯基之巨分子單體類等。該等可單獨使用或混合2種以上使用。
又,亦可使用於共聚物側鏈進一步導入有不飽和雙鍵之聚合物。可舉例如於馬來酸酐與可共聚之苯乙烯、乙烯基酚、丙烯酸、丙烯酸酯、丙烯醯胺等的共聚物之馬來酸酐部使丙烯酸羥基乙酯等具有醇性羥基之丙烯酸酯或甲基丙烯酸環氧丙酯等具有環氧基之丙烯酸酯反應而半酯化之化合物;及於丙烯酸、丙烯酸酯與丙烯酸羥基乙酯等具有醇性羥基之丙烯酸酯的共聚物之羥基使丙烯酸反應的化合物等。又,亦可使用胺甲酸乙酯樹脂或聚醯胺、聚醯亞胺樹脂、聚酯樹脂、市售ACA-200M(Daicel製)、ORGA-3060(大阪有機化學製)、AX3-BNX02(日本觸媒製)、UXE-3024(日本化藥製)、UXE-3000(日本化藥製)、ZGA-287H(日本化藥製)、TCR-1338H(日本化藥製)、ZXR-1722H(日本化藥製)、ZFR-1401H(日本化藥製)、ZCR-1642(日本化藥製)。
在製造本發明之著色組成物所含有的黏合劑樹脂(共聚物)時,係使用聚合起始劑。在此,合成共聚物時所使用之聚合起始劑之具體例可舉出α,α’-偶氮雙(異丁腈),2,2’-偶氮雙(2-甲基丁腈),過氧己酸第三
丁酯,二過氧第三丁基過氧化苯甲醯甲基乙酮過氧化物等。聚合起始劑之使用比例相對於共聚物之合成所使用的所有單體之合計100質量份為0.01至25質量份。又,合成共聚物時較佳為使用下述說明之有機溶劑,但係使用相對於所使用單官能之單體或聚合起始劑等具有充分溶解力者。合成共聚物時之反應溫度較佳為50至120℃,更佳為80至100℃。又,反應時間較佳為1至60小時,更佳為3至20小時。共聚物之較佳酸價為10至300(mgKOH/g),較佳羥基價為10至200(mgKOH/g)。藉由使酸價或羥基價成為10以上而可得到良好顯影性。共聚物之重量平均分子量(Mw)較佳為2,000至400,000,更佳為3,000至100,000。藉由使重量平均分子量為2,000至400,000而可得到良好靈敏度及顯影性等。
再者,在此所述酸價為根據JIS K-2501之方法測定的值,羥基價為根據JIS K-1557之方法測定的值。重量平均分子量為根據凝膠滲透層析法(GPC)之測定結果以聚苯乙烯換算所計算的值。
前述黏合劑樹脂係可於本發明之著色組成物中單獨使用或混合2種以上使用。本發明之著色組成物中,黏合劑樹脂含量相對於著色組成物之全固形分一般為1至99質量%,較佳為5至50質量%。
本發明之著色組成物含有分散劑。可與油溶性有機溶劑併用之分散劑可舉出十二烷基苯磺酸鈉、月桂酸鈉、萘磺酸之福馬林縮合物、烷基萘磺酸之福馬林縮合物、雜酚油磺酸之福馬林縮合物、聚氧伸乙基烷基醚硫酸酯之銨鹽、聚氧伸乙基烷基苯基醚硫酸酯之銨鹽、聚氧烷基醚磷酸酯鹽等習知之陰離子界面活性劑、乙烯基萘衍生物、α,β-乙烯性不飽和羧酸之脂肪族醇酯等苯乙烯、苯乙烯衍生物、丙烯酸、丙烯酸衍生
物、甲基丙烯酸、甲基丙烯酸衍生物、馬來酸、馬來酸衍生物、馬來酸酐、馬來酸酐衍生物、伊康酸、伊康酸衍生物、反丁烯二酸、反丁烯二酸衍生物等中選擇之至少2種以上的單體所構成之嵌段共聚物、或無規共聚物、或該等鹽等高分子分散劑等。
可與水溶性有機溶劑或水併用之分散劑除了界面活性劑以外,適合使用高分子分散劑。高分子分散劑之具體例可舉出聚乙烯醇類、聚乙烯吡咯啶酮類、聚丙烯酸、丙烯酸/丙烯腈共聚物、丙烯酸鹽/丙烯腈共聚物、乙酸乙烯酯/丙烯酸酯共聚物、丙烯酸/丙烯酸酯共聚物等丙烯酸系樹脂、苯乙烯/丙烯酸共聚物、苯乙烯/甲基丙烯酸共聚物、苯乙烯/甲基丙烯酸/丙烯酸酯共聚物、苯乙烯-α-甲基苯乙烯/丙烯酸共聚物、苯乙烯-α-甲基苯乙烯/丙烯酸/丙烯酸酯共聚物等苯乙烯/丙烯酸樹脂、苯乙烯/馬來酸共聚物、苯乙烯/馬來酸酐共聚物、異丁烯/馬來酸樹脂、松脂改質馬來酸樹脂、乙烯基萘/丙烯酸共聚物、乙烯基萘/馬來酸共聚物、及乙酸乙烯酯/乙烯共聚物、乙酸乙烯酯/脂肪酸乙烯基乙烯酯共聚物、乙酸乙烯酯/馬來酸酯共聚物、乙酸乙烯酯/巴豆酸共聚物、乙酸乙烯酯/丙烯酸共聚物等乙酸乙烯酯系共聚物及該等的鹽。
又,其他樹脂系分散劑可舉出聚胺甲酸乙酯樹脂系、聚羧酸系、聚醯胺樹脂系及聚酯樹脂系等分散劑。樹脂系分散劑之具體例係例如有ED211(楠本化成製),AJISPER PB821(Ajinomoto Fine-Techno製),SOLSPERSE 71000(Avecia製),DISPERBYK-2001(BYK.JAPAN公司製)等。
該等分散劑類相對於本發明之著色組成物所含有的式(1)所示之次甲基化合物及可任意含有之式(1)所示之次甲基化合物以外之色素之合計量,一般係使用800質量%以下,較佳為10至700質量%,更佳為80至600質量%。
本發明之著色組成物可含有式(1)所示之次甲基化合物、黏合劑樹脂及分散劑以外之成分(以下稱為「其他成分」)。
其他成分可舉例如油溶性有機溶劑、水溶性有機溶劑以及水等溶劑類或樹脂類,又可舉例如可與該等溶劑類或樹脂類組合使用之各種添加劑等。可將該等一種或二種以上配合著色組成物之用途或用法使用,並無特別限制。
油溶性有機溶劑之具體例可舉出乙醇、戊醇、辛醇、環己醇、苄醇、四氟丙醇等醇類;乙二醇單乙基醚、二乙二醇單乙基醚、二乙二醇單丁基醚、丙二醇單乙基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、三乙二醇單乙基醚、乙二醇二乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇二乙酸酯等二醇衍生物;甲基乙酮、環己酮等酮類;丁基苯基醚、苄基醚、己基醚等醚類;乙酸乙酯、乙酸丁酯、苯甲酸乙酯、苯甲酸丁酯、月桂酸乙酯、月桂酸丁酯等酯類;乙腈、N,N-二甲基甲醯胺(以下稱為DMF)、二甲基亞碸、環丁碸、NMP、2-吡咯啶酮等極性有機溶劑等。
水溶性有機溶劑可舉例如甲醇、乙醇、丙醇、異丙醇、丁醇、異丁醇、第三丁醇、戊醇及苄醇等醇類;乙二醇、二乙二醇、三乙二醇、丙二醇、聚乙二醇、聚丙二醇、甘油、三羥甲基丙烷、1,3-戊二醇及1,5-戊二醇等多元醇類;乙二醇單甲基醚、乙二醇單乙基醚、二乙二醇單
甲基醚、二乙二醇單丁基醚、三乙二醇單乙基醚、三乙二醇單丁基醚及二丙二醇單甲基醚等二醇衍生物;乙醇胺、二乙醇胺、三乙醇胺及嗎啉等胺類;2-吡咯啶酮、NMP、1,3-二甲基-咪唑啶酮等。
該等溶劑類可單獨使用或組合2種以上使用。含有溶劑類時,使用量相對於著色組成物之全固形分100質量份較佳為40至10,000質量份,更佳為100至1,000質量份。
本發明之著色組成物可含有之溶劑類以外之其他成分可舉例如樹脂類、硬化劑、光聚合起始劑、熱聚合起始劑、表面調整劑、消泡劑、防腐防黴劑、pH調整劑及式(1)所示之次甲基化合物以外之色素等。
本發明之著色組成物可含有之樹脂類可舉例如聚醯胺系、聚胺甲酸乙酯系、聚酯系、環氧系及聚丙烯酸系之樹脂等。
本發明之著色組成物可含有之聚醯胺樹脂、聚胺甲酸乙酯樹脂、聚酯樹脂、環氧樹脂及聚丙烯酸樹脂並無特別限定,可舉出以往習知者。
本發明之著色組成物可含有之硬化劑在自由基聚合時可舉出光聚合單體,在離子硬化時可舉出環氧樹脂,其他可舉出三聚氰胺硬化劑等。該等具體例可舉出(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2-乙基己酯、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(甲基)丙烯酸酯、四乙二醇(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、新戊四醇二(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯、甘油(甲基)丙烯酸酯、雙酚A型環氧基二(甲基)丙烯酸酯、雙酚F型環氧基二(甲基)丙烯酸酯、雙酚茀型環氧基二(甲基)丙烯酸酯、乙氧基
化三羥甲基丙烷三(甲基)丙烯酸酯、丙氧基化三羥甲基丙烷三(甲基)丙烯酸酯、乙氧基化甘油三(甲基)丙烯酸酯、乙氧基化異三聚氰酸三(甲基)丙烯酸酯、雙三羥甲基丙烷四(甲基)丙烯酸酯、乙氧基化新戊四醇四(甲基)丙烯酸酯、9,9-雙〔4-(2-丙烯醯氧基乙氧基)苯基〕茀、KAYARAD RP-1040(日本化藥製)、KAYARAD DPCA-30(日本化藥製)、UA-33H(新中村化學製)、UA-53H(新中村化學製)、M-8060(東亞合成製);硫醇系聚合單體可舉出TEMPIC(堺化學製)、TMMP(堺化學製)、PEMP(堺化學製)、DPMP(堺化學製);環氧樹脂可舉出日本化藥製品之NC-6000、NC-3000、EOCN-1020、XD-1000、EPPN-501H、BREN-S、NC-7300L、Daicel化學製品之CELLOXIDE 2021P、EHPE3150、CYCLOMER M100、EPOLEAD PB3600、JAPAN EPOXY RESIN製品之EPIKOTE 828、EPIKOTE YX8000、EPIKOTE YX4000、SILA-ACE S510(chisso製)、TEPIC(日產化學工業製)等;三聚氰胺硬化劑可舉出羥甲基化三聚氰胺或Mw-30(三和化學製)等。該等可單獨使用或混合2種以上使用。該等含量相對於著色組成物之全固形分100質量份一般為80質量份以下,較佳為5至30質量份。
本發明之著色組成物可含有之光聚合起始劑較佳為對於曝光光源一般使用之超高壓汞燈所射出的紫外線具有充分靈敏度者。可舉例如自由基聚合性之光自由基起始劑、離子硬化性之光酸產生劑或光鹼產生劑等。光聚合中,為了以更少曝光能量硬化,可組合稱為敏化劑之聚合促進劑成分使用。可使用之光聚合起始劑並無特別限制,具體例可舉出二苯乙二酮(benzil)、安息香***、安息香丁基醚、安息香丙基醚、二苯基
酮、3,3’-二甲基-4-甲氧基二苯基酮、苯甲醯基苯甲酸、苯甲醯基苯甲酸之酯化物、4-苯甲醯基-4’-甲基二苯基硫醚、苄基二甲基縮酮、2-丁氧基乙基-4-甲胺基苯甲酸酯、氯噻噸酮、甲基噻噸酮、乙基噻噸酮、異丙基噻噸酮、二甲基噻噸酮、二乙基噻噸酮、二異丙基噻噸酮、甲胺基甲基苯甲酸酯、1-(4-十二烷基苯基)-2-羥基-2-甲基丙烷-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、甲基苯甲醯基甲酸酯、2-甲基-1-(4-甲硫基苯基)-2-N-嗎啉基丙烷-1-酮、2-苄基-2-二甲胺基-1-(4-嗎啉基苯基)-丁酮-1,2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-s-三嗪、2,4,6-三(三氯甲基)-1,3,5-s-三嗪、2,4-雙(三溴甲基)-6-(4’-甲氧基苯基)-1,3,5-s-三嗪、2,4,6-三(三溴甲基)-1,3,5-s-三嗪、2,4-雙(三氯甲基)-6-(1,3-苯并二氧環戊烷-5-基)-1,3,5-s-三嗪、1-(4-苯基氫硫基苯基)丁烷-1,2-二酮-2-肟-鄰苯甲酸酯、1-(4-甲基氫硫基苯基)丁烷-1,2-二酮-2-肟-鄰乙酸酯、1-(4-甲基氫硫基苯基)丁烷-1-酮肟-鄰乙酸酯、4,4’-雙(二乙胺基)二苯基酮、對二甲胺基苯甲酸異戊酯、對二甲胺基苯甲酸乙酯、2,2’-雙(鄰氯苯基)-4,4’,5,5’-四苯基-1,2’-聯咪唑、重氮萘醌系起始劑、或市售KAYACURE-DMBI、KAYACURE-BDMK、KAYACURE-BP-100、KAYACURE-BMBI、KAYACURE-DETX-S、KAYACURE-EPA(皆為日本化藥製)、DAROCUR 1173、DAROCUR 1116(皆為Merck JAPAN製)、IRGACURE-907(BASF JAPAN製)、IRGACURE-369(BASF JAPAN製)、IRGACURE-379EG(BASF JAPAN製)、IRGACURE-OXE-01(BASF JAPAN製)、IRGACURE-OXE-02(BASF JAPAN製)、IRGACURE-PAG103(BASF
JAPAN製)、TME-三嗪(三和化學製)、聯咪唑(黑金化成製)、STR-110、STR-1(皆為Respe Chemical製)等。
本發明之著色組成物可含有之熱聚合起始劑係有偶氮系化合物或有機過氧化物系。可舉例如2,2’-偶氮雙異丁腈、2,2’-偶氮雙(2,4-二甲基戊腈)、2,2’-偶氮雙(2-甲基丁腈)、過氧化二第三丁基、二過氧化苯甲醯、異丙苯基過氧化新癸酸酯等。
該等光聚合起始劑或熱聚合起始劑可視需要而單獨使用或組合2種以上使用。該等起始劑之含量相對於著色組成物之固形分100質量份通常為50質量份以下,較佳為1至25質量份。
本發明之著色組成物可含有之表面調整劑可舉出聚氧伸乙基山梨醇酐脂肪酸酯、聚氧伸乙基烷基醚、聚氧伸乙基烷基苯基醚、環氧乙烷與環氧丙烷之共聚物等習知非離子系、聚矽氧烷系或聚二甲基矽氧烷系之界面活性劑。
消泡劑可舉出聚矽氧系、乙炔系之習知消泡劑。
防腐防黴劑可舉出脫氫乙酸鈉、苯甲酸鈉、鈉吡啶硫酮-1-氧化物、鋅吡啶硫酮-1-氧化物、1,2-苯并異噻唑啉-3-酮、1-苯并異噻唑啉-3-酮之胺鹽等習知防腐防黴劑。
pH調整劑可舉出氫氧化鈉、氫氧化鉀、氫氧化鋰等氫氧化鹼金屬類、三乙醇胺、二乙醇胺、二甲基乙醇胺、二乙基乙醇胺等3級胺類等習知pH調整劑。
本發明之著色組成物可含有之式(1)所示之次甲基化合物以外之色素可舉出有機顏料、無機顏料及染料等。
本發明之著色組成物中使用有機顏料、無機顏料等顏料時,調配量相對於著色組成物之全固形分一般可為0.5至50質量%。
本發明之著色組成物可含有之有機顏料並無特別限制,可舉例如蒽醌系、酞青素系、三苯基甲烷系、苯并咪唑酮系、喹吖酮系、偶氮螯合物系、偶氮系、異吲哚啉系、異吲哚啉酮系、皮蒽酮系、陰丹士林系、蒽嘧啶系、二溴蒽嵌蒽醌系、黃士酮系、苝系、紫環酮系、喹啉黃系、硫靛藍系、雙噁嗪系、氧雜蒽系等顏料;酸性染料、鹼性染料、直接染料等分別對沉澱劑不溶化之色澱顏料、染色色澱顏料等。更具體而言可舉出色料索引之例如顏料藍1、1:2、9、14、15、15:1、15:2、15:3、15:4、15:6、16、17、19、25、27、28、29、33、35、36、56、56:1、60、61、61:1、62、63、66、67、68、71、72、73、74、75、76、78、79;顏料紫1、1:1、2、2:2、3、3:1、3:3、4、5、5:1、14、15、16、19、23、25、27、29、31、32、37、39、42、44、47、49、50;顏料紅7、14、41、48:1、48:2、48:3、48:4、57:1、81、81:1、81:2、81:3、81:4、81:5、122、146、168、177、178、184、185、187、200、202、208、210、246、254、255、264、270、272、279;顏料橙43、71、73;顏料黃1、2、3、4、5、6、10、12、13、14、15、16、17、18、24、31、32、34、35、35:1、36、36:1、37、37:1、40、42、43、53、55、60、61、62、63、65、73、74、77、81、83、93、94、95、97、98、100、101、104、106、108、109、110、113、114、115、116、117、118、119、120、123、126、127、128、129、138、139、147、150、151、152、153、154、155、156、161、162、164、166、167、
168、169、170、171、172、173、174、175、176、177、179、180、181、182、185、187、188、193、194、198、199、213、214、顏料綠7、36、58、59等。
本發明之著色組成物可含有之無機顏料並無特別限制,可舉例如複合金屬氧化物顏料、碳黑、黑色低氧化鈦、氧化鈦、硫酸鋇、氧化鋅、硫酸鉛、黃色鉛、紅色氧化鐵、群青、普魯士藍、氧化鉻、銻白、鐵黑、氧化鉛、硫化鋅、鎘黃、鎘紅、鋅、錳紫、鈷紫、碳酸鎂等金屬氧化物、金屬硫化物、硫酸鹽、金屬氫氧化物、金屬碳酸鹽等。
本發明之著色組成物可含有之染料並無特別限制,可舉出酸性染料、鹼性染料、直接染料、硫化染料、士林染料、萘酚染料、反應性染料、分散染料等。併用有機溶劑時,較佳為可溶於有機溶劑者,但即使是不溶於有機溶劑之染料也可作為分散體而適宜使用。作為不溶於有機溶劑之染料所週知的配方,例如為酸性染料時,已知與有機胺化合物(例如正丙胺、乙基己基丙酸胺等)反應而改質為胺鹽染料、或使該磺酸基與同有機胺化合物反應而改質為具有磺醯胺基之染料等。該等胺改質染料亦可用於本發明之著色組成物。其具體染料可舉出色料索引之例如C.I.編號之酸性藍1、7、9、15、18、23、25、27、29、40、42、45、51、62、70、80、83、86、87、90、92、96、103、112、113、120、129、138、147、150、158、171、182、192、210、242、243、249、256、259、267、278、280、285、290、296、315、324、335、340;鹼性藍7、11、15、26;溶劑藍2、3、4、5、6、23、25、35、37、38、43、55、59、67、72、124;鹼性紫10;酸性紫17、49;溶劑紫4、5、14;
鹼性紅1、10、29;酸性紅91、92、97、114、138、151、289;溶劑紅45、49、127;酸性黃17、23、25、29、38、40、42、76;溶劑黃4、14、15、24、76、81、82、94、98、162;溶劑橙2、7、11、15、26、56;酸性綠9、16等。
本發明之著色組成物可將式(1)所示之次甲基化合物及黏合劑樹脂與其他成分藉由溶解器或均質機等而混合攪拌並製造。併用顏料或溶解性低之染料時,可將使用適當分散劑藉由塗料攪拌器等分散機而得之分散體添加於著色組成物中加以混合。為了從所調製之著色組成物去除異物等,亦可用過濾器等精密過濾。
本發明之著色組成物可用於各種塗料、水性印墨、油性印墨、噴墨用印墨、彩色濾光片用著色組成物。彩色濾光片用著色組成物之具體用途可舉出液晶顯示裝置、有機EL顯示器、或數位相機等所使用之固體成像元件等之彩色濾光片。
使用本發明之著色組成物之被著色材料可舉例如普通紙、塗被紙、塑膠膜、塑膠基板,但並不限定於該等。又,將本發明之著色組成物賦予至被著色材料之方法可舉出平印印刷、凸版印刷、柔版印刷、噴墨印刷等各種印刷方法或旋轉塗佈器、輥塗佈器等之塗佈方法。
使用本發明之著色組成物之彩色濾光片之製造方法可舉出染色法、電鍍法、印刷法、顏料分散法等。典型例可舉出使用圖案化手法之顏料分散法。圖案化方法之代表例係使用光刻法。作為替代也可使用以下方法:將著色組成物藉由噴墨印表機在不透過遮罩下直接塗佈於基板上,而形成彩色濾光片。
[實施例]
以下藉由實施例進一步具體說明本發明,但本發明並不限定於該等實施例。又,未特別記載時,本文中「份」及「%」為質量基準,且反應溫度為內部溫度。
合成例1(上述具體例之No.4所示之次甲基化合物及No.8所示之次甲基化合物之混合物之合成)
(步驟1-1)
於500ml之四口燒瓶中加入下述式(100)所示之3,4-二甲基苯基肼鹽酸鹽(東京化成工業公司製)55份、3-甲基-2-丁酮(東京化成工業公司製)32份、95%硫酸62份及乙醇220份,在78℃攪拌2小時。冷卻反應液後加入水與甲苯,以水清洗有機層,以飽和食鹽水脫水,以無水硫酸鈉乾燥後,在減壓下濃縮,藉此而得到下述式(101)所示之中間物化合物(2種類之化合物之混合物)44份。
(步驟1-2)
於300ml之四口燒瓶中加入步驟1-1所得之上述式(101)所示的中間物化合物44份、甲苯88份及硫酸二甲酯(東京化成工業公司製)54份,在90℃攪拌2小時。冷卻反應液至室溫後,加入水70份及氫氧化鉀34份,在50℃攪拌1小時。以水清洗有機層,以飽和食鹽水脫水,以無水硫酸鈉乾燥後,在減壓下濃縮,藉此而得到下述式(102)所示之中間物化合物(2種類之化合物之混合物)42份。
(步驟1-3)
於200ml之燒杯中加入DMF58份,將液溫保持於10℃以下並滴入氯化磷醯(純正化學公司製)30份。於其中加入步驟1-2所得之上述式(102)所示中間物化合物40份,在40℃攪拌1小時。冷卻反應液至室溫後,將反應液注入冰水中,加入25%氫氧化鈉水溶液直到pH成為10。進一步加熱至80℃,析出結晶後冷卻反應液至室溫。過濾收集所析出之結晶並清洗、乾燥,藉此而得到下述式(103)所示之中間物化合物(2種類之化合物之混合物)37份。
(步驟1-4)
於3,000ml之燒杯中加入甲醇1,400份、步驟1-3所得之上述式(103)所示中間物化合物105份、4-氯苯胺-3-磺酸(東京化成工業公司製)95.05份、水460份及乙酸150份,在45℃攪拌2小時。過濾收集所析出之結晶並清洗、乾燥,藉此獲得上述具體例之No.4所示之次甲基化合物及No.8所示之次甲基化合物之混合物163份。
合成例A(黏合劑樹脂之合成)
於500ml之四口燒瓶加入甲基乙酮160份、甲基丙烯酸10份、甲基丙烯酸苄酯33份及α,α’-偶氮雙(異丁腈)1份,一邊攪拌一邊使氮氣流入燒瓶內30分鐘。其後升溫至80℃,在80至85℃直接攪拌4小時。反應結束後,冷卻至室溫,而得無色透明之均一共聚物溶液。將其在異丙醇與水之1:1混合溶液中沉澱、過濾,取出固形分並乾燥,而得黏合劑樹脂。所得黏合劑樹脂之聚苯乙烯換算重量平均分子量為18,000,酸價為152(mgKOH/g)。
實施例1(本發明之著色組成物之製作)
將C.I.顏料綠59/合成例1所得No.4所示之次甲基化合物與No.8所示之次甲基化合物的混合物/DISPERBYK-2001(BYK.JAPAN公司製)/丙二醇單甲基醚乙酸酯/丙二醇單乙基醚/合成例A所得黏合劑樹脂以0.09份/0.03份/0.62份/19.0份/1.2份/3.9份之組成比混合後,添加0.3mm二氧化鋯珠50份,以塗料攪拌器處理2小時。過濾去除珠,而得本發明之著色組成物1。
實施例2(本發明之彩色濾光片之製作)
使用旋轉塗佈器將實施例1所得的本發明之著色組成物1塗佈於玻璃基板上後,在80℃乾燥10分鐘,製作本發明之彩色濾光片(染料著色體1)。
比較例1(比較用著色組成物之製作)
除了將合成例1所得No.4所示之次甲基化合物與No.8所示之次甲基化合物的混合物變更為C.I.Pigment Yellow 185以外,以與實施例1之相同方式獲得比較用著色組成物1。
比較例2(比較用彩色濾光片之製作)
除了將實施例1所得本發明之著色組成物1變更為比較例1所得比較用著色組成物1以外,以與實施例2之相同方式製作比較用彩色濾光片(比較用染料著色體1)。
(亮度評價)
使用紫外線可見光分光光度計UV-1700(島津製作所公司製)測定實施例2及比較例2所得本發明之彩色濾光片及比較用彩色濾光片之分光透過率,評價C光源之CIE之XYZ表色系中的x、y之色度座標與亮度Y。每次計算亮度Y所需之色度x及y係使用日本專利文獻2018-154781號公報所記載的一般習知色度x及y。再者,亮度Y越大表示亮度越高,越為優異。結果呈示於表1。
由表1之結果可知,相較於使用比較用著色組成物製作之比較用彩色濾光片,使用本發明之著色組成物1製作之彩色濾光片顯示良好亮度。
(產業之可利用性)
藉由使用含有式(1)所示特定構造之次甲基化合物、黏合劑樹脂及分散劑之本發明之彩色濾光片用著色組成物,可提供亮度優異之彩色濾光片之綠色像素。
Claims (9)
- 如申請專利範圍第1項所述之彩色濾光片用著色組成物,其中R1至R4各自獨立地為氫原子、鹵原子或碳數1至4之烷基、且R7及R9之任一者為-SO3 -且另一者為氫原子、鹵原子、碳數1至6之烷基、甲氧基或碳數1至3之烷基羰基胺基。
- 如申請專利範圍第1或2項所述之彩色濾光片用著色組成物,其中分散劑含有丙烯酸系分散劑。
- 如申請專利範圍第1或2項所述之彩色濾光片用著色組成物,其進一步含有顏料。
- 如申請專利範圍第3項所述之彩色濾光片用著色組成物,其進一步含有顏料。
- 如申請專利範圍第4項所述之彩色濾光片用著色組成物,其中顏料含有具有酞青素構造之顏料。
- 如申請專利範圍第5項所述之彩色濾光片用著色組成物,其中顏料含有具有酞青素構造之顏料。
- 一種彩色濾光片,係使用申請專利範圍第1至7項中任一項所述之彩色濾光片用著色組成物而得。
- 一種液晶顯示裝置、有機EL顯示器或固體成像元件,係裝設有申請專利範圍第8項所述之彩色濾光片。
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